GB1086951A - Improvements in and relating to the production of oxygen-containing organic compounds - Google Patents

Improvements in and relating to the production of oxygen-containing organic compounds

Info

Publication number
GB1086951A
GB1086951A GB263764A GB263764A GB1086951A GB 1086951 A GB1086951 A GB 1086951A GB 263764 A GB263764 A GB 263764A GB 263764 A GB263764 A GB 263764A GB 1086951 A GB1086951 A GB 1086951A
Authority
GB
United Kingdom
Prior art keywords
aldehyde
cyclohexanol
catalyst
reaction mixture
metal compound
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
GB263764A
Inventor
Alan Lewis Crowther
Herbert George Lawley
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB263764A priority Critical patent/GB1086951A/en
Publication of GB1086951A publication Critical patent/GB1086951A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D315/00—Heterocyclic compounds containing rings having one oxygen atom as the only ring hetero atom according to more than one of groups C07D303/00 - C07D313/00
    • 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
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
    • C07C45/39—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a secondary hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/23—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups
    • C07C51/235—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of oxygen-containing groups to carboxyl groups of —CHO groups or primary alcohol groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/31—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting
    • C07C51/313—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting with molecular oxygen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Monocarboxylic acids, adipic acid and epsilon-caprolactone are made by co-oxidizing cyclohexanol and an aldehyde in the liquid phase with a gas containing molecular oxygen in the absence or presence of a catalyst comprising at least one transition metal compound in an amount of not more than 0.01% by weight metal compound based on cyclohexanol and under such conditions that the molar ratio of aldehyde to cyclohexanol in the reaction mixture at any instant does not exceed 1 : 10. Specified aldehydes are acetaldehyde, propionaldehyde, n- and iso-butyraldehyde, adipaldehyde, benzaldehyde and tolualdehydes. Up to 4 mol aldehyde per mol hexanol may be used, but the aldehyde is added gradually to the cyclohexanol to maintain the low concentration of aldehyde in the reaction mixture. It is preferred to operate at 45-135 DEG C. and to use a catalyst comprising a Co, Mn, Ni, V, Cr, Ti or Ru carboxylate. In the examples some glutaric and succinic acid and cyclohexanone are obtained as by-products.
GB263764A 1964-01-21 1964-01-21 Improvements in and relating to the production of oxygen-containing organic compounds Expired GB1086951A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB263764A GB1086951A (en) 1964-01-21 1964-01-21 Improvements in and relating to the production of oxygen-containing organic compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB263764A GB1086951A (en) 1964-01-21 1964-01-21 Improvements in and relating to the production of oxygen-containing organic compounds

Publications (1)

Publication Number Publication Date
GB1086951A true GB1086951A (en) 1967-10-11

Family

ID=9743072

Family Applications (1)

Application Number Title Priority Date Filing Date
GB263764A Expired GB1086951A (en) 1964-01-21 1964-01-21 Improvements in and relating to the production of oxygen-containing organic compounds

Country Status (1)

Country Link
GB (1) GB1086951A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0870751A1 (en) * 1997-04-10 1998-10-14 RHODIA FIBER & RESIN INTERMEDIATES Process for the oxidation of hydrocarbons, alcohols and/or ketons
FR2791667A1 (en) * 1999-03-30 2000-10-06 Rhone Poulenc Fibres Process for the direct oxidation of hydrocarbons to the corresponding carboxylic acids, alcohols or ketones by oxygen in the presence of soluble manganese and chromium catalysts
CN115057998A (en) * 2022-07-07 2022-09-16 武汉理工大学 Method for joint production of epsilon-caprolactone and poly (butylene succinate)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0870751A1 (en) * 1997-04-10 1998-10-14 RHODIA FIBER & RESIN INTERMEDIATES Process for the oxidation of hydrocarbons, alcohols and/or ketons
FR2761984A1 (en) * 1997-04-10 1998-10-16 Rhone Poulenc Fibres PROCESS FOR THE OXIDATION OF HYDROCARBONS, ALCOHOLS AND / OR KETONES
KR100467892B1 (en) * 1997-04-10 2005-03-16 로디아 폴리아미드 인터미디에이츠 Process for the oxidation of hydrocarbons, alcohols and/or ketones
FR2791667A1 (en) * 1999-03-30 2000-10-06 Rhone Poulenc Fibres Process for the direct oxidation of hydrocarbons to the corresponding carboxylic acids, alcohols or ketones by oxygen in the presence of soluble manganese and chromium catalysts
WO2000059858A1 (en) * 1999-03-30 2000-10-12 Rhodia Polyamide Intermediates Hydrocarbon, alcohol and/or ketone oxidation method
US6762319B1 (en) 1999-03-30 2004-07-13 Rhodia Polyamide Intermediates Hydrocarbon, alcohol and/or ketone oxidation method
CN115057998A (en) * 2022-07-07 2022-09-16 武汉理工大学 Method for joint production of epsilon-caprolactone and poly (butylene succinate)
CN115057998B (en) * 2022-07-07 2023-07-25 武汉理工大学 Method for jointly producing epsilon-caprolactone and polybutylene succinate

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