CN116265479A - 铂-Thixantphos-碘配合物和铂-Thixantphos-溴配合物 - Google Patents
铂-Thixantphos-碘配合物和铂-Thixantphos-溴配合物 Download PDFInfo
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 title claims description 8
- 229910052794 bromium Inorganic materials 0.000 title claims description 8
- 229910052740 iodine Inorganic materials 0.000 title claims description 8
- 239000011630 iodine Substances 0.000 title claims description 8
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract description 8
- 239000003446 ligand Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 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
- 150000001875 compounds Chemical class 0.000 claims description 2
- -1 1, 1-dimethylbutyl Chemical group 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- 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
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 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
- 239000002904 solvent Substances 0.000 description 2
- 125000005918 1,2-dimethylbutyl group Chemical group 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
- KJALUUCEMMPKAC-ONEGZZNKSA-N methyl (e)-pent-3-enoate Chemical compound COC(=O)C\C=C\C KJALUUCEMMPKAC-ONEGZZNKSA-N 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
- 125000002524 organometallic group Chemical group 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
- 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
- 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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Abstract
本发明涉及铂‑Thixantphos‑碘配合物和铂‑Thixantphos‑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-Thixantphos-碘配合物和铂-Thixantphos-溴配合物，及其用于催化加氢甲酰化反应的用途。
背景技术
P. Meessen等人，Journal of Organometallic Chemistry, 551, (1998), 165-170描述了ThixantphosPtCl2用于3-戊烯酸甲酯的加氢甲酰化的用途
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，该配合物应提供好的产率。
该目的通过根据权利要求1所述的配合物实现。
配合物，包含：
a) Pt；
b) 符合式(I)的配体：
其中R1、R2、R3、R4、R5、R6、R7、R8选自：-H、-(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。
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，R5、R6、R7、R8是-(C6-C20)-芳基。
在一个实施方案中，R5、R6、R7、R8是-Ph。
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-CH3。
在一个实施方案中，R2和R3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80℃下进行18 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。
1-辛烯的加氢甲酰化
反应条件：
1.0 mmol的1-辛烯，0.5 mol%的PtI2，2.0当量的配体，溶剂：甲苯，p(CO/H2)：40巴，T：80℃，t：18 h。
| 配体 | 产率(%) |
 |
PtI2*: 99。 |
*根据本发明的方法
卤素的变化
反应条件：
10 mmol的1-辛烯，0.1 mol%的PtX2，2.2当量的配体(1)，溶剂：甲苯，p(CO/H2)：40巴，T：80℃，t：20 h。
产率：
PtI2：95%
PtBr2：48%
PtCl2：<1%。
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，包含：
a) Pt；
b) 符合式(I)的配体：
其中R1、R2、R3、R4、R5、R6、R7、R8选自：-H、-(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R5、R6、R7、R8是-(C6-C20)-芳基。
3.根据权利要求1或2任一项所述的配合物，
其中R5、R6、R7、R8是-Ph。
4.根据权利要求1至3中任一项所述的配合物，
其中R1和R4是-(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R2和R3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。
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