JP2015505882A - ポリエチレンテレフタレートの製造のための新たな触媒錯体を合成するプロセス - Google Patents
ポリエチレンテレフタレートの製造のための新たな触媒錯体を合成するプロセス Download PDFInfo
- Publication number
- JP2015505882A JP2015505882A JP2014546356A JP2014546356A JP2015505882A JP 2015505882 A JP2015505882 A JP 2015505882A JP 2014546356 A JP2014546356 A JP 2014546356A JP 2014546356 A JP2014546356 A JP 2014546356A JP 2015505882 A JP2015505882 A JP 2015505882A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- polyethylene terephthalate
- production
- reaction
- boric acid
- 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.)
- Pending
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 66
- 229920000139 polyethylene terephthalate Polymers 0.000 title claims abstract description 60
- 239000005020 polyethylene terephthalate Substances 0.000 title claims abstract description 57
- 238000000034 method Methods 0.000 title claims abstract description 34
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 30
- -1 polyethylene terephthalate Polymers 0.000 title claims abstract description 20
- 230000002194 synthesizing effect Effects 0.000 title description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 80
- 150000003751 zinc Chemical class 0.000 claims abstract description 24
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000004327 boric acid Substances 0.000 claims abstract description 23
- 239000002904 solvent Substances 0.000 claims abstract description 23
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002244 precipitate Substances 0.000 claims abstract description 12
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 229920000642 polymer Polymers 0.000 claims description 13
- 238000006116 polymerization reaction Methods 0.000 claims description 12
- 239000011701 zinc Substances 0.000 claims description 12
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 9
- 150000002334 glycols Chemical class 0.000 claims description 8
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 7
- 239000012298 atmosphere Substances 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- 239000004705 High-molecular-weight polyethylene Substances 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract description 11
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 24
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 20
- 238000006068 polycondensation reaction Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 229910052787 antimony Inorganic materials 0.000 description 10
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 4
- 239000007790 solid phase Substances 0.000 description 4
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 4
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 230000032050 esterification Effects 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
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000013110 organic ligand Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- 229910052719 titanium Inorganic materials 0.000 description 3
- 150000003609 titanium compounds Chemical class 0.000 description 3
- 150000003752 zinc compounds Chemical class 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 230000000873 masking effect Effects 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229920006127 amorphous resin Polymers 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
- 150000001463 antimony compounds Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 238000011021 bench scale process Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 125000005619 boric acid group Chemical group 0.000 description 1
- 235000012206 bottled water Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- JVLRYPRBKSMEBF-UHFFFAOYSA-K diacetyloxystibanyl acetate Chemical compound [Sb+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JVLRYPRBKSMEBF-UHFFFAOYSA-K 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium oxide Inorganic materials O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000003988 headspace gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical compound [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- YLLIGHVCTUPGEH-UHFFFAOYSA-M potassium;ethanol;hydroxide Chemical compound [OH-].[K+].CCO YLLIGHVCTUPGEH-UHFFFAOYSA-M 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000000196 viscometry Methods 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- SRWMQSFFRFWREA-UHFFFAOYSA-M zinc formate Chemical compound [Zn+2].[O-]C=O SRWMQSFFRFWREA-UHFFFAOYSA-M 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
- C08G63/84—Boron, aluminium, gallium, indium, thallium, rare-earth metals, 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
-
- 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
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
- C08G63/183—Terephthalic acids
-
- 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
- C08G63/83—Alkali metals, alkaline earth metals, beryllium, magnesium, copper, silver, gold, zinc, cadmium, mercury, manganese, 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/20—Complexes comprising metals of Group II (IIA or IIB) as the central metal
- B01J2531/26—Zinc
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyesters Or Polycarbonates (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11009910.8 | 2011-12-16 | ||
| EP11009910 | 2011-12-16 | ||
| PCT/EP2012/005135 WO2013087199A1 (en) | 2011-12-16 | 2012-12-13 | Process for synthesizing a new catalyst complex for the production of polyethylene terephthlate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2015505882A true JP2015505882A (ja) | 2015-02-26 |
| JP2015505882A5 JP2015505882A5 (https=) | 2016-02-12 |
Family
ID=47469868
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014546356A Pending JP2015505882A (ja) | 2011-12-16 | 2012-12-13 | ポリエチレンテレフタレートの製造のための新たな触媒錯体を合成するプロセス |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8629234B2 (https=) |
| EP (1) | EP2791202B1 (https=) |
| JP (1) | JP2015505882A (https=) |
| CN (1) | CN104105736B (https=) |
| WO (1) | WO2013087199A1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2019070099A (ja) * | 2017-10-05 | 2019-05-09 | 遠東新世紀股▲ふん▼有限公司 | ポリエステル樹脂製造用の安定剤、その製造方法、該安定剤を用いたポリエステル樹脂の製造方法、及びそれにより製造されたポリエステル樹脂 |
| JP2023522074A (ja) * | 2020-04-21 | 2023-05-26 | ソルベイ スペシャルティ ポリマーズ ユーエスエー， エルエルシー | ポリエステル微細粉末の製造方法 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105968332A (zh) * | 2016-07-12 | 2016-09-28 | 安徽红太阳新材料有限公司 | 催化环酯聚合的苯并硼唑金属配合物及其应用 |
| CN111423569B (zh) * | 2020-04-22 | 2022-11-15 | 浙江恒逸石化研究院有限公司 | 一种抑菌可降解聚对苯二甲酸乙二醇酯共聚酯及其制备方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10330466A (ja) * | 1997-06-04 | 1998-12-15 | Polyplastics Co | ポリエステル樹脂の製造法 |
| WO2002016467A1 (fr) * | 2000-08-22 | 2002-02-28 | Mitsui Chemicals, Inc. | Catalyseurs permettant la production de polyester, procede de production de polyester, et polyester |
| JP2004217887A (ja) * | 2002-12-27 | 2004-08-05 | Mitsubishi Chemicals Corp | ポリエステル製造用触媒およびそれを用いるポリエステルの製造方法 |
| JP2007528433A (ja) * | 2004-03-11 | 2007-10-11 | サウディ ベーシック インダストリーズ コーポレイション | テレフタル酸とエチレングリコールからポリエチレンテレフタレートを製造するための触媒組成物、及びその方法 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL97835C (https=) | 1953-04-06 | 1900-01-01 | ||
| BE542060A (https=) | 1954-10-14 | |||
| GB805534A (en) * | 1955-03-18 | 1958-12-10 | Gevaert Photo Prod Nv | Improvements in or relating to catalytic condensation of diglycolesters of dicarboxylic acids |
| US2973339A (en) | 1955-08-11 | 1961-02-28 | Linear terephthalate polyesters of | |
| US3047536A (en) | 1957-02-05 | 1962-07-31 | Dow Chemical Co | Polyesters |
| US3133113A (en) | 1960-09-27 | 1964-05-12 | Jefferson Chem Co Inc | Method for preparing polycarbonate esters |
| DE1595667A1 (de) * | 1966-08-16 | 1970-01-22 | Hoechst Ag | Verfahren zur Herstellung linearer Polyester |
| JPS568431A (en) | 1979-07-03 | 1981-01-28 | Nippon Ester Co Ltd | Production of polyester |
| US4254241A (en) * | 1979-12-12 | 1981-03-03 | Union Carbide Corporation | Process for producing polyoxyalkylene glycol modified polyesters |
| JPH0781002B2 (ja) | 1988-12-09 | 1995-08-30 | 三菱レイヨン株式会社 | 共重合ポリエステルの製造方法 |
| US5017680A (en) | 1990-07-03 | 1991-05-21 | Eastman Kodak Company | Process and catalyst-inhibitor systems for preparing poly(ethylene terephthalate) |
| US6133404A (en) | 1998-12-26 | 2000-10-17 | National Institute Of Technology And Quality | Polyester and formation process thereof |
| ATE293652T1 (de) | 1999-12-10 | 2005-05-15 | Equipolymers Gmbh | Katalysatorsysteme für polykondensationsreaktionen |
| US6489433B2 (en) | 2001-02-23 | 2002-12-03 | E. I. Du Pont De Nemours And Company | Metal-containing composition and process therewith |
| US7300998B2 (en) * | 2002-02-14 | 2007-11-27 | Mitsui Chemicals, Inc. | Polyester resin and catalyst for polyester production, process for producing polyester resin with the catalyst, polyester resin obtained with the catalyst, and hollow molded container comprising the polyester resins |
| JP2011526876A (ja) | 2008-06-30 | 2011-10-20 | エムイーエムシー・エレクトロニック・マテリアルズ・インコーポレイテッド | アンバランス磁場及び同方向回転を用いた成長シリコン結晶の融液−固体界面形状の制御方法 |
| TWI473832B (zh) | 2009-03-13 | 2015-02-21 | Saudi Basic Ind Corp | 聚對酞酸乙二酯的製造方法 |
| EP2287225A1 (en) | 2009-08-20 | 2011-02-23 | Saudi Basic Industries Corporation | Process for making polyethylene terephthalate |
-
2012
- 2012-12-13 EP EP12808684.0A patent/EP2791202B1/en not_active Not-in-force
- 2012-12-13 WO PCT/EP2012/005135 patent/WO2013087199A1/en not_active Ceased
- 2012-12-13 CN CN201280061996.6A patent/CN104105736B/zh not_active Expired - Fee Related
- 2012-12-13 JP JP2014546356A patent/JP2015505882A/ja active Pending
- 2012-12-17 US US13/716,555 patent/US8629234B2/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10330466A (ja) * | 1997-06-04 | 1998-12-15 | Polyplastics Co | ポリエステル樹脂の製造法 |
| WO2002016467A1 (fr) * | 2000-08-22 | 2002-02-28 | Mitsui Chemicals, Inc. | Catalyseurs permettant la production de polyester, procede de production de polyester, et polyester |
| JP2004217887A (ja) * | 2002-12-27 | 2004-08-05 | Mitsubishi Chemicals Corp | ポリエステル製造用触媒およびそれを用いるポリエステルの製造方法 |
| JP2007528433A (ja) * | 2004-03-11 | 2007-10-11 | サウディ ベーシック インダストリーズ コーポレイション | テレフタル酸とエチレングリコールからポリエチレンテレフタレートを製造するための触媒組成物、及びその方法 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2019070099A (ja) * | 2017-10-05 | 2019-05-09 | 遠東新世紀股▲ふん▼有限公司 | ポリエステル樹脂製造用の安定剤、その製造方法、該安定剤を用いたポリエステル樹脂の製造方法、及びそれにより製造されたポリエステル樹脂 |
| JP2023522074A (ja) * | 2020-04-21 | 2023-05-26 | ソルベイ スペシャルティ ポリマーズ ユーエスエー， エルエルシー | ポリエステル微細粉末の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2013087199A1 (en) | 2013-06-20 |
| EP2791202A1 (en) | 2014-10-22 |
| US8629234B2 (en) | 2014-01-14 |
| EP2791202B1 (en) | 2019-05-08 |
| CN104105736A (zh) | 2014-10-15 |
| CN104105736B (zh) | 2016-08-24 |
| US20130158227A1 (en) | 2013-06-20 |
| WO2013087199A8 (en) | 2014-07-31 |
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