# US 8,273,914 B1 · Process for preparing vinyl chloroformate > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 8,273,914 B1 - Document ID: US8273914B1 - Status: Granted - Kind: B1 - Application number: 13/169,085 - Filed: 2011-06-27 - Granted: 2012-09-25 - Earliest claimed: 2011-06-27 - Assignees: Bausch & Lomb Incorporated - Inventors: Ivan M. Nunez; David E. Seelye - Web page: https://patentgrep.com/patent/US8273914B1 ## CPC - C07C 67/02: by interreacting ester groups, i.e. transesterification - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract Disclosed is a process for making vinyl chloroformate which includes reacting (a) a carbonyl compound of formula I: wherein R is a halogen or an alkyl group of 1 to about 25 carbon atoms; with (b) a silyl-containing enol ether and in the presence of an effective amount of a Group VIII-containing catalyst. ## Claims ### Claim 1 A process for making vinyl chloroformate, the process comprising reacting (a) a carbonyl compound of formula I: wherein R is a halogen or an alkyl group of 1 to about 26 carbon atoms; with (b) a silyl-containing enol ether of formula II and in the presence of an effective amount of a Group VIII metal-containing catalyst wherein R1, R2 and R3 are independently a hydrocarbyl group of 1 to about 30 carbon atoms and R4, R5 and R6 are independently hydrogen or a C1 to C6 alkyl group. ### Claim 2 (depends on 1) The process of claim 1, wherein the hydrocarbyl groups is a substituted or unsubstituted, straight or branched C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 cycloalkylalkyl group, a substituted or unsubstituted C3 to C30 cycloalkenyl group, a substituted or unsubstituted C5 to C30 aryl group, or a substituted or unsubstituted C5 to C30 arylalkyl group. ### Claim 3 (depends on 1) The process of claim 1, wherein R is C1, R1, R2 and R3 are independently a substituted or unsubstituted, straight or branched C1 to C9 alkyl group and R4, R5 and R6 are hydrogen. ### Claim 4 (depends on 1) The process of claim 1, wherein the carbonyl compound of formula I is reacted with the silyl-containing enol ether in a molar ratio of the carbonyl compound of formula I to the silyl-containing enol ether ranging from about 1:1 to about 1:3. ### Claim 5 (depends on 1) The process of claim 1, wherein the Group VIII metal-containing catalyst comprises a palladium-containing catalyst or a platinum-containing catalyst. ### Claim 6 (depends on 1) The process of claim 1, wherein the Group VIII metal-containing catalyst comprises a palladium-containing catalyst. ### Claim 7 (depends on 6) The process of claim 6, wherein the palladium-containing catalyst comprises a palladium (0) or palladium (II)-containing catalyst. ### Claim 8 (depends on 6) The process of claim 6, wherein the palladium-containing catalyst is selected from the group consisting of tetrakis(triphenylphosphine)palladium (0), bis(benzonitrile)palladium (II) chloride, palladium (II) trifluoroacetate, palladium (II) dichloride, sodium tetrachloro palladium (II), dichlorobis(triphenylphosphine)palladium (II), palladium (II) acetate and mixtures thereof. ### Claim 9 (depends on 1) The process of claim 1, wherein the effective amount of the Group VIII-containing catalyst is from about 0.001 mole % to about 25 mole % relative to the silyl-containing enol ether. ### Claim 10 (depends on 1) The process of claim 1, wherein the reaction takes place in the presence of a non-aliphatic hydrocarbon-containing solvent. ### Claim 11 (depends on 1) The process of claim 1, wherein the non-aliphatic hydrocarbon-containing solvent is selected from the group consisting of an ether-containing solvent, a nitrile-containing solvent, an aromatic hydrocarbon-containing solvent, a cyclic urea-containing solvent and mixtures thereof. ### Claim 12 (depends on 11) The process of claim 11, wherein the ether-containing solvent is selected from the group consisting of 2-methoxyethylether, ethyleneglycol diethyl ether, dibutyl ether, tri(ethylene glycol) dimethyl ether, tetra(ethylene glycol) dimethyl ether, di(ethylene glycol) dibutyl ether and mixtures thereof. ### Claim 13 (depends on 11) The process of claim 11, wherein the nitrile-containing solvent is selected from the group consisting of acetonitrile, adiponitrile, cyclopentanecarbonitrile, cyclohexanecarbonitrile and mixtures thereof. ### Claim 14 (depends on 11) The process of claim 11, wherein the aromatic hydrocarbon-containing solvent is selected from the group consisting of toluene, xylene, benzene, nitrobenzene, benzonitrile and mixtures thereof. ### Claim 15 (depends on 11) The process of claim 11, wherein the cyclic urea-containing solvent is 1,3-dimethyl-2-imidazolidinone. ### Claim 16 A process for making vinyl chloroformate, the process comprising reacting (a) a carbonyl compound of the formula: with (b) a silyl-containing enol ether of the formula: wherein R1, R2 and R3 are independently a substituted or unsubstituted, straight or branched C1 to C9 alkyl group and in the presence of a palladium-containing catalyst or a platinum-containing catalyst. ### Claim 17 (depends on 16) The process of claim 16, wherein R1, R2 and R3 are methyl. ### Claim 18 (depends on 16) The process of claim 16, wherein the carbonyl compound of formula I is reacted with the silyl-containing enol ether in a molar ratio of the carbonyl compound of formula I to the silyl-containing enol ether ranging from about 1:1 to about 1:3. ### Claim 19 (depends on 16) The process of claim 16, wherein the palladium-containing catalyst is selected from the group consisting of tetrakis(triphenylphosphine)palladium (0), bis(benzonitrile)palladium (II) chloride, palladium (II) trifluoroacetate, palladium (II) dichloride, sodium tetrachloro palladium (II), dichlorobis(triphenylphosphine)palladium (II), palladium (II) acetate and mixtures thereof. ### Claim 20 (depends on 16) The process of claim 16, wherein the effective amount of the palladium-containing catalyst is from about 0.001 mole % to about 25 mole % relative to the silyl-containing enol ether. ### Claim 21 (depends on 16) The process of claim 16, wherein the reaction takes place in the presence of a non-aliphatic hydrocarbon-containing solvent. ### Claim 22 (depends on 21) The process of claim 21, wherein the non-aliphatic hydrocarbon-containing solvent is a nitrile-containing solvent. ### Claim 23 (depends on 21) The process of claim 21, wherein the non-aliphatic hydrocarbon-containing solvent is selected from the group consisting of 2-methoxyethylether, ethyleneglycol diethyl ether, dibutyl ether, tri(ethylene glycol) dimethyl ether, tetra(ethylene glycol) dimethyl ether, di(ethylene glycol) dibutyl ether, acetonitrile, toluene, xylene, benzene, nitrobenzene, benzonitrile, 1,3-dimethyl-2-imidazolidinone and mixtures thereof.