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US 6,046,368 AGranted
Catalytic process for making hydrofluoroethers
Assignee3M Innovative Properties Company
InventorsWilliam M. Lamanna, Richard M. Flynn, Daniel R. Vitcak, Zai-Ming Qiu
Life of this patent
Estimating the term…
Abstract
Briefly, in one aspect, this invention provides a catalytic method of preparation of primary and secondary hydrofluoroethers, the process comprising reacting a fluorinated precursor material and an alkylating agent in the presence of a Lewis acid catalyst or a mixture comprising Lewis acid and Bronsted acid catalysts.
Claims26
A process for the preparation of hydrofluoroether compounds, said process comprising:
- (1) reacting in the presence of at least one Lewis acid catalyst or a mixture comprising Lewis acid and Bronsted acid catalysts:
- a) a fluorinated ketene or a fluorinated carbonyl-containing compound of the formula:
- ##STR27## wherein n is an integer equal to 1, 2 or 3;
- and when n is 1, R.sub.f is a fluorine atom or is a fluorinated alkyl group having from 1 to about 15 carbon atoms that may be substituted or unsubstituted, saturated or unsaturated, cyclic or acyclic, linear or branched and may optionally contain one or more catenary heteroatoms;
- when n is 2, R.sub.f is a fluorinated alkylene group having from 1 to about 15 carbon atoms that may be substituted or unsubstituted, saturated or unsaturated, cyclic or acyclic, linear or branched and may optionally contain one or more catenary heteroatoms;
- when n is 3, R.sub.f is a fluorinated alkylidene group having from 1 to about 15 carbon atoms that may be substituted or unsubstituted, saturated or unsaturated, cyclic or acyclic, linear or branched and may optionally contain one or more catenary heteroatoms;
- and
- wherein each non-fluorine substituent on the above R.sub.f group may optionally include --Cl, --H, --Br, --SO.sub.2 X, --SO.sub.2 R', --COX --CO.sub.2 R', or --OR' where R' is a fluorinated or non-fluorinated alkyl group;
- and
- each X is independently a hydrogen or a halogen atom or is of the formula R'.sub.f or OR'.sub.f where R'.sub.f is a partially or fully fluorinated or non-fluorinated alkyl group having from 1 to about 10 carbon atoms that may be substituted or unsubstituted, saturated or unsaturated, cyclic or acyclic, linear or branched and may optionally contain one or more catenary heteroatoms;
- where X is an R'.sub.f group, that R'.sub.f group may form a ring with the R.sub.f group previously defined;
- and
- b) an alkylating agent of the formula:
- R--F
- wherein:
- R is a substituted or unsubstituted, saturated or unsaturated, cyclic or acyclic, linear or branched, non-halogenated or partially halogenated alkyl group having from 1 to about 10 carbon atoms that can optionally include one or more catenary heteroatoms, where if said R group is substituted, the non-hydrogen substituents may optionally include --Cl, --Br, --F, --SO.sub.2 X, --SO.sub.2 R', --COX', --COR', --CO.sub.2 R', or --OR' where R' is a fluorinated or non-fluorinated alkyl group and where X' is a halogen atom, and with the proviso that when R is perfluorinated, the R--F compound has an activated C--F bond;
- and
- (2) recovering hydrofluoroether from the resulting reaction mixture.
15 more elements
A process for the preparation of hydrofluoroether compounds, said process comprising:
- (1) reacting in the presence of at least one Lewis acid catalyst or a mixture comprising Lewis acid and Bronsted acid catalysts:
- a) a fluorinated mono- or polyether compound or a fluorinated oxacycloalkane with
- b) an alkylating agent of the general formula:
- R--F
- wherein:
- R is a substituted or unsubstituted, saturated or unsaturated, cyclic or acyclic, linear or branched, non-halogenated or partially halogenated alkyl group having from 1 to about 10 carbon atoms that can optionally include one or more catenary heteroatoms such as oxygen, nitrogen or sulfur, where if said R group is substituted, the non-hydrogen substituents may optionally include --Cl, --Br, --F, --SO.sub.2 X', --SO.sub.2 R', --COX', --COR', --CO.sub.2 R', or --OR' (where R' is as defined above and where X' is a halogen atom) and with the proviso that when R is perfluorinated, the R--F compound has an activated C--F bond;
- and
- (2) recovering hydrofluoroether from the resulting mixture.
5 more elements
A process for the preparation of hydrofluoroether compounds, said process comprising:
- (1) reacting in the presence of at least one Lewis acid catalyst or a mixture comprising Lewis acid and Bronsted acid catalysts:
- a) a fluorinated mono- or polyether compound with
- b) a fluorinated ketene or a fluorinated carbonyl-containing compound of the formula:
- ##STR29## wherein n is an integer equal to 1, 2 or 3;
- and when n is 1, R.sub.f is a fluorine atom or is a fluorinated alkyl group having from 1 to about 15 carbon atoms that may be substituted or unsubstituted, saturated or unsaturated, cyclic or acyclic, linear or branched and may optionally contain one or more catenary heteroatoms;
- when n is 2, R.sub.f is a fluorinated alkylene group having from 1 to about 15 carbon atoms that may be substituted or unsubstituted, saturated or unsaturated, cyclic or acyclic, linear or branched and may optionally contain one or more catenary heteroatoms;
- when n is 3, R.sub.f is a fluorinated alkylidene group having from 1 to about 15 carbon atoms that may be substituted or unsubstituted, saturated or unsaturated, cyclic or acyclic, linear or branched and may optionally contain one or more catenary heteroatoms;
- and
- wherein each non-fluorine substituent on the above R.sub.f group may optionally include --Cl, --H, --Br, --SO.sub.2 X, --SO.sub.2 R', --COX, --CO.sub.2 R', or --OR' where R' is a fluorinated or non-fluorinated alkyl group;
- and
- each X is independently a hydrogen or a halogen atom or is of the formula R'.sub.f or OR'.sub.f where R'.sub.f is a partially or fully fluorinated or non-fluorinated alkyl group having from 1 to about 10 carbon atoms that may be substituted or unsubstituted, saturated or unsaturated, cyclic or acyclic, linear or branched and may optionally contain one or more catenary heteroatoms;
- where X is an R'.sub.f group, that R'.sub.f group may form a ring with the R.sub.f group previously defined;
- and
- (2) recovering hydrofluoroether from the resulting mixture.
11 more elements
Dependencies are inferred from the claim text.