GB748801A - Improvements in or relating to new chemical compounds - Google Patents

Improvements in or relating to new chemical compounds

Info

Publication number
GB748801A
GB748801A GB2164853A GB2164853A GB748801A GB 748801 A GB748801 A GB 748801A GB 2164853 A GB2164853 A GB 2164853A GB 2164853 A GB2164853 A GB 2164853A GB 748801 A GB748801 A GB 748801A
Authority
GB
United Kingdom
Prior art keywords
acid
alkyl
epsilon
condensing
saponifying
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
GB2164853A
Inventor
Reginald James Taylor
William Thomas Weller
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.)
Unilever PLC
Original Assignee
Unilever PLC
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 Unilever PLC filed Critical Unilever PLC
Priority to GB2164853A priority Critical patent/GB748801A/en
Publication of GB748801A publication Critical patent/GB748801A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D315/00Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23DEDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/005Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
    • A23D7/0056Spread compositions
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/01Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/185Saturated compounds having only one carboxyl group and containing keto groups

Landscapes

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

Abstract

The invention comprises lactones of aliphatic epsilon-hydroxy saturated straight-chain carboxylic acids containing 9 to 14 carbon atoms. They may be prepared by dehydrating the appropriate acid or de-alcoholating the alkyl ester. The acid or ester may be formed by reducing the epsilon-keto acid or an alkyl ester thereof with, for example, aluminium isopropylate. The lactones may also be prepared by directly oxidizing the a -alkylcyclohexanone by use of Caro's acid or a mixture of sulphuric acid and hydrogen peroxide. In the example: cyclohexanone is condensed with butanal and the product is dehydrated by heating with oxalic acid to give butylidene cyclohexanone. This is reduced with hydrogen in the presence of palladized charcoal to give butyl cyclohexanone which is oxidized with Caro's acid and the product saponified with alcoholic KOH to give epsilon-hydroxy decanoic acid. This is lactonized in boiling benzene in the presence of p-toluenesulphonic acid. The compounds are used to impart a butter-like flavour to foodstuffs. The epsilon-keto-acids may be prepared by the following methods:-(1) By hydrogenating the condensation product of a di-alkyl ester of sodium malonic acid and adipic acid anhydride. (2) Condensing a di-ester of sodium malonic acid with an alkyl gamma-halogenated butyrate, condensing the product with an acid halide, hydrogenating, saponifying and acidifying. (3) Condensing the butyrate of (2) with an alkyl acyl-acetate, saponifying &c. (4) Condensing a dialkyl sodium malonate with a monohalogenated methyl ether, reacting with an alkyl acyl-acetate, saponifying &c. (5) The condensation product of an alkyl-acetyl acetate and an alkyl-gamma-chloro-butyrate is condensed with an acid halide, followed by reaction with ammonia and hydrolysis. (6) Condensing an adipic alkyl imide with an alkyl magnesium halide, saponifying &c. (7) Treating a 2-alkylcycloheptanedione with an alkaline solution. (8) Oxidizing an alkylcyclohexene obtained by dehydrating the alkylcyclohexanol. (9) Oxydizing an a -alkylcyclohexanone with chromic acid in sulphuric acid. (10) Replacing the halogen atom in adipic acid mono-alkyl estermonoacid halide with an alkyl group and saponifying &c. The epsilon-hydroxy acids may be prepared, in addition to the reduction of the keto-acids, by (1) condensing a 1-halogenated-4-hydroxyalkane with a dialkyl sodium malonate to form an epsilon-hydroxyalkyl malonic ester which is saponified and acidified; and (2) subjecting the oxime of an a -alkylcyclohexanone to a Beckmann conversion to form a lactam, hydrolysing to an epsilon-amino-acid and treating with nitrous acid. The a -alkylcyclohexanone may be prepared as in the example or by transforming a dialkyl pimelate into carbalkoxy-cyclohexanone which is converted via its alkyl derivative and saponification. Specification 748,764, [Group VI], is referred to.
GB2164853A 1952-08-08 1952-08-08 Improvements in or relating to new chemical compounds Expired GB748801A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2164853A GB748801A (en) 1952-08-08 1952-08-08 Improvements in or relating to new chemical compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2164853A GB748801A (en) 1952-08-08 1952-08-08 Improvements in or relating to new chemical compounds

Publications (1)

Publication Number Publication Date
GB748801A true GB748801A (en) 1956-05-09

Family

ID=10166465

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2164853A Expired GB748801A (en) 1952-08-08 1952-08-08 Improvements in or relating to new chemical compounds

Country Status (1)

Country Link
GB (1) GB748801A (en)

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