JP2006509829A5 - - Google Patents
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- JP2006509829A5 JP2006509829A5 JP2004563715A JP2004563715A JP2006509829A5 JP 2006509829 A5 JP2006509829 A5 JP 2006509829A5 JP 2004563715 A JP2004563715 A JP 2004563715A JP 2004563715 A JP2004563715 A JP 2004563715A JP 2006509829 A5 JP2006509829 A5 JP 2006509829A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- stream
- catalyst
- acidic catalyst
- 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.)
- Pending
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- 239000003054 catalyst Substances 0.000 claims 45
- 238000000034 method Methods 0.000 claims 43
- 229910052751 metal Inorganic materials 0.000 claims 25
- 239000002184 metal Substances 0.000 claims 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 24
- 230000002378 acidificating effect Effects 0.000 claims 24
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 14
- 150000002739 metals Chemical class 0.000 claims 13
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims 12
- 238000010828 elution Methods 0.000 claims 12
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims 11
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims 10
- 229910044991 metal oxide Inorganic materials 0.000 claims 10
- 150000004706 metal oxides Chemical class 0.000 claims 10
- 239000000203 mixture Substances 0.000 claims 10
- 238000005984 hydrogenation reaction Methods 0.000 claims 9
- 239000007788 liquid Substances 0.000 claims 7
- BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 claims 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 6
- 238000005336 cracking Methods 0.000 claims 5
- 230000003647 oxidation Effects 0.000 claims 5
- 238000007254 oxidation reaction Methods 0.000 claims 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims 4
- 239000003999 initiator Substances 0.000 claims 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 4
- 239000007787 solid Substances 0.000 claims 4
- 239000011973 solid acid Substances 0.000 claims 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 229910000420 cerium oxide Inorganic materials 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 229910003455 mixed metal oxide Inorganic materials 0.000 claims 3
- 239000002808 molecular sieve Substances 0.000 claims 3
- 230000001590 oxidative effect Effects 0.000 claims 3
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 239000000377 silicon dioxide Substances 0.000 claims 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims 3
- 229910052723 transition metal Inorganic materials 0.000 claims 3
- 229910000314 transition metal oxide Inorganic materials 0.000 claims 3
- 150000003624 transition metals Chemical class 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 239000004927 clay Substances 0.000 claims 2
- 229910052570 clay Inorganic materials 0.000 claims 2
- 229910017052 cobalt Inorganic materials 0.000 claims 2
- 239000010941 cobalt Substances 0.000 claims 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 2
- -1 dimethylphenyl Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052763 palladium Inorganic materials 0.000 claims 2
- 229910052697 platinum Inorganic materials 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 claims 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims 2
- GQNOPVSQPBUJKQ-UHFFFAOYSA-N 1-hydroperoxyethylbenzene Chemical compound OOC(C)C1=CC=CC=C1 GQNOPVSQPBUJKQ-UHFFFAOYSA-N 0.000 claims 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 claims 1
- 239000003377 acid catalyst Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical group [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 230000007704 transition Effects 0.000 claims 1
- 229910001928 zirconium oxide Inorganic materials 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/320,237 US6984761B2 (en) | 2002-12-16 | 2002-12-16 | Co-production of phenol, acetone, α-methylstyrene and propylene oxide, and catalyst therefor |
| PCT/US2003/040283 WO2004058672A1 (en) | 2002-12-16 | 2003-12-16 | Co-production of phenol, acetone, alpha-methylstyrene and propylene oxide, and catalyst therefor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006509829A JP2006509829A (ja) | 2006-03-23 |
| JP2006509829A5 true JP2006509829A5 (enExample) | 2007-02-08 |
Family
ID=32506828
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004563715A Pending JP2006509829A (ja) | 2002-12-16 | 2003-12-16 | フェノール、アセトン、α−メチルスチレン及び酸化プロピレンのコプロダクション及びその触媒 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6984761B2 (enExample) |
| EP (1) | EP1575888B1 (enExample) |
| JP (1) | JP2006509829A (enExample) |
| KR (1) | KR101084379B1 (enExample) |
| CN (2) | CN1726176A (enExample) |
| AT (1) | ATE483674T1 (enExample) |
| AU (1) | AU2003297321A1 (enExample) |
| DE (1) | DE60334493D1 (enExample) |
| TW (1) | TWI310027B (enExample) |
| WO (1) | WO2004058672A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7285512B2 (en) * | 2004-08-31 | 2007-10-23 | Exxonmobile Research And Engineering Company | Selective hydrodesulfurization catalyst |
| US7455762B2 (en) * | 2004-08-31 | 2008-11-25 | Exxonmobil Research And Engineering Company | Selective hydrodesulfurization process |
| US8189615B2 (en) * | 2004-12-23 | 2012-05-29 | Nokia Corporation | Method and apparatus for communicating scheduling information from a UE to a radio access network |
| ES2261080B1 (es) * | 2005-04-19 | 2007-12-16 | Universidad Politecnica De Valencia | Procedimiento y catalizadores para la expoxidacion de compuestos olefinicos en presencia de oxigeno. |
| US7452841B2 (en) * | 2005-09-23 | 2008-11-18 | Eastman Chemical Company | Catalysts selective for the preparation of mixed ketones from a mixture of carboxylic acids |
| US20100063329A1 (en) * | 2006-05-16 | 2010-03-11 | John Charles Saukaitis | Method for decomposing di(phenylalkyl)peroxides to produce hydroxybenzenes and phenylalkenes using solid catalysts |
| JP2010517933A (ja) * | 2006-08-03 | 2010-05-27 | エクソンモービル・ケミカル・パテンツ・インク | アルキル芳香族化合物の酸化法 |
| US7417003B2 (en) * | 2006-12-29 | 2008-08-26 | Uop Llc | Solid acid catalyst and process for decomposition of cumene hydroperoxide |
| CN102227393B (zh) * | 2008-12-01 | 2015-02-18 | 三井化学株式会社 | 烯烃的制造方法 |
| SG174387A1 (en) * | 2009-03-16 | 2011-11-28 | Mitsui Chemicals Inc | Process for production of olefins |
| KR101403517B1 (ko) * | 2010-12-01 | 2014-06-10 | 주식회사 엘지화학 | 알파 메틸 스티렌의 제조방법 |
| KR101403518B1 (ko) | 2010-12-21 | 2014-06-10 | 주식회사 엘지화학 | 알파 메틸 스티렌의 제조방법 |
| KR101447255B1 (ko) * | 2011-07-22 | 2014-10-07 | 주식회사 엘지화학 | 페놀, 아세톤 및 알파 메틸 스티렌의 제조방법 |
| KR101476376B1 (ko) * | 2011-07-15 | 2014-12-26 | 주식회사 엘지화학 | 페놀, 아세톤 및 알파 메틸 스티렌의 제조방법 |
| WO2013012203A2 (ko) * | 2011-07-15 | 2013-01-24 | 주식회사 엘지화학 | 쿠밀 알코올의 제조 방법 및 페놀, 아세톤, 및 알파 메틸 스티렌의 제조방법 |
| KR101431122B1 (ko) * | 2011-08-12 | 2014-08-19 | 주식회사 엘지화학 | 페놀, 아세톤 및 알파 메틸 스티렌의 제조방법 |
| KR101476375B1 (ko) * | 2011-09-02 | 2014-12-26 | 주식회사 엘지화학 | 페놀, 아세톤 및 알파 메틸 스티렌의 제조방법 |
| WO2013058877A1 (en) | 2011-10-18 | 2013-04-25 | Exxonmobil Chemical Patents Inc. | Process for co-producing of propylene oxide and phenol |
| WO2017118887A1 (en) * | 2016-01-05 | 2017-07-13 | Sabic Global Technologies B.V. | Systems and methods for the co-production of hydrogen and alkylene oxides |
| CN112079691A (zh) * | 2020-09-17 | 2020-12-15 | 吉化集团油脂化工有限公司 | 提升苯酚产品质量的方法 |
| RU2750718C1 (ru) * | 2020-12-04 | 2021-07-01 | федеральное государственное бюджетное образовательное учреждение высшего образования "Казанский национальный исследовательский технологический университет" (ФГБОУ ВО "КНИТУ") | Способ разложения гидропероксида изопропилбензола с получением диметилфенилкарбинола |
| US11858874B2 (en) | 2020-12-21 | 2024-01-02 | Lg Chem, Ltd. | Method for preparing alpha-methylstyrene |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2757209A (en) * | 1951-04-26 | 1956-07-31 | Allied Chem & Dye Corp | Recovery of phenol and alphamethylstyrene from cumene oxidation reaction mixtures |
| US2854487A (en) * | 1955-04-12 | 1958-09-30 | Distillers Co Yeast Ltd | Process for the manufacture of carbinols |
| BE657838A (enExample) | 1964-01-07 | 1965-06-30 | ||
| US3403193A (en) * | 1965-06-28 | 1968-09-24 | Halcon International Inc | Process for the co-production of a styrene and a di-olefin |
| SU462812A1 (ru) * | 1972-03-28 | 1975-03-05 | Предприятие П/Я Р-6235 | Способ совместного получени фенола, ацетона и -метилстирола |
| JPS56140935A (en) | 1980-04-03 | 1981-11-04 | Sumitomo Chem Co Ltd | Preparation of styrene compound |
| US4358618A (en) * | 1981-06-22 | 1982-11-09 | Allied Corporation | Decomposition of cumene oxidation product |
| JPS5916843A (ja) | 1982-07-20 | 1984-01-28 | Mitsui Toatsu Chem Inc | 芳香族アルコ−ルの連続製造法 |
| JPS60174737A (ja) * | 1984-02-22 | 1985-09-09 | Mitsui Petrochem Ind Ltd | 芳香族アルコ−ルの製造法 |
| US4853197A (en) * | 1987-06-04 | 1989-08-01 | Uop | Crystalline metal aluminophosphates |
| JP2544745B2 (ja) * | 1987-10-13 | 1996-10-16 | 三菱化学株式会社 | α−メチルスチレンの製造方法 |
| JPH02231442A (ja) * | 1988-11-28 | 1990-09-13 | Mitsui Petrochem Ind Ltd | フェノールの製造方法 |
| JP2593212B2 (ja) * | 1988-11-30 | 1997-03-26 | 三井石油化学工業株式会社 | クメンの製造方法 |
| CA2003925C (en) * | 1988-11-28 | 1999-11-23 | Shintaro Araki | Preparation of cumene through alkylation of an aromatic compound and preparation of phenol through cumene |
| US5245090A (en) * | 1992-09-11 | 1993-09-14 | Aristech Chemical Corporation | Two-stage cleavage of cumene hydroperoxide |
| US5371305A (en) * | 1992-12-31 | 1994-12-06 | Hercules Incorporated | Process for producing phenol from cumene |
| US5463136A (en) * | 1994-12-22 | 1995-10-31 | Shell Oil Company | Cumene hydroperoxide cleavage process |
| JP3769050B2 (ja) * | 1995-07-07 | 2006-04-19 | 三井化学株式会社 | フェノールの製造方法 |
| WO1998027030A1 (en) | 1996-12-17 | 1998-06-25 | Alliedsignal Inc. | Process for the production of alpha methylstyrenes |
| AU6167498A (en) * | 1997-02-11 | 1998-08-26 | E.I. Du Pont De Nemours And Company | Hydroperoxide decomposition process |
| KR100584829B1 (ko) | 1998-02-17 | 2006-05-29 | 셀 인터나쵸나아레 레사아치 마아츠샤피 비이부이 | 스티렌의 제조방법 |
| US5905178A (en) * | 1998-04-20 | 1999-05-18 | Catalytic Distillation Technologies | Removal of α-methyl styrene from cumene |
| US5932751A (en) * | 1998-06-23 | 1999-08-03 | Arco Chemical Technology, L.P. | Epoxidation catalyst and process |
| US6169215B1 (en) * | 1999-03-25 | 2001-01-02 | Mobil Oil Corporation | Production of phenol |
| US6169216B1 (en) * | 1999-04-22 | 2001-01-02 | Mobil Oil Corporation | Production of phenol |
| US6297406B1 (en) * | 1999-08-03 | 2001-10-02 | Mobil Oil Corporation | Production of phenol |
| US6114551A (en) * | 1999-10-04 | 2000-09-05 | Mobil Oil Corporation | Olefin epoxidation catalysts |
| US6410804B1 (en) * | 1999-12-21 | 2002-06-25 | Exxon Mobil Oil Corporation | Production of phenol using reactive distillation |
-
2002
- 2002-12-16 US US10/320,237 patent/US6984761B2/en not_active Expired - Fee Related
-
2003
- 2003-12-16 WO PCT/US2003/040283 patent/WO2004058672A1/en not_active Ceased
- 2003-12-16 CN CNA2003801061712A patent/CN1726176A/zh active Pending
- 2003-12-16 DE DE60334493T patent/DE60334493D1/de not_active Expired - Lifetime
- 2003-12-16 AT AT03814132T patent/ATE483674T1/de not_active IP Right Cessation
- 2003-12-16 AU AU2003297321A patent/AU2003297321A1/en not_active Abandoned
- 2003-12-16 KR KR1020057010980A patent/KR101084379B1/ko not_active Expired - Fee Related
- 2003-12-16 TW TW092135625A patent/TWI310027B/zh not_active IP Right Cessation
- 2003-12-16 EP EP03814132A patent/EP1575888B1/en not_active Expired - Lifetime
- 2003-12-16 JP JP2004563715A patent/JP2006509829A/ja active Pending
- 2003-12-16 CN CN2010105394660A patent/CN102060653A/zh active Pending
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