Esters of soap fats in nature. Moscow State University of Technology and Design

Esters, fats, soaps

D. Hydrohalogenation

Esters, fats, soaps

Part A. Multiple Choice Tests

1. General formula corresponding to esters:

A. RCHO B. ROH C. ROR / D. RCOOR /

2. The name of the process for obtaining esters:

A. Hydrogenation B. Aromatization C. Hydration D. Esterification

3. Correct statement for esters and ethers:

A. They are homologues. B. They are isomers

B. To obtain them, sulfuric acid is used as a catalyst.

D. Belong to the same class of substances

4. The class of organic substances to which fats belong:

A. Esters B. Carboxylic acids C. Alcohols D. Carbohydrates

5. The process of converting liquid oils into solid fats is called:

A. Hydrolysis B. Hydration C. Hydrogenation

D. Hydrohalogenation

6. Substance capable of reacting with liquid fats (oils):

A. Ethanol B. Glucose C. Sodium chloride D. Potassium permanganate

7. The class of substances to which soaps belong:

A. Carboxylic acids B. Salts C. Alcohols D. Esters

8. Scheme reflecting the structure of the soap molecule:

A. −−· B. ·−−· C. −·− D. ·−·−

Symbols: −− hydrocarbon radical, hydrophilic part

9. Synthetic detergents with bioadditives are most effective at temperatures:

A. 15-20°C B. 35-40°C C. 75-80°C

D. Efficiency does not depend on temperature

10. Substance that can be a part of solid soap:

A. C 17 H 35 COONa B. C 17 H 35 COOK C. (C 17 H 35 COO) 2 Mg D. All of the listed substances

Part B. Free Answer Tasks

11 (8 points). Calculate the amount of sodium stearate contained in a 200 g bar of laundry soap with a mass fraction of sodium stearate of 70%.

12 (8 points). Write the reaction equations that can be used to carry out the following transformations:

Methane → acetylene → acetaldehyde → acetic acid → methyl acetate

13 (4 points). What are the advantages and disadvantages of SMS.

Esters are derivatives of oxo acids (both carboxylic and mineral) RkE (= O) l (OH) m, (l ≠ 0), which are formally products of substitution of hydrogen atoms of hydroxyls -OH of the acid function for a hydrocarbon residue (aliphatic, alkenyl, aromatic or heteroaromatic); are also considered as acyl derivatives of alcohols. In the IUPAC nomenclature, esters also include acyl derivatives of chalcogenide analogs of alcohols (thiols, selenols and tellurols).

They differ from ethers, in which two hydrocarbon radicals are connected by an oxygen atom (R1-O-R2).

Fats are esters of glycerol and higher monohydric carboxylic acids.

The common name for such compounds is triglycerides or triacylglycerols, where acyl is a carboxylic acid residue -C(O)R.

The composition of natural triglycerides includes residues of saturated acids (palmitic C15H31COOH, stearic C17H35COOH) and unsaturated acids (oleic C17H33COOH, linoleic C17H29COOH).

Animal fats (mutton, pork, beef, etc.), as a rule, are solids with a low melting point (fish oil is an exception). Fats consist mainly of triglycerides and saturated acids.

Fats as esters are characterized by a reverse hydrolysis reaction catalyzed by mineral acids. With the participation of alkalis, the hydrolysis of fats occurs irreversibly. The products in this case are soaps - salts of higher carboxylic acids and alkali metals.

Sodium salts are soap solids, potassium salts are liquid. The reaction of alkaline hydrolysis of fats, and in general of all esters, is also called amilennyam.

Fats are widely distributed in nature. In plants, they accumulate mainly in the nasinny, in the fetal pulp, in animal organisms - in the connective, subcutaneous and adipose tissue.

Fats are high calorie foods. Some fats contain vitamins A, D (for example, fish oil, especially cod oil), E (cotton, corn oil).

Soap history. In ancient times, hairs were smeared with oils and plowed for beauty. In the days of the complaint, the chairman was sprinkled with ashes. And then - a strange thing - the fat was easily washed off, the hair became clean, shiny. After all, ashes in combination with oils are the prototype of soap.

Soap- water-soluble washing mass (piece or thick liquid), obtained by the interaction of fats and alkalis, used either as a cosmetic product - for cleansing and skin care (toilet soap); or as a means of household chemicals - detergent (laundry soap).

Not to be confused with soap products which are made from synthetic surfactants, mainly from petroleum products (sodium lauryl sulfate), etc.

In recent years, soap as a cosmetic product of mass use has been increasingly used in liquid form. Solid soap is often used in the form of author's products. As household chemicals, the use of soap is declining every year around the world: consumers are choosing washing powders, dishwashing detergents, etc.

Chemically, the main component of solid soap is a mixture of soluble salts of higher fatty acids. Usually these are sodium, less often potassium and ammonium salts of acids such as stearic, palmitic, myristic, lauric and oleic.

One of the options chemical composition solid soap - C 17 H 35 COONa (liquid - C 17 H 35 COOK).

Additionally, the composition of the soap may contain other substances that have a detergent effect, as well as flavors and dyes and powders.

End of work -

This topic belongs to the section:

Organic chemistry

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Alkynes (otherwise acetylenic hydrocarbons) are hydrocarbons containing a triple bond between carbon atoms, forming a homologous series with the general formula CnH2n-2. Carbon atoms at t

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oxygenated compounds. Unsaturated carboxylic acids
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Ozone (from the English "O-zone" - "Oxygen zone") is a chemical element with the formula O3. Thermonuclear reaction of nitrogen decomposition: 1) N → a + zo + t; 2) o + zo

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NOBLE GASES (inert gases, rare gases), chem. elements of VIII gr. periodic systems: helium (He), neon (Ne), argon (Ar), krypton (Kr), xenon (Xe), radon (Rn). In nature they form

Esterification reactionreactions between alcohols and acids,
resulting in complex
ethers and water is released (from lat. ether -
ether). The catalysts are mineral
acids.

Hydrolysis

This reaction is reversible. Back
process - cleavage of an ester
under the action of water to form
carboxylic acid and alcohol are called
ester hydrolysis.

Specific aroma of berries, fruits and fruits

Esters are widely
common in
nature.
Specific flavor
berries, fruits and fruits
to a large extent
conditioned by
representatives of this
Esters of lower carboxylic acids
organic class
and lower monohydric alcohols
have a pleasant smell of flowers,
connections.
berries and fruits.

Waxes

Esters
fatty acids and
alcohols with long
hydrocarbon
called radicals
waxes.
For example, bee
wax contains complex
palmitic ester
acid
and myricil
alcohol
CH3(CH2)14–CO–OCH2(CH2)29CH3.

Esters. Physical properties

Esters -
liquids that have
pleasant fruity
smells.
Their density is less
water density, they
almost no
dissolve in water.
Good
soluble in alcohols.

Esters are of great practical importance

1. They are used in industry in
as solvents and intermediates
products in the synthesis of various
organic compounds.
2. Esters with a pleasant smell
used in perfumery and food
industry.
3. Esters often serve as starting materials
substances in the production of many
pharmaceutical preparations.

Fats

CH2-O-CO-R1 - esters
triatomic
I
glycerin alcohol and
CH-O-CO-R2
higher monatomic
I
CH2-O-CO-R3, carboxylic acids.
where R1, R2 and R3 are radicals (sometimes different)
fatty acids.

The common name for these compounds is triglycerides.

From the history:

For the first time
chemical
fat composition
identified in
the beginning of the past
century french
chemist Michel
Eugene Chevrel

From the history:

What is in the composition of fats
and oils included
glycerin, for the first time
found out in 1779
famous swedish
chemist
Carl Wilhelm
Scheele.

Composition of fats

Fats may contain residues
saturated and unsaturated acids,
containing an even number of atoms
carbon and unbranched carbon
skeleton.
Natural fats are usually
mixed esters, i.e. their
molecules are made up of different
carboxylic acids.

Physical properties of fats:

Fats are insoluble in water, but readily soluble in
organic solvents - benzene, hexane. (This
ability is used to clean clothes from
fat spots)
Their density is less than 1g/cm3
If at room temperature they have a solid
state of aggregation, then they are called fats, and if
liquid, then oils.
Fats have low boiling points.
With an increase in the length of the hydrocarbon radical, the temperature
fat melting increases.

Fat classification

Fats \u003d higher limiting carboxylic acids + glycerin

The fats formed
extreme
acids (butyric,
palmitic,
stearic, etc.),
have, as a rule,
solid
consistency.
These are animal fats.
origin.
beef, pork,
lamb, etc.

Fat classification:
Animal fats are mostly solid
or semi-liquid substances:
creamy
butter,
animal
fat, fish
fat, etc.

Fats = higher unsaturated carboxylic acids + glycerin

If in the composition of fat
contains remnants
unsaturated acids
(oleic and linoleic),
they represent
viscous liquids are oils.
These are: linen, hemp,
sunflower, olive,
soy, corn, etc.

Fat classification:

Vegetable fats are called oils.
These are usually liquid substances:
sunflower, olive, linseed, castor
oils, etc.

hydrogenation reaction
Liquid fats are converted into
solid by reaction
hydrogenation
(hydrogenation).
At the same time, hydrogen
joins double
connection contained in
hydrocarbon radical
oil molecules.

Chemical properties of fats

Hydrogenation of fats:
CH3
CH3
CH3

Chemical properties of fats

Hydrolysis (saponification with water and alkalis -
caustic soda or caustic potash).

Hydrogenation product of oils - hard fat
(artificial lard, lard). Margarine -
edible fat, consists of a mixture
hydrogenated oils (sunflower,
corn, cotton, etc.), animal fats,
milk and flavoring
additives (salt,
sugar, vitamins
and etc.).

Fats as esters
a reversible reaction
hydrolysis catalyzed
mineral acids. At
participation of alkalis hydrolysis
fat occurs irreversibly.
Products in this case
are soaps - salts of higher
carboxylic acids and alkaline
metals.

Sodium salts -
hard soaps,
potassium - liquid.
alkaline reaction
hydrolysis of fats, and
in general, all complex
ethers is called
also saponification.

Fats get:

Separation. It is the most
effective method of cleaning fats.
By rendering.
Hydrogenation. Hydrogenation is carried out in
special autoclaves. Used this
process for producing margarine.
Extraction or pressing.
The essence of the pressing process is
in squeezing oil from crushed seeds.

The use of fats

In medicine
Application
for food
Production
soap
Fats
Production
candles
Feed for
animals
V
Production Production
paints
perfumery
glycerin

The value of fats:

Fats are of great importance in
human life: they perform very
important functions in the body such as
as energy, protective,
construction.

Conclusion:

1. Fats are trihydric alcohol esters
glycerin and fatty acids.
2. Fats are divided into animals and
vegetable.
3. Fats are obtained by rendering,
separation, hydrogenation,
pressing or extraction.
4. Fats in the human body perform
energy, protective, construction
functions.
5. The use of fats is varied.

Task number 1

Make formulas and give names
ethers formed
1 option:
butanoic acid and
methyl alcohol;
Option 2:
methane acid and propyl
alcohol;

Answer task number 1

1 option:
O
CH3 - CH2 - CH2 - COOH + CH3-OH → CH3 - CH2 - CH2 - C
+ H 2O
butanoic acid
methanol
methyl ester \
butanoic acid O - CH3
Option 2:
O
O
//
H - C + CH3 - CH2 - CH2 - OH → H - C
+ H 2O
\
propanol
\
HE
O - CH 2 - CH2 - CH3
methane
methane propyl ether
acid
acid

Task number 2
Finish the reaction, name the resulting substances
1 option:
C5H11COOH + C4H9OH →
Option 2:
C7H13COOH + C2H5OH →

Answer task number 2

Option 1: Saratov region
Position: chemistry teacher
Additional information: site
http://kalitina.okis.ru/
mini site
http://www.nsportal.ru/kalitina-tamara-mikhailovna

"Knowledge is only knowledge when it is acquired by the efforts of one's thought, and not by memory"

Leo Tolstoy

Lesson objectives:

■ consider the composition, structure and properties of fats as a group of esters; give a concept of soaps and compare their cleaning properties with similar synthetic detergents. ■ develop the ability to use ICT, improve the ability to conduct an educational dialogue, defend one's point of view, the skills of independent work with a textbook and laboratory work. ■ to promote the development of mutual assistance, a culture of communication, to ensure the development of interest in chemistry through interesting facts, multimedia teaching aids.

Project evaluation criteria:

Project goals - 1 point

Amount of information - 1 point

Logic, consistency, accessibility - 1 point

Clear time management 1 point

Conclusions- 1 point

Fats are esters of the trihydric alcohol glycerol and higher carboxylic acids

Fats are "simple" and

General formula for fats:

"mixed". The composition of simple fats includes residues of the same acids (R "= R" = R ""), in the composition of mixed - different.

׀׀

CH 2 –O–C–R’

| O ׀׀

CH-O-C-R''

| O ׀׀

CH 2 – O – C – R‘‘‘

Common name

such compounds

triglycerides.

Fat classification

Fats

liquid fats(oils)

Solid fats

formed by unsaturated acids - oleic, linoleic, linolenic. Examples: sunflower oil, cottonseed oil, corn olive oil, etc.

educated

saturated acids - stearic, palmitic. Examples: beef, lamb, pork fat, etc.

Physical properties of fats

Fats are lighter than water, the density is in the range of 0.9-0.95 g / cm 3 N, they are insoluble in water, but highly soluble in gasoline, acetone and hexane, and this ability is used to clean grease stains from clothes. Fats are mixtures of glycerides, therefore they melt in the temperature range.

Chemical properties of fats

1) Hydrolysis of fats:

2) Alkaline hydrolysis (saponification):

3) Hydrogenation reaction:

Exercise 1

Definition of soap. Soap types.

1 point

2) What parts does soap consist of? What part dissolves in fats, what in water?

1 point

3) Explain the cleaning action of soap.

1 point

4) Synthetic detergents

1 point

Soap is sodium or potassium salts of higher carboxylic acids: palmitic, stearic, oleic, lauric. 1 point

soap

WITH 17 N 35 COOH + NaOH → C 17 N 35 COOHa + H 2 O

sodium stearate

WITH 17 N 35 COOH + KOH → C 17 N 35 COOK + H 2 O

potassium stearate

soap molecule WITH 17 N 35 COOHa consists of two parts:

1 point

WITH 17 N 35

COOHa

■ removal of dirt particles from the surface to be cleaned and

transferring them into solution .

1 point

Synthetic detergents are sodium salts of acid esters of higher alcohols and sulfuric acid.

1 point

antiresor-

Complex-

bents

educators

fragrances

alkaline

COMPOUND

electrolytes

bleaches

Stabilization

enzymes

1. Cationic surfactants - has, in addition to detergent, also a disinfectant effect.

Non-ionic surfactants form relatively little foam, and are used to prepare machine wash products.

2. Complexing agents

(Sodium tripolyphosphate) is one of the few compounds of phosphoric acid that are well soluble in water)

Interacting with the calcium and magnesium ions in the water, the phosphate ion converts them into a precipitate of the composition Ca 3 (RO 4) 2 and Mg 3 (RO 4) 2

3. bleaches - for removal of the color pollution which have remained after washing, and bleaching.

4. Fragrances - in principle, it has nothing to do with washing, but simply gives the linen a pleasant smell.

5 . Stabilizers (Carboxymethylcellulose (CMC)) acts as a foam stabilizer.

Task 2. Instructional map for performing laboratory experiments.

1. a) Investigation of the environment of solutions of toilet, laundry soap and SMS.

Using indicator paper and the pH scale of the solution, determine what medium and pH of the solution these solutions have. Make a conclusion.

b) Comparison of the washing actions of soap and SMS.

Pour a small amount of soap and SMS solutions into 2 glasses.

Lower the soiled cloth and mix. Draw conclusions.

2. Study of the medium of the SMS solution .

Add a few drops of phenolphthalein solution to the prepared solutions. If the detergent has an alkaline environment (pH > 7), it is intended for washing ________, with a neutral one (pH \u003d 6-7) - for washing __________. Heat the solution in the flame of an alcohol lamp. Make a conclusion.

A) cotton fabrics B) silk and wool products

3. Comparison of the properties of soap and SMS in hard water.

Pour 4-5 ml of water containing calcium and magnesium ions into 2 test tubes. In the first test tube, while shaking, add the soap solution drop by drop, in the second - the previously prepared solution of synthetic detergent. Assess the cleaning power of soap and SMS in hard water.