KR20230092777A - Pt-크산텐-아이오딘 착물 및 Pt-크산텐-브로민 착물 - Google Patents
Pt-크산텐-아이오딘 착물 및 Pt-크산텐-브로민 착물 Download PDFInfo
- Publication number
- KR20230092777A KR20230092777A KR1020220174556A KR20220174556A KR20230092777A KR 20230092777 A KR20230092777 A KR 20230092777A KR 1020220174556 A KR1020220174556 A KR 1020220174556A KR 20220174556 A KR20220174556 A KR 20220174556A KR 20230092777 A KR20230092777 A KR 20230092777A
- Authority
- KR
- South Korea
- Prior art keywords
- complex
- xanthene
- iodine
- alkyl
- bromine
- Prior art date
Links
- 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 9
- 229910052794 bromium Inorganic materials 0.000 title claims abstract description 9
- 239000003446 ligand Substances 0.000 claims abstract description 23
- 238000006555 catalytic reaction Methods 0.000 claims abstract description 8
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 2
- -1 2-pentyl Chemical group 0.000 description 16
- 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
- 125000006736 (C6-C20) aryl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 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
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 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
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 2
- HOAGXXFHJQRWMT-UHFFFAOYSA-N (2-ethenylphenyl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=CC=CC=C1C=C HOAGXXFHJQRWMT-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-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
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 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
- 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
- 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
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 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
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 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
- 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
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/2247—At least one oxygen and one phosphorous atom present as complexing atoms in an at least bidentate or bridging ligand
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
- B01J31/2442—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems
- B01J31/2447—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring
- B01J31/2452—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising condensed ring systems and phosphine-P atoms as substituents on a ring of the condensed system or on a further attached ring with more than one complexing phosphine-P atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
- C07C45/505—Asymmetric hydroformylation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/828—Platinum
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Pt-크산텐-아이오딘 착물 및 Pt-크산텐-브로민 착물, 및 히드로포르밀화 반응의 촉매작용을 위한 그의 용도.
Description
본 발명은 Pt-크산텐-아이오딘 착물 및 Pt-크산텐-브로민 착물, 및 히드로포르밀화 반응의 촉매작용을 위한 그의 용도에 관한 것이다.
문헌 [C. Botteghi et al., Journal of Molecular Catalysis A: Chemical 200, (2003), 147-156]에는 2-토실옥시스티렌의 히드로포르밀화를 위한 Pt(Xantphos)Cl2의 사용이 기재되어 있다.
본 발명에 의해 해결하고자 하는 과제는 신규 착물을 제공하는 것이다. 여기서 착물은 히드로포르밀화 반응의 촉매작용에 있어서 선행 기술에 기재된 Pt의 Cl2와의 착물과 비교하여 향상된 수율을 제공하여야 한다.
상기 목적이 청구항 제1항에 따른 착물에 의해 달성된다.
하기를 포함하는 착물:
a) Pt;
b) 화학식 (I)에 따른 리간드:
여기서 R1, R2, R3, R4, R5, R6, R7, R8은 -H, -(C1-C12)-알킬, -(C6-C20)-아릴로부터 선택되고,
R9, R10은 -(C1-C12)-알킬, -(C6-C20)-아릴로부터 선택되며,
R1, R2, R3, R4, R5, R6, R7, R8, R9, R10이 -(C6-C20)-아릴인 경우에, 아릴 고리는 -(C1-C12)-알킬, -O-(C1-C12)-알킬로부터 선택된 치환기를 가질 수 있음;
c) 아이오딘 리간드 또는 브로민 리간드.
(C1-C12)-알킬이라는 표현은 1 내지 12개의 탄소 원자를 갖는 직쇄 및 분지형 알킬 기를 포괄한다. 이들은 바람직하게는 (C1-C8)-알킬 기, 보다 바람직하게는 (C1-C6)-알킬, 가장 바람직하게는 (C1-C4)-알킬이다.
적합한 (C1-C12)-알킬 기는 특히 메틸, 에틸, 프로필, 이소프로필, n-부틸, 이소-부틸, sec-부틸, tert-부틸, n-펜틸, 2-펜틸, 2-메틸부틸, 3-메틸부틸, 1,2-디메틸프로필, 1,1-디메틸프로필, 2,2-디메틸프로필, 1-에틸프로필, n-헥실, 2-헥실, 2-메틸펜틸, 3-메틸펜틸, 4-메틸펜틸, 1,1-디메틸부틸, 1,2-디메틸부틸, 2,2-디메틸부틸, 1,3-디메틸부틸, 2,3-디메틸부틸, 3,3-디메틸부틸, 1,1,2-트리메틸프로필, 1,2,2-트리메틸프로필, 1-에틸부틸, 1-에틸-2-메틸프로필, n-헵틸, 2-헵틸, 3-헵틸, 2-에틸펜틸, 1-프로필부틸, n-옥틸, 2-에틸헥실, 2-프로필헵틸, 노닐, 데실이다.
(C6-C20)-아릴이라는 표현은 6 내지 20개의 탄소 원자를 갖는 모노- 또는 폴리시클릭 방향족 히드로카르빌 라디칼을 포괄한다. 이들은 바람직하게는 (C6-C14)-아릴, 보다 바람직하게는 (C6-C10)-아릴이다.
적합한 (C6-C20)-아릴 기는 특히 페닐, 나프틸, 인데닐, 플루오레닐, 안트라세닐, 페난트레닐, 나프타세닐, 크리세닐, 피레닐, 코로네닐이다. 바람직한 (C6-C20)-아릴 기는 페닐, 나프틸 및 안트라세닐이다.
한 실시양태에서, R2, R3, R5, R6, R7, R8은 -(C1-C12)-알킬, -(C6-C20)-아릴로부터 선택된다.
한 실시양태에서, R5, R6, R7, R8은 -(C6-C20)-아릴이다.
한 실시양태에서, R5 및 R6은 상이한 라디칼이고, R7 및 R8은 상이한 라디칼이다.
한 실시양태에서, R2 및 R3은 -(C1-C12)-알킬이다.
한 실시양태에서, R2 및 R3은 -CH3이다.
한 실시양태에서, R1 및 R4는 -H이다.
한 실시양태에서, R9 및 R10은 -(C1-C12)-알킬이다.
한 실시양태에서, R9 및 R10은 -tBu이다.
한 실시양태에서, 화학식 (I)에 따른 리간드는 구조 (1)을 갖는다:
한 실시양태에서, 착물은 정확히 1개의 화학식 (I)에 따른 리간드를 갖는다.
한 실시양태에서, 착물은 적어도 2개의 아이오딘 리간드를 갖는다.
한 실시양태에서, 착물은 정확히 2개의 아이오딘 리간드를 갖는다.
한 실시양태에서, 착물은 적어도 2개의 브로민 리간드를 갖는다.
한 실시양태에서, 착물은 정확히 2개의 브로민 리간드를 갖는다.
착물 그 자체와 함께, 히드로포르밀화 반응의 촉매작용을 위한 그의 용도가 또한 청구된다.
히드로포르밀화 반응의 촉매작용을 위한 상기 기재된 바와 같은 착물의 용도.
본 발명이 하기에서 작업 실시예를 참조로 하여 보다 상세히 설명될 것이다.
실험 설명
바이알에 PtX2 (X = 할로겐), 리간드, 및 오븐-건조된 교반 막대를 충전하였다. 이어서, 바이알을 격막 (PTFE-코팅된 스티렌-부타디엔 고무) 및 페놀계 수지 캡으로 밀봉하였다. 바이알을 3회 배기시키고 아르곤을 재충전하였다. 톨루엔 및 1-옥텐을 시린지를 사용하여 바이알에 첨가하였다. 바이알을 합금 플레이트에 위치시켜, 이를 아르곤 분위기 하의 파르 인스트루먼츠(Parr Instruments)로부터의 4560 시리즈 오토클레이브로 옮겼다. 오토클레이브를 CO/H2로 3회 퍼징한 후에, 합성 가스 압력을 실온에서 40 bar로 증가시켰다. 반응을 80℃에서 18 h 동안 수행하였다. 반응이 종료되면, 오토클레이브를 실온으로 냉각시키고, 조심스럽게 감압시켰다. 수율 및 선택성을 GC 분석에 의해 결정하였다.
할로겐의 변화
반응 조건:
1.0 mmol의 1-옥텐, 0.5 mol%의 PtX2, 2.0 당량의 리간드 (1), 용매: 톨루엔, p(CO/H2): 40 bar, T: 80℃, t: 18 h.
수율:
실험 결과가 제시하는 바와 같이, 상기 목적이 본 발명에 따른 착물에 의해 달성된다.
Claims (13)
- 하기를 포함하는 착물:
a) Pt;
b) 화학식 (I)에 따른 리간드:
여기서 R1, R2, R3, R4, R5, R6, R7, R8은 -H, -(C1-C12)-알킬, -(C6-C20)-아릴로부터 선택되고,
R9, R10은 -(C1-C12)-알킬, -(C6-C20)-아릴로부터 선택되며,
R1, R2, R3, R4, R5, R6, R7, R8, R9, R10이 -(C6-C20)-아릴인 경우에, 아릴 고리는 -(C1-C12)-알킬, -O-(C1-C12)-알킬로부터 선택된 치환기를 가질 수 있음;
c) 아이오딘 리간드 또는 브로민 리간드. - 제1항에 있어서, R2, R3, R5, R6, R7, R8이 -(C1-C12)-알킬, -(C6-C20)-아릴로부터 선택되는 것인 착물.
- 제1항 또는 제2항에 있어서, R5, R6, R7, R8이 -(C6-C20)-아릴인 착물.
- 제1항 내지 제3항 중 어느 한 항에 있어서, R2 및 R3이 -(C1-C12)-알킬인 착물.
- 제1항 내지 제4항 중 어느 한 항에 있어서, R1 및 R4가 -H인 착물.
- 제1항 내지 제5항 중 어느 한 항에 있어서, R9 및 R10이 -(C1-C12)-알킬인 착물.
- 제1항 내지 제6항 중 어느 한 항에 있어서, 화학식 (I)에 따른 리간드가 구조 (1)을 갖는 것인 착물:
- 제1항 내지 제7항 중 어느 한 항에 있어서, 착물이 정확히 1개의 화학식 (I)에 따른 리간드를 갖는 것인 착물.
- 제1항 내지 제8항 중 어느 한 항에 있어서, 착물이 적어도 2개의 아이오딘 리간드를 갖는 것인 착물.
- 제9항에 있어서, 착물이 정확히 2개의 아이오딘 리간드를 갖는 것인 착물.
- 제1항 내지 제8항 중 어느 한 항에 있어서, 착물이 적어도 2개의 브로민 리간드를 갖는 것인 착물.
- 제11항에 있어서, 착물이 정확히 2개의 브로민 리간드를 갖는 것인 착물.
- 히드로포르밀화 반응의 촉매작용을 위한 제1항 내지 제12항 중 어느 한 항에 따른 착물의 용도.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP21215337.3 | 2021-12-17 | ||
| EP21215337.3A EP4197995A1 (de) | 2021-12-17 | 2021-12-17 | Pt-xanthen-iod-komplex und pt-xanthen-brom-komplex |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20230092777A true KR20230092777A (ko) | 2023-06-26 |
Family
ID=78918508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020220174556A KR20230092777A (ko) | 2021-12-17 | 2022-12-14 | Pt-크산텐-아이오딘 착물 및 Pt-크산텐-브로민 착물 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US11912726B2 (ko) |
| EP (1) | EP4197995A1 (ko) |
| JP (1) | JP7491987B2 (ko) |
| KR (1) | KR20230092777A (ko) |
| CN (1) | CN116265480A (ko) |
| TW (1) | TW202328160A (ko) |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101600674B (zh) | 2006-11-30 | 2013-09-11 | 巴斯夫欧洲公司 | 烯烃的加氢甲酰化方法 |
| US8173830B2 (en) * | 2009-05-07 | 2012-05-08 | Celanese International Corporation | Vinyl ester production from acetylene and carboxylic acid utilizing homogeneous catalyst |
| WO2017191310A1 (de) * | 2016-05-06 | 2017-11-09 | Basf Se | P-chirale phosphinliganden und deren verwendung zur asymmetrischen synthese |
| 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 |
| EP4198040A1 (de) | 2021-12-17 | 2023-06-21 | Evonik Operations GmbH | Pt-dpephos-iod-komplex und pt-dpephos-brom-komplex |
| EP4198008A1 (de) | 2021-12-17 | 2023-06-21 | Evonik Operations GmbH | Verfahren zur hydroformylierung von olefinen unter einsatz von pt und iod |
| 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 |
| EP4198011A1 (de) | 2021-12-17 | 2023-06-21 | Evonik Operations GmbH | Verfahren zur hydroformylierung von olefinen unter einsatz von pt und dpephos |
| 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 |
| EP4198000A1 (de) | 2021-12-17 | 2023-06-21 | Evonik Operations GmbH | Pt-xanthen-brom-komplex |
| EP4198006A1 (de) | 2021-12-17 | 2023-06-21 | Evonik Operations GmbH | Verfahren zur hydroformylierung von olefinen unter einsatz von pt und brom |
-
2021
- 2021-12-17 EP EP21215337.3A patent/EP4197995A1/de active Pending
-
2022
- 2022-12-05 JP JP2022193976A patent/JP7491987B2/ja active Active
- 2022-12-13 US US18/064,952 patent/US11912726B2/en active Active
- 2022-12-14 TW TW111147943A patent/TW202328160A/zh unknown
- 2022-12-14 KR KR1020220174556A patent/KR20230092777A/ko unknown
- 2022-12-15 CN CN202211612373.5A patent/CN116265480A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP7491987B2 (ja) | 2024-05-28 |
| JP2023090661A (ja) | 2023-06-29 |
| CN116265480A (zh) | 2023-06-20 |
| EP4197995A1 (de) | 2023-06-21 |
| TW202328160A (zh) | 2023-07-16 |
| US11912726B2 (en) | 2024-02-27 |
| US20230192742A1 (en) | 2023-06-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP7474306B2 (ja) | Ｐｔと臭素を用いるオレフィンのヒドロホルミル化方法 | |
| JP7474307B2 (ja) | Ｐｔとヨウ素又は臭素を用いるオレフィンのヒドロホルミル化方法 | |
| KR20230092778A (ko) | Pt-크산텐-브로민 착물 | |
| JP7503119B2 (ja) | 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 | |
| KR20230092783A (ko) | Pt-DPEphos-아이오딘 착물 및 Pt-DPEphos-브로민 착물 | |
| JP7474308B2 (ja) | Ｐｔとヨウ素を用いるオレフィンのヒドロホルミル化方法 | |
| JP7474310B2 (ja) | 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 | |
| JP7474309B2 (ja) | ＰｔとＤＰＥフォスを用いるオレフィンのヒドロホルミル化方法 | |
| KR20230092777A (ko) | Pt-크산텐-아이오딘 착물 및 Pt-크산텐-브로민 착물 | |
| KR20230092781A (ko) | Pt-비페닐-아이오딘 착물 및 Pt-비페닐-브로민 착물 | |
| TWI846204B (zh) | 使用Ｐｔ及雙〔（２－二苯基膦）苯基〕醚（ＤＰＥｐｈｏｓ）之烯烴的氫甲醯化方法 | |
| US12030899B2 (en) | Pt-biphenyl-iodine complex and Pt-biphenyl-bromine complex | |
| TWI843336B (zh) | 使用鉑（Ｐｔ）和塞尚弗（ｔｈｉｘａｎｔｐｈｏｓ）之烯烴的氫甲醯化方法 |