CA2493344A1 - Titanium-zirconium catalyst compositions and use thereof - Google Patents
Titanium-zirconium catalyst compositions and use thereof Download PDFInfo
- Publication number
- CA2493344A1 CA2493344A1 CA002493344A CA2493344A CA2493344A1 CA 2493344 A1 CA2493344 A1 CA 2493344A1 CA 002493344 A CA002493344 A CA 002493344A CA 2493344 A CA2493344 A CA 2493344A CA 2493344 A1 CA2493344 A1 CA 2493344A1
- Authority
- CA
- Canada
- Prior art keywords
- catalyst composition
- catalyst
- tetraalkyl
- ammonium hydroxide
- molar ratio
- 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.)
- Abandoned
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 129
- 239000000203 mixture Substances 0.000 title claims abstract description 85
- PMTRSEDNJGMXLN-UHFFFAOYSA-N titanium zirconium Chemical compound [Ti].[Zr] PMTRSEDNJGMXLN-UHFFFAOYSA-N 0.000 title description 2
- 239000010936 titanium Substances 0.000 claims abstract description 142
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 43
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 41
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 claims abstract description 32
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 27
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims abstract description 19
- -1 phosphorus compound Chemical class 0.000 claims description 70
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 54
- 229920000728 polyester Polymers 0.000 claims description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 229910052698 phosphorus Inorganic materials 0.000 claims description 19
- 239000011574 phosphorus Substances 0.000 claims description 19
- 229920002215 polytrimethylene terephthalate Polymers 0.000 claims description 19
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 16
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 16
- 239000000047 product Substances 0.000 claims description 16
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 15
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 13
- 238000002156 mixing Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 4
- HMBHAQMOBKLWRX-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-3-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)COC2=C1 HMBHAQMOBKLWRX-UHFFFAOYSA-N 0.000 claims description 3
- KIZQNNOULOCVDM-UHFFFAOYSA-M 2-hydroxyethyl(trimethyl)azanium;hydroxide Chemical compound [OH-].C[N+](C)(C)CCO KIZQNNOULOCVDM-UHFFFAOYSA-M 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 claims description 3
- 229940075419 choline hydroxide Drugs 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- NWEKXBVHVALDOL-UHFFFAOYSA-N butylazanium;hydroxide Chemical compound [OH-].CCCC[NH3+] NWEKXBVHVALDOL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 32
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 29
- 229920000642 polymer Polymers 0.000 description 27
- 230000000052 comparative effect Effects 0.000 description 26
- 230000032050 esterification Effects 0.000 description 23
- 238000005886 esterification reaction Methods 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 21
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 20
- 230000000694 effects Effects 0.000 description 19
- 238000005809 transesterification reaction Methods 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 19
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 18
- 229940035437 1,3-propanediol Drugs 0.000 description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- 238000006068 polycondensation reaction Methods 0.000 description 12
- 239000000835 fiber Substances 0.000 description 11
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical class OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 7
- 150000002905 orthoesters Chemical class 0.000 description 7
- XPGAWFIWCWKDDL-UHFFFAOYSA-N propan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCC[O-].CCC[O-].CCC[O-].CCC[O-] XPGAWFIWCWKDDL-UHFFFAOYSA-N 0.000 description 7
- 229920001283 Polyalkylene terephthalate Polymers 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229920000139 polyethylene terephthalate Polymers 0.000 description 6
- 239000005020 polyethylene terephthalate Substances 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 239000003086 colorant Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 229920001634 Copolyester Polymers 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229920000874 polytetramethylene terephthalate Polymers 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 150000003609 titanium compounds Chemical class 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000002815 homogeneous catalyst Substances 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
- 229940095102 methyl benzoate Drugs 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- 150000002902 organometallic compounds Chemical class 0.000 description 3
- 150000002903 organophosphorus compounds Chemical class 0.000 description 3
- 150000003018 phosphorus compounds Chemical class 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 3
- 150000003755 zirconium compounds Chemical class 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical group CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- HVGAPIUWXUVICC-UHFFFAOYSA-N 6-methylheptan-1-olate;titanium(4+) Chemical compound [Ti+4].CC(C)CCCCC[O-].CC(C)CCCCC[O-].CC(C)CCCCC[O-].CC(C)CCCCC[O-] HVGAPIUWXUVICC-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 229960000250 adipic acid Drugs 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 235000015165 citric acid Nutrition 0.000 description 2
- 229920001577 copolymer Chemical compound 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 229910052732 germanium Inorganic materials 0.000 description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- 235000011090 malic acid Nutrition 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920001281 polyalkylene Polymers 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical group [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical group FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- 229940043375 1,5-pentanediol Drugs 0.000 description 1
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- SKIIKRJAQOSWFT-UHFFFAOYSA-N 2-[3-[1-(2,2-difluoroethyl)piperidin-4-yl]oxy-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound FC(CN1CCC(CC1)OC1=NN(C=C1C=1C=NC(=NC=1)NC1CC2=CC=CC=C2C1)CC(=O)N1CC2=C(CC1)NN=N2)F SKIIKRJAQOSWFT-UHFFFAOYSA-N 0.000 description 1
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- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical compound [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 description 1
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- 125000005487 naphthalate group Chemical group 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
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- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
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- 238000011105 stabilization Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical group [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
Classifications
-
- 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
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
-
- 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
-
- 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
- B01J31/0201—Oxygen-containing compounds
- B01J31/0211—Oxygen-containing compounds with a metal-oxygen link
- B01J31/0212—Alkoxylates
-
- 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
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0239—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L35/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L35/02—Homopolymers or copolymers of esters
-
- 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
- B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
- B01J2231/14—Other (co) polymerisation, e.g. of lactides or epoxides
-
- 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
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39867502P | 2002-07-26 | 2002-07-26 | |
| US60/398,675 | 2002-07-26 | ||
| US10/269,363 | 2002-10-11 | ||
| US10/269,363 US6841505B2 (en) | 2002-07-26 | 2002-10-11 | Titanium-zirconium catalyst compositions and use thereof |
| PCT/US2003/023227 WO2004011139A1 (en) | 2002-07-26 | 2003-07-23 | Titanium-zirconium catalyst compositions and use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2493344A1 true CA2493344A1 (en) | 2004-02-05 |
Family
ID=30772617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002493344A Abandoned CA2493344A1 (en) | 2002-07-26 | 2003-07-23 | Titanium-zirconium catalyst compositions and use thereof |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6841505B2 (enExample) |
| EP (1) | EP1562704A4 (enExample) |
| JP (1) | JP4708021B2 (enExample) |
| KR (1) | KR100967769B1 (enExample) |
| AU (1) | AU2003256776A1 (enExample) |
| CA (1) | CA2493344A1 (enExample) |
| MX (1) | MXPA05000933A (enExample) |
| TW (1) | TW200401668A (enExample) |
| WO (1) | WO2004011139A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7799942B2 (en) * | 2005-08-12 | 2010-09-21 | Eastman Chemical Company | Production of terephthalic acid di-esters |
| US20070129503A1 (en) * | 2005-12-07 | 2007-06-07 | Kurian Joseph V | Poly(trimethylene terephthalate)/poly(alpha-hydroxy acid) molded, shaped articles |
| US20070128459A1 (en) * | 2005-12-07 | 2007-06-07 | Kurian Joseph V | Poly(trimethylene terephthalate)/poly(alpha-hydroxy acid) films |
| US7666501B2 (en) * | 2005-12-07 | 2010-02-23 | E. I. Du Pont De Nemours And Company | Poly(trimethylene terephthalate)/poly(alpha-hydroxy acid) bi-constituent filaments |
| US7741509B2 (en) * | 2007-01-30 | 2010-06-22 | Eastman Chemical Company | Conversion of terephthalic acid to Di-n-butyl terephthalate |
| KR101109045B1 (ko) * | 2008-01-07 | 2012-01-31 | 주식회사 엘지화학 | 지르코늄 화합물을 포함하는 에스테르화 촉매 조성물 및이를 이용한 에스테르 화합물의 제조방법 |
| TWI417283B (zh) * | 2010-04-27 | 2013-12-01 | Kuo Tseng Li | 乳酸酯之製備方法 |
| JP2012046734A (ja) * | 2010-07-30 | 2012-03-08 | Fujifilm Corp | ポリエステルシートの製造方法、並びに、ポリエステルフィルム及びポリエステルフィルムの製造方法 |
| JP6016886B2 (ja) | 2011-04-12 | 2016-10-26 | ビーエーエスエフ コーティングス ゲゼルシャフト ミット ベシュレンクテル ハフツングＢＡＳＦ Ｃｏａｔｉｎｇｓ ＧｍｂＨ | 溶剤含有クリヤーラッカー被覆組成物、その製造法および該溶剤含有クリヤーラッカー被覆組成物の使用 |
| JP5799636B2 (ja) * | 2011-07-26 | 2015-10-28 | 三菱化学株式会社 | ポリエステルの製造方法 |
| WO2015045969A1 (ja) * | 2013-09-25 | 2015-04-02 | 株式会社Adeka | エステル化合物の製造方法 |
| EP2933019A1 (en) * | 2014-04-15 | 2015-10-21 | Henkel AG&Co. KGAA | Storage stable heat activated quaternary ammonium catalysts for epoxy cure |
| EP4174051B1 (en) * | 2020-06-29 | 2025-11-19 | Nitto Kasei Co., Ltd. | Curing catalyst used for curing polymer, method for producing same, moisture-curable composition, and method for producing cured product |
| TWI817105B (zh) * | 2021-04-14 | 2023-10-01 | 長春人造樹脂廠股份有限公司 | 聚酯組合物及其製備方法、製品及應用 |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1039748B (de) | 1953-06-30 | 1958-09-25 | Bayer Ag | Verfahren zur Herstellung von Polyestern |
| US3056818A (en) | 1955-10-13 | 1962-10-02 | Goodrich Co B F | Titanium and zirconium esterification catalysts |
| FR2252328B1 (enExample) | 1973-11-24 | 1979-06-08 | Teijin Ltd | |
| JPS5946253B2 (ja) | 1976-05-11 | 1984-11-12 | 帝人株式会社 | ポリエステルの製造方法 |
| JPS5385891A (en) | 1977-01-05 | 1978-07-28 | Teijin Ltd | Preparation of polyester |
| JPS5840321A (ja) * | 1981-09-04 | 1983-03-09 | Toyobo Co Ltd | 易滑性ポリエステルの製造法 |
| US5120822A (en) | 1990-08-21 | 1992-06-09 | E. I. Du Pont De Nemours And Company | Polyester process comprising the addition of a tetraalkyl zirconate catalyst |
| JPH06234701A (ja) | 1992-03-16 | 1994-08-23 | Mitsui Toatsu Chem Inc | α，β−不飽和カルボン酸エステルの製造方法 |
| US5268503A (en) | 1992-03-16 | 1993-12-07 | Mitsui Toatsu Chemicals, Incorporated | Process for producing α,β-unsaturated carboxylic acid esters |
| JP2823739B2 (ja) | 1992-06-09 | 1998-11-11 | 帝人株式会社 | 金属板貼合せ成形加工用ポリエステルフイルム |
| DE4400300A1 (de) | 1994-01-07 | 1995-07-13 | Akzo Nobel Nv | Verfahren zur Herstellung von film- und faserbildenden Polyestern und Copolyestern |
| GB9612161D0 (en) * | 1996-06-11 | 1996-08-14 | Tioxide Specialties Ltd | Esterification process |
| GB9725419D0 (en) | 1997-12-02 | 1998-01-28 | Tioxide Specialties Ltd | Esterification catalysts |
| US5840957A (en) | 1998-03-16 | 1998-11-24 | E. I. Du Pont De Nemours And Company | Transesterification process using lanthanum compound catalyst |
| US5981690A (en) | 1998-04-17 | 1999-11-09 | E. I. Du Pont De Nemours And Company | Poly(alkylene arylates) having improved optical properties |
| WO1999054379A1 (en) | 1998-04-17 | 1999-10-28 | E.I. Du Pont De Nemours And Company | Poly(alkylene arylates) having optical properties |
| US6255441B1 (en) * | 1998-04-17 | 2001-07-03 | E. I. Du Pont De Nemours And Company | Titanium-containing catalyst composition and processes therefor and therewith |
| US6346070B1 (en) * | 1998-12-25 | 2002-02-12 | Mitsui Chemicals Inc | Catalyst for polyester production, process for producing polyester using the catalyst, polyester obtained by the process, and uses of the polyester |
| US5969056A (en) * | 1999-01-14 | 1999-10-19 | Reichhold, Inc. | Process for preparing esterification products from cyclic organic carbonates using catalysts comprising quaternary ammonium salts |
| IT1307751B1 (it) | 1999-02-04 | 2001-11-19 | Gen Electric | Composizione di catalizzatore contenente fosfati per la preparazionedi poliesteri e procedimenti relativi. |
| US6512080B2 (en) | 1999-04-22 | 2003-01-28 | Shell Oil Company | Process of producing polytrimethylene terephthalate (PTT) |
| GB9912210D0 (en) | 1999-05-25 | 1999-07-28 | Acma Ltd | Esterification catalysts |
| US6407269B2 (en) | 1999-06-08 | 2002-06-18 | Kao Corporation | Catalyst for transesterification |
| MXPA02001942A (es) | 1999-08-25 | 2002-10-31 | Du Pont | Preparacion de poli(trimetilen tereftalato) con bajo nivel de di(1,3-propilenglicol). |
| US6043335A (en) | 1999-10-04 | 2000-03-28 | General Electric Company | Phosphate-containing catalyst composition for the preparation of polyesters, and related processes |
| US6075115A (en) | 1999-10-19 | 2000-06-13 | E. I. Du Pont De Nemours And Company | Process for the production of 5-sulfo isophthalate bis-glycolate ester metal salts and oxysulfonated polyesters made therefrom |
| US6166170A (en) | 1999-12-02 | 2000-12-26 | E. I. Du Pont De Nemours And Company | Esterification catalysts and processes therefor and therewith |
| GB0002156D0 (en) | 2000-02-01 | 2000-03-22 | Acma Ltd | Esterification catalyst compositions |
| US6255442B1 (en) | 2000-02-08 | 2001-07-03 | E. I. Du Pont De Nemours And Company | Esterification process |
| US6353062B1 (en) | 2000-02-11 | 2002-03-05 | E. I. Du Pont De Nemours And Company | Continuous process for producing poly(trimethylene terephthalate) |
| ATE265486T1 (de) | 2000-02-11 | 2004-05-15 | Du Pont | Kontinuierliches verfahren zur herstellung von polytrimethylenterephthalat |
| US6576774B2 (en) | 2000-07-20 | 2003-06-10 | Shell Oil Company | Process for recycling polytrimethylene terephthalate cyclic dimer |
| BR0115879A (pt) * | 2000-11-21 | 2005-02-01 | Ici Plc | Catalisador de esterificação, processo de poliéster e artigo de poliéster |
| DE10059612A1 (de) * | 2000-12-01 | 2002-06-20 | Bayer Ag | Titan-/Zirkonium-Katalysatoren sowie deren Verwendung zur Herstellung von Estern oder Polyestern |
-
2002
- 2002-10-11 US US10/269,363 patent/US6841505B2/en not_active Expired - Fee Related
-
2003
- 2003-07-23 MX MXPA05000933A patent/MXPA05000933A/es active IP Right Grant
- 2003-07-23 KR KR1020057001343A patent/KR100967769B1/ko not_active Expired - Fee Related
- 2003-07-23 AU AU2003256776A patent/AU2003256776A1/en not_active Abandoned
- 2003-07-23 EP EP03771817A patent/EP1562704A4/en not_active Withdrawn
- 2003-07-23 JP JP2004524797A patent/JP4708021B2/ja not_active Expired - Fee Related
- 2003-07-23 WO PCT/US2003/023227 patent/WO2004011139A1/en not_active Ceased
- 2003-07-23 CA CA002493344A patent/CA2493344A1/en not_active Abandoned
- 2003-07-25 TW TW092120410A patent/TW200401668A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US6841505B2 (en) | 2005-01-11 |
| JP4708021B2 (ja) | 2011-06-22 |
| EP1562704A4 (en) | 2009-08-12 |
| MXPA05000933A (es) | 2005-03-23 |
| KR100967769B1 (ko) | 2010-07-05 |
| EP1562704A1 (en) | 2005-08-17 |
| TW200401668A (en) | 2004-02-01 |
| AU2003256776A1 (en) | 2004-02-16 |
| WO2004011139A1 (en) | 2004-02-05 |
| KR20050025668A (ko) | 2005-03-14 |
| US20040018938A1 (en) | 2004-01-29 |
| JP2005533645A (ja) | 2005-11-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |