GB890603A - Preparation of acetylenic alcohols - Google Patents

Preparation of acetylenic alcohols

Info

Publication number
GB890603A
GB890603A GB17599/60A GB1759960A GB890603A GB 890603 A GB890603 A GB 890603A GB 17599/60 A GB17599/60 A GB 17599/60A GB 1759960 A GB1759960 A GB 1759960A GB 890603 A GB890603 A GB 890603A
Authority
GB
United Kingdom
Prior art keywords
carbon atoms
radical
pentyn
butyn
formula
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
GB17599/60A
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.)
Airco Inc
Original Assignee
Air Reduction Co Inc
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 Air Reduction Co Inc filed Critical Air Reduction Co Inc
Publication of GB890603A publication Critical patent/GB890603A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/36Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
    • C07C29/38Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
    • C07C29/42Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing triple carbon-to-carbon bonds, e.g. with metal-alkynes
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14The ring being saturated

Landscapes

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

Abstract

Acetylenic alcohols are prepared by reacting an acetylenic hydrocarbon of formula CH­CR, in which R represents hydrogen or a hydrocarbon radical, with a catalytic quantity of an alkali metal hydroxide and an aldehyde or ketone at a temperature of at least -10 DEG C. and at superatmospheric pressure in the presence of liquid ammonia, and subsequently hydrolysing the reaction mixture. The reaction is preferably carried out at a temperature from -10 DEG C. to 60 DEG C. and a pressure of 25-800 p.s.i.g. The aldehyde or ketone preferably has the formula R1COR2 in which R1 and R2 are the same or different and each is hydrogen, an alkyl radical of 1-20 carbon atoms, a cycloalkyl radical of 3-10 carbon atoms, an aryl radical of 6-12 carbon atoms, a hydroxyalkyl radical of 1-20 carbon atoms, a hydroxycycloalkyl radical of 3-10 carbon atoms, an alkoxyalkyl radical of 2-20 carbon atoms, or an alkoxyalkyl radical of 4-20 carbon atoms, or in which R1 and R2 are joined to form together with the shared carbon atom a cycloalkyl radical of 6-12 carbon atoms. The alkali metal hydroxide used is preferably of at least 90% purity, is finely divided, i.e. of 80-100 mesh or higher, and contains less than 5% of water. The hydrolysis is preferably carried out with water in the presence of an organic solvent, e.g. an ether of formula R3OR4 in which R3 and R4 are alkyl radicals having 1-6 carbon atoms. Examples are given of the preparation of 5-methyl-1-butyn-3-ol, 3-methyl-1-pentyn-3-ol, 3,5-dimethyl-1-hexyn-3-ol, 3-ethyl-1-pentyn-3-ol 1-ethynyl-cyclohexanol-1, 3-ethyl-1-heptyn-3-ol, 3-phenyl-1-butyn-3-ol, 1-hexyn-3-ol, 1-pentyn-3-ol, isodecynol and 1-butyn-3-ol.
GB17599/60A 1959-05-20 1960-05-18 Preparation of acetylenic alcohols Expired GB890603A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH890603X 1959-05-20

Publications (1)

Publication Number Publication Date
GB890603A true GB890603A (en) 1962-03-07

Family

ID=4545726

Family Applications (1)

Application Number Title Priority Date Filing Date
GB17599/60A Expired GB890603A (en) 1959-05-20 1960-05-18 Preparation of acetylenic alcohols

Country Status (1)

Country Link
GB (1) GB890603A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3379777A (en) * 1964-04-02 1968-04-23 Hoffmann La Roche Acetylenic carbinols
WO2022114942A1 (en) * 2020-11-27 2022-06-02 Нао "Атырауский Университет Нефти И Газа Имени С.Утебаева" Octane-increasing additive for gasoline
CN115710159A (en) * 2022-12-06 2023-02-24 辽宁鑫隆科技有限公司 Method for purifying 1-ethynyl cyclohexanol by melt crystallization method

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3379777A (en) * 1964-04-02 1968-04-23 Hoffmann La Roche Acetylenic carbinols
WO2022114942A1 (en) * 2020-11-27 2022-06-02 Нао "Атырауский Университет Нефти И Газа Имени С.Утебаева" Octane-increasing additive for gasoline
CN115710159A (en) * 2022-12-06 2023-02-24 辽宁鑫隆科技有限公司 Method for purifying 1-ethynyl cyclohexanol by melt crystallization method
CN115710159B (en) * 2022-12-06 2023-11-21 辽宁鑫隆科技有限公司 Method for purifying 1-ethynyl cyclohexanol by using melt crystallization method

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