TWI297004B - - Google Patents

Download PDF

Info

Publication number: TWI297004B
Authority: TW; Taiwan
Prior art keywords: fluorine; containing alcohol; formula; acid acceptor; methanol
Prior art date: 2000-08-28

Application number

TW90118880A

Other languages

English (en)

Chinese (zh)

Inventor

Yoshizawa Toru

Takaki Shoji

Original Assignee

Daikin Ind Ltd

Priority date (The priority date 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 date listed.)

2000-08-28

Filing date

2001-08-02

Publication date

2008-05-21

2001-08-02 Application filed by Daikin Ind Ltd filed Critical Daikin Ind Ltd

2008-05-21 Application granted granted Critical

2008-05-21 Publication of TWI297004B publication Critical patent/TWI297004B/zh

Links

OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 87
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 61
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 60
239000011737 fluorine Substances 0.000 claims description 60
229910052731 fluorine Inorganic materials 0.000 claims description 60
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 47
238000006243 chemical reaction Methods 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 24
238000000034 method Methods 0.000 claims description 24
239000007795 chemical reaction product Substances 0.000 claims description 23
238000004519 manufacturing process Methods 0.000 claims description 22
230000002378 acidificating effect Effects 0.000 claims description 21
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 14
239000012043 crude product Substances 0.000 claims description 12
150000001451 organic peroxides Chemical class 0.000 claims description 10
125000005739 1,1,2,2-tetrafluoroethanediyl group Chemical group FC(F)([*:1])C(F)(F)[*:2] 0.000 claims description 7
150000001298 alcohols Chemical class 0.000 claims description 6
238000009835 boiling Methods 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
238000010438 heat treatment Methods 0.000 claims description 6
239000007858 starting material Substances 0.000 claims description 6
238000000926 separation method Methods 0.000 claims description 4
-1 tetramethyl alcohol Chemical compound 0.000 claims description 4
238000000354 decomposition reaction Methods 0.000 claims description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
239000005977 Ethylene Substances 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 1
XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 claims 1
230000002093 peripheral effect Effects 0.000 claims 1
238000005502 peroxidation Methods 0.000 claims 1
238000004821 distillation Methods 0.000 description 52
CSUFEOXMCRPQBB-UHFFFAOYSA-N 1,1,2,2-tetrafluoropropan-1-ol Chemical compound CC(F)(F)C(O)(F)F CSUFEOXMCRPQBB-UHFFFAOYSA-N 0.000 description 29
239000002585 base Substances 0.000 description 14
239000010410 layer Substances 0.000 description 9
239000000975 dye Substances 0.000 description 8
239000003513 alkali Substances 0.000 description 7
239000012535 impurity Substances 0.000 description 6
239000000049 pigment Substances 0.000 description 6
239000000758 substrate Substances 0.000 description 6
AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000010025 steaming Methods 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
230000002079 cooperative effect Effects 0.000 description 3
238000004817 gas chromatography Methods 0.000 description 3
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
239000000047 product Substances 0.000 description 3
LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
238000002835 absorbance Methods 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
239000000920 calcium hydroxide Substances 0.000 description 2
229910001861 calcium hydroxide Inorganic materials 0.000 description 2
238000001944 continuous distillation Methods 0.000 description 2
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 2
238000005259 measurement Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000000523 sample Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
HUAUNKAZQWMVFY-UHFFFAOYSA-M sodium;oxocalcium;hydroxide Chemical compound [OH-].[Na+].[Ca]=O HUAUNKAZQWMVFY-UHFFFAOYSA-M 0.000 description 2
IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 2
KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 1
QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
XELSBTMMZRMLAS-UHFFFAOYSA-N 1,1,2,2-tetrachloropropan-1-ol Chemical compound CC(Cl)(Cl)C(O)(Cl)Cl XELSBTMMZRMLAS-UHFFFAOYSA-N 0.000 description 1
PGJHURKAWUJHLJ-UHFFFAOYSA-N 1,1,2,3-tetrafluoroprop-1-ene Chemical compound FCC(F)=C(F)F PGJHURKAWUJHLJ-UHFFFAOYSA-N 0.000 description 1
SZVMZLJAAGWNPG-UHFFFAOYSA-N 1-tert-butylperoxyoctane Chemical compound CCCCCCCCOOC(C)(C)C SZVMZLJAAGWNPG-UHFFFAOYSA-N 0.000 description 1
FZKCAHQKNJXICB-UHFFFAOYSA-N 2,1-benzoxazole Chemical compound C1=CC=CC2=CON=C21 FZKCAHQKNJXICB-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
229930182558 Sterol Natural products 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
150000004056 anthraquinones Chemical class 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
239000011575 calcium Substances 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000000919 ceramic Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000013058 crude material Substances 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000014380 magnesium carbonate Nutrition 0.000 description 1
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
239000000347 magnesium hydroxide Substances 0.000 description 1
229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
108091008695 photoreceptors Proteins 0.000 description 1
239000001007 phthalocyanine dye Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000004926 polymethyl methacrylate Substances 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
239000004810 polytetrafluoroethylene Substances 0.000 description 1
229920001343 polytetrafluoroethylene Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
RKCAIXNGYQCCAL-UHFFFAOYSA-N porphin Chemical compound N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 RKCAIXNGYQCCAL-UHFFFAOYSA-N 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
239000011241 protective layer Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical class C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000013074 reference sample Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
150000003432 sterols Chemical class 0.000 description 1
235000003702 sterols Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
238000009834 vaporization Methods 0.000 description 1
230000008016 vaporization Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/32—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

TW90118880A 2000-08-28 2001-08-02 TWI297004B (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP2000257853A JP2002069021A (ja)	2000-08-28	2000-08-28	含フッ素アルコールの製造方法

Publications (1)

Publication Number	Publication Date
TWI297004B true TWI297004B (fr)	2008-05-21

Family

ID=18746250

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW90118880A TWI297004B (fr)	2000-08-28	2001-08-02

Country Status (4)

Country	Link
JP (1)	JP2002069021A (fr)
CN (1)	CN1441762A (fr)
TW (1)	TWI297004B (fr)
WO (1)	WO2002018308A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN100412042C (zh) *	2005-03-01	2008-08-20	常熟三爱富中昊化工新材料有限公司	一种四氟丙醇的提纯方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3915759A1 (de) *	1989-05-13	1990-11-15	Hoechst Ag	Verfahren zur herstellung von telomeralkoholen
JP3026804B1 (ja) *	1999-03-15	2000-03-27	ダイキン工業株式会社	フッ素アルコ―ルの製造法
JP2000273060A (ja) *	1999-03-19	2000-10-03	Daikin Ind Ltd	フッ素アルコールの製造法

2000
- 2000-08-28 JP JP2000257853A patent/JP2002069021A/ja active Pending
2001
- 2001-07-13 CN CN 01812508 patent/CN1441762A/zh active Pending
- 2001-07-13 WO PCT/JP2001/006074 patent/WO2002018308A1/fr not_active Ceased
- 2001-08-02 TW TW90118880A patent/TWI297004B/zh not_active IP Right Cessation

Also Published As

Publication number	Publication date
JP2002069021A (ja)	2002-03-08
WO2002018308A1 (fr)	2002-03-07
CN1441762A (zh)	2003-09-10

Legal Events

Date	Code	Title	Description
2012-02-21	MM4A	Annulment or lapse of patent due to non-payment of fees

Publication	Publication Date	Title
JPH08225496A (ja)	1996-09-03	スクラップポリエステルのエステルモノマーへの転化方法
RU2166495C1 (ru)	2001-05-10	Способ получения фторспирта (варианты)
JP3029618B1 (ja)	2000-04-04	フッ素アルコ―ルの製造法
TWI297004B (fr)	2008-05-21
TW572876B (en)	2004-01-21	Method for producing a fluorine-containing alcohol
RU2264378C2 (ru)	2005-11-20	Способ получения фторированного спирта
TWI250975B (en)	2006-03-11	Process for producing fluoroalcohol
RU2163230C1 (ru)	2001-02-20	Способ получения фторспирта
JP2002069019A (ja)	2002-03-08	含フッ素アルコールの製造方法
US6673976B1 (en)	2004-01-06	Process of making fluorinated alcohols
JP3685244B2 (ja)	2005-08-17	フッ素アルコールの製造法
GB1582830A (en)	1981-01-14	Production of chloroprene
JP2001187756A (ja)	2001-07-10	フッ素系アルコールの回収方法
WO2001062694A1 (fr)	2001-08-30	Procede de preparation de 2,2,3,4,4,4-hexafluoro-1-butanol et utilisation de ladite substance
WO2001002329A1 (fr)	2001-01-11	Procede de production de fluoroalcanol
JP2000273060A (ja)	2000-10-03	フッ素アルコールの製造法
JP2001187755A (ja)	2001-07-10	フッ素系溶剤の回収方法
JPH0489470A (ja)	1992-03-23	高品質ｎ―（２―クロロエチル）アルキルスルホンアミドの製造方法