KR960029296A - 유기 황-함유 화합물로 함침된 금속 촉매를 이용하여 방향족 화합물이 풍부한 탄화수소 유분내의 디올레핀 및 임의의 올레핀을 수소화하는 방법 - Google Patents
유기 황-함유 화합물로 함침된 금속 촉매를 이용하여 방향족 화합물이 풍부한 탄화수소 유분내의 디올레핀 및 임의의 올레핀을 수소화하는 방법 Download PDFInfo
- Publication number
- KR960029296A KR960029296A KR1019960001668A KR19960001668A KR960029296A KR 960029296 A KR960029296 A KR 960029296A KR 1019960001668 A KR1019960001668 A KR 1019960001668A KR 19960001668 A KR19960001668 A KR 19960001668A KR 960029296 A KR960029296 A KR 960029296A
- Authority
- KR
- South Korea
- Prior art keywords
- sulfur
- catalyst
- containing compound
- group
- weight
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 14
- 239000003054 catalyst Substances 0.000 title claims abstract 10
- 150000001875 compounds Chemical class 0.000 title claims abstract 10
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract 6
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract 6
- 125000001741 organic sulfur group Chemical group 0.000 title claims 4
- 239000004215 Carbon black (E152) Substances 0.000 title claims 2
- 150000001336 alkenes Chemical class 0.000 title 1
- 150000001993 dienes Chemical class 0.000 title 1
- 239000002184 metal Substances 0.000 title 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 7
- 239000011593 sulfur Substances 0.000 claims abstract 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract 6
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract 5
- 239000003921 oil Substances 0.000 claims abstract 4
- 229910052763 palladium Inorganic materials 0.000 claims abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract 2
- 125000003118 aryl group Chemical group 0.000 claims abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052794 bromium Inorganic materials 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 2
- 239000001257 hydrogen Substances 0.000 claims abstract 2
- 239000007791 liquid phase Substances 0.000 claims abstract 2
- 150000005673 monoalkenes Chemical class 0.000 claims abstract 2
- 229920000098 polyolefin Polymers 0.000 claims abstract 2
- 239000002904 solvent Substances 0.000 claims 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 2
- -1 aryl sulfide Chemical compound 0.000 claims 2
- RVEZZJVBDQCTEF-UHFFFAOYSA-N sulfenic acid Chemical class SO RVEZZJVBDQCTEF-UHFFFAOYSA-N 0.000 claims 2
- 150000003573 thiols Chemical class 0.000 claims 2
- WVUYNWCKWXAGLA-UHFFFAOYSA-N (ethoxydisulfanyl)oxyethane Chemical compound CCOSSOCC WVUYNWCKWXAGLA-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 150000002169 ethanolamines Chemical class 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 150000002898 organic sulfur compounds Chemical class 0.000 claims 1
- 229920001021 polysulfide Polymers 0.000 claims 1
- 239000005077 polysulfide Substances 0.000 claims 1
- 150000008117 polysulfides Polymers 0.000 claims 1
- 239000000377 silicon dioxide Substances 0.000 claims 1
- 150000005846 sugar alcohols Polymers 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 150000007970 thio esters Chemical class 0.000 claims 1
- 150000003568 thioethers Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
-
- 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
- C10G45/32—Selective hydrogenation of the diolefin or acetylene compounds
- C10G45/34—Selective hydrogenation of the diolefin or acetylene compounds characterised by the catalyst used
- C10G45/40—Selective hydrogenation of the diolefin or acetylene compounds characterised by the catalyst used containing platinum group metals or compounds thereof
-
- 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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/20—Sulfiding
-
- 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
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)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
Description
Claims (12)
- 방향족 전환도가 최대 0.15중량%로 제한되며, 브롬 수가 생성물 100g 당 100 내지 10000mg인 모노올레핀계 탄화수소 및 폴리올레핀계 및/또는 아세틸렌계 탄화수소를 함유하는 방향족 탄화수소 유분의 선택적인 고효율 수소화 방법에 있어서, 0.05 내지 1중량%(촉매의 중량을 기준함)의 황을 투입하기 위해 하나 이상의 유기 황-함유 화합물로 활성화 단계 이전에 촉매를 전처리하고, 적어도 부분적으로 액상 내에 존재하는 상기 유분을 수소 존재하에 20 내지 250℃의 온도, 4~50bar의 압력, 0.2~25 h-1의 GHSV 및 H2/모노올레핀+폴리올레핀 및/또는 아세틸렌의 비가 0.3 내지 100인 조건하에서 0.1 내지 1중량%(지지체를 기준함)의 팔라듐을 함유하는 촉매와 접촉하는 수소화 대역 내로 통과시키는 것을 특징으로 하는 방법.
- 제1항에 있어서, 지지체가 알루미나, 실리카 및 실리카-알루미나로 구성되는 군으로부터 선택됨을 특징으로 하는 방법.
- 제1항 또는 제2항에 있어서, 유기 황-함유 화합물이 반응기 내의 촉매를 활성화하는 처리 조건하에서 분해가능한 유기 황-함유 화합물로 구성되는 군으로부터 선택됨을 특징으로 하는 방법.
- 전술한 항 중 어느 한 항에 있어서, 유기 황-함유 화합물이 유기 알킬 또는 아릴 설파이드, 유기 알킬아릴 또는 아릴알킬 설파이드, 티올, 티올디아졸, 유기 티오산, 티오아미드, 티오에스테르, 티오페놀, 메르캅토-알콜, 모노티오글리콜 및 티오에테르로 구성되는 군으로부터 선택됨을 특징으로 하는 방법.
- 전술한 항 중 어느 한 항에 있어서, 황-함유 화합물이 2,2-디티오비스-에탄올, 디테르티오도데실 폴리 설파이드 및 디에톡시디설파이드로 구성되는 군으로부터 선택됨을 특징으로 하는 방법.
- 전술한 항 중 어느 한 항에 있어서, 황-함유 화합물이 가솔린 및 탄화수소 유분으로 구성되는 군으로부터 선택된 용매에 의해 희석됨을 특징으로 하는 방법.
- 제1항 내지 제5항 중 어느 한 항에 있어서, 황-함유 화합물이 알콜, 알데히드, 케톤, 에테르, 에스테르, 폴리알콜, 산, 다중산 및 글리콜로 구성되는 군으로부터 선택된 용매에 의해 희석됨을 특징으로 하는 방법.
- 제1항 내지 제5항 중 어느 한 항에 있어서, 황-함유 화합물이 용매인 물에 의해서 희석됨을 특징으로 하는 방법.
- 전술한 항 중 어느 한 항에 있어서, 촉매가 0.05 내지 1중량%의 황을 포함함을 특징으로 하는 방법.
- 전술한 항 중 어느 한 항에 있어서, 촉매가 0.1 내지 0.4중량%의 황을 포함함을 특징으로 하는 방법.
- 전술한 항 중 어느 한 항에 있어서, 수소화하려는 탄화수소 유분이 수소화 대역을 통과하기 전에, 수소 존재 하에서 하나 이상의 유기 황-화합물로 처리된 촉매가 20 내지 300℃의 온도, 1 내지 50bar의 압력 및 50~60 h-1의 GHSV의 수소화 대역 내에서 활성화되는 것을 특징으로 하는 방법.
- 전술한 항 중 어느 한 항에 있어서, 상기 수소화 방법을 50 내지 250℃의 온도, 4 내지 50bar의 압력 및 0.2 내지 25 h-1에서 안정한 GHSV에서 수행함을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9500977A FR2729968B1 (fr) | 1995-01-27 | 1995-01-27 | Procede d'hydrogenation des diolefines et eventuellement des olefines de coupes hydrocarbures riches en composes aromatiques sur des catalyseurs metalliques impregenes de composes organiques soufres |
FR95-00977 | 1995-01-27 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR960029296A true KR960029296A (ko) | 1996-08-17 |
KR100377055B1 KR100377055B1 (ko) | 2003-06-09 |
Family
ID=9475583
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019960001668A KR100377055B1 (ko) | 1995-01-27 | 1996-01-26 | 유기황함유화합물이함침된금속촉매를사용하여방향족화합물이농후한탄화수소유분내의디올레핀및임의의올레핀을수소화시키는방법 |
Country Status (4)
Country | Link |
---|---|
US (1) | US5821397A (ko) |
KR (1) | KR100377055B1 (ko) |
CN (1) | CN1056642C (ko) |
FR (1) | FR2729968B1 (ko) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100275661B1 (ko) * | 1997-12-30 | 2001-01-15 | 김영환 | 실리레이션을이용한감광막패턴형성방법 |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2730728B1 (fr) | 1995-02-21 | 1997-05-23 | Inst Francais Du Petrole | Procede de separation du p-xylene comportant un pretraitement par hydrogenation selective et par de la terre activee |
CN1097480C (zh) * | 1999-06-25 | 2003-01-01 | 中国石油化工集团公司 | 炔烃选择加氢催化剂 |
EP1277826A1 (en) * | 2001-07-18 | 2003-01-22 | ATOFINA Research | Hydrogenation and dehydrogenation processes and catalysts therefor |
DE10149631A1 (de) * | 2001-10-09 | 2003-04-10 | Basf Ag | Verfahren zur selektiven katalytischen Gasphasenhydrierung von Alkinen, Dienen, Alkeninen und/oder Polyenen |
JP5105296B2 (ja) * | 2005-12-02 | 2012-12-26 | エヌ・イーケムキャット株式会社 | 官能基選択的水素化触媒、及び官能基選択的水素化方法 |
CN101590437B (zh) * | 2008-05-29 | 2013-04-17 | 北京三聚环保新材料股份有限公司 | 加氢催化剂的器外预硫化方法 |
US8350106B2 (en) * | 2008-06-30 | 2013-01-08 | Uop Llc | Selective hydrogenation of unsaturated aliphatic hydrocarbons in predominantly aromatic streams |
US10988421B2 (en) | 2013-12-06 | 2021-04-27 | Exxonmobil Chemical Patents Inc. | Removal of bromine index-reactive compounds |
US9738572B2 (en) * | 2014-10-14 | 2017-08-22 | Uop Llc | Methods and apparatuses for selective hydrogenation of olefins |
CN115254117B (zh) * | 2022-08-19 | 2023-05-23 | 浙江师范大学 | 一种提高钴基催化剂上1,3-丁二烯加氢反应中单丁烯选择性的方法 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH462809A (de) * | 1964-06-03 | 1968-09-30 | Hoffmann La Roche | Verwendung von schwefelorganischen Verbindungen zur Erhöhung der Selektivität von Hydrierungskatalysatoren |
FR2337195A1 (fr) * | 1976-01-05 | 1977-07-29 | Inst Francais Du Petrole | Procede de traitement catalytique, en trois etapes, sous pression d'hydrogene de coupes lourdes tres fortement insaturees |
DE2803284A1 (de) * | 1977-01-31 | 1978-08-03 | Inst Francais Du Petrol | Katalytisches verfahren zur reformierung bzw. herstellung von aromatischen kohlenwasserstoffen |
FR2460989A1 (fr) * | 1979-07-06 | 1981-01-30 | Inst Francais Du Petrole | Procede de purification d'une coupe d'hydrocarbures aromatiques contenant des hydrocarbures insatures olefiniques et acetyleniques |
FR2664610A1 (fr) * | 1990-07-13 | 1992-01-17 | Inst Francais Du Petrole | Hydrogenation selective des essences de vapocraquage sur des catalyseurs a base d'un metal supporte dans lesquels un compose organique a ete incorpore avant chargement dans le reacteur. |
CA2092754C (en) * | 1992-05-01 | 1999-03-16 | Ronald Gordon Abbott | Isoparaffin-olefin alkylation |
FR2704865B1 (fr) * | 1993-05-06 | 1995-07-21 | Inst Francais Du Petrole | Procédé d'hydrogénation catalytique. |
FR2708596B1 (fr) * | 1993-07-30 | 1995-09-29 | Inst Francais Du Petrole | Procédé d'isomérisation d'oléfines externes en oléfines internes conjointement à l'hydrogénation des dioléfines. |
IT1265051B1 (it) * | 1993-08-06 | 1996-10-28 | Eniricerche Spa | Processo per l'alchilazione di idrocarburi alifatici con olefine |
-
1995
- 1995-01-27 FR FR9500977A patent/FR2729968B1/fr not_active Expired - Lifetime
-
1996
- 1996-01-26 KR KR1019960001668A patent/KR100377055B1/ko not_active IP Right Cessation
- 1996-01-27 CN CN96105567A patent/CN1056642C/zh not_active Expired - Lifetime
- 1996-01-29 US US08/593,410 patent/US5821397A/en not_active Expired - Lifetime
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100275661B1 (ko) * | 1997-12-30 | 2001-01-15 | 김영환 | 실리레이션을이용한감광막패턴형성방법 |
Also Published As
Publication number | Publication date |
---|---|
FR2729968A1 (fr) | 1996-08-02 |
CN1144836A (zh) | 1997-03-12 |
FR2729968B1 (fr) | 1997-04-11 |
KR100377055B1 (ko) | 2003-06-09 |
CN1056642C (zh) | 2000-09-20 |
US5821397A (en) | 1998-10-13 |
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