GB686247A - Manufacture of primary alcohols - Google Patents

Manufacture of primary alcohols

Info

Publication number
GB686247A
GB686247A GB152050A GB152050A GB686247A GB 686247 A GB686247 A GB 686247A GB 152050 A GB152050 A GB 152050A GB 152050 A GB152050 A GB 152050A GB 686247 A GB686247 A GB 686247A
Authority
GB
United Kingdom
Prior art keywords
isomerization
hydrogen
over
hydrogenation
pentanol
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
GB152050A
Inventor
Edward James Gasson
Alfred Frank Millidge
Ian Kenneth Miles Robson
Anthony Musgrave Wild
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
Application filed by Distillers Co Yeast Ltd, Distillers Co Ltd filed Critical Distillers Co Yeast Ltd
Priority to GB152050A priority Critical patent/GB686247A/en
Publication of GB686247A publication Critical patent/GB686247A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
    • C07C29/141—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
    • 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
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings

Landscapes

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

Abstract

Primary alcohols are made by passing an epoxide of formula <FORM:0686247/IV (b)/1> in which R1 and R2 are alkyl, aryl or alicyclic radicals, in the vapour phase at elevated temperatures over an isomerization catalyst until substantially complete conversion to the corresponding aldehyde has taken place and subsequently conducting the mixture from the isomerization step with hydrogen over a hydrogenation catalyst at elevated temperatures. Substantially complete conversion is defined as such as results in the vapours leaving the isomerization reactor having no more than 5 per cent of the initial amount of epoxide. Isomerization is preferably effected with inert gases, hydrogen being preferred since it may be used in the subsequent hydrogenation. Many epoxides are specified representative being isobutene oxide and alpha-methylstyrene oxide and the oxides of propylene dimer 2,3,4-trimethyl pentene-1 and cyclohexyl-methyl-ethylene. The reaction mixture obtained by treating alpha-di-isobutene in the liquid phase with molecular oxygen in the presence of oxidation catalysts, cf. Specification 682,067, may also be used. Alumina, expecially when activated, is the preferred isomerization catalyst and silica gel and phosphoric acid on carriers are also mentioned. Isomerization temperatures mentioned are 200-350 DEG C. and preferably the diluent gas is present in amounts to maintain the temperature at about 350 DEG C. Copper catalysts are preferred in the hydrogenation and temperatures specified are 180-350 DEG C. Hydrogen, which may be used in excess, e.g. 5-10 fold, may be recycled. In examples: (1) 1,2-epoxy-2,4,4-trimethyl pentane is passed with nitrogen over activated alumina and the pentanol obtained hydrogenated over copper on kieselguhr to the pentanol; (2) air oxidized di-isobutene is passed with hydrogen over activated alumina and the products over copper on kieselguhr to yield 2,4,4-trimethyl pentanol which is separated from methyl p neo-pentyl carbinol and ketone which are also obtained and (3) is similar to (2) save that extra hydrogen is provided for the hydrogenation.
GB152050A 1950-01-20 1950-01-20 Manufacture of primary alcohols Expired GB686247A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB152050A GB686247A (en) 1950-01-20 1950-01-20 Manufacture of primary alcohols

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB152050A GB686247A (en) 1950-01-20 1950-01-20 Manufacture of primary alcohols

Publications (1)

Publication Number Publication Date
GB686247A true GB686247A (en) 1953-01-21

Family

ID=9723392

Family Applications (1)

Application Number Title Priority Date Filing Date
GB152050A Expired GB686247A (en) 1950-01-20 1950-01-20 Manufacture of primary alcohols

Country Status (1)

Country Link
GB (1) GB686247A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0226242A1 (en) * 1985-12-03 1987-06-24 Shell Internationale Researchmaatschappij B.V. Downflow isomerization of epoxides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0226242A1 (en) * 1985-12-03 1987-06-24 Shell Internationale Researchmaatschappij B.V. Downflow isomerization of epoxides

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