GB854383A - Process for the manufacture of sorbic acid - Google Patents

Process for the manufacture of sorbic acid

Info

Publication number
GB854383A
GB854383A GB18261/57A GB1826157A GB854383A GB 854383 A GB854383 A GB 854383A GB 18261/57 A GB18261/57 A GB 18261/57A GB 1826157 A GB1826157 A GB 1826157A GB 854383 A GB854383 A GB 854383A
Authority
GB
United Kingdom
Prior art keywords
crotonaldehyde
sorbic acid
ketene
acid
reaction
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB18261/57A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hoechst AG
Original Assignee
Hoechst AG
Farbwerke Hoechst AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of GB854383A publication Critical patent/GB854383A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A condensation product is obtained by reacting ketene with crotonaldehyde at a temperature of at least 20 DEG C. in the presence of at least one cadmium, zinc, iron, nickel, mercury or cobalt salt of a fatty acid containing at least 4 and preferably not more than 18 carbon atoms. The product has a molecular weight of about 1,000 to 3,000 and is probably a polyester. The preferred temperature range for the reaction is 25-30 DEG C., although raised temperatures may be used. The product is an intermediate in the preparation of sorbic acid (see Group IV(b)). In examples, ketene is introduced into a stirred or agitated solution of crotonaldehyde in toluene containing zinc isovalerate, and the toluene and excess crotonaldehyde removed in vacuo.ALSO:Sorbic acid is prepared by a process wherein ketene is reacted with crotonaldehyde at a temperature of at least 20 DEG C. in the presence of at least one cadmium, iron, nickel, mercury, cobalt or zinc salt of a fatty acid containing at least 4 and preferably not more than 18 carbon atoms, the vaporisable compounds are distilled off, and the residue, still containing the fatty acid salt is decomposed to sorbic acid either by alkaline hydrolysis followed by heating with a strong aqueous acid, or by thermal decomposition. The catalysts are generally used in a proportion of 0,1-5% by weight, preferably 0,5-2% based on the crotonaldehyde. The condensation reaction is preferably carried out in an inert solvent or an excess of crotonaldehyde. It is often preferred to use an equimolecular quantity of ketene and crotonaldehyde in which the catalyst is dissolved, a small proportion of the crotonaldehyde acting as solvent and remaining unreacted. Preferred temperatures are 25-30 DEG C. The alkaline hydrolysis is preferably carried out at 60-100 DEG C., with a strong base. The resulting solution contains salts of unsaturated hydroxycarboxylic acids, the free acids being largely precipitated on the addition of acid. These free acids are dehydrated to sorbic acid by treating them with a strong aqueous acid preferably at 80-150 DEG C. Alternatively the ketene/crotonaldehyde condensation product, still containing the catalyst may be converted to sorbic acid by thermal decomposition, suitably at 180-220 DEG C. A catalytic amount, preferably 1-5%, of a substance having an alkaline reaction may be present. It is preferred to carry out the thermal decomposition in the presence of an inert substance boiling above 150 DEG C. and preferably above 180 DEG C. at atmospheric pressure, and by heating at 150-300 DEG C. A base compound is preferably present, generally 1-15% calculated as metal hydroxide, based upon the quantity of the ketene-crotonaldehyde reaction product. The inert diluent is suitably added in a quantity of 1-15 parts by weight per part of ketene crotonaldehyde reaction product. It is preferred to use diluents or solvents which are liquid at normal temperature and from which pure sorbic acid precipitates on cooling, and it is especially advantageous to use substances which are capable of forming azeotropic mixtures with sorbic acid. The decomposition may be effected at atmospheric, superatmospheric or, advantageously, subatmospheric pressures. If the ketene/crotonaldehyde reaction is effected in a solvent which is suitable for the thermal decomposition, the solution obtained may be directly subjected to thermal decomposition after evaporation of excess crotonaldehyde, if any, and, if desired, in the presence of an alkaline catalyst. Sorbic acid may be isolated, for example, by filtration of the distillate with an entraining agent. After conversion or distillation, more volatile solvents may be added to the mixture of sorbic acid and diluent to improve separation. Water may be used for this if the solvents are miscible with it.
GB18261/57A 1958-06-07 1957-06-07 Process for the manufacture of sorbic acid Expired GB854383A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE854383X 1958-06-07

Publications (1)

Publication Number Publication Date
GB854383A true GB854383A (en) 1960-11-16

Family

ID=6788839

Family Applications (1)

Application Number Title Priority Date Filing Date
GB18261/57A Expired GB854383A (en) 1958-06-07 1957-06-07 Process for the manufacture of sorbic acid

Country Status (1)

Country Link
GB (1) GB854383A (en)

Similar Documents

Publication Publication Date Title
US3856833A (en) Method for the production of aldehydic acids
US4133833A (en) Production of N,N-di(ethyl)-meta-toluamide from meta-toluic acid by liquid phase catalytic reaction with diethylamine
US2109929A (en) Preparation of amino acids
US2484067A (en) Production of unsaturated organic compounds
US2402873A (en) Reaction products of butadiene with hydrogen cyanide
US2498300A (en) Production of lysine
US3435074A (en) Process for producing nitrodiarylamines
GB2078748A (en) Preparation of 2-methylenealdehydes
US2638479A (en) Method for the preparation of esters of beta-oxy aldehydes
US2739158A (en) Preparation of beta-lactones
US2493637A (en) Process for the preparation of aliphatic nitriles
US3092640A (en) Processes for preparing bis
US2454047A (en) Conversion of alicyclic aldehydes
GB854383A (en) Process for the manufacture of sorbic acid
US3313843A (en) Preparation of cinnamate esters
US3211781A (en) Production of e-aminocaproic acid esters from e-aminocaprolactam
US3763230A (en) Sulfonium compounds of alpha-hydroxy-ypsilon-alkylmercaptobutyric acid
US3823160A (en) Preparation of ether adducts of n-vinyl-2-pyrrolidone
US2490385A (en) Production of aminoacetal
US4152530A (en) Process for preparing allylic alcohols from allylic halides
US2479972A (en) Monoalkamine esters of pyrrole-5-carboxylic acids
US2549457A (en) Preparation of alphamethylacrolein
US2425283A (en) Preparation of allylglycine
US2500713A (en) Monoalkamine esters of pyrrole-3-carboxylic acids
US3091641A (en) Preparation of tertiary amines