NO125479B - - Google Patents
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- Publication number
- NO125479B NO125479B NO3964/69A NO396469A NO125479B NO 125479 B NO125479 B NO 125479B NO 3964/69 A NO3964/69 A NO 3964/69A NO 396469 A NO396469 A NO 396469A NO 125479 B NO125479 B NO 125479B
- Authority
- NO
- Norway
- Prior art keywords
- catalyst
- compounds
- manganese
- chromium
- fluorination
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 claims description 37
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 24
- IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 claims description 18
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 claims description 18
- 238000003682 fluorination reaction Methods 0.000 claims description 18
- 229910052804 chromium Inorganic materials 0.000 claims description 15
- 239000011651 chromium Substances 0.000 claims description 15
- 229910052759 nickel Inorganic materials 0.000 claims description 14
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 12
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 12
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 230000004913 activation Effects 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 229910052748 manganese Inorganic materials 0.000 claims description 8
- 239000011572 manganese Substances 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 7
- 150000002816 nickel compounds Chemical class 0.000 claims description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 150000002222 fluorine compounds Chemical class 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 150000002736 metal compounds Chemical class 0.000 claims description 3
- 150000002823 nitrates Chemical class 0.000 claims description 3
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 2
- 150000001845 chromium compounds Chemical class 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 229910001512 metal fluoride Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- -1 oxygen halides Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 9
- 230000003197 catalytic effect Effects 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000007323 disproportionation reaction Methods 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 150000008282 halocarbons Chemical class 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005243 fluidization Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 229910001026 inconel Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 229910018487 Ni—Cr Inorganic materials 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004334 fluoridation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical class [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
- C07C17/04—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated halogenated hydrocarbons
-
- 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
- B01J27/06—Halogens; Compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
- C07C17/02—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/206—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/37—Preparation of halogenated hydrocarbons by disproportionation of halogenated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2229568 | 1968-10-10 | ||
| DK387569AA DK126161B (da) | 1968-07-25 | 1969-07-17 | Katalysator til fremstilling af chlorflourerede ethaner, der har høj symmetrigrad med hensyn til fordelingen af flouratomerne. |
| DK528669AA DK138673B (da) | 1968-10-10 | 1969-10-03 | Katalysator til fremstilling af chlorfluorerede ethaner. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO125479B true NO125479B (fr) | 1972-09-18 |
Family
ID=27221891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3964/69A NO125479B (fr) | 1968-10-10 | 1969-10-04 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3787331A (fr) |
| JP (1) | JPS5512297B1 (fr) |
| BE (1) | BE740090A (fr) |
| BR (1) | BR6913221D0 (fr) |
| CH (1) | CH525710A (fr) |
| DE (1) | DE1950804C3 (fr) |
| DK (1) | DK138673B (fr) |
| ES (1) | ES372331A1 (fr) |
| FR (1) | FR2020296A1 (fr) |
| GB (1) | GB1283386A (fr) |
| IL (1) | IL33144A (fr) |
| NL (1) | NL173393C (fr) |
| NO (1) | NO125479B (fr) |
| SE (1) | SE361135B (fr) |
| YU (1) | YU32815B (fr) |
| ZA (1) | ZA697069B (fr) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1202350B (it) * | 1975-12-22 | 1989-02-09 | Allied Chem | Procedimento per la produzione di composti organici clorofluorurati |
| US4110406A (en) * | 1976-12-21 | 1978-08-29 | Allied Chemical Corporation | Preparation of 1-chloro-2-trifluoromethyl-3,3,3-trifluoropropene from isobutylene |
| JPS573247U (fr) * | 1980-06-04 | 1982-01-08 | ||
| EP0203807B1 (fr) | 1985-05-28 | 1988-09-28 | E.I. Du Pont De Nemours And Company | Procédé catalytique de transhalogénation de fluoro-oléfines |
| JPS6226239A (ja) * | 1985-05-28 | 1987-02-04 | イ−・アイ・デユポン・デ・ニモアス・アンド・カンパニ− | フルオロオレフインの接触ハロゲン交換法 |
| US5262574A (en) * | 1987-03-09 | 1993-11-16 | Ausimont S.P.A. | Process for preparing 1,1,1-trifluoro-2,2-dichloroethane by hydrofluorination in the presence of catalysts |
| US5276224A (en) * | 1987-03-09 | 1994-01-04 | Ausimont S.P.A. | Process for preparing 1,1,1-trifluoro-2,2-dichloroethane by hydrofluorination in the presence of catalysts |
| IT1202652B (it) * | 1987-03-09 | 1989-02-09 | Ausimont Spa | Processo per la preparazione di 1,1,1-trifluoro-2,2-dicloroetano mediante idrofluorurazione in presenza di catalizzatori |
| US4861744A (en) * | 1987-06-16 | 1989-08-29 | Laroche Chemicals, Inc. | Process for preparing a fluorination catalyst and the catalyst prepared by the process |
| US4766260A (en) * | 1987-07-07 | 1988-08-23 | E. I. Du Pont De Nemours And Company | Gas-phase fluorination process |
| US4766259A (en) * | 1987-08-13 | 1988-08-23 | E. I. Du Pont De Nemours And Company | Gas-phase fluorination process |
| JPH0788326B2 (ja) * | 1987-11-26 | 1995-09-27 | 旭硝子株式会社 | １，１−ジクロロ−１，２，２，２−テトラフルオロエタンの製造方法 |
| US4798818A (en) * | 1987-11-27 | 1989-01-17 | Dow Corning Corporation | Catalyst composition and process for its preparation |
| CA1310335C (fr) * | 1988-02-12 | 1992-11-17 | Leo E. Manzer | Procede de fluoration en phase gazeuse |
| US4922037A (en) * | 1988-02-24 | 1990-05-01 | E. I. Du Pont De Nemours And Company | Gas-phase fluorination process |
| US4902838A (en) * | 1988-12-28 | 1990-02-20 | E. I. Du Pont De Nemours And Company | Isomerization of saturated fluorohydrocarbons |
| IT1230779B (it) * | 1989-07-12 | 1991-10-29 | Ausimont Srl | Procedimento per preparare 1,1,1,2 tetrafluoroetano. |
| US5030372A (en) * | 1990-07-31 | 1991-07-09 | E. I. Du Pont De Nemours And Company | Catalytic equilibration to improve the relative yield of selected halocarbons |
| WO1992002476A1 (fr) | 1990-07-31 | 1992-02-20 | E.I. Du Pont De Nemours And Company | Equilibrage catalytique d'halocarbones selectionnes |
| FR2669022B1 (fr) * | 1990-11-13 | 1992-12-31 | Atochem | Procede de fabrication du tetrafluoro-1,1,1,2-ethane. |
| DE4222517A1 (de) * | 1992-07-09 | 1994-01-13 | Bayer Ag | Verfahren zur Herstellung von Halogenaromaten |
| FR2700766B1 (fr) * | 1993-01-27 | 1995-03-24 | Atochem Elf Sa | Procédé de fluoration de perchloréthylène ou du pentachloréthane. |
| FR2700770B1 (fr) * | 1993-01-27 | 1995-03-24 | Atochem Elf Sa | Procédé de fabrication du 1,1,1,2-tétrafluoro-2-chloroéthane et du pentafluoroéthane. |
| US6274780B1 (en) * | 1995-07-11 | 2001-08-14 | E. I. Du Pont De Nemours And Company | Catalysts for halogenated hydrocarbon processing and their preparation and use |
| US5841007A (en) * | 1996-04-12 | 1998-11-24 | Korea Institute Of Science And Technology | Process for manufacturing 1,1,1,2-tetrafluoroethane |
| FR2757085B1 (fr) * | 1996-12-13 | 1999-01-22 | Atochem Elf Sa | Catalyseurs massiques a base de chrome et de nickel pour la fluoration en phase gazeuse d'hydrocarbures halogenes |
| FR2828193B1 (fr) * | 2001-08-03 | 2004-04-02 | Atofina | Nouveau procede de preparation du 1,1,1,-trifluoro-2,2-dichloroethane |
| US20070032688A1 (en) * | 2002-08-02 | 2007-02-08 | Beatrice Boussand | Process for preparing 1,1,1-trifluoro-2, 2-dichloroethane |
| EP1502906A1 (fr) * | 2003-07-31 | 2005-02-02 | Solvay Solexis S.p.A. | Procédé d'activation de catalyseurs à base de AlF3 et procédé d'isomérisation d'hydrochlorofluorocarbones |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2744148A (en) * | 1952-02-04 | 1956-05-01 | Dow Chemical Co | Process for fluorination of haloalkanes using a hydrogen fluoride activated catalyst containing alumina, a metal fluoride and basic aluminum fluoride |
| DE1468438A1 (de) * | 1963-01-22 | 1968-12-19 | Onoda Cement Co Ltd | Verfahren zur Herstellung von Fluor-Derivaten halogenierter Kohlenwasserstoffe |
| US3294852A (en) * | 1963-07-11 | 1966-12-27 | Edison Soc | Process for preparing fluorine containing organic compounds |
-
1969
- 1969-10-03 NL NLAANVRAGE6914962,A patent/NL173393C/xx not_active IP Right Cessation
- 1969-10-03 DK DK528669AA patent/DK138673B/da not_active IP Right Cessation
- 1969-10-04 NO NO3964/69A patent/NO125479B/no unknown
- 1969-10-06 FR FR6934003A patent/FR2020296A1/fr not_active Withdrawn
- 1969-10-07 ZA ZA697069A patent/ZA697069B/xx unknown
- 1969-10-07 US US00864519A patent/US3787331A/en not_active Expired - Lifetime
- 1969-10-08 IL IL33144A patent/IL33144A/en unknown
- 1969-10-08 GB GB49478/69A patent/GB1283386A/en not_active Expired
- 1969-10-09 SE SE13877/69A patent/SE361135B/xx unknown
- 1969-10-09 ES ES372331A patent/ES372331A1/es not_active Expired
- 1969-10-09 DE DE1950804A patent/DE1950804C3/de not_active Expired
- 1969-10-10 BR BR213221/69A patent/BR6913221D0/pt unknown
- 1969-10-10 CH CH1526769A patent/CH525710A/de not_active IP Right Cessation
- 1969-10-10 YU YU2546/69A patent/YU32815B/xx unknown
- 1969-10-10 BE BE740090D patent/BE740090A/xx not_active IP Right Cessation
- 1969-10-11 JP JP8147169A patent/JPS5512297B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IL33144A0 (en) | 1969-12-31 |
| BR6913221D0 (pt) | 1973-01-04 |
| ZA697069B (en) | 1971-01-27 |
| CH525710A (de) | 1972-07-31 |
| NL173393C (nl) | 1984-01-16 |
| BE740090A (fr) | 1970-04-10 |
| DE1950804A1 (de) | 1970-10-29 |
| DE1950804B2 (de) | 1978-03-30 |
| DK138673B (da) | 1978-10-16 |
| FR2020296A1 (fr) | 1970-07-10 |
| US3787331A (en) | 1974-01-22 |
| YU32815B (en) | 1975-08-31 |
| NL6914962A (fr) | 1970-04-14 |
| DE1950804C3 (de) | 1979-03-15 |
| YU254669A (en) | 1975-02-28 |
| IL33144A (en) | 1973-06-29 |
| DK138673C (fr) | 1979-03-05 |
| JPS5512297B1 (fr) | 1980-04-01 |
| NL173393B (nl) | 1983-08-16 |
| SE361135B (fr) | 1973-10-22 |
| GB1283386A (en) | 1972-07-26 |
| ES372331A1 (es) | 1972-02-16 |
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