GB875856A - Production of higher ketones from saturated epoxides - Google Patents

Production of higher ketones from saturated epoxides

Info

Publication number
GB875856A
GB875856A GB27064/59A GB2706459A GB875856A GB 875856 A GB875856 A GB 875856A GB 27064/59 A GB27064/59 A GB 27064/59A GB 2706459 A GB2706459 A GB 2706459A GB 875856 A GB875856 A GB 875856A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
alkyl
copper
carbon atoms
cyclic ether
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
GB27064/59A
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.)
ExxonMobil Technology and Engineering Co
Original Assignee
Exxon Research and Engineering Co
Esso Research and Engineering Co
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 Exxon Research and Engineering Co, Esso Research and Engineering Co filed Critical Exxon Research and Engineering Co
Publication of GB875856A publication Critical patent/GB875856A/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
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/58—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in three-membered rings
    • 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
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • 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
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
    • 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
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/60—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in six-membered rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

Ketones are prepared by contacting 2,3-epoxybutane or a saturated epoxide whose molecule contains 5-16 carbon atoms and has its oxygen atom joined to at least one secondary carbon atom, at an isomerisation temperature of 200-500 DEG C. at a pressure of 150-350 psig. in the presence of hydrogen supplied at 0.5-6.0 hydrogen/cyclic ether molecular ratio with a catalyst consisting of copper on an activated carbon support. The C5-C16 epoxides preferably have the general formula <FORM:0875856/IV (b)/1> wherein R1 is C1-C4 alkyl, R2 is hydrogen or C1-C4 alkyl or R1 and R2 together form a single polymethylene bridge of 3 or 4 carbon atoms, R3 and R4 are hydrogen or C1-C4 alkyl, and n is 0-3. The catalysts may contain 0.01-20% weight of copper and may be used in a fixed or fluid bed. The cyclic ether/catalyst space velocity is preferably from 0.1 to 2.5 V/hr./V. In an example 2,5-dimethyltetrahydrofuran is isomerised to 2-hexanone. Specification 798,838 is referred to.
GB27064/59A 1958-11-06 1959-08-07 Production of higher ketones from saturated epoxides Expired GB875856A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US875856XA 1958-11-06 1958-11-06

Publications (1)

Publication Number Publication Date
GB875856A true GB875856A (en) 1961-08-23

Family

ID=22206070

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27064/59A Expired GB875856A (en) 1958-11-06 1959-08-07 Production of higher ketones from saturated epoxides

Country Status (3)

Country Link
DE (1) DE1173450B (en)
FR (1) FR1238584A (en)
GB (1) GB875856A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2791978A1 (en) * 1999-04-08 2000-10-13 Ems Chemie Ag PROCESS FOR THE CONVERSION OF CIS-AND TRANS-CYCLODODECENE OXIDE TO CYCLODODECANONE

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2031200A (en) * 1929-02-05 1936-02-18 Union Carbide & Carbon Corp Process of making products including aliphatic aldehydes
GB634080A (en) * 1946-03-29 1950-03-15 John George Mackay Bremner Improvements in and relating to the hydrogenolysis of 2-alkyl substituted furans

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2791978A1 (en) * 1999-04-08 2000-10-13 Ems Chemie Ag PROCESS FOR THE CONVERSION OF CIS-AND TRANS-CYCLODODECENE OXIDE TO CYCLODODECANONE

Also Published As

Publication number Publication date
DE1173450B (en) 1964-07-09
FR1238584A (en) 1960-08-12

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