JPH0732879B2 - ハロゲン化炭化水素のフッ素化に使用したアンチモンを主成分とする触媒の回収方法 - Google Patents
ハロゲン化炭化水素のフッ素化に使用したアンチモンを主成分とする触媒の回収方法Info
- Publication number
- JPH0732879B2 JPH0732879B2 JP4014281A JP1428192A JPH0732879B2 JP H0732879 B2 JPH0732879 B2 JP H0732879B2 JP 4014281 A JP4014281 A JP 4014281A JP 1428192 A JP1428192 A JP 1428192A JP H0732879 B2 JPH0732879 B2 JP H0732879B2
- Authority
- JP
- Japan
- Prior art keywords
- antimony
- sbcl
- olefin
- temperature
- distillation
- 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.)
- Expired - Lifetime
Links
- 229910052787 antimony Inorganic materials 0.000 title claims abstract description 41
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 title claims abstract description 40
- 239000003054 catalyst Substances 0.000 title claims abstract description 36
- 238000003682 fluorination reaction Methods 0.000 title claims abstract description 15
- 150000008282 halocarbons Chemical class 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 36
- 238000011084 recovery Methods 0.000 title claims description 6
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims abstract description 25
- 238000004821 distillation Methods 0.000 claims abstract description 24
- 239000000460 chlorine Substances 0.000 claims abstract description 23
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 16
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 150000001336 alkenes Chemical class 0.000 claims description 20
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 15
- 150000002894 organic compounds Chemical class 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 9
- 239000002243 precursor Substances 0.000 claims description 8
- 238000005660 chlorination reaction Methods 0.000 claims description 6
- 239000012141 concentrate Substances 0.000 claims 1
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 abstract description 2
- 238000009835 boiling Methods 0.000 description 14
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 10
- ZDINGUUTWDGGFF-UHFFFAOYSA-N antimony(5+) Chemical compound [Sb+5] ZDINGUUTWDGGFF-UHFFFAOYSA-N 0.000 description 7
- 238000004064 recycling Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000012429 reaction media Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- -1 pentavalent antimony halide Chemical class 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- FAWGZAFXDJGWBB-UHFFFAOYSA-N antimony(3+) Chemical compound [Sb+3] FAWGZAFXDJGWBB-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 150000001462 antimony Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000012958 reprocessing Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- FRCHKSNAZZFGCA-UHFFFAOYSA-N 1,1-dichloro-1-fluoroethane Chemical compound CC(F)(Cl)Cl FRCHKSNAZZFGCA-UHFFFAOYSA-N 0.000 description 1
- LGXVIGDEPROXKC-UHFFFAOYSA-N 1,1-dichloroethene Chemical group ClC(Cl)=C LGXVIGDEPROXKC-UHFFFAOYSA-N 0.000 description 1
- FQAMAOOEZDRHHB-UHFFFAOYSA-N 1,2,2-trichloro-1,1-difluoroethane Chemical compound FC(F)(Cl)C(Cl)Cl FQAMAOOEZDRHHB-UHFFFAOYSA-N 0.000 description 1
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
- BHNZEZWIUMJCGF-UHFFFAOYSA-N 1-chloro-1,1-difluoroethane Chemical compound CC(F)(F)Cl BHNZEZWIUMJCGF-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
- CYXIKYKBLDZZNW-UHFFFAOYSA-N 2-Chloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)CCl CYXIKYKBLDZZNW-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001463 antimony compounds Chemical class 0.000 description 1
- GUNJVIDCYZYFGV-UHFFFAOYSA-K antimony trifluoride Chemical compound F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012025 fluorinating agent Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910001506 inorganic fluoride Inorganic materials 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/90—Regeneration or reactivation
- B01J23/92—Regeneration or reactivation of catalysts comprising metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/28—Regeneration or reactivation
- B01J27/32—Regeneration or reactivation of catalysts comprising compounds of halogens
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G30/00—Compounds of antimony
- C01G30/006—Halides
- C01G30/007—Halides of binary type SbX3 or SbX5 with X representing a halogen, or mixed of the type SbX3X'2 with X,X' representing different halogens
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9101031A FR2671984B1 (fr) | 1991-01-30 | 1991-01-30 | Procede pour la recuperation des catalyseurs a base d'antimoine utilises pour la fluoration d'hydrocarbures halogenes. |
| FR9101031 | 1991-01-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06165944A JPH06165944A (ja) | 1994-06-14 |
| JPH0732879B2 true JPH0732879B2 (ja) | 1995-04-12 |
Family
ID=9409193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4014281A Expired - Lifetime JPH0732879B2 (ja) | 1991-01-30 | 1992-01-29 | ハロゲン化炭化水素のフッ素化に使用したアンチモンを主成分とする触媒の回収方法 |
Country Status (13)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2098906A1 (en) * | 1997-08-29 | 2009-09-09 | Sharp Kabushiki Kaisha | Liquid crystal display device |
| FR2806077B1 (fr) * | 2000-03-07 | 2004-01-30 | Solvay | Procede pour l'obtention d'un hydrofluoroalcane epure, hydrofluoroalcane epure, utilisation de l'hydrofluoroalcane et methode d'analyse d'un hydrofluoroalcane |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2110797A1 (de) * | 1971-03-06 | 1972-09-28 | Hoechst Ag | Verfahren zur Rueckgewinnung von SbCl5 aus zur Fluorierung von chlorierten Kohlenwasserstoffen verwendeten Kontaktloesungen |
| JPS5221297A (en) * | 1975-08-13 | 1977-02-17 | Daikin Ind Ltd | Recovering method of antimony pentachloride from used catalyst contain ing antimony |
| US4722774A (en) * | 1987-02-25 | 1988-02-02 | Chemical & Metal Industries, Inc. | Recovery or arsenic and antimony from spent antimony catalyst |
| DE3929263A1 (de) * | 1989-09-02 | 1991-03-07 | Kali Chemie Ag | Verfahren zur aufarbeitung von antimonhalogenidkatalysatorloesungen |
-
1991
- 1991-01-30 FR FR9101031A patent/FR2671984B1/fr not_active Expired - Fee Related
-
1992
- 1992-01-21 AT AT92400155T patent/ATE92368T1/de not_active IP Right Cessation
- 1992-01-21 TW TW081100408A patent/TW221815B/zh active
- 1992-01-21 EP EP92400155A patent/EP0497657B1/fr not_active Expired - Lifetime
- 1992-01-21 ES ES92400155T patent/ES2043476T3/es not_active Expired - Lifetime
- 1992-01-21 DE DE92400155T patent/DE69200009T2/de not_active Expired - Fee Related
- 1992-01-29 IE IE920297A patent/IE65277B1/en not_active IP Right Cessation
- 1992-01-29 AU AU10546/92A patent/AU650510B2/en not_active Ceased
- 1992-01-29 US US07/827,775 patent/US5198199A/en not_active Expired - Fee Related
- 1992-01-29 CA CA002060263A patent/CA2060263A1/fr not_active Abandoned
- 1992-01-29 JP JP4014281A patent/JPH0732879B2/ja not_active Expired - Lifetime
- 1992-01-30 KR KR1019920001364A patent/KR950005751B1/ko not_active Expired - Fee Related
- 1992-01-30 MX MX9200402A patent/MX9200402A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2060263A1 (fr) | 1992-07-31 |
| AU1054692A (en) | 1992-08-06 |
| US5198199A (en) | 1993-03-30 |
| FR2671984B1 (fr) | 1994-04-08 |
| IE65277B1 (en) | 1995-10-18 |
| TW221815B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1994-03-21 |
| ATE92368T1 (de) | 1993-08-15 |
| EP0497657A1 (fr) | 1992-08-05 |
| JPH06165944A (ja) | 1994-06-14 |
| KR950005751B1 (ko) | 1995-05-30 |
| KR920014518A (ko) | 1992-08-25 |
| ES2043476T3 (es) | 1993-12-16 |
| EP0497657B1 (fr) | 1993-08-04 |
| IE920297A1 (en) | 1992-07-29 |
| MX9200402A (es) | 1992-07-01 |
| DE69200009T2 (de) | 1994-01-20 |
| FR2671984A1 (fr) | 1992-07-31 |
| AU650510B2 (en) | 1994-06-23 |
| DE69200009D1 (de) | 1993-09-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6689924B1 (en) | Liquid phase catalytic fluorination of hydrochlorocarbon and hydrochlorofluorocarbon | |
| JP3130657B2 (ja) | １−クロロ−１，１，３，３，３− ペンタフルオロプロパン及び１，１，１，３，３，３−ヘキサフルオロプロパンの製造法 | |
| EP0494994B1 (en) | Fluorocarbon purification process | |
| JP4222451B2 (ja) | 弗化水素の回収方法 | |
| US9701599B2 (en) | Process for producing 2,3,3,3-tetrafluoropropene | |
| KR100235757B1 (ko) | 퍼클로로에틸렌으로 부터 하이드로플루오로카본을 제조하는 일단계방법 | |
| WO2002018305A2 (en) | Production and use of octafluoropropane | |
| JP3886168B2 (ja) | １−クロロ−１− フルオロエタン及び／又は１，１−ジフルオロエタンの製造方法 | |
| JP3518169B2 (ja) | １，１，１，３，３−ペンタフルオロプロパンの製造方法 | |
| JP2828775B2 (ja) | １，１―ジクロロ―１―フルオロエタンの製造法 | |
| US5780691A (en) | Process for producing 1,1,1,2,3,3,3,-heptafluoroprane | |
| JPH0732879B2 (ja) | ハロゲン化炭化水素のフッ素化に使用したアンチモンを主成分とする触媒の回収方法 | |
| JP2005097245A (ja) | ヘキサフルオロエタンの製造方法およびその用途 | |
| JPH0665117A (ja) | １，１，１，２−テトラフルオロエタンの製造法 | |
| JP2001240566A (ja) | １，１，１−トリフルオロ−２，２−ジクロロエタンの製造方法 | |
| JPH1017502A (ja) | １，１，１，３，３−ペンタフルオロプロパンの製造方法 | |
| EP0592711B1 (en) | Method for the purification of 1,1,1,2-tetrafluoroethane | |
| WO1998050327A1 (en) | A process for the production of a hydrofluorocarbon and use of a catalyst therefor | |
| JPH08198783A (ja) | １，１，１，３，３−ペンタフルオロブタンの製造方法 | |
| MXPA98002850A (en) | Process to recover acid fluorhidr |