GB941662A - Production of adipic acid - Google Patents

Production of adipic acid

Info

Publication number
GB941662A
GB941662A GB43667/59A GB4366759A GB941662A GB 941662 A GB941662 A GB 941662A GB 43667/59 A GB43667/59 A GB 43667/59A GB 4366759 A GB4366759 A GB 4366759A GB 941662 A GB941662 A GB 941662A
Authority
GB
United Kingdom
Prior art keywords
oxidation
zone
cyclohexane
oxidation zone
cyclohexanone
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
GB43667/59A
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.)
Scientific Design Co Inc
Original Assignee
Scientific Design 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 Scientific Design Co Inc filed Critical Scientific Design Co Inc
Publication of GB941662A publication Critical patent/GB941662A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
    • C07C55/02—Dicarboxylic acids
    • C07C55/14—Adipic acid
    • 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
    • C07C29/48—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups
    • C07C29/50—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by oxidation reactions with formation of hydroxy groups with molecular oxygen only
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
    • C07C35/08—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C407/00—Preparation of peroxy compounds
    • 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
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • C07C49/403—Saturated compounds containing a keto group being part of a ring of a six-membered ring
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Abstract

Adipic acid is obtained by reacting cyclohexane with molecular oxygen in a first oxidation zone at an elevated temperature and at a pressure sufficient to maintain the cyclohexane in the liquid phase to oxidise from 3 to 20% of the cyclohexane present and to produce a mixture comprising cyclohexanone, cyclohexanol and unreacted cyclohexane, removing unreacted cyclohexane, and reacting the cyclohexanone and cyclohexanol in admixture in a weight ratio of cyclohexanone to cyclohexanol of at least 2:3 with molecular oxygen in a second oxidation zone at an elevated temperature in the presence of a metal-containing oxidation catalyst. The oxidation in the first zone is preferably carried out at about 150 DEG C. and at a pressure of 150 p.s.i.g. and the conversion of cyclohexane is preferably about 15%. The oxidation temperature in the second oxidation zone may be from 60 DEG to 105 DEG C. and the pressure may be from atmospheric to 1000 p.s.i.g. and should be sufficient to maintain a liquid phase in the oxidation zone and to maintain a partial pressure of oxygen of at least one half atmosphere. The unreacted cyclohexane from the first oxidation zone may be recycled to the first oxidation zone and the residue remaining after separating adipic acid in the second oxidation zone may be recycled to the second oxidation zone. Suitable oxidation catalysts in the second zone are compounds, e.g. the acetates, of manganese, copper, or iron, or mixture thereof. The naphthenates may also be used. The oxidation in the second zone may be carried out in the presence of a substantially inert organic medium, e.g. acetic acid, chlorobenzene, or tertiary butyl alcohol. The mixture of cyclohexanone and cyclohexanol obtained in the first oxidation zone may be used as an initiator for the oxidation of cyclohexane in the first oxidation zone. The molecular oxygen used for the oxidation may be in the form of air or other oxygen-containing gas and in an example air is used in the first zone and oxygen in the second zone.
GB43667/59A 1958-12-23 1959-12-23 Production of adipic acid Expired GB941662A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US78246158A 1958-12-23 1958-12-23

Publications (1)

Publication Number Publication Date
GB941662A true GB941662A (en) 1963-11-13

Family

ID=25126127

Family Applications (1)

Application Number Title Priority Date Filing Date
GB43667/59A Expired GB941662A (en) 1958-12-23 1959-12-23 Production of adipic acid

Country Status (4)

Country Link
CH (1) CH390894A (en)
ES (1) ES253330A1 (en)
GB (1) GB941662A (en)
SE (1) SE306728B (en)

Also Published As

Publication number Publication date
CH390894A (en) 1965-04-30
SE306728B (en) 1968-12-09
ES253330A1 (en) 1960-02-01

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