Propionic acid h2o. E280 Propionic acid

Propionic acid is a colorless, caustic liquid with a characteristic, quite pungent odor.

Physical and chemical properties of propionic acid

Propionic acid has the following chemical formula: CH 3 CH 2 COOH. At a temperature of 440 degrees Celsius it is capable of self-ignition. Mixes well in various proportions with organic solvents and water.

According to its chemical properties, propionic acid is one of the typical representatives of the class of saturated carboxylic acids. Enters Various types chemical reactions with the formation of acid halides, amides, esters and other compounds.

Preparation of propionic acid

This chemical compound was first synthesized by Johan Gottlieb in 1844 as one of the byproducts of the decomposition of sugars. Subsequently, other chemists also received it. in various ways, not realizing that they were actually the same substance. And only three years later, Jean Baptiste Dumas established this fact and gave the name to the new substance - propionic acid.

Currently, the production of propionic acid on an industrial scale is carried out by carbolizing ethylene in the presence of a nickel catalyst and water, with further oxidation of the propionic aldehyde obtained as a result of the first reaction.

Some types of bacteria produce propionic acid during their life processes. For example, as a result of enzymatic fermentation, Emmental cheese contains about 1% of this substance.

Propionic acid in products

Propionic acid has pronounced bactericidal and fungicidal properties, i.e. inhibits growth pathogenic bacteria and fungi. Therefore, many manufacturers add propionic acid to food as a preservative, called E-280.

Directly propionic acid or ammonium propionate (ammonium salt of propionic acid) is used only for the manufacture of products intended for animal nutrition. Propionic acid can only be added to products intended for humans in the form of its calcium or sodium salts (calcium propionate or sodium propionate).

In Russia it is allowed to add propionic acid to products in the following quantities:

• In rye and packaged sliced wheat bread– up to 3.0 g per kilogram;
• In pita and baked goods – up to 2.0 g per kilogram;
• In Easter cakes - up to 1.0 g per kilogram;
• In cheeses and their analogues - in accordance with the requirements of SanPiN 2.3.2.1293-03.

Propionic acid has a pronounced odor and taste. Therefore, even if they wish, food manufacturers cannot add it to their products in a concentration of more than 0.3%. Most often, this food additive is used for preserving bakery products. It can also be used to preserve whey during transportation.

Harm of propionic acid

This additive is considered practically safe for human health. These data are confirmed by the results of numerous scientific research, which indicate that in small quantities propionic acid is not mutagenic, teratogenic or otherwise dangerous to reproductive system human properties. In addition, propionic acid oxidizes very quickly in the human body and its metabolites (decomposition products) are excreted naturally.

But there is also the opinion of independent experts who believe that the food additive E-280 should be added to the list of carcinogenic substances. Therefore, if you have a hereditary predisposition to developing malignant neoplasms, then it is best for you to avoid eating foods that contain propionic acid or its salts.

For those who work with propionic acid, it is important to follow safety precautions. If concentrated propionic acid comes into contact with the skin and mucous membranes, serious burns occur. And if ingested, it leads to the formation of ulcers and wounds in the mouth, pharynx, esophagus and stomach.

Afterwards, the compound was isolated by several more scientists and only Jean-Baptiste Dumas combined the results of the experiments, proving that chemists had discovered the same substance.

While studying it, the researchers realized that the compound belongs to the carbon group. monobasic. The chain of its molecules is open.

All this is typical for those contained in oils, waxes, and fats. That's why they are called fatty.

The propionic compound has the smallest molecular weight of the group. It turns out that acid is the first among fatty acids, and that’s how its name is translated.

Protos in Greek means "first" and pion means "fat". We will not put an end to this information; we will continue the discussion.

Properties of propionic acid

Like many, propionic acid is a caustic, colorless liquid with a pungent odor. The latter is associated with sweat vapor.

The smell is reduced if the compound is mixed with water. The process proceeds easily in any proportions.

Easily propionic acid It is also miscible with organic solvents, that is, hydrocarbons.

No wonder the reagent is included in the composition. Eat propionic acid And in products nutrition. Basically, these are flour items and cheeses.

The compound is not mutagenic and therefore not dangerous to the body. IN digestive tract the substance is oxidized, breaking down into metabolites that are easily excreted in sweat and urine.

3 percent is used in food products propionic acid solutions. However, concentrated substances are not as safe.

Getting on, or mucous membranes, they cause chemical burns. Therefore, there is a set of rules governing work with the reagent. Its formula: - CH 3 CH 2 COOH.

They talked about the minimum mass of propion among fatty acids. It is equal to 74 grams per mole. The temperature regime is also noteworthy.

Propionic acid interaction with air at 440 degrees leads to spontaneous ignition of the liquid.

It can flare up, but without maintaining the combustion process, even at 54 Celsius. 141 degrees is the boiling point of the substance, and at 21 degrees the acid melts.

Chemically, the heroine is a typical representative of saturated fatty compounds of the carbon series.

Possible propionic acid reactions with amides, halides, ethers. Of the latter, for example, let's take methyl.

When interacting with it, it forms propionic acid ester, called methyl propionate.

The reaction takes place in an acidic environment. the interaction looks like this: - CH 3 CH 2 COOH + CH 3 OH -à CH 3 CH 2 COOCH 3 + H 2 O.

Amides are called functional derivatives of carbonates. In them, hydroxyl OH is replaced by an amino group NH 2.

The result of the reactions are propionic amides. If the reaction took place with a halide, the result is an acid halide.

In other words, the hydroxyl of the carboxyl group replaces the halogen - one of the elements of the 17th group.

The interactions with halides and theonyl chloride are especially clear.

Propionic acid formula also decomposes in an alkaline environment. The parent compound and alcohol are formed.

The reaction is typical for all carboxylic acids and is called their saponification. What is the name of the process of synthesis of the propionic reagent, and is it synthesized at all, or is it obtained from nature?

Extraction of propionic acid

One natural spring compounds already mentioned is oil. The second propionic plant is bacteria of the genus Propioni.

The heroine of the article is the end product of their metabolism, that is, metabolism, life activity.

Bacteria of the genus are regulars in the stomachs of ruminants. The latter, as you know, produce milk, and cheeses are made from it.

So we found out where they came from acetic propionic acid. It is also called methylacetic acid, which follows from the formula of the compound.

So, the specific smell of cheeses is the work of the “hands” of Propioni bacteria and the product of their vital activity.

However, raising cows for propionic acid or transferring oil to it is unprofitable.

Under industrial conditions, the substance is obtained by carbonylating ethylene. This is an introduction to it hydroxyl groups. The goal is achieved by the interaction of ethylene with oxide.

The second way of industrial obtaining propionic acid– purification of propionic aldehyde.

The process is catalytic, that is, it takes place in the presence of substances whose state and mass do not change after the reaction.

In the case of propionic acid production, this is either . Metal ions are used.

The third way to obtain the heroine of the article is paraphase oxidation of hydrocarbons. It occurs at a temperature of about 1000 degrees Celsius, resulting in the evaporation of phenolic waste water in the oven with excess air.

It remains to be seen whether there is an excess of propionic acid in products, whether it is used anywhere other than in Food Industry.

Applications of propionic acid

In the food industry, propionic acid is designated E280. This additive is either acid.

It helps preserve food by blocking the growth of mold and other bacteria. It turns out that the compound has antibacterial properties.

The reagent kills some fungi, therefore, it is used to combat them not only in food, but also on human skin.

IN for cosmetic purposes weak solutions acids are also used for acne.

Propionic acid derivatives Doctors also noticed. In the pharmaceutical industry, for example, Ibuprofen is made from a reagent.

This is an analgesic and anti-inflammatory drug. For rheumatism, Naproxen is prescribed - 2.6 methoxy - 2 naphthylpropine.

In the agricultural industry, propionic acid is the basis for herbicides. These are compounds that block growth and kill weeds.

You can destroy using a reagent and bad smell. Although the reagent does not smell great on its own, its aroma when surrounded by other esters is attractive.

Therefore, propionic acid is included in perfumes, deodorants, and home sprays.

Propionic acid can also be found in some plastics, as well as in most surface solvents.

Acids - chemically active compounds, destroy many metals and other materials.

It turns out that if the surface of the ribbed product is imperfect, it can be polished with a composition containing propion.

Propionic acid price

Buy propionic acid, mainly offered by German manufacturers. For a kilogram of reagent they ask for about 200 rubles.

This is the price tag of almost pure, 99.5% acid. Its anhydrous form is supplied in plastic or metal barrels of 25 and 35 kilograms.

There are products marked “analytical grade”. This is an abbreviation. Explanation: - “clean, for analysis.” That is, a compound without impurities is proposed.

For cleanliness, as they say, there is a premium. They no longer pay 200 rubles per kilo, but 250-300 rubles.

In the territory, analytical grade acid is offered mainly by Moscow and Ural enterprises.

The designation "analytical grade" can be replaced with "chemically pure". Explanation: - “chemically pure”. That is, the essence is the same, the abbreviations are different.

A reagent with impurities is called technical. This type is suitable for large-scale production of plastics, herbicides, and is used as animal feed.

There is no need to overpay for their production. Strict limits apply only to the food industry.

The law stipulates not only what acid must be used, but also how much of it must be contained in the final product.

So, theoretically, it is possible to analyze the same bread and, if the norm is too high, sue the manufacturer.

Externally define excess propionic acid in cheese or baked goods is impossible.

For most consumers, the E280 additive means nothing, but if you dig deeper, you can find out that propionic acid is hidden behind this designation. It is a colorless liquid with a pungent odor. For this chemical compound typical universal application, since it is used in cooking, in the production of plastics, in the production of herbicides, and even in pharmaceuticals.

Features of chemical bonds

If we consider this substance from a chemical point of view, then chemical formula propionic acid will be: C2H5COOH. It was derived using oil and the process of fermentation of carbohydrates. The acid itself is produced by bacteria of the same name. It is the final product of their life.

First this substance obtained from factories where vinegar is made. Acetic acid and propionic acid have become an integral concept because propionic compounds are formed during the production of vinegar.

Scientists have also proven the fact that propionic acid can also be found on skin person. In addition, it was found in the stomachs of ruminants. In the mid-19th century, its discoverer was the scientist Johan Gottlieb. He discovered the production of propionic acid in the process of decomposition of sugar, but only the Frenchman Jean-Baptiste-Dumas was able to finally reveal all the “secrets” of this substance. By the way, he gave it that name.

It is worth noting that this acid has several other names, namely:

• . propanoic acid,
• . methylacetic acid,
• . Propionic acid.

In the world classification of additives, it has the value E280.

Properties of acid

To understand why it is added to food products, plastic or animal feed, you need to know its properties. Therefore her key characteristic considered an obstacle to reproduction and growth various types mold and bacteria.

This property is valued by many manufacturers of bakery products, solvents, plastics and medicines. This chemical compound is considered a preservative.

But where and in what quantity can it be used? To answer this question you need to pay attention to legislative framework the country where propionic acid is allowed into the production process. For example, in Russian Federation this substance is considered acceptable in a certain amount, but in neighboring Ukraine, this substance is prohibited by law.

Interaction with other chemical compounds

Propionic acid reacts by mixing it with water or organic solvents. The most popular derivatives of this acid are calcium and sodium propionates. Propionates are salts and esters of propionic acid.

The most popular reactions of propionic acid are:

1. To obtain calcium propionate, perform the following reaction:

2CH3CH2COOH + CaO → (CH3CH2COO)2Ca + H2O

2. To obtain sodium propionate, it is necessary to react propionic acid with sodium hydroxide:

CH3CH2COOH + NaOH → CH3CH2COONa + H2O

The equation of propionic acid with sodium hydroxide shows that as a result of this reaction a new substance is formed - sodium propionate.

3. Also, in addition to reactions with potassium and sodium, propionic acid interacts with alcohols. The reaction of propionic acid with methyl alcohol is expressed as follows:

CH3CH2COOH + CH3OH = CH3CH2COOCH3 + H2O

The resulting substance is called methyl propionate. It is used as a flavoring agent in the food industry, and as a solvent for drying oils and cellulose.

4. Except methyl alcohol this acid reacts with ethyl alcohol. The result is propionic acid ethyl ester: CH3CH2COOC2H5. The resulting substance is widely used in the production of artificial leather, and it is also used to make solvents for plastics, cellulose, fat, and wax. This propionic acid product is considered the strongest poison for insects.

5. The frequent use of formic and propionic acid in the production of animal feed, in particular birds, requires special attention. Formic acid helps reduce the acidity level of feed, which leads to long-term storage.

6. After the reaction of ethanol with propionic acid, ethyl propionate is obtained. This substance is considered an integral part of the main types of flavorings that are added to food products. It can also be added as a fragrance in perfumes.

7. Reaction in which propanol and propionic acid participate:

O O
// H(+),t //
CH3 - C + H2O = CH3 - C + C3H7OH
\ \
O-C3H7OH

8. Reaction of ethanol with propionic acid:

C2H5OH + C2H5COOH = C2H5COOC2H5 + H2O

Harm from propionic acid

If you adhere to all safety measures and dosage of this substance, then there can be no danger. But there are cases when, due to human factor and negligence, the concentration of acid increases. In this case, the product may cause irreparable harm to the body. With increased concentrations in the body, stomach ulcers, respiratory and skin burns may appear.

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Acetic acid is formed during the fermentation of undigested carbohydrates in the colon and is quickly absorbed into the blood. Between 50 and 70% of absorbed acetic acid is absorbed by the liver—the remainder enters the peripheral circulation and is ultimately metabolized by peripheral tissues, especially muscles, as a source of energy. Acetic acid is the primary substrate for the synthesis of cholesterol, which is so necessary for neuronal and hormonal anabolism.

Propionic acid, like acetic acid, is also predominantly absorbed by the liver. However, it plays a completely different metabolic role.

Namely:
- reduces cholesterol synthesis, but at the same time reduces its metabolism so that the amount of cholesterol in the blood increases, and triglycerides also increase
- reduces the content of fatty acids in the liver and blood plasma
- increases insulin sensitivity
- reduces appetite
- used for gluconeogenesis
- is an immunosuppressant (which can be both good and bad)
- provides positive influence on inflammatory processes, increasing the threshold for inflammation in general.

Causes a feeling of satiety. A drug was created based on propionic acid. The drug is based on propionic acid, which causes a feeling of satiety and normal conditions released during the breakdown of fiber in the intestines. http://www.bbc.co.uk/russian/science/2014/12/141211_food_proprionate

Propionic acid fermentation is a continuation of lactic acid fermentation; lactic acid is fermented, the final product becomes slightly acidic.

Propionic acid bacteria:
suppress the activity of putrefactive fungi and pathogenic fungi,
form vitamins of the Viv group large quantities vitamin B12,
some strains cause growth inhibition cancer cells,
provide protection against intestinal infections.

In addition, propionic acid bacteria are not digested in the gastrointestinal tract of people and are resistant to bile acids and reduce low (pH 2.0) stomach acidity. Propionic bacteria stimulate the growth of fecal bifidobacteria and help in the treatment of bacterial dysbiosis. The main habitat of classical propionic acid bacteria is hard rennet cheeses. There is also evidence of the isolation of a number of species from soil and fermenting olives. These bacteria are often found in the stomachs of ruminants, and it is partly because of their activity that Swiss cheese gets its flavor.

Cheese making– the most ancient biotechnology using the biochemical activity of propionic bacteria. The first studies of propionic acid bacteria were related to the study of their role in the ripening of cheeses. The highest organoleptic properties and long shelf life have hard rennet cheeses with high temperature second heating, in the production of which propionic acid bacteria take part.

Strains of propionic acid bacteria of the species Propionibacterium freudenreichii widely used in the food industry for the fermentation of dairy products. Emmental cheese and other varieties of Swiss cheeses are fermented from milk in two stages: in the first, lactose and other carbohydrates in milk are fermented with the help of lactic acid bacteria into lactic acid, in the second, lactic acid with the help of propionic acid bacteria is converted into propionic acid and carbon dioxide (forming " holes" in Swiss cheese).

Their biomass contains microelements in quantities (mg/kg): Mn (267), Cu (102), Fe (535), which exceeds their content in the biomass of dairy and bifidobacteria. It has been proven that propionic acid bacteria reduce the activity of the enzymes p-glucuronidase, nitroreductase and azoreductase, under the influence of which fecal procarcinogens are converted into active forms of carcinogens. They form and accumulate NO during the reduction of nitrates and nitrites. Nitric Oxide Matters to Many vital functions, such as neurotransmission, vasodilation, intestinal motility, protection of the mucous membrane. Chronic intestinal disorders may be associated with insufficient production of NO in the body.

The antimutagenic activity of propionic acid bacteria against point mutations has been demonstrated. Considering the fact that many of the foods we eat contain varying amounts of mutagens (especially when frying food or eating moldy foods), the antimutagenic properties of propionic acid bacteria can hardly be overestimated. Propionic acid bacteria form and secrete bifidogenic metabolites that promote the growth of a number of strains of bifidobacteria. Moreover, this influence is mutual.

Studies have not found that propionic acid is toxic, mutagenic, carcinogenic or has a negative effect on the reproductive organs. In the body, propionic acid is quickly oxidized, metabolized and excreted from the body as carbon dioxide in the Krebs cycle, without accumulating in the body.

Especially a lot of propionic bacteria are formed in products that have undergone long-term fermentation in cool conditions. For example, fermentation in a cellar or refrigerator. At short term fermentation, the products will have few propionic bacteria.

1. Frequently: Consume foods containing soluble fiber and resistant starches.
2. Sometimes: fermented foods containing bacteria.
3. Don't get carried away with "lactobacillus-enriched" foods.
What foods contain fiber?

First of all, legumes, vegetables, fruits, nuts, whole grains cereal crops. Animal food contains virtually no fiber. Give preference to soluble fiber.


Products containing soluble fiber (per 100g):

• rich in pectin (1-1.1g) apples, black currants, beets
• moderate content of pectin substances (0.9-0.7 g) is found in plums, peaches, apricots, cranberries, strawberries, gooseberries;
• a small amount of pectin (0.6-0.5g) is contained in white cabbage, carrots, potatoes, pears, oranges, raspberries, grapes, lemons, watermelons;
• a small amount of pectin (0.4-0.3g) – in eggplants, onions, cucumbers, tomatoes, pumpkin, melon, tangerines, cherries, sweet cherries.

Follow simple rules:

• foods rich in fiber are unrefined, unrefined foods, the proportion of which must be increased in the daily menu;
• The longer the heat treatment, the less fiber and resistant starches there are.
• choose whole foods
• pay attention to legumes, cook them correctly.
• do not peel the fruit, it contains a lot of fiber;
• try to eat more fresh vegetables and uncooked fruits
• sometimes a chilled product is healthier than a hot one, due to more content resistant starches