CA1117145A - Manufacture of halogenated compounds - Google Patents
Manufacture of halogenated compoundsInfo
- Publication number
- CA1117145A CA1117145A CA000311550A CA311550A CA1117145A CA 1117145 A CA1117145 A CA 1117145A CA 000311550 A CA000311550 A CA 000311550A CA 311550 A CA311550 A CA 311550A CA 1117145 A CA1117145 A CA 1117145A
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- chromium
- hydrogen fluoride
- trifluoroethylene
- range
- 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
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 claims abstract description 11
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 11
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 claims abstract description 9
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910000423 chromium oxide Inorganic materials 0.000 claims abstract description 7
- 229910021563 chromium fluoride Inorganic materials 0.000 claims abstract description 3
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 15
- VQWFNAGFNGABOH-UHFFFAOYSA-K chromium(iii) hydroxide Chemical compound [OH-].[OH-].[OH-].[Cr+3] VQWFNAGFNGABOH-UHFFFAOYSA-K 0.000 claims description 3
- 238000003682 fluorination reaction Methods 0.000 claims description 2
- 238000001354 calcination Methods 0.000 claims 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229910052804 chromium Inorganic materials 0.000 description 4
- 239000011651 chromium Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229910000792 Monel Inorganic materials 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-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 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical class FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000004812 organic fluorine compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
- C07C17/087—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated halogenated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB39088/77 | 1977-09-20 | ||
| GB3908877 | 1977-09-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1117145A true CA1117145A (en) | 1982-01-26 |
Family
ID=10407570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000311550A Expired CA1117145A (en) | 1977-09-20 | 1978-09-19 | Manufacture of halogenated compounds |
Country Status (14)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5500400A (en) * | 1993-12-09 | 1996-03-19 | Korea Institute Of Science And Technology | Catalyst for producing 1,1,1,2-tetrafluoroethane and method for preparing the same |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2712732C2 (de) * | 1977-03-23 | 1986-03-13 | Hoechst Ag, 6230 Frankfurt | Verfahren zur Herstellung von Oktafluorpropan |
| JPS5527139A (en) * | 1978-08-14 | 1980-02-27 | Daikin Ind Ltd | Preparation of tetrafluoroethane |
| DE3009760A1 (de) * | 1980-03-14 | 1981-09-24 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von hochreinen teilfluorierten aethanen |
| FR2501062A1 (fr) * | 1980-12-29 | 1982-09-10 | Ugine Kuhlmann | Catalyseurs de fluoruration en phase gazeuse de derives chlores aliphatiques, a base de microbilles d'oxyde de chrome, et procedes de fluoruration utilisant ces catalyseurs |
| DE3545625A1 (de) * | 1985-12-21 | 1987-06-25 | Dataprint Datendrucksysteme R | Wasserfreies fluessiges aufzeichnungsmaterial |
| IT1230779B (it) * | 1989-07-12 | 1991-10-29 | Ausimont Srl | Procedimento per preparare 1,1,1,2 tetrafluoroetano. |
| BE1004450A3 (fr) * | 1990-06-18 | 1992-11-24 | Solvay | Procede pour la fabrication du 1,1,1,2-tetrafluorethane. |
| FR2694556B1 (fr) * | 1992-08-05 | 1994-09-23 | Atochem Elf Sa | Procédé de purification du 1,1,1,2-tétrafluoroéthane. |
| US5750808A (en) * | 1995-07-11 | 1998-05-12 | E. I. Du Pont De Nemours And Company | Dehydrohalogenation processes |
| RU2243961C1 (ru) * | 2003-08-18 | 2005-01-10 | Федеральное государственное унитарное предприятие Российский научный центр "Прикладная химия" | Способ получения 1,1,1,2-тетрафторэтана |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2669590A (en) * | 1951-08-03 | 1954-02-16 | Allied Chem & Dye Corp | Production of fluorine compounds |
| US2855427A (en) * | 1955-05-24 | 1958-10-07 | American Potash & Chem Corp | Continuous process for preparation of pure methyl borate |
| GB1307224A (en) * | 1969-06-27 | 1973-02-14 | Ici Ltd | Chromium oxide catalyst |
| JPS4872105A (enrdf_load_stackoverflow) * | 1971-12-29 | 1973-09-29 | ||
| DE3009760A1 (de) * | 1980-03-14 | 1981-09-24 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von hochreinen teilfluorierten aethanen |
-
1978
- 1978-08-16 GB GB7833506A patent/GB2004539B/en not_active Expired
- 1978-08-23 GR GR57064A patent/GR64019B/el unknown
- 1978-08-24 ZA ZA00784828A patent/ZA784828B/xx unknown
- 1978-08-28 DE DE19782837515 patent/DE2837515A1/de active Granted
- 1978-08-29 NL NL7808881A patent/NL7808881A/xx not_active Application Discontinuation
- 1978-08-30 AU AU39367/78A patent/AU519072B2/en not_active Expired
- 1978-08-31 AR AR273526A patent/AR225276A1/es active
- 1978-09-15 BE BE190528A patent/BE870530A/xx not_active IP Right Cessation
- 1978-09-18 IT IT27797/78A patent/IT1098853B/it active
- 1978-09-18 JP JP11371378A patent/JPS5452012A/ja active Granted
- 1978-09-19 BR BR7806150A patent/BR7806150A/pt unknown
- 1978-09-19 FR FR7826787A patent/FR2403321A1/fr active Granted
- 1978-09-19 CA CA000311550A patent/CA1117145A/en not_active Expired
- 1978-09-20 ES ES473516A patent/ES473516A1/es not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5500400A (en) * | 1993-12-09 | 1996-03-19 | Korea Institute Of Science And Technology | Catalyst for producing 1,1,1,2-tetrafluoroethane and method for preparing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2837515A1 (de) | 1979-03-29 |
| AU519072B2 (en) | 1981-11-05 |
| DE2837515C2 (enrdf_load_stackoverflow) | 1989-06-29 |
| BR7806150A (pt) | 1979-04-17 |
| ZA784828B (en) | 1979-08-29 |
| JPS5452012A (en) | 1979-04-24 |
| FR2403321A1 (fr) | 1979-04-13 |
| BE870530A (fr) | 1979-03-15 |
| FR2403321B1 (enrdf_load_stackoverflow) | 1984-01-20 |
| GB2004539A (en) | 1979-04-04 |
| IT7827797A0 (it) | 1978-09-18 |
| AU3936778A (en) | 1980-03-06 |
| JPS6223728B2 (enrdf_load_stackoverflow) | 1987-05-25 |
| GR64019B (en) | 1980-01-18 |
| IT1098853B (it) | 1985-09-18 |
| GB2004539B (en) | 1982-02-10 |
| ES473516A1 (es) | 1979-05-01 |
| NL7808881A (nl) | 1979-03-22 |
| AR225276A1 (es) | 1982-03-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |