JP4373786B2 - 高分子燐含有組成物ならびにヒドロシアン化反応、不飽和ニトリル異性化反応およびヒドロホルミル化反応における該組成物の使用 - Google Patents
高分子燐含有組成物ならびにヒドロシアン化反応、不飽和ニトリル異性化反応およびヒドロホルミル化反応における該組成物の使用 Download PDFInfo
- Publication number
- JP4373786B2 JP4373786B2 JP2003547046A JP2003547046A JP4373786B2 JP 4373786 B2 JP4373786 B2 JP 4373786B2 JP 2003547046 A JP2003547046 A JP 2003547046A JP 2003547046 A JP2003547046 A JP 2003547046A JP 4373786 B2 JP4373786 B2 JP 4373786B2
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- Japan
- Prior art keywords
- group
- phosphorus
- formula
- compound
- acryloyl
- Prior art date
- 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 - Lifetime
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- 239000000203 mixture Substances 0.000 title claims abstract description 233
- 229910052698 phosphorus Inorganic materials 0.000 title claims abstract description 96
- 239000011574 phosphorus Substances 0.000 title claims abstract description 79
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 75
- 238000007037 hydroformylation reaction Methods 0.000 title claims abstract description 40
- 238000005669 hydrocyanation reaction Methods 0.000 title abstract description 95
- 238000006317 isomerization reaction Methods 0.000 title abstract description 51
- 150000002825 nitriles Chemical class 0.000 title abstract description 35
- 239000003054 catalyst Substances 0.000 claims abstract description 143
- 229920000642 polymer Polymers 0.000 claims abstract description 68
- 229910052751 metal Inorganic materials 0.000 claims abstract description 58
- 239000002184 metal Substances 0.000 claims abstract description 58
- 239000003999 initiator Substances 0.000 claims abstract description 49
- 238000010438 heat treatment Methods 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims description 122
- 125000000217 alkyl group Chemical group 0.000 claims description 114
- 150000001875 compounds Chemical class 0.000 claims description 112
- 239000003446 ligand Substances 0.000 claims description 111
- -1 ketal Chemical group 0.000 claims description 98
- 229910052760 oxygen Inorganic materials 0.000 claims description 65
- 239000001301 oxygen Substances 0.000 claims description 65
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 65
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 62
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 61
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- DQTRYXANLKJLPK-UHFFFAOYSA-N chlorophosphonous acid Chemical compound OP(O)Cl DQTRYXANLKJLPK-UHFFFAOYSA-N 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 38
- 125000000962 organic group Chemical group 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 37
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 35
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims description 33
- 230000008569 process Effects 0.000 claims description 33
- 239000000460 chlorine Substances 0.000 claims description 30
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- 239000000178 monomer Substances 0.000 claims description 25
- 125000004104 aryloxy group Chemical group 0.000 claims description 22
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 21
- 150000002431 hydrogen Chemical group 0.000 claims description 21
- 150000002894 organic compounds Chemical class 0.000 claims description 21
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 150000004292 cyclic ethers Chemical class 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 18
- 150000002148 esters Chemical class 0.000 claims description 18
- 239000011737 fluorine Substances 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000001624 naphthyl group Chemical group 0.000 claims description 17
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 15
- 125000004437 phosphorous atom Chemical group 0.000 claims description 15
- 229910052723 transition metal Inorganic materials 0.000 claims description 15
- 150000003624 transition metals Chemical class 0.000 claims description 15
- 229910052783 alkali metal Inorganic materials 0.000 claims description 14
- 150000001340 alkali metals Chemical class 0.000 claims description 14
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 14
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 14
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 claims description 12
- ZDTQJPVEXIUREJ-UHFFFAOYSA-N dichlorophosphinous acid Chemical compound OP(Cl)Cl ZDTQJPVEXIUREJ-UHFFFAOYSA-N 0.000 claims description 12
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 11
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 10
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 9
- 125000001118 alkylidene group Chemical group 0.000 claims description 9
- 150000003335 secondary amines Chemical class 0.000 claims description 9
- 150000003457 sulfones Chemical class 0.000 claims description 9
- 150000003462 sulfoxides Chemical class 0.000 claims description 9
- 150000003512 tertiary amines Chemical class 0.000 claims description 9
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 8
- 150000005846 sugar alcohols Polymers 0.000 claims description 8
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 claims description 5
- OBSZRRSYVTXPNB-UHFFFAOYSA-N tetraphosphorus Chemical compound P12P3P1P32 OBSZRRSYVTXPNB-UHFFFAOYSA-N 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 abstract description 30
- PPTXVXKCQZKFBN-UHFFFAOYSA-N (S)-(-)-1,1'-Bi-2-naphthol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 PPTXVXKCQZKFBN-UHFFFAOYSA-N 0.000 abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 156
- CFEYBLWMNFZOPB-UHFFFAOYSA-N Allylacetonitrile Natural products C=CCCC#N CFEYBLWMNFZOPB-UHFFFAOYSA-N 0.000 description 131
- UVKXJAUUKPDDNW-NSCUHMNNSA-N (e)-pent-3-enenitrile Chemical compound C\C=C\CC#N UVKXJAUUKPDDNW-NSCUHMNNSA-N 0.000 description 117
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 111
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 110
- WBAXCOMEMKANRN-UHFFFAOYSA-N 2-methylbut-3-enenitrile Chemical compound C=CC(C)C#N WBAXCOMEMKANRN-UHFFFAOYSA-N 0.000 description 86
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 77
- 239000007787 solid Substances 0.000 description 67
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 66
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 66
- 238000006243 chemical reaction Methods 0.000 description 61
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 60
- 239000000243 solution Substances 0.000 description 57
- 238000004817 gas chromatography Methods 0.000 description 55
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 55
- 239000002904 solvent Substances 0.000 description 43
- 239000000047 product Substances 0.000 description 41
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 33
- 238000002360 preparation method Methods 0.000 description 33
- RFFFKMOABOFIDF-UHFFFAOYSA-N Pentanenitrile Chemical compound CCCCC#N RFFFKMOABOFIDF-UHFFFAOYSA-N 0.000 description 32
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 29
- 238000006116 polymerization reaction Methods 0.000 description 24
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 22
- 239000010948 rhodium Substances 0.000 description 22
- ISBHMJZRKAFTGE-UHFFFAOYSA-N pent-2-enenitrile Chemical compound CCC=CC#N ISBHMJZRKAFTGE-UHFFFAOYSA-N 0.000 description 20
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 20
- 238000003756 stirring Methods 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical group COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 17
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 16
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 15
- 239000002841 Lewis acid Substances 0.000 description 14
- 150000007517 lewis acids Chemical class 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 13
- 125000005538 phosphinite group Chemical group 0.000 description 13
- 238000005954 phosphonylation reaction Methods 0.000 description 13
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalene Chemical group C1=CC=C2C(C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 12
- 239000002585 base Substances 0.000 description 12
- 239000007789 gas Substances 0.000 description 12
- 238000002156 mixing Methods 0.000 description 12
- 229910052759 nickel Inorganic materials 0.000 description 12
- 150000002978 peroxides Chemical class 0.000 description 12
- 239000002002 slurry Substances 0.000 description 12
- 239000003921 oil Substances 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 10
- 229910052786 argon Inorganic materials 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- 229930195733 hydrocarbon Natural products 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 150000001299 aldehydes Chemical class 0.000 description 9
- 150000001336 alkenes Chemical class 0.000 description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
- 150000002009 diols Chemical class 0.000 description 9
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 9
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 9
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 8
- 239000012530 fluid Substances 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 8
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 125000006239 protecting group Chemical group 0.000 description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000000921 elemental analysis Methods 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 150000002816 nickel compounds Chemical class 0.000 description 7
- 150000002989 phenols Chemical class 0.000 description 7
- 229910052703 rhodium Inorganic materials 0.000 description 7
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 7
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 6
- 238000007334 copolymerization reaction Methods 0.000 description 6
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 6
- 150000003983 crown ethers Chemical class 0.000 description 6
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 6
- 125000004386 diacrylate group Chemical group 0.000 description 6
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 150000002736 metal compounds Chemical class 0.000 description 6
- 150000007530 organic bases Chemical class 0.000 description 6
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 125000005270 trialkylamine group Chemical group 0.000 description 6
- IDVNIUHJAYIFCZ-UHFFFAOYSA-N 6-ethenyl-1-(6-ethenyl-2-hydroxynaphthalen-1-yl)naphthalen-2-ol Chemical group C=CC1=CC=C2C(C3=C4C=CC(C=C)=CC4=CC=C3O)=C(O)C=CC2=C1 IDVNIUHJAYIFCZ-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 5
- 125000005243 carbonyl alkyl group Chemical group 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 229910017052 cobalt Inorganic materials 0.000 description 5
- 239000010941 cobalt Substances 0.000 description 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 150000003017 phosphorus Chemical class 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 239000003039 volatile agent Substances 0.000 description 5
- WUCQRXWCJPCWTQ-NSCUHMNNSA-N (e)-pent-3-enal Chemical compound C\C=C\CC=O WUCQRXWCJPCWTQ-NSCUHMNNSA-N 0.000 description 4
- ROLXEZSIIQQWRL-UHFFFAOYSA-N 6-oxohexanenitrile Chemical compound O=CCCCCC#N ROLXEZSIIQQWRL-UHFFFAOYSA-N 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- WUCQRXWCJPCWTQ-UHFFFAOYSA-N trans-3-pentenal Natural products CC=CCC=O WUCQRXWCJPCWTQ-UHFFFAOYSA-N 0.000 description 4
- UIUWNILCHFBLEQ-NSCUHMNNSA-N trans-pent-3-enoic acid Chemical compound C\C=C\CC(O)=O UIUWNILCHFBLEQ-NSCUHMNNSA-N 0.000 description 4
- 239000011592 zinc chloride Substances 0.000 description 4
- 235000005074 zinc chloride Nutrition 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 3
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
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- BKHZQJRTFNFCTG-UHFFFAOYSA-N tris(2-methylphenyl) phosphite Chemical compound CC1=CC=CC=C1OP(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C BKHZQJRTFNFCTG-UHFFFAOYSA-N 0.000 description 1
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- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
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- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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- B01J31/30—Halides
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- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/08—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds
- C07C253/10—Preparation of carboxylic acid nitriles by addition of hydrogen cyanide or salts thereof to unsaturated compounds to compounds containing carbon-to-carbon double bonds
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- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
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- 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
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- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
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- 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
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- C07F15/0066—Palladium compounds without a metal-carbon linkage
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| PCT/US2002/037304 WO2003045552A2 (en) | 2001-11-26 | 2002-11-20 | Polymeric phosphorus-containing compositions and their use in hydrocyanation, unsaturated nitrile isomerization and hydroformylation reactions |
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| JP2009017149A Expired - Lifetime JP5265400B2 (ja) | 2001-11-26 | 2009-01-28 | 高分子燐含有組成物ならびにヒドロシアン化反応、不飽和ニトリル異性化反応およびヒドロホルミル化反応における該組成物の使用 |
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| US6936171B2 (en) * | 2003-01-08 | 2005-08-30 | Invista North America S.A.R.L. | Process for catalyst recovery from hydrocyanation product mixtures |
| FR2850966B1 (fr) | 2003-02-10 | 2005-03-18 | Rhodia Polyamide Intermediates | Procede de fabrication de composes dinitriles |
| US6844289B2 (en) * | 2003-04-08 | 2005-01-18 | Invista North America S.A.R.L. | Process for the preparation of a nickel/phosphorous ligand catalyst |
| FR2854891B1 (fr) | 2003-05-12 | 2006-07-07 | Rhodia Polyamide Intermediates | Procede de preparation de dinitriles |
| FR2854892B1 (fr) | 2003-05-12 | 2005-06-24 | Rhodia Polyamide Intermediates | Procede de fabrication de dinitriles |
| DE10350999A1 (de) * | 2003-10-30 | 2005-06-02 | Basf Ag | Katalysator, umfassend wenigstens einen Nickel(O)Komplex stabilisiert durch einen sterisch anspruchsvollen Chelatphosphinitphosphitliganden, sowie ein Verfahren zur Herstellung von Nitrilen |
| JP4576584B2 (ja) * | 2005-01-31 | 2010-11-10 | 独立行政法人科学技術振興機構 | リン含有高分子固定化パラジウム触媒およびその使用 |
| CZ2008547A3 (cs) | 2006-03-17 | 2009-06-10 | Invista Technologies S. A. R. L. | Zpusob purifikace triorganofosfitu ošetrením bazickým aditivem |
| US7709674B2 (en) | 2006-07-14 | 2010-05-04 | Invista North America S.A R.L | Hydrocyanation process with reduced yield losses |
| US7880028B2 (en) | 2006-07-14 | 2011-02-01 | Invista North America S.A R.L. | Process for making 3-pentenenitrile by hydrocyanation of butadiene |
| EP2045014B8 (en) | 2006-07-25 | 2014-02-26 | National University Corporation Hokkaido University | Polymer-supported metal complex catalyst |
| DE102007031547A1 (de) * | 2007-07-06 | 2009-01-15 | Deutsches Zentrum für Luft- und Raumfahrt e.V. | Robuster kapazitiver Abstandssensor |
| EP2229354B1 (en) | 2008-01-15 | 2013-03-20 | Invista Technologies S.à.r.l. | Process for making and refining 3-pentenenitrile, and for refining 2-methyl-3-butenenitrile |
| EP2229353B1 (en) | 2008-01-15 | 2018-01-03 | INVISTA Textiles (U.K.) Limited | Hydrocyanation of pentenenitriles |
| WO2010123743A1 (en) * | 2009-04-21 | 2010-10-28 | Invista Technologies S.A R.L. | Highly selective process for producing organodiphosphites |
| DK2658651T3 (en) | 2009-12-18 | 2019-01-14 | Invista Textiles Uk Ltd | NICKEL COMPOSITIONS FOR THE MANUFACTURE OF NICKEL METAL AND NICKEL COMPLEXS |
| CN103080119B (zh) | 2010-09-07 | 2015-04-08 | 因温斯特技术公司 | 用于制备镍金属的镍组合物和镍配合物 |
| JP2014522408A (ja) * | 2011-06-10 | 2014-09-04 | インヴィスタ テクノロジーズ エスアエルエル | 金属−配位子触媒形成の改善 |
| US8822577B2 (en) | 2011-11-21 | 2014-09-02 | Bridgestone Sports Co., Ltd. | Rubber composition for golf ball |
| KR20140127220A (ko) | 2011-12-21 | 2014-11-03 | 인비스타 테크놀러지스 에스.에이 알.엘. | 안정한 에멀젼을 감소시키기 위한 추출 용매 제어 |
| CN103547349B (zh) | 2011-12-21 | 2016-03-16 | 因温斯特北美公司 | 用于减少稳定乳液的萃取溶剂控制 |
| US9133223B2 (en) | 2011-12-21 | 2015-09-15 | Invista North America S.A.R.L. | Extraction solvent control for reducing stable emulsions |
| US9676800B2 (en) | 2013-06-20 | 2017-06-13 | Invista North America S.A.R.L. | Extraction solvent control for reducing stable emulsions |
| CN105307741B (zh) | 2013-06-20 | 2019-06-18 | 英威达纺织(英国)有限公司 | 用于减少稳定乳液的萃取溶剂控制 |
| CN105377395B (zh) | 2013-06-20 | 2018-05-29 | 英威达纺织(英国)有限公司 | 用于减少稳定乳液的萃取溶剂控制 |
| EP3010617B1 (en) | 2013-06-20 | 2022-11-30 | INVISTA Textiles (U.K.) Limited | Extraction solvent control for reducing stable emulsions |
| WO2015200630A1 (en) | 2014-06-27 | 2015-12-30 | Invista North America S.A R.L. | Integrated process for nitrile manufacture with enhanced liquid-liquid extraction |
| WO2015200597A1 (en) | 2014-06-27 | 2015-12-30 | Invista North America S.A R.L. | Enhanced extraction of impurities from mixture comprising nitriles |
| CN106140303B (zh) * | 2015-04-03 | 2018-11-27 | 中国科学院大连化学物理研究所 | 一种含膦有机混聚物-金属多相催化剂及其制备和应用 |
| CN106140302B (zh) * | 2015-04-03 | 2018-11-27 | 中国科学院大连化学物理研究所 | 一种含膦有机混聚物-金属多相催化剂及其方法和应用 |
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| CN112480169A (zh) * | 2020-12-07 | 2021-03-12 | 南雄志一精细化工有限公司 | 一种液体含磷化合物及其应用和制备方法 |
| CN115873221B (zh) * | 2021-12-17 | 2024-06-04 | 浙江新和成股份有限公司 | 一种含磷聚合物及其制备方法和应用 |
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| AU2002216719A1 (en) * | 2000-11-17 | 2002-05-27 | The Penn State Research Foundation | Ortho substituted chiral phosphines and phosphinites and their use in asymmetriccatayltic reactions |
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Also Published As
| Publication number | Publication date |
|---|---|
| BR0214629B1 (pt) | 2012-08-21 |
| AU2002348313A1 (en) | 2003-06-10 |
| EP1905511A3 (en) | 2010-01-27 |
| PL370988A1 (en) | 2005-06-13 |
| MXPA04004938A (es) | 2004-08-11 |
| EP1448298B1 (en) | 2010-09-22 |
| KR20040058321A (ko) | 2004-07-03 |
| US6660876B2 (en) | 2003-12-09 |
| ATE482028T1 (de) | 2010-10-15 |
| US20030144440A1 (en) | 2003-07-31 |
| EP1448298A2 (en) | 2004-08-25 |
| JP5265400B2 (ja) | 2013-08-14 |
| CA2468195A1 (en) | 2003-06-05 |
| EP2277623A3 (en) | 2011-06-08 |
| CN1617764A (zh) | 2005-05-18 |
| EP1905511A2 (en) | 2008-04-02 |
| BR0214629A (pt) | 2004-11-03 |
| WO2003045552A2 (en) | 2003-06-05 |
| DE60237781D1 (de) | 2010-11-04 |
| US20040054105A1 (en) | 2004-03-18 |
| EP2277623A2 (en) | 2011-01-26 |
| JP2009161760A (ja) | 2009-07-23 |
| CN100345635C (zh) | 2007-10-31 |
| WO2003045552A3 (en) | 2003-10-30 |
| JP2005510547A (ja) | 2005-04-21 |
| AU2002348313A8 (en) | 2003-06-10 |
| EP1905511B1 (en) | 2013-03-27 |
| US6924345B2 (en) | 2005-08-02 |
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