US4001309A
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Method of preparing polyfluoroalkyl group containing compounds
Assignee: AGC Inc
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Filing: 1973-04-16
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Granted: 1977-01-04
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Expires: 1993-04-16
Abstract
Abstract Polyfluoroalkyl group-containing compounds are prepared according to the following reaction: ##EQU1## wherein R f represents perfluoroalkyl groups containing C 1 -23 carbon atoms, R, R' and R" represent hydrogen atoms or lower alkyl groups, and X represents bromine atoms or iodine atoms. The polyfluoroalkyl group-containing esters having the formula R f CH 2 CH 2 OCOR, are converted by hydrolysis to polyfluoroalkyl group-containing alcohols having the formula R f CH 2 CH 2 OH wherein R f is defined as above.
Inventors
- 👤 Takao Hayashi
- 👤 Masashi Matsuo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 13:21
CPC Classifications
C; C07; C07C; C07C69/00; C07C69/62; C07C69/63; C07C31/00; C07C31/34; C07C31/40
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
115 words
A method of preparing perfluoroalkyl group containing compounds which comprises reacting a polyfluoroalkyl halide having the formula R f CH 2 CH 2 X, wherein R f represents a perfluoroalkyl group containing 1-23 carbon atoms and X represents a bromine atom or an iodine atom, with water and an amide having the formula RCONR'R", wherein R, R' and R" represent hydrogen atoms or lower alkyl groups under conditions in which the mole ratio of water to said polyfluoroalkyl halide is in the range from 1 : 1 to 10 : 1 and the ratio of said amide to said polyfluoroalkyl halide is at least 1 : 1 at a temperature from about 80° to 200°C.
Claim 2
Independent Claim
115 words
A method of preparing perfluoroalkyl group containing compounds which comprises reacting a polyfluoroalkyl halide having the formula R f CH 2 CH 2 X, wherein R f represents a perfluoroalkyl group containing 1-23 carbon atoms and X represents a bromine atom or an iodine atom, with water and an amide having the formula RCONR'R", wherein R, R' and R" represent hydrogen atoms or lower alkyl groups under conditions in which the mole ratio of water to said polyfluoroalkyl halide is in the range from 1 : 1 to 10 : 1 and the ratio of said amide to said polyfluoroalkyl halide is at least 1 : 1 at a temperature from about 80° to 200°C.
Claim 3
Dependent Claim
35 words
The method of claim 1, wherein the mole ratio of said water to said polyfluoroalkyl halide is 1 : 1 and the mole ratio of said amide to said polyfluoroalkyl halide is 1 : 1.
Claim 4
Dependent Claim
44 words
The method of claim 1, wherein the mole ratio of said water to said polyfluoroalkyl halide is in the range from 1 : 1 to 2 : 1 and the ratio of said amide to said polyfluoroalkyl halide is at least 1 : 1.
Claim 5
Dependent Claim
44 words
The method of claim 1, wherein the mole ratio of said water to said polyfluoroalkyl halide is in the range from 2 : 1 to 8 : 1 and the ratio of said amide to said polyfluoroalkyl halide is at least 1 : 1.
Claim 6
Independent Claim
119 words
A method of preparing a polyfluoroalkyl group-containing compound having the formula R f CH 2 CH 2 Z, wherein R f represents a perfluoroalkyl group containing 1 to 23 carbon atoms, Z is selected from the group consisting of OH, OCOR and mixtures thereof and R represents hydrogen or lower alkyl which comprises reacting 1 mole polyfluoroalkyl halide having the formula R f CH 2 CH 2 X wherein R f is defined as before and X represents a bromine or iodine with 1 to 10 moles of water and 5 to 100 moles of an amide having the formula RCONR'R" wherein R,R' and R" represent hydrogen or lower alkyl at a temperature from about 80° to 200° C.
Claim 7
Independent Claim
119 words
A method of preparing a polyfluoroalkyl group-containing compound having the formula R f CH 2 CH 2 Z, wherein R f represents a perfluoroalkyl group containing 1 to 23 carbon atoms, Z is selected from the group consisting of OH, OCOR and mixtures thereof and R represents hydrogen or lower alkyl which comprises reacting 1 mole polyfluoroalkyl halide having the formula R f CH 2 CH 2 X wherein R f is defined as before and X represents a bromine or iodine with 1 to 10 moles of water and 5 to 100 moles of an amide having the formula RCONR'R" wherein R,R' and R" represent hydrogen or lower alkyl at a temperature from about 80° to 200° C.
Claim 8
Dependent Claim
19 words
The method of claim 5, wherein the reaction is conducted at a temperature of from 120° to 160° C.
Claim 9
Dependent Claim
11 words
The method of claim 5, wherein R is a hydrogen atom.
Claim 10
Dependent Claim
35 words
The method of claim 5, wherein said amide having the formula RCONR'R" is HCONR'R", and at least one of the R' and R" groups is a lower alkyl group containing 1 to 5 carbon atoms.
Claim 11
Dependent Claim
30 words
The method of claim 5, wherein said amide having the formula RCONR'R" is HCONR'R", and both R' and R" groups are lower alkyl groups containing 1 to 5 carbon atoms.
Claim 12
Dependent Claim
14 words
The method of claim 5, wherein said amide having the formula RCONR'R" is dimethylformamide.
Claim 13
Dependent Claim
27 words
The method of claim 5, wherein said polyfluoroalkyl halide having the formula R f CH 2 CH 2 X is R f CH 2 CH 2 Br.
Claim 14
Dependent Claim
27 words
The method of claim 5, wherein said polyfluoroalkyl halide having the formula R f CH 2 CH 2 X is R f CH 2 CH 2 I.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-01-04 | 1980-07-05 | 1981-01-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-01-04 | 1984-07-05 | 1985-01-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-01-04 | 1988-07-05 | 1989-01-04 | $7700.00 | Window Closed / Lapsed |