TWI225427B - Process for the hydrogenation of phenyl acetylene in a styrene-containing medium with the aid of a catalyst - Google Patents
Process for the hydrogenation of phenyl acetylene in a styrene-containing medium with the aid of a catalyst Download PDFInfo
- Publication number
- TWI225427B TWI225427B TW088103411A TW88103411A TWI225427B TW I225427 B TWI225427 B TW I225427B TW 088103411 A TW088103411 A TW 088103411A TW 88103411 A TW88103411 A TW 88103411A TW I225427 B TWI225427 B TW I225427B
- Authority
- TW
- Taiwan
- Prior art keywords
- styrene
- catalyst
- phenylacetylene
- weight
- reactor
- Prior art date
Links
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 title claims abstract description 122
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 title claims abstract description 83
- 238000000034 method Methods 0.000 title claims abstract description 17
- 239000003054 catalyst Substances 0.000 title claims description 46
- 238000005984 hydrogenation reaction Methods 0.000 title abstract description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 62
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 27
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 21
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
- 229910052763 palladium Inorganic materials 0.000 description 10
- 238000011049 filling Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 150000001345 alkine derivatives Chemical class 0.000 description 2
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical group C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000002079 cooperative effect Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002815 nickel Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 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
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- -1 ethylbenzyl Chemical group 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/163—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation
- C07C7/167—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation for removal of compounds containing a triple carbon-to-carbon bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL1009014A NL1009014C2 (nl) | 1998-04-28 | 1998-04-28 | Werkwijze voor de hydrogenering van fenylacetyleen in een styreenbevattend medium met behulp van een katalysator. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI225427B true TWI225427B (en) | 2004-12-21 |
Family
ID=19767035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW088103411A TWI225427B (en) | 1998-04-28 | 1999-03-05 | Process for the hydrogenation of phenyl acetylene in a styrene-containing medium with the aid of a catalyst |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6747181B1 (https=) |
| EP (1) | EP1076639B1 (https=) |
| JP (1) | JP2002512991A (https=) |
| KR (1) | KR100588178B1 (https=) |
| CN (1) | CN1160284C (https=) |
| AR (1) | AR018193A1 (https=) |
| AT (1) | ATE243670T1 (https=) |
| AU (1) | AU754614B2 (https=) |
| BR (1) | BR9910031A (https=) |
| CA (1) | CA2330036A1 (https=) |
| DE (1) | DE69909081T2 (https=) |
| ES (1) | ES2203117T3 (https=) |
| ID (1) | ID26285A (https=) |
| NL (1) | NL1009014C2 (https=) |
| NO (1) | NO991982L (https=) |
| PT (1) | PT1076639E (https=) |
| SA (1) | SA99191307B1 (https=) |
| TW (1) | TWI225427B (https=) |
| WO (1) | WO1999055648A1 (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040030207A1 (en) * | 2002-08-08 | 2004-02-12 | Catalytic Distillation Technologies | Selective hydrogenation of acetylenes |
| US7105711B2 (en) * | 2003-07-31 | 2006-09-12 | Fina Technology, Inc. | Process for the selective hydrogenation of phenylacetylene |
| US7276163B2 (en) * | 2003-10-01 | 2007-10-02 | Ceramem Corporation | Membrane devices with controlled transmembrane pressure and method of use |
| US7408089B2 (en) | 2004-03-19 | 2008-08-05 | Catalytic Distillation Technologies | Ni catalyst, process for making catalysts and selective hydrogenation process |
| US20060084830A1 (en) | 2004-10-20 | 2006-04-20 | Catalytic Distillation Technologies | Selective hydrogenation process and catalyst |
| US20060173224A1 (en) * | 2005-02-01 | 2006-08-03 | Catalytic Distillation Technologies | Process and catalyst for selective hydrogenation of dienes and acetylenes |
| KR100843595B1 (ko) * | 2005-10-31 | 2008-07-03 | 주식회사 엘지화학 | 스티렌계 모노머의 정제 방법 및 장치 |
| US7696395B2 (en) * | 2007-06-08 | 2010-04-13 | Fina Technology, Inc. | Dehydrogenation and polymerization process |
| US8524969B2 (en) * | 2008-07-22 | 2013-09-03 | Fina Technology, Inc. | Dehydrogenation reactions of hydrocarbons to alkenes |
| CN101475437B (zh) * | 2008-12-18 | 2012-05-23 | 中国石油化工股份有限公司 | 苯乙烯存在下除苯乙炔的方法 |
| CN101475438B (zh) * | 2008-12-18 | 2012-05-23 | 中国石油化工股份有限公司 | 苯乙烯存在下苯乙炔选择加氢的方法 |
| CN101475439B (zh) | 2008-12-18 | 2012-05-09 | 中国石油化工股份有限公司 | 苯乙烯存在下采用复合床进行苯乙炔选择加氢的方法 |
| EP2223987A1 (en) * | 2009-02-17 | 2010-09-01 | ISP Marl GmbH | Purification of an aromatic fraction containing acetylenes by selective hydrogenation of the acetylenes |
| TWI486330B (zh) * | 2009-12-18 | 2015-06-01 | China Petro Chemical Technologydevelopment Company | Selective Hydrogenation of Phenylene Acetylene in the Presence of |
| CN102649660A (zh) * | 2011-02-25 | 2012-08-29 | 中国石油化工股份有限公司 | 苯乙烯存在下除苯乙炔的方法 |
| CN102391425B (zh) * | 2011-08-31 | 2012-10-24 | 五行材料科技（江苏）有限公司 | 一种相容剂及其制备方法和含有该相容剂的聚苯醚/聚酰胺共混合金及其制备方法 |
| CN102887810B (zh) * | 2012-10-18 | 2015-04-22 | 广东新华粤华德科技有限公司 | 一种裂解c8馏分中苯乙炔选择性加氢反应方法 |
| CN107954814A (zh) * | 2016-10-14 | 2018-04-24 | 中国石油化工股份有限公司 | 碳八馏份中苯乙炔选择加氢的方法 |
| CN115283019B (zh) * | 2022-10-09 | 2023-02-14 | 吉林领创生物科技有限公司 | 多孔金属有机框架负载Ni复合催化剂的制备方法及应用 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2399514A (en) * | 1941-11-22 | 1946-04-30 | United Gas Improvement Co | Process for decolorizing light oil fractions by selective hydrogenation |
| US2511453A (en) * | 1947-08-13 | 1950-06-13 | Du Pont | Catalyst and process for carrying out hydrogenation reactions |
| JPS4536226B1 (https=) * | 1963-08-04 | 1970-11-18 | ||
| DE1926503C3 (de) * | 1968-05-27 | 1975-03-20 | Maruzen Oil Co. Ltd., Osaka (Japan) | Verfahren zu selektiven Hydrierung von mehrfach ungesättigten Kohlenwasserstoffen |
| DE1806080A1 (de) * | 1968-10-30 | 1970-05-21 | Basf Ag | Verfahren zur Herstellung von Styrol |
| JPS5535368B2 (https=) * | 1972-05-26 | 1980-09-12 | ||
| US3793388A (en) * | 1972-05-30 | 1974-02-19 | Phillips Petroleum Co | Selective hydrogenation of acetylene from olefins with a nickel on alumina catalyst |
| US4734540A (en) * | 1986-12-22 | 1988-03-29 | Uop Inc. | Catalyst for the selective hydrogenation of polyunsaturated organics |
| JPS63291643A (ja) * | 1987-05-25 | 1988-11-29 | Nippon Kayaku Co Ltd | フエニルアセチレン類の選択水素添加反応用触媒 |
| US5156816A (en) * | 1990-10-04 | 1992-10-20 | Fina Technology, Inc. | System for purifying styrene monomer feedstock using ethylbenzene dehydrogenation waste gas |
| BR9107322A (pt) * | 1991-10-10 | 1996-01-02 | Dow Chemical Co | Processo para a hidrogenação seletiva de composto s de acetileno aromático |
| FR2767722B1 (fr) * | 1997-08-29 | 1999-12-31 | Inst Francais Du Petrole | Nouveau catalyseur utilisable dans les reactions de transformation de composes organiques |
-
1998
- 1998-04-28 NL NL1009014A patent/NL1009014C2/nl not_active IP Right Cessation
-
1999
- 1999-03-05 TW TW088103411A patent/TWI225427B/zh not_active IP Right Cessation
- 1999-04-14 SA SA99191307A patent/SA99191307B1/ar unknown
- 1999-04-21 AR ARP990101831A patent/AR018193A1/es not_active Application Discontinuation
- 1999-04-26 BR BR9910031-2A patent/BR9910031A/pt not_active IP Right Cessation
- 1999-04-26 JP JP2000545809A patent/JP2002512991A/ja active Pending
- 1999-04-26 KR KR1020007011903A patent/KR100588178B1/ko not_active Expired - Fee Related
- 1999-04-26 ID IDW20002184A patent/ID26285A/id unknown
- 1999-04-26 WO PCT/NL1999/000245 patent/WO1999055648A1/en not_active Ceased
- 1999-04-26 ES ES99917235T patent/ES2203117T3/es not_active Expired - Lifetime
- 1999-04-26 PT PT99917235T patent/PT1076639E/pt unknown
- 1999-04-26 DE DE69909081T patent/DE69909081T2/de not_active Expired - Fee Related
- 1999-04-26 AT AT99917235T patent/ATE243670T1/de not_active IP Right Cessation
- 1999-04-26 CA CA002330036A patent/CA2330036A1/en not_active Abandoned
- 1999-04-26 EP EP99917235A patent/EP1076639B1/en not_active Expired - Lifetime
- 1999-04-26 NO NO991982A patent/NO991982L/no unknown
- 1999-04-26 AU AU35394/99A patent/AU754614B2/en not_active Ceased
- 1999-04-26 CN CNB998055255A patent/CN1160284C/zh not_active Expired - Fee Related
-
2000
- 2000-10-06 US US09/680,308 patent/US6747181B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1298376A (zh) | 2001-06-06 |
| ID26285A (id) | 2000-12-14 |
| EP1076639A1 (en) | 2001-02-21 |
| DE69909081D1 (de) | 2003-07-31 |
| NL1009014C2 (nl) | 1999-10-29 |
| BR9910031A (pt) | 2000-12-26 |
| AR018193A1 (es) | 2001-10-31 |
| AU754614B2 (en) | 2002-11-21 |
| DE69909081T2 (de) | 2004-05-13 |
| NO991982D0 (no) | 1999-04-26 |
| ES2203117T3 (es) | 2004-04-01 |
| KR100588178B1 (ko) | 2006-06-08 |
| KR20010043040A (ko) | 2001-05-25 |
| PT1076639E (pt) | 2003-11-28 |
| NO991982L (no) | 1999-10-29 |
| WO1999055648A1 (en) | 1999-11-04 |
| US6747181B1 (en) | 2004-06-08 |
| CA2330036A1 (en) | 1999-11-04 |
| AU3539499A (en) | 1999-11-16 |
| CN1160284C (zh) | 2004-08-04 |
| EP1076639B1 (en) | 2003-06-25 |
| SA99191307B1 (ar) | 2006-10-03 |
| ATE243670T1 (de) | 2003-07-15 |
| JP2002512991A (ja) | 2002-05-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |