GB654235A - Improvements in or relating to the preparation of beta-propiolactone - Google Patents

Improvements in or relating to the preparation of beta-propiolactone

Info

Publication number
GB654235A
GB654235A GB27807/45A GB2780745A GB654235A GB 654235 A GB654235 A GB 654235A GB 27807/45 A GB27807/45 A GB 27807/45A GB 2780745 A GB2780745 A GB 2780745A GB 654235 A GB654235 A GB 654235A
Authority
GB
United Kingdom
Prior art keywords
reaction
beta
halide
ketone
formaldehyde
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
GB27807/45A
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.)
Goodrich Corp
Original Assignee
BF Goodrich 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 BF Goodrich Corp filed Critical BF Goodrich Corp
Publication of GB654235A publication Critical patent/GB654235A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

Beta-propiolactone is obtained by reacting ketine with formaldehyde in the presence of a Friedel-Crafts halide type catalyst, the reaction being carried out in solution in beta-propiolactone as the sole solvent for the reactants. The reaction is preferably effected at below 30 DEG C. and any of the halide catalysts specified in Specification 649,028 may be employed, but the preferred catalyst is that used in Specification 654,236 which comprises a mixture of an aluminium halide with a minor proportion by weight of a zinc halide or of a zinc halide and a ferric halide. In an example, gaseous formaldehyde is carried through a heated glass tube by a flow of nitrogen and then mixed with a stream of gaseous ketene. The mixture is led into a stirred solution of aluminium chloride and zinc chloride dissolved in beta-propiolactone. The reaction is effected at 5 DEG to 20 DEG and the reaction mixture then distilled under reduced pressure. The catalyst may be destroyed before distilling by adding a small amount of alkali. Formaldehyde is obtained by heating solid paraformaldehyde by means of a salt bath maintained at 160 DEG to 210 DEG C. The Specification as open to inspection under Sect. 91 refers to the production of beta-lactones generally by effecting the reaction in a beta-lactone identical with that obtained in the reaction as the sole solvent for the reactants, and the starting materials comprise any of the ketenes and carbonyl compounds specified in Specification 649,028, as open to inspection under Sect. 91 and in addition specifies isobutyraldehyde, phenyl acetaldehyde, hexahydrobenzaldehyde, methyl n-propyl ketone, ethyl isopropyl ketone, methyl isobutyl ketone, methyl cyclohexyl ketone, and benzyl methyl ketone as starting materials. It is also stated that the higher homologues of ketene and formaldehyde need not be vaporized before introduction into the reaction mixture. This subject-matter does not appear in the Specification as accepted.
GB27807/45A 1944-10-14 1945-10-22 Improvements in or relating to the preparation of beta-propiolactone Expired GB654235A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US654235XA 1944-10-14 1944-10-14

Publications (1)

Publication Number Publication Date
GB654235A true GB654235A (en) 1951-06-13

Family

ID=22062611

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27807/45A Expired GB654235A (en) 1944-10-14 1945-10-22 Improvements in or relating to the preparation of beta-propiolactone

Country Status (1)

Country Link
GB (1) GB654235A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3221028A (en) * 1963-05-02 1965-11-30 Eastman Kodak Co Preparation of beta-lactones

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3221028A (en) * 1963-05-02 1965-11-30 Eastman Kodak Co Preparation of beta-lactones

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