FR2393780A1 - Stereoselective hydrogenation of cyclo:alkenol cpds. - using partially inactivated nickel catalyst, e.g. for prodn. of D-iso:menthol for use as pharmaceutical cooling ingredient - Google Patents

Stereoselective hydrogenation of cyclo:alkenol cpds. - using partially inactivated nickel catalyst, e.g. for prodn. of D-iso:menthol for use as pharmaceutical cooling ingredient

Info

Publication number
FR2393780A1
FR2393780A1 FR7717685A FR7717685A FR2393780A1 FR 2393780 A1 FR2393780 A1 FR 2393780A1 FR 7717685 A FR7717685 A FR 7717685A FR 7717685 A FR7717685 A FR 7717685A FR 2393780 A1 FR2393780 A1 FR 2393780A1
Authority
FR
France
Prior art keywords
menthol
nickel catalyst
prodn
alkenol
cpds
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.)
Withdrawn
Application number
FR7717685A
Other languages
French (fr)
Inventor
Bernard James Kane
Karen Elizabeth Irving
James Odell Bledsoe Jr
Levy Alvarez Canova
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.)
SCM Corp
Original Assignee
SCM Corp
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 SCM Corp filed Critical SCM Corp
Priority to FR7717685A priority Critical patent/FR2393780A1/en
Publication of FR2393780A1 publication Critical patent/FR2393780A1/en
Withdrawn legal-status Critical Current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
    • C07C29/17—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
    • C07C29/172—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 the obtention of a fully saturated alcohol
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J25/00—Catalysts of the Raney type
    • B01J25/02—Raney nickel
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Hydrogen atom of a cyclic unsaturated cpd. having a hydroxy gp. projecting from an asymmetric centre of the ring and an olefinic C-C double bond which when saturated, forms an additional asymmetric centre in the ring, in which the hydrogen adds to the double bond on the same side as the hydroxy gp. thus forming an optically active product. the hydrogenation is catalytic, using a nickel catalyst with a fraction of tis reactive surfaces inactivated. Used esp. in the prodn. of d-isomenthol from d-transpiperitol without the formation of d-menthol. For example hydrogenation of d-trans-piperitol with Raney nickel catalyst at 25 degrees C and 60 osig yielded 13.9% d-menthol and 86.1 d-isomenthol whereas the same process repeated with the catalyst treated with 7.5% NiCl2 yielded 2.5% d-menthol and 97.5% d-isomenthol.
FR7717685A 1977-06-09 1977-06-09 Stereoselective hydrogenation of cyclo:alkenol cpds. - using partially inactivated nickel catalyst, e.g. for prodn. of D-iso:menthol for use as pharmaceutical cooling ingredient Withdrawn FR2393780A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7717685A FR2393780A1 (en) 1977-06-09 1977-06-09 Stereoselective hydrogenation of cyclo:alkenol cpds. - using partially inactivated nickel catalyst, e.g. for prodn. of D-iso:menthol for use as pharmaceutical cooling ingredient

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7717685A FR2393780A1 (en) 1977-06-09 1977-06-09 Stereoselective hydrogenation of cyclo:alkenol cpds. - using partially inactivated nickel catalyst, e.g. for prodn. of D-iso:menthol for use as pharmaceutical cooling ingredient

Publications (1)

Publication Number Publication Date
FR2393780A1 true FR2393780A1 (en) 1979-01-05

Family

ID=9191885

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7717685A Withdrawn FR2393780A1 (en) 1977-06-09 1977-06-09 Stereoselective hydrogenation of cyclo:alkenol cpds. - using partially inactivated nickel catalyst, e.g. for prodn. of D-iso:menthol for use as pharmaceutical cooling ingredient

Country Status (1)

Country Link
FR (1) FR2393780A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2430926A1 (en) * 1978-07-12 1980-02-08 Gaf Corp PROCESS AND CATALYST FOR PRODUCING HIGH QUALITY BUTANEDIOL

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2055437A (en) * 1935-03-25 1936-09-22 Shell Dev Hydrogenation of unsaturated alcohols
US4018842A (en) * 1976-05-27 1977-04-19 Scm Corporation Selective hydrogenation of α-pinene to cis-pinane

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2055437A (en) * 1935-03-25 1936-09-22 Shell Dev Hydrogenation of unsaturated alcohols
US4018842A (en) * 1976-05-27 1977-04-19 Scm Corporation Selective hydrogenation of α-pinene to cis-pinane

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
EXBK/51 *
EXBK/68 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2430926A1 (en) * 1978-07-12 1980-02-08 Gaf Corp PROCESS AND CATALYST FOR PRODUCING HIGH QUALITY BUTANEDIOL

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Legal Events

Date Code Title Description
ST Notification of lapse