CN1847288B - 聚合亚磷酸酯组合物和不饱和有机化合物的氢氰化以及不饱和腈的异构化 - Google Patents
聚合亚磷酸酯组合物和不饱和有机化合物的氢氰化以及不饱和腈的异构化 Download PDFInfo
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- CN1847288B CN1847288B CN2006100819210A CN200610081921A CN1847288B CN 1847288 B CN1847288 B CN 1847288B CN 2006100819210 A CN2006100819210 A CN 2006100819210A CN 200610081921 A CN200610081921 A CN 200610081921A CN 1847288 B CN1847288 B CN 1847288B
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- 238000006317 isomerization reaction Methods 0.000 title claims abstract description 31
- 150000002825 nitriles Chemical class 0.000 title claims abstract description 24
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 title claims description 20
- 238000005669 hydrocyanation reaction Methods 0.000 title abstract description 38
- 150000002894 organic compounds Chemical class 0.000 title abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 97
- -1 aromatic diol Chemical class 0.000 claims abstract description 87
- 239000003054 catalyst Substances 0.000 claims abstract description 80
- 229920000642 polymer Polymers 0.000 claims abstract description 53
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims abstract description 22
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- 239000002184 metal Substances 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 12
- 239000002841 Lewis acid Substances 0.000 claims abstract description 10
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims abstract description 10
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 55
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 54
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 46
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 41
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 27
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 25
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- 229910052801 chlorine Inorganic materials 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 150000007530 organic bases Chemical class 0.000 claims description 17
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 13
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- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 7
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- IBNFPRMKLZDANU-UHFFFAOYSA-N 4-(4-hydroxy-3-methylphenyl)sulfanyl-2-methylphenol Chemical compound C1=C(O)C(C)=CC(SC=2C=C(C)C(O)=CC=2)=C1 IBNFPRMKLZDANU-UHFFFAOYSA-N 0.000 claims description 3
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- RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims description 2
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 229910052793 cadmium Inorganic materials 0.000 claims description 2
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- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 2
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 239000011733 molybdenum Substances 0.000 claims description 2
- 229910052758 niobium Inorganic materials 0.000 claims description 2
- 239000010955 niobium Substances 0.000 claims description 2
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052702 rhenium Inorganic materials 0.000 claims description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052706 scandium Inorganic materials 0.000 claims description 2
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical group [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims description 2
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- 239000011701 zinc Substances 0.000 claims description 2
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- 239000000126 substance Substances 0.000 claims 9
- QPVRKFOKCKORDP-UHFFFAOYSA-N 1,3-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC(C)(O)CC=C1 QPVRKFOKCKORDP-UHFFFAOYSA-N 0.000 claims 6
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 claims 6
- 125000001188 haloalkyl group Chemical group 0.000 claims 6
- 150000004702 methyl esters Chemical class 0.000 claims 3
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 claims 2
- LDQYTDPXIMNESL-UHFFFAOYSA-N 2-methyl-4-propylphenol Chemical compound CCCC1=CC=C(O)C(C)=C1 LDQYTDPXIMNESL-UHFFFAOYSA-N 0.000 claims 2
- NGFPWHGISWUQOI-UHFFFAOYSA-N 2-sec-butylphenol Chemical compound CCC(C)C1=CC=CC=C1O NGFPWHGISWUQOI-UHFFFAOYSA-N 0.000 claims 2
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- 229910052500 inorganic mineral Inorganic materials 0.000 claims 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 239000004411 aluminium Substances 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
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- 238000006243 chemical reaction Methods 0.000 abstract description 27
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- DQTRYXANLKJLPK-UHFFFAOYSA-N chlorophosphonous acid Chemical compound OP(O)Cl DQTRYXANLKJLPK-UHFFFAOYSA-N 0.000 abstract description 19
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- 125000001033 ether group Chemical group 0.000 description 1
- WCHFOOKTKZYYAE-UHFFFAOYSA-N ethoxyperoxyethane Chemical compound CCOOOCC WCHFOOKTKZYYAE-UHFFFAOYSA-N 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- IIRDTKBZINWQAW-UHFFFAOYSA-N hexaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCO IIRDTKBZINWQAW-UHFFFAOYSA-N 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- KJALUUCEMMPKAC-ONEGZZNKSA-N methyl (e)-pent-3-enoate Chemical compound COC(=O)C\C=C\C KJALUUCEMMPKAC-ONEGZZNKSA-N 0.000 description 1
- SCOGIYZPQMECLW-UHFFFAOYSA-N methyl 3-hydroxy-4-(2-hydroxy-3-methoxycarbonylnaphthalen-1-yl)naphthalene-2-carboxylate Chemical compound C1=CC=C2C(C=3C4=CC=CC=C4C=C(C=3O)C(=O)OC)=C(O)C(C(=O)OC)=CC2=C1 SCOGIYZPQMECLW-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- MBAHGFJTIVZLFB-UHFFFAOYSA-N methyl pent-2-enoate Chemical compound CCC=CC(=O)OC MBAHGFJTIVZLFB-UHFFFAOYSA-N 0.000 description 1
- KJALUUCEMMPKAC-UHFFFAOYSA-N methyl pent-3-enoate Chemical compound COC(=O)CC=CC KJALUUCEMMPKAC-UHFFFAOYSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- MDKQJOKKKZNQDG-UHFFFAOYSA-N n,n'-dimethylhexane-1,6-diamine Chemical compound CNCCCCCCNC MDKQJOKKKZNQDG-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- IETUUPFUMFSAAO-UHFFFAOYSA-N pent-1-ene prop-2-enoic acid Chemical compound C(C=C)(=O)O.C=CCCC IETUUPFUMFSAAO-UHFFFAOYSA-N 0.000 description 1
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229930015698 phenylpropene Natural products 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical group OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- SXADIBFZNXBEGI-UHFFFAOYSA-N phosphoramidous acid Chemical compound NP(O)O SXADIBFZNXBEGI-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000005266 side chain polymer Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
- C08G79/04—Phosphorus linked to oxygen or to oxygen and carbon
-
- 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
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
-
- 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
- B01J31/165—Polymer immobilised coordination complexes, e.g. organometallic complexes
- B01J31/1658—Polymer immobilised coordination complexes, e.g. organometallic complexes immobilised by covalent linkages, i.e. pendant complexes with optional linking groups, e.g. on Wang or Merrifield resins
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/692—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus
- C08G63/6924—Polyesters containing atoms other than carbon, hydrogen and oxygen containing phosphorus derived from polycarboxylic acids and polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/42—Polyamides containing atoms other than carbon, hydrogen, oxygen, and nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/48—Polymers modified by chemical after-treatment
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- 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
- B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
-
- 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
- B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
- B01J2231/52—Isomerisation reactions
-
- 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
- B01J2531/824—Palladium
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- 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
- B01J2531/84—Metals of the iron group
- B01J2531/845—Cobalt
-
- 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
- B01J2531/84—Metals of the iron group
- B01J2531/847—Nickel
-
- 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
-
- 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
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyurethanes Or Polyureas (AREA)
- Polyamides (AREA)
- Polyesters Or Polycarbonates (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/399,261 US6284865B1 (en) | 1999-09-20 | 1999-09-20 | Polymeric phosphite composition and hydrocyanation of unsaturated organic compounds and the isomerization of unsaturated nitriles |
| US09/399261 | 1999-09-20 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB008156573A Division CN1279088C (zh) | 1999-09-20 | 2000-09-19 | 聚合亚磷酸酯组合物和不饱和有机化合物的氢氰化以及不饱和腈的异构化 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1847288A CN1847288A (zh) | 2006-10-18 |
| CN1847288B true CN1847288B (zh) | 2011-06-15 |
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ID=23578850
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|---|---|---|---|
| CN2006100819210A Expired - Lifetime CN1847288B (zh) | 1999-09-20 | 2000-09-19 | 聚合亚磷酸酯组合物和不饱和有机化合物的氢氰化以及不饱和腈的异构化 |
| CNB008156573A Expired - Lifetime CN1279088C (zh) | 1999-09-20 | 2000-09-19 | 聚合亚磷酸酯组合物和不饱和有机化合物的氢氰化以及不饱和腈的异构化 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
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| CNB008156573A Expired - Lifetime CN1279088C (zh) | 1999-09-20 | 2000-09-19 | 聚合亚磷酸酯组合物和不饱和有机化合物的氢氰化以及不饱和腈的异构化 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US6284865B1 (enExample) |
| EP (1) | EP1216268B1 (enExample) |
| JP (1) | JP2003510385A (enExample) |
| CN (2) | CN1847288B (enExample) |
| BR (1) | BR0014478B1 (enExample) |
| CA (1) | CA2384408A1 (enExample) |
| DE (1) | DE60006562T2 (enExample) |
| HK (1) | HK1052364B (enExample) |
| MY (1) | MY126778A (enExample) |
| TW (1) | TWI226345B (enExample) |
| WO (1) | WO2001021684A1 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6420611B1 (en) * | 1999-09-20 | 2002-07-16 | E. I. Du Pont De Nemours And Company | Composition comprising polymeric phosphite |
| US6660876B2 (en) * | 2001-11-26 | 2003-12-09 | E. I. Du Pont De Nemours And Company | Phosphorus-containing compositions and their use in hydrocyanation, isomerization and hydroformylation reactions |
| US20030135014A1 (en) * | 2001-11-26 | 2003-07-17 | Radu Nora S. | Polymeric, phosphorus-containing compositions and their use in hydrocyanation, isomerization and hydroformylation reactions |
| US7179932B2 (en) * | 2002-06-03 | 2007-02-20 | Genencor International, Inc. | Synthesis of cis-diols from aryl silanes |
| FR2849027B1 (fr) * | 2002-12-23 | 2005-01-21 | Rhodia Polyamide Intermediates | Procede de synthese de composes comprenant des fonctions nitriles a partir de composes a insaturations ethyleniques |
| US6897329B2 (en) * | 2003-01-14 | 2005-05-24 | Invista North America S.A.R.L. | Process for the preparation of nickel/phosphorous ligand catalyst for olefin hydrocyanation |
| FR2850966B1 (fr) | 2003-02-10 | 2005-03-18 | Rhodia Polyamide Intermediates | Procede de fabrication de composes dinitriles |
| FR2854892B1 (fr) | 2003-05-12 | 2005-06-24 | Rhodia Polyamide Intermediates | Procede de fabrication de dinitriles |
| FR2854891B1 (fr) | 2003-05-12 | 2006-07-07 | Rhodia Polyamide Intermediates | Procede de preparation de dinitriles |
| EP2322503B1 (en) | 2005-10-18 | 2014-12-31 | Invista Technologies S.à.r.l. | Process of making 3-aminopentanenitrile |
| CZ2008547A3 (cs) | 2006-03-17 | 2009-06-10 | Invista Technologies S. A. R. L. | Zpusob purifikace triorganofosfitu ošetrením bazickým aditivem |
| US7919646B2 (en) | 2006-07-14 | 2011-04-05 | Invista North America S.A R.L. | Hydrocyanation of 2-pentenenitrile |
| 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 |
| US7659422B2 (en) * | 2006-07-14 | 2010-02-09 | Invista North America S.A.R.L. | Hydrocyanation process with reduced yield losses |
| WO2008075639A1 (ja) * | 2006-12-20 | 2008-06-26 | Mitsubishi Gas Chemical Company, Inc. | プレフィルドシリンジ |
| US8906334B2 (en) | 2007-05-14 | 2014-12-09 | Invista North America S.A R.L. | High efficiency reactor and process |
| EP2164587B1 (en) | 2007-06-13 | 2018-04-04 | INVISTA Textiles (U.K.) Limited | Process for improving adiponitrile quality |
| EP2229353B1 (en) | 2008-01-15 | 2018-01-03 | INVISTA Textiles (U.K.) Limited | Hydrocyanation of pentenenitriles |
| 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 |
| JP2011515411A (ja) * | 2008-03-19 | 2011-05-19 | インビスタ テクノロジーズ エス エイ アール エル | シクロドデカトリエンの製造方法およびラウロラクトンの製造方法 |
| WO2010045131A1 (en) | 2008-10-14 | 2010-04-22 | Invista Technologies 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 |
| 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 |
| US10221260B2 (en) | 2016-07-29 | 2019-03-05 | Exxonmobil Chemical Patents Inc. | Phenolate transition metal complexes, production and use thereof |
| CN109476683B (zh) * | 2016-07-29 | 2022-07-22 | 埃克森美孚化学专利公司 | 酚基过渡金属络合物，其生产和用途 |
| JP7125329B2 (ja) * | 2018-11-06 | 2022-08-24 | 大阪ガスケミカル株式会社 | ビナフチル骨格を有するポリエステル樹脂並びにその製造方法及び用途 |
| JP7656439B2 (ja) * | 2020-02-21 | 2025-04-03 | 大阪ガスケミカル株式会社 | ビナフチル骨格を有する熱可塑性樹脂ならびにその製造方法および用途 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1159799A (zh) * | 1994-10-07 | 1997-09-17 | 纳幕尔杜邦公司 | 氢氰化方法及所用多配位亚磷酸酯和镍催化剂复合物 |
| US5710306A (en) * | 1996-03-15 | 1998-01-20 | Dsm N.V. | Process to prepare a multidentate phosphite compound |
| WO1999006355A1 (en) * | 1997-07-29 | 1999-02-11 | E.I. Du Pont De Nemours And Company | Hydrocyanation of diolefins and isomerization of nonconjugated 2-alkyl-3-monoalkenenitriles |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3496215A (en) | 1965-11-23 | 1970-02-17 | Du Pont | Hydrocyanation of olefins using selected nickel phosphite catalysts |
| 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 |
| JPS5356239A (en) * | 1976-11-01 | 1978-05-22 | Adeka Argus Chem Co Ltd | Stbilized synthetic resin compositions |
| JPS54139953A (en) * | 1978-04-24 | 1979-10-30 | Adeka Argus Chem Co Ltd | Stabilized synthetic resin composition |
| SG43803A1 (en) | 1991-01-25 | 1997-11-14 | Ciba Geigy Ag | Diphosphines containing silane groups immobilised diphosphines and the use thereof as hydrogenation catalyst |
| US5360938A (en) | 1991-08-21 | 1994-11-01 | Union Carbide Chemicals & Plastics Technology Corporation | Asymmetric syntheses |
| WO1995014659A1 (en) | 1993-11-23 | 1995-06-01 | E.I. Du Pont De Nemours And Company | Processes and catalyst compositions for hydrocyanation of monoolefins |
| US5543536A (en) | 1994-04-26 | 1996-08-06 | E. I. Du Pont De Nemours And Company | Monodentate phosphite and nickel catalyst composition for monoolefin hydrocyanation |
| US5512696A (en) | 1995-07-21 | 1996-04-30 | E. I. Du Pont De Nemours And Company | Hydrocyanation process and multidentate phosphite and nickel catalyst composition therefor |
| US5573641A (en) | 1995-04-28 | 1996-11-12 | Nalco Chemical Company | Method for preventing microbial deposits in the wet end of papermachines using ethylene oxide/propylene oxide copolymer |
| US5874641A (en) * | 1996-03-15 | 1999-02-23 | Dsm N.V. | Process to prepare a terminal aldehyde |
| US6420611B1 (en) * | 1999-09-20 | 2002-07-16 | E. I. Du Pont De Nemours And Company | Composition comprising polymeric phosphite |
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1999
- 1999-09-20 US US09/399,261 patent/US6284865B1/en not_active Expired - Fee Related
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2000
- 2000-09-19 CA CA002384408A patent/CA2384408A1/en not_active Abandoned
- 2000-09-19 CN CN2006100819210A patent/CN1847288B/zh not_active Expired - Lifetime
- 2000-09-19 BR BRPI0014478-9A patent/BR0014478B1/pt not_active IP Right Cessation
- 2000-09-19 EP EP00963590A patent/EP1216268B1/en not_active Expired - Lifetime
- 2000-09-19 HK HK03104699.3A patent/HK1052364B/zh not_active IP Right Cessation
- 2000-09-19 DE DE60006562T patent/DE60006562T2/de not_active Expired - Lifetime
- 2000-09-19 JP JP2001525254A patent/JP2003510385A/ja active Pending
- 2000-09-19 CN CNB008156573A patent/CN1279088C/zh not_active Expired - Lifetime
- 2000-09-19 WO PCT/US2000/025568 patent/WO2001021684A1/en not_active Ceased
- 2000-09-20 MY MYPI20004390 patent/MY126778A/en unknown
- 2000-09-20 TW TW089119359A patent/TWI226345B/zh not_active IP Right Cessation
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1159799A (zh) * | 1994-10-07 | 1997-09-17 | 纳幕尔杜邦公司 | 氢氰化方法及所用多配位亚磷酸酯和镍催化剂复合物 |
| US5710306A (en) * | 1996-03-15 | 1998-01-20 | Dsm N.V. | Process to prepare a multidentate phosphite compound |
| WO1999006355A1 (en) * | 1997-07-29 | 1999-02-11 | E.I. Du Pont De Nemours And Company | Hydrocyanation of diolefins and isomerization of nonconjugated 2-alkyl-3-monoalkenenitriles |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1279088C (zh) | 2006-10-11 |
| US6855799B2 (en) | 2005-02-15 |
| EP1216268B1 (en) | 2003-11-12 |
| BR0014478B1 (pt) | 2010-11-30 |
| MY126778A (en) | 2006-10-31 |
| CN1847288A (zh) | 2006-10-18 |
| EP1216268A1 (en) | 2002-06-26 |
| HK1052364B (zh) | 2007-05-11 |
| WO2001021684A1 (en) | 2001-03-29 |
| DE60006562T2 (de) | 2004-09-16 |
| BR0014478A (pt) | 2002-06-18 |
| JP2003510385A (ja) | 2003-03-18 |
| HK1052364A1 (en) | 2003-09-11 |
| CA2384408A1 (en) | 2001-03-29 |
| TWI226345B (en) | 2005-01-11 |
| CN1390241A (zh) | 2003-01-08 |
| DE60006562D1 (de) | 2003-12-18 |
| US20010049431A1 (en) | 2001-12-06 |
| US6284865B1 (en) | 2001-09-04 |
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