Process for the preparation of .beta.-halogeno-tert.-alkyl isocyanates
AssigneeBayer Aktiengesellschaft
InventorRudiger Schubart
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AssigneeBayer Aktiengesellschaft
InventorRudiger Schubart
Estimating the term…
The invention relates to a new process for the preparation of known .beta.-halogeno-tert.-alkyl isocyanates of the formula ##STR1## in which X represents chlorine, Y represents hydrogen or chlorine, R.sup.1 represents in each case straight-chain or branched alkyl or halogeno alkyl and R.sup.2 represents in each case straight-chain or branched alkyl or halogeno alkyl or optionally halogen-and/or trifluoromethyl-substituted phenyl, where tert.-alkyl isocyanates of the formula (II) ##STR2## are reacted with chlorine, optionally under irradiation or in the presence of catalysts, in a suitable apparatus.
A process for the preparation of .beta.-halogeno-tert.-alkyl isocyanates of the formula (I) ##STR13## in which x represents chlorine,
The process according to claim wherein the reaction is carried out under irradiation.
Dependencies are inferred from the claim text.
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Preparation of derivatives of isocyanic acid: by reactions not involving the formation of isocyanate groups
Acyclic or carbocyclic compounds
Term ended 2 Apr 2012 (estimated)
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The invention relates to a new process for the preparation of known .beta.-halogeno-tert.-alkyl isocyanates, which can be used as intermediates for the synthesis of rubber additives or of biologically active compounds, such as for example herbicides (cf. e.g. EP-A 294 666).
It is already known that .beta.-monochloro-tert.-alkyl isocyanates are obtained when .beta.-hydroxy-tert.-alkylamines are first hydrochlorinated using thionyl chloride and then the corresponding chloro-amine-hydrochloride is converted to the isocyanate using phosgene (cf. DE-OS (German Published Specification) 2 045 906).
The poor yields of the chlorinated tert.-alkyl isocyanates are a disadvantage of this process.
812 g of tert.-butyl isocyanate are initially introduced, and are chlorinated with stirring by direct introduction of undiluted chlorine at 85.degree. to 100.degree. C. under irradiation by a (water-cooled) high-pressure Hg vapour immersion lamp. Samples are taken and the course of chlorination is followed by gas chromatography (GC). After a conversion of 95%, the reaction is terminated. 1225 g of crude product are obtained, which is fractionated on a 20 cm packed column (containing 3 mm glass Raschig rings).
The composition of the chlorination mixture immediately after the end of chlorination is as follows (in % by area): ##STR7## The following are obtained: ##STR8##
desired product