JP4178301B2 - 貴金属をベースとする触媒上での塩素の注入を伴なう芳香族化合物の水素化方法 - Google Patents
貴金属をベースとする触媒上での塩素の注入を伴なう芳香族化合物の水素化方法 Download PDFInfo
- Publication number
- JP4178301B2 JP4178301B2 JP16759096A JP16759096A JP4178301B2 JP 4178301 B2 JP4178301 B2 JP 4178301B2 JP 16759096 A JP16759096 A JP 16759096A JP 16759096 A JP16759096 A JP 16759096A JP 4178301 B2 JP4178301 B2 JP 4178301B2
- Authority
- JP
- Japan
- Prior art keywords
- chlorine
- catalyst
- feedstock
- feed
- noble metal
- 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
- 239000000460 chlorine Substances 0.000 title claims description 44
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 title claims description 41
- 229910052801 chlorine Inorganic materials 0.000 title claims description 41
- 239000003054 catalyst Substances 0.000 title claims description 29
- 238000005984 hydrogenation reaction Methods 0.000 title claims description 18
- 150000001491 aromatic compounds Chemical class 0.000 title claims description 17
- 229910000510 noble metal Inorganic materials 0.000 title claims description 11
- 238000002347 injection Methods 0.000 title description 9
- 239000007924 injection Substances 0.000 title description 9
- 238000000034 method Methods 0.000 claims description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 14
- 239000011593 sulfur Substances 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 9
- 229910052697 platinum Inorganic materials 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 239000002994 raw material Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229960001701 chloroform Drugs 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 150000002894 organic compounds Chemical class 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 claims description 2
- 229950011008 tetrachloroethylene Drugs 0.000 claims description 2
- 230000000694 effects Effects 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000003350 kerosene Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000006477 desulfuration reaction Methods 0.000 description 3
- 230000023556 desulfurization Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- DGABKXLVXPYZII-UHFFFAOYSA-N Hyodeoxycholic acid Natural products C1C(O)C2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 DGABKXLVXPYZII-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000011066 ex-situ storage Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- DGABKXLVXPYZII-SIBKNCMHSA-N hyodeoxycholic acid Chemical compound C([C@H]1[C@@H](O)C2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 DGABKXLVXPYZII-SIBKNCMHSA-N 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- -1 polycyclic aromatic compounds Chemical class 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B31/00—Reduction in general
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/44—Hydrogenation of the aromatic hydrocarbons
- C10G45/46—Hydrogenation of the aromatic hydrocarbons characterised by the catalyst used
- C10G45/52—Hydrogenation of the aromatic hydrocarbons characterised by the catalyst used containing platinum group metals or compounds thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9507726 | 1995-06-27 | ||
| FR9507726A FR2736063B1 (fr) | 1995-06-27 | 1995-06-27 | Procede d'hydrogenation d'aromatiques avec injection de chlore sur des catalyseurs a base de metal noble |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH0912486A JPH0912486A (ja) | 1997-01-14 |
| JPH0912486A5 JPH0912486A5 (enExample) | 2004-07-15 |
| JP4178301B2 true JP4178301B2 (ja) | 2008-11-12 |
Family
ID=9480438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16759096A Expired - Lifetime JP4178301B2 (ja) | 1995-06-27 | 1996-06-27 | 貴金属をベースとする触媒上での塩素の注入を伴なう芳香族化合物の水素化方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US5789637A (enExample) |
| EP (1) | EP0751204B1 (enExample) |
| JP (1) | JP4178301B2 (enExample) |
| KR (1) | KR100450474B1 (enExample) |
| DE (1) | DE69615464T2 (enExample) |
| ES (1) | ES2164851T3 (enExample) |
| FR (1) | FR2736063B1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2736063B1 (fr) * | 1995-06-27 | 1997-08-14 | Inst Francais Du Petrole | Procede d'hydrogenation d'aromatiques avec injection de chlore sur des catalyseurs a base de metal noble |
| DE69730539T2 (de) | 1996-06-10 | 2005-06-23 | Hitachi, Ltd. | Abgasreinigungsanlage einer Brennkraftmaschine und Katalysator zum Reinigen des Abgases einer Brennkraftmaschine |
| FR2765586B1 (fr) * | 1997-07-02 | 2003-09-05 | Inst Francais Du Petrole | Procede de transformation, par hydrogenation catalytique, d'une base huile en huile blanche medicinale |
| FR2778341B1 (fr) * | 1998-05-07 | 2000-06-09 | Inst Francais Du Petrole | Catalyseur a base d'un metal noble du groupe viii contenant du bore et/ou du silicium et son utilisation en hydrotraitement de charge hydrocarbonees |
| FR2778342B1 (fr) | 1998-05-07 | 2000-06-16 | Inst Francais Du Petrole | Catalyseur utilisable dans l'hydrogenation des composes aromatiques dans une charge hydrocarbonnee contenant des composes soufres |
| US6013847A (en) * | 1998-12-31 | 2000-01-11 | Phillips Petroleum Company | Hydrogenation of benzene in the presence of water |
| FR2795420B1 (fr) * | 1999-06-25 | 2001-08-03 | Inst Francais Du Petrole | Procede d'hydrotraitement d'un distillat moyen dans deux zones successives comprenant une zone intermediaire de stripage de l'effluent de la premiere zone avec condensation des produits lourds sortant en tete du strippeur |
| FR2800638B1 (fr) * | 1999-11-10 | 2002-01-18 | Inst Francais Du Petrole | Catalyseur fluore comprenant un element du groupe viii et un element du groupe viib et son utilisation pour l'hydrogenation de composes aromatiques en presence de composes soufres |
| FR2800640B1 (fr) * | 1999-11-10 | 2002-01-18 | Inst Francais Du Petrole | Catalyseur fluore comprenant un metal du groupe viii et un metal du groupe iib et son utilisation pour l'hydrogenation de composes aromatiques en presence de composes soufres |
| ES2274771T3 (es) | 1999-11-10 | 2007-06-01 | Institut Francais Du Petrole | Catalizador clorado y fluorado que comprende un metal del grupo viii y un metal adicional y su uso en la hidrogenacion de composiciones aromaticas. |
| FR2800639B1 (fr) * | 1999-11-10 | 2002-01-18 | Inst Francais Du Petrole | Catalyseur bimetallique comprenant du fluor et son utilisation pour l'hydrogenation des composes aromatiques en presence de composes soufres |
| FR2800637B1 (fr) * | 1999-11-10 | 2002-01-18 | Inst Francais Du Petrole | Catalyseur fluore comprenant un metal du groupe viii et un metal du groupe ib et son utilisation pour l'hydrogenation de composes aromatiques en presence de composes soufres |
| EP1432758B1 (en) | 2001-09-25 | 2008-11-26 | ExxonMobil Chemical Patents Inc. | Plasticised polyvinyl chloride |
| US9828571B2 (en) | 2015-06-05 | 2017-11-28 | Illinois Tool Works, Inc. | Heavy duty laundry detergent |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3639227A (en) * | 1969-11-17 | 1972-02-01 | Chevron Res | Chloride addition during hydrogenation |
| US3816299A (en) * | 1973-04-30 | 1974-06-11 | Union Oil Co | Hydrogenation process |
| FR2240905B1 (enExample) * | 1973-08-16 | 1980-01-04 | Inst Francais Du Petrole | |
| US4110198A (en) * | 1977-02-03 | 1978-08-29 | Uop Inc. | Process for hydrocracking hydrocarbons |
| FR2736063B1 (fr) * | 1995-06-27 | 1997-08-14 | Inst Francais Du Petrole | Procede d'hydrogenation d'aromatiques avec injection de chlore sur des catalyseurs a base de metal noble |
-
1995
- 1995-06-27 FR FR9507726A patent/FR2736063B1/fr not_active Expired - Lifetime
-
1996
- 1996-06-21 DE DE69615464T patent/DE69615464T2/de not_active Expired - Lifetime
- 1996-06-21 ES ES96401381T patent/ES2164851T3/es not_active Expired - Lifetime
- 1996-06-21 EP EP96401381A patent/EP0751204B1/fr not_active Expired - Lifetime
- 1996-06-27 JP JP16759096A patent/JP4178301B2/ja not_active Expired - Lifetime
- 1996-06-27 US US08/671,501 patent/US5789637A/en not_active Expired - Lifetime
- 1996-06-27 KR KR1019960024371A patent/KR100450474B1/ko not_active Expired - Lifetime
-
1998
- 1998-06-26 US US09/105,002 patent/US5986154A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2736063B1 (fr) | 1997-08-14 |
| EP0751204A1 (fr) | 1997-01-02 |
| FR2736063A1 (fr) | 1997-01-03 |
| EP0751204B1 (fr) | 2001-09-26 |
| DE69615464T2 (de) | 2002-04-25 |
| KR100450474B1 (ko) | 2004-12-04 |
| KR970001284A (ko) | 1997-01-24 |
| JPH0912486A (ja) | 1997-01-14 |
| US5986154A (en) | 1999-11-16 |
| ES2164851T3 (es) | 2002-03-01 |
| US5789637A (en) | 1998-08-04 |
| DE69615464D1 (de) | 2001-10-31 |
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