GB1161191A - Production of Adipic Acid and Hexamethylene Diamine. - Google Patents

Production of Adipic Acid and Hexamethylene Diamine.

Info

Publication number
GB1161191A
GB1161191A GB63367A GB63367A GB1161191A GB 1161191 A GB1161191 A GB 1161191A GB 63367 A GB63367 A GB 63367A GB 63367 A GB63367 A GB 63367A GB 1161191 A GB1161191 A GB 1161191A
Authority
GB
United Kingdom
Prior art keywords
cyclohexane
hexamethylene diamine
fraction
acid
adipic acid
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
GB63367A
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.)
Celanese Corp
Original Assignee
Celanese 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 Celanese Corp filed Critical Celanese Corp
Publication of GB1161191A publication Critical patent/GB1161191A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
    • C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • 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
    • B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
    • 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
    • C07C45/33—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 CHx-moieties
    • 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
    • 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
    • B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/70—Complexes comprising metals of Group VII (VIIB) as the central metal
    • B01J2531/72—Manganese
    • 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
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84—Metals of the iron group
    • B01J2531/845—Cobalt

Landscapes

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

Abstract

1,161,191. Oxidation of cyclohexane. CELANESE CORP. 5 Jan., 1967 [7 Jan., 1966], No. 633/67. Heading C2C. [Also in Division C3] In a process for the preparation of adipic acid and hexamethylene diamine by the liquid phase oxidation of cyclohexane with oxygen at 134‹ to 180‹ C. under a pressure of 100 to 1000 lb/square inch gauge in the presence of a hydrocarbon-soluble oxidation catalyst with 6-80 minutes residence time and oxygen input to yield a conversion of at least 15% of the cyclohexane to the partial oxidation products or cyclohexanol/cyclohexanone fraction and a C 6 acid fraction are separated from the crude. The cyclohexanol/cyclohexanone fraction is oxidized to adipic acid and the C 6 acid fraction esterified, hydrogenated and ammonolysed to hexamethylene diamine in a proportion of 0À85 to 2À9 moles of adipic acid per mole of hexamethylene diamine. Examples describe the use of chromium and cobalt naphthenates with conversions of 21% and 25% of cyclohexane, followed by two azeotropic distillations to remove the residual cyclohexane and the cyclohexanol/cyclohexanone and leave a C 6 residue, adipic hydroxycaproic acid.
GB63367A 1966-01-07 1967-01-05 Production of Adipic Acid and Hexamethylene Diamine. Expired GB1161191A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US51929666A 1966-01-07 1966-01-07

Publications (1)

Publication Number Publication Date
GB1161191A true GB1161191A (en) 1969-08-13

Family

ID=24067694

Family Applications (1)

Application Number Title Priority Date Filing Date
GB63367A Expired GB1161191A (en) 1966-01-07 1967-01-05 Production of Adipic Acid and Hexamethylene Diamine.

Country Status (5)

Country Link
BE (1) BE692270A (en)
DE (1) DE1543510A1 (en)
FR (1) FR1509288A (en)
GB (1) GB1161191A (en)
NL (1) NL6700231A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1471047A1 (en) * 2002-01-29 2004-10-27 Daicel Chemical Industries, Ltd. Process for producing dicarboxylic acid

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1471047A1 (en) * 2002-01-29 2004-10-27 Daicel Chemical Industries, Ltd. Process for producing dicarboxylic acid
JPWO2003064365A1 (en) * 2002-01-29 2005-05-26 ダイセル化学工業株式会社 Method for producing dicarboxylic acid
EP1471047A4 (en) * 2002-01-29 2006-05-03 Daicel Chem Process for producing dicarboxylic acid
US7728149B2 (en) 2002-01-29 2010-06-01 Daicel Chemical Industries, Ltd. Process for producing dicarboxylic acid
KR100968681B1 (en) 2002-01-29 2010-07-06 다이셀 가가꾸 고교 가부시끼가이샤 Process for producing dicarboxylic acid
JP4520151B2 (en) * 2002-01-29 2010-08-04 ダイセル化学工業株式会社 Method for producing dicarboxylic acid

Also Published As

Publication number Publication date
NL6700231A (en) 1967-07-10
BE692270A (en) 1967-07-06
FR1509288A (en) 1968-01-12
DE1543510A1 (en) 1972-03-02

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees