CN1617892A - 载体上的双(磷)配体及其在催化中的应用 - Google Patents
载体上的双(磷)配体及其在催化中的应用 Download PDFInfo
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- CN1617892A CN1617892A CNA028275136A CN02827513A CN1617892A CN 1617892 A CN1617892 A CN 1617892A CN A028275136 A CNA028275136 A CN A028275136A CN 02827513 A CN02827513 A CN 02827513A CN 1617892 A CN1617892 A CN 1617892A
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- Prior art keywords
- polymer
- alkyl
- group
- acid
- aryl
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- 239000003446 ligand Substances 0.000 title claims abstract description 104
- 229910052698 phosphorus Inorganic materials 0.000 title claims abstract description 39
- 239000011574 phosphorus Substances 0.000 title claims abstract description 36
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 30
- 238000006555 catalytic reaction Methods 0.000 title description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 78
- 238000000034 method Methods 0.000 claims abstract description 74
- 230000008569 process Effects 0.000 claims abstract description 51
- 238000007037 hydroformylation reaction Methods 0.000 claims abstract description 29
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000006317 isomerization reaction Methods 0.000 claims abstract description 26
- 229910052751 metal Inorganic materials 0.000 claims abstract description 25
- 239000002184 metal Substances 0.000 claims abstract description 25
- 238000005669 hydrocyanation reaction Methods 0.000 claims abstract description 17
- 230000003197 catalytic effect Effects 0.000 claims abstract description 12
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 9
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 100
- 229920000642 polymer Polymers 0.000 claims description 91
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 42
- -1 benzyl halide Chemical class 0.000 claims description 40
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 31
- 150000002009 diols Chemical class 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 24
- 229910052723 transition metal Inorganic materials 0.000 claims description 22
- 150000003624 transition metals Chemical class 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 21
- 150000005215 alkyl ethers Chemical group 0.000 claims description 19
- 150000008378 aryl ethers Chemical group 0.000 claims description 19
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 18
- 150000001336 alkenes Chemical class 0.000 claims description 17
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 17
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 14
- DVWQNBIUTWDZMW-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalen-2-ol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=CC=CC2=C1 DVWQNBIUTWDZMW-UHFFFAOYSA-N 0.000 claims description 13
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminium flouride Chemical compound F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 claims description 12
- 239000011592 zinc chloride Substances 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 150000004292 cyclic ethers Chemical class 0.000 claims description 10
- 125000000524 functional group Chemical group 0.000 claims description 10
- 239000002841 Lewis acid Substances 0.000 claims description 9
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical group ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 9
- 150000007517 lewis acids Chemical class 0.000 claims description 9
- 229920002223 polystyrene Polymers 0.000 claims description 9
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 8
- WBAXCOMEMKANRN-UHFFFAOYSA-N 2-methylbut-3-enenitrile Chemical compound C=CC(C)C#N WBAXCOMEMKANRN-UHFFFAOYSA-N 0.000 claims description 7
- 239000004793 Polystyrene Substances 0.000 claims description 7
- 229910015844 BCl3 Inorganic materials 0.000 claims description 6
- 229910005267 GaCl3 Inorganic materials 0.000 claims description 6
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 229920003060 Poly(vinyl benzyl chloride) Polymers 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 6
- 229910007932 ZrCl4 Inorganic materials 0.000 claims description 6
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 claims description 6
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 claims description 6
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 150000002170 ethers Chemical class 0.000 claims description 6
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 6
- 150000003839 salts Chemical group 0.000 claims description 6
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 6
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 claims description 6
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 6
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims description 6
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 claims description 6
- 239000005062 Polybutadiene Substances 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 229940073608 benzyl chloride Drugs 0.000 claims description 5
- 150000002978 peroxides Chemical class 0.000 claims description 5
- 229920002857 polybutadiene Polymers 0.000 claims description 5
- 150000008648 triflates Chemical class 0.000 claims description 5
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 claims description 4
- 125000005490 tosylate group Chemical group 0.000 claims description 4
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 claims description 4
- SLBOQBILGNEPEB-UHFFFAOYSA-N 1-chloroprop-2-enylbenzene Chemical compound C=CC(Cl)C1=CC=CC=C1 SLBOQBILGNEPEB-UHFFFAOYSA-N 0.000 claims description 3
- 150000004703 alkoxides Chemical class 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 239000001913 cellulose Substances 0.000 claims description 3
- 229920002678 cellulose Polymers 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 3
- CKHJYUSOUQDYEN-UHFFFAOYSA-N gallium(3+) Chemical compound [Ga+3] CKHJYUSOUQDYEN-UHFFFAOYSA-N 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- 150000001649 bromium compounds Chemical class 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 150000004694 iodide salts Chemical class 0.000 claims 1
- 239000011968 lewis acid catalyst Substances 0.000 claims 1
- 150000002894 organic compounds Chemical class 0.000 abstract description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 70
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 69
- 239000007787 solid Substances 0.000 description 52
- 238000006243 chemical reaction Methods 0.000 description 45
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 38
- 229920001367 Merrifield resin Polymers 0.000 description 36
- HBAHZZVIEFRTEY-UHFFFAOYSA-N 2-heptylcyclohex-2-en-1-one Chemical compound CCCCCCCC1=CCCCC1=O HBAHZZVIEFRTEY-UHFFFAOYSA-N 0.000 description 35
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- CFEYBLWMNFZOPB-UHFFFAOYSA-N Allylacetonitrile Natural products C=CCCC#N CFEYBLWMNFZOPB-UHFFFAOYSA-N 0.000 description 19
- 239000010948 rhodium Substances 0.000 description 19
- 238000000921 elemental analysis Methods 0.000 description 17
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 16
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 15
- UVKXJAUUKPDDNW-NSCUHMNNSA-N (e)-pent-3-enenitrile Chemical compound C\C=C\CC#N UVKXJAUUKPDDNW-NSCUHMNNSA-N 0.000 description 14
- 238000001914 filtration Methods 0.000 description 14
- GDLCVAIEPUCSCE-UHFFFAOYSA-N chloro-bis(2-methylphenoxy)phosphane Chemical compound CC1=CC=CC=C1OP(Cl)OC1=CC=CC=C1C GDLCVAIEPUCSCE-UHFFFAOYSA-N 0.000 description 11
- DQTRYXANLKJLPK-UHFFFAOYSA-N chlorophosphonous acid Chemical class OP(O)Cl DQTRYXANLKJLPK-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- GSRUZHHLGCHAPQ-UHFFFAOYSA-N chloro-bis(2-propan-2-ylphenoxy)phosphane Chemical compound CC(C)C1=CC=CC=C1OP(Cl)OC1=CC=CC=C1C(C)C GSRUZHHLGCHAPQ-UHFFFAOYSA-N 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 9
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 150000001299 aldehydes Chemical class 0.000 description 9
- 150000002825 nitriles Chemical class 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 229910052703 rhodium Inorganic materials 0.000 description 8
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- FRQSVNHXKTZEJA-UHFFFAOYSA-N 2-(2-hydroxy-3,5,6-trimethylphenyl)-3,4,6-trimethylphenol Chemical compound CC1=CC(C)=C(O)C(C=2C(=C(C)C=C(C)C=2C)O)=C1C FRQSVNHXKTZEJA-UHFFFAOYSA-N 0.000 description 5
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- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 4
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
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- 239000001257 hydrogen Substances 0.000 description 4
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- 239000007788 liquid Substances 0.000 description 4
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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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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- 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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- 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
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- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
Description
实施例 | 载体上的配体/载体上的催化剂 | 3PN/2M3比例 |
15-1 | SL/SC 1 | 4.9 |
15-2 | SL/SC 2 | 0.2 |
15-3 | SL/SC 3 | 18.3 |
15-4 | SL/SC 4 | 1.3 |
15-5 | SL/SC 5 | 18.5 |
15-6 | SL/SC 6 | 11.5 |
15-8 | SL/SC 8 | 0.6 |
15-9 | SL/SC 9 | 17.5 |
15-10 | SL/SC 10 | 0.02 |
15-11 | SL/SC 11 | 0.7 |
15-12 | SL/SC 12 | 6.9 |
15-13 | SL/SC 13 | 1.8 |
15-14 | SL/SC 14 | 8.54 |
15-15 | SL/SC 15 | 0.07 |
15-16 | SL/SC 16 | 0.9 |
实施例 | 载体上的配体/载体上的催化剂 | 3PN转化率 | 对5-甲酰戊腈的选择性 | 所生产的醛的直链度 | 还原产物(%) |
16-1 | SL/SC 2 | 76 | 83 | 95 | 12 |
16-2 | SL/SC 5 | 52 | 45 | 54 | 14 |
16-3 | SL/SC 6 | 29 | 40 | 20 | 20 |
16-4 | SL/SC 8 | 40 | 46 | 56 | 37 |
16-5 | SL/SC 9 | 28 | 4 | 8 | 37 |
16-6 | SL/SC 13 | 38 | 38 | 48 | 19 |
17-7 | SL/SC 15 | 10 | 27 | 52 | 25 |
Claims (26)
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US33336501P | 2001-11-26 | 2001-11-26 | |
US60/333,365 | 2001-11-26 |
Publications (2)
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CN1617892A true CN1617892A (zh) | 2005-05-18 |
CN1289539C CN1289539C (zh) | 2006-12-13 |
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CNB028275136A Expired - Fee Related CN1289539C (zh) | 2001-11-26 | 2002-11-26 | 载体上的双(磷)配体及其在催化中的应用 |
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US (1) | US6984604B2 (zh) |
EP (1) | EP1448620B1 (zh) |
JP (1) | JP4313674B2 (zh) |
KR (1) | KR100952265B1 (zh) |
CN (1) | CN1289539C (zh) |
AT (1) | ATE397627T1 (zh) |
AU (1) | AU2002365409A1 (zh) |
BR (1) | BR0215095A (zh) |
CA (1) | CA2468127A1 (zh) |
DE (1) | DE60226998D1 (zh) |
ES (1) | ES2307808T3 (zh) |
MX (1) | MXPA04004936A (zh) |
PL (1) | PL371465A1 (zh) |
WO (1) | WO2003046019A1 (zh) |
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Family Cites Families (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3391115A (en) * | 1962-04-27 | 1968-07-02 | Interchem Corp | Coating compositions containing phenol modified polydiene resinse and metal driers |
US3496215A (en) | 1965-11-23 | 1970-02-17 | Du Pont | Hydrocyanation of olefins using selected nickel phosphite catalysts |
FR2146806A5 (en) * | 1967-11-17 | 1973-03-02 | Reichhold Albert Chemie Ag | Unsatd resin prodn |
US3655723A (en) | 1969-10-31 | 1972-04-11 | Du Pont | Hydrocyanation of olefins |
US3631191A (en) | 1970-04-08 | 1971-12-28 | Du Pont | Synthesis of zero valent nickel-tetrakis triaryl phosphite complexes |
US3766237A (en) | 1972-01-25 | 1973-10-16 | Du Pont | Hydrocyanation of olefins |
JPS5034089A (zh) * | 1973-07-27 | 1975-04-02 | ||
JPS5034090A (zh) * | 1973-07-27 | 1975-04-02 | ||
DE2503867A1 (de) | 1974-02-01 | 1975-08-14 | Continental Oil Co | Alkyliertes butadienpolymerisat, verfahren zu seiner herstellung und seine verwendung |
JPS5194487A (ja) * | 1975-02-19 | 1976-08-19 | Denshikokanseisenjobutsuno seizohoho | |
DE4000625A1 (de) * | 1989-08-30 | 1991-03-07 | Bayer Ag | Verfahren zur herstellung von kautschuken |
DE59205529D1 (de) | 1991-01-25 | 1996-04-11 | Ciba Geigy Ag | Silangruppen enthaltende Diphosphine, immobilisierte Diophoshine und deren Verwendung als Hydrierkatalysatoren |
US5360938A (en) | 1991-08-21 | 1994-11-01 | Union Carbide Chemicals & Plastics Technology Corporation | Asymmetric syntheses |
DK0730574T3 (da) | 1993-11-23 | 1999-05-25 | Du Pont | Fremgangsmåder og katalysatorsammensætninger til hydrocyanering af monoolefiner |
US5512695A (en) | 1994-04-14 | 1996-04-30 | E. I. Du Pont De Nemours And Company | Bidentate phosphite and nickel catalyst compositions for hydrocyanation of monoolefins |
EP0755302B1 (en) * | 1994-04-14 | 2000-10-04 | E.I. Du Pont De Nemours And Company | Bidentate phosphite and nickel catalyst compositions for hydrocyanation of monoolefins |
US6156810A (en) * | 1996-08-01 | 2000-12-05 | Exxon Chemical Patents, Inc. | Solid nucleophilic reagent for conversion of benzylic halogen functionality on polymers to other functionalities |
JP3892932B2 (ja) * | 1997-03-11 | 2007-03-14 | 高砂香料工業株式会社 | ビニル基を有する光学活性ホスフィン誘導体、それをモノマーとするポリマー、及びそれらの遷移金属錯体 |
US6121184A (en) * | 1997-07-29 | 2000-09-19 | E. I. Du Pont De Nemours And Company | Supported bis(phosphorus) ligands |
US6229052B1 (en) * | 1998-05-29 | 2001-05-08 | E. I. Du Pont De Nemours And Company | Hydroformylation of olefins using supported bis(phosphorus) ligands |
US6307107B1 (en) * | 1999-09-20 | 2001-10-23 | E.I. Du Pont De Nemours And Company | Hydroformylation of acyclic monoethylenically unsaturated compounds to corresponding terminal aldehydes |
DE10002973A1 (de) * | 2000-01-24 | 2001-07-26 | Degussa | Polymere Diphosphinliganden für homogen lösliche Hydrierkatalysatoren, Verfahren zu deren Herstellung und Verwendung |
-
2002
- 2002-11-26 PL PL02371465A patent/PL371465A1/xx unknown
- 2002-11-26 CN CNB028275136A patent/CN1289539C/zh not_active Expired - Fee Related
- 2002-11-26 DE DE60226998T patent/DE60226998D1/de not_active Expired - Lifetime
- 2002-11-26 AT AT02791322T patent/ATE397627T1/de not_active IP Right Cessation
- 2002-11-26 WO PCT/US2002/037967 patent/WO2003046019A1/en active Application Filing
- 2002-11-26 JP JP2003547467A patent/JP4313674B2/ja not_active Expired - Fee Related
- 2002-11-26 ES ES02791322T patent/ES2307808T3/es not_active Expired - Lifetime
- 2002-11-26 MX MXPA04004936A patent/MXPA04004936A/es active IP Right Grant
- 2002-11-26 BR BR0215095-6A patent/BR0215095A/pt not_active Application Discontinuation
- 2002-11-26 KR KR1020047007957A patent/KR100952265B1/ko not_active IP Right Cessation
- 2002-11-26 AU AU2002365409A patent/AU2002365409A1/en not_active Abandoned
- 2002-11-26 EP EP02791322A patent/EP1448620B1/en not_active Expired - Lifetime
- 2002-11-26 US US10/305,230 patent/US6984604B2/en not_active Expired - Fee Related
- 2002-11-26 CA CA002468127A patent/CA2468127A1/en not_active Abandoned
Cited By (12)
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US8373001B2 (en) | 2003-02-10 | 2013-02-12 | Invista North America S.A R.L. | Method of producing dinitrile compounds |
US7897801B2 (en) | 2003-05-12 | 2011-03-01 | Invista North America S.A R.L. | Process for the preparation of dinitriles |
US7973174B2 (en) | 2005-10-18 | 2011-07-05 | Invista North America S.A.R.L. | Process of making 3-aminopentanenitrile |
US8178711B2 (en) | 2006-03-17 | 2012-05-15 | Invista North America S.A R.L. | Method for the purification of triorganophosphites by treatment with a basic additive |
US7919646B2 (en) | 2006-07-14 | 2011-04-05 | Invista North America S.A R.L. | Hydrocyanation of 2-pentenenitrile |
US8394981B2 (en) | 2006-07-14 | 2013-03-12 | Invista North America S.A R.L. | Hydrocyanation of 2-pentenenitrile |
US8101790B2 (en) | 2007-06-13 | 2012-01-24 | Invista North America S.A.R.L. | Process for improving adiponitrile quality |
US7977502B2 (en) | 2008-01-15 | 2011-07-12 | Invista North America S.A R.L. | Process for making and refining 3-pentenenitrile, and for refining 2-methyl-3-butenenitrile |
US8088943B2 (en) | 2008-01-15 | 2012-01-03 | Invista North America S.A R.L. | Hydrocyanation of pentenenitriles |
US8247621B2 (en) | 2008-10-14 | 2012-08-21 | Invista North America S.A.R.L. | Process for making 2-secondary-alkyl-4,5-di-(normal-alkyl)phenols |
US8338636B2 (en) | 2009-08-07 | 2012-12-25 | Invista North America S.A R.L. | Hydrogenation and esterification to form diesters |
CN107075090A (zh) * | 2014-12-18 | 2017-08-18 | 三菱瓦斯化学株式会社 | 氰酸酯化合物及其制造方法、树脂组合物以及固化物 |
Also Published As
Publication number | Publication date |
---|---|
KR20040054807A (ko) | 2004-06-25 |
BR0215095A (pt) | 2004-11-16 |
EP1448620B1 (en) | 2008-06-04 |
ES2307808T3 (es) | 2008-12-01 |
US6984604B2 (en) | 2006-01-10 |
AU2002365409A1 (en) | 2003-06-10 |
ATE397627T1 (de) | 2008-06-15 |
JP2005510588A (ja) | 2005-04-21 |
CA2468127A1 (en) | 2003-06-05 |
PL371465A1 (en) | 2005-06-13 |
US20030153691A1 (en) | 2003-08-14 |
CN1289539C (zh) | 2006-12-13 |
KR100952265B1 (ko) | 2010-04-09 |
EP1448620A1 (en) | 2004-08-25 |
JP4313674B2 (ja) | 2009-08-12 |
MXPA04004936A (es) | 2004-08-11 |
DE60226998D1 (de) | 2008-07-17 |
WO2003046019A1 (en) | 2003-06-05 |
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