GB904302A - Improvements in processes for the production of caprolactam - Google Patents

Improvements in processes for the production of caprolactam

Info

Publication number
GB904302A
GB904302A GB31957/59A GB3195759A GB904302A GB 904302 A GB904302 A GB 904302A GB 31957/59 A GB31957/59 A GB 31957/59A GB 3195759 A GB3195759 A GB 3195759A GB 904302 A GB904302 A GB 904302A
Authority
GB
United Kingdom
Prior art keywords
acid
nitrosylation
hexa
nitrosyl
benzoic 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
GB31957/59A
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.)
SNIA Viscosa SpA
Original Assignee
SNIA Viscosa SpA
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 SNIA Viscosa SpA filed Critical SNIA Viscosa SpA
Publication of GB904302A publication Critical patent/GB904302A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
    • C07D201/02—Preparation of lactams
    • C07D201/08—Preparation of lactams from carboxylic acids or derivatives thereof, e.g. hydroxy carboxylic acids, lactones or nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D223/08—Oxygen atoms
    • C07D223/10—Oxygen atoms attached in position 2

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)

Abstract

Caprolactam is prepared by reacting hexahydrobenzoic acid, or a functional derivative thereof, in the presence of free sulphuric acid having a concentration of at least 85% by weight, with a nitrosylation agent capable of providing NO+ ions in the reaction medium; free SO3 may also be present. Specified derivatives of hexa benzoic acid are the salts, esters, anhydride, chloride, nitrile and amide. Suitable nitrosylation agents are NO, N2O3, alkyl nitrites, salts of nitrons acid, nitrosyl sulphuric acid, nitrosyl sulphuric anhydride and nitrosyl chloride or bromide. Preferably, the nitrosylation agent is used in less than molar proportions relative to the hexa hydrobenzoic acid material and at least 2.5 mols of H2SO4 are used per mole of nitrosylation agent. Reaction temperatures may range from 30 DEG -200 DEG C. but lower temperatures may be used when SO3 is present. In the reaction the group attached to the tertiary carbon of the cyclo hexyl ring is split out. The free acid, salts and esters thereof yield CO2 as by-product. The reactants may be brought together in any order, if desired in continuous manner. One preferred method comprises mixing the reactants at not substantially above 50 DEG C. maintaining the mixture at a temperature at which there is no substantial evolution of CO2 until part of the NO+ ions are used up and then heating to at least 60-70 DEG C. In another method, the nitrosylation agent and H2SO4 or oleum are added to the hexa hydro benzoic acid or its derivative at an elevated temperature at which substantial evolution of CO2 occurs. In addition, a mixture of all the reactants may be fed into a heated reacted mixture of nitrosylation agent and hexa hydro benzoic acid or derivative thereof. Numerous examples are given illustrating these procedures using hexa hydro benzoic acid, its sodium or potassium salt or methyl ester and N2O3, nitrosyl sulphuric acid, nitrosyl chloride or ethyl nitrite. In some cases, the temperature is controlled by carrying out the reaction in a low boiling inert liquid under reflux, e.g. cyclohexane. The crude product is worked up by alkaline washing and solvent extraction to recover the lactam.
GB31957/59A 1959-01-28 1959-09-18 Improvements in processes for the production of caprolactam Expired GB904302A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
IT135359 1959-01-28

Publications (1)

Publication Number Publication Date
GB904302A true GB904302A (en) 1962-08-29

Family

ID=11101396

Family Applications (1)

Application Number Title Priority Date Filing Date
GB31957/59A Expired GB904302A (en) 1959-01-28 1959-09-18 Improvements in processes for the production of caprolactam

Country Status (1)

Country Link
GB (1) GB904302A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102060767B (en) * 2009-11-18 2012-08-22 中国科学院大连化学物理研究所 Method for producing caprolactam by methylbenzene

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102060767B (en) * 2009-11-18 2012-08-22 中国科学院大连化学物理研究所 Method for producing caprolactam by methylbenzene

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