English synonyms

(e,e)-4-hexadienoicacid;(E,E)-Sorbic acid;2,4-Hexadienoicacid,(E,E)-;2e,4e-hexadienoicacid;4-Hexadienoicacid,(E,E)-2;2-PROPENYL ACRYLIC ACID;1,3-Pentadiene-1-carboxylic acid;2,4-HEXANEDIENOIC ACID

Related categories

Carbohydrates; Food and beverage standards; Acids; Analytical standards; Plant extracts; Carbohydrates; Sugars; Antibiotics; Food additives; Sugars (carbohydrates); Preservatives; Preservative pesticides; Feed additives; Feed Storage additives; carbonyl compounds; standard products; antiseptic and antibacterial agents; biochemical reagents; reference substances; other biochemical reagents; organic synthesis; sweeteners; biochemical reagents-carbohydrates; organic chemical raw materials;
FOOD ADDITIVES;Food and Feed Additive;Food & Feed ADDITIVES;Fatty & Aliphatic Acids, Esters, Alcohols & Derivatives;Organic acids;Antibiotics by Application;Antibiotics N-S;Preservatives and Disinfectants;Antibiotics;Antibiotics A to Z; ;Building Blocks;C6;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Fatty Acids and conjugates;Fatty Acyls;Lipids;Food additive. Traditional Chinese medicine reference substances; additives; organic chemicals; chemical raw materials; daily chemicals; chemical reagents;
Organic Building Blocks;Others;Polyunsaturated;Spectrum of Activity;Unsaturated Fatty Acids and Derivatives;

Introduction

Sorbic acid and its sodium salt can inhibit the growth of mold and have been used as a food preservative for a long time, especially at low pH values, it can act as an undissociated acid for preservatives. Sorbic acid has the characteristics that other preservatives do not have, that is, it has strong antiseptic selectivity. It can inhibit the growth of bacteria harmful to humans, but it is harmless to bacteria beneficial to humans. For example, it can inhibit the growth of cheese mold but does not Does not affect the growth of bacteria that help cheese ripen. Therefore, in the food industry, sorbic acid is widely used as a preservative for cheese, cakes and other pastries. Tests have determined that the maximum allowable amount of sorbic acid in food is 0.1%. Mainly used for mildew prevention of cheese, pickled vegetables, dried fruit, fruit juice, fruit syrup, beverage, candied fruit, bread, candy, etc. It is also used for the preservation of fish and meat products. It is also used in cosmetics, medicine, feed, etc. Industrially, it is produced by condensation and decomposition of crotonaldehyde and ketene.

Chemical properties

 White crystalline powder. Tasteless and odorless. Soluble in ethanol and ether, insoluble in water.

Use

●  Sorbic acid is currently the most widely used acid-type food preservative in the world. Under acidic conditions (pH value below 5-6), it has inhibitory effect on mold, yeast and aerobic bacteria, but it is almost ineffective on anaerobic spore-forming bacteria and Lactobacillus acidophilus. In the food industry, use concentrated fruit and vegetable juices in plastic barrels, and the dosage should not exceed 2g/kg; The maximum usage amount in ready-to-eat jellyfish lactic acid bacteria beverage is 110g/kg; the maximum usage amount in wine and fruit wine is 0.6g/kg; in glue salt protein casings, low-salt pickles, sauces, candied fruit, juice (flavored) drinks and jellies The maximum amount of use is 0.5g/kg; the maximum amount of use in fruit and vegetable preservation and carbonated beverages is 0.2g/kg; the maximum amount of use in meat, fish, eggs, and poultry products in the food industry is 0.075g/kg. In addition, it is also used in cosmetics, medicine and feed.

●  Sorbic acid is currently the most widely used food antifungal agent in the world, and it can inhibit the growth and reproduction of microorganisms. Its toxicity is only 1/4 of that of benzoic acid, and it tends to replace benzoic acid. In the food industry, it is mainly used for mildew prevention of cheese, pickled vegetables, dried fruits, fruit juices, fruit syrups, beverages, candied fruit, bread, candy, etc., and also for the preservation of fish and meat products. As a preservative, sorbic acid is also used in the pharmaceutical industry, light industrial cosmetics, flue-cured tobacco leaves, and as an insecticide. In addition, it is also used to prepare reagents; it is used as an unsaturated acid in the resin, spice and rubber industries; it is also used in feed.

●  Used in pesticide preparation and synthetic rubber industry, also used as food preservative

●  A new type of food preservative, which can effectively inhibit the growth of bacteria, molds and yeasts, has no adverse effects on food, and can participate in the metabolism of the human body. It is an internationally recognized safe food preservative and can also be used in the pharmaceutical industry, light industry, In industries such as cosmetics, it is used as an unsaturated acid, and it can also be used in industries such as resins, spices and rubber.

Production method

●   Ethylene ketone method This method is currently the most commonly used method in industrial production in the world. Acetic acid is pyrolyzed at high temperature to produce vinyl ketone, then condensed with crotonaldehyde to form polyester, and then hydrolyzed and refined to obtain the finished product. Raw material consumption quota: ketene 510kg/t, crotonaldehyde 1100kg/t. 2. Malonic acid method is obtained by condensation and decarboxylation of malonic acid and crotonaldehyde. 3. The acetone method is obtained by condensation of acetone and crotonaldehyde, followed by dehydrogenation.

●  Butadiene route
Under the catalysis of manganese acetate, butadiene and acetic acid are compressed and combined at 140°C to obtain γ-ethylene-γ-butyrolactone. Under acidic conditions at 100°C, γ-ethylene-γ-butyrolactone is hydrolyzed to obtain sorbic acid. The acetic acid vapor containing the alkyl phosphate catalyst stays in the cracking tube above 700°C for 0.3s, and the resulting gas mixture is deactivated by converting the catalyst into ammonium phosphate with ammonia gas. Cool down to -10-30°C step by step to remove water, acetic acid and acetic anhydride, etc.; ketene gas is absorbed by crotonaldehyde, and polyhexene is generated under the catalysis of boron fluoride (or zinc chloride, cobalt chloride, etc.) -4,5-β-lactone (referred to as polyester); polyester is hydrolyzed under acidic conditions, and crude sorbic acid is precipitated after cooling, and then recrystallized with 3 to 4 times the amount of 60% ethanol to obtain sorbic acid.

●  Sorbic acid can be produced by oxidation of sorbaldehyde, condensation of acetone and crotonaldehyde, and condensation of malonic acid and crotonaldehyde. However, it is currently produced by ketene at home and abroad. In addition, the butadiene route has a good development prospect due to the low cost of raw materials.
(1) Butadiene route. Under the catalysis of manganese acetate, butadiene and acetic acid are combined under compression at 140°C to obtain γ-ethylene-γ-butyrolactone, and under acidic conditions at 100°C, γ-ethylene-γ-butyrolactone is hydrolyzed to obtain sorbic acid.
(2) The ketene method. The acetic acid vapor containing the alkyl phosphate catalyst stays in the cracking tube above 700°C for 0.3s, and the resulting gas mixture is converted into ammonium phosphate by the ammonia sauce catalyst and deactivated. Gradually cool to -30- -10°C to remove water, acetic acid and acetic anhydride, etc. Ketene gas is absorbed by crotonaldehyde, and is catalyzed by boron fluoride (or zinc chloride, cobalt chloride, etc.) to generate polyhexene-4,5-β-lactone (abbreviated as polyester). Under water hydrolysis, the crude product of sorbic acid is precipitated after cooling, and then recrystallized with 3-4 times the amount of 60% ethanol to obtain sorbic acid.

●  It is obtained by reacting crotonaldehyde and acetone under the action of a catalyst at about 0°C.

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