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Description:
This ... |
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Process for the synthesis of .alpha.-chlorinated chloroformates
| Details |
Inventors: Cagnon, Guy C.; Piteau, Marc D.; Senet, Jean-Pierre G.; Olofson, Roy A.; Martz, Jonathan T.;
Assignee: Societe Nationale des Poudres et Explosifs (Paris, FR)
Primary Examiner:
Assistant Examiner:
Attorney, Agent or Firm:
Process for the synthesis of .alpha.-chlorinated chloroformates, and new .alpha.-chlorinated chloroformates. The invention relates to a new process for the manufacture of .alpha.-chlorinated chloroformates and, to new .alpha.-chlorinated chloroformates as new industrial products. The process according to the invention consists of a synthesis, by catalytic phosgenation, of .alpha.-chlorinated chloroformates of the formula: ##STR1## in which: R represents a substituted or unsubstituted hydrocarbon radical and m represents an integer superior or equal to one, this synthesis consisting in reacting phosgene with the aldehyde R--CHO).sub.m, in the presence of a catalyst which is an organic or inorganic substance which is capable in a medium containing an aldehyde of the formula R--CHO).sub.m, phosgene and, possibly, a solvent, of generating a pair of ions one of which is an halogenide anion and the other is a cation which is sufficiently separated from said halogenide anion so as to give to the latter a nucleophilic power enabling it to react with the function(s) aldehyde of the molecule R--CHO).sub.m. |
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DETAILED DESCRIPTION We claim: 1.
The process for the synthesis of .
alpha.
-chlorinated chloroformates of the formula: ##STR13## wherein: R is alkyl of 1 to 4 carbon atoms, or R is--CCl.
sub.
3 which consists of reacting phosgene with an aldehyde of formula RCHO, wherein R has the same meaning as above in the presence of 1-10% mole of a catalyst which is a member selected from the group consisting of pyridine, N,N-dimethylaminopyridine, imidazole, tertiary aliphatic phosphines, and a member of the group of amides, ureas, thioureas, phosphoramides wherein the N atoms are completely substituted by alkyl groups and the products of reactions of these catalysts with phosgene.
2.
Process according to claim 1 wherein the catalyst is a member selected from the group consisting of pyridine, N,N-dimethylaminopyridine, dimethylforamide, tetra-n-butyl urea, trioctyl phosphine, hexamethyl phosphotriamide and imidazole.
3.
The process according to claim 1 wherein the reaction is carried out in a solvent which is carbon tetrachloride, chloroform, dichloromethane, toluene, chlorobenzene or hexane.
4.
The process according to claim 2 wherein the catalyst is dimethylformamide, hexamethylphosphotriamide, tetra-n-butyl urea, trioctylphosphine or pyridine and the temperature is 0.
degree.
-70.
degree.
C.
5.
The process according to claim 2 wherein the catalyst is N,N-dimethylamino pyridine, imidazole, and the temperature is in excess of 70.
degree.
.
6.
The process according to claim 1 wherein the aldehyde is acetaldehyde, the catalyst is tetra n-butyl urea, the reaction is carried out in dichloromethane or carbon tetrachloride and the temperature does not exceed 40.
degree.
C.
during the reaction with phosgene.
7.
The process according to claim 1 wherein the amount of the catalyst is 5% mole with respect to the molar amount of said aldehyde.
8.
The process according to claim 1 wherein the aldehyde is acetaldehyde, valeraldehyde or chloral.
Description:
The invention relates to the manufacture of .
alpha
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Molecular Biology 
