GB561403A - Improvements in or relating to the manufacture of acrolein oxime and acrylonitrile - Google Patents

Improvements in or relating to the manufacture of acrolein oxime and acrylonitrile

Info

Publication number
GB561403A
GB561403A GB1608342A GB1608342A GB561403A GB 561403 A GB561403 A GB 561403A GB 1608342 A GB1608342 A GB 1608342A GB 1608342 A GB1608342 A GB 1608342A GB 561403 A GB561403 A GB 561403A
Authority
GB
United Kingdom
Prior art keywords
oxime
water
acrolein
acrylonitrile
added
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
GB1608342A
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.)
Distillers Co Yeast Ltd
Distillers Co Ltd
Original Assignee
Distillers Co Yeast Ltd
Distillers Co 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 Distillers Co Yeast Ltd, Distillers Co Ltd filed Critical Distillers Co Yeast Ltd
Priority to GB1608342A priority Critical patent/GB561403A/en
Publication of GB561403A publication Critical patent/GB561403A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/32—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
    • C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Acrolein oxime is prepared by reacting acrolein at a temperature not exceeding 50 DEG C. and at a pH of not less than 6.5 with hydroxylamine or a salt thereof. When salts of hydroxylamine, such as the hydrochloride or sulphate, are used, the required pH is maintained by the addition of bases. The oxime yields acrylonitrile by dehydration. In examples: (1) to a solution of hydroxylamine hydrochloride in water, sodium carbonate and acrolein are added with cooling; the oxime is extracted with ether; (2) the extract is treated with acetic anhydride and, after standing, water is added; by distilling, acrylonitrile is removed as an azeotrope with water; (3) the oxime is similarly obtained using calcium carbonate as the base; using a limited amount of water, the oxime separates as an oil. The process may be continuous, the reaction mixture being circulated and the oil removed as produced. The dehydration may be effected in a vertical column, water being added at the top to wash the vapours of nitrile free from acetic acid. The oxime may also be vaporized by distillation in vacuo, or by the use of an inert gaseous carrier and then passed over a dehydration catalyst such as alumina to give acrylonitrile. Acrolein prepared from formaldehyde and acetaldehyde may be used as starting material, the reaction mixture, after removal of the oxime being acidified for recovery of formaldehyde and acetaldehyde.
GB1608342A 1942-11-13 1942-11-13 Improvements in or relating to the manufacture of acrolein oxime and acrylonitrile Expired GB561403A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1608342A GB561403A (en) 1942-11-13 1942-11-13 Improvements in or relating to the manufacture of acrolein oxime and acrylonitrile

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1608342A GB561403A (en) 1942-11-13 1942-11-13 Improvements in or relating to the manufacture of acrolein oxime and acrylonitrile

Publications (1)

Publication Number Publication Date
GB561403A true GB561403A (en) 1944-05-18

Family

ID=10070865

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1608342A Expired GB561403A (en) 1942-11-13 1942-11-13 Improvements in or relating to the manufacture of acrolein oxime and acrylonitrile

Country Status (1)

Country Link
GB (1) GB561403A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2820825A (en) * 1955-10-07 1958-01-21 Phillips Petroleum Co Production of oximes
CN114908028A (en) * 2022-04-19 2022-08-16 杭州师范大学 One-pot synthesis process for catalyzing nitrile compounds through chemical enzyme method cascade in two-phase system
CN116217430A (en) * 2022-12-31 2023-06-06 江苏艾科维科技股份有限公司 Separation and purification method of high-concentration anhydrous aldoxime
CN114908028B (en) * 2022-04-19 2024-05-31 杭州师范大学 One-pot synthesis process of nitrile compound by chemical enzyme method cascading catalysis under two-phase system

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2820825A (en) * 1955-10-07 1958-01-21 Phillips Petroleum Co Production of oximes
CN114908028A (en) * 2022-04-19 2022-08-16 杭州师范大学 One-pot synthesis process for catalyzing nitrile compounds through chemical enzyme method cascade in two-phase system
CN114908028B (en) * 2022-04-19 2024-05-31 杭州师范大学 One-pot synthesis process of nitrile compound by chemical enzyme method cascading catalysis under two-phase system
CN116217430A (en) * 2022-12-31 2023-06-06 江苏艾科维科技股份有限公司 Separation and purification method of high-concentration anhydrous aldoxime
CN116217430B (en) * 2022-12-31 2024-05-31 江苏艾科维科技股份有限公司 Separation and purification method of high-concentration anhydrous aldoxime

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