CN116265481A - 铂-联苯-碘配合物和铂-联苯-溴配合物 - Google Patents
铂-联苯-碘配合物和铂-联苯-溴配合物 Download PDFInfo
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- CN116265481A CN116265481A CN202211612404.7A CN202211612404A CN116265481A CN 116265481 A CN116265481 A CN 116265481A CN 202211612404 A CN202211612404 A CN 202211612404A CN 116265481 A CN116265481 A CN 116265481A
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- biphenyl
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- 229910052740 iodine Inorganic materials 0.000 title claims description 8
- 239000011630 iodine Substances 0.000 title claims description 8
- -1 platinum-biphenyl-bromine Chemical compound 0.000 title abstract description 18
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract description 6
- 239000003446 ligand Substances 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
- RRTJOAHJZQVSSE-UHFFFAOYSA-N 1,3,2-dioxaphosphepine Chemical compound C=1C=COPOC=1 RRTJOAHJZQVSSE-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 125000003336 coronenyl group Chemical group C1(=CC2=CC=C3C=CC4=CC=C5C=CC6=CC=C1C1=C6C5=C4C3=C21)* 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
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- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
- B01J31/185—Phosphites ((RO)3P), their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof
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Abstract
本发明涉及铂‑联苯‑碘配合物和铂‑联苯‑溴配合物，及其用于催化加氢甲酰化反应的用途。
Description
技术领域
本发明涉及铂-联苯-碘配合物和铂-联苯-溴配合物，及其用于催化加氢甲酰化反应的用途。
背景技术
EP 2663573 B1了描述制备(1)的方法
6,6'-[(3,3'-二-叔丁基-5,5'-二甲氧基-1,1'-联苯基-2,2'-二基)二(氧)二(二苯并[d,f][1,3,2]二氧杂磷杂环庚二烯)(BiPhePhos))。
发明内容
本发明所基于的目的是提供一种新的配合物。在催化加氢甲酰化反应的情况下，该配合物应提供增加的产率。
该目的通过根据权利要求1所述的配合物实现。
配合物，其包含：
a) Pt；
b) 符合式(I)的配体：
其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12选自：-H、-(C1-C12)-烷基、-O-(C1-C12)-烷基、-(C6-C20)-芳基；
c) 碘配体或溴配体。
术语(C1-C12)-烷基包括具有1至12个碳原子的直链和支链烷基。这些优选是(C1-C8)-烷基，更优选(C1-C6)-烷基，最优选(C1-C4)-烷基。
合适的(C1-C12)-烷基特别是甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、2-戊基、2-甲基丁基、3-甲基丁基、1,2-二甲基丙基、1,1-二甲基丙基、2,2-二甲基丙基、1-乙基丙基、正己基、2-己基、2-甲基戊基、3-甲基戊基、4-甲基戊基，1,1-二甲基丁基、1,2-二甲基丁基、2,2-二甲基丁基、1,3-二甲基丁基，2,3-二甲基丁基、3,3-二甲基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基丁基、1-乙基-2-甲基丙基，正庚基、2-庚基，3-庚基、2-乙基戊基、1-丙基丁基、正辛基、2-乙基己基、2-丙基庚基、壬基、癸基。
(C1-C12)-烷基的定义也类似地适用于-O-(C1-C12)-烷基中的(C1-C12)-烷基。
术语(C6-C20)-芳基包括具有6至20个碳原子的单环或多环芳族烃基。这些优选是(C6-C14)-芳基，更优选(C6-C10)-芳基。
合适的(C6-C20)-芳基特别是苯基、萘基、茚基、芴基、蒽基、菲基、并四苯基、䓛基、芘基、蒄基。优选的(C6-C20)-芳基是苯基、萘基和蒽基。
在一个实施方案中，R1、R2、R3、R4选自：-(C1-C12)-烷基、-O-(C1-C12)-烷基。
在一个实施方案中，R1和R4是-(C1-C12)-烷基。
在一个实施方案中，R1和R4是-tBu。
在一个实施方案中，R2和R3是-O-(C1-C12)-烷基。
在一个实施方案中，R2和R3是-OMe。
在一个实施方案中，R5、R6、R7、R8、R9、R10、R11、R12是-H。
在一个实施方案中，根据式(I)的化合物具有结构(1)：
在一个实施方案中，该配合物具有正好一个对应于式(I)的配体。
在一个实施方案中，该配合物具有至少两个碘配体。
在一个实施方案中，该配合物具有正好两个碘配体。
在一个实施方案中，该配合物具有至少两个溴配体。
在一个实施方案中，该配合物具有正好两个溴配体。
除了配合物本身，还要求保护其用于催化加氢甲酰化反应的用途。
上述配合物用于催化加氢甲酰化反应的用途。
具体实施方式
本发明将在下文中通过工作实施例进行详细说明。
实验描述
向小瓶中装入PtX2（X=卤素）、配体和烘箱干燥的搅拌棒。然后用隔膜（PTFE涂覆的丁苯橡胶）和酚醛树脂盖密封小瓶。将小瓶抽真空并重新填充氩气三次。使用注射器将甲苯和1-辛烯添加到小瓶中。将小瓶置于合金板（Legierungsplatte）中，在氩气气氛下将其转移至Parr Instruments的4560系列高压釜中。用CO/H2吹扫高压釜三次后，在室温下将合成气压力增加至40巴。反应在120℃下进行20 h。反应结束后，将高压釜冷却至室温并小心减压。通过GC分析确定产率和选择性。
卤素的变化
反应条件：
1.0 mmol的1-辛烯，1.0 mol% PtX2，2.2当量的配体(1)，溶剂：甲苯，p(CO/H2)：40巴，T：120℃，t：20 h。
产率：
| 配体 | 卤素 | 产率[%] |
 |
I / Br | 69 / 27 |
如实验结果所示，该目的通过根据本发明的配合物得以实现。
Claims (12)
1.配合物，其包含：
a) Pt；
b) 符合式(I)的配体：
其中R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12选自：-H、-(C1-C12)-烷基、-O-(C1-C12)-烷基、-(C6-C20)-芳基；
c) 碘配体或溴配体。
2.根据权利要求1所述的配合物，
其中R1、R2、R3、R4选自：-(C1-C12)-烷基、-O-(C1-C12)-烷基。
3.根据权利要求1或2任一项所述的配合物，
其中R1和R4是-(C1-C12)-烷基。
4.根据权利要求1至3中任一项所述的配合物，
其中R2和R3是-O-(C1-C12)-烷基。
5.根据权利要求1至4中任一项所述的配合物，
其中R5、R6、R7、R8、R9、R10、R11、R12是-H。
6.根据权利要求1至5中任一项所述的配合物，
其中根据式(I)的化合物具有结构(1)：
7.根据权利要求1至6中任一项所述的配合物，
其中所述配合物具有正好一个符合式(I)的配体。
8.根据权利要求1至7中任一项所述的配合物，
其中所述配合物具有至少两个碘配体。
9.根据权利要求8所述的配合物，
其中所述配合物具有正好两个碘配体。
10.根据权利要求1至7中任一项所述的配合物，
其中所述配合物具有至少两个溴配体。
11.根据权利要求10所述的配合物，
其中所述配合物具有正好两个溴配体。
12.根据权利要求1至11中任一项所述的配合物用于催化加氢甲酰化反应的用途。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP21215366.2A EP4198001B1 (de) | 2021-12-17 | 2021-12-17 | Pt-biphenyl-iod-komplex und pt-biphenyl-brom-komplex |
| EP21215366.2 | 2021-12-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116265481A true CN116265481A (zh) | 2023-06-20 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202211612404.7A Pending CN116265481A (zh) | 2021-12-17 | 2022-12-15 | 铂-联苯-碘配合物和铂-联苯-溴配合物 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US12030899B2 (zh) |
| EP (1) | EP4198001B1 (zh) |
| JP (1) | JP2023090660A (zh) |
| KR (1) | KR20230092781A (zh) |
| CN (1) | CN116265481A (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP4197995A1 (de) | 2021-12-17 | 2023-06-21 | Evonik Operations GmbH | Pt-xanthen-iod-komplex und pt-xanthen-brom-komplex |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1368434A (en) * | 1971-11-18 | 1974-09-25 | Ici Ltd | Hydroformylation of propylene |
| US4668651A (en) * | 1985-09-05 | 1987-05-26 | Union Carbide Corporation | Transition metal complex catalyzed processes |
| DE4204808A1 (de) * | 1992-02-18 | 1993-08-19 | Basf Ag | Verfahren zur herstellung von (omega)-formylalkancarbonsaeureestern |
| JP3812095B2 (ja) * | 1997-10-28 | 2006-08-23 | 三菱化学株式会社 | アルデヒド類の製造方法及びこれに用いるビスホスファイト |
| US5962744A (en) | 1998-03-27 | 1999-10-05 | The Research Foundation Of State University Of New York | Process for hydrocarbonylations in supercritical carbon dioxide |
| US6300515B1 (en) * | 1999-04-15 | 2001-10-09 | Mitsubishi Chemical Corporation | Process for the isomerization of allylic compounds |
| DE102011002639A1 (de) | 2011-01-13 | 2012-07-19 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von Biphephos |
| JP7474310B2 (ja) | 2021-12-17 | 2024-04-24 | エボニック オクセノ ゲーエムベーハー ウント コー． カーゲー | Ｐｔとキサントフォスを用いるオレフィンのヒドロホルミル化方法 |
| JP7503119B2 (ja) | 2021-12-17 | 2024-06-19 | エボニック オクセノ ゲーエムベーハー ウント コー． カーゲー | Ｐｔ－キサントフォス－ヨウ素錯体及びＰｔ－キサントフォス－臭素錯体 |
| EP4198011B1 (de) | 2021-12-17 | 2024-07-31 | Evonik Oxeno GmbH & Co. KG | Verfahren zur hydroformylierung von olefinen unter einsatz von pt und dpephos |
| EP4197995A1 (de) | 2021-12-17 | 2023-06-21 | Evonik Operations GmbH | Pt-xanthen-iod-komplex und pt-xanthen-brom-komplex |
| EP4198000A1 (de) | 2021-12-17 | 2023-06-21 | Evonik Operations GmbH | Pt-xanthen-brom-komplex |
| EP4198008B1 (de) | 2021-12-17 | 2024-07-31 | Evonik Oxeno GmbH & Co. KG | Verfahren zur hydroformylierung von olefinen unter einsatz von pt und iod |
| EP4198012B1 (de) | 2021-12-17 | 2024-05-15 | Evonik Oxeno GmbH & Co. KG | Verfahren zur hydroformylierung von olefinen unter einsatz von pt und iod oder brom |
| EP4198006B1 (de) | 2021-12-17 | 2024-07-24 | Evonik Oxeno GmbH & Co. KG | Verfahren zur hydroformylierung von olefinen unter einsatz von pt und brom |
| EP4198040A1 (de) | 2021-12-17 | 2023-06-21 | Evonik Operations GmbH | Pt-dpephos-iod-komplex und pt-dpephos-brom-komplex |
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2021
- 2021-12-17 EP EP21215366.2A patent/EP4198001B1/de active Active
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2022
- 2022-12-05 JP JP2022193975A patent/JP2023090660A/ja active Pending
- 2022-12-13 US US18/064,953 patent/US12030899B2/en active Active
- 2022-12-14 KR KR1020220174573A patent/KR20230092781A/ko unknown
- 2022-12-15 CN CN202211612404.7A patent/CN116265481A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| KR20230092781A (ko) | 2023-06-26 |
| US12030899B2 (en) | 2024-07-09 |
| JP2023090660A (ja) | 2023-06-29 |
| TW202340223A (zh) | 2023-10-16 |
| EP4198001A1 (de) | 2023-06-21 |
| EP4198001B1 (de) | 2024-05-22 |
| US20230192743A1 (en) | 2023-06-22 |
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