JPH06298693A - ジフルオロメチルメチルエーテルの気相塩素化方法 - Google Patents
ジフルオロメチルメチルエーテルの気相塩素化方法Info
- Publication number
- JPH06298693A JPH06298693A JP6044064A JP4406494A JPH06298693A JP H06298693 A JPH06298693 A JP H06298693A JP 6044064 A JP6044064 A JP 6044064A JP 4406494 A JP4406494 A JP 4406494A JP H06298693 A JPH06298693 A JP H06298693A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- fluorinated
- hoch
- hydrogen fluoride
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 25
- 238000005660 chlorination reaction Methods 0.000 title claims description 17
- CGZAMBNIGLUBRY-UHFFFAOYSA-N difluoro(methoxy)methane Chemical compound COC(F)F CGZAMBNIGLUBRY-UHFFFAOYSA-N 0.000 title abstract description 10
- 239000012808 vapor phase Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 239000001301 oxygen Substances 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 12
- 230000008569 process Effects 0.000 claims abstract description 9
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical class COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 6
- 239000000460 chlorine Substances 0.000 claims description 32
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 16
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- 239000007789 gas Substances 0.000 claims description 10
- 238000003682 fluorination reaction Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 5
- -1 hydrogen fluoride anhydride Chemical class 0.000 claims description 5
- 150000005218 dimethyl ethers Chemical class 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 230000000711 cancerogenic effect Effects 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 231100000315 carcinogenic Toxicity 0.000 abstract 1
- 239000000047 product Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- IOCGMLSHRBHNCM-UHFFFAOYSA-N difluoromethoxy(difluoro)methane Chemical compound FC(F)OC(F)F IOCGMLSHRBHNCM-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000000926 separation method Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VBPQHEWBJDVOBN-UHFFFAOYSA-N 1-(1,1-difluoroethoxy)-1,1-difluoroethane Chemical class CC(F)(F)OC(C)(F)F VBPQHEWBJDVOBN-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 6
- 231100000357 carcinogen Toxicity 0.000 description 5
- 239000003183 carcinogenic agent Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 150000001804 chlorine Chemical class 0.000 description 2
- 239000002826 coolant Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- HKYGSMOFSFOEIP-UHFFFAOYSA-N dichloro(dichloromethoxy)methane Chemical compound ClC(Cl)OC(Cl)Cl HKYGSMOFSFOEIP-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000003507 refrigerant Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- KHAKGKWRVBOSND-UHFFFAOYSA-N 1,1,2-trifluoro-1-(1,1,2-trifluoroethoxy)ethane Chemical compound FCC(F)(F)OC(F)(F)CF KHAKGKWRVBOSND-UHFFFAOYSA-N 0.000 description 1
- LLSWESFIHBBZME-UHFFFAOYSA-N 2,2-dichloro-1-(2,2-dichloro-1,1-difluoroethoxy)-1,1-difluoroethane Chemical compound ClC(Cl)C(F)(F)OC(F)(F)C(Cl)Cl LLSWESFIHBBZME-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- LTVOKYUPTHZZQH-UHFFFAOYSA-N difluoromethane Chemical group F[C]F LTVOKYUPTHZZQH-UHFFFAOYSA-N 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 230000004992 fission Effects 0.000 description 1
- 239000012025 fluorinating agent Substances 0.000 description 1
- SGAMQLNREKTWEK-UHFFFAOYSA-N fluoro(fluoromethoxy)methane Chemical class FCOCF SGAMQLNREKTWEK-UHFFFAOYSA-N 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 235000020004 porter Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/12—Saturated ethers containing halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/025,009 US5278342A (en) | 1992-03-25 | 1993-03-15 | Vapor phase chlorination of difluoromethyl methyl ether |
| US08/025009 | 1993-03-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH06298693A true JPH06298693A (ja) | 1994-10-25 |
Family
ID=21823552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6044064A Pending JPH06298693A (ja) | 1993-03-15 | 1994-03-15 | ジフルオロメチルメチルエーテルの気相塩素化方法 |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPH06298693A (enrdf_load_html_response) |
| KR (1) | KR100285073B1 (enrdf_load_html_response) |
| CN (1) | CN1054115C (enrdf_load_html_response) |
| AU (1) | AU669604B2 (enrdf_load_html_response) |
| BR (1) | BR9401152A (enrdf_load_html_response) |
| CA (1) | CA2118828A1 (enrdf_load_html_response) |
| MY (1) | MY110487A (enrdf_load_html_response) |
| TW (1) | TW252973B (enrdf_load_html_response) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018123649A1 (ja) * | 2016-12-29 | 2018-07-05 | セントラル硝子株式会社 | １，２，２，２－テトラフルオロエチルジフルオロメチルエーテル（デスフルラン）の製造方法 |
| JP2018115146A (ja) * | 2017-01-13 | 2018-07-26 | セントラル硝子株式会社 | １，２，２，２−テトラフルオロエチルジフルオロメチルエーテル（デスフルラン）の製造方法 |
| US10683252B2 (en) | 2016-12-29 | 2020-06-16 | Central Glass Company, Limited | Production method for 1,2,2,2-tetrafluoroethyl difluoromethyl ether (desflurane) |
| US10882809B2 (en) | 2016-12-29 | 2021-01-05 | Central Glass Company, Limited | Production method for halogenated alpha-fluoroethers |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU641049B2 (en) * | 1990-10-02 | 1993-09-09 | Hampshire Chemical Corp. | Synthesis of fluorinated dimethyl ethers |
-
1994
- 1994-03-11 AU AU57778/94A patent/AU669604B2/en not_active Ceased
- 1994-03-11 CA CA002118828A patent/CA2118828A1/en not_active Abandoned
- 1994-03-14 CN CN94104805A patent/CN1054115C/zh not_active Expired - Fee Related
- 1994-03-15 BR BR9401152A patent/BR9401152A/pt not_active IP Right Cessation
- 1994-03-15 JP JP6044064A patent/JPH06298693A/ja active Pending
- 1994-03-15 KR KR1019940005112A patent/KR100285073B1/ko not_active Expired - Fee Related
- 1994-03-16 MY MYPI94000614A patent/MY110487A/en unknown
- 1994-04-26 TW TW083103735A patent/TW252973B/zh active
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018123649A1 (ja) * | 2016-12-29 | 2018-07-05 | セントラル硝子株式会社 | １，２，２，２－テトラフルオロエチルジフルオロメチルエーテル（デスフルラン）の製造方法 |
| US10683252B2 (en) | 2016-12-29 | 2020-06-16 | Central Glass Company, Limited | Production method for 1,2,2,2-tetrafluoroethyl difluoromethyl ether (desflurane) |
| US10882809B2 (en) | 2016-12-29 | 2021-01-05 | Central Glass Company, Limited | Production method for halogenated alpha-fluoroethers |
| JP2018115146A (ja) * | 2017-01-13 | 2018-07-26 | セントラル硝子株式会社 | １，２，２，２−テトラフルオロエチルジフルオロメチルエーテル（デスフルラン）の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| MY110487A (en) | 1998-08-29 |
| CA2118828A1 (en) | 1994-09-16 |
| TW252973B (enrdf_load_html_response) | 1995-08-01 |
| CN1100711A (zh) | 1995-03-29 |
| AU5777894A (en) | 1994-09-22 |
| KR100285073B1 (ko) | 2001-04-02 |
| CN1054115C (zh) | 2000-07-05 |
| BR9401152A (pt) | 1994-11-01 |
| KR940021492A (ko) | 1994-10-19 |
| AU669604B2 (en) | 1996-06-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20050104 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20050208 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20060608 |