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GB1480636A - Process for the manufacture of straight-chain primary alcohols and their esters - Google Patents

Process for the manufacture of straight-chain primary alcohols and their esters

Info

Publication number
GB1480636A
GB1480636A GB40615/74A GB4061574A GB1480636A GB 1480636 A GB1480636 A GB 1480636A GB 40615/74 A GB40615/74 A GB 40615/74A GB 4061574 A GB4061574 A GB 4061574A GB 1480636 A GB1480636 A GB 1480636A
Authority
GB
United Kingdom
Prior art keywords
alcohol
ester
acid
straight chain
free
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
GB40615/74A
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.)
Huels AG
Original Assignee
Chemische Werke Huels 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
Priority claimed from DE2347095A external-priority patent/DE2347095C3/en
Priority claimed from DE2423604A external-priority patent/DE2423604A1/en
Application filed by Chemische Werke Huels AG filed Critical Chemische Werke Huels AG
Publication of GB1480636A publication Critical patent/GB1480636A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/10—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond
    • C07C67/11—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with ester groups or with a carbon-halogen bond being mineral ester groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
    • C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1480636 Straight chain primary alcohols and their esters CHEMISCHE WERKE HULS AG 18 Sept 1974 [19 Sept 1973 15 May 1974] 40615/74 Heading C2C An ester of a straight chain C 6 -C 20 primary alcohol with a C 4 -C 20 monocarboxlyic acid is prepared by reacting a C 6 -C 20 straight chain 1-chloroalkane and/or 1-bromoalkane with an alkali metal salt of the monocarboxylic acid, in the presence of at least 1 mole per cent of free monocarboxylic acid relative to the alkali metal salt of the monocarboxylic acid, at a temperature of at least 150‹ C. The free acid preferably but not essentially corresponds to that forming the product ester; and alcohol for example one corresponding to that forming the ester, may also be present. The ester may then be saponified, e.g. in an alkaline medium, and the free C 6 -C 20 primary alcohol isolated; for isolation of the alcohol, a residue from an oxoalcohol or from the Alfol process, the residue being of higher boiling point and easily separated by distillation from the required alcohol, may be added to the product of saponification, the required alcohol distilled off and the residual solution of the monocarboxylic acid used for further ester formation. A mixture containing predominantly 1- chloroalkanes for use as starting material may be obtained by chlorination of one or more straight chain C 6 -C 20 paraffins, partial dehydrochlorination removal by distillation of resultant olefins, unreacted paraffins and impurities, and fractionation of the sump product to obtain the 1-chloroalkanes. 1-Bromoalkanes may be obtained by hydrobromination of α- olefins under free radical conditions, by cleavage of ethers with hydrobromic acid or by degradation of carboxylic acids or their salts. Acids used are isobutyric, caprylic, 2-ethylhexanoic, a C 8 /C 10 mixture and behenic; comparison examples using acetic and propionic acids are also given; in general the sodium salt is used, with some free acid present.
GB40615/74A 1973-09-19 1974-09-18 Process for the manufacture of straight-chain primary alcohols and their esters Expired GB1480636A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2347095A DE2347095C3 (en) 1973-09-19 1973-09-19 Process for the preparation of straight-chain primary alcohols
DE2423604A DE2423604A1 (en) 1974-05-15 1974-05-15 Straight chain prim alcohols prod from 1-chloro-or bromo-alkanes - by reaction with monocarboxylic acid salts and saponification of resulting esters

Publications (1)

Publication Number Publication Date
GB1480636A true GB1480636A (en) 1977-07-20

Family

ID=25765828

Family Applications (1)

Application Number Title Priority Date Filing Date
GB40615/74A Expired GB1480636A (en) 1973-09-19 1974-09-18 Process for the manufacture of straight-chain primary alcohols and their esters

Country Status (4)

Country Link
JP (1) JPS5053309A (en)
FR (1) FR2243921B1 (en)
GB (1) GB1480636A (en)
NL (1) NL7412355A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0444742A1 (en) * 1990-02-26 1991-09-04 Shell Internationale Researchmaatschappij B.V. Ester/alcohol synthesis

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0444742A1 (en) * 1990-02-26 1991-09-04 Shell Internationale Researchmaatschappij B.V. Ester/alcohol synthesis

Also Published As

Publication number Publication date
NL7412355A (en) 1975-03-21
FR2243921B1 (en) 1980-03-07
FR2243921A1 (en) 1975-04-11
JPS5053309A (en) 1975-05-12

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Legal Events

Date Code Title Description
429A Application made for amendment of specification (sect. 29/1949)
429H Application (made) for amendment of specification now open to opposition (sect. 29/1949)
429D Case decided by the comptroller ** specification amended (sect. 29/1949)
PS Patent sealed
SP Amendment (slips) printed
PCNP Patent ceased through non-payment of renewal fee