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US4592872A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for the synthesis of α-chlorinated chloroformates

Assignee: Societe Nationale des Poudres et Explosifs
•
Filing: 1982-01-22
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Granted: 1986-06-03
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Expires: 2002-01-22
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Abstract

Abstract 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: <IMAGE> 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)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)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)m.

Inventors

  • 👤 Guy C. Cagnon
  • 👤 Marc D. Piteau
  • 👤 Jean-Pierre G. Senet
  • 👤 Roy A. Olofson
  • 👤 Jonathan T. Martz

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 21:07
CPC Classifications
C; C07; C07C; C07C69/00; C07C69/96; C07C68/00; C07C68/02

Claims Analysis

Total Claims: 9
Claim 1
Independent Claim 101 words
The process for the synthesis of α-chlorinated chloroformates of the formula: ##STR13## wherein: R is alkyl of 1 to 4 carbon atoms, or R is--CCl 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.
Claim 2
Dependent Claim 101 words
The process for the synthesis of α-chlorinated chloroformates of the formula: ##STR13## wherein: R is alkyl of 1 to 4 carbon atoms, or R is--CCl 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.
Claim 3
Dependent Claim 28 words
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.
Claim 4
Dependent Claim 25 words
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.
Claim 5
Dependent Claim 23 words
The process according to claim 2 wherein the catalyst is dimethylformamide, hexamethylphosphotriamide, tetra-n-butyl urea, trioctylphosphine or pyridine and the temperature is 0°-70° C.
Claim 6
Dependent Claim 21 words
The process according to claim 2 wherein the catalyst is N,N-dimethylamino pyridine, imidazole, and the temperature is in excess of 70°.
Claim 7
Dependent Claim 40 words
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° C. during the reaction with phosgene.
Claim 8
Dependent Claim 24 words
The process according to claim 1 wherein the amount of the catalyst is 5% mole with respect to the molar amount of said aldehyde.
Claim 9
Dependent Claim 14 words
The process according to claim 1 wherein the aldehyde is acetaldehyde, valeraldehyde or chloral.

References Cited (Backward Citations)

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USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1989-06-02 1989-12-02 1990-06-03 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1993-06-02 1993-12-02 1994-06-03 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1997-06-02 1997-12-02 1998-06-03 $7700.00 Window Closed / Lapsed

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