CA1314053C - Process for purifying tertiary organophosphites - Google Patents
Process for purifying tertiary organophosphitesInfo
- Publication number
- CA1314053C CA1314053C CA000562929A CA562929A CA1314053C CA 1314053 C CA1314053 C CA 1314053C CA 000562929 A CA000562929 A CA 000562929A CA 562929 A CA562929 A CA 562929A CA 1314053 C CA1314053 C CA 1314053C
- Authority
- CA
- Canada
- Prior art keywords
- organophosphite
- phosphite
- tertiary
- lewis base
- employed
- 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 - Fee Related
Links
- 150000008301 phosphite esters Chemical group 0.000 title claims abstract description 214
- 238000000034 method Methods 0.000 title claims abstract description 75
- 230000008569 process Effects 0.000 title claims abstract description 64
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 121
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 117
- -1 organophosphite salt Chemical class 0.000 claims description 111
- 239000000203 mixture Substances 0.000 claims description 95
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 95
- 150000007527 lewis bases Chemical class 0.000 claims description 74
- 239000002879 Lewis base Substances 0.000 claims description 72
- 238000006243 chemical reaction Methods 0.000 claims description 46
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims description 38
- 238000007037 hydroformylation reaction Methods 0.000 claims description 30
- 238000010992 reflux Methods 0.000 claims description 29
- 229910052703 rhodium Inorganic materials 0.000 claims description 29
- 239000010948 rhodium Substances 0.000 claims description 29
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 27
- 238000011282 treatment Methods 0.000 claims description 21
- 239000007787 solid Substances 0.000 claims description 20
- 239000011347 resin Substances 0.000 claims description 19
- 229920005989 resin Polymers 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 18
- 239000003960 organic solvent Substances 0.000 claims description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 13
- 239000002585 base Substances 0.000 claims description 10
- 239000006227 byproduct Substances 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- 238000001914 filtration Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 150000003512 tertiary amines Chemical class 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 6
- 230000005494 condensation Effects 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 5
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical group [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 claims 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 175
- 238000005481 NMR spectroscopy Methods 0.000 description 89
- 239000000243 solution Substances 0.000 description 66
- 150000003254 radicals Chemical class 0.000 description 42
- 239000003921 oil Substances 0.000 description 37
- 239000013078 crystal Substances 0.000 description 22
- 150000001299 aldehydes Chemical class 0.000 description 21
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 238000002474 experimental method Methods 0.000 description 16
- 239000004215 Carbon black (E152) Substances 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 14
- 229930195733 hydrocarbon Natural products 0.000 description 14
- JHQYNYXQKSKNAK-UHFFFAOYSA-N OP(O)O.OP(O)O Chemical compound OP(O)O.OP(O)O JHQYNYXQKSKNAK-UHFFFAOYSA-N 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 239000003446 ligand Substances 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- KUMNEOGIHFCNQW-UHFFFAOYSA-N diphenyl phosphite Chemical compound C=1C=CC=CC=1OP([O-])OC1=CC=CC=C1 KUMNEOGIHFCNQW-UHFFFAOYSA-N 0.000 description 9
- 125000004430 oxygen atom Chemical group O* 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 125000004437 phosphorous atom Chemical group 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 150000005840 aryl radicals Chemical class 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 6
- 230000002411 adverse Effects 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 230000001419 dependent effect Effects 0.000 description 5
- 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 5
- 150000002431 hydrogen Chemical group 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 125000004957 naphthylene group Chemical group 0.000 description 5
- 102100038916 Caspase-5 Human genes 0.000 description 4
- 101100112336 Homo sapiens CASP5 gene Proteins 0.000 description 4
- 101100273286 Mus musculus Casp4 gene Proteins 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 230000003301 hydrolyzing effect Effects 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 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 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000004958 1,4-naphthylene group Chemical group 0.000 description 2
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical group [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical group OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BLLCSHMELHCAKO-UHFFFAOYSA-N P(O)(O)O.P(O)(O)O.P(O)(O)O Chemical compound P(O)(O)O.P(O)(O)O.P(O)(O)O BLLCSHMELHCAKO-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 2
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- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000001627 detrimental effect Effects 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000003760 magnetic stirring Methods 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
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- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 150000003018 phosphorus compounds Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
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- 238000011105 stabilization Methods 0.000 description 2
- 125000004079 stearyl 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])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])[H] 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 2
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 2
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- 238000005406 washing Methods 0.000 description 2
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- JRBDENXMNZQUIP-UHFFFAOYSA-N 2-(hydroxymethyl)-2-methylbutane-1,4-diol Chemical compound OCC(C)(CO)CCO JRBDENXMNZQUIP-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
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- 241000726103 Atta Species 0.000 description 1
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- 125000006519 CCH3 Chemical group 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
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- 101100478715 Drosophila melanogaster Start1 gene Proteins 0.000 description 1
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- 125000003277 amino group Chemical group 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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- XLGKKDZDZBIMRD-UHFFFAOYSA-N dimethyl phenyl phosphite Chemical compound COP(OC)OC1=CC=CC=C1 XLGKKDZDZBIMRD-UHFFFAOYSA-N 0.000 description 1
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- 238000000605 extraction Methods 0.000 description 1
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- RGXCTRIQQODGIZ-UHFFFAOYSA-O isodesmosine Chemical compound OC(=O)C(N)CCCC[N+]1=CC(CCC(N)C(O)=O)=CC(CCC(N)C(O)=O)=C1CCCC(N)C(O)=O RGXCTRIQQODGIZ-UHFFFAOYSA-O 0.000 description 1
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- 239000000463 material Substances 0.000 description 1
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- NYCZNDFWFCCTPA-UHFFFAOYSA-N methyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC)OC1=CC=CC=C1 NYCZNDFWFCCTPA-UHFFFAOYSA-N 0.000 description 1
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 description 1
- NHLUVTZJQOJKCC-UHFFFAOYSA-N n,n-dimethylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(C)C NHLUVTZJQOJKCC-UHFFFAOYSA-N 0.000 description 1
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- DUUPDCPVCHSTFF-UHFFFAOYSA-N nonane Chemical compound [CH2]CCCCCCCC DUUPDCPVCHSTFF-UHFFFAOYSA-N 0.000 description 1
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- 235000005985 organic acids Nutrition 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- WJIBZZVTNMAURL-UHFFFAOYSA-N phosphane;rhodium Chemical compound P.[Rh] WJIBZZVTNMAURL-UHFFFAOYSA-N 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000010454 slate Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- SZWHXXNVLACKBV-UHFFFAOYSA-N tetraethylphosphanium Chemical compound CC[P+](CC)(CC)CC SZWHXXNVLACKBV-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 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
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- QOQNJVLFFRMJTQ-UHFFFAOYSA-N trioctyl phosphite Chemical compound CCCCCCCCOP(OCCCCCCCC)OCCCCCCCC QOQNJVLFFRMJTQ-UHFFFAOYSA-N 0.000 description 1
- QOPBTFMUVTXWFF-UHFFFAOYSA-N tripropyl phosphite Chemical compound CCCOP(OCCC)OCCC QOPBTFMUVTXWFF-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- ILLOBGFGKYTZRO-UHFFFAOYSA-N tris(2-ethylhexyl) phosphite Chemical compound CCCCC(CC)COP(OCC(CC)CCCC)OCC(CC)CCCC ILLOBGFGKYTZRO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/025—Purification; Separation; Stabilisation; Desodorisation of organo-phosphorus compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65744—Esters of oxyacids of phosphorus condensed with carbocyclic or heterocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6578—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and sulfur atoms with or without oxygen atoms, as ring hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US032,906 | 1987-03-31 | ||
| US07/032,906 US4835299A (en) | 1987-03-31 | 1987-03-31 | Process for purifying tertiary organophosphites |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1314053C true CA1314053C (en) | 1993-03-02 |
Family
ID=21867504
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000562929A Expired - Fee Related CA1314053C (en) | 1987-03-31 | 1988-03-30 | Process for purifying tertiary organophosphites |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4835299A (en:Method) |
| EP (1) | EP0285136B2 (en:Method) |
| JP (1) | JPH064660B2 (en:Method) |
| KR (1) | KR930005259B1 (en:Method) |
| CN (1) | CN1019396B (en:Method) |
| CA (1) | CA1314053C (en:Method) |
| DE (1) | DE3886577T3 (en:Method) |
| ES (1) | ES2046996T3 (en:Method) |
| IN (1) | IN171049B (en:Method) |
| MX (1) | MX166895B (en:Method) |
| PL (1) | PL152658B1 (en:Method) |
Families Citing this family (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW213465B (en:Method) * | 1991-06-11 | 1993-09-21 | Mitsubishi Chemicals Co Ltd | |
| US5391799A (en) * | 1992-05-05 | 1995-02-21 | Ciba-Geigy Corporation | Process for the preparation 6-chloro-2,4,8,10-tetra-butyldibenzo[d,f][1,3,2]dioxaphoshepin |
| US5292785A (en) * | 1992-05-05 | 1994-03-08 | Ciba-Geigy Corporation | Bis-phosphite stabilized compositions |
| US5310890A (en) * | 1992-07-22 | 1994-05-10 | Ciba-Geigy Corporation | Carbohydrate substituted dibenzoi(d,g)(1,3,2)dioxaphosphocin stabilizers |
| US5310889A (en) * | 1992-07-22 | 1994-05-10 | Ciba-Geigy Corporation | Carbohydrate substituted dibenzo(d,f)(1,3,2)dioxaphosphepin stabilizers |
| US5789625A (en) * | 1995-12-06 | 1998-08-04 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| US5763670A (en) * | 1995-12-06 | 1998-06-09 | Union Carbide Chemicals & Plastics Technology Corporation | Hydroformylation processes |
| US5892127A (en) * | 1996-04-24 | 1999-04-06 | Union Carbide Chemicals & Plastics Technology Corporation | Processes for producing 1,6-hexanedials and derivatives |
| TW482765B (en) * | 1996-08-05 | 2002-04-11 | Sumitomo Chemical Co | Phosphites, process for producing the same and their use |
| US5892119A (en) * | 1996-11-26 | 1999-04-06 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| US5917095A (en) * | 1996-11-26 | 1999-06-29 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| CN1163463C (zh) | 1998-12-10 | 2004-08-25 | 三菱化学株式会社 | 醛的制备方法 |
| DE10148551A1 (de) * | 2001-10-01 | 2003-04-10 | Bayer Ag | Chirale Monophosphorverbindungen |
| DE10220801A1 (de) * | 2002-05-10 | 2003-11-20 | Oxeno Olefinchemie Gmbh | Verfahren zur Rhodium-katalysierten Hydroformylierung von Olefinen unter Reduzierung der Rhodiumverluste |
| US7317130B2 (en) * | 2002-08-31 | 2008-01-08 | Oxeno Olefinchemie Gmbh | Method for the hydroformylation of olefinically unsaturated compounds, especially olefins, in the presence of cyclic carbonic acid esters |
| KR101035146B1 (ko) | 2006-11-06 | 2011-05-17 | 주식회사 엘지화학 | 옥소 공정에서 재결정화 과정에 의한 촉매 리간드 산화물의 분리 방법 |
| JP5400627B2 (ja) * | 2007-03-20 | 2014-01-29 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | 生成物異性体の制御が改善されたヒドロホルミル化方法 |
| EP2200957B2 (en) | 2007-09-07 | 2016-09-14 | Dow Global Technologies LLC | Hydrogenation of alicyclic dialdehydes to alicyclic diols |
| US7872157B2 (en) * | 2007-12-26 | 2011-01-18 | Eastman Chemical Company | Phosphonite containing catalysts for hydroformylation processes |
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| KR101629043B1 (ko) | 2008-07-03 | 2016-06-09 | 다우 테크놀로지 인베스트먼츠 엘엘씨. | 재순환 촉매 스트림 중의 중질물 제어 방법 |
| CA2743720C (en) | 2008-11-14 | 2019-03-12 | University Of Kansas | Polymer-supported transition metal catalyst complexes and methods of use |
| US7928267B1 (en) | 2009-06-22 | 2011-04-19 | Eastman Chemical Company | Phosphite containing catalysts for hydroformylation processes |
| US8586800B2 (en) | 2009-10-16 | 2013-11-19 | Dow Technology Investments Llc | Gas phase hydroformylation process |
| KR101815328B1 (ko) | 2009-12-22 | 2018-01-04 | 다우 테크놀로지 인베스트먼츠 엘엘씨. | 합성가스 분압의 조절에 의한 혼합된 리간드 하이드로폼일화 공정에서의 노말:아이소 알데하이드 비의 조절 방법 |
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| DE102011002639A1 (de) * | 2011-01-13 | 2012-07-19 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von Biphephos |
| SA112330271B1 (ar) | 2011-04-18 | 2015-02-09 | داو تكنولوجى انفستمنتس ال ال سى | تخفيف التلوث في عمليات هيدروفورملة عن طريق إضافة الماء |
| JP6170059B2 (ja) * | 2011-10-31 | 2017-07-26 | ダウ テクノロジー インベストメンツ リミティド ライアビリティー カンパニー | ポリ亜リン酸エステル配位子の生産における結晶化溶媒の防止 |
| US8796481B2 (en) | 2011-12-30 | 2014-08-05 | Basf Se | Crystalline solvate and non-solvated forms of 6,6′-[[3,3′,5,5′-tetrakis(1,1-dimethylethyl)-[1,1′biphenyl]-2,2′-diyl]bis(oxy)]bis-dibenzo [d,f] [1,3,2]-dioxaphosphepine |
| US9108988B2 (en) | 2011-12-30 | 2015-08-18 | Basf Se | Method of purifying organic diphosphite compounds |
| WO2013098370A1 (en) | 2011-12-30 | 2013-07-04 | Basf Se | Crystalline solvate and non-solvated forms of 6,6'-[[3,3',5,5'-tetrakis(1,1-dimethylethyl)-[1,1'-biphenyl]-2,2'-diyl]bis(oxy)]bis-dibenzo [d,f] [1,3,2]-dioxaphosphepine |
| WO2013098371A1 (de) | 2011-12-30 | 2013-07-04 | Basf Se | Verfahren zur herstellung von 6-chlorodibenzo [d,f][1,3,2]dioxaphosphepin |
| US8841474B2 (en) | 2011-12-30 | 2014-09-23 | Basf Se | Process for preparing 6-chlorodibenzo[D,F][1,3,2]dioxaphosphepin |
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| JP6516670B2 (ja) | 2012-04-12 | 2019-05-22 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 連続的ヒドロホルミル化の際に触媒を補充する方法 |
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| WO2015176928A1 (de) | 2014-05-20 | 2015-11-26 | Evonik Degussa Gmbh | Verfahren zur herstellung von monophosphiten |
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| EP4011891A1 (de) | 2020-12-09 | 2022-06-15 | Covestro Deutschland AG | Verfahren zur herstellung von flammgeschützten pur/pir-hartschaumstoffen |
| EP4259598A1 (en) | 2020-12-14 | 2023-10-18 | Dow Technology Investments LLC | Processes to improve catalytic metal accountability in hydroformylation processes |
| MX2024005136A (es) | 2021-11-11 | 2024-05-16 | Dow Technology Investments Llc | Procesos para recuperar rodio a partir de procesos de hidroformilacion. |
| CN115677757B (zh) * | 2022-11-21 | 2023-07-25 | 江苏极易新材料有限公司 | 一种低氯离子含量的三(2,4-二叔丁基苯基)亚磷酸酯提纯方法 |
| WO2024228768A1 (en) | 2023-05-04 | 2024-11-07 | Dow Technology Investments Llc | Hydroformylation process |
| WO2025029349A1 (en) | 2023-08-03 | 2025-02-06 | Dow Technology Investments Llc | Hydroformylation process |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA694472A (en) * | 1964-09-15 | E. Jones William | Selective extraction process | |
| US3356775A (en) * | 1963-07-31 | 1967-12-05 | Monsanto Co | Purification of triaryl phosphates |
| US3415906A (en) * | 1964-05-29 | 1968-12-10 | Hooker Chemical Corp | Phosphite phospholane and phosphorinane compounds |
| US3511880A (en) * | 1966-09-16 | 1970-05-12 | Union Oil Co | Hydrocarbonylation process |
| US3527809A (en) * | 1967-08-03 | 1970-09-08 | Union Carbide Corp | Hydroformylation process |
| SU389100A1 (ru) * | 1971-05-24 | 1973-07-05 | Способ разделения моно- и диалкиловых эфиров фосфорной кислоты | |
| FR2259104B1 (en:Method) * | 1974-01-25 | 1976-11-26 | Rhone Poulenc Ind | |
| US3876395A (en) * | 1974-03-07 | 1975-04-08 | Union Carbide Corp | Method for the adsorption of sulfur dioxide |
| US3917469A (en) * | 1974-07-24 | 1975-11-04 | Union Carbide Corp | Method for the removal of sulfur dioxide from gas mixtures |
| US4351759A (en) * | 1978-01-03 | 1982-09-28 | Ciba-Geigy Corporation | Alkylated 2,2'-biphenylene phosphites and stabilized compositions |
| DE2837027A1 (de) * | 1978-08-24 | 1980-03-06 | Bayer Ag | Neue phosphorigsaeureester und ihre verwendung zur stabilisierung von polyamiden |
| US4258215A (en) * | 1979-08-29 | 1981-03-24 | Eastman Kodak Company | Hydroformylation process |
| EP0096988B1 (en) * | 1982-06-11 | 1987-07-08 | DAVY McKEE (LONDON) LIMITED | Hydroformylation process |
| EP0096986B1 (en) * | 1982-06-11 | 1987-04-22 | DAVY McKEE (LONDON) LIMITED | Hydroformylation process |
| US4532085A (en) * | 1983-07-05 | 1985-07-30 | Stauffer Chemical Company | Phosphate ester recovery |
| GB8334359D0 (en) * | 1983-12-23 | 1984-02-01 | Davy Mckee Ltd | Process |
| US4599206A (en) * | 1984-02-17 | 1986-07-08 | Union Carbide Corporation | Transition metal complex catalyzed reactions |
| US4737588A (en) * | 1984-12-28 | 1988-04-12 | Union Carbide Corporation | Transition metal complex catalyzed reactions |
| US4668651A (en) * | 1985-09-05 | 1987-05-26 | Union Carbide Corporation | Transition metal complex catalyzed processes |
| US4748261A (en) * | 1985-09-05 | 1988-05-31 | Union Carbide Corporation | Bis-phosphite compounds |
| US4774361A (en) * | 1986-05-20 | 1988-09-27 | Union Carbide Corporation | Transition metal complex catalyzed reactions |
-
1987
- 1987-03-31 US US07/032,906 patent/US4835299A/en not_active Expired - Lifetime
-
1988
- 1988-03-30 CN CN88102776A patent/CN1019396B/zh not_active Expired
- 1988-03-30 KR KR1019880003471A patent/KR930005259B1/ko not_active Expired - Fee Related
- 1988-03-30 DE DE3886577T patent/DE3886577T3/de not_active Expired - Lifetime
- 1988-03-30 MX MX010970A patent/MX166895B/es unknown
- 1988-03-30 IN IN203/MAS/88A patent/IN171049B/en unknown
- 1988-03-30 CA CA000562929A patent/CA1314053C/en not_active Expired - Fee Related
- 1988-03-30 EP EP88105185A patent/EP0285136B2/en not_active Expired - Lifetime
- 1988-03-30 ES ES88105185T patent/ES2046996T3/es not_active Expired - Lifetime
- 1988-03-31 JP JP63076654A patent/JPH064660B2/ja not_active Expired - Lifetime
- 1988-03-31 PL PL1988271548A patent/PL152658B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE3886577T3 (de) | 2000-01-13 |
| US4835299A (en) | 1989-05-30 |
| PL152658B1 (en) | 1991-01-31 |
| JPH064660B2 (ja) | 1994-01-19 |
| EP0285136B1 (en) | 1993-12-29 |
| CN88102776A (zh) | 1988-11-23 |
| JPH02231497A (ja) | 1990-09-13 |
| DE3886577D1 (de) | 1994-02-10 |
| DE3886577T2 (de) | 1994-04-28 |
| KR930005259B1 (ko) | 1993-06-17 |
| KR880011179A (ko) | 1988-10-27 |
| EP0285136B2 (en) | 1999-10-20 |
| CN1019396B (zh) | 1992-12-09 |
| PL271548A1 (en) | 1989-01-23 |
| MX166895B (es) | 1993-02-11 |
| ES2046996T3 (es) | 1994-02-16 |
| EP0285136A3 (en) | 1989-11-23 |
| IN171049B (en:Method) | 1992-07-04 |
| EP0285136A2 (en) | 1988-10-05 |
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| Date | Code | Title | Description |
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| MKLA | Lapsed |