Fats natural organic compounds, full esters of glycerol and monobasic fatty acids; belong to the class of lipids. Fats are esters of glycerol

Fats and oils are natural esters that are formed by a trihydric alcohol - glycerol and higher fatty acids with an unbranched carbon chain containing even number carbon atoms. In turn, sodium or potassium salts of higher fatty acids are called soaps.

When carboxylic acids interact with alcohols ( esterification reaction) esters are formed:

This reaction is reversible. The reaction products can interact with each other to form the initial substances - alcohol and acid. Thus, the reaction of esters with water - ester hydrolysis - is the reverse of the esterification reaction. Chemical equilibrium, which is established when the rates of direct (esterification) and reverse (hydrolysis) reactions are equal, can be shifted towards the formation of ether by the presence of water-removing agents.

Esters in nature and technology

Esters are widely distributed in nature, are used in technology and various industries industry. They are good solvents organic substances, their density is less than the density of water, and they practically do not dissolve in it. Thus, esters with a relatively small molecular weight are highly flammable liquids with low boiling points and smell of various fruits. They are used as solvents for varnishes and paints, flavorings of food industry products. For example, butyric acid methyl ester has the smell of apples, the ethyl ester of this acid has the smell of pineapples, isobutyl ester of acetic acid has the smell of bananas:

Esters of higher carboxylic acids and higher monobasic alcohols are called waxes. So, beeswax is the main
together from an ester of palmitic acid and myricyl alcohol C 15 H 31 COOC 31 H 63 ; sperm whale wax - spermaceti - an ester of the same palmitic acid and cetyl alcohol C 15 H 31 COOC 16 H 33.

Fats

The most important representatives of esters are fats.

Fats- natural compounds that are esters of glycerol and higher carboxylic acids.

The composition and structure of fats can be reflected by the general formula:

Most fats are formed by three carboxylic acids: oleic, palmitic and stearic. Obviously, two of them are limiting (saturated), and oleic acid contains a double bond between carbon atoms in the molecule. Thus, the composition of fats can include residues of both saturated and unsaturated carboxylic acids in various combinations.

Under normal conditions, fats containing residues of unsaturated acids in their composition are most often liquid. They are called oils. Mostly fats plant origin- linseed, hemp, sunflower and other oils. Less common are liquid fats of animal origin, such as fish oil. Most natural fats of animal origin under normal conditions are solid (fusible) substances and contain mainly residues of saturated carboxylic acids, for example, mutton fat. So, Palm oil- solid under normal conditions fat.

The composition of fats determines their physical and chemical properties. It is clear that for fats containing residues of unsaturated carboxylic acids, all reactions of unsaturated compounds are characteristic. They decolorize bromine water, enter into other addition reactions. The most important reaction in practical terms is the hydrogenation of fats. Solid esters are obtained by hydrogenation of liquid fats. It is this reaction that underlies the production of margarine - solid fat from vegetable oils. Conventionally, this process can be described by the reaction equation:

hydrolysis:

Soaps

All fats, like other esters, undergo hydrolysis. The hydrolysis of esters is a reversible reaction. To shift the equilibrium towards the formation of hydrolysis products, it is carried out in an alkaline environment (in the presence of alkalis or Na 2 CO 3). Under these conditions, the hydrolysis of fats proceeds irreversibly and leads to the formation of salts of carboxylic acids, which are called soaps. Hydrolysis of fats in an alkaline environment is called saponification of fats.

When fats are saponified, glycerol and soaps are formed - sodium or potassium salts of higher carboxylic acids:

Crib

Fats are esters of the trihydric alcohol glycerol and higher carboxylic acids, the general formula of which is shown on the slide.

Fats, as it is not surprising, belong to esters. Stearic acid C 17 H 35 COOH (or other fatty acids close to it in composition and structure) and trihydric alcohol glycerol C 3 H 5 (OH) 3 participate in their formation. Here's what the molecule diagram of such an ether looks like:

H 2 C-O -C (O) C 17 H 35

HC-O-C(O)C 17 H 35

H 2 C-O -C (O) C 17 H 35 tristearin, ester of glycerol and stearic acid, glycerol tristearate.

Fats have complex structure– this confirms the model of the tristearate molecule.

Chemical properties of fats: hydrolysis and hydrogenation of liquid fats.

For fats containing residues of unsaturated carboxylic acids, all reactions of unsaturated compounds are characteristic. The most important addition reaction of practical importance is hydrogenation of liquid fats . This reaction underlies the production of margarine (solid fat) from vegetable oil.

All fats, like other esters, undergo hydrolysis .

Hydrolysis of fats also occurs in our body: when fats enter the digestive organs, they are hydrolyzed under the influence of enzymes to form glycerol and carboxylic acids. Hydrolysis products are absorbed by the intestinal villi, and then fat is synthesized, but already characteristic of this organism. Subsequently, they are hydrolyzed and gradually oxidized to carbon dioxide and water. When fats are oxidized in the body, a large amount of energy is released. For people engaged in heavy physical labor, the energy expended is most easily compensated fatty foods. Fats supply fat-soluble vitamins and other biologically active substances to body tissues.

Depending on the conditions, hydrolysis happens:

¾ Water(without catalyst, at high temperature and pressure).

¾ Acid(in the presence of an acid as a catalyst).

¾ Enzymatic(occurs in living organisms).

¾ Alkaline (under the action of alkalis).

The hydrolysis of esters is a reversible reaction. To shift the equilibrium towards the reaction products, it is carried out in an alkaline medium (in the presence of alkalis or carbonates alkali metals e.g. sodium carbonate).

DATEM is the abbreviation for a dietary supplement called Glycerol and Diacetyl Tartaric Fatty Acid Esters. It is registered under number E472e and is also known as Diacetyltartaric and fatty acid esters of glycerol, Mixed acetic and tartaric acid esters of mono- and diglycerides of fatty acids.

For industrial use, these compounds are synthesized chemically. The first option for their preparation is the interaction of diacetyltartaric anhydride with mono- and diglycerides of fatty acids in the presence of acetic acid, and the second option is the reaction between acetic anhydride and fatty acid glycerides in the presence of tartaric acid. Soybean oil is often used as a raw material for fatty acids involved in the synthesis of E472e. The finished substance appearance is an oily, waxy liquid, paste or hard wax, yellowish-white in color, with a taste and smell. It is easily soluble in water (both cold and hot), alcohols, acetone and ethyl acetate.

Additive E472e allowed in Russia for adding to some products according to their TI and performs the functions of an emulsifier, complexing agent and stabilizer in them. Once in the human body, it is completely processed, without adversely affecting health. This is confirmed by animal studies. Therefore this the supplement is considered safe for a person. But it is recommended not to consume more than 50 mg / kg of body weight per day - this is the maximum dose established in Canada.

See MIXED ESTERS OF GLYCERIN AND TARGETIC, ACETIC AND FATTY ACIDS below.

ESTERS OF GLYCEROL AND LACTIC AND FATTY ACIDS Е472b

Additive E472b is called Glycerol and lactic and fatty acid esters, as well as Lactic and fatty acid esters of glycerol, Lactylated mono- and diglycerides, Lactylated mono- and diglycerides, Lactoglycerides, Lactoglycerides or LACTEM.

In the Russian food industry, the additive E472b is allowed as an emulsifier, stabilizer and complexing agent. And when it enters the body, it is broken down into separate acids and fats and then absorbed like any natural fats.

The allowable daily intake is set at 50 mg/kg body weight. No side effects were observed when this norm was observed.. Sometimes it is classified as a substance - possible carcinogens, but there is no exact data on this topic.

Technological functions	Emulsifiers, flour treatment agents, foaming agents, foam stabilizers.
Synonyms	Lactylated mono- and diglycerides, lactoglycerides; English lactic and fatty acids esters of glycerol, lactylated mono- and diglycerides, lactylic esters of fatty acids, LACTEM, lactoglycerides; German Lactoglyceride, Milchsaureester der Mono- und Diglyceride, LACTEM, Mono- und Diglyceride von Speisefettsauren, verestert mit Milchsaure; fr. esters lactiques et d "acides gras de glycerine, mono- et diglycerides lactyles.
Compound	A mixture of esters of glycerol with fatty and lactic acids.
Molecular mass	122,14
Compound	A mixture of four isomers of 1,2,3,4-tetrahydroxybutane.
Structural formula	Ri, R2, R3 - lactic or fatty acid residues, or hydrogen
Organoleptic properties	Oils and waxes are whitish to brownish in color with an oily, slightly bitter taste.
Physicochemical characteristics	The melting point and hardness are noticeably lower than those of the corresponding monoglycerides. dispersed in hot water; insoluble in cold water.
Receipt	Direct interaction of the components with each other or esterification of (distilled) monoglycerides with lactic acid in an equilibrium reaction with rearrangement of the acyl group. Impurities: mono-, di- and triglycerides, accompanying fats in the islands, lactic and polylactic acids.
Specifications
Metabolism and toxicity	Completely hydrolyzed and absorbed. The high hydrolytic capacity of these emulsifiers results in what is usually already in the food product, especially in bakery products, they are decomposed to a large extent into monoglycerides and lactates and are thus excreted from the intestine.
Hygiene standards	ADI 50 mg/kg body weight per day. There are no hazards according to GN-98. Codex: allowed in margarines up to 10 g/kg. In the Russian Federation, they are allowed as emulsifiers in food products according to TI in an amount according to TI (clause 3.6.6 of SanPiN 2.3.2.1293-03).
Application	Etherification of mono- and diglycerides with lactic and polylactic acids leads to: narrowing of the melting area; decrease in resistance to hydrolysis and heating; an increase in the HLB value to 4-5; facilitating recycling, especially with the addition of soap; special activity at the interface with the gas phase. For these reasons, lactic glycerides are excellent emulsifiers for whipping three-phase systems and facilitate foaming (air saturation, whipping) of dough, margarines for baking, ice cream, desserts without pre-treatment. Due to its tendency to hydrolyze, this emulsifier can only be used in powdered products. Other applications: The beneficial effect of lactic acid glycerides on the skin allows them to be used in cosmetics, but due to their tendency to hydrolyze, their use is limited to foam masks and similar products prepared immediately before use.

ESTERS OF GLYCEROL AND RESIN ACIDS Е445

E445 Glycerol Ether refers to a group of stabilizers designed to maintain the viscosity and consistency of food products. For example, pectin has a similar effect. The main active ingredient of the supplement is glucomannan, which is characterized by a reduced calorie content and a large amount of dietary fiber. To obtain it, resin acids are extracted from the stumps of old pines. And then they carry out a reaction between them and glycerol. The result is a pale amber to yellow solid that is insoluble in water but readily soluble in organic solvents (acetone and benzene).

Esters of glycerol and resin acids allowed in the Russian food industry for the manufacture of cloudy flavored soft drinks and for the surface treatment of citrus fruits. At the same time, they perform the function of an emulsifier (i.e., they increase the miscibility of those substances that do not mix under normal conditions) and a stabilizer (i.e., they contribute to a better preservation of the texture, shape and consistency of food products).

Effect on the human body:
Additive E445, when ingested, is then excreted from the human body with urine. She is considered safe for humans. It is she who serves as a good alternative for.

Resin esters can be allergens and cause irritation skin. The additive E445 used as an emulsifier can lead to irritation of the mucous membranes of the body and to an upset stomach. Particular care should be taken to use products containing the additive E445 for people with metabolic disorders. In production baby food esters of glycerol are not used.

Food additive E445 is allowed in Russian Federation according to norms and TI

Technological functions	Emulsifiers, stabilizers, thickeners.
Synonyms	English ester gum, glycerol esters of wood rosin; German Glycerinester der Harzsauren, Glycerinester aus Wurzelharz; fr. esters de glycerol and acides gommique.
CAS#	8050-30-4.
Compound	A mixture of tri- and diglycerol esters of resin acids, a complex mixture of isomeric diterpenoid monocarboxylic acids having molecular formula type: C 20 H 30 2, Ch. arr. abietic acid.
Organoleptic properties	Yellow to pale amber solid.
Physicochemical characteristics	Solv. in acetone and benzene; insoluble in water.
Receipt	Esterification of glycerol with resin acids obtained by extraction from old pine stumps, followed by purification by steam distillation or countercurrent steam distillation. Fluorescin is iodinated in water or alcohol solutions. Erythrosin is the sodium salt. Calcium, potassium salts and aluminum lacquer are also allowed in the EU. Impurities: sodium chloride, sodium sulfate.
Specifications
Hygiene standards	In the Russian Federation, they are allowed as emulsifiers, consistency stabilizers, thickeners, texturizers in non-alcoholic beverages with flavorings cloudy in the amount of up to 100 mg/kg; in citrus fruits for surface treatment in an amount of up to 50 mg/kg (clause 3.6.7 of SanPiN 2.3.2.1293-03).
Application	As a chewing gum base component, a consistency stabilizer (thickener) in beverages, it also regulates the density of essential oils in beverages, preventing them from floating to the surface of the beverage during storage.

ESTERS OF GLYCEROL AND ACETIC AND FATTY ACIDS E472a

Additive E472a refers to stabilizers used to maintain and improve the viscosity and consistency of food products. These esters are synthesized from natural fatty acids and. For example, they can be obtained by the interaction of fats with acetanhydride or by transesterification of triacetin. finished product It is a white or pale yellow oil or soft wax with a faint smell of vinegar. It is highly soluble in ethyl alcohol but insoluble in water.

In the Russian Federation, the additive E472a is permitted and is used to mix under normal conditions immiscible products (emulsifier), to stabilize their consistency and texture (stabilizer) and as a complexing agent. It can be found in foods such as instant rice, bread, biscuits, crackers, grain-based products, other products according to their TI, as well as in dyes and fat-soluble antioxidants.

Effect on the human body:
In the body, acetoglycerides are well absorbed like any other fats and do not provide any negative impact on health. Therefore, the maximum allowable amount of their consumption per day is not limited.

Technological functions	Covers, separators.
Synonyms	Mono- and diglycerides of acetic and fatty acids, acetylated mono- and diglycerides, acetoglycerides; English acetic and fatty acid esters of glycerol, acetylated mono- and diglycerides, acetoglyc-erides, acetic acid esters of mono-and diglycerides; German Acetofette, Essigsaureester der Mono- und Diglyceride, Mono- und Diglyceride von Speisefettsauren, verestert mit Essigsaure; fr. esters acetiques et d "acides gras de glycerol, mono- et diglycerides acetyles
Compound	Esters of glycerol with one or two edible fatty acids and one or two molecules of acetic acid.
Structural formula	Rj, R2, R3 - fatty acid residue, either COCH3 or hydrogen
Organoleptic properties	From light yellow oil to plastic wax with a slight smell of vinegar.
Physicochemical characteristics	The melting point is lower than that of the corresponding monoglycerides. Solv. in ethanol; insoluble in water.
Receipt	Interaction of fats or partial glycerides with acetane hydride or transesterification of triacetin. Impurities: mono-, di- and triglycerides associated with fats in the islands.
Specifications
Metabolism and toxicity
Hygiene standards	Chipboard is not limited. There are no hazards according to GN-98. In the Russian Federation, they are allowed as emulsifiers in food products according to TI in an amount according to TI (clause 3.6.6 of SanPiN 2.3.2.1293-03). Basically, monoglycerides of saturated fatty acids and one or two molecules of acetic acid (50/70/90% esterified free OH groups).
Application	Acetofats are di- and triglycerides of natural fatty acids with an even number of carbon atoms from C 2 to C 18, i.e. with very different chain lengths. Since they contain only saturated fatty acids, they are resistant to oxygen and light, as well as tarring and rancidity, but easily split off acetic acid. They hardly have an emulsifying effect, but can affect the crystal structure and plasticity of fats; act as a lubricant, separating agent; form hard, adherent and fracture-resistant coatings or films. This allows the use of acetofats as coating masses for sausages, cheeses, nuts, raisins, sweets, as well as food packaging materials; plasticizers for brittle waxes, hard fats, chewing gum; consistency regulators in margarines, fat coatings, mayonnaises, fillers. Other applications: as consistency regulators and film formers in skin care creams, lotions, suppositories.
Commodity forms	Basically, monoglycerides of saturated fatty acids and one or two molecules of acetic acid (50/70/90% esterified free OH groups).

ESTERS OF LACTYLATED FATTY ACIDS GLYCEROL AND PROPYLENE GLYCOL E 478

Food supplement E 478

Previously, the additive E 478 was used in the Russian Federation in some products according to their manufacturing technology. But since 2010 she included in the banned list to the use of supplements. In Europe, it was banned already in 1986.

Lactylated fatty acid esters of glycerol and propylene glycol are used as a stabilizer and emulsifier in high-fat products for the qualitative formation and structuring of fat crystals.
The esterification process of the E 478 additive makes it possible to qualitatively change the melting area, reduce the resistance to hydrolysis, and facilitate the processing of raw materials. Thanks to these properties, esters significantly improve the quality of whipping dough, ice cream, desserts, margarine. Esters are used in the production of dry cream for coffee and sauces, and are also able to prolong the vital activity of yeast cells and protect flavors from taste changes.

Effect on the human body:

Technological functions	Emulsifiers.
Synonyms	English lactylated fatty acids esters of glycerol and propylene glycol, propylenglycollactostearates; German Propylenglycollactosteate; fr. propylenglycollactostearates.
Compound	Mixture of esters of propylene glycol and glycerol and lactic and fatty acids obtained by lactylation of the product of the reaction of edible fats or oils with propylene glycol.
Appearance	More or less solid mass.
Physicochemical characteristics	Dispersible in hot water and moderately soluble in soybean oil.
Specifications
Hygiene standards	In Europe, banned for use in food products. Deleted in March 1986 from Annex II of the EU Emulsifiers Directive. In the Russian Federation, they are allowed as emulsifiers in food products according to TI in an amount according to TI (clause 3.6.9 of SanPiN 2.3.2.1293-03).
Application	To form the structure of fat crystals.

ESTERS OF CITRIC ACID AND MONO- AND DIGLYCERIDES OF FATTY ACIDS Е 472с

Esters of glycerol and citric and fatty acids is a food additive E 472c.

These compounds can be obtained by esterification with and fatty acids. Moreover, fatty acids can be both vegetable and animal origin. Outwardly, it is a wax-like mass in color from white to whitish-yellow. Cytroglycerides are able to dissolve in oils, fats and hydrocarbons, form a dispersion in hot water and are insoluble in cold water and cold ethyl alcohol. They are also characterized by low thermal stability and are easily hydrolyzed.

Effect on the human body:
The permissible daily intake of fatty acid esters is not limited. The human body assimilates E 472f like any digestible natural fats and the additive as a baking improver and stabilizer is considered harmless.
E472f does not cause allergic reactions and does not have a toxic effect. Does not irritate the skin upon direct contact. It is not recommended to abuse products containing an additive for people with metabolic disorders in the body.

Technological functions	Emulsifiers, stabilizers, synergists of antioxidants.
Synonyms	Esters of glycerol and citric and fatty acids, citroglycerides; English citric and fatty acid esters of glycerol, CITREM, citroglycerides; German Citronensaureester der Mono- und Diglyceride, CITREM, Mono- und Diglyceride von Speisefettsauren, verestert mit Citronensaure; fr. esters d "acides citrique et d" acids gras de glycerine.
Compound	An ester of glycerol with one to two food fatty acid molecules and one to two molecules citric acid, and citric acid, as a tribasic acid, can be esterified with other glycerides and, as a hydroxy acid, with other fatty acids. Free acid groups can be neutralized with sodium.
Appearance	From yellowish and brown oils to whitish waxes.
Physicochemical characteristics	A wide melting range, while low heat resistance, a tendency to acyl rearrangement, are easily hydrolyzed. Dispersible in hot water; sol. in hydrocarbons, oils, fats; insoluble in cold water, cold ethanol.
Receipt	Direct interaction of the components with each other or esterification of (distilled) monoglycerides with citric acid. The remaining free carboxyl groups can be neutralized with sodium. Impurities: mono-, di-, and triglycerides, in-va, accompanying fats, esters of citric acid with glycerol or other fatty
Specifications
Metabolism and toxicity	Completely hydrolyzed and absorbed.
Hygiene standards	Chipboard is not limited. There are no hazards according to GN-98. Codex: permitted in margarines up to 10 g/kg (sum of all emulsifiers). In the Russian Federation, they are allowed as consistency stabilizers, emulsifiers in food products according to TI in an amount according to TI (clause 3.6.6 of SanPiN 2.3.2.1293-03).
Application	The esterification of mono- and diglycerides with tribasic citric acid leads to a large number of possible reaction products; ionogenic lipophilic products with a high complexing ability in the fat phase, which therefore has: The value of HLB, which varies depending on the pH of the medium: from 4 in an acidic environment to 12 in a neutral one; - low thermal stability (tendency to further esterification, acyl rearrangements, yellowing); - the property of enhancing the antioxidant effect; - weak antimicrobial activity in an acidic environment. Citric acid glycerides are used as emulsifiers (usually mixed with monoglycerides) and antioxidant synergists (usually mixed with tocopherols), as well as: - in sausages and boiled sausages to prevent the separation of fat during the preparation of minced meat (usually together with diphosphates) in an amount of 0.3-0.5%; - in mixtures for ice cream, desserts, dry cream for coffee and sauces in the amount of 0.2-0.5%, while they stabilize the powder, facilitate its use and improve overrun and stability of the finished product. They also make one-step confectionery preparation possible; improve overrun and reduce the risk of mold (in the amount of 0.5-1.5%); in dry yeast preparations prolong the viability of yeast cells; in flavorings are used to protect against taste changes. Other applications: in creams, lotions and other cosmetic preparations.
Commodity forms	Drugs with a specific area of application.

Tartaric and fatty acid mono- and diglycerides E472d

Food supplement E472d unites a group of substances Mono- and diglycerides of fatty acids and tartaric acid, esters.

In the food industry in Russia and many other countries (with the exception of Australia), the E472d additive is approved for use. It has the properties of an emulsifier, stabilizer and complexing agent, allowing you to improve and stabilize the consistency and texture of food products in accordance with their manufacturing technology. But it is used relatively rarely, since it does not provide any technological advantages compared to other emulsifiers.

Effect on the human body:
Side effects when ingested Esters of mono- and diglycerides of tartaric and fatty acids are not known. In the body, they are broken down and completely absorbed in the same way as natural fats. The maximum allowable value of their daily intake is 30 mg/kg of body weight.

ESTERS OF MONOGLYCERIDES AND SUCINIC ACID, SUCCINYLATED MONOGLYCERIDES E472g

SMG is the abbreviation for a dietary supplement. E472g. She is also known as Monoglycerides and succinic acid esters, Succinylated Monoglycerides, Succinylated monoglycerides.

Succinylated monoglycerides are stabilizers, emulsifiers and baking improvers that preserve and improve the viscosity and texture of food products.
They have a structure of powder, flakes, balls or waxes of white color and do not have a pronounced odor. Soluble in benzenes, ethanols and chloroform. Not soluble in water.

Previously, the additive E472g was used as an emulsifier, stabilizer and complexing agent in various products in accordance with their TI (more often bakery products). But since 2010 in Russia, it was excluded from the list of approved products for use in the food industry. Also, it does not have permission for use in the territory of the European Union.

Effect on the human body:
In the production of baby food, the additive E472g is used very limitedly. People with diseases of the stomach and intestinal tract should be cautious about the use of products with the addition of E472g. When consuming products containing succinylated monoglycerides, one should take into account the fact that harm to the body can only be caused by excessive consumption of the products themselves, and not by the additive. On this basis, people who are recommended to limit the consumption of bakery products should adhere to these recommendations.

Technological functions	Emulsifiers.
Synonyms	English succinylated monoglycerides.
Compound	A mixture of esters of succinic acid and mono- and diglycerides obtained by succinylation of the product of glycerolysis of edible fats and oils, or by direct esterification of glycerol with edible fatty acids.
Appearance	Wax-like mass of off-white color.
Structural formula	R1, R2, R3 - fatty or succinic acid residue, or hydrogen
Specifications
Hygiene standards	Chipboard is missing. In the Russian Federation, they are allowed as emulsifiers in food products according to TI in an amount according to TI(clause 3.6.6 SanPiN 2.3.2.1293-03).
Application	In bakery products (similar to DATEM).

ESTERS OF POLYGLYCEROL AND INTER-ETHERIFIED RICINOLIC ACIDS E 476

The available information about polyglycerol is rather contradictory and requires careful verification.

Additive E 476 does not have official permission to use on the territory of the Russian Federation, Ukraine and some EU countries.

Polyglycerin is obtained from modified plant substances; soy lecithin can serve as a permitted use.

Polyglycerin is used in the manufacture of chocolate and is used as an emulsifier in the food industry. High-fat chocolate does not have very good flow properties, therefore, to reduce cocoa butter consumption, polyglycerol is added to low-fat chocolate, which gives the chocolate a good ability to flow around the filling, resulting in a thinner layer.

Effect on the human body:
According to some information overuse products with E 476 can lead to an increase in the size of the liver and kidneys, as well as to disruption of metabolic processes in the human body. Additive e 476 is not an allergen.
Special care should be taken with the use of polyglycerols by people suffering from stomach diseases and young children.
Additional studies of the effects of polyglycerol on the human body have shown that E476 does not have a toxic effect and is not capable of irritating the skin upon direct contact with the substance. A more expensive counterpart, non-GMO soy lecithin, is harmless.

Technological functions	Emulsifiers, separators, film formers.
Synonyms	Polyglycerylpolyricinoleates; English polyglycerin-polyricinoleate; polyglycerol esters of Interesterified ricinoleic acid; German Polyglycerin-Polyricinoleat, PGPR, Emulgator WOL; fr. polyglycerine-polyricinoleate.
Compound	Esters of condensed glycerols (predominantly di- and triglycerol) with fused hydroxy fatty acids, preferably chains of 5-8 ricinolic acids (12-hydroxybutyric acids).
Structural formula
Molecular mass	Above 1000.
Organoleptic properties	Viscous dark oils.
Physicochemical characteristics	Wide melting area. Chorus. sol. in ether, hydrocarbons, oils; cf. sol. in alcohols; insoluble in water, glycols. Heat resistance and hydrolysis resistance are good.
Receipt	Glycerol and ricinolic acid self-condense (polymerize) and both fractions co-esterify. Impurities: free (poly)glycerols, free fatty (poly) acids, neutral fats.
Specifications
Metabolism and toxicity	The main part of the emulsifier is slowly cleaved in the intestines, polyricinolic acid is absorbed and cleaved in the liver, long polyglycerols are excreted in the feces, short ones in the urine. An increase in the kidneys and liver due to slow reversible hypertrophy of parenchyma cells was registered.
Hygiene standards	ADI 7.5 mg/kg body weight per day. There are no hazards according to GN-98. Codex: allowed as an emulsifier in chocolate, chocolate with fillers, low-fat margarines in an amount not exceeding 5 g/kg (total content of emulsifiers not more than 15 g/kg). In the Russian Federation, they are allowed as emulsifiers in sandwich margarines with a fat content of not more than 41%, in dressings, seasonings, gelled desserts up to 4 g/kg; in sugary confectionery products based on cocoa and chocolate, chocolate icing in an amount up to 5 g / kg (clause 3.6.36 SanPiN 2.3.2.1293-03).
Application	The separate polymerization of fatty acids and glycerol followed by esterification leads to the formation of nonionic, relatively high molecular weight emulsifiers with hydrophilic nests included. This results in a surprisingly strong effect on surface tension in the oil/water and oil/fat crystal systems. Polyglycerol ricinoleates have two main applications: - as an emulsifier and separator in separating emulsions, sprays and waxes for lubricating baking molds, baking sheets, and confectionery molding and stamping machines; - to reduce the viscosity of tempered chocolate masses during grinding, rolling and conching, as well as for better molding and obtaining thin, but dense and durable chocolate coatings (coatings). For a noticeable reduction in the viscosity of chocolate masses, which is necessary in the production of glazes, the concentration of PGPR should be 0.3-0.5%. By consuming chocolate bars with such a high PGPR content, their maximum allowable daily intake (corresponding to 100 g of chocolate) would be reached too quickly. When using thin chocolate coatings on pastries, confectionery and ice cream, there is no danger of exceeding the ADI even at such a high concentration. Other applications: in separating waxes, sprays and emulsions (mould release).

POLYGLYCEROL ESTERS AND FATTY ACIDS Е475

food stabilizer E475 Esters of polyglycerides and fatty acids is a stabilizing agent to improve the consistency and maintain the viscosity of foods. In fact, this substance is a mixture of polyglycerides and fatty acid esters, so it can also play the role of an emulsifier.

Independently, these compounds are formed in fats after frying. And they are artificially synthesized during chemical reaction between fatty acids and .

In the Russian food industry, the additive E475 is allowed and is used for better mixing of products of different consistency, i.e. as an emulsifier. It can be found in milk and cream analogues, fat emulsions, flour and sugar confectionery products, bakery products, desserts, chewing gum, egg products, beverage creamers, emulsified liqueurs, dietary formulas for weight loss, dietary supplements, as well as in the composition dyes and fat-soluble antioxidants.

Effect on the human body:
In the body, this supplement is broken down into simpler components (mono- and diglycerides and fatty acids), and then absorbed similarly to natural fats with the help of an enzyme contained in saliva. According to the results of studies conducted in the UK, it was recognized as safe for humans, and is allowed in many countries around the world. But it is recommended to use it no more than 25 mg / kg of body weight per day.

Technological functions	Emulsifiers, defoamers, dispersing agents.
Synonyms	Polyglycerides; English polyglycerol esters of fatty acids, polyglycerides; German Polyglycerinester von Speisefettsauren, Polyglyceride; fr. polyglycerides.
CAS#	2731-72-8 (triglyceryl monostearate); 34424-98-1 (decaglyceryltetraoleate).
Empirical Formula	C 27 H 53 0 8
Molecular mass	505.70 (triglyceryl monostearate).
Structural formula
Compound	An ester of polycondensed glycerol, preferably diglycerol, with edible fatty acids. May contain additives of sodium salts up to 6%.
Appearance	Oily viscous liquid from light yellow to amber; as the proportion of glycerol increases, the esters become harder and more brittle, so that some can be ground to tan to brown powders.
Physicochemical characteristics	They have a wide melting area, tk. are a mixture of various isomers. Chorus. sol. in alcohols, hydrocarbons; cf. sol. in warm water, warm oils; insoluble in cold water, cold glycols.
natural source	In used frying fats.
Receipt	Condensation of glycerol or addition of glyceride to glycerol and transesterification of the (purified) product with fats or esterification with free fatty acids. Impurities: mono-, di- and triglycerides, free glycerol and free polyglycerol.
Specifications
Metabolism and toxicity	Polyglycerol ethers are broken down by enzymes, free polyglycerols are excreted from the body through the kidneys.
Hygiene standards	ADI 25 mg/kg body weight per day. There are no hazards according to GN-98. Codex: permitted as emulsifiers for margarines up to 5 g/kg, low-fat margarines up to 10 g/kg alone or in combination with other emulsifiers. In the Russian Federation, they are allowed as emulsifiers in beverage creamers in amounts up to 500 mg/kg; in egg products up to 1 g/kg; in sugary confectionery, desserts in an amount up to 2 g/kg; in analogues of milk and cream, in fat emulsions, in chewing gum, in bakery and flour confectionery products, in emulsified liqueurs, in dietary mixtures for weight loss up to 5 g/kg; in biologically active food supplements in the amount according to TI (clause 3.6.35 SanPiN 2.3.2.1293-03).
Application	An increase in the hydrophilic proportion of (poly)glycerol in the emulsifier molecule increases the HLB value to 6-11. Resistance to hydrolysis and temperature effects is sufficient for the use of polyglycerol esters in aqueous systems and allows them to be boiled and sterilized, but polyglycerol esters are not resistant to lipophilic enzymes. Areas of use: - pre-emulsified fats and other baking aids used in buns and pastry fillings (5-20 g/kg); - margarines, semi-fat margarines, mayonnaises, liquid mixes for ice cream and other fat emulsions (5-10 g/kg of fat); - ready meals, spicy sauces (1-3 g/kg); - fats for frying, table fats, oils, margarines as antifoams and crystallization retarders; - flavors and bases for beverages to facilitate the dispersion of citrus oils. Other applications: as an emulsifier in cosmetics (creams, lotions, etc.), as well as in soil treatment products, in the leather industry; for technical purposes, esters with a higher content of free polyglycerols than solvents are often used.

PROPYLENE GLYCOL AND FATTY ACIDS E 477

food stabilizer E 477 Propylene glycol esters of fatty acids

in the Russian Federation and Ukraine is not legally allowed

Effect on the human body:
In the human body Propelin glycol and fatty acid esters are broken down by lipase enzymes and absorbed without side effects. They are considered safe, since they have low toxicity, do not cause mutations and changes in body weight. But sometimes in sensitive people reactions like eczema are possible (not when ingested!). However, despite the harmlessness, it is not recommended to exceed the allowable dose of 25 mg / kg of body weight per day.

Technological functions	Emulsifiers
Synonyms	English propylene glycol esters of fatty acids, propylene glycol mono- and diesters of fatty acids; German Propylenglykolester der Speisefettsauren, Propandiol-FS-Ester; fr. esters de propyleneglycol d "acides gras.
Compound	A mixture of 1,2-propanediol esters with one or two edible fatty acids.
Structural formula	Rj and R2 are either two fatty acid residues, -ORi or a fatty acid residue and hydrogen
Appearance	Clear liquid or plates, grains, etc. from white to cream.
Physicochemical characteristics	mp 30-40°C (propylene glycol esters of saturated fatty acids). Chorus. sol. in alcohols, hydrocarbons; insoluble in water. Heat resistance and resistance to hydrolysis are sufficient for the conditions found in foodstuffs; esters are cleaved by lipases.
Receipt	Esterification of fatty acids with propylene glycol, sometimes followed by rapid distillation to enrich in monomers. Impurities: mono-, di- and triglycerides, polypropylene glycol and its esters with fatty acids.
Specifications
Metabolism and toxicity	The fatty acid part is cleaved by lipases.
Hygiene standards	D SP 25 mg/kg bw/day. There are no hazards according to GN-98. Codex: allowed as an emulsifier in margarines up to 20 g/kg. In the Russian Federation are allowed as an emulsifier in creamers for drinks, in dietary mixtures (products), including for weight loss in an amount up to 1 g/kg; in ice cream (except milk and cream), fruit ice in an amount up to 3 g / kg; in analogues of milk and cream, desserts, sugary confectionery, rich bakery and confectionery products in an amount of up to 5 g/kg; in fat emulsions for bakery and flour confectionery products in the amount of up to 10 g/kg; in whipped decorative dessert coatings, except for dairy coatings, in an amount up to 30 g/kg (clause 3.6.42 SanPiN 2.3.2.1293-03).
Application	Esters of propylene glycol and fatty acids have HLB values of 1.5-3, which is even lower than that of monoglycerides, however, they always crystallize in the a-form and convert fats and other emulsifiers, especially monoglycerides, into an active and easily hydrated alpha form. Therefore, they act as emulsifiers or co-emulsifiers, increasing the overrun of foams, ice creams, desserts and stabilizing other emulsifier preparations. Other uses: as a crystallization regulator in hard fats.
Commodity forms	Directly esterified with 50-60% propylene glycol monoesters and fatty acids or distilled with 90-95% monoesters.

Esters of sucrose and fatty acids E 473

Sucrose and fatty acid esters (Sucrose esters of fatty acids) is a food additive E473, permitted in Russia as an emulsifier.

Like other representatives of the group of stabilizing substances, the chemical parameters, and in addition the properties of the food stabilizer E473 Esters of sucrose and fatty acids, allow the use of the additive as a formative agent, i.e. a substance that imparts a consistency defined by sanitary and epidemiological standards food products. In addition, the E473 stabilizer has a decisive influence on the consistency and viscosity level of the finished product.

In the food industry of the Russian Federation, the additive E473 can be included in many products, such as cream and its analogues, ice cream and popsicles, milk-based drinks; bakery and confectionery products, as well as fat emulsions for them, desserts; meat products, canned soups and broths, sauces; beverage creamers, soft drinks based on coconut, almonds and anise and alcoholic beverages (except wine and beer), powders for preparing hot drinks. Also, this additive is used for the surface treatment of fresh fruits, the manufacture of dietary mixtures and dietary supplements, fatty solvents and antioxidants, and products containing protein hydrolysates, peptides and amino acids.

Effect on the human body:
In the human body, sucrose and fatty acid esters are gradually broken down into components and absorbed in the same way as natural fats and sugars. They do not have toxic, carcinogenic effects or other side effects. And when used in an amount not exceeding the maximum daily dose - 10 mg / kg, quite safe.

Technological functions	Emulsifiers, flour processing agents, coatings.
Synonyms	Esters of sugar and fatty acids; English sucrose fatty acids, sucrose fatty acids; German Saccharose-Fettsaureester, Zuckerester der Speisefettsaure; fr. esters de sucrose d "acides gras.
Compound	Esters of sucrose and 1,2 or 3 molecules of edible fatty acids
Structural formula	Monoesters: X", X" e H, X"" - fatty acid residue Diesters: X", X"" - fatty acid residues, X"» H Triesters: X", X", X"" - fatty acid residues
Organoleptic properties	Solid gels, soft pieces or powders from white to grayish in color with a buttery bittersweet taste.
Physicochemical characteristics	They have a wide melting area. Solv. in warm alcohols, glycols, other org. solvents; bad sol. in water. The resistance to hydrolysis is sufficient, the heat resistance corresponds to the sugar content.
Receipt	Transesterification with sucrose of methyl and ethyl esters of fatty acids or extraction from the reaction mixture of "sugar-glycerides". For extraction, dimethylformamide, dimethyl sulfoxide, ethyl acetate, isopropanol, propylene glycol, isobutanol, methyl ethyl ketone are used. Impurities: solvent residues, sugar breakdown products.
Specifications
Metabolism and toxicity	In the body, they are slowly broken down by enzymes into fatty acids and sugar.
Hygiene standards	ADI 10 mg/kg body weight per day. Codex: allowed as an emulsifier in margarines up to 10 g/kg and in dry cocoa products up to 10 g/kg alone or in combination with other emulsifiers (total content of emulsifiers not more than 15 g/kg). In the Russian Federation are allowed as emulsifiers in canned soups and broths, concentrated in an amount up to 2 g/kg; into sterilized cream, milk-based drinks, cream analogues, ice cream (except for milk and cream), fruit ice, sugar confectionery, desserts, soft drinks based on coconut, almond, anise, alcoholic drinks except for wine and beer, dietary mixtures (products), including for weight loss in amounts up to 5 g/kg; in meat products treated with heat, in an amount of up to 5 g / kg in terms of fat; in fat emulsions for bakery and flour confectionery products, rich bakery and flour confectionery products, chewing gum, powders for making hot drinks, sauces in amounts up to 10 g/kg; in beverage creamers up to 20 g/kg; in fresh fruits, surface treatment, in biologically active food supplements in the amount according to TI individually or in combination with sugar glycerides (clause 3.6.43 SanPiN 2.3.2.1293-03).
Application	Sucrose fatty acid esters are composed of the usual food components of sugar and fat or fatty acids and would be ideal food emulsifiers with HLB values of 3 to 16 were it not for two drawbacks: The process of obtaining them is very complicated, expensive purification from by-products, catalysts and solvents is necessary, which greatly increases the cost of the product; - sucrose esters are very difficult to dissolve; their processing requires the use of solvents, the processing of conventional commercial mixtures of esters, consisting of 40-60% monoesters and 60-40% di- and triesters, requires preliminary dissolution in glycols or warm alcohol. Monoesters of sucrose and fatty acids greatly reduce the surface tension at the oil-water phase boundary, and are good emulsifiers for oil-in-water systems. Di- and triesters of sucrose and fatty acids are less hydrophilic and do not dissolve in either water or fat. Esters of sucrose and fatty acids chor. manifest themselves in the composition of baking improvers as non-ionic surface-active substances. They can be used as co-emulsifiers to stabilize the active form of monoglycerides in various applications. Sucrose esters are used as a component of wax and fat compositions for coatings, incl. for fresh fruits. Other applications: in technical emulsions, creams and pastes.

10.5. Complex ethers. Fats

Esters- functional derivatives of carboxylic acids,
in the molecules of which the hydroxyl group (-OH) is replaced by an alcohol residue (- OR)

Esters of carboxylic acids - compounds with a general formula.

R–COOR", where R and R" are hydrocarbon radicals.

Esters of saturated monobasic carboxylic acids have general formula:

Physical properties:

· Volatile, colorless liquids

Poorly soluble in water

More often with a pleasant smell

Lighter than water

Esters are found in flowers, fruits, berries. They determine their specific smell.
They are an integral part of essential oils (about 3000 ef.m. are known - orange, lavender, rose, etc.)

Esters of lower carboxylic acids and lower monohydric alcohols have a pleasant smell of flowers, berries and fruits. Esters of higher monobasic acids and higher monohydric alcohols are the basis of natural waxes. For example, beeswax contains an ester of palmitic acid and myricyl alcohol (myricyl palmitate):

CH 3 (CH 2) 14 –CO–O–(CH 2) 29 CH 3

Aroma.

Structural formula.

Ester name

Apple

Ethyl ether

2-methylbutanoic acid

Cherry

Formic acid amyl ester

Pear

Acetic acid isoamyl ester

A pineapple

Butyric acid ethyl ester

(ethyl butyrate)

Banana

Acetic acid isobutyl ester

(Isoamyl acetate also smells like a banana)

Jasmine

Acetic benzyl ether (benzylacetate)

Short names of esters are built on the name of the radical (R ") in the alcohol residue and the name of the RCOO group - in the acid residue. For example, ethyl ester of acetic acid CH 3 COO C 2 H 5 called ethyl acetate.

Application

· As fragrances and odor intensifiers in the food and perfume (soap, perfume, cream) industries;

· In the production of plastics, rubber as plasticizers.

plasticizers – substances that are introduced into the composition of polymeric materials to impart (or increase) elasticity and (or) plasticity during processing and operation.

Application in medicine

In the late 19th and early 20th centuries, when organic synthesis was taking its first steps, many esters were synthesized and tested by pharmacologists. They became the basis of such drugs as salol, validol, etc. As a local irritant and analgesic, methyl salicylate was widely used, which has now been practically superseded by more effective drugs.

Obtaining esters

Esters can be obtained by reacting carboxylic acids with alcohols ( esterification reaction). The catalysts are mineral acids.

The esterification reaction under acid catalysis is reversible. The reverse process - the cleavage of an ester by the action of water to form a carboxylic acid and an alcohol - is called ester hydrolysis.

RCOOR " + H 2 O ( H +) ↔ RCOOH + R "OH

Hydrolysis in the presence of alkali proceeds irreversibly (because the resulting negatively charged carboxylate anion RCOO does not react with the nucleophilic reagent - alcohol).

This reaction is called saponification of esters(by analogy with the alkaline hydrolysis of ester bonds in fats in the production of soap).

Fats, their structure, properties and applications

"Chemistry everywhere, chemistry in everything:

In everything we breathe

In everything we drink

Everything we eat."

In everything we wear

People have long learned to isolate fat from natural objects and use it in everyday life. Fat burned in primitive lamps, illuminating the caves of primitive people, grease was smeared on skids, along which ships were launched. Fats are the main source of our nutrition. But malnutrition, a sedentary lifestyle leads to overweight. Desert animals store fat as a source of energy and water. The thick fat layer of seals and whales helps them swim in the cold waters of the Arctic Ocean.

Fats are widely distributed in nature. Along with carbohydrates and proteins, they are part of all animal and plant organisms and constitute one of the main parts of our food. Sources of fats are living organisms. Among animals, these are cows, pigs, sheep, chickens, seals, whales, geese, fish (sharks, codfish, herring). From the liver of cod and shark, fish oil is obtained - a medicine, from herring - fats used to feed farm animals. Vegetable fats are most often liquid, they are called oils. Fats of plants such as cotton, flax, soybeans, peanuts, sesame, rapeseed, sunflower, mustard, corn, poppy, hemp, coconut, sea buckthorn, dogrose, oil palm and many others are used.

Fats perform various functions: building, energy (1 g of fat gives 9 kcal of energy), protective, storage. Fats provide 50% of the energy required by a person, so a person needs to consume 70-80 g of fat per day. Fats make up 10–20% of a healthy person's body weight. Fats are an essential source of fatty acids. Some fats contain vitamins A, D, E, K, hormones.

Many animals and humans use fat as a heat-insulating shell, for example, in some marine animals, the thickness of the fat layer reaches a meter. In addition, in the body, fats are solvents for flavors and dyes. Many vitamins, such as vitamin A, are soluble only in fats.

Some animals (more often waterfowl) use fats to lubricate their own muscle fibers.

Fats increase the effect of food satiety, as they are digested very slowly and delay the onset of hunger .

The history of the discovery of fats

Back in the 17th century. German scientist, one of the first analytical chemists Otto Tachenius(1652-1699) first suggested that fats contain a "hidden acid".

In 1741 a French chemist Claude Joseph Geoffrey(1685-1752) discovered that when soap (which was prepared by boiling fat with alkali) was decomposed with acid, a mass was formed that was greasy to the touch.

The fact that glycerin is included in the composition of fats and oils was first discovered in 1779 by the famous Swedish chemist Carl Wilhelm Scheele.

For the first time, the chemical composition of fats was determined at the beginning of the last century by a French chemist Michel Eugene Chevreul, the founder of the chemistry of fats, the author of numerous studies of their nature, summarized in a six-volume monograph "Chemical studies of bodies of animal origin".

1813 E. Chevreul established the structure of fats, thanks to the reaction of hydrolysis of fats in an alkaline medium. He showed that fats consist of glycerol and fatty acids, and this is not just a mixture of them, but a compound that, by adding water, decomposes into glycerol and acids.

Synthesis of fats

In 1854, the French chemist Marcelin Berthelot (1827–1907) carried out an esterification reaction, that is, the formation of an ester between glycerol and fatty acids, and thus synthesized fat for the first time.

General formula of fats (triglycerides)

Fats - esters of glycerol and higher carboxylic acids. The common name for these compounds is triglycerides.

Fat classification

Animal fats contain mainly glycerides of saturated acids and are solids. Vegetable fats, often referred to as oils, contain glycerides of unsaturated carboxylic acids. These are, for example, liquid sunflower, hemp and linseed oils.

Natural fats contain the following fatty acids

Saturated:

stearic (C 17 H 35 COOH)

palmitic (C 15 H 31 COOH)

Oily (C 3 H 7 COOH)

COMPOSED

ANIMALS

FAT

Unsaturated :

oleic (C 17 H 33 COOH, 1 double bond)

linoleic (C 17 H 31 COOH, 2 double bonds)

linolenic (C 17 H 29 COOH, 3 double bonds)

arachidonic (C 19 H 31 COOH, 4 double bonds, less common)

COMPOSED

vegetal

FAT

Fats are found in all plants and animals. They are mixtures of full esters of glycerol and do not have a distinct melting point.

· Animal fats(mutton, pork, beef, etc.), as a rule, are solids with a low melting point (fish oil is an exception). Residues predominate in solid fats rich acids.

· Vegetable fats - oils (sunflower, soybean, cottonseed, etc.) - liquids (exception - coconut oil, cocoa bean oil). Oils contain mostly residues unsaturated (unsaturated) acids.

Chemical properties of fats

1. Hydrolysis, or saponification , fat occurs under the action of water, with the participation of enzymes or acid catalysts (reversibly), in this case, an alcohol is formed - glycerol and a mixture of carboxylic acids:

or alkalis (irreversible). Alkaline hydrolysis produces salts of higher fatty acids called soaps. Soaps are obtained by hydrolysis of fats in the presence of alkalis:

Soaps are potassium and sodium salts of higher carboxylic acids.

2. Hydrogenation of fats – the conversion of liquid vegetable oils into solid fats is of great importance for food purposes. The product of the hydrogenation of oils is solid fat (artificial lard, salomas). Margarine- edible fat, consists of a mixture of hydrogenated oils (sunflower, corn, cottonseed, etc.), animal fats, milk and flavorings (salt, sugar, vitamins, etc.).

This is how margarine is obtained in industry:

Under the conditions of the oil hydrogenation process (high temperature, metal catalyst), some of the acidic residues containing C=C cis bonds are isomerized into more stable trans isomers. The increased content of trans-unsaturated acid residues in margarine (especially in cheap varieties) increases the risk of atherosclerosis, cardiovascular and other diseases.

The reaction for obtaining fats (esterification)

The use of fats

Fats are food. Biological role fat

Animal fats and vegetable oils, along with proteins and carbohydrates, are one of the main components of normal human nutrition. They are the main source of energy: 1 g of fat when completely oxidized (it takes place in cells with the participation of oxygen) gives 9.5 kcal (about 40 kJ) of energy, which is almost twice as much as can be obtained from proteins or carbohydrates. In addition, fat reserves in the body practically do not contain water, while protein and carbohydrate molecules are always surrounded by water molecules. As a result, one gram of fat provides almost 6 times more energy than one gram of animal starch - glycogen. Thus, fat should rightly be considered a high-calorie "fuel". It is mainly used to maintain normal temperature. human body, as well as for the work of various muscles, so even when a person does nothing (for example, sleeps), every hour he needs about 350 kJ of energy to cover energy costs, about the same power has an electric 100-watt light bulb.

To provide the body with energy adverse conditions it creates fat reserves that are deposited in the subcutaneous tissue, in the fatty fold of the peritoneum - the so-called omentum. Subcutaneous fat protects the body from hypothermia (especially this function of fat is important for marine animals). For thousands of years, people have been doing hard physical work, which required a lot of energy and, accordingly, enhanced nutrition. Only 50 g of fat is enough to cover the minimum daily human need for energy. However, with moderate physical activity, an adult should receive slightly more fat from food, but their amount should not exceed 100 g (this gives a third of the calorie content of a diet of about 3000 kcal). It should be noted that half of these 100 g is found in food in the form of so-called hidden fat. Fats are found in almost all foods in large numbers they are even in potatoes (there are 0.4%), in bread (1-2%), in oatmeal (6%). Milk usually contains 2-3% fat (but there are special varieties skimmed milk). Quite a lot of hidden fat in lean meat - from 2 to 33%. Hidden fat is present in the product in the form of individual tiny particles. Fats in almost pure form are lard and vegetable oil; in butter about 80% fat, in ghee - 98%. Of course, all the above recommendations for fat consumption are averages, they depend on gender and age, physical activity and climatic conditions. With excessive consumption of fats, a person quickly gains weight, but we should not forget that fats in the body can also be synthesized from other products. It is not so easy to “work off” extra calories through physical activity. For example, jogging 7 km, a person spends about the same amount of energy as he receives by eating just one hundred-gram bar of chocolate (35% fat, 55% carbohydrates). Physiologists have found that with physical activity, which is 10 times higher than usual, a person who received a fat diet was completely exhausted after 1.5 hours. With a carbohydrate diet, a person withstood the same load for 4 hours. This seemingly paradoxical result is explained by the peculiarities of biochemical processes. Despite the high "energy intensity" of fats, obtaining energy from them in the body is a slow process. This is due to the low reactivity of fats, especially their hydrocarbon chains. Carbohydrates, although they provide less energy than fats, "allocate" it much faster. Therefore, before physical activity, it is preferable to eat sweet rather than fatty foods. An excess of fats in food, especially animal fats, also increases the risk of developing diseases such as atherosclerosis, heart failure, etc. There is a lot of cholesterol in animal fats (but we should not forget that two-thirds of cholesterol is synthesized in the body from non-fat foods - carbohydrates and proteins).

It is known that a significant proportion of the fat consumed should be vegetable oils, which contain compounds that are very important for the body - polyunsaturated fatty acids with several double bonds. These acids are called "essential". Like vitamins, they must be supplied to the body in ready-made. Of these, arachidonic acid has the highest activity (it is synthesized in the body from linoleic acid), the least activity is linolenic acid (10 times lower than linoleic acid). According to various estimates, the daily human need for linoleic acid ranges from 4 to 10 g. Most of all linoleic acid (up to 84%) is in safflower oil, squeezed from safflower seeds, an annual plant with bright orange flowers. A lot of this acid is also found in sunflower and nut oils.

According to nutritionists, a balanced diet should contain 10% polyunsaturated acids, 60% monounsaturated (mainly oleic acid) and 30% saturated. It is this ratio that is ensured if a person receives a third of the fats in the form of liquid vegetable oils - in the amount of 30–35 g per day. These oils are also found in margarine, which contains 15 to 22% saturated fatty acids, 27 to 49% unsaturated fatty acids, and 30 to 54% polyunsaturated fatty acids. By comparison, butter contains 45–50% saturated fatty acids, 22–27% unsaturated fatty acids, and less than 1% polyunsaturated fatty acids. In this respect, high-quality margarine is healthier than butter.

Must be remembered!!!

Saturated fatty acids negatively affect fat metabolism, liver function and contribute to the development of atherosclerosis. Unsaturated (especially linoleic and arachidonic acids) regulate fat metabolism and are involved in the removal of cholesterol from the body. The higher the content of unsaturated fatty acids, the lower the melting point of the fat. The calorie content of solid animal and liquid vegetable fats is approximately the same, but the physiological value of vegetable fats is much higher. Milk fat has more valuable qualities. It contains one third of unsaturated fatty acids and, remaining in the form of an emulsion, is easily absorbed by the body. Despite these positive traits, you can not use only milk fat, since no fat contains an ideal composition of fatty acids. It is best to consume fats of both animal and vegetable origin. Their ratio should be 1:2.3 (70% animal and 30% vegetable) for young people and middle-aged people. The diet of older people should be dominated by vegetable fats.

Fats not only participate in metabolic processes, but are also stored in reserve (mainly in the abdominal wall and around the kidneys). Fat reserves provide metabolic processes, keeping proteins for life. This fat provides energy during physical exertion, if there is little fat in the diet, as well as in severe illness, when due to reduced appetite, it is not enough supplied with food.

Abundant consumption of fat with food is harmful to health: it is stored in large quantities in reserve, which increases body weight, sometimes leading to disfigurement of the figure. Its concentration in the blood increases, which, as a risk factor, contributes to the development of atherosclerosis, coronary heart disease, hypertension, etc.

EXERCISES

1. There is 148 g of a mixture of two organic compounds of the same composition C 3 H 6 O 2. Determine the structure of these values and their mass fractions in the mixture, if it is known that one of them, when interacting with an excess of sodium bicarbonate, releases 22.4 l (N.O.) of carbon monoxide ( IV), and the other does not react with sodium carbonate and an ammonia solution of silver oxide, but when heated with an aqueous solution of sodium hydroxide, forms an alcohol and an acid salt.

Decision:

It is known that carbon monoxide ( IV ) is released when sodium carbonate reacts with acid. There can be only one acid of composition C 3 H 6 O 2 - propionic, CH 3 CH 2 COOH.

C 2 H 5 COOH + N aHCO 3 → C 2 H 5 COONa + CO 2 + H 2 O.

According to the condition, 22.4 liters of CO 2 were released, which is 1 mol, which means there were also 1 mol of acid in the mixture. The molar mass of the starting organic compounds is: M (C 3 H 6 O 2) \u003d 74 g / mol, therefore 148 g is 2 mol.

The second compound upon hydrolysis forms an alcohol and an acid salt, which means it is an ester:

RCOOR' + NaOH → RCOONa + R'OH.

The composition of C 3 H 6 O 2 corresponds to two esters: ethyl formate HSOOS 2 H 5 and methyl acetate CH 3 SOOSH 3. Esters of formic acid react with an ammonia solution of silver oxide, so the first ester does not satisfy the condition of the problem. Therefore, the second substance in the mixture is methyl acetate.

Since the mixture contained one mole of compounds with the same molar mass, their mass fractions are equal and amount to 50%.

Answer. 50% CH 3 CH 2 COOH, 50% CH 3 COOCH 3 .

2. The relative vapor density of the ester with respect to hydrogen is 44. During the hydrolysis of this ester, two compounds are formed, the combustion of equal amounts of which produces the same volumes of carbon dioxide (under the same conditions). Give the structural formula of this ether.

Decision:

The general formula of esters formed by saturated alcohols and acids is C n H 2 n About 2 . The value of n can be determined from the hydrogen density:

M (C n H 2 n O 2) \u003d 14 n + 32 = 44 . 2 = 88 g/mol,

whence n = 4, that is, the ether contains 4 carbon atoms. Since the combustion of alcohol and the acid formed during the hydrolysis of the ester releases equal volumes of carbon dioxide, the acid and alcohol contain the same number of carbon atoms, two each. Thus, the desired ester is formed by acetic acid and ethanol and is called ethyl acetate:



CH 3 -		O-S 2 H 5

Answer. Ethyl acetate, CH 3 COOS 2 H 5 .

________________________________________________________________

3. During the hydrolysis of an ester, the molar mass of which is 130 g / mol, acid A and alcohol B are formed. Determine the structure of the ester if it is known that the silver salt of the acid contains 59.66% silver by weight. Alcohol B is not oxidized by sodium dichromate and easily reacts with hydrochloric acid to form alkyl chloride.

Decision:

An ester has the general formula RCOOR ‘. It is known that the silver salt of the acid, RCOOAg , contains 59.66% silver, therefore the molar mass of salt is: M (RCOOAg) \u003d M (A g )/0.5966 = 181 g/mol, whence M (R ) \u003d 181- (12 + 2. 16 + 108) \u003d 29 g / mol. This radical is ethyl, C 2 H 5 , and the ester was formed by propionic acid: C 2 H 5 COOR '.

The molar mass of the second radical is: M (R ') \u003d M (C 2 H 5 COOR ') - M (C 2 H 5 COO) \u003d 130-73 \u003d 57 g / mol. This radical has the molecular formula C 4 H 9 . By condition, alcohol C 4 H 9 OH is not oxidized Na 2 C r 2 About 7 and easy to react with HCl therefore, this alcohol is tertiary, (CH 3) 3 SON.

Thus, the desired ester is formed by propionic acid and tert-butanol and is called tert-butyl propionate:

		CH 3

C 2 H 5 —	C-O-	C-CH3

		CH 3

Answer . tert-butyl propionate.

________________________________________________________________

4. Write two possible formulas for a fat that has 57 carbon atoms in a molecule and reacts with iodine in a ratio of 1:2. The composition of fat contains residues of acids with an even number of carbon atoms.

Decision:

General formula for fats:

where R, R', R "- hydrocarbon radicals containing an odd number of carbon atoms (another atom from the acid residue is part of the -CO- group). Three hydrocarbon radicals account for 57-6 = 51 carbon atoms. It can be assumed that each of the radicals contains 17 carbon atoms.

Since one fat molecule can attach two iodine molecules, there are two double bonds or one triple bond for three radicals. If two double bonds are in the same radical, then the fat contains a residue of linoleic acid ( R \u003d C 17 H 31) and two stearic acid residues ( R' = R "= C 17 H 35). If two double bonds are in different radicals, then the fat contains two oleic acid residues ( R \u003d R ' \u003d C 17 H 33 ) and a stearic acid residue ( R "= C 17 H 35). Possible fat formulas:

CH 2 - O - CO - C 17 H 31

CH - O - CO - C 17 H 35

CH 2 - O - CO - C 17 H 35

CH 2 - O - CO - C 17 H 33

CH - O - CO - C 17 H 35

CH - O - CO - C 17 H 33

________________________________________________________________

TASKS FOR INDEPENDENT SOLUTION

1. What is an esterification reaction.

2. What is the difference in the structure of solid and liquid fats.

3. What are the chemical properties of fats.

4. Give the reaction equation for the production of methyl formate.

5. Write the structural formulas of two esters and an acid having the composition C 3 H 6 O 2 . Name these substances according to the international nomenclature.

6. Write the equations for esterification reactions between: a) acetic acid and 3-methylbutanol-1; b) butyric acid and propanol-1. Name the ethers.

7. How many grams of fat was taken if 13.44 liters of hydrogen (n.o.) were required to hydrogenate the acid formed as a result of its hydrolysis.

8. Calculate the mass fraction of the yield of the ester formed when 32 g of acetic acid and 50 g of propanol-2 are heated in the presence of concentrated sulfuric acid, if 24 g of the ester is formed.

9. For the hydrolysis of a fat sample weighing 221 g, it took 150 g of sodium hydroxide solution with a mass fraction of alkali of 0.2. Suggest the structural formula of the original fat.

10. Calculate the volume of a potassium hydroxide solution with an alkali mass fraction of 0.25 and a density of 1.23 g / cm 3, which must be spent to carry out the hydrolysis of 15 g of a mixture consisting of ethanoic acid ethyl ester, methanoic acid propyl ester and propanoic acid methyl ester.

VIDEO EXPERIENCE

1. What reaction underlies the preparation of esters:
a) neutralization	b) polymerization
c) esterification	d) hydrogenation
2. How many isomeric esters correspond to the formula C 4 H 8 O 2:
a) 2

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1 Fats. Fats are esters of glycerol and higher monobasic carboxylic acids (so-called FATTY acids). The common name for such compounds is triglycerides or triacylglycerols, where the acyl residue of the carboxylic acid is C= O R Fatty acids. Limit acids: 1. Butyric acid C 3 H 7 -COOH 2. Palmitic acid C 15 H 31 - COOH 3. Stearic acid C 17 H 35 - COOH Physical properties. Unsaturated acids: 5. Oleic acid C 17 H 33 COOH (1 = bond) CH 3 (CH 2) 7 CH = CH (CH 2) 7 COOH 6. Linoleic acid C 17 H 31 COOH (2 = bonds) CH 3 - (CH 2) 4 -CH \u003d CH-CH 2 -CH \u003d CH-COOH 7. Linolenic acid C 17 H 29 COOH (3 = bonds) CH 3 CH 2 CH \u003d CHCH 2 CH \u003d CHCH 2 CH \u003d CH (CH 2 ) 4 COOH Animal fats Vegetable fats (oils) Solid, formed Liquid, formed by saturated acids, unsaturated stearic and palmitic acids. oleic, linoleic and others. Fats are soluble in organic solvents and insoluble in water.

2 CHEMICAL PROPERTIES. 1. Hydrolysis (saponification) of fats in an acidic or alkaline environment, or under the action of enzymes: a) acid hydrolysis: under the action of an acid, fats are hydrolyzed to glycerol and carboxylic acids, which were part of the fat molecule. b) alkaline hydrolysis saponification. It turns out glycerin and SALTs of carboxylic acids that were part of the fat. Acid hydrolysis Alkaline hydrolysis In an alkaline medium SOAP salts of higher fatty acids (solid sodium, liquid potassium) are formed. 2. Hydrogenation (hydrogenation) is the process of adding hydrogen to the residues of unsaturated acids that make up fat. At the same time, the remains of unsaturated acids pass into the remains of saturated ones, liquid vegetable fats turn into solid ones (margarine).

3 A quantitative characteristic of the degree of unsaturation of fats is the iodine number, which shows how many grams of iodine can be added to double bonds per 100 grams of fat. Synthetic detergents. Ordinary soap does not wash well in hard water and does not wash at all in sea water, since the calcium and magnesium ions contained in it give off higher acids water-insoluble salts: C 17 H 35 COONa + CaSO 4 (C 17 H 35 COO) 2 Ca + Na 2 SO 4 Therefore, along with soap from synthetic acids, synthetic detergents are produced from other types of raw materials, for example, from alkyl sulfates of salts of esters of higher alcohols and sulfuric acid. AT general view the formation of such salts can be represented by the equations: R-CH 2 -OH + H 2 SO 4 R-CH 2 -O-SO 2 -OH + H 2 O alcohol sulfuric acid alkylsulfuric acid R-CH 2 -O-SO 2 -OH + NaOH R-CH 2 -O-SO 2 -ONa + H 2 O alkyl sulfate These salts contain from 12 to 14 carbon atoms in the molecule and have very good detergent properties. Calcium and magnesium salts are soluble in water, and therefore such soaps are washed in hard water. Alkyl sulfates are found in many washing powders. CARBOHYDRATES Carbohydrates (sugar) organic compounds, having a similar structure and properties, the composition of most of which is reflected by the formula C x (H 2 O) y, where x, y 3. The exception is deoxyribose, which has the formula C 5 H 10 O 4. SOME IMPORTANT CARBOHYDRATES Monosaccharides Oligosaccharides Polysaccharides Glucose C 6 H 12 O 6 Fructose C 6 H 12 O 6 Ribose C 5 H 10 O 5 Deoxyribose C 5 H 10 O 4 Sucrose (disaccharide) C 12 H 22 O 11 Lactose milk sugar (disaccharide) C 12 H 22 O 11 Cellulose (C 6 H 10 O 5) n Starch (C 6 H 10 O 5) n Glycogen (C 6 H 10 O 5) n

4 Monosaccharides Monosaccharides are heterofunctional compounds, their molecules contain one carbonyl group (aldehyde or ketone) and several hydroxyl groups. GLUCOSE. Receipt. 1. Hydrolysis of starch: (C 6 H 10 O 5) n + H 2 O C 6 H 12 O 6 2. Synthesis from formaldehyde: 6H 2 C \u003d O Ca (OH) 2 C 6 H 12 O 6 The reaction was first studied by A M. Butlerov. 3. In plants, carbohydrates are formed as a result of the photosynthesis reaction from CO 2 and H 2 O: 6CO H 2 O (chlorophyll, light) C 6 H 12 O 6 + 6O 2 Chemical properties of glucose. 1. In an aqueous solution of glucose, there is a dynamic balance between two cyclic forms - α and β and a linear form:

5 2. Complex formation reaction with copper (II) hydroxide. When freshly precipitated copper (II) hydroxide interacts with monosaccharides, the hydroxide dissolves with the formation of a blue complex. 3. Glucose as aldehyde. a) silver mirror reaction. b) reaction with copper (II) hydroxide when heated. c) Glucose can be oxidized with bromine water: d) Catalytic hydrogenation of glucose - the carbonyl group is reduced to an alcohol hydroxyl, sorbitol is obtained as a six-hydric alcohol. 4. Fermentation reactions. a) alcoholic fermentation C 6 H 12 O 6 2C 2 H 5 OH + 2CO 2 ethanol b) lactic acid fermentation C 6 H 12 O 6 2CH 3 -CH (OH) -COOH lactic acid

6 c) butyric fermentation C 6 H 12 O 6 C 3 H 7 COOH + 2CO 2 + 2H 2 O butyric acid 5. Reactions for the formation of glucose esters. Glucose is able to form simple and complex esters. The substitution of the hemiacetal (glycosidic) hydroxyl occurs most easily: Ethers are called glycosides. Under more stringent conditions (for example, with CH 3 -I), alkylation is also possible at other remaining hydroxyl groups. Monosaccharides are able to form esters with both mineral and carboxylic acids, for example: Fructose is a structural isomer of glucose - keto alcohol: CH 2 - CH - CH - CH - C - CH 2 OH OH OH OH O OH A crystalline substance that is highly soluble in water sweeter than glucose. It is found in free form in honey and fruits. The chemical properties of fructose are due to the presence of ketone and five hydroxyl groups. Hydrogenation of fructose also produces SORBITOL.

7 Disaccharides. Disaccharides are carbohydrates whose molecules consist of two monosaccharide residues connected to each other by the interaction of hydroxyl groups (two hemiacetal or one hemiacetal and one alcohol). 1. Sucrose (beet or cane sugar) C 12 H 22 O 11 The sucrose molecule consists of α-glucose and β-fructose residues connected to each other. In the sucrose molecule, the glycosidic carbon atom of glucose is BOUND, so it does not form an OPEN (aldehyde) form. As a result, sucrose does not enter into the reaction of the aldehyde group with an ammonia solution of silver oxide with copper hydroxide when heated. Such disaccharides are called non-reducing, i.e. unable to oxidize. Sucrose undergoes hydrolysis with acidified water: C 12 H 22 O 11 + H 2 O C 6 H 12 O 6 (glucose) + C 6 H 12 O 6 (fructose) 2. Maltose. It is a disaccharide consisting of two residues of α-glucose, it is an intermediate in the hydrolysis of starch. α-glucose residue α-glucose residue

8 Maltose - is a reducing disaccharide and enters into reactions characteristic of aldehydes. 3. Reducing sugars also include cellobiose and lactose: Other disaccharides can also be hydrolyzed. Polysaccharides. Polysaccharides are natural high molecular weight carbohydrates, the macromolecules of which consist of monosaccharide residues. The main representatives - starch and cellulose - are built from the remains of one monosaccharide - glucose. Starch and cellulose have the same molecular formula: (C 6 H 10 O 5) n, but completely different properties. This is due to the peculiarities of their spatial structure. Starch consists of α-glucose residues, and cellulose consists of β-glucose residues, which are spatial isomers and differ only in the position of one hydroxyl group (highlighted in color):

9 Starch. Starch is a mixture of two polysaccharides built from the residues of cyclic α-glucose. It consists of: amylose (the inner part of the starch grain) 10-20% amylopectin (the shell of the starch grain) 80-90% The amylose chain includes α-glucose residues (average molecular weight) and has an unbranched structure. The amylose macromolecule is a helix, each turn of which consists of 6 units of α-glucose. Properties of starch: 1. Hydrolysis of starch: when boiled in an acidic environment, starch is successively hydrolyzed. 2. Starch does not give a silver mirror reaction and does not reduce copper (II) hydroxide. 3. Qualitative reaction for starch: blue staining with iodine solution.

10 CELLULOSE Cellulose (fiber) is the most common plant polysaccharide. Cellulose chains are built from β-glucose residues and have a linear structure. The molecular weight of cellulose is from up to 2 million. PROPERTIES OF CELLULOSE. 1. Formation of esters with nitric and acetic acids. a) nitration of cellulose. Since the cellulose link contains 3 hydroxyl groups, nitration with an excess of nitric acid may result in the formation of cellulose trinitrate, pyroxylin explosive: (C 6 H 7 O 2 (OH) 3) n + 3n HNO 3 3nH 2 O + (C 6 H 7 O 2 (ONO 2) 3) n cellulose Nitric acid cellulose trinitrate (pyroxylin) b) acylation of cellulose. When acetic anhydride acts on cellulose, an esterification reaction occurs, and OH groups 1, 2, and 3 can participate in the reaction. It turns out cellulose acetate - acetate fiber. (C 6 H 7 O 2 (OH) 3) n + 3n (CH 3 CO) 2 O 3n CH 3 -COOH + (C 6 H 7 O 2 (OSOCH 3) 3) n cellulose acetic anhydride acetic acid cellulose triacetate 2 .Cellulose hydrolysis. Cellulose, like starch, hydrolyzes in an acidic environment:

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