GB964097A - Process of preparing a carboxylic acid derivative - Google Patents

Process of preparing a carboxylic acid derivative

Info

Publication number
GB964097A
GB964097A GB4478760A GB4478760A GB964097A GB 964097 A GB964097 A GB 964097A GB 4478760 A GB4478760 A GB 4478760A GB 4478760 A GB4478760 A GB 4478760A GB 964097 A GB964097 A GB 964097A
Authority
GB
United Kingdom
Prior art keywords
acid
hcl
acrylonitrile
methyl
peroxide
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
GB4478760A
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.)
Montedison SpA
Original Assignee
Montedison SpA
Montecatini Societa Generale per lIndustria Mineraria e Chimica SpA
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 Montedison SpA, Montecatini Societa Generale per lIndustria Mineraria e Chimica SpA filed Critical Montedison SpA
Publication of GB964097A publication Critical patent/GB964097A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/31—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton

Landscapes

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

Abstract

Carboxylic acid derivatives are obtained by treating an aliphatic or alicyclic ketone peroxide with acrylonitrile or an acrylic ester of a C1- 5 alkanol and HCl or HBr in the presence of ferrous or cuprous ions, e.g. at -10 DEG C. to + 10 DEG C. The ketone peroxides are generally formulated as 1-hydroxy-hydroperoxides. The two types of reaction involved are: <FORM:0964097/C1/1> and <FORM:0964097/C1/2> where R1 is CN or COOR (R being C1- 5 alkyl) and R1 and R2 are e.g. alkyl groups; and the corresponding reactions with HBr and with other alicyclic ketone peroxides. In examples, (1), (11) cyclopentanone peroxide, acrylonitrile and HCl give HOOC(CH2)5CHClCN, which is hydrolysed and esterified to CH3OOC(CH2)5CHClCOOCH3 this is hydrolysed to the free acid, and the latter hydrogenated to suberic acid; (2), (3) and (7) methyl ethyl ketone or diethyl ketone peroxide, acrylonitrile and HCl give a -chlorovaleronitrile, which is hydrolysed to a -chlorovaleric acid; (4) methyl hexyl ketone peroxide, acrylonitrile and HCl give a product which is hydrolysed to a -chlorononanoic acid; (5) methyl heptyl ketone peroxide, acrylonitrile and HCl similarly give a -chlorodecanoic acid; (6) methyl ethyl ketone peroxide, acrylonitrile and HBr similarly give a -bromovaleric acid; (8) methyl ethyl ketone peroxide, methyl acrylate and HCl give methyl a -chlorovalerate; (9) cyclohexanone peroxide, treated as in (1), gives successively HOOC(CH2)6 CHClCN and CH3OOC(CH2)6CHClCOOCH3; (10) cyclohexanone peroxide, butyl acrylate and HCl gives the butyl ester of a -chloroazelaic acid; (12) Methyl a -chloroazelate is hydrolysed and hydrogenated to produce azelaic acid. Specifications 884,761 and 890,141 are referred to.
GB4478760A 1959-12-31 1960-12-30 Process of preparing a carboxylic acid derivative Expired GB964097A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT2184659 1959-12-31
IT84560 1960-01-18

Publications (1)

Publication Number Publication Date
GB964097A true GB964097A (en) 1964-07-15

Family

ID=26325049

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4478760A Expired GB964097A (en) 1959-12-31 1960-12-30 Process of preparing a carboxylic acid derivative

Country Status (2)

Country Link
DE (1) DE1254141B (en)
GB (1) GB964097A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2429768A1 (en) * 1978-06-26 1980-01-25 Brichima Spa PROCESS FOR THE PRODUCTION OF BIFUNCTIONAL ALIPHATIC ORGANIC COMPOUNDS
EP0009369A1 (en) * 1978-09-15 1980-04-02 Allied Corporation Preparation of muconic acid mononitriles and copper(II)-ammonia reagent therefor

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2429768A1 (en) * 1978-06-26 1980-01-25 Brichima Spa PROCESS FOR THE PRODUCTION OF BIFUNCTIONAL ALIPHATIC ORGANIC COMPOUNDS
EP0009369A1 (en) * 1978-09-15 1980-04-02 Allied Corporation Preparation of muconic acid mononitriles and copper(II)-ammonia reagent therefor

Also Published As

Publication number Publication date
DE1254141B (en) 1967-11-16

Similar Documents

Publication Publication Date Title
GB1307582A (en) Inhibition of polymerization of acrylic acids
ES8601305A1 (en) Process for preparing L- carnitine and chemical intermediates employed therein
GB964097A (en) Process of preparing a carboxylic acid derivative
ES459659A1 (en) Tanning skins using polycarboxylic acid partial esters
GB723547A (en) Esters and nitriles of alphahaloacrylic acids
GB996495A (en) Process for the production of pyrocarbonic acid esters
GB878233A (en) Improvements in or relating to penicillins
GB800565A (en) Method of producing n-alkyl-piperidine-ª‡-monocarboxylic acid amides and n-alkyl-pyrrolidine-ª‡-monocarboxylic acid amides
GB894134A (en) New active insecticidal esters of the pyrethrum type and a process for the production thereof
GB748064A (en) Substances having spasmolytic activity and method of producing the same
GB911344A (en) Iodinated 4-(4-alkoxyphenoxy) phenylpropionic acids and pharmaceutically acceptable salts thereof
GB952519A (en) Process for the production of penicillins
GB847779A (en) 2-(4-biphenylyl)-í¸-hexenoic acid esters thereof
GB910600A (en) Novel glutamine derivatives and process for the production of l-(+)-glutamine
GB988656A (en) Improvements in or relating to steroids and the manufacture thereof
GB897943A (en) Process for the manufacture and isolation of acrylic acid úe-butyl ester
GB926624A (en) New amines and process for their manufacture
JPS5231017A (en) Quaternizing process
GB1019569A (en) Esters of 1ª‡,2ª‡-methylene-í¸-androstene-3,17ª‰-diol and a process for their manufacture
GB1120454A (en) Preparation of esters of diisocyanate carboxylic acids
GB844439A (en) Novel crystalline pantothenic acid esters and a process for their production
GB917152A (en) Process for the preparation of ª--halogeno-ª--methylvaleric acid derivatives
GB856404A (en) Improved process of preparing salt-free n-acyl taurines
CA620449A (en) Method for producing l-glutamic acid from racemic glutamic acid by use of a micro-organism
GB872190A (en) A process for the manufacture of substituted 2,4-dioxo-tetrahydropyridines