GB651931A - Improvements in halogen containing derivatives of butadiene sulphone - Google Patents

Improvements in halogen containing derivatives of butadiene sulphone

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Publication number
GB651931A
GB651931A GB22362/48A GB2236248A GB651931A GB 651931 A GB651931 A GB 651931A GB 22362/48 A GB22362/48 A GB 22362/48A GB 2236248 A GB2236248 A GB 2236248A GB 651931 A GB651931 A GB 651931A
Authority
GB
United Kingdom
Prior art keywords
product
trichlorobromomethane
dioxide
peroxide
trichloromethyl
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
GB22362/48A
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.)
Uniroyal Inc
Original Assignee
United States Rubber Co
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 United States Rubber Co filed Critical United States Rubber Co
Publication of GB651931A publication Critical patent/GB651931A/en
Expired legal-status Critical Current

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

3-Bromo-4-trichloromethyl tetrahydro thiophene-1,1-dioxide is obtained by subjecting butadiene sulphone and trichlorobromomethane in the proportion of at least two mols. of trichlorobromomethane to one mol. of butadiene sulphone to the action of either actinic light or a diacyl peroxide at elevated temperature at which the diacyl peroxide is decomposed, until 3 - bromo - 4 - trichloromethyl tetrahydro thiophene-1,1-dioxide is formed and separating said product. The reaction initiator is preferably added in portions throughout the course of the reaction and may be effected at between 50 DEG C. and 120 DEG C. depending on the peroxide used as initiator. The product may be dehydrohalogenated by contacting it with an aqueous solution containing an alkali metal hydroxide to give an unsaturated derivative, 4-dichloromethylene 4,5-dihydro thiophene 1,1-dioxide, and this compound as well as the main product are stated to be useful as insecticides. In examples: (1) butadiene sulphone is added to trichlorobromomethane and a solution of diacetyl peroxide in trichlorobromomethane then added in five equal portions at half-hour intervals, the temperature being maintained at 80-85 DEG C. 3 - Bromo - 4 - trichloromethyl tetrahydro thiophene-1,1-dioxide is obtained; (2) the same product is obtained by placing a solution of butadiene sulphone in trichlorobromomethane in a glass apparatus containing a spiral neon fluorescent lamp. The air is displaced with nitrogen and the light turned on for 12 hours; (3) the product of (1) is dissolved in ethyl alcohol and titrated with potassium hydroxide solution to the colour change using phenolphthalein as indicator. The mixture is filtered and the dehydrohalogenated product obtained from the filtrate. The Specification as open to inspection under Sect. 91 refers to the use of any peroxide compound as reaction initiator. This subject-matter does not appear in the Specification as accepted.
GB22362/48A 1947-10-25 1948-08-25 Improvements in halogen containing derivatives of butadiene sulphone Expired GB651931A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US651931XA 1947-10-25 1947-10-25

Publications (1)

Publication Number Publication Date
GB651931A true GB651931A (en) 1951-04-11

Family

ID=22060955

Family Applications (1)

Application Number Title Priority Date Filing Date
GB22362/48A Expired GB651931A (en) 1947-10-25 1948-08-25 Improvements in halogen containing derivatives of butadiene sulphone

Country Status (1)

Country Link
GB (1) GB651931A (en)

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