DE60123810T2 - Reinigugsverfahren von polyestervorläufern - Google Patents
Reinigugsverfahren von polyestervorläufern Download PDFInfo
- Publication number
- DE60123810T2 DE60123810T2 DE60123810T DE60123810T DE60123810T2 DE 60123810 T2 DE60123810 T2 DE 60123810T2 DE 60123810 T DE60123810 T DE 60123810T DE 60123810 T DE60123810 T DE 60123810T DE 60123810 T2 DE60123810 T2 DE 60123810T2
- Authority
- DE
- Germany
- Prior art keywords
- oligomer
- catalyst
- hydrogen
- hydrogenation
- polyester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920000728 polyester Polymers 0.000 title claims description 36
- 238000004140 cleaning Methods 0.000 title description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 62
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 54
- 239000003054 catalyst Substances 0.000 claims description 54
- 238000005984 hydrogenation reaction Methods 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 26
- 150000002009 diols Chemical class 0.000 claims description 16
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 15
- 229910052763 palladium Inorganic materials 0.000 claims description 11
- 238000006068 polycondensation reaction Methods 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
- 229910052697 platinum Inorganic materials 0.000 claims description 7
- 239000000155 melt Substances 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 239000002243 precursor Substances 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229910052762 osmium Inorganic materials 0.000 claims description 3
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- 239000010948 rhodium Substances 0.000 claims description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- 229910010413 TiO 2 Inorganic materials 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 239000010457 zeolite Substances 0.000 claims description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 26
- 239000000047 product Substances 0.000 description 19
- 229920000139 polyethylene terephthalate Polymers 0.000 description 13
- 239000005020 polyethylene terephthalate Substances 0.000 description 13
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 12
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 9
- 239000010936 titanium Substances 0.000 description 9
- 229910052719 titanium Inorganic materials 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000012535 impurity Substances 0.000 description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 6
- -1 polyethylene terephthalate Polymers 0.000 description 6
- QPKOBORKPHRBPS-UHFFFAOYSA-N bis(2-hydroxyethyl) terephthalate Chemical compound OCCOC(=O)C1=CC=C(C(=O)OCCO)C=C1 QPKOBORKPHRBPS-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 238000005070 sampling Methods 0.000 description 5
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 150000008376 fluorenones Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- GDQBOARUYXETBF-UHFFFAOYSA-N 1-oxofluorene-2,3-dicarboxylic acid Chemical compound C1=CC=C2C3=CC(C(=O)O)=C(C(O)=O)C(=O)C3=CC2=C1 GDQBOARUYXETBF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910052787 antimony Inorganic materials 0.000 description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 229910052732 germanium Inorganic materials 0.000 description 3
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- ZRPXGXYVWGQWRD-UHFFFAOYSA-N 1-oxofluorene-2,7-dicarboxylic acid Chemical class OC(=O)C1=CC=C2C3=CC=C(C(=O)O)C(=O)C3=CC2=C1 ZRPXGXYVWGQWRD-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000013626 chemical specie Substances 0.000 description 2
- 238000004737 colorimetric analysis Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 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 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003503 terephthalic acid derivatives Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 2
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- CCAMNSZIWUVALK-UHFFFAOYSA-N 1-oxofluorene-2,3,4-tricarboxylic acid Chemical compound C1=CC=C2C3=C(C(=O)O)C(C(O)=O)=C(C(O)=O)C(=O)C3=CC2=C1 CCAMNSZIWUVALK-UHFFFAOYSA-N 0.000 description 1
- LJRFPYMJMQVHQU-UHFFFAOYSA-N 1-oxofluorene-2-carboxylic acid Chemical class C1=CC=C2C3=CC=C(C(=O)O)C(=O)C3=CC2=C1 LJRFPYMJMQVHQU-UHFFFAOYSA-N 0.000 description 1
- FQXGHZNSUOHCLO-UHFFFAOYSA-N 2,2,4,4-tetramethyl-1,3-cyclobutanediol Chemical compound CC1(C)C(O)C(C)(C)C1O FQXGHZNSUOHCLO-UHFFFAOYSA-N 0.000 description 1
- ONJNHSZRRFHSPJ-UHFFFAOYSA-N 2,2,4,4-tetramethylcyclobutane-1,1-diol Chemical compound CC1(C)CC(C)(C)C1(O)O ONJNHSZRRFHSPJ-UHFFFAOYSA-N 0.000 description 1
- IUYYVMKHUXDWEU-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,1-diol Chemical compound CC(C)CC(C)(C)C(O)O IUYYVMKHUXDWEU-UHFFFAOYSA-N 0.000 description 1
- ICPXIRMAMWRMAD-UHFFFAOYSA-N 2-[3-[2-[3-(2-hydroxyethoxy)phenyl]propan-2-yl]phenoxy]ethanol Chemical compound C=1C=CC(OCCO)=CC=1C(C)(C)C1=CC=CC(OCCO)=C1 ICPXIRMAMWRMAD-UHFFFAOYSA-N 0.000 description 1
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 description 1
- IUGOPULVANEDRX-UHFFFAOYSA-N 2-ethylhexane-1,1-diol Chemical compound CCCCC(CC)C(O)O IUGOPULVANEDRX-UHFFFAOYSA-N 0.000 description 1
- PNJNLCNHYSWUPT-UHFFFAOYSA-N 2-methylpentane-1,4-diol Chemical compound CC(O)CC(C)CO PNJNLCNHYSWUPT-UHFFFAOYSA-N 0.000 description 1
- CPHURRLSZSRQFS-UHFFFAOYSA-N 3-[4-[2-[4-(3-hydroxypropoxy)phenyl]propan-2-yl]phenoxy]propan-1-ol Chemical compound C=1C=C(OCCCO)C=CC=1C(C)(C)C1=CC=C(OCCCO)C=C1 CPHURRLSZSRQFS-UHFFFAOYSA-N 0.000 description 1
- KTFJPMPXSYUEIP-UHFFFAOYSA-N 3-benzoylphthalic acid Chemical compound OC(=O)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1C(O)=O KTFJPMPXSYUEIP-UHFFFAOYSA-N 0.000 description 1
- YHFGMFYKZBWPRW-UHFFFAOYSA-N 3-methylpentane-1,1-diol Chemical compound CCC(C)CC(O)O YHFGMFYKZBWPRW-UHFFFAOYSA-N 0.000 description 1
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical group C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 1
- BQDSQOCMNSRCGT-UHFFFAOYSA-N 4-[2-(4-carboxyphenyl)-2-oxoacetyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)C(=O)C1=CC=C(C(O)=O)C=C1 BQDSQOCMNSRCGT-UHFFFAOYSA-N 0.000 description 1
- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- LLLVZDVNHNWSDS-UHFFFAOYSA-N 4-methylidene-3,5-dioxabicyclo[5.2.2]undeca-1(9),7,10-triene-2,6-dione Chemical compound C1(C2=CC=C(C(=O)OC(=C)O1)C=C2)=O LLLVZDVNHNWSDS-UHFFFAOYSA-N 0.000 description 1
- RWQUWTMOHXGTNN-UHFFFAOYSA-N 9-n,10-n-bis(4-butylphenyl)-9-n,10-n-bis(4-methylphenyl)phenanthrene-9,10-diamine Chemical compound C1=CC(CCCC)=CC=C1N(C=1C2=CC=CC=C2C2=CC=CC=C2C=1N(C=1C=CC(C)=CC=1)C=1C=CC(CCCC)=CC=1)C1=CC=C(C)C=C1 RWQUWTMOHXGTNN-UHFFFAOYSA-N 0.000 description 1
- MCUPIHIZTYWHBZ-UHFFFAOYSA-N 9h-fluorene-1,2-dicarboxylic acid Chemical class C1=CC=C2C3=CC=C(C(=O)O)C(C(O)=O)=C3CC2=C1 MCUPIHIZTYWHBZ-UHFFFAOYSA-N 0.000 description 1
- HTPXFGUCAUTOEL-UHFFFAOYSA-N 9h-fluorene-1-carboxylic acid Chemical class C1C2=CC=CC=C2C2=C1C(C(=O)O)=CC=C2 HTPXFGUCAUTOEL-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 239000004609 Impact Modifier Substances 0.000 description 1
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 description 1
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
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- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
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- 229910052786 argon Inorganic materials 0.000 description 1
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
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- 229910021641 deionized water Inorganic materials 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 description 1
- GYUVMLBYMPKZAZ-UHFFFAOYSA-N dimethyl naphthalene-2,6-dicarboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(C(=O)OC)=CC=C21 GYUVMLBYMPKZAZ-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
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- 229910052733 gallium Inorganic materials 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229960002479 isosorbide Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000005453 pelletization Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- XRVCFZPJAHWYTB-UHFFFAOYSA-N prenderol Chemical compound CCC(CC)(CO)CO XRVCFZPJAHWYTB-UHFFFAOYSA-N 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/60—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
- B29B9/00—Making granules
- B29B9/12—Making granules characterised by structure or composition
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
- B29B9/00—Making granules
- B29B9/16—Auxiliary treatment of granules
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
- B29B9/00—Making granules
- B29B9/16—Auxiliary treatment of granules
- B29B2009/165—Crystallizing granules
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US812581 | 1985-12-23 | ||
| US22869500P | 2000-08-29 | 2000-08-29 | |
| US228695P | 2000-08-29 | ||
| US09/812,581 US6380352B1 (en) | 2000-08-29 | 2001-03-20 | Polyester precursor purification process |
| PCT/US2001/026487 WO2002018471A2 (en) | 2000-08-29 | 2001-08-24 | Polyester precursor purification process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60123810D1 DE60123810D1 (de) | 2006-11-23 |
| DE60123810T2 true DE60123810T2 (de) | 2007-03-01 |
Family
ID=26922575
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60123810T Expired - Lifetime DE60123810T2 (de) | 2000-08-29 | 2001-08-24 | Reinigugsverfahren von polyestervorläufern |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US6380352B1 (enExample) |
| EP (1) | EP1313788B1 (enExample) |
| JP (1) | JP2004507560A (enExample) |
| KR (1) | KR100779294B1 (enExample) |
| CN (1) | CN1220716C (enExample) |
| AR (1) | AR033388A1 (enExample) |
| AT (1) | ATE342296T1 (enExample) |
| BR (1) | BR0113498A (enExample) |
| CA (1) | CA2419422C (enExample) |
| DE (1) | DE60123810T2 (enExample) |
| ES (1) | ES2269445T3 (enExample) |
| MX (1) | MXPA03001617A (enExample) |
| TW (1) | TW527373B (enExample) |
| WO (1) | WO2002018471A2 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2146172C1 (ru) * | 1999-07-29 | 2000-03-10 | Институт катализа им.Г.К.Борескова СО РАН | Каталитическая композиция, способ ее приготовления и способ очистки терефталевой кислоты |
| US6762276B2 (en) * | 2002-02-27 | 2004-07-13 | Eastman Chemical Company | Hydrogenation of polyester oligomers containing terephthalic acid residues |
| TW200418901A (en) | 2003-02-25 | 2004-10-01 | Du Pont | Process for the manufacture of polyester via hydrogenation treatment of recycled diol |
| DE10339366A1 (de) * | 2003-08-27 | 2005-03-24 | Dr. Johannes Heidenhain Gmbh | Verfahren und Vorrichtung zur Regelung einer Lichtquelle eines Positionsmessgerätes |
| US7129316B2 (en) | 2004-01-07 | 2006-10-31 | Invista North America S.A R.L. | Process for the manufacture of polyester via hydrogenation treatment of recycled diol |
| JP4752766B2 (ja) * | 2004-12-21 | 2011-08-17 | 日立化成工業株式会社 | 酸無水物系エポキシ樹脂硬化剤の製造方法、酸無水物系エポキシ樹脂硬化剤、エポキシ樹脂組成物、その硬化物及び光半導体装置 |
| US7067615B1 (en) | 2005-06-13 | 2006-06-27 | Eastman Chemical Company | Hydrotreating polyester precursors |
| US7390869B2 (en) * | 2005-06-13 | 2008-06-24 | Eastman Chemical Company | Process for removing metal species in the presence of hydrogen and a porous material and polyester polymer containing reduced amounts of metal species |
| KR101101930B1 (ko) * | 2011-04-19 | 2012-01-02 | 김용남 | 프리캐스트 콘크리트 경량 판상 마감재 |
| US9550713B1 (en) | 2015-07-09 | 2017-01-24 | Loop Industries, Inc. | Polyethylene terephthalate depolymerization |
| US12071519B2 (en) | 2017-09-15 | 2024-08-27 | 9449710 Canada Inc. | Terephthalic acid esters formation |
| US10252976B1 (en) | 2017-09-15 | 2019-04-09 | 9449710 Canada Inc. | Terephthalic acid esters formation |
| UY38276A (es) | 2018-06-25 | 2019-12-31 | 9449710 Canada Inc | Formación de ésteres de ácido tereftálico |
| US11248103B2 (en) | 2019-03-20 | 2022-02-15 | 9449710 Canada Inc. | Process for the depolymerization of polyethylene terephthalate (PET) |
| JPWO2021014962A1 (enExample) * | 2019-07-19 | 2021-01-28 | ||
| IT201900025039A1 (it) * | 2019-12-20 | 2021-06-20 | Garbo S R L | Processo per purificare il bis(2-idrossietil)tereftalato. |
| CA3176833A1 (en) | 2020-06-05 | 2021-12-09 | Clive Alexander Hamilton | A method for manufacturing an oligomeric polyethylene terephthalate (pet) substrate |
| CN115698123A (zh) * | 2020-06-05 | 2023-02-03 | 科氏技术英国有限公司 | 用于制造低聚聚对苯二甲酸乙二酯(pet)底物的方法 |
| WO2025160816A1 (zh) * | 2024-01-31 | 2025-08-07 | 江苏集萃先进纤维材料研究所有限公司 | 基于分步反应逐步结晶的回收纯化bhet的方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1134949A (en) | 1965-05-14 | 1968-11-27 | Sumitomo Chemical Co | Method for treating crude bis--ß-hydroxyethyl terephthalate |
| US3501420A (en) | 1967-10-20 | 1970-03-17 | Eastman Kodak Co | High purity polyester depolymerization products from polyester scrap by polish hydrogenation |
| JPS4836141A (enExample) * | 1971-09-14 | 1973-05-28 | ||
| JPS5828255B2 (ja) | 1974-05-04 | 1983-06-15 | 東洋紡績株式会社 | １，４ シクロヘキサンジメタノ−ル ノ セイゾウホウ |
| DE2504156A1 (de) * | 1975-02-01 | 1976-08-05 | Dynamit Nobel Ag | Niedermolekulare terephthalsaeure- aethylenglykolester, ihre herstellung und verwendung |
| JPH0672922A (ja) * | 1992-08-26 | 1994-03-15 | Toyobo Co Ltd | 廃ポリエチレンテレフタレートから高純度の原料モノマーを回収する方法 |
| US5597891A (en) | 1995-08-01 | 1997-01-28 | Eastman Chemical Company | Process for producing polyester articles having low acetaldehyde content |
| US5648032A (en) | 1995-08-01 | 1997-07-15 | Eastman Chemical Company | Process for producing polyester articles having low acetaldehyde content |
| JP3891454B2 (ja) * | 1996-12-19 | 2007-03-14 | 三井化学株式会社 | 芳香族ジカルボン酸エステルの精製方法 |
-
2001
- 2001-03-20 US US09/812,581 patent/US6380352B1/en not_active Expired - Lifetime
- 2001-08-02 TW TW090118914A patent/TW527373B/zh not_active IP Right Cessation
- 2001-08-10 AR ARP010103842A patent/AR033388A1/es active IP Right Grant
- 2001-08-24 KR KR1020037002870A patent/KR100779294B1/ko not_active Expired - Lifetime
- 2001-08-24 CA CA002419422A patent/CA2419422C/en not_active Expired - Fee Related
- 2001-08-24 EP EP01964409A patent/EP1313788B1/en not_active Expired - Lifetime
- 2001-08-24 WO PCT/US2001/026487 patent/WO2002018471A2/en not_active Ceased
- 2001-08-24 DE DE60123810T patent/DE60123810T2/de not_active Expired - Lifetime
- 2001-08-24 JP JP2002523983A patent/JP2004507560A/ja active Pending
- 2001-08-24 ES ES01964409T patent/ES2269445T3/es not_active Expired - Lifetime
- 2001-08-24 CN CNB018148727A patent/CN1220716C/zh not_active Expired - Fee Related
- 2001-08-24 BR BR0113498-1A patent/BR0113498A/pt not_active Application Discontinuation
- 2001-08-24 AT AT01964409T patent/ATE342296T1/de not_active IP Right Cessation
- 2001-08-24 MX MXPA03001617A patent/MXPA03001617A/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| EP1313788A2 (en) | 2003-05-28 |
| CA2419422A1 (en) | 2002-03-07 |
| EP1313788B1 (en) | 2006-10-11 |
| KR20030045787A (ko) | 2003-06-11 |
| JP2004507560A (ja) | 2004-03-11 |
| CA2419422C (en) | 2007-07-17 |
| ATE342296T1 (de) | 2006-11-15 |
| CN1220716C (zh) | 2005-09-28 |
| MXPA03001617A (es) | 2003-06-04 |
| KR100779294B1 (ko) | 2007-11-27 |
| WO2002018471A2 (en) | 2002-03-07 |
| WO2002018471A3 (en) | 2002-05-30 |
| ES2269445T3 (es) | 2007-04-01 |
| CN1449419A (zh) | 2003-10-15 |
| TW527373B (en) | 2003-04-11 |
| AR033388A1 (es) | 2003-12-17 |
| DE60123810D1 (de) | 2006-11-23 |
| BR0113498A (pt) | 2003-07-29 |
| US6380352B1 (en) | 2002-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |