CS263391A3 - Process for preparing pentafluorodichloropropanes - Google Patents

Process for preparing pentafluorodichloropropanes Download PDF

Info

Publication number: CS263391A3
Authority: CS; Czechoslovakia
Prior art keywords: anhydrous; catalyst; chloroform; reaction; chloride
Prior art date: 1990-08-28

Application number

CS912633A

Other languages

Czech (cs)

English (en)

Inventor

Hirokazu Aoyama

Satoru Kono

Takashi Yasuhara

Souichi Ueda

Satoshi Koyama

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.)

1990-08-28

Filing date

1991-08-27

Publication date

1992-04-15

1990-08-28 Priority claimed from JP2227502A external-priority patent/JPH0784399B2/ja

1990-08-28 Priority claimed from JP2227501A external-priority patent/JPH0784398B2/ja

1991-08-27 Application filed by Daikin Ind Ltd filed Critical Daikin Ind Ltd

1992-04-15 Publication of CS263391A3 publication Critical patent/CS263391A3/cs

Links

JEWUXLHWYRSHJK-UHFFFAOYSA-N 2,2-dichloro-1,1,1,3,3-pentafluoropropane Chemical class FC(F)C(Cl)(Cl)C(F)(F)F JEWUXLHWYRSHJK-UHFFFAOYSA-N 0.000 title description 3
238000004519 manufacturing process Methods 0.000 title description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 82
239000003054 catalyst Substances 0.000 claims abstract description 33
UJIGKESMIPTWJH-UHFFFAOYSA-N 1,3-dichloro-1,1,2,2,3-pentafluoropropane Chemical compound FC(Cl)C(F)(F)C(F)(F)Cl UJIGKESMIPTWJH-UHFFFAOYSA-N 0.000 claims abstract description 22
COAUHYBSXMIJDK-UHFFFAOYSA-N 3,3-dichloro-1,1,1,2,2-pentafluoropropane Chemical compound FC(F)(F)C(F)(F)C(Cl)Cl COAUHYBSXMIJDK-UHFFFAOYSA-N 0.000 claims abstract description 20
VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims abstract description 19
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims abstract description 3
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 35
238000006243 chemical reaction Methods 0.000 claims description 30
239000000203 mixture Substances 0.000 claims description 24
238000000034 method Methods 0.000 claims description 22
239000002904 solvent Substances 0.000 claims description 9
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 6
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 6
239000002841 Lewis acid Substances 0.000 claims description 4
-1 antimony anhydride Chemical class 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 4
150000007517 lewis acids Chemical group 0.000 claims description 4
229910015900 BF3 Inorganic materials 0.000 claims description 3
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 claims description 3
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 3
235000005074 zinc chloride Nutrition 0.000 claims description 3
239000011592 zinc chloride Substances 0.000 claims description 3
LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims description 2
FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 claims description 2
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims 2
229910021578 Iron(III) chloride Inorganic materials 0.000 claims 1
229910052787 antimony Inorganic materials 0.000 claims 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 1
RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 30
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 11
239000000047 product Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 5
UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 5
238000004817 gas chromatography Methods 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000002994 raw material Substances 0.000 description 5
IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 description 4
KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000004215 Carbon black (E152) Substances 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
238000001816 cooling Methods 0.000 description 4
229930195733 hydrocarbon Natural products 0.000 description 4
150000002430 hydrocarbons Chemical class 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Chemical class Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
229910052782 aluminium Inorganic materials 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
AFYPFACVUDMOHA-UHFFFAOYSA-N chlorotrifluoromethane Chemical compound FC(F)(F)Cl AFYPFACVUDMOHA-UHFFFAOYSA-N 0.000 description 3
230000007423 decrease Effects 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000011521 glass Substances 0.000 description 3
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 2
UGCSPKPEHQEOSR-UHFFFAOYSA-N 1,1,2,2-tetrachloro-1,2-difluoroethane Chemical compound FC(Cl)(Cl)C(F)(Cl)Cl UGCSPKPEHQEOSR-UHFFFAOYSA-N 0.000 description 2
AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 2
CYXIKYKBLDZZNW-UHFFFAOYSA-N 2-Chloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)CCl CYXIKYKBLDZZNW-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
UHTBGZCYOATXPS-UHFFFAOYSA-M aluminum;oxygen(2-);fluoride Chemical compound [O-2].[F-].[Al+3] UHTBGZCYOATXPS-UHFFFAOYSA-M 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
IZMHKHHRLNWLMK-UHFFFAOYSA-M chloridoaluminium Chemical compound Cl[Al] IZMHKHHRLNWLMK-UHFFFAOYSA-M 0.000 description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 2
229940099364 dichlorofluoromethane Drugs 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
239000005457 ice water Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 2
SLGOCMATMKJJCE-UHFFFAOYSA-N 1,1,1,2-tetrachloro-2,2-difluoroethane Chemical compound FC(F)(Cl)C(Cl)(Cl)Cl SLGOCMATMKJJCE-UHFFFAOYSA-N 0.000 description 1
BFJGKEZYSSAZTR-UHFFFAOYSA-N 1,1,1,2-tetrachloro-2,3,3,3-tetrafluoropropane Chemical class FC(F)(F)C(F)(Cl)C(Cl)(Cl)Cl BFJGKEZYSSAZTR-UHFFFAOYSA-N 0.000 description 1
BAMUEXIPKSRTBS-UHFFFAOYSA-N 1,1-dichloro-1,2,2,2-tetrafluoroethane Chemical compound FC(F)(F)C(F)(Cl)Cl BAMUEXIPKSRTBS-UHFFFAOYSA-N 0.000 description 1
YMRMDGSNYHCUCL-UHFFFAOYSA-N 1,2-dichloro-1,1,2-trifluoroethane Chemical compound FC(Cl)C(F)(F)Cl YMRMDGSNYHCUCL-UHFFFAOYSA-N 0.000 description 1
OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 1
DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 1
239000005935 Sulfuryl fluoride Substances 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
150000001348 alkyl chlorides Chemical class 0.000 description 1
LDDQLRUQCUTJBB-UHFFFAOYSA-N ammonium fluoride Chemical compound [NH4+].[F-] LDDQLRUQCUTJBB-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
KVBCYCWRDBDGBG-UHFFFAOYSA-N azane;dihydrofluoride Chemical compound [NH4+].F.[F-] KVBCYCWRDBDGBG-UHFFFAOYSA-N 0.000 description 1
238000010923 batch production Methods 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000005827 chlorofluoro hydrocarbons Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
OMRRUNXAWXNVFW-UHFFFAOYSA-N fluoridochlorine Chemical compound ClF OMRRUNXAWXNVFW-UHFFFAOYSA-N 0.000 description 1
NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
229910001506 inorganic fluoride Inorganic materials 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
238000011068 loading method Methods 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000003507 refrigerant Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
SFZCNBIFKDRMGX-UHFFFAOYSA-N sulfur hexafluoride Chemical compound FS(F)(F)(F)(F)F SFZCNBIFKDRMGX-UHFFFAOYSA-N 0.000 description 1
229960000909 sulfur hexafluoride Drugs 0.000 description 1
OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
LSJNBGSOIVSBBR-UHFFFAOYSA-N thionyl fluoride Chemical compound FS(F)=O LSJNBGSOIVSBBR-UHFFFAOYSA-N 0.000 description 1
XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine

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)

CS912633A 1990-08-28 1991-08-27 Process for preparing pentafluorodichloropropanes CS263391A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP2227502A JPH0784399B2 (ja)	1990-08-28	1990-08-28	ペンタフルオロジクロロプロパン中のクロロホルムの除去方法
JP2227501A JPH0784398B2 (ja)	1990-08-28	1990-08-28	ペンタフルオロジクロロプロパン類の製造方法

Publications (1)

Publication Number	Publication Date
CS263391A3 true CS263391A3 (en)	1992-04-15

Family

ID=26527712

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS912633A CS263391A3 (en)	1990-08-28	1991-08-27	Process for preparing pentafluorodichloropropanes

Country Status (11)

Country	Link
EP (1)	EP0473105B1 (de)
KR (1)	KR920004321A (de)
AT (1)	ATE119143T1 (de)
BR (1)	BR9103700A (de)
CA (1)	CA2049821A1 (de)
CS (1)	CS263391A3 (de)
DE (1)	DE69107732T2 (de)
DK (1)	DK0473105T3 (de)
ES (1)	ES2071878T3 (de)
PL (1)	PL291537A1 (de)
RU (1)	RU2029757C1 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0525066A (ja) *	1991-07-23	1993-02-02	Daikin Ind Ltd	１，１，１，２，２−ペンタフルオロ−３，３−ジクロロプロパン及び１，１，２，２，３−ペンタフルオロ−１，３−ジクロロプロパンの製造方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2462402A (en) *	1945-06-30	1949-02-22	Du Pont	Fluorinated hydrocarbons
BE638397A (de) *	1962-10-09
US3381042A (en) *	1967-01-27	1968-04-30	Squibb & Sons Inc	Process for preparing halogenated propanes

1991
- 1991-08-26 CA CA002049821A patent/CA2049821A1/en not_active Abandoned
- 1991-08-27 ES ES91114338T patent/ES2071878T3/es not_active Expired - Lifetime
- 1991-08-27 EP EP91114338A patent/EP0473105B1/de not_active Expired - Lifetime
- 1991-08-27 AT AT91114338T patent/ATE119143T1/de not_active IP Right Cessation
- 1991-08-27 DK DK91114338.6T patent/DK0473105T3/da active
- 1991-08-27 CS CS912633A patent/CS263391A3/cs unknown
- 1991-08-27 DE DE69107732T patent/DE69107732T2/de not_active Expired - Fee Related
- 1991-08-27 RU SU915001481A patent/RU2029757C1/ru active
- 1991-08-27 PL PL29153791A patent/PL291537A1/xx unknown
- 1991-08-28 KR KR1019910014951A patent/KR920004321A/ko not_active Withdrawn
- 1991-08-28 BR BR919103700A patent/BR9103700A/pt unknown

Also Published As

Publication number	Publication date
DE69107732T2 (de)	1995-08-24
PL291537A1 (en)	1992-04-06
DK0473105T3 (da)	1995-05-22
EP0473105B1 (de)	1995-03-01
DE69107732D1 (de)	1995-04-06
CA2049821A1 (en)	1992-03-01
KR920004321A (ko)	1992-03-27
ES2071878T3 (es)	1995-07-01
ATE119143T1 (de)	1995-03-15
RU2029757C1 (ru)	1995-02-27
EP0473105A1 (de)	1992-03-04
BR9103700A (pt)	1992-05-19

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JP3423314B2 (ja)	2003-07-07	クロロフルオロエーテル組成物およびそれらの製造
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