GB880406A - Production of condensation products of alcohols - Google Patents

Production of condensation products of alcohols

Info

Publication number
GB880406A
GB880406A GB27318/57A GB2731857A GB880406A GB 880406 A GB880406 A GB 880406A GB 27318/57 A GB27318/57 A GB 27318/57A GB 2731857 A GB2731857 A GB 2731857A GB 880406 A GB880406 A GB 880406A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
carbinols
ketones
hydrogen acceptor
alcohol
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
GB27318/57A
Inventor
Andrew Mclean
Leslie Ernest Addy
John Habeshaw
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.)
British Hydrocarbon Chemicals Ltd
Original Assignee
British Hydrocarbon Chemicals 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 British Hydrocarbon Chemicals Ltd filed Critical British Hydrocarbon Chemicals Ltd
Priority to GB27318/57A priority Critical patent/GB880406A/en
Publication of GB880406A publication Critical patent/GB880406A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07C45/002—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by dehydrogenation
    • 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
    • C07C29/143—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 ketones
    • C07C29/145—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 ketones 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
    • C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
    • C07C29/175—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds with simultaneous reduction of an oxo group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/02—Monohydroxylic acyclic alcohols
    • C07C31/10—Monohydroxylic acyclic alcohols containing three carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/08—Acetone
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/10—Methyl-ethyl ketone

Landscapes

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

Abstract

Higher ketones or such ketones and carbinols are prepared by dehydrogenating a lower aliphatic or cycloaliphatic monohydric secondary alcohol having not more than 6 carbon atoms in the vapour phase at an elevated temperature by contact with a supported nickel catalyst in the presence of an organic hydrogen acceptor capable of being hydrogenated under those conditions in which the aliphatic or cycloaliphatic alcohols are dehydrogenated, and recovering the higher ketones and/or carbinols from the reaction mixture. The hydrogen acceptors are compounds which apart from accepting hydrogen, otherwise take no active part in the reaction and include ethylenically and acetylenically unsaturated hydrocarbons, aromatic hydrocarbons and quinone. The proportion of hydrogen acceptor to alcohol may vary from, for example, 1:4 to 4:1. Some of the lower alcohol is converted into the corresponding lower ketone and the latter may be recovered and recycled with fresh lower alcohol feed. Dehydrogenation may be effected at 100 DEG -300 DEG C., if desired in the presence of inert diluents such as N2 or paraffins. The preferred catalyst is nickel-on-kieselguhr, pretreated with hydrogen at 200 DEG -400 DEG C. and then with steam at 150 DEG -300 DEG C. The products may be isolated by condensation followed by fractional distillation. Examples describe the dehydrogenation of isopropanol using benzene or a mixture of pentenes sometimes containing pentane, as the organic hydrogen acceptor and the higher condensation products include methyl isobutyl ketone, di-isobutyl ketone and methyl isobutyl carbinol in addition to acetone and other condensation products; comparative experiments are described using no hydrogen acceptor, the yields of higher ketones and carbinols being reduced or wherein acetone replaces the isopropanol, the produce then being mainly mesityl oxide.
GB27318/57A 1957-08-30 1957-08-30 Production of condensation products of alcohols Expired GB880406A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB27318/57A GB880406A (en) 1957-08-30 1957-08-30 Production of condensation products of alcohols

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB27318/57A GB880406A (en) 1957-08-30 1957-08-30 Production of condensation products of alcohols

Publications (1)

Publication Number Publication Date
GB880406A true GB880406A (en) 1961-10-18

Family

ID=10257635

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27318/57A Expired GB880406A (en) 1957-08-30 1957-08-30 Production of condensation products of alcohols

Country Status (1)

Country Link
GB (1) GB880406A (en)

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