GB656740A - Improvements in the manufacture of crotonic anhydride - Google Patents

Improvements in the manufacture of crotonic anhydride

Info

Publication number
GB656740A
GB656740A GB14507/48A GB1450748A GB656740A GB 656740 A GB656740 A GB 656740A GB 14507/48 A GB14507/48 A GB 14507/48A GB 1450748 A GB1450748 A GB 1450748A GB 656740 A GB656740 A GB 656740A
Authority
GB
United Kingdom
Prior art keywords
anhydride
diluent
crotonic
acid
acetic
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
GB14507/48A
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.)
Acordis UK Ltd
Original Assignee
British Celanese 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 British Celanese Ltd filed Critical British Celanese Ltd
Publication of GB656740A publication Critical patent/GB656740A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/54Preparation of carboxylic acid anhydrides
    • C07C51/56Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation

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  • 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

Crotonic anhydride is produced by reaction between crotonic acid and acetic or propionic anhydride with the production of the corresponding saturated aliphatic acid, by a process which comprises continuously introducing crotonic acid, in admixture with an inert organic liquid diluent which forms an azeotropic mixture with said saturated aliphatic acid, into the vapour of the acetic or propionic anhydride boiling under atmospheric pressure and continuously removing a vaporous azeotropic mixture of said saturated aliphatic acid and said diluent to leave a liquid residue comprising crotonic anhydride. Suitable diluents are benzene, ethyl benzene, toluene and meta-xylene. In carrying out the process, acetic or propionic anhydride is heated to boiling in the base of a fractionating column and, when the column is filled with anhydride vapours, a mixture of crotonic acid and diluent is introduced at a point between 1/4 and 1/2 the length of the column above the base. Acetic (or propionic) acid is formed by reaction with the crotonic acid and is removed as an azeotropic mixture with the diluent from which it may be separated by water-extraction, the diluent then being dried and recirculated with more crotonic acid. The crotonic anhydride formed in the column is withdrawn from the base in liquid mixture with unreacted crotonic acid and unchanged acetic or propionic anhydride. The mixture is fractionated to separate the three components, the crotonic acid and acetic or propionic anhydride being returned to the column. The crotonic acid feed, which may be preheated, is preferably employed in the proportion of 1 part per 2.5-5.0 parts by weight of diluent and the acetic or propionic anhydride is preferably vaporized at a rate two or more times that theoretically necessary to react with the crotonic acid. Examples are given. Specification 612,790 is referred to. The Specification as open to inspection under Sect. 91 relates to the production of crotonic anhydride by reaction between crotonic acid and saturated lower aliphatic acid anhydrides in general wherein crotonic acid in admixture with an inert organic diluent is introduced into the vapour of a saturated lower aliphatic acid anhydride boiling at atmospheric pressure, the diluent and conditions employed being such that the diluent boils and its vapour is removed from the reaction zone together with the vapour of the lower aliphatic acid produced. This subject-matter does not appear in the Specification as accepted.ALSO:Crotonic anhydride is produced by reaction between crotonic acid and acetic or propionic anhydride with the production of the corresponding saturated aliphatic acid, by a process which comprises continuously introducing crotonic acid, in admixture with an inert organic liquid diluent which forms an azeotropic mixture with said saturated aliphatic acid, into the vapour of the acetic or propionic anhydride boiling under atmospheric pressure and continuously removing a vaporous azeotropic mixture of said saturated aliphatic acid and diluent to leave a liquid residue comprising crotonic anhydride. Suitable diluents are benzene, ethyl benzene, toluene and meta-xylene. In carrying out the process, acetic or propionic anhydride is heated to boiling in the base of a fractionating column and when the column is filled with anhydride vapours, a mixture of crotonic acid and diluent is introduced at a point between 1/4 and 1/2 the length of the column above the base. The acetic or propionic acid formed is removed in azeotropic mixture with the diluent and the diluent separated therefrom and recycled with further crotonic acid. The crotonic anhydride formed is removed from the column base in liquid mixture with unreacted crotonic acid and unchanged acetic or propionic anhydride; the latter two components are separated from the crotonic anhydride by fractionation and recycled to the column. Examples are given. Specification 612,790, [Group IV (b)], is referred to. The Specification as open to inspection under Sect. 91 relates to the production of crotonic anhydride by introducing crotonic acid in admixture with an inert organic diluent into the vapour of a saturated lower aliphatic acid anhydride boiling under atmospheric pressure, the diluent and conditions employed being such that the diluent boils and its vapour is removed from the reaction zone together with the vapour of the saturated lower aliphatic acid produced. This subject-matter does not appear in the Specification as accepted.
GB14507/48A 1947-05-29 1948-05-28 Improvements in the manufacture of crotonic anhydride Expired GB656740A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US656740XA 1947-05-29 1947-05-29

Publications (1)

Publication Number Publication Date
GB656740A true GB656740A (en) 1951-08-29

Family

ID=22064347

Family Applications (1)

Application Number Title Priority Date Filing Date
GB14507/48A Expired GB656740A (en) 1947-05-29 1948-05-28 Improvements in the manufacture of crotonic anhydride

Country Status (1)

Country Link
GB (1) GB656740A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5387705A (en) * 1993-08-13 1995-02-07 The Procter & Gamble Company Fatty acid anhydride process

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5387705A (en) * 1993-08-13 1995-02-07 The Procter & Gamble Company Fatty acid anhydride process

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