JP2015522044A5 - - Google Patents
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- Publication number
- JP2015522044A5 JP2015522044A5 JP2015520835A JP2015520835A JP2015522044A5 JP 2015522044 A5 JP2015522044 A5 JP 2015522044A5 JP 2015520835 A JP2015520835 A JP 2015520835A JP 2015520835 A JP2015520835 A JP 2015520835A JP 2015522044 A5 JP2015522044 A5 JP 2015522044A5
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- acid
- solvent
- hydroformylation
- produced
- 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
- 239000002904 solvent Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000007037 hydroformylation reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- GPOPHQSTNHUENT-UHFFFAOYSA-N 6-Methyl caprylic acid Chemical compound CCC(C)CCCCC(O)=O GPOPHQSTNHUENT-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- DAFHKNAQFPVRKR-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)C DAFHKNAQFPVRKR-UHFFFAOYSA-N 0.000 description 1
- 239000001706 (4R)-4-methyloctanoic acid Substances 0.000 description 1
- STHOMJJZKIIWLO-UHFFFAOYSA-N 2,3-dimethylheptanoic acid Chemical compound CCCCC(C)C(C)C(O)=O STHOMJJZKIIWLO-UHFFFAOYSA-N 0.000 description 1
- FADNIPWIJRZXGM-UHFFFAOYSA-N 2,5-dimethylheptanoic acid Chemical compound CCC(C)CCC(C)C(O)=O FADNIPWIJRZXGM-UHFFFAOYSA-N 0.000 description 1
- YNEGVNKIKLLHIO-UHFFFAOYSA-N 2-ethyl-4-methylhexanoic acid Chemical compound CCC(C)CC(CC)C(O)=O YNEGVNKIKLLHIO-UHFFFAOYSA-N 0.000 description 1
- MCLMZMISZCYBBG-UHFFFAOYSA-N 3-ethylheptanoic acid Chemical compound CCCCC(CC)CC(O)=O MCLMZMISZCYBBG-UHFFFAOYSA-N 0.000 description 1
- LEGGANXCVQPIAI-UHFFFAOYSA-N 4-methyl-octanoic acid Chemical compound CCCCC(C)CCC(O)=O LEGGANXCVQPIAI-UHFFFAOYSA-N 0.000 description 1
- JRPPVSMCCSLJPL-UHFFFAOYSA-N 7-methyloctanal Chemical compound CC(C)CCCCCC=O JRPPVSMCCSLJPL-UHFFFAOYSA-N 0.000 description 1
- XZOYHFBNQHPJRQ-UHFFFAOYSA-N 7-methyloctanoic acid Chemical compound CC(C)CCCCCC(O)=O XZOYHFBNQHPJRQ-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002732 mesitylenes Chemical class 0.000 description 1
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- DYWSVUBJGFTOQC-UHFFFAOYSA-N xi-2-Ethylheptanoic acid Chemical compound CCCCCC(CC)C(O)=O DYWSVUBJGFTOQC-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102012013969.1A DE102012013969B4 (de) | 2012-07-13 | 2012-07-13 | Verfahren zur Herstellung eines Gemisches stellungsisomerer aliphatischer Isononansäuren ausgehend von 2-Ethylhexanol |
| DE102012013969.1 | 2012-07-13 | ||
| PCT/EP2013/001798 WO2014008975A1 (de) | 2012-07-13 | 2013-06-18 | Verfahren zur herstellung von isononansäuren aus 2-ethylhexanol |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015522044A JP2015522044A (ja) | 2015-08-03 |
| JP2015522044A5 true JP2015522044A5 (enExample) | 2016-07-14 |
| JP6077654B2 JP6077654B2 (ja) | 2017-02-08 |
Family
ID=48670490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015520835A Expired - Fee Related JP6077654B2 (ja) | 2012-07-13 | 2013-06-18 | ２−エチルヘキサノールからイソノナン酸を製造する方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9434672B2 (enExample) |
| EP (1) | EP2872466B1 (enExample) |
| JP (1) | JP6077654B2 (enExample) |
| KR (1) | KR20150029702A (enExample) |
| CN (1) | CN104379543B (enExample) |
| DE (1) | DE102012013969B4 (enExample) |
| PL (1) | PL2872466T3 (enExample) |
| TW (1) | TWI487692B (enExample) |
| WO (1) | WO2014008975A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102012014396B4 (de) * | 2012-07-13 | 2018-01-11 | Oxea Gmbh | Verfahren zur Herstellung eines Vinylestergemisches aus einem Gemisch stellungsisomerer aliphatischer Isononansäuren ausgehend von 2-Ethylhexanol |
| DE102012013968A1 (de) * | 2012-07-13 | 2014-04-03 | Oxea Gmbh | Carbonsäureester der Isononansäure ausgehend von 2-Ethylhexanol, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
| CN105753684B (zh) * | 2016-02-29 | 2018-07-31 | 苏州艾缇克药物化学有限公司 | 一种羟基特戊酸的制备方法 |
| KR101895705B1 (ko) * | 2017-01-25 | 2018-09-07 | 한국과학기술원 | 포지셔닝 로봇 |
| CN108047027B (zh) * | 2017-12-21 | 2021-07-23 | 万华化学集团股份有限公司 | 一种制备异壬酸的系统和方法及金属有机骨架催化剂的制备方法 |
| CN110605145B (zh) * | 2018-06-15 | 2022-04-22 | 万华化学集团股份有限公司 | 一种氢甲酯化反应催化剂及制备异壬酸的方法 |
| US11236031B2 (en) * | 2020-02-12 | 2022-02-01 | Saudi Arabian Oil Company | Integrated process for the production of isononanol and gasoline and diesel blending components |
| CN112657510B (zh) * | 2020-12-31 | 2022-10-25 | 华南理工大学 | 一种催化氧化异壬醇制异壬酸的催化剂及其制备方法与应用 |
| US11542447B2 (en) | 2021-03-09 | 2023-01-03 | Saudi Arabian Oil Company | Integrated process for the production of isononanol and stable / lubricating gasoline and diesel blending components |
| CN114149313B (zh) * | 2022-02-09 | 2022-04-15 | 山东亿科化学有限责任公司 | 一种制备异壬酸的方法 |
| CN116273167B (zh) * | 2023-02-27 | 2025-10-31 | 天津海成能源工程技术有限公司 | 一种异壬醛氧化制备异壬酸的系统及催化剂 |
| JP7441358B1 (ja) * | 2023-04-21 | 2024-02-29 | Ｋｈネオケム株式会社 | ３，５，５－トリメチルヘキサン酸組成物 |
| CN117185927B (zh) * | 2023-08-01 | 2024-07-30 | 广东仁康达材料科技有限公司 | 一种二异丁烯合成异壬酸甲酯的方法 |
Family Cites Families (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB313426A (en) | 1928-03-08 | 1929-06-10 | Ig Farbenindustrie Ag | Improvements in carrying out organic dehydration reactions |
| US2468764A (en) | 1941-05-26 | 1949-05-03 | Laurent Pierre Alfred | Method for dehydrating amyl alcohols |
| DE950007C (de) | 1951-09-26 | 1956-10-04 | Basf Ag | Verfahren zur Herstellung von ª‡-verzweigten gesaettigten Carbonsaeuren |
| US2919973A (en) | 1956-10-18 | 1960-01-05 | William D Stillwell | Method of preparing catalytically active alumina |
| US3527809A (en) | 1967-08-03 | 1970-09-08 | Union Carbide Corp | Hydroformylation process |
| US4148830A (en) | 1975-03-07 | 1979-04-10 | Union Carbide Corporation | Hydroformylation of olefins |
| DE2604545C3 (de) * | 1976-02-06 | 1978-08-17 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von Alkylcarbonsäuren |
| US4247486A (en) | 1977-03-11 | 1981-01-27 | Union Carbide Corporation | Cyclic hydroformylation process |
| DE2844638C2 (de) | 1978-10-13 | 1987-02-26 | Ruhrchemie Ag, 4200 Oberhausen | Verfahren zur Herstellung von Di-n- propylessigsäure |
| US4283562A (en) | 1979-10-26 | 1981-08-11 | Union Carbide Corporation | Hydroformylation process using stable rhodium catalyst |
| DE3048641A1 (de) * | 1980-12-23 | 1982-07-15 | Hoechst Ag, 6000 Frankfurt | "tensidhaltiges gemisch zur reinigung harter oberflaechen" |
| DK0422185T4 (da) | 1989-04-25 | 2008-11-10 | Lubrizol Corp | Carboxylsyreesterholdige væskeblandinger |
| JP2573111B2 (ja) | 1990-09-12 | 1997-01-22 | 花王 株式会社 | 冷凍機作動流体用組成物 |
| JPH055098A (ja) * | 1990-09-12 | 1993-01-14 | Kao Corp | 冷凍機作動流体用組成物 |
| US5210207A (en) * | 1991-01-31 | 1993-05-11 | Union Carbide Chemicals & Plastics Technology Corporation | Transvinylation process by reactive distillation |
| CN1119316C (zh) | 1995-09-25 | 2003-08-27 | 花王株式会社 | 酯化合物作为润滑油基础油的应用 |
| TW455584B (en) | 1998-09-23 | 2001-09-21 | Shell Int Research | Process for the preparation of glycidylesters of branched carboxylic acids |
| DE19906518A1 (de) | 1999-02-17 | 2000-08-31 | Oxeno Olefinchemie Gmbh | Verfahren zur Fraktionierung von Dibuten |
| DE19908320A1 (de) * | 1999-02-26 | 2000-08-31 | Oxeno Olefinchemie Gmbh | Verfahren zur Herstellung von Vinylestern aus Butenoligomeren |
| DE19925385A1 (de) | 1999-06-02 | 2000-12-07 | Oxeno Olefinchemie Gmbh | Verfahren zur katalytischen Durchführung von Mehrphasenreaktionen, insbesondere Vinylierungen von Carbonsäuren |
| DE10010771C1 (de) * | 2000-03-04 | 2001-05-03 | Celanese Chem Europe Gmbh | Verfahren zur Herstellung aliphatischer Carbonsäuren aus Aldehyden |
| EP1199300B1 (en) | 2000-10-16 | 2007-08-22 | Nof Corporation | Production of esters for use as lubricating base stock |
| DE50211172D1 (de) * | 2001-09-26 | 2007-12-20 | Oxeno Olefinchemie Gmbh | Phthalsäurealkylestergemische mit kontrollierter viskosität |
| US6774093B2 (en) | 2002-07-12 | 2004-08-10 | Hatco Corporation | High viscosity synthetic ester lubricant base stock |
| JP4079371B2 (ja) * | 2003-11-13 | 2008-04-23 | 千葉製粉株式会社 | オイルゲル化剤、その製造方法並びにそれを含有するオイルゲル及び化粧料 |
| DE102004055252A1 (de) * | 2004-11-16 | 2006-05-24 | Celanese Chemicals Europe Gmbh | Verfahren zur Herstellung von aliphatischen geradkettigen und ß-alkylverzweigten Carbonsäuren |
| JP5416879B2 (ja) * | 2005-10-14 | 2014-02-12 | Ｊｘ日鉱日石エネルギー株式会社 | 潤滑油組成物 |
| DE102006022168B4 (de) | 2006-05-12 | 2014-02-27 | Oxea Gmbh | Katalytisches Verfahren zur Herstellung von aliphatischen geradkettigen und ß-alkylverzweigten Carbonsäuren |
| CN102014623A (zh) * | 2008-04-29 | 2011-04-13 | 加利福尼亚大学董事会 | 使用聚酮化物合酶制备生物燃料 |
| FR2936249B1 (fr) * | 2008-09-22 | 2012-08-03 | Arkema France | Polyolefine issue de ressources renouvelables et son procede de fabrication |
| DE102009048771A1 (de) | 2009-10-08 | 2011-04-21 | Oxea Deutschland Gmbh | Verfahren zur Herstellung von Polyolestern |
| DE102009048774A1 (de) * | 2009-10-08 | 2011-04-28 | Oxea Deutschland Gmbh | Verfahren zur Farbaufhellung von Polyolestern |
| CA2816640C (en) | 2010-05-04 | 2018-09-25 | Celanese International Corporation | Process for the semi-continuous transvinylation of carboxylic acids with vinyl acetate |
| CN102040501A (zh) * | 2010-10-28 | 2011-05-04 | 中国科学院新疆理化技术研究所 | 水溶性钯膦络合催化剂催化1-辛烯制备壬酸和异壬酸的方法 |
| DE102012014396B4 (de) * | 2012-07-13 | 2018-01-11 | Oxea Gmbh | Verfahren zur Herstellung eines Vinylestergemisches aus einem Gemisch stellungsisomerer aliphatischer Isononansäuren ausgehend von 2-Ethylhexanol |
| DE102012013968A1 (de) * | 2012-07-13 | 2014-04-03 | Oxea Gmbh | Carbonsäureester der Isononansäure ausgehend von 2-Ethylhexanol, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
-
2012
- 2012-07-13 DE DE102012013969.1A patent/DE102012013969B4/de not_active Expired - Fee Related
-
2013
- 2013-06-18 KR KR1020157000763A patent/KR20150029702A/ko not_active Withdrawn
- 2013-06-18 CN CN201380032680.9A patent/CN104379543B/zh not_active Expired - Fee Related
- 2013-06-18 JP JP2015520835A patent/JP6077654B2/ja not_active Expired - Fee Related
- 2013-06-18 US US14/413,503 patent/US9434672B2/en not_active Expired - Fee Related
- 2013-06-18 WO PCT/EP2013/001798 patent/WO2014008975A1/de not_active Ceased
- 2013-06-18 EP EP13730490.3A patent/EP2872466B1/de not_active Not-in-force
- 2013-06-18 PL PL13730490T patent/PL2872466T3/pl unknown
- 2013-07-12 TW TW102125012A patent/TWI487692B/zh not_active IP Right Cessation
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