JP2015522044A5 - - Google Patents
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- 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
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- 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.)
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- 239000002904 solvent Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000007037 hydroformylation reaction Methods 0.000 description 4
- 238000007792 addition Methods 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
- TVMXDCGIABBOFY-UHFFFAOYSA-N Octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 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
- IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 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-Methyloctanoic acid Chemical compound CCCCC(C)CCC(O)=O LEGGANXCVQPIAI-UHFFFAOYSA-N 0.000 description 1
- GPOPHQSTNHUENT-UHFFFAOYSA-N 6-methyloctanoic acid Chemical compound CCC(C)CCCCC(O)=O GPOPHQSTNHUENT-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
- 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
- XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000004043 oxo group Chemical group O=* 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
- 230000002194 synthesizing Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- DYWSVUBJGFTOQC-UHFFFAOYSA-N ξ-2-Ethylheptanoic acid Chemical compound CCCCCC(CC)C(O)=O DYWSVUBJGFTOQC-UHFFFAOYSA-N 0.000 description 1
Description
脱離水(Spaltwasser)を除去した後に存在するオクテンは、次いで、更に精製することなくまたは有利には蒸留して精製した後に、ヒドロホルミル化反応またはオキソ反応において一酸化炭素及び水との反応に使用される。使用される一酸化炭素と水素との混合物は、合成ガスとも称される。ヒドロホルミル化反応は、均一触媒系中で行われる。均一反応系という用語は、溶媒(添加された場合)、触媒、オレフィン性不飽和化合物及び反応生成物から本質的に組成される均一な溶液を表す。ヒドロホルミル化の際に副生成物として生ずる、製造すべきアルデヒドのより高沸点の縮合化合物、特に製造すべきアルデヒドのトリマー、並びに製造すべきイソノナナールとのこれらの混合物が特に効果的な溶媒として判明しており、そのため、更なる溶媒添加は、必ずしも必要ではない。しかし、溶媒の添加が有利な場合があることが分かっている。溶媒としては、出発材料、反応生成物及び触媒が可溶性の有機化合物が使用される。このような化合物の例は、芳香族炭化水素、例えばベンゼン及びトルエンまたは各異性体のキシレン類及びメシチレン類である。他の慣用の溶媒は、パラフィン油、シクロヘキサン、n−ヘキサン、n−ヘプタンまたはn−オクタン、エーテル類、例えばテトラヒドロフラン、ケトン類またはEastman社のTexanol(登録商標)である。反応媒体中での溶媒の割合は幅広い範囲で変えることができ、通常は、反応混合物を基準にして20〜90重量%の間、好ましくは50〜80重量%の間である。しかし、オクテンのヒドロホルミル化は、溶媒の添加なしでも行うことができる。
反応パートナーの転化は好ましくは大気圧下で行われる。しかし、高められた圧力の使用は排除されない。通常は、1.5MPaまでの大気圧の範囲で、好ましくは0.8MPaまでの大気圧下に作業される。
本発明の方法に従い製造されたイソノナン酸は、主成分である4−メチルオクタン酸、6−メチルオクタン酸、2,5−ジメチルヘプタン酸、2,3−ジメチルヘプタン酸、3−エチルヘプタン酸、2−エチルヘプタン酸及び2−エチル−4−メチルヘキサン酸が、位置異性体の脂肪族C9−モノカルボン酸の総含有量を基準にして、合計で少なくとも80モル%を成すことを特徴とする。
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 (ja) | 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 (ja) |
EP (1) | EP2872466B1 (ja) |
JP (1) | JP6077654B2 (ja) |
KR (1) | KR20150029702A (ja) |
CN (1) | CN104379543B (ja) |
DE (1) | DE102012013969B4 (ja) |
PL (1) | PL2872466T3 (ja) |
TW (1) | TWI487692B (ja) |
WO (1) | WO2014008975A1 (ja) |
Families Citing this family (11)
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 |
CN117185927A (zh) * | 2023-08-01 | 2023-12-08 | 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 |
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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 |
DE102012013968A1 (de) * | 2012-07-13 | 2014-04-03 | Oxea Gmbh | Carbonsäureester der Isononansäure ausgehend von 2-Ethylhexanol, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
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 |
-
2012
- 2012-07-13 DE DE102012013969.1A patent/DE102012013969B4/de not_active Expired - Fee Related
-
2013
- 2013-06-18 WO PCT/EP2013/001798 patent/WO2014008975A1/de active Application Filing
- 2013-06-18 KR KR1020157000763A patent/KR20150029702A/ko not_active Application Discontinuation
- 2013-06-18 US US14/413,503 patent/US9434672B2/en not_active Expired - Fee Related
- 2013-06-18 EP EP13730490.3A patent/EP2872466B1/de not_active Not-in-force
- 2013-06-18 PL PL13730490T patent/PL2872466T3/pl unknown
- 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
- 2013-07-12 TW TW102125012A patent/TWI487692B/zh not_active IP Right Cessation
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