GB960894A - Preparation of carboxylic acids and derivatives thereof - Google Patents

Preparation of carboxylic acids and derivatives thereof

Info

Publication number
GB960894A
GB960894A GB2936561A GB2936561A GB960894A GB 960894 A GB960894 A GB 960894A GB 2936561 A GB2936561 A GB 2936561A GB 2936561 A GB2936561 A GB 2936561A GB 960894 A GB960894 A GB 960894A
Authority
GB
United Kingdom
Prior art keywords
group
octene
compound
anhydride
methyl
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
GB2936561A
Inventor
Donald Holroyde Hey
John Ivan George Cadogan
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.)
Distillers Co Yeast Ltd
Distillers Co Ltd
Original Assignee
Distillers Co Yeast Ltd
Distillers Co Ltd
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
Priority to NL281468D priority Critical patent/NL281468A/xx
Priority to BE621365D priority patent/BE621365A/xx
Application filed by Distillers Co Yeast Ltd, Distillers Co Ltd filed Critical Distillers Co Yeast Ltd
Priority to GB2936561A priority patent/GB960894A/en
Priority to FR905855A priority patent/FR1330454A/en
Priority to CH952462A priority patent/CH414589A/en
Publication of GB960894A publication Critical patent/GB960894A/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
    • C07C51/347—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/54—Preparation of carboxylic acid anhydrides
    • C07C51/567—Preparation of carboxylic acid anhydrides by reactions not involving carboxylic acid anhydride groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/126—Acids containing more than four carbon atoms

Landscapes

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

Abstract

Carboxylic acids, or derivatives thereof, containing an unsubstituted a -methylene group are prepared by the reaction of an unsaturated compound of the formula: <FORM:0960894/C1/1> wherein R1 and R2 are alkyl groups, or such groups containing indifferent substituents and R1 may also be hydrogen or an alkenyl group, with a compound containing a methyl group directly attached to a carboxylic acid group, or a derivative thereof, or a keto group under conditions which promote free radical formation. The main product of this reaction is the 1:1-adduct, but smaller quantities of the n:1 adduct are obtained by the addition of n molecules of the olefinic compound to one molecule of the methyl-group-containing compound. Suitable starting materials are, e.g. butene-1, decene-1 and octene-1. Other unsaturated compounds which may be used include diolefines and cycloolefines. Suitable methyl-group-containing compounds are those in which the methyl group is adjacent to, e.g. CN, COCl, CO, CO2Alk, CO2Ar, CO2H and CONH2 groups. The formation of free radicals may be initiated by catalytic agents such as organic peroxides or certain azo compounds or by exposing the reactants to ultra violet light or ionizing radiations. In preparing the 1:1 adduct the reaction is preferably carried out by adding a mixture of the unsaturated compound and free radical initiator, either alone or with a small proportion of the activated methyl compound, to a large stoichiometric excess of the latter. In examples either di-t-butyl peroxide or dibenzoyl peroxide are used as initiators in the preparation of (1) decanoic acid from acetic acid and octene-1, (2) decanoic anhydride from acetic anhydride and octene-1, (3) ethyl decanoate from ethyl acetate and octene-1, (4) decanoic nitrile from acetonitrile and octene-1, (5) caproic acid anhydride from acetic anhydride and butene-1, (6) caproic acid from acetic acid and butene-1, and (7) nonanic anhydride from acetic anhydride and heptane-1.
GB2936561A 1961-08-15 1961-08-15 Preparation of carboxylic acids and derivatives thereof Expired GB960894A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
NL281468D NL281468A (en) 1961-08-15
BE621365D BE621365A (en) 1961-08-15
GB2936561A GB960894A (en) 1961-08-15 1961-08-15 Preparation of carboxylic acids and derivatives thereof
FR905855A FR1330454A (en) 1961-08-15 1962-08-02 Preparation of long chain acids and their derivatives containing an unsubstituted alpha-methylene group
CH952462A CH414589A (en) 1961-08-15 1962-08-09 Process for the preparation of long chain acids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2936561A GB960894A (en) 1961-08-15 1961-08-15 Preparation of carboxylic acids and derivatives thereof

Publications (1)

Publication Number Publication Date
GB960894A true GB960894A (en) 1964-06-17

Family

ID=10290386

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2936561A Expired GB960894A (en) 1961-08-15 1961-08-15 Preparation of carboxylic acids and derivatives thereof

Country Status (4)

Country Link
BE (1) BE621365A (en)
CH (1) CH414589A (en)
GB (1) GB960894A (en)
NL (1) NL281468A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3689537A (en) * 1969-03-13 1972-09-05 Gen Mills Inc 3,3-dimethyl-2-norbornane propionic acid

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3308140A (en) * 1963-06-24 1967-03-07 Edward T Roe Chain substituted higher fatty acids

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3689537A (en) * 1969-03-13 1972-09-05 Gen Mills Inc 3,3-dimethyl-2-norbornane propionic acid

Also Published As

Publication number Publication date
NL281468A (en)
CH414589A (en) 1966-06-15
BE621365A (en)

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