DE69020198T2 - Herstellung von Terephthalsäureestern durch abbauende Umesterung von Alt- oder Neuterephthalaten. - Google Patents
Herstellung von Terephthalsäureestern durch abbauende Umesterung von Alt- oder Neuterephthalaten.Info
- Publication number
- DE69020198T2 DE69020198T2 DE69020198T DE69020198T DE69020198T2 DE 69020198 T2 DE69020198 T2 DE 69020198T2 DE 69020198 T DE69020198 T DE 69020198T DE 69020198 T DE69020198 T DE 69020198T DE 69020198 T2 DE69020198 T2 DE 69020198T2
- Authority
- DE
- Germany
- Prior art keywords
- terephthalate
- alcohol
- glycol
- normal
- process according
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 25
- 238000005809 transesterification reaction Methods 0.000 title description 15
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title description 14
- 230000000593 degrading effect Effects 0.000 title 1
- 150000003504 terephthalic acids Chemical class 0.000 title 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 69
- 238000000034 method Methods 0.000 claims description 52
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 51
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 51
- 230000008569 process Effects 0.000 claims description 50
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 44
- 239000002699 waste material Substances 0.000 claims description 42
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims description 38
- 229920000728 polyester Polymers 0.000 claims description 37
- -1 polyethylene terephthalate Polymers 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 33
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 25
- 150000001298 alcohols Chemical class 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 20
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 16
- 239000006227 byproduct Substances 0.000 claims description 14
- 229920001707 polybutylene terephthalate Polymers 0.000 claims description 13
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 11
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 8
- OEIWPNWSDYFMIL-UHFFFAOYSA-N dioctyl benzene-1,4-dicarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC)C=C1 OEIWPNWSDYFMIL-UHFFFAOYSA-N 0.000 claims description 8
- REIUXOLGHVXAEO-UHFFFAOYSA-N pentadecan-1-ol Chemical compound CCCCCCCCCCCCCCCO REIUXOLGHVXAEO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- DUQLDVZUQAAAMU-UHFFFAOYSA-N bis(8-methylnonyl) benzene-1,4-dicarboxylate Chemical compound CC(C)CCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC(C)C)C=C1 DUQLDVZUQAAAMU-UHFFFAOYSA-N 0.000 claims description 6
- MLIPQTRXLNTCRS-UHFFFAOYSA-N dihexyl benzene-1,4-dicarboxylate Chemical compound CCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCC)C=C1 MLIPQTRXLNTCRS-UHFFFAOYSA-N 0.000 claims description 6
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 claims description 5
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 claims description 5
- 229920001634 Copolyester Polymers 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- PEIIRIVDOVFUIW-UHFFFAOYSA-N bis(7-methyloctyl) benzene-1,4-dicarboxylate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCC(C)C)C=C1 PEIIRIVDOVFUIW-UHFFFAOYSA-N 0.000 claims description 4
- QDTDKYHPHANITQ-UHFFFAOYSA-N 7-methyloctan-1-ol Chemical compound CC(C)CCCCCCO QDTDKYHPHANITQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- YXHAAEIHLXHTJP-UHFFFAOYSA-N 18-methylnonadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCCCO YXHAAEIHLXHTJP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000000047 product Substances 0.000 description 44
- 150000005690 diesters Chemical class 0.000 description 14
- 235000013305 food Nutrition 0.000 description 13
- 229920005644 polyethylene terephthalate glycol copolymer Polymers 0.000 description 11
- WOZVHXUHUFLZGK-UHFFFAOYSA-N terephthalic acid dimethyl ester Natural products COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 9
- 239000012467 final product Substances 0.000 description 7
- 229920003023 plastic Polymers 0.000 description 7
- 239000004033 plastic Substances 0.000 description 7
- 239000004014 plasticizer Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 235000014214 soft drink Nutrition 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000004064 recycling Methods 0.000 description 5
- 238000012958 reprocessing Methods 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 230000035622 drinking Effects 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- OQBLGYCUQGDOOR-UHFFFAOYSA-L 1,3,2$l^{2}-dioxastannolane-4,5-dione Chemical compound O=C1O[Sn]OC1=O OQBLGYCUQGDOOR-UHFFFAOYSA-L 0.000 description 3
- FDSYTWVNUJTPMA-UHFFFAOYSA-N 2-[3,9-bis(carboxymethyl)-3,6,9,15-tetrazabicyclo[9.3.1]pentadeca-1(15),11,13-trien-6-yl]acetic acid Chemical compound C1N(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC2=CC=CC1=N2 FDSYTWVNUJTPMA-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229920001903 high density polyethylene Polymers 0.000 description 3
- 239000004700 high-density polyethylene Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 235000019520 non-alcoholic beverage Nutrition 0.000 description 3
- 239000012785 packaging film Substances 0.000 description 3
- 229920006280 packaging film Polymers 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 235000013334 alcoholic beverage Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 235000012174 carbonated soft drink Nutrition 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 238000010411 cooking Methods 0.000 description 2
- 238000004042 decolorization Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 239000012974 tin catalyst Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
- 244000174111 Brassica adpressa Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Natural products OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- 239000004439 Isononyl alcohol Substances 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- 229920006899 PET, CPET Polymers 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 235000014171 carbonated beverage Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000003413 degradative effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000006140 methanolysis reaction Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 229940051866 mouthwash Drugs 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000009991 scouring Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
Classifications
-
- 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
-
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J11/00—Recovery or working-up of waste materials
- C08J11/04—Recovery or working-up of waste materials of polymers
- C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
- C08J11/18—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material
- C08J11/22—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds
- C08J11/24—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation by treatment with organic material by treatment with organic oxygen-containing compounds containing hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/62—Plastics recycling; Rubber recycling
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Sustainable Development (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/323,977 US4929749A (en) | 1989-03-15 | 1989-03-15 | Production of terephthalate esters by degradative transesterification of scrap or virgin terephthalate polyesters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69020198D1 DE69020198D1 (de) | 1995-07-27 |
| DE69020198T2 true DE69020198T2 (de) | 1996-02-01 |
Family
ID=23261534
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69020198T Expired - Fee Related DE69020198T2 (de) | 1989-03-15 | 1990-03-15 | Herstellung von Terephthalsäureestern durch abbauende Umesterung von Alt- oder Neuterephthalaten. |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4929749A (online.php) |
| EP (1) | EP0388197B1 (online.php) |
| JP (1) | JP2927495B2 (online.php) |
| CA (1) | CA2012227C (online.php) |
| DE (1) | DE69020198T2 (online.php) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5101064A (en) * | 1989-03-15 | 1992-03-31 | Synergistics Industries Limited | Production of terephthalate esters by degradative transesterification of scrap or virgin terephthalate polyesters |
| CN1033970C (zh) * | 1991-12-13 | 1997-02-05 | 化学工业部成都有机硅应用研究技术服务中心 | 用聚酯废料一步法生产增塑剂 |
| US5252615A (en) * | 1992-01-23 | 1993-10-12 | The Sherwin-Williams Company | Aqueous coating compositions from polyethylene terephthalate |
| US5298530A (en) * | 1992-11-25 | 1994-03-29 | Eastman Kodak Company | Process of recovering components from scrap polyester |
| US5304673A (en) * | 1993-01-29 | 1994-04-19 | Enviropur Waste Refining And Technology, Inc. | Process for recovering dimethyl terephthalate and ethylene glycol |
| US5364985A (en) * | 1993-05-24 | 1994-11-15 | Enviropur Waste Refining And Technology, Inc. | Process for separating mixture of ethylene glycol and dimethyl terephthalate polymers |
| US5414022A (en) * | 1994-03-10 | 1995-05-09 | Eastman Kodak Company | Process of recovering components from polyester resins |
| US6675560B2 (en) * | 2001-06-29 | 2004-01-13 | Eastman Chemical Company | PVC food wrap formed from dioctyl terphthalate plasticizer, method of forming same and method of wrapping food therewith |
| US7893122B2 (en) * | 2004-01-27 | 2011-02-22 | Arturo Guadalupe Fregoso-Infante | Chemical process for recycling polyethylene terephthalate (PET) waste |
| US7157139B2 (en) * | 2004-04-19 | 2007-01-02 | Grant W. Doney | Polymer manufacturing process |
| US8476364B2 (en) | 2007-03-29 | 2013-07-02 | Beaulieu Group, Llc | Polymer manufacturing process |
| KR101010065B1 (ko) | 2007-12-04 | 2011-01-24 | 주식회사 엘지화학 | 디이소노닐테레프탈레이트를 포함하는 벽지용 염화비닐계수지 조성물 |
| WO2013143825A1 (en) | 2012-03-30 | 2013-10-03 | Exxonmobil Chemical Patents Inc. | Esterification process |
| US9481628B2 (en) | 2012-03-30 | 2016-11-01 | Exxonmobil Chemical Patents Inc. | Esterification process |
| KR20140027014A (ko) * | 2012-08-23 | 2014-03-06 | 주식회사 엘지화학 | 가소제 조성물 |
| EP2784113B1 (en) * | 2012-10-10 | 2017-11-29 | LG Chem, Ltd. | Plasticizer, plasticizer composition, heat-resistant resin composition and method for preparing same |
| EP2810932A1 (en) * | 2013-06-06 | 2014-12-10 | ExxonMobil Chemical Patents Inc. | Improvements in or relating to plasticiser esters |
| CN105873895A (zh) * | 2013-12-31 | 2016-08-17 | Bp北美公司 | 从含聚酯原料形成芳香二酸和/或芳香二酸前体的方法 |
| JP6481984B2 (ja) | 2014-02-07 | 2019-03-13 | エルジー・ケム・リミテッド | エステル系化合物、これを含む可塑剤組成物、この製造方法、及びこれを含む樹脂組成物 |
| TWI643844B (zh) | 2014-02-07 | 2018-12-11 | Ｌｇ化學股份有限公司 | 塑化劑和樹脂組成物及彼等之製備方法 |
| US9981902B2 (en) | 2015-10-23 | 2018-05-29 | Columbia Insurance Company | Process for production of an ester and diol from reclaimed carpet material |
| US20190308925A1 (en) * | 2016-06-27 | 2019-10-10 | Sabic Global Technologies B.V. | Process for the preparation of dialkyl terephthalates from recycle feedstocks |
| KR102325729B1 (ko) | 2018-11-28 | 2021-11-15 | 주식회사 엘지화학 | 가압 구간을 포함하는 테레프탈레이트계 조성물의 제조방법 |
| CN110746295A (zh) * | 2019-11-13 | 2020-02-04 | 山东成武易信环保科技有限公司 | 一种dotp提纯工艺 |
| WO2022114745A1 (ko) * | 2020-11-24 | 2022-06-02 | 주식회사 엘지화학 | 이소프탈레이트계 가소제 조성물 및 이를 포함하는 수지 조성물 |
| MX2023003090A (es) | 2020-11-24 | 2023-04-14 | Lg Chemical Ltd | Composicion plastificante a base de dicarboxilato de dihexil benceno y composicion de resina que comprende la misma. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1081681A (fr) * | 1952-08-09 | 1954-12-22 | Perfogit | Procédé de récupération de chutes de polyesters synthétiques |
| DE1080540B (de) * | 1959-01-14 | 1960-04-28 | Glanzstoff Ag | Verfahren zur Reinigung von durch Abbau von Polyaethylen-terephthalat mit Methanol unter Druck gewonnenem rohem Terephthalsaeuredimethylester |
| OA05495A (fr) * | 1975-12-16 | 1981-04-30 | Rhone Poulenc Textile | Procédé d'obtention de TEREPHTALATE de DIMETHYLE à partir de déchets de polyester. |
| US4578502A (en) * | 1985-01-22 | 1986-03-25 | Cudmore Warner J G | Polyethylene terephthalate saponification process |
-
1989
- 1989-03-15 US US07/323,977 patent/US4929749A/en not_active Expired - Fee Related
-
1990
- 1990-03-15 DE DE69020198T patent/DE69020198T2/de not_active Expired - Fee Related
- 1990-03-15 EP EP19900302773 patent/EP0388197B1/en not_active Expired - Lifetime
- 1990-03-15 JP JP6551090A patent/JP2927495B2/ja not_active Expired - Fee Related
- 1990-03-15 CA CA 2012227 patent/CA2012227C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US4929749A (en) | 1990-05-29 |
| EP0388197A1 (en) | 1990-09-19 |
| DE69020198D1 (de) | 1995-07-27 |
| US4929749B1 (online.php) | 1992-06-23 |
| JP2927495B2 (ja) | 1999-07-28 |
| CA2012227A1 (en) | 1990-09-15 |
| JPH0356446A (ja) | 1991-03-12 |
| CA2012227C (en) | 2001-08-14 |
| EP0388197B1 (en) | 1995-06-21 |
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