GB788969A - Preparation of saturated carbinols by the hydrogenation and hydrogenolysis of acetylenic glycols - Google Patents

Preparation of saturated carbinols by the hydrogenation and hydrogenolysis of acetylenic glycols

Info

Publication number
GB788969A
GB788969A GB742/56A GB74256A GB788969A GB 788969 A GB788969 A GB 788969A GB 742/56 A GB742/56 A GB 742/56A GB 74256 A GB74256 A GB 74256A GB 788969 A GB788969 A GB 788969A
Authority
GB
United Kingdom
Prior art keywords
diol
palladium
give
charcoal
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
GB742/56A
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 GB788969A publication Critical patent/GB788969A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C27/00—Processes involving the simultaneous production of more than one class of oxygen-containing compounds
    • C07C27/04—Processes involving the simultaneous production of more than one class of oxygen-containing compounds by reduction of oxygen-containing compounds
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)

Abstract

The invention comprises the new alcohol 4,7-dimethyldecan-4-ol It and other similar alcohols may be prepared by subjecting a glycol of formula <FORM:0788969/IV (b)/1> where R and R1 are alkyl radicals, to the action of hydrogen in the presence of a palladium catalyst in a reaction medium consisting of isopropyl alcohol, n-butyl alcohol, sec.-butyl alcohol or tert.-butyl alcohol or a mixture of two or more of these alcohols. Preferably the palladium is supported on an inert adsorbent such as activated carbon, charcoal, pumice, alumina, silica gel, kieselguhr, fuller's earth, bentonite, kaolin or barium sulphate. The reaction is preferably carried out at a pressure between 3 and 5 atmospheres and a temperature in the range 65-85 DEG C. It is desirable to flush the reaction vessel with an inert gas, such as nitrogen, before starting the process. In the examples: (a) 3,6-dimethyl-4-octyne-3,6-diol and sec.-butyl alcohol are treated with hydrogen in the presence of a palladium on charcoal catalyst to give 3,6-dimethyl-octane-3,6-diol; (b) 2,5-dimethyl-3-hexyne-2,5-diol dissolved in isopropyl alcohol is treated with hydrogen in the presence of palladium on charcoal to give 2,5-dimethylhexan-2-ol with some 2,5-dimethylhexane-2,5-diol; and (c) 4,7-dimethyl-5-decyne-4,7-diol is dissolved in tert.-butyl alcohol and treated with hydrogen in the presence of a palladium on charcoal catalyst to give 4,7-dimethyldecan-4-ol with some 4,7-dimethyldecane-4,7-diol and 4,7-dimethyldecane.ALSO:Catalyst regeneration.-The catalyst used for the hydrogenation and hydrogenolysis of aliphatic ditertiary acetylenic glycols to give the corresponding saturated alcohols and consisting of palladium which may be supported on a chemically inert adsorbent carrier (e.g. charcoal) is regenerated by digesting it with a saturated alcohol solvent at the boiling-point of the solvent. The preferred alcohols are methanol and tertiary butanol. Soap compositions.-4,7-Dimethyldecan-4-ol, may be incorporated in soaps (powdered, flaked or bar) or shampoos to give a pleasant odour.
GB742/56A 1955-01-12 1956-01-09 Preparation of saturated carbinols by the hydrogenation and hydrogenolysis of acetylenic glycols Expired GB788969A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US788969XA 1955-01-12 1955-01-12

Publications (1)

Publication Number Publication Date
GB788969A true GB788969A (en) 1958-01-08

Family

ID=22146868

Family Applications (1)

Application Number Title Priority Date Filing Date
GB742/56A Expired GB788969A (en) 1955-01-12 1956-01-09 Preparation of saturated carbinols by the hydrogenation and hydrogenolysis of acetylenic glycols

Country Status (1)

Country Link
GB (1) GB788969A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4864066A (en) * 1987-05-23 1989-09-05 Basf Aktiengesellschaft Preparation of alkanediols from alkynols
CN113070060A (en) * 2020-01-03 2021-07-06 万华化学集团股份有限公司 Catalyst for preparing isopropylbenzene by hydrogenolysis of alpha-dimethyl benzyl alcohol and preparation method and application thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4864066A (en) * 1987-05-23 1989-09-05 Basf Aktiengesellschaft Preparation of alkanediols from alkynols
CN113070060A (en) * 2020-01-03 2021-07-06 万华化学集团股份有限公司 Catalyst for preparing isopropylbenzene by hydrogenolysis of alpha-dimethyl benzyl alcohol and preparation method and application thereof

Similar Documents

Publication Publication Date Title
US20030225304A1 (en) Process for producing an ester
Rosenthal et al. Photoalkylation of cyclic acetals
Mitsui et al. The Stereoselectivity of Catalysts in Hydrogenation. I. The Catalytic Hydrogenation of 2-Cyclopentylidenecyclopentanol and 2-Benzylidene-1-tetralol
GB1268842A (en) Production of lower aliphatic mercaptans
GB788969A (en) Preparation of saturated carbinols by the hydrogenation and hydrogenolysis of acetylenic glycols
US3579593A (en) Process for preparing beta-phenylethyl alcohol
CA1098915A (en) Nitriles and method for their preparation
Nilsson et al. Formic Acid Reduction of Enamines. Scope of the Reaction
US4136119A (en) M-menthenone and process for its production
JPS585176B2 (en) 2- Halogen -1- Cyclopentadecene -1- Carboxylic acid ester
Shima et al. Studies of the Photochemical Reactions. V. The Synthesis of Dimethyldioxanylcarbinol and Dimethyl-α-tetrahydrofurylcarbinol
GB970790A (en) Process for the preparation of primary alcohols
US3527770A (en) Reductive dehalogenation of 4-halotetrahydropyrans
US2861080A (en) Process for making dioxolanes
JPS5227704A (en) Process for selective hydrogenation of compounds containing acetylenic unsaturated bonds
US3971830A (en) Process for the semihydrogenation of citral to citronellal
US3275696A (en) Process for the production of citronellol
US3906046A (en) Process for the production of 2-amino-1-butanol
ES438734A1 (en) Process for the preparation of acetoxybutanols
JPS5939838A (en) Novele norbornan derivative, its preparation and perfume composition containing the same
US3349139A (en) Preparation of cis-decalin
SU438630A1 (en) Acetylene release method
US3056840A (en) Process for the selective conversion of acrolein to propionaldehyde
SU77109A1 (en) The method of obtaining 1-furylhexanone-5
GB916774A (en) Improvements in or relating to the preparation of a mixture of glycerol and glycols