MX2012000175A - Proceso para la preparacion de fenol y ciclohexanona. - Google Patents
Proceso para la preparacion de fenol y ciclohexanona.Info
- Publication number
- MX2012000175A MX2012000175A MX2012000175A MX2012000175A MX2012000175A MX 2012000175 A MX2012000175 A MX 2012000175A MX 2012000175 A MX2012000175 A MX 2012000175A MX 2012000175 A MX2012000175 A MX 2012000175A MX 2012000175 A MX2012000175 A MX 2012000175A
- Authority
- MX
- Mexico
- Prior art keywords
- cyclohexylbenzene
- cyclohexanone
- phenol
- alkylation
- zeolite
- Prior art date
Links
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title abstract 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 abstract 4
- 239000010457 zeolite Substances 0.000 abstract 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- 229910021536 Zeolite Inorganic materials 0.000 abstract 2
- 230000029936 alkylation Effects 0.000 abstract 2
- 238000005804 alkylation reaction Methods 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 230000003197 catalytic effect Effects 0.000 abstract 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 abstract 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 abstract 2
- 239000003446 ligand Substances 0.000 abstract 2
- 239000011148 porous material Substances 0.000 abstract 2
- 238000003786 synthesis reaction Methods 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 238000010504 bond cleavage reaction Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 230000007017 scission Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/74—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition with simultaneous hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. cumene hydroperoxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Se describe un proceso para la preparación de fenol y ciclohexanona, que comprende: a. la síntesis de ciclohexilbenceno por hidroalquilización de benceno por el contacto del hidrógeno o por la alquilización de benceno con ciclohexeno usando las zeolitas Y; b. la oxidación aerobia selectiva de ciclohexilbenceno al hidroperóxido correspondiente catalizado por los derivados de N-hidroxi en presencia de solventes polares; y c. la división del hidroperóxido de ciclohexilbenceno al fenol y ciclohexanona por los catalizadores ácidos homogéneos o heterogéneos; caracterizado porque la síntesis de ciclohexilbenceno ocurre en presencia de un sistema catalítico que comprende una zeolita Y y un ligando inorgánico en donde la zeolita Y tiene una estructura cristalina con aberturas que consisten de (12) tetraédros y el ligando inorgánico es y-alúmina, y en donde la composición catalítica es caracterizada por un volumen de poros, obtenido agregando las fracciones de mesoporosidad y macroporosidad, mayor o igual a 0.7 cm/g, en donde por lo menos 30% del volumen consiste de poros con un diámetro mayor de 100 nanómetros.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2009A001145A IT1395594B1 (it) | 2009-06-29 | 2009-06-29 | Processo per la preparazione di fenolo e cicloesanone |
| PCT/IB2010/001540 WO2011001244A1 (en) | 2009-06-29 | 2010-06-23 | Process for the preparation of phenol and cyclohexanone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2012000175A true MX2012000175A (es) | 2012-05-23 |
Family
ID=41508866
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2012000175A MX2012000175A (es) | 2009-06-29 | 2010-06-23 | Proceso para la preparacion de fenol y ciclohexanona. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8598388B2 (es) |
| EP (1) | EP2448889B1 (es) |
| JP (1) | JP2012532119A (es) |
| CN (1) | CN102548936A (es) |
| AR (1) | AR078229A1 (es) |
| BR (1) | BRPI1011672A2 (es) |
| ES (1) | ES2424264T3 (es) |
| IT (1) | IT1395594B1 (es) |
| MX (1) | MX2012000175A (es) |
| PL (1) | PL2448889T3 (es) |
| RU (1) | RU2012101712A (es) |
| WO (1) | WO2011001244A1 (es) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8519194B2 (en) | 2009-02-26 | 2013-08-27 | Exxonmobil Chemical Patents Inc. | Process for producing cyclohexylbenzene |
| EP2435390B1 (en) | 2009-05-26 | 2016-08-17 | ExxonMobil Chemical Patents Inc. | Transalkylation of polycyclohexylbenzenes |
| WO2012145029A2 (en) * | 2011-04-19 | 2012-10-26 | Exxonmobil Chemical Patents Inc. | Process for producing phenol |
| US9321710B2 (en) | 2010-01-25 | 2016-04-26 | Exxonmobil Chemical Patents Inc. | Process for producing phenol |
| CN102958898B (zh) | 2010-08-25 | 2015-05-20 | 埃克森美孚化学专利公司 | 酯的制备方法 |
| US8921610B2 (en) | 2010-09-14 | 2014-12-30 | Exxonmobil Chemical Patents Inc. | Oxidation of alkylbenzenes |
| WO2012067711A1 (en) * | 2010-11-16 | 2012-05-24 | Exxonmobil Chemical Patents Inc. | Process for producing phenol |
| US9233887B2 (en) | 2010-12-21 | 2016-01-12 | Exxonmobil Chemical Patents Inc. | Process for producing a monocycloalkyl-substituted aromatic compound |
| EP2675772B1 (en) * | 2011-02-18 | 2015-09-16 | ExxonMobil Chemical Patents Inc. | Process for producing cyclohexylbenzene |
| CN103476751B (zh) * | 2011-03-28 | 2016-03-09 | 埃克森美孚化学专利公司 | 生产氢过氧化环己基苯的方法 |
| US9388102B2 (en) | 2011-04-19 | 2016-07-12 | Exxonmobil Chemical Patents Inc. | Process for producing phenol |
| US8946484B2 (en) * | 2011-04-19 | 2015-02-03 | Exxonmobil Chemical Patents Inc. | Method for producing phenol and/or cyclohexanone |
| JP5793792B2 (ja) * | 2011-04-19 | 2015-10-14 | エクソンモービル ケミカル パテンツ インコーポレイテッド | フェノールの製造方法 |
| WO2012145028A2 (en) | 2011-04-19 | 2012-10-26 | Exxonmobil Chemical Patents Inc. | Process for producing phenol |
| US9388103B2 (en) | 2011-09-23 | 2016-07-12 | Exxonmobil Chemical Patents Inc. | Process for producing phenol |
| US9067870B2 (en) | 2011-09-23 | 2015-06-30 | Exxonmobil Chemical Patents Inc. | Process for producing phenol |
| US9249078B2 (en) | 2011-10-07 | 2016-02-02 | Exxonmobil Chemical Patents Inc. | Mixed metal oxide catalysts and use thereof |
| US9108893B2 (en) | 2011-10-17 | 2015-08-18 | Exxonmobil Chemical Patents Inc. | Process for producing cyclohexylbenzene |
| WO2013109348A1 (en) * | 2012-01-18 | 2013-07-25 | Exxonmobil Chemical Patents Inc. | Process for producing phenol |
| US8940941B2 (en) | 2012-12-06 | 2015-01-27 | Exxonmobil Chemical Patents Inc. | Process for producing phenol and method for regenerating catalyst deactivated in the process |
| US9663418B2 (en) | 2013-03-04 | 2017-05-30 | Exxonmobil Chemical Patents Inc. | System and process for making cyclohexylbenzene |
| EP2964354B1 (en) * | 2013-03-04 | 2018-05-30 | ExxonMobil Chemical Patents Inc. | System and process for making phenol and/or cyclohexanone |
| CN103483156B (zh) * | 2013-08-29 | 2015-05-20 | 中国化学赛鼎宁波工程有限公司 | 一种苯联产环己酮和苯酚的系统及其方法 |
| CN105636692A (zh) | 2013-10-18 | 2016-06-01 | 埃克森美孚化学专利公司 | 包括加氢烷基化催化剂的活化的加氢烷基化方法和苯酚与环己酮的制备方法 |
| SG11201700443WA (en) | 2014-08-15 | 2017-02-27 | Exxonmobil Chemical Patents Inc | Process for making cyclohexanone |
| WO2016025218A1 (en) | 2014-08-15 | 2016-02-18 | Exxonmobil Chemical Patents Inc. | Process and system for making cyclohexanone |
| US9938218B2 (en) | 2014-08-15 | 2018-04-10 | Exxonmobil Chemical Patents Inc. | Process and system for making cyclohexanone |
| US9926254B2 (en) * | 2014-08-15 | 2018-03-27 | Exxonmobil Chemical Patents Inc. | Process and system for making cyclohexanone |
| WO2016025217A1 (en) | 2014-08-15 | 2016-02-18 | Exxonmobil Chemical Patents Inc. | Process and system for making cyclohexanone |
| WO2016053583A1 (en) | 2014-09-30 | 2016-04-07 | Exxonmobil Chemical Patents Inc. | Process for making cyclohexanone |
| US20230357103A1 (en) * | 2020-11-13 | 2023-11-09 | Eneos Corporation | Cyclohexylbenzene production method and cyclohexylbenzene composition using same |
| CN115106115B (zh) * | 2021-03-19 | 2023-11-03 | 中国石油大学(华东) | 一种烷烃制丙酮的方法 |
| CN115894193B (zh) * | 2021-09-30 | 2024-05-03 | 中国石油化工股份有限公司 | 一种氢过氧化物酸分解的方法 |
| CN116618068B (zh) * | 2022-02-14 | 2025-12-30 | 中国石油化工股份有限公司 | 用于氢过氧化物酸解的催化剂及其制备方法和应用 |
| CN115591566B (zh) * | 2022-05-12 | 2023-09-19 | 北京化工大学 | 一种负载型铜基催化剂及其制备方法和应用 |
| CN115368935A (zh) * | 2022-08-25 | 2022-11-22 | 河南本色化工科技有限责任公司 | 一种多环芳烃类化合物的制备方法 |
| CN117865779A (zh) * | 2022-10-10 | 2024-04-12 | 中国石油化工股份有限公司 | 苯酚和环己酮的制备方法 |
| CN121293084A (zh) * | 2024-07-09 | 2026-01-09 | 复旦大学 | 一种基于选择性碳-碳键氧化断裂反应的以烷基芳烃为原料直接制备酚和醛或酮的方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4206082A (en) * | 1976-11-08 | 1980-06-03 | Phillips Petroleum Company | Hydroalkylation process and a composition and process for producing said composition |
| US4463207A (en) * | 1983-09-23 | 1984-07-31 | Shell Oil Company | Arene alkylation with metal oxide-tantalum halide/oxide catalysts |
| GB8809214D0 (en) | 1988-04-19 | 1988-05-25 | Exxon Chemical Patents Inc | Reductive alkylation process |
| US5146024A (en) | 1991-05-20 | 1992-09-08 | Phillips Petroleum Company | Hydroalkylation of aromatic hydrocarbons |
| US6037513A (en) * | 1998-07-09 | 2000-03-14 | Mobil Oil Corporation | Hydroalkylation of aromatic hydrocarbons |
| DE10015880A1 (de) | 2000-03-30 | 2001-10-11 | Creavis Tech & Innovation Gmbh | Verfahren zur Oxidation von Kohlenwasserstoffen |
| DE10015874A1 (de) * | 2000-03-30 | 2001-10-11 | Creavis Tech & Innovation Gmbh | Verfahren zur Herstellung von aromatischen Alkoholen insbesondere Phenol |
| ITMI20022712A1 (it) | 2002-12-20 | 2004-06-21 | Polimeri Europa Spa | Composizione catalitica e processo per la transalchilazione di idrocarburi. |
| US6974788B2 (en) * | 2004-03-12 | 2005-12-13 | Chevron Oronite Company Llc. | Zeolite Y alkylation catalysts |
| JP5534632B2 (ja) * | 2005-09-06 | 2014-07-02 | 宇部興産株式会社 | フェノールおよびシクロアルカノンの製造方法 |
| US7326815B2 (en) | 2005-12-27 | 2008-02-05 | Exxonmobil Chemical Patents Inc. | Selective oxidation of alkylbenzenes |
| ATE523479T1 (de) * | 2007-08-25 | 2011-09-15 | Exxonmobil Chem Patents Inc | Verfahren zur herstellung von cyclohexylbenzen |
| ATE506335T1 (de) | 2007-09-21 | 2011-05-15 | Exxonmobil Chem Patents Inc | Verfahren zur herstellung von cyclohexylbenzol |
| ITMI20080461A1 (it) | 2008-03-18 | 2009-09-19 | Polimeri Europa Spa | Processo per la produzione di idroperossidi di alchilbenzeni in condizioni blande ed in presenza di nuovi sistemi catalitici |
| ITMI20080460A1 (it) | 2008-03-18 | 2009-09-19 | Polimeri Europa Spa | Processo catalitico per la preparazione di idroperossidi di alchilbenzeni mediante ossidazione aerobica in condizioni blande |
-
2009
- 2009-06-29 IT ITMI2009A001145A patent/IT1395594B1/it active
-
2010
- 2010-06-23 US US13/381,466 patent/US8598388B2/en not_active Expired - Fee Related
- 2010-06-23 JP JP2012518136A patent/JP2012532119A/ja active Pending
- 2010-06-23 ES ES10748132T patent/ES2424264T3/es active Active
- 2010-06-23 RU RU2012101712/04A patent/RU2012101712A/ru not_active Application Discontinuation
- 2010-06-23 CN CN2010800361353A patent/CN102548936A/zh active Pending
- 2010-06-23 MX MX2012000175A patent/MX2012000175A/es active IP Right Grant
- 2010-06-23 WO PCT/IB2010/001540 patent/WO2011001244A1/en not_active Ceased
- 2010-06-23 PL PL10748132T patent/PL2448889T3/pl unknown
- 2010-06-23 BR BRPI1011672A patent/BRPI1011672A2/pt not_active IP Right Cessation
- 2010-06-23 EP EP10748132.7A patent/EP2448889B1/en not_active Not-in-force
- 2010-06-29 AR ARP100102310A patent/AR078229A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IT1395594B1 (it) | 2012-10-16 |
| BRPI1011672A2 (pt) | 2017-03-21 |
| EP2448889A1 (en) | 2012-05-09 |
| US8598388B2 (en) | 2013-12-03 |
| WO2011001244A1 (en) | 2011-01-06 |
| ES2424264T3 (es) | 2013-09-30 |
| HK1166492A1 (en) | 2012-11-02 |
| PL2448889T3 (pl) | 2013-10-31 |
| AR078229A1 (es) | 2011-10-26 |
| ITMI20091145A1 (it) | 2010-12-30 |
| US20120157718A1 (en) | 2012-06-21 |
| JP2012532119A (ja) | 2012-12-13 |
| EP2448889B1 (en) | 2013-06-05 |
| CN102548936A (zh) | 2012-07-04 |
| RU2012101712A (ru) | 2013-08-10 |
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| FG | Grant or registration |