TW202334071A - 鉑－雙〔（２－二苯基膦基）苯基〕醚－碘（Ｐｔ－ＤＰＥｐｈｏｓ－ｉｏｄｉｎｅ）錯合物及鉑－雙〔（２－二苯基膦基）苯基〕醚－溴錯合物 - Google Patents
鉑－雙〔（２－二苯基膦基）苯基〕醚－碘（Ｐｔ－ＤＰＥｐｈｏｓ－ｉｏｄｉｎｅ）錯合物及鉑－雙〔（２－二苯基膦基）苯基〕醚－溴錯合物 Download PDFInfo
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- Prior art keywords
- complex
- dpephos
- iodine
- bromine
- ligand
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- 229910052740 iodine Inorganic materials 0.000 title claims abstract description 10
- 239000011630 iodine Substances 0.000 title claims abstract description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 229910052794 bromium Inorganic materials 0.000 title claims abstract description 8
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract description 8
- 239000003446 ligand Substances 0.000 claims description 18
- 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
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 abstract description 2
- -1 2-pentyl Chemical group 0.000 description 19
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
- 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
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- 125000005919 1,2,2-trimethylpropyl 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
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 1
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 1
- 125000000217 alkyl 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
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 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
- 238000011010 flushing procedure Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 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
- 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
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([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
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 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
- 125000001725 pyrenyl group Chemical group 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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
- C07F15/0093—Platinum compounds without a metal-carbon linkage
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- C07—ORGANIC CHEMISTRY
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- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
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- 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
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Abstract
鉑-雙[(2-二苯基膦基)苯基]醚-碘(Pt-DPEphos-iodine)錯合物及鉑-雙[(2-二苯基膦基)苯基]醚-溴錯合物，及其用於催化氫甲醯化反應的用途。
Description
本發明係關於鉑-雙[(2-二苯基膦基)苯基]醚-碘(Pt-DPEphos-iodine)錯合物及鉑-雙[(2-二苯基膦基)苯基]醚-溴錯合物，以及其用於催化氫甲醯化反應的用途。
P. Meessen等人，Journal of Organometallic Chemistry，551，(1998)，165-170描述了DPEphosPtCl
2用於3-戊烯酸甲酯之氫甲醯化的用途。
本發明的目的是提供新穎錯合物。與先前技術中所描述的錯合物相比，這裡的錯合物係在氫甲醯化反應的催化中提供增加的產率。
此目的係藉由根據請求項1的錯合物來達成。
錯合物包含：
a) Pt；
b) 符合式(I)之配位基：
其中R
1、R
2、R
3、R
4、R
5、R
6、R
7、R
8係選自：-H、-(C
1-C
12)-烷基、-(C
6-C
20)-芳基，且R
5、R
6、R
7、R
8基團中至少二者為-(C
6-C
20)-芳基；
c) 碘配位基或溴配位基。
表達用語(C
1-C
12)-烷基包含具有1至12個碳原子的直鏈和支鏈烷基。這些較佳為(C
1-C
8)-烷基，更佳為(C
1-C
6)-烷基，最佳為(C
1-C
4)-烷基。
合適的(C
1-C
12)-烷基尤其是甲基、乙基、丙基、異丙基、正丁基、異丁基、二級-丁基、三級-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。
表達用語(C
6-C
20)-芳基包含具有6至20個碳原子的單-或多環芳香族烴基基團。這些較佳為(C
6-C
14)-芳基，更佳為(C
6-C
10)-芳基。
合適的(C
6-C
20)-芳基尤其是苯基、萘基、茚基、茀基、蒽基、菲基、稠四苯基、基(chrysenyl)、芘基、蔻基。較佳的(C
6-C
20)-芳基為苯基、萘基及蒽基。
在一個具體實施態樣中，R
5、R
6、R
7、R
8為-(C
6-C
20)-芳基。
在一個具體實施態樣中，R
5、R
6、R
7、R
8為-Ph。
在一個具體實施態樣中，R
1和R
4各者為-H。
在一個具體實施態樣中，R
2和R
3各者為-H。
在一個具體實施態樣中，該式(I)之化合物具有結構(
1)：
。
在一個具體實施態樣中，該錯合物具有正好一個對應於式(I)之配位基。
在一個具體實施態樣中，該錯合物具有至少二個碘配位基。
在一個具體實施態樣中，該錯合物具有正好二個碘配位基。
在一個具體實施態樣中，該錯合物具有至少二個溴配位基。
在一個具體實施態樣中，該錯合物具有正好兩個溴配位基。
除了該錯合物本身外，亦主張其用於催化氫甲醯化反應的用途。
如上所述之錯合物用於催化氫甲醯化反應的用途。
在下文中將參照工作實施例更詳細地說明本發明。
實驗說明
於小瓶中裝入PtX
2(X=鹵素)、配位基、及烘乾攪拌棒。然後用隔膜(PTFE被覆之苯乙烯-丁二烯橡膠)和酚醛蓋密封小瓶。將小瓶抽空並再充滿氬三次。使用注射器將甲苯和1-辛烯添加到小瓶中。將小瓶置於合金板中，將其在氬氣氛下轉移至來自Parr Instruments的4560系列高壓釜。用CO/H
2沖洗高壓釜三次後，在室溫下將合成氣體壓力增加至40巴。反應係在120℃下進行20小時。在反應終止時，將高壓釜冷卻至室溫並小心地減壓。藉由GC分析決定產率和選擇性。
1-辛烯的氫甲醯化
反應條件：
10.0毫莫耳的1-辛烯，0.1莫耳% PtX
2，2.2當量的配位基，溶劑：甲苯，p(CO/H
2)：40巴，T：120℃，t：20小時。
產率：
如實驗結果顯示，該目的係藉由根據本發明之錯合物而達成。
Claims (12)
- 一種錯合物，其包含： a) Pt； b) 符合式(I)之配位基： 其中R 1、R 2、R 3、R 4、R 5、R 6、R 7、R 8係選自：-H、-(C 1-C 12)-烷基、-(C 6-C 20)-芳基，且R 5、R 6、R 7、R 8基團中至少二者為-(C 6-C 20)-芳基； c) 碘配位基或溴配位基。
- 如請求項1之錯合物，其中R 5、R 6、R 7、R 8為-(C 6-C 20)-芳基。
- 如請求項1或2中任一項之錯合物，其中R 5、R 6、R 7、R 8為-Ph。
- 如請求項1至3中任一項之錯合物，其中R 1和R 4各者為-H。
- 如請求項1至4中任一項之錯合物，其中R 2和R 3各者為-H。
- 如請求項1至5中任一項之錯合物，其中該式(I)之化合物具有結構( 1)： 。
- 如請求項1至6中任一項之錯合物，其中該錯合物具有正好一個符合該式(I)之配位基。
- 如請求項1至7中任一項之錯合物，其中該錯合物具有兩個碘配位基。
- 如請求項8之錯合物，其中該錯合物具有正好兩個碘配位基。
- 如請求項1至7中任一項之錯合物，其中該錯合物具有至少兩個溴配位基。
- 如請求項10之錯合物，其中該錯合物具有正好兩個溴配位基。
- 一種如請求項1至11中任一項之錯合物的用途，其係用於催化氫甲醯化反應。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP21215377.9A EP4198040A1 (de) | 2021-12-17 | 2021-12-17 | Pt-dpephos-iod-komplex und pt-dpephos-brom-komplex |
| EP21215377.9 | 2021-12-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW202334071A true TW202334071A (zh) | 2023-09-01 |
Family
ID=78918478
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW111147945A TW202334071A (zh) | 2021-12-17 | 2022-12-14 | 鉑－雙〔（２－二苯基膦基）苯基〕醚－碘（Ｐｔ－ＤＰＥｐｈｏｓ－ｉｏｄｉｎｅ）錯合物及鉑－雙〔（２－二苯基膦基）苯基〕醚－溴錯合物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20230192741A1 (zh) |
| EP (1) | EP4198040A1 (zh) |
| JP (1) | JP2023090662A (zh) |
| KR (1) | KR20230092783A (zh) |
| CN (1) | CN116265478A (zh) |
| TW (1) | TW202334071A (zh) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4197995A1 (de) | 2021-12-17 | 2023-06-21 | Evonik Operations GmbH | Pt-xanthen-iod-komplex und pt-xanthen-brom-komplex |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8173830B2 (en) * | 2009-05-07 | 2012-05-08 | Celanese International Corporation | Vinyl ester production from acetylene and carboxylic acid utilizing homogeneous catalyst |
-
2021
- 2021-12-17 EP EP21215377.9A patent/EP4198040A1/de active Pending
-
2022
- 2022-12-05 JP JP2022193977A patent/JP2023090662A/ja active Pending
- 2022-12-13 US US18/064,949 patent/US20230192741A1/en active Pending
- 2022-12-14 KR KR1020220174595A patent/KR20230092783A/ko unknown
- 2022-12-14 TW TW111147945A patent/TW202334071A/zh unknown
- 2022-12-15 CN CN202211612199.4A patent/CN116265478A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2023090662A (ja) | 2023-06-29 |
| EP4198040A1 (de) | 2023-06-21 |
| KR20230092783A (ko) | 2023-06-26 |
| US20230192741A1 (en) | 2023-06-22 |
| CN116265478A (zh) | 2023-06-20 |
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