Improvements in the production of o.o-dialkylphosphoric and o.o-dialkylthionophosphoric acid esters of substituted halogen-butenols

    公开(公告)号:GB815965A

    公开(公告)日:1959-07-01

    申请号:GB3158

    申请日:1958-01-01

    Applicant: BASF AG

    Abstract: The invention comprises esters of formula where R and R1 are C1-4 alkyl groups, X is O or S, Hal is halogen, Z is H or a C1-4 saturated or unsaturated aliphatic hydrocarbon radical and Y is O or S or a sulphone, sulphoxy or -NH-group. They may be prepared by reacting an O,O-dialkyl phosphoric acid monohalide with a 3-halogen-butene-(3)-ol-(2) substituted in the 1-position of formula Specified butenols include various 1-alkoxy-, 1-alkenoxy-, 1-monoalkylamino-, 1-mono-alkenylamino-, 1 - alkylmercapto-, 1 - alkenylmercapto -, 1 - alkyl - or alkenyl - sulphoxy - or sulphonyl - 3 - chloro -, bromo - or iodo butene-(3)-ol-(2). Suitable phosphorus halides include the monochlorides, bromides and iodides of dialkylphosphoric and thionophosphoric acids. The reaction occurs in the cold but a temperature of 15-120 DEG C., preferably 40-50 DEG C., is preferred. An inert solvent may be used such as a hydrocarbon or chlorohydrocarbon. An acid-binding agent may also be used such as a tertiary amine or alkali carbonate or bicarbonate. Examples describe the preparation by reaction of the appropriate butenol and dialkyl phosphoric or thionophosphoric acid chloride or bromide of (1) diethyl 1-methoxy-3-chloro - butene - 3 - yl - 2 thionophosphate; (2) diethyl 1 - n - propylamino - 3 - chlorobutene - 3-yl-2 thionophosphate; (3) diethyl 1-ethylmercapto - 3 - chloro - butene - 3 - yl thionophosphate; (4) dimethyl 1-ethyl-mercapto-3-chloro - butene - 3 - yl - 2 thionophosphate; (5) dibutyl 1 - n - propylamino - 3 - chloro - butene - 3 - yl - 2 thionophosphate; (6) dipropyl 1 - ethylmercapto - 3 - chloro - butene - 3 - yl - 2 thionophosphate; (7) diethyl 1 - n - propylamino - 3 - chlorobutene - 3 - yl - 2 phosphate; (8) diethyl 1-amino-3-chloro-butene-3-yl-2 thionophosphate; and (9) diethyl 1-allylamino-3 -chlorobutene - 3 - yl - 2 thionophosphate; acid binding agents used are pyridine, and triethylamine which also act as solvents and sodium carbonate using methylene chloride as solvent.

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