JPS6354331A - Production of 1,1-difluorocyclohexane - Google Patents
Production of 1,1-difluorocyclohexaneInfo
- Publication number
- JPS6354331A JPS6354331A JP19810386A JP19810386A JPS6354331A JP S6354331 A JPS6354331 A JP S6354331A JP 19810386 A JP19810386 A JP 19810386A JP 19810386 A JP19810386 A JP 19810386A JP S6354331 A JPS6354331 A JP S6354331A
- Authority
- JP
- Japan
- Prior art keywords
- trifluoroacetic acid
- acylalation
- cyclohexanone
- react
- raw material
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 title 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 abstract 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N Trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 abstract 4
- 238000000034 method Methods 0.000 abstract 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N Cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N HF Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 abstract 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N Phosphorus pentoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 abstract 2
- 239000002994 raw material Substances 0.000 abstract 2
- XIEADFPBUGUUSG-UHFFFAOYSA-N [1-(2,2,2-trifluoroacetyl)oxycyclohexyl] 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)OC1(OC(=O)C(F)(F)F)CCCCC1 XIEADFPBUGUUSG-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 238000003682 fluorination reaction Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Abstract
PURPOSE: To obtain the titled compound in high yield and selectivity, by using cyclohexanone as a raw material and combining an acylalation process, a fluorination process and a trifluoroacetic acid recovering process.
CONSTITUTION: Cyclohexanone is made to react with trifluoroacetic anhydride preferably at 0W150°C and the obtained, 1,1-bis(trifluoroacetoxy)cyclohexane is made to react with hydrogen fluoride (containing ≤10wt%, especially ≤1wt% water) or a mixture of hydrogen fluoride and an amine preferably at -40W+100°C to obtain the objective compound and trifluoroacetic acid. The trifluoroacetic acid is reacted with a dehydration agent (e.g. phosphorus pentoxide) and the obtained trifluoroacetic anhydride is recovered by distillation, etc., and used as a raw material for the acylalation process.
COPYRIGHT: (C)1988,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19810386A JPH0717548B2 (en) | 1986-08-26 | 1986-08-26 | Method for producing 1,1-difluorocyclohexane |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19810386A JPH0717548B2 (en) | 1986-08-26 | 1986-08-26 | Method for producing 1,1-difluorocyclohexane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6354331A true JPS6354331A (en) | 1988-03-08 |
| JPH0717548B2 JPH0717548B2 (en) | 1995-03-01 |
Family
ID=16385539
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19810386A Expired - Lifetime JPH0717548B2 (en) | 1986-08-26 | 1986-08-26 | Method for producing 1,1-difluorocyclohexane |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0717548B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006335720A (en) * | 2005-06-03 | 2006-12-14 | Asahi Kasei Corp | Method for producing polyacene compound and organic semiconductor element |
| EP1985603A1 (en) * | 2007-04-27 | 2008-10-29 | SOLVAY (Société Anonyme) | Process for preparing difluorocyclohexanoic acid derivatives |
| WO2008132128A2 (en) * | 2007-04-27 | 2008-11-06 | Solvay (Société Anonyme) | Synthesis of a pharmaceutically active compound |
| WO2013018465A1 (en) * | 2011-07-29 | 2013-02-07 | セントラル硝子株式会社 | Method for producing geminal difluoro compound |
-
1986
- 1986-08-26 JP JP19810386A patent/JPH0717548B2/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006335720A (en) * | 2005-06-03 | 2006-12-14 | Asahi Kasei Corp | Method for producing polyacene compound and organic semiconductor element |
| EP1985603A1 (en) * | 2007-04-27 | 2008-10-29 | SOLVAY (Société Anonyme) | Process for preparing difluorocyclohexanoic acid derivatives |
| WO2008132128A2 (en) * | 2007-04-27 | 2008-11-06 | Solvay (Société Anonyme) | Synthesis of a pharmaceutically active compound |
| WO2008132128A3 (en) * | 2007-04-27 | 2009-02-05 | Solvay | Synthesis of a pharmaceutically active compound |
| WO2013018465A1 (en) * | 2011-07-29 | 2013-02-07 | セントラル硝子株式会社 | Method for producing geminal difluoro compound |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0717548B2 (en) | 1995-03-01 |
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