Learn fats:
- compound;
- classification, physical and chemical properties;
- processing;
- application;
- biological functions;
- transformation in the body.
Fats- these are esters formed by trihydric alcohol-glycerol and monobasic carboxylic acids:
CH2-O-CO-R1
CH – O -CO-R2
CH2-O-CO-R3,
where R1, R2 and R3 are radicals (sometimes different ones)
fatty acids .
During the breakdown and oxidation of fats
excreted in the body
significant amount of energy
necessary for the flow of life
important endothermic processes
maintaining
constant body temperature.
It is well known that fat performs
in a living organism the role of reserve fuel
and heat-insulating shell.
Vegetable
Palm
Animals
- butter
- animal fat
- fish fat
soluble in organic solvents
all fats are lighter than water
Michel Chevreul (1786-1889)
FATS
animals
vegetable
(excl. fish oil)
(excl. Coconut oil)
Formed by saturated acids
C 15 H 31 COOH
palmitic
C 17 H 35 COOH
stearic
Educated
Unsaturated acids
C 17 H 33 COOH
oleic
C 17 H 29 COOH
linoleic
Glycerin + acid → fat + water
Soap - these are salts, usually sodium and potassium, of higher carboxylic acids.
C 17 H 35 COONa sodium stearate
C 15 H 31 COOK potassium palmitate
Sodium salts - solid good
Potassium salts – liquid, soluble in water
Soap has special surface-
active properties (cleaning effect)
Food products
Raw materials in the production of margarine
In medicine
Soap production
In cosmetics
In technology
In varnishes and paints.
1) These salts cannot be found either in water or in the Earth, but they are available in the store and in every family.
2) Tell us what’s the matter, the gas has hardened the oil.
3) We will spread it on bread and add it to various cereals. We won’t spoil their porridge - the saying is echoed by everyone. If we add it to the cake, we will get a rich cream.
1) Soaps are salts of higher carboxylic acids.
2) Hydrogenation of fats.
Bibliography
1. Bukhtareva E.F. Merchandising of edible fats, milk and dairy products. M.: UNITY-DANA, 2005.
2. Tyutyunnikov B.N. Chemistry of fats. M.: Food Industry, 1974.
3. Shcherbakov V.G. Technology for obtaining vegetable oils. M.: Food industry, 1975.
4. Shcherbakov V.G. Chemistry and biochemistry of oil seeds. M.: Food industry, 1977.
5. Yanovaya S.M. Chemistry of fats. M.: Publishing house "NORMA", 2002.
Lesson topic: Fats Among esters, a special place is occupied by natural compounds - fats. Extracted from various sources 600 various types of fats, of which - 420 of plant origin... and more than 180 of animal origin. Fats is a mixture of esters of glycerol and higher carboxylic acids with a straight carbon chain. General formula of fats:
Slide 2
Fats are esters of trihydric alcohol glycerol and higher carboxylic acids. The general formula of fats is:
Slide 3
The composition of natural triglycerides includes residues of: Saturated acids: Palmitic - C15H31COOH Stearic - C17H35COOH Unsaturated acids: Oleic - C17H33COOH Linoleic - C17H31COOH Linolenic - C17H29COOH
Slide 4
Solid Liquid Animal fat (beef, pork, lamb, etc.), butter, lard, margarine. Vegetable oils (sunflower, corn, cottonseed, rapeseed, olive, cocoa, flaxseed, cedar, peach, sesame, poppy, castor), fish oil.
Slide 5
Thermal conductivity - conduct heat poorly. State of aggregation - solid and liquid. (there are no gaseous fats, because at high temperatures (300 ºC) fats decompose) Color - white or light yellow Odor - odorless Solubility - do not dissolve in water (lighter than water), but dissolve in fat solvents (ether, benzene, chloroform, soaps, etc.)
Slide 6
Hydrolysis of fats Hydrolysis is typical for fats, since they are esters. It is carried out under the influence of mineral acids and alkalis when heated.
Slide 7
Hydrolysis of fats in living organisms occurs under the influence of enzymes. The result of hydrolysis is the formation of glycerol and the corresponding carboxylic acids: C3H5(COO)3-R + 3H2O ↔ C3H5(OH)3 + 3RCOOH
Slide 8
Vegetable oils contain residues of unsaturated carboxylic acids, so they can undergo hydrogenation. As a result of the reaction, liquid oil turns into solid fat. This fat is called salomas, or combined fat.
Slide 9
Food products Raw materials in the production of margarine In medicine In the production of soap In cosmetics In technology In varnishes and paints
Slide 10
Application of fats
Slide 11
1) Fats belong to the class of: a) ethers; b) esters; c) polyhydric alcohols; 2) Fat hydrolysis products are aldehydes and acids; b) aromatic alcohol and acids c) glycerin and acids; 3) Fat molecules consist of residues: a) glycerol and higher monobasic carboxylic acids b) glycerol and higher dibasic acids c) ethylene glycol and dibasic acids 4) The formula of higher carboxylic acid, which cannot be part of fats: a) C15H31COOH; b) C17 H35 COOH; c) C14 H30 COOH; d) C17 H 33 COOH; 5) A substance that cannot be obtained by processing fats: a) Glycerin. b) Glucose. c) Stearic acid. d) Soap. Answer c) Answer a) Answer c) Answer b) Answer b)
slide 12
1) Indicate the formula of the ester a) b) c) d) 2) Indicate the formula of the ester a) b) c) d) 3) The name of the substance with the formula a) methyl acetate b) methyl ethanoate c) methyl ester of acetic acid d) methyl acetate d) all of the above answers are correct 4) The process of processing liquid vegetable oils into solid fats is based on the reaction of: a) hydrogenation b) hydration c) hydrolysis d) saponification Answer d) Answer c) Answer e) Answer a) View all slides
The composition and structure of fats
The composition and structure of fats was established thanks to the works of two French scientists: Chevreul and Berthelot.
The chemical composition of fats was first determined by a French chemist at the beginning of the 19th century.
Michel Eugene Chevreul by hydrolyzing them.
He found that fats consist of glycerol and carboxylic acids. However, he denied the possibility of reverse synthesis of fats from the products of their hydrolysis.
The composition and structure of fats
Fats are esters of glycerol and higher carboxylic acids.
Fat molecules contain residues of both saturated and unsaturated acids with an even number of carbon atoms and having an unbranched carbon skeleton.
CH 2 – O – CO – R 1
CH 2 – O – CO – R 2
CH 2 – O – CO – R 3
The composition of fats includes residues of not one, but different acids.
CH 2 - HE
NOOS – R 1
CH 2 – O – CO – R 1
CH 2 - HE
NOOS – R 2
CH 2 – O – CO – R 2
NOOS – R 3
CH 2 - HE
CH 2 – O – CO – R 3
3H 2 ABOUT
The general name of such compounds is triglycerides
Physical properties of fats
Solid- animal fats (excl. fish oil)
Liquid- vegetable fats (excl. coconut oil)
Formed by higher saturated acids:
Formed by higher unsaturated acids:
C 17 H 33 COOH - oleic
C 15 H 31 COOH - palmitic
C 17 H 31 COOH - linoleic
C 17 H 35 COOH - stearic
C 17 H 29 COOH - linolenic
Physical properties of fats
Physical properties of fats
Extracted from various sources 600 different types of fats,
of them - 420 plant origin...
Physical properties of fats
And more than 180 of animal origin.
Chemical properties of fats
1. Hydrolysis of fats
CH 2 – O – CO – R 1
CH 2 - HE
R 1 – UNS
CH 2 – O – CO – R 2
CH 2 - HE
R 2 – UNS
CH 2 – O – CO – R 3
CH 2 - HE
R 3 – UNS
Fats are the main source of energy for living organisms:
1 g of fat with complete oxidation (it occurs in cells with the participation of oxygen) provides 9.5 kcal (about 40 kJ) of energy, which is almost twice as much as can be obtained from proteins or carbohydrates.
Chemical properties of fats
2. Alkaline hydrolysis – saponification, heating with aqueous NaOH or alkali metal carbonates.
CH 2 – O – CO – R 1
CH 2 - HE
R 1 – COONa
CH 2 – O – CO – R 2
CH 2 - HE
R 2 – COONa
CH 2 – O – CO – R 3
CH 2 - HE
R 3 – COONa
soap
Chemical properties of fats
3. Liquid fats contain residues of unsaturated acids, which retain the properties of alkenes:
a) decolorize bromine water and a solution of potassium permanganate.
Butter also contains a small amount of unsaturated acid residues. A qualitative reaction with bromine water can distinguish natural butter from margarine.
Chemical properties of fats
b) Hydrogenation of fats
CH 2 – O – CO – C 17 N 35
CH 2 – O – CO – C 17 N 33
CH 2 – O – CO – C 17 N 35
CH 2 – O – CO – C 17 N 33
CH 2 – O – CO – C 17 N 33
CH 2 – O – CO – C 17 N 35
3H 2
trioleate
salomas
Salomas is used to produce margarine, cooking fat
Application of fats
Soap and SMS
Soaps – sodium and potassium salts of higher carboxylic acids
Soap making is one of the most ancient chemical processes in human service. Already in the 1st century, the saponification process was used to produce solid and liquid soap-like products by boiling fats with the ashes of land plants (containing potassium salts) or seaweed (containing sodium salts).
Properties of soap
WITH 17 N 35 COONa + H 2 ABOUT ↔ WITH 17 N 35 COOH + NaOH
The soap solution is alkaline.
2. Cleansing effect of soap.
Soap molecules consist of 2 parts.
The polar part - hydrophilic - is soluble in water.
Non-polar part – hydrophobic – soluble in fats and other
non-polar solvents.
Properties of soap
Properties of soap
Disadvantages of soap:
soap loses its cleaning ability because... the resulting calcium and magnesium salts of higher carboxylic acids are insoluble in water:
WITH 17 N 35 COONa + Ca 2+ → (C 17 N 35 SOO) 2 Sa ↓ + 2Na +
SMS properties
These disadvantages are absent SMS (detergents)– sodium salts of higher sulfonic acids or alkylbenzenesulfonic acids.
WITH 12 N 25 OH + H 2 SO 4 →C 12 N 25 OSO 3 H→C 12 N 25 OSO 3 Na
-N 2 ABOUT
-N 2 ABOUT
Lauryl
Lauryl sulfate
alcohol
Sodium salt
lauryl sulfate
2. Alkylbenzenesulfonates - by alkylation of benzenesulfonic acid followed by neutralization with alkali:
WITH 16 N 33 OH + C 6 N 5 SO 3 H →C 16 N 33 WITH 6 N 4 SO 3 H → C 16 N 33 WITH 6 N 4 SO 3 Na
-N 2 ABOUT
-N 2 ABOUT
Cetyl
alcohol
Cetylbenzene-
Cetylbenzene-
sulfonic acid
sodium sulfonate
SMS properties
The principle of operation of SMS is the same as that of soap. However, they have a number of advantages:
Disadvantages of SMS
Chemistry presentation on the topic: Fats. Completed by 10th grade students: Ekaterina Zadorogina, Anna Koshkina, Olga Sizonova, Irina Petrova. Contents: Determination of fats. Classification of fats. Animal fats Vegetable oils Composition of fats. Acids that make up fats. properties of fats. Chemical properties Physical properties The history of the discovery of the composition of fats and their synthesis in the laboratory. The use of fats. Definition of fats Fats are natural compounds that are esters of the trihydric alcohol glycerol and fatty acids. The common name for these compounds is triglycerides. The composition and structure of fats can be reflected by the general formula: O H2C – O – C R1 O HC – O – C R2 O H2C – O – C R3 Here R are hydrocarbon radicals, which can be either the same or different. Classification of fats. Saturated animal fats (solid) unsaturated vegetable fats (oils; liquid) Animal fats Animal fats (mainly of dense consistency) are much richer in saturated fatty acids (butyric, palmitic...) and have a high melting point. The source of animal fats is lard, lard, butter, sour cream, cream, cheeses. Vegetable oils Vegetable fats, as a rule, remain liquid under normal conditions, contain mainly unsaturated fatty acids (linoleic, linolenic, arachidonic) and have a low melting point. The source of vegetable fats are vegetable oils, nuts, soybeans, beans, oatmeal, buckwheat and others. Composition of fats. The composition of fats corresponds to the general formula: CH2-O-C(O)-R1 | CH-O-C(O)-R2 | CH2-O-C(O)-R3, where R1, R2 and R3 are radicals of (sometimes different) fatty acids. Natural fats contain three acid radicals that have an unbranched structure and, as a rule, an even number of carbon atoms (the content of “odd” acid radicals in fats is usually less than 0.1%). Acids included in fats: Myristic acid C13H27COOH Palmitic acid CH3(CH2)14COOH Stearic acid C17H35COOH Oleic acid CH3(CH2)7CH=CH(CH2)7COOH Linoleic CH3(CH2)3–(CH2CH=CH)2(CH2)7COOH. Linolenic CH3(CH2CH CH)3(CH2)7COOH Chemical properties of fats Saponification. Saponification of fats is their breakdown into free fatty acids and glycerol. For saponification, alkali solutions and metal oxides are used; this produces salts of fatty acids and glycerol: C3H5(OCOR)3 + 3NaOH = C3H5(OH)3 + 3RCOO where R is the fatty acid residue. Salts of fatty acids formed by alkali and alkaline earth metals are called soaps, and lead salts are called plasters. By shaking fatty oils with an ammonia solution, a volatile ointment is obtained - Linimentum ammoniatum; This is the same soap suspended in excess fatty oil. Rancidity. When fats are stored for a long time, a complex chemical process called rancidity occurs. The reaction occurs in the light with access to air and moisture and, probably, not without the participation of appropriate microorganisms; fats and oils are partly oxidized (by adding oxygen from the air), and partly undergo a saponification process, breaking down into glycerol and free acids. In this case, an unpleasant odor, an irritating bitter taste and an sour reaction appear. Drying of fats is a complex physical and chemical process in which, under the influence of atmospheric oxygen, their oxidation occurs, followed by condensation and polymerization. This process is associated with the presence of linoleic and linolenic acids in oils. Fats containing these acids, when spread in a thin layer, gradually turn into a transparent film, insoluble in either ether or gasoline and called oxin. Oils in which linoleic acid predominates produce soft films and are called semi-drying; oils consisting predominantly of glycerides of linolenic and isolinoleic acids form solid films and are called drying. Hydrogenation of fats is the addition of hydrogen at the site of double bonds. Fats containing unsaturated fatty acids can add two hydrogen atoms at the double bond, turning into the corresponding saturated acids. For example, oleic, linoleic and linolenic acids, when the double bonds are saturated, are converted into stearic acid. In this case, the liquid fat thickens. Our widely developed production of hydrogenated fats is based on this reaction. Hydrogenated (compacted) fats are used in the food industry in the form of margarine, and are also used in the production of ointments, pastes, and creams. Physical properties of fats. Oily to the touch; applied to paper, they give a characteristic stain. Natural fats and fatty oils are colored yellowish, less often greenish due to the presence of chlorophyll, and even less often red-orange or another color depending on the presence of certain coloring substances. Fresh fats and oils have a specific, usually pleasant, smell and taste due to the admixture of various volatile substances. All fats are lighter than water. They are completely insoluble in water, slightly soluble in alcohol (with the exception of castor oil), somewhat more soluble in boiling alcohol, and soluble in all proportions in ether, chloroform and carbon disulfide. Fats and oils are not volatile and cannot be distilled without decomposition. When heated strongly, fats begin to decompose and release the eye-irritating aldehyde acrolein, which is a decomposition product of glycerol and has a very unpleasant pungent odor. Fats and fatty oils do not ignite at ordinary temperatures, but with strong heat they can burn with a bright flame. They conduct heat and electricity poorly. The history of the discovery of the composition of fats and their synthesis in the laboratory. Elemental analysis of fats was carried out in the 19th century. A. Lavoisier In 1779, K. Scheele established that the composition of fats includes glycerin. In 1808, M. E. Chevrel established that soap is the sodium salt of a higher fatty acid. Stearic, oleic, and caproic acids were obtained for the first time. He showed that fats consist of glycerol and fatty acids, and this is not just a mixture, but a compound that, by adding water, breaks down into glycerol and acids. Chevreul, together with J. Gay-Lussac, proposed a method for producing stearin suppositories. The synthesis of fats was carried out in the 1850s by Marcelin Berthelot by heating a mixture of glycerol and fatty acids in sealed glass tubes. Phospholipids were isolated by M. Gobley in 1847, and then obtained in a purer form by F.A. Hoppe-Seyler in 1877. Use of fats. Food industry. Perfumes and cosmetics. Getting soap. SMC (synthetic detergents) Obtaining glycerin. Pharmaceuticals Production of lubricants Literature General biology 10-11, V.B. Zakharov, M. Bustard, 2002 Open lessons in chemistry VIII-XI classes / V.G. Denisova, Volgograd, 2002. Chemistry 10th grade, O.S. Gabrielyan, M. Bustard 2002 I’m going to class. Chemistry grades 10-11.M. “First of September”, 2003