GB986714A - A process for the preparation of keto-ethers - Google Patents

A process for the preparation of keto-ethers

Info

Publication number
GB986714A
GB986714A GB1485563A GB1485563A GB986714A GB 986714 A GB986714 A GB 986714A GB 1485563 A GB1485563 A GB 1485563A GB 1485563 A GB1485563 A GB 1485563A GB 986714 A GB986714 A GB 986714A
Authority
GB
United Kingdom
Prior art keywords
alcohol
alkenone
alcohols
primary
reactants
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
GB1485563A
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Publication of GB986714A publication Critical patent/GB986714A/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
    • C07C45/61—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
    • C07C45/67—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 isomerisation; by change of size of the carbon skeleton
    • C07C45/68—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—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 isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
    • B01J31/08—Ion-exchange resins
    • 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
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation

Landscapes

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

Abstract

Keto-ethers of formula <FORM:0986714/C2/1> where R is a substituted or unsubstituted hydrocarbon group having 1-5 carbon atoms, any substituents being non-reactive under the reaction conditions, R1 is a hydrogen atom or alkyl group, and R11 is an alkyl group, are prepared by reacting a primary alcohol ROH with an a ,b -unsaturated alkenone containing up to 10 carbon atoms and having the formula <FORM:0986714/C2/2> in the liquid phase, at a temperature of 0-100 DEG C., in the presence of a strongly basic anion exchange resin as hereinafter defined. Suitable primary alcohols are primary aliphatic alcohols, e.g. methanol, ethanol, propanol, butanol, isobutanol, pentanol, allyl alcohol, methallyl alcohol, crotyl alcohol, isocrotyl alcohol and propargyl alcohol, and alcohols containing ether and phenyl groups which are inert under the reaction conditions, e.g. benzyl alcohol, ethylene glycol monomethyl ether and ethylene glycol monoethyl ether. Examples of suitable a ,b -unsaturated alkenones are methyl vinyl ketone, 3-penten-2-one, mesityl oxide, homomesityl oxide, 3-hexen-2-one and 2-methyl-3-hepten-5-one. Equimolar amounts of alcohol and alkenone may be used, but preferably one of the reactants is used in excess. The strongly basic anion exchange resins used in the invention are those having a pKb10 of greater than 1. Synthetic resinous ion-exchange resins having phosphonium or sulphonium functions are examples of such materials. They may be used in an amount of 0.1 to 20% by weight based on the alkenone, but greater or lesser amounts may be employed. They may be employed as dispersed solids, in suspension, or as packed beds, through, or over, which the reactants are passed. The reaction may be conducted as a batch, semi-continuous or continuous process, preferably under anhydrous conditions. In the preferred embodiment of the invention, a mixture of alcohol and alkenone is passed continuously through the catalyst bed, and the ketoether is separated from the resultant mixture.
GB1485563A 1962-04-18 1963-04-16 A process for the preparation of keto-ethers Expired GB986714A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US18851762A 1962-04-18 1962-04-18

Publications (1)

Publication Number Publication Date
GB986714A true GB986714A (en) 1965-03-24

Family

ID=22693490

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1485563A Expired GB986714A (en) 1962-04-18 1963-04-16 A process for the preparation of keto-ethers

Country Status (4)

Country Link
BE (1) BE631124A (en)
DE (1) DE1253694B (en)
GB (1) GB986714A (en)
NL (1) NL291580A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4371708A (en) * 1980-06-07 1983-02-01 Bayer Aktiengesellschaft 4-Substituted 3,3-dimethyl-butan-2-ones, processes for their preparation and their use as intermediate products
US4948915A (en) * 1986-07-22 1990-08-14 Union Carbide Chemicals And Plastics Company Inc. Catalytic process for production of alkoxylated esters

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3822070A1 (en) * 1988-06-30 1990-02-08 Basf Ag METHOD FOR PRODUCING KETONES

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2477380A (en) * 1946-08-30 1949-07-26 Atlantic Refining Co Production of tertiary aliphatic alcohols

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4371708A (en) * 1980-06-07 1983-02-01 Bayer Aktiengesellschaft 4-Substituted 3,3-dimethyl-butan-2-ones, processes for their preparation and their use as intermediate products
USRE32122E (en) * 1980-06-07 1986-04-22 Bayer Aktiengesellschaft 4-substituted 3,3-dimethyl-butan-2-ones, processes for their preparation and their use as intermediate products
US4948915A (en) * 1986-07-22 1990-08-14 Union Carbide Chemicals And Plastics Company Inc. Catalytic process for production of alkoxylated esters

Also Published As

Publication number Publication date
BE631124A (en)
NL291580A (en)
DE1253694B (en) 1967-11-09

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