CA1264055A - Reactions catalysees par un complexe de metal de transition - Google Patents

Reactions catalysees par un complexe de metal de transition

Info

Publication number: CA1264055A
Authority: CA; Canada
Prior art keywords: radical; group; radicals; carbon atoms; ligand
Prior art date: 1984-02-17
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.): Expired

Application number

CA000580692A

Other languages

English (en)

Inventor

Ernst Billig

Anthony George Abatjoglou

David Robert Bryant

Rex Eugene Murray

John Michael Maher

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Union Carbide Chemicals and Plastics Technology LLC

Original Assignee

Union Carbide Chemicals and Plastics Technology LLC

Priority date (The priority date 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 date listed.)

1984-02-17

Filing date

1988-10-19

Publication date

1989-12-27

1984-12-28 Priority claimed from US06/685,025 external-priority patent/US4599206A/en

1988-10-19 Application filed by Union Carbide Chemicals and Plastics Technology LLC filed Critical Union Carbide Chemicals and Plastics Technology LLC

1988-10-19 Priority to CA000580692A priority Critical patent/CA1264055A/fr

1989-12-27 Application granted granted Critical

1989-12-27 Publication of CA1264055A publication Critical patent/CA1264055A/fr

Status Expired legal-status Critical Current

Links

150000003624 transition metals Chemical class 0.000 title claims description 21
229910052723 transition metal Inorganic materials 0.000 title claims description 20
238000006555 catalytic reaction Methods 0.000 title description 2
239000003446 ligand Substances 0.000 claims abstract description 258
238000000034 method Methods 0.000 claims abstract description 144
230000008569 process Effects 0.000 claims abstract description 125
238000007037 hydroformylation reaction Methods 0.000 claims abstract description 122
239000003054 catalyst Substances 0.000 claims abstract description 97
239000000203 mixture Substances 0.000 claims abstract description 31
238000005810 carbonylation reaction Methods 0.000 claims abstract description 24
230000007704 transition Effects 0.000 claims abstract description 24
230000006315 carbonylation Effects 0.000 claims abstract description 20
-1 hydrocarbon radical Chemical class 0.000 claims description 227
239000010948 rhodium Substances 0.000 claims description 126
229910052703 rhodium Inorganic materials 0.000 claims description 122
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 112
150000003254 radicals Chemical class 0.000 claims description 100
238000006243 chemical reaction Methods 0.000 claims description 71
229910052739 hydrogen Inorganic materials 0.000 claims description 68
239000001257 hydrogen Substances 0.000 claims description 68
239000007788 liquid Substances 0.000 claims description 65
125000004432 carbon atom Chemical group C* 0.000 claims description 64
150000001336 alkenes Chemical class 0.000 claims description 49
239000007789 gas Substances 0.000 claims description 49
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 41
229910002091 carbon monoxide Inorganic materials 0.000 claims description 36
150000002431 hydrogen Chemical class 0.000 claims description 34
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 33
239000002243 precursor Substances 0.000 claims description 31
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 28
IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
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125000003118 aryl group Chemical group 0.000 claims description 25
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238000000926 separation method Methods 0.000 claims description 11
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125000002252 acyl group Chemical group 0.000 claims description 9
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
239000007858 starting material Substances 0.000 claims description 9
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 8
125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 8
125000005499 phosphonyl group Chemical group 0.000 claims description 8
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 8
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239000004793 Polystyrene Substances 0.000 claims description 5
125000004429 atom Chemical group 0.000 claims description 5
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125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
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YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical group [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims 1
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239000000047 product Substances 0.000 description 104
150000002500 ions Chemical class 0.000 description 54
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 51
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239000000243 solution Substances 0.000 description 41
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
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239000011347 resin Substances 0.000 description 25
229910052698 phosphorus Inorganic materials 0.000 description 24
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238000002474 experimental method Methods 0.000 description 20
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239000006227 byproduct Substances 0.000 description 19
239000011521 glass Substances 0.000 description 18
229910052757 nitrogen Inorganic materials 0.000 description 18
229940116254 phosphonic acid Drugs 0.000 description 18
239000011574 phosphorus Substances 0.000 description 18
239000002253 acid Substances 0.000 description 15
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 13
229910052751 metal Inorganic materials 0.000 description 13
239000002184 metal Substances 0.000 description 13
239000002904 solvent Substances 0.000 description 13
101100412856 Mus musculus Rhod gene Proteins 0.000 description 12
101100242191 Tetraodon nigroviridis rho gene Proteins 0.000 description 12
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
241000282326 Felis catus Species 0.000 description 11
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 11
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 11
238000011282 treatment Methods 0.000 description 11
239000001893 (2R)-2-methylbutanal Substances 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
239000000463 material Substances 0.000 description 10
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125000002768 hydroxyalkyl group Chemical group 0.000 description 9
238000012545 processing Methods 0.000 description 9
238000010926 purge Methods 0.000 description 9
230000002411 adverse Effects 0.000 description 8
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 8
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 7
150000001450 anions Chemical class 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
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BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
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239000004305 biphenyl Substances 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
238000005755 formation reaction Methods 0.000 description 6
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241000894007 species Species 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 5
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230000002844 continuous effect Effects 0.000 description 5
125000003438 dodecyl 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])C([H])([H])C([H])([H])* 0.000 description 5
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 5
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150000008301 phosphite esters Chemical class 0.000 description 5
238000001556 precipitation Methods 0.000 description 5
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238000004458 analytical method Methods 0.000 description 4
GGRQQHADVSXBQN-FGSKAQBVSA-N carbon monoxide;(z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].[O+]#[C-].[O+]#[C-].C\C(O)=C\C(C)=O GGRQQHADVSXBQN-FGSKAQBVSA-N 0.000 description 4
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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 4
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SHFGJEQAOUMGJM-UHFFFAOYSA-N dialuminum dipotassium disodium dioxosilane iron(3+) oxocalcium oxomagnesium oxygen(2-) Chemical compound [O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[Na+].[Na+].[Al+3].[Al+3].[K+].[K+].[Fe+3].[Fe+3].O=[Mg].O=[Ca].O=[Si]=O SHFGJEQAOUMGJM-UHFFFAOYSA-N 0.000 description 2
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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA000580692A 1984-02-17 1988-10-19 Reactions catalysees par un complexe de metal de transition Expired CA1264055A (fr)

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Application Number	Priority Date	Filing Date	Title
CA000580692A CA1264055A (fr)	1984-02-17	1988-10-19	Reactions catalysees par un complexe de metal de transition

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US58135284A	1984-02-17	1984-02-17
US581,352		1984-02-17
US06/685,025 US4599206A (en)	1984-02-17	1984-12-28	Transition metal complex catalyzed reactions
US685,025		1984-12-28
CA000472950A CA1262915A1 (fr)	1984-02-17	1985-01-25	Reactions catalytiques aux complexes de metal de transition
CA000580692A CA1264055A (fr)	1984-02-17	1988-10-19	Reactions catalysees par un complexe de metal de transition

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CA000472950A Division CA1262915A1 (fr)	1984-02-17	1985-01-25	Reactions catalytiques aux complexes de metal de transition

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1988
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Publication	Publication Date	Title
AU579144B2 (en)	1988-11-17	Carboxylation process
US4717775A (en)	1988-01-05	Transition metal complex catalyzed reactions
US4885401A (en)	1989-12-05	Bis-phosphite compounds
US4748261A (en)	1988-05-31	Bis-phosphite compounds
RU2699368C2 (ru)	2019-09-05	Способ гидроформилирования
US4769498A (en)	1988-09-06	Transition metal complex catalyzed processes
EP0697391B1 (fr)	1998-10-28	Stabilisation des ligands phosphites dans le procédé d'hydroformylation
KR100198688B1 (ko)	1999-06-15	하이드로포밀화 방법
AU722459B2 (en)	2000-08-03	Improved metal-ligand complex catalyzed processes
EP0518241B1 (fr)	1996-09-11	Procédé d'hydroformylation et composé bisphosphite utilisé
AU720249B2 (en)	2000-05-25	Improved metal-ligand complex catalyzed processes
KR102362007B1 (ko)	2022-02-11	하이드로포르밀화 공정
US4789753A (en)	1988-12-06	Phosphite ligands
US20150133695A1 (en)	2015-05-14	Hydroformylation process
EP1312598B1 (fr)	2005-02-16	Procédé pour la préparation d' aldéhydes
US11976017B2 (en)	2024-05-07	Processes for preparing isoprene and mono-olefins comprising at least six carbon atoms
CA1264055A (fr)	1989-12-27	Reactions catalysees par un complexe de metal de transition
EP3990176B1 (fr)	2024-11-06	Processus de préparation d'une solution à partir d'un processus d'hydroformylation pour la récupération de métaux précieux
KR920003119B1 (ko)	1992-04-20	카보닐화 방법, 로듐 착화합물 촉매 및 촉매 전구체 조성물
JP3291421B2 (ja)	2002-06-10	ヒドロホルミル化方法におけるホスフィットリガンドの安定化
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