JP2013512925A5 - - Google Patents
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- Publication number
- JP2013512925A5 JP2013512925A5 JP2012542218A JP2012542218A JP2013512925A5 JP 2013512925 A5 JP2013512925 A5 JP 2013512925A5 JP 2012542218 A JP2012542218 A JP 2012542218A JP 2012542218 A JP2012542218 A JP 2012542218A JP 2013512925 A5 JP2013512925 A5 JP 2013512925A5
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- raffinate
- isobutylene
- temperature
- amount
- 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
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 18
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 15
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- 239000012043 crude product Substances 0.000 description 10
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 9
- 239000001282 iso-butane Substances 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26682809P | 2009-12-04 | 2009-12-04 | |
| US61/266,828 | 2009-12-04 | ||
| PCT/US2010/058866 WO2011069052A2 (en) | 2009-12-04 | 2010-12-03 | Process for producing a t-butyl phenol from a c4 raffinate stream |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015179301A Division JP2015221838A (ja) | 2009-12-04 | 2015-09-11 | Ｃ４ラフィネートストリームからｔ−ブチルフェノールを生産する方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013512925A JP2013512925A (ja) | 2013-04-18 |
| JP2013512925A5 true JP2013512925A5 (enExample) | 2015-02-19 |
| JP5851415B2 JP5851415B2 (ja) | 2016-02-03 |
Family
ID=43607992
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012542218A Expired - Fee Related JP5851415B2 (ja) | 2009-12-04 | 2010-12-03 | Ｃ４ラフィネートストリームからｔ−ブチルフェノールを生産する方法 |
| JP2015179301A Pending JP2015221838A (ja) | 2009-12-04 | 2015-09-11 | Ｃ４ラフィネートストリームからｔ−ブチルフェノールを生産する方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015179301A Pending JP2015221838A (ja) | 2009-12-04 | 2015-09-11 | Ｃ４ラフィネートストリームからｔ−ブチルフェノールを生産する方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8937201B2 (enExample) |
| EP (2) | EP2521706A2 (enExample) |
| JP (2) | JP5851415B2 (enExample) |
| KR (1) | KR101822607B1 (enExample) |
| CN (1) | CN102906059B (enExample) |
| BR (1) | BR112012013419C8 (enExample) |
| ES (1) | ES2647102T3 (enExample) |
| PL (1) | PL2657217T3 (enExample) |
| PT (1) | PT2657217T (enExample) |
| RU (1) | RU2606130C2 (enExample) |
| SA (1) | SA110310888B1 (enExample) |
| SG (1) | SG181078A1 (enExample) |
| TW (2) | TWI570102B (enExample) |
| WO (1) | WO2011069052A2 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106133018B (zh) | 2013-10-17 | 2020-07-14 | Si集团有限公司 | 原位烷基苯酚-醛树脂 |
| CN105705541B (zh) | 2013-10-17 | 2018-08-24 | Si集团有限公司 | 通过水杨酸稳定的改性烷基苯酚-醛树脂 |
| WO2015094571A1 (en) * | 2013-12-20 | 2015-06-25 | Exxonmobil Chemical Patents Inc. | Phenol composition |
| US9434668B1 (en) | 2015-04-09 | 2016-09-06 | Council Of Scientific And Industrial Research | Process for the production of tertiary butyl phenols |
| CN108026010A (zh) * | 2015-09-11 | 2018-05-11 | 巴斯夫欧洲公司 | 用于酚的烷基化的方法 |
| CN106975517A (zh) * | 2017-05-16 | 2017-07-25 | 同济大学 | 一种绿色高效合成2,4‑二叔丁基苯酚的多相催化剂 |
| CN113636916B (zh) * | 2021-09-17 | 2023-08-29 | 陕西万汇能聚科技有限公司 | 一种合成2,4,6-三叔丁基苯酚的方法 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2353282A (en) | 1941-10-15 | 1944-07-11 | Bakelite Corp | Preparation of substituted phenols |
| US2430190A (en) * | 1943-08-30 | 1947-11-04 | Universal Oil Prod Co | Alkylation of phenols |
| GB655124A (en) * | 1948-06-16 | 1951-07-11 | Standard Oil Dev Co | Improvements in or relating to the preparation of poly-tert-butyl phenol or cresols |
| US3670030A (en) * | 1970-02-20 | 1972-06-13 | Universal Oil Prod Co | Alkylation of phenolic compound |
| US3751509A (en) * | 1972-07-17 | 1973-08-07 | A Liakumovich | Process for isolating isobutylene from butane-butylene fraction |
| SU783297A1 (ru) * | 1976-08-11 | 1980-11-30 | Стерлитамакский опытно-промышленный нефтехимический завод | Способ получени 2,6-ди-третбутилфенола |
| US4166191A (en) | 1976-09-20 | 1979-08-28 | Hitachi Chemical Company, Ltd. | Process for producing highly pure p-tertiary-butyl phenol |
| DE2745589C3 (de) * | 1977-10-11 | 1980-03-27 | Chemische Werke Huels Ag, 4370 Marl | Verfahren zur Herstellung von p-Alkylphenolen |
| JPS6052688B2 (ja) * | 1977-11-18 | 1985-11-20 | 三井化学株式会社 | フエノ−ルのアルキル化方法 |
| US4260833A (en) | 1979-11-30 | 1981-04-07 | Uop Inc. | Preparation of alkylphenols |
| JPS6052732B2 (ja) * | 1980-12-05 | 1985-11-21 | 三井化学株式会社 | ２，６−ジ−ｔ−ブチルフエノ−ルの製造方法 |
| JPS5852234A (ja) * | 1981-09-21 | 1983-03-28 | Yotsukaichi Gosei Kk | パラタ−シヤリプチルフエノ−ルの製造法 |
| JPS61200934A (ja) * | 1985-03-02 | 1986-09-05 | Maruzen Sekiyu Kagaku Kk | ｔｅｒｔ―ブチルフエノール類の製造方法 |
| US4631349A (en) * | 1985-06-25 | 1986-12-23 | Ethyl Corporation | Heterogeneous catalyst process |
| JPH07108870B2 (ja) * | 1986-12-23 | 1995-11-22 | 三井石油化学工業株式会社 | ２，４−ジ−ｔ−ブチルフエノ−ルの製造方法 |
| US4731492A (en) * | 1987-03-04 | 1988-03-15 | Ethyl Corporation | Phenol alkylation process |
| DE3941472C1 (enExample) * | 1989-12-15 | 1991-02-21 | Huels Ag, 4370 Marl, De | |
| CS276820B6 (cs) * | 1990-05-28 | 1992-08-12 | Slovenska Technicke Univerzita | Sposob alkylácie a/alebo arylalkylácie fenolu a/alebo jeho derivátov |
| DE4139056A1 (de) * | 1991-11-28 | 1993-06-03 | Huels Chemische Werke Ag | Verfahren zur herstellung von ortho-substituierten alkylphenolen und katalysator hierfuer |
| JPH05294865A (ja) * | 1992-04-15 | 1993-11-09 | Dainippon Ink & Chem Inc | ２，４−ジ（ｔ−ブチル）フェノールの製法 |
| BR9202890A (pt) | 1992-07-22 | 1994-02-01 | Rhodia | Aperfeicoamento em processo para obtencao de terciobutilfenois |
| ATE231117T1 (de) * | 1998-09-03 | 2003-02-15 | Gen Electric | Verfahren zur reinigung von alkylierten phenolen durch schmelzkristallisierung |
| RU2164509C1 (ru) * | 1999-08-06 | 2001-03-27 | ООО "Синтезхим Бис" | Способ получения 2,6-ди-трет-бутил-фенола |
| JP2002241334A (ja) * | 2001-02-15 | 2002-08-28 | Sumitomo Chem Co Ltd | ｔｅｒｔ−ブチルフェノール類の製造方法 |
| CN1844071A (zh) * | 2006-03-24 | 2006-10-11 | 北京极易化工有限公司 | 一种高转化率高选择性的苯酚邻位烷基化方法 |
| CN1935763A (zh) * | 2006-10-20 | 2007-03-28 | 上海金海雅宝精细化工有限公司 | 一种2.4－二叔丁基苯酚烷化液的制备方法 |
| CN101092331A (zh) * | 2007-07-06 | 2007-12-26 | 宁波金海雅宝化工有限公司 | 一种固定床合成烷基酚的方法 |
-
2010
- 2010-11-29 TW TW099141217A patent/TWI570102B/zh not_active IP Right Cessation
- 2010-11-29 TW TW105131059A patent/TWI624450B/zh not_active IP Right Cessation
- 2010-12-01 SA SA110310888A patent/SA110310888B1/ar unknown
- 2010-12-03 RU RU2012127805A patent/RU2606130C2/ru active
- 2010-12-03 EP EP10788470A patent/EP2521706A2/en not_active Withdrawn
- 2010-12-03 US US13/513,666 patent/US8937201B2/en not_active Expired - Fee Related
- 2010-12-03 SG SG2012038782A patent/SG181078A1/en unknown
- 2010-12-03 PL PL13168390T patent/PL2657217T3/pl unknown
- 2010-12-03 CN CN201080054733.3A patent/CN102906059B/zh not_active Expired - Fee Related
- 2010-12-03 ES ES13168390.6T patent/ES2647102T3/es active Active
- 2010-12-03 KR KR1020127014496A patent/KR101822607B1/ko not_active Expired - Fee Related
- 2010-12-03 JP JP2012542218A patent/JP5851415B2/ja not_active Expired - Fee Related
- 2010-12-03 EP EP13168390.6A patent/EP2657217B1/en not_active Not-in-force
- 2010-12-03 BR BR112012013419A patent/BR112012013419C8/pt not_active IP Right Cessation
- 2010-12-03 PT PT131683906T patent/PT2657217T/pt unknown
- 2010-12-03 WO PCT/US2010/058866 patent/WO2011069052A2/en not_active Ceased
-
2015
- 2015-09-11 JP JP2015179301A patent/JP2015221838A/ja active Pending
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