JP2009538934A5 - - Google Patents
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- Publication number
- JP2009538934A5 JP2009538934A5 JP2009513461A JP2009513461A JP2009538934A5 JP 2009538934 A5 JP2009538934 A5 JP 2009538934A5 JP 2009513461 A JP2009513461 A JP 2009513461A JP 2009513461 A JP2009513461 A JP 2009513461A JP 2009538934 A5 JP2009538934 A5 JP 2009538934A5
- Authority
- JP
- Japan
- Prior art keywords
- component
- aromatic compound
- hydroxyl
- alkylated aromatic
- halides
- 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.)
- Granted
Links
- 150000001491 aromatic compounds Chemical class 0.000 claims 29
- 238000000034 method Methods 0.000 claims 25
- -1 aluminum halide Chemical class 0.000 claims 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 12
- 239000011831 acidic ionic liquid Substances 0.000 claims 11
- 239000003054 catalyst Substances 0.000 claims 11
- 150000001336 alkenes Chemical class 0.000 claims 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- 239000007848 Bronsted acid Substances 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- 238000005804 alkylation reaction Methods 0.000 claims 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 5
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 229910052782 aluminium Inorganic materials 0.000 claims 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical group Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims 4
- SZYJELPVAFJOGJ-UHFFFAOYSA-N trimethylamine hydrochloride Chemical compound Cl.CN(C)C SZYJELPVAFJOGJ-UHFFFAOYSA-N 0.000 claims 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 229910052733 gallium Inorganic materials 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 150000005673 monoalkenes Chemical class 0.000 claims 3
- 239000000178 monomer Substances 0.000 claims 3
- 238000006384 oligomerization reaction Methods 0.000 claims 3
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- BMQZYMYBQZGEEY-UHFFFAOYSA-M 1-ethyl-3-methylimidazolium chloride Chemical compound [Cl-].CCN1C=C[N+](C)=C1 BMQZYMYBQZGEEY-UHFFFAOYSA-M 0.000 claims 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 2
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 claims 2
- 239000005711 Benzoic acid Substances 0.000 claims 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 2
- 239000005703 Trimethylamine hydrochloride Substances 0.000 claims 2
- 235000010233 benzoic acid Nutrition 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 230000003606 oligomerizing effect Effects 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical class C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000010924 continuous production Methods 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims 1
- 150000004714 phosphonium salts Chemical class 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/445,561 | 2006-06-01 | ||
| US11/445,561 US7732651B2 (en) | 2006-06-01 | 2006-06-01 | Method of making an alkylated aromoatic using acidic ionic liquid catalyst |
| PCT/US2007/070133 WO2007143513A2 (en) | 2006-06-01 | 2007-05-31 | A method of making an alkylated aromatic using compound using an acidic ionic liquid catalyst |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013191266A Division JP2014012722A (ja) | 2006-06-01 | 2013-09-17 | 酸性イオン液体触媒を用いるアルキル化芳香族化合物の製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009538934A JP2009538934A (ja) | 2009-11-12 |
| JP2009538934A5 true JP2009538934A5 (enExample) | 2010-07-15 |
| JP5748406B2 JP5748406B2 (ja) | 2015-07-15 |
Family
ID=38791148
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009513461A Expired - Fee Related JP5748406B2 (ja) | 2006-06-01 | 2007-05-31 | 酸性イオン液体触媒を用いるアルキル化芳香族化合物の製造方法 |
| JP2013191266A Withdrawn JP2014012722A (ja) | 2006-06-01 | 2013-09-17 | 酸性イオン液体触媒を用いるアルキル化芳香族化合物の製造方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013191266A Withdrawn JP2014012722A (ja) | 2006-06-01 | 2013-09-17 | 酸性イオン液体触媒を用いるアルキル化芳香族化合物の製造方法 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US7732651B2 (enExample) |
| EP (1) | EP2021307A4 (enExample) |
| JP (2) | JP5748406B2 (enExample) |
| CN (1) | CN101484407A (enExample) |
| AR (1) | AR061172A1 (enExample) |
| BR (1) | BRPI0712562A2 (enExample) |
| CA (1) | CA2653960C (enExample) |
| MY (1) | MY148281A (enExample) |
| SG (1) | SG188013A1 (enExample) |
| WO (1) | WO2007143513A2 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7732651B2 (en) * | 2006-06-01 | 2010-06-08 | Chevron Oronite Company, Llc | Method of making an alkylated aromoatic using acidic ionic liquid catalyst |
| US20080008853A1 (en) * | 2006-07-05 | 2008-01-10 | The Procter & Gamble Company | Web comprising a tuft |
| US8329966B2 (en) * | 2006-10-25 | 2012-12-11 | Formosan Union Chemical Corp. | Slightly branched dialkyl benzenes and related compositions |
| WO2009067417A1 (en) * | 2007-11-20 | 2009-05-28 | Siemens Heathcare Diagnostics Inc. | Facile n-alkylation of acridine compounds in ionic liquids |
| US8486877B2 (en) * | 2009-11-18 | 2013-07-16 | Chevron Oronite Company Llc | Alkylated hydroxyaromatic compound substantially free of endocrine disruptive chemicals |
| US8888993B2 (en) | 2010-07-30 | 2014-11-18 | Chevron U.S.A. Inc. | Treatment of a hydrocarbon feed |
| WO2013061336A2 (en) * | 2011-08-23 | 2013-05-02 | Reliance Industries Ltd | A process for producing alkylated aromatic hydrocarbons |
| CN102603451A (zh) * | 2012-02-28 | 2012-07-25 | 南开大学 | 一种浓硫酸和离子液体混合液催化制备二芳基乙烷的方法 |
| US9233316B2 (en) | 2012-07-31 | 2016-01-12 | Chevron U.S.A. Inc. | Hydrogen recycle and hydrogen chloride recovery in an alkylation process |
| US9302199B2 (en) | 2012-07-31 | 2016-04-05 | Chevron U.S.A. Inc. | Alkylation process with recycle of hydrogen and recovery of hydrogen chloride |
| US8704018B2 (en) | 2012-07-31 | 2014-04-22 | Chevron U.S.A. Inc. | Extracted conjunct polymer naphtha |
| BR102013032982A2 (pt) * | 2013-12-20 | 2015-09-08 | Whirlpool Sa | óleo, composição lubrificante com lubricidade melhorada e coeficiente de desempenho aumentado, usos e máquina de refrigeração |
| CN111234862A (zh) * | 2014-02-07 | 2020-06-05 | 沙特基础工业公司 | 使用酸催化剂如酸性离子液体从烯烃流中去除芳香族杂质 |
| WO2015118469A1 (en) | 2014-02-07 | 2015-08-13 | Saudi Basic Industries Corporation | Removal of aromatic impurities from an alkene stream using an acid catalyst |
| US20160067668A1 (en) * | 2014-09-09 | 2016-03-10 | Chevron U.S.A. Inc. | Cost-effective materials for process units using acidic ionic liquids |
| KR102329122B1 (ko) * | 2014-10-23 | 2021-11-19 | 에스케이이노베이션 주식회사 | Ｃ4, ｃ5, ｃ6 스트림을 이용한 탄화수소의 업그레이드 방법 |
| US10023508B2 (en) | 2014-12-12 | 2018-07-17 | Uop Llc | Viscosity modifiers for decreasing the viscosity of ionic liquids |
| WO2016202905A1 (en) | 2015-06-18 | 2016-12-22 | Shell Internationale Research Maatschappij B.V. | Process for monitoring the catalytic activity of an ionic liquid |
| CN105712911A (zh) * | 2016-01-22 | 2016-06-29 | 江苏丰山集团股份有限公司 | 一种2-硝基-4-甲砜基甲苯的制备方法 |
| JP6733036B2 (ja) * | 2016-07-29 | 2020-07-29 | ザ プロクター アンド ギャンブル カンパニーＴｈｅ Ｐｒｏｃｔｅｒ ＆ Ｇａｍｂｌｅ Ｃｏｍｐａｎｙ | 乳酸又はその誘導体からアクリル酸を製造するための液相の触媒 |
| CN107983409B (zh) * | 2016-10-26 | 2020-10-27 | 中国石油化工股份有限公司 | 低分子烯烃聚合物的制备方法 |
| CA3075165A1 (en) * | 2017-09-22 | 2019-03-28 | Indorama Ventures Oxides Llc | A process for the production of alkylaromatics |
| TWI665185B (zh) * | 2018-11-13 | 2019-07-11 | 台灣中油股份有限公司 | 一種使用環氧脂肪酸烷基酯類製備生質多元醇之方法 |
| CN109894152B (zh) * | 2019-03-20 | 2021-11-05 | 曲阜师范大学 | 一种用于合成四氢呋喃的催化剂制备方法及其所得催化剂和应用 |
| WO2021245491A1 (en) * | 2020-06-03 | 2021-12-09 | Chevron U.S.A. Inc. | Synthesis of szr framework type molecular sieves |
| CN114349890B (zh) * | 2022-01-28 | 2024-03-08 | 长兴（广州）光电材料有限公司 | 一种超高交联树脂及其制备方法与应用 |
Family Cites Families (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1595394C3 (de) * | 1965-03-16 | 1973-10-04 | Cosden Oil & Chemical Co., Big Spring, Tex. (V.St.A.) | Flüssige Mischung auf der Basis hochmolekularer isoalkylierter aromatischer Kohlenwasserstoffe mit einem mittleren Molekulargewicht über 250 |
| FR2081989A5 (enExample) * | 1969-11-24 | 1971-12-10 | Inst Francais Du Petrole | |
| US4024203A (en) * | 1969-11-24 | 1977-05-17 | Institut Francais Du Petrole | Oligomerization of unsaturated hydrocarbons with acid catalysts |
| US3732324A (en) * | 1971-04-02 | 1973-05-08 | Continental Oil Co | Process for producing oil-soluble sulfonate feedstock |
| GB1449840A (en) * | 1973-10-08 | 1976-09-15 | British Petroleum Co | Alkylation process |
| US4049737A (en) * | 1975-09-18 | 1977-09-20 | Mobil Oil Corporation | Propylation of toluene |
| US4469908A (en) * | 1978-12-14 | 1984-09-04 | Mobil Oil Corporation | Alkylation of aromatic hydrocarbons |
| US4503277A (en) | 1983-11-30 | 1985-03-05 | Uop Inc. | HF regeneration in aromatic hydrocarbon alkylation process |
| US4670617A (en) * | 1985-12-30 | 1987-06-02 | Amoco Corporation | Propylation of toluene with a high surface area, zinc-modified, crystalline silica molecular sieve |
| US5026933A (en) * | 1987-10-07 | 1991-06-25 | Mobil Oil Corporation | Olefin oligomerization with surface modified zeolite catalyst |
| US4912277A (en) * | 1989-05-30 | 1990-03-27 | Mobil Oil Corporation | Process for preparing long chain alkyl aromatic compounds |
| US5132477A (en) * | 1991-04-29 | 1992-07-21 | Mobil Oil Corporation | Process for producing alkylaromatic lubricant fluids |
| US5288677A (en) * | 1991-06-28 | 1994-02-22 | Exxon Chemical Patents Inc. | Immobilized Lewis acid catalysts |
| DE69302117T2 (de) | 1992-02-19 | 1996-08-29 | Bp Chem Int Ltd | Butenpolymere |
| DE69423165T2 (de) | 1993-09-22 | 2000-07-06 | Institut Francais Du Petrole, Rueil-Malmaison | Nickel enthaltende Katalysatorzusammensetzung und Verfahren zum Dimerisieren und Oligomerisieren von Olefinen |
| BR9505775A (pt) | 1994-02-10 | 1996-02-27 | Bp Chem Int Ltd | Liquido iônico processo para produçao de liquido iônicos e processo para conversao de hidrocarbonetos olefinicos |
| GB9402612D0 (en) | 1994-02-10 | 1994-04-06 | British Petroleum Co Plc | Ionic liquids |
| GB9402569D0 (en) * | 1994-02-10 | 1994-04-06 | Bp Chem Int Ltd | Alkylation process |
| JPH08119880A (ja) * | 1994-09-27 | 1996-05-14 | Mitsubishi Oil Co Ltd | １，２，４，５，−ジメチルジイソプロピルベンゼンの製造方法 |
| GB9425105D0 (en) | 1994-12-13 | 1995-02-08 | Bp Chem Int Ltd | Ionic liquids |
| GB9603754D0 (en) | 1996-02-22 | 1996-04-24 | Bp Chem Int Ltd | Lubricating oils |
| US5824832A (en) * | 1996-07-22 | 1998-10-20 | Akzo Nobel Nv | Linear alxylbenzene formation using low temperature ionic liquid |
| US5731101A (en) | 1996-07-22 | 1998-03-24 | Akzo Nobel Nv | Low temperature ionic liquids |
| WO1998050153A1 (en) | 1997-05-01 | 1998-11-12 | Akzo Nobel N.V. | In-situ formation of ionic liquid catalyst for an ionic liquid-catalyzed chemical reaction |
| IT1299035B1 (it) * | 1998-04-07 | 2000-02-07 | Enichem Spa | Processo per la preparazione di composti aromatici monoalchilati |
| US6071864A (en) * | 1998-07-17 | 2000-06-06 | Mobil Oil Corporation | Methods for preparation of arylated poly∝olefins |
| US20020010291A1 (en) | 1998-12-04 | 2002-01-24 | Vince Murphy | Ionic liquids and processes for production of high molecular weight polyisoolefins |
| US7259284B2 (en) * | 2000-05-31 | 2007-08-21 | Chevron Phillips Chemical Company, Lp | Method for manufacturing high viscosity polyalphaolefins using ionic liquid catalysts |
| US20020128532A1 (en) * | 2000-05-31 | 2002-09-12 | Chevron Chemical Company Llc | High viscosity polyalphaolefins prepared with ionic liquid catalyst |
| US6936744B1 (en) * | 2000-07-19 | 2005-08-30 | Exxonmobil Chemical Patents, Inc. | Alkylaromatics production |
| NL1021362C2 (nl) * | 2001-08-31 | 2003-08-05 | Inst Francais Du Petrole | Katalysator- en oplosmiddelsamenstelling en katalysewerkwijzen waarbij deze samenstelling wordt toegepast. |
| US7332460B2 (en) * | 2004-07-15 | 2008-02-19 | Chevron Oronite Company Llc | Alkylxylene sulfonates for enhanced oil recovery processes |
| US7449596B2 (en) * | 2005-12-21 | 2008-11-11 | Chevron Oronite Company Llc | Method of making a synthetic petroleum sulfonate |
| US8524965B2 (en) * | 2005-12-21 | 2013-09-03 | Chevron Oronite Company Llc | Method of making an alkylated aromatic using acidic ionic liquid catalyst |
| US7732651B2 (en) * | 2006-06-01 | 2010-06-08 | Chevron Oronite Company, Llc | Method of making an alkylated aromoatic using acidic ionic liquid catalyst |
| US7495140B2 (en) * | 2006-06-01 | 2009-02-24 | Chevron Cronite Company Llc | Method of making a synthetic alkylaryl compound |
-
2006
- 2006-06-01 US US11/445,561 patent/US7732651B2/en not_active Expired - Fee Related
-
2007
- 2007-05-31 EP EP07811989A patent/EP2021307A4/en not_active Ceased
- 2007-05-31 MY MYPI20084881A patent/MY148281A/en unknown
- 2007-05-31 SG SG2011062932A patent/SG188013A1/en unknown
- 2007-05-31 BR BRPI0712562-3A patent/BRPI0712562A2/pt not_active Application Discontinuation
- 2007-05-31 WO PCT/US2007/070133 patent/WO2007143513A2/en not_active Ceased
- 2007-05-31 JP JP2009513461A patent/JP5748406B2/ja not_active Expired - Fee Related
- 2007-05-31 CN CNA2007800248556A patent/CN101484407A/zh active Pending
- 2007-05-31 CA CA2653960A patent/CA2653960C/en not_active Expired - Fee Related
- 2007-06-01 AR ARP070102390A patent/AR061172A1/es unknown
-
2010
- 2010-02-19 US US12/660,083 patent/US20100160703A1/en not_active Abandoned
-
2013
- 2013-09-17 JP JP2013191266A patent/JP2014012722A/ja not_active Withdrawn
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