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GB810913A - Improvements in or relating to the hydrogenation of acetylenic carbinols - Google Patents

Improvements in or relating to the hydrogenation of acetylenic carbinols

Info

Publication number
GB810913A
GB810913A GB22505/57A GB2250557A GB810913A GB 810913 A GB810913 A GB 810913A GB 22505/57 A GB22505/57 A GB 22505/57A GB 2250557 A GB2250557 A GB 2250557A GB 810913 A GB810913 A GB 810913A
Authority
GB
United Kingdom
Prior art keywords
methyl
hydrogenation
butyn
acetylenic
give
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
GB22505/57A
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.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche 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
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB810913A publication Critical patent/GB810913A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
    • C07C33/025—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond
    • 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
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Landscapes

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

Abstract

Ethylenic carbinols of general formula: <FORM:0810913/IV (b)/1> are obtained by hydrogenating acetylenic carbinols of general formula: <FORM:0810913/IV (b)/2> in which R1 and R2 each represent an hydrocarbon radical containing not more than 7 carbon atoms, in solution in 5 to 25 per cent of their weight of quinoline in the presence of a catalyst which selectively influences the hydrogenation of an acetylenic linkage to an ethylenic linkage. Suitable acetylenic carbinol starting materials are, for example, 2-methyl-butyn(3)-ol(2), 3-methyl-pentyn(1)-ol(3), 3-ethylpentyn (1)-ol(3), 3.5-dimethyl-hexyn(1)-ol(3) and 2-phenyl-butyn-(3)-ol(2). The preferred catalyst is 5 per cent palladium on calcium carbonate, modified by deposition of lead. The hydrogenation is preferably carried out at temperatures in the range 0-25 DEG C. and pressures not exceeding 5 p.s.i.g. In the examples: (a) 2-methyl-butyn(3)-ol(2) in solution in quinoline is hydrogenated in the presence of a palladium on calcium carbonate catalyst modified by the deposition of lead to give 2-methyl-buten(3)-ol(2); (b) 3-methyl-pentyn(1)-ol(3) is hydrogenated similarly to give 3-methyl-penten(1)-ol(3); and (c) 3.5-dimethyl-hexyn(1)-ol(3) is similarly hydrogenated to give 3.5-dimethylhexen(1)-ol(3). Specification 667,552 is referred to.
GB22505/57A 1956-07-17 1957-07-16 Improvements in or relating to the hydrogenation of acetylenic carbinols Expired GB810913A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US810913XA 1956-07-17 1956-07-17

Publications (1)

Publication Number Publication Date
GB810913A true GB810913A (en) 1959-03-25

Family

ID=22162042

Family Applications (1)

Application Number Title Priority Date Filing Date
GB22505/57A Expired GB810913A (en) 1956-07-17 1957-07-16 Improvements in or relating to the hydrogenation of acetylenic carbinols

Country Status (1)

Country Link
GB (1) GB810913A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009142642A1 (en) * 2008-05-23 2009-11-26 E. I. Du Pont De Nemours And Company High selectivity process to make dihydrofluoroalkenes
US8618339B2 (en) 2007-04-26 2013-12-31 E I Du Pont De Nemours And Company High selectivity process to make dihydrofluoroalkenes

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8618339B2 (en) 2007-04-26 2013-12-31 E I Du Pont De Nemours And Company High selectivity process to make dihydrofluoroalkenes
WO2009142642A1 (en) * 2008-05-23 2009-11-26 E. I. Du Pont De Nemours And Company High selectivity process to make dihydrofluoroalkenes

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