CN1195727C - 双-β-羟乙基对苯二甲酸酯的制造方法及精制方法 - Google Patents
双-β-羟乙基对苯二甲酸酯的制造方法及精制方法 Download PDFInfo
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- CN1195727C CN1195727C CNB998114219A CN99811421A CN1195727C CN 1195727 C CN1195727 C CN 1195727C CN B998114219 A CNB998114219 A CN B998114219A CN 99811421 A CN99811421 A CN 99811421A CN 1195727 C CN1195727 C CN 1195727C
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- hydroxyethyl terephthalate
- terephthalate
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 34
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- FYIBGDKNYYMMAG-UHFFFAOYSA-N ethane-1,2-diol;terephthalic acid Chemical compound OCCO.OC(=O)C1=CC=C(C(O)=O)C=C1 FYIBGDKNYYMMAG-UHFFFAOYSA-N 0.000 claims description 4
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- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
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- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical class C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 2
- 229940059574 pentaerithrityl Drugs 0.000 description 2
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
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- AFPHTEQTJZKQAQ-UHFFFAOYSA-N 3-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1 AFPHTEQTJZKQAQ-UHFFFAOYSA-N 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- 229910052732 germanium Inorganic materials 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 229910052742 iron Inorganic materials 0.000 description 1
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- 230000014759 maintenance of location Effects 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
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- 238000002844 melting Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
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- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/80—Phthalic acid esters
- C07C69/82—Terephthalic acid esters
-
- 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
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- 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
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
Abstract
Description
1.光学密度 | 0.059 | |
2.酸值(KOH mg/g) | 0.4 | |
3.皂化值(KOH mg/g) | 439 | |
4.融点(℃) | 112 | |
5.白度 | L=98.7,a=-0.7,b=1.2 | |
6.阳离子总重量(ppm) | 0.76 | |
7.阴离子总重量(ppm) | 0 | |
8.双-β-羟乙基对苯二甲酸酯(重量%) | 97.93 | |
9.单-β-羟乙基对苯二甲酸酯(重量%) | 1.33 | |
10.低聚物(重量%) | 0.74 |
1.特性粘度[η] | 0.695 |
2.二甘醇(重量%) | 1.11 |
3.末端羧基(μeq/g) | 9.9 |
4.白度 | L=83.0,a=-2.2,b=-4.5 |
分子蒸馏机的处理液量(kg) 31.6 |
分子蒸馏机的处理时间(min) 74.5 |
精制的双-β-羟乙基对苯二甲酸酯回收量(kg) 29.4 |
精制的双-β-羟乙基对苯二甲酸酯回收率(%) 98.1 |
低聚物生成量(kg) 0.21 |
低聚物生成率(%) 0.7 |
光学密度 0.059 |
酸值(KOH mg/g) 0.4 |
皂化值(KOH mg/g) 439 |
熔点(℃) 112 |
白度 L=98.7,a=-0.7,b=1.2 |
阳离子总重量(ppm) 0.76 |
阴离子总重量(ppm) 0 |
双-β-羟乙基对苯二甲酸酯(重量%) 97.93 |
单-β-羟乙基对苯二甲酸酯(重量%) 1.33 |
低聚物(重量%) 0.74 |
特性粘度[η] | 0.695 |
二甘醇(重量%) | 1.11 |
末端羧基(μeq/g) | 9.9 |
白度 | L=83.0,a=-2.2,b=-4.5 |
分子蒸馏机的处理液量(kg) 21 |
分子蒸馏机的处理时间(min) 49.7 |
精制的双-β-羟乙基对苯二甲酸酯回收量(kg) 17.5 |
精制的双-β-羟乙基对苯二甲酸酯回收率(%) 87.4 |
低聚物生成量(kg) 0.74 |
低聚物生成率(%) 3.7 |
分子蒸馏机的处理液量(kg) 21 |
分子蒸馏机的处理时间(min) 49.7 |
精制的双-β-羟乙基对苯二甲酸酯回收量(kg) 13.8 |
精制的双-β-羟乙基对苯二甲酸酯回收率(%) 69.2 |
低聚物生成量(kg) 1.84 |
低聚物生成率(%) 9.2 |
Claims (6)
Applications Claiming Priority (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP220804/1999 | 1999-08-04 | ||
JP22080499A JP2001048837A (ja) | 1999-08-04 | 1999-08-04 | イオン含有量の少ないビス−β−ヒドロキシエチルテレフタレートの製造法 |
JP22266399A JP3782905B2 (ja) | 1999-08-05 | 1999-08-05 | 粗ビス−β−ヒドロキシエチルテレフタレートの精製方法および精製ビス−β−ヒドロキシエチルテレフタレート |
JP222664/1999 | 1999-08-05 | ||
JP22266499A JP3782906B2 (ja) | 1999-08-05 | 1999-08-05 | 粗ビス−β−ヒドロキシエチルテレフタレート精製方法 |
JP222663/1999 | 1999-08-05 | ||
JP226033/1999 | 1999-08-10 | ||
JP22603399A JP3782907B2 (ja) | 1999-08-10 | 1999-08-10 | ビス−β−ヒドロキシエチルテレフタレートおよび/またはその低縮合物の製造法 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
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CNA2004100013328A Division CN1511823A (zh) | 1999-08-04 | 1999-12-24 | 双-β-羟乙基对苯二甲酸酯的制造方法及精制方法 |
CNA2004100013313A Division CN1511821A (zh) | 1999-08-04 | 1999-12-24 | 双-β-羟乙基对苯二甲酸酯的制造方法及精制方法 |
Publications (2)
Publication Number | Publication Date |
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CN1320113A CN1320113A (zh) | 2001-10-31 |
CN1195727C true CN1195727C (zh) | 2005-04-06 |
Family
ID=27476978
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
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CNA2004100013328A Pending CN1511823A (zh) | 1999-08-04 | 1999-12-24 | 双-β-羟乙基对苯二甲酸酯的制造方法及精制方法 |
CNA2004100013313A Pending CN1511821A (zh) | 1999-08-04 | 1999-12-24 | 双-β-羟乙基对苯二甲酸酯的制造方法及精制方法 |
CNB998114219A Expired - Lifetime CN1195727C (zh) | 1999-08-04 | 1999-12-24 | 双-β-羟乙基对苯二甲酸酯的制造方法及精制方法 |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
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CNA2004100013328A Pending CN1511823A (zh) | 1999-08-04 | 1999-12-24 | 双-β-羟乙基对苯二甲酸酯的制造方法及精制方法 |
CNA2004100013313A Pending CN1511821A (zh) | 1999-08-04 | 1999-12-24 | 双-β-羟乙基对苯二甲酸酯的制造方法及精制方法 |
Country Status (13)
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---|---|
US (2) | US6630601B1 (zh) |
EP (1) | EP1120394B1 (zh) |
KR (3) | KR100740059B1 (zh) |
CN (3) | CN1511823A (zh) |
AT (1) | ATE275538T1 (zh) |
AU (1) | AU764053B2 (zh) |
CA (1) | CA2318761A1 (zh) |
DE (1) | DE69920025T2 (zh) |
ES (1) | ES2228142T3 (zh) |
HK (1) | HK1040236A1 (zh) |
ID (1) | ID26736A (zh) |
TW (1) | TW506968B (zh) |
WO (1) | WO2001010812A1 (zh) |
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WO2002010117A1 (fr) | 2000-07-31 | 2002-02-07 | Aies Co., Ltd. | BIS-β-HYDROXYETHYLE TEREPHTHALATE |
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US7211193B2 (en) * | 2002-06-04 | 2007-05-01 | Pet Rebirth Co., Ltd. | Processes for the purification of bis(2-hydroxyethyl)terephthalate |
CN100404583C (zh) | 2003-10-08 | 2008-07-23 | Pet再生股份有限公司 | 成形用聚对苯二甲酸乙二醇酯及其制造方法 |
US7192988B2 (en) * | 2004-09-30 | 2007-03-20 | Invista North America S.Ar.L. | Process for recycling polyester materials |
US8541477B2 (en) * | 2011-03-04 | 2013-09-24 | International Business Machines Corporation | Methods of depolymerizing terephthalate polyesters |
CN102816069B (zh) * | 2012-08-16 | 2014-06-18 | 无锡格瑞恩环保科技有限公司 | 对苯二甲酸二(2-羟乙基)酯的制备方法 |
EP3140281B1 (en) * | 2014-05-05 | 2018-03-14 | Resinate Materials Group, Inc. | Improved recycle-content polyester polyols |
WO2015171433A1 (en) | 2014-05-05 | 2015-11-12 | Resinate Materials Group, Inc. | Polyester polyols from thermoplastic polyesters and dimer fatty acids |
US10414859B2 (en) | 2014-08-20 | 2019-09-17 | Resinate Materials Group, Inc. | High recycle content polyester polyols |
WO2016069622A1 (en) | 2014-10-29 | 2016-05-06 | Resinate Materials Group, Inc. | High recycle content polyester polyols from hydroxy-functional ketal acids, esters or amides |
CN107207713A (zh) | 2015-01-21 | 2017-09-26 | 瑞森内特材料集团有限公司 | 由热塑性聚酯和木质素或单宁获得的高回收含量多元醇 |
US9522976B2 (en) | 2015-03-20 | 2016-12-20 | Resinate Materials Group, Inc. | Cycloaliphatic polyester polyols from thermoplastic polyesters |
WO2016153780A1 (en) | 2015-03-20 | 2016-09-29 | Resinate Materials Group, Inc. | Cycloaliphatic polyester polyols from thermoplastic polyesters |
EP3283545A1 (en) | 2015-04-14 | 2018-02-21 | Resinate Materials Group, Inc. | Polyester polyols with increased clarity |
US20170001946A1 (en) * | 2015-07-02 | 2017-01-05 | Sadesh Sookraj | Terephthalate derivatives and compositions thereof |
WO2017058504A1 (en) | 2015-10-02 | 2017-04-06 | Resinate Materials Group, Inc. | High performance coatings |
FR3092324B1 (fr) | 2019-02-01 | 2021-04-23 | Ifp Energies Now | Procédé de production d’un polyester téréphtalate intégrant un procédé de dépolymérisation |
FR3092323B1 (fr) * | 2019-02-01 | 2021-06-04 | Ifp Energies Now | Procédé de production d’un polyester téréphtalate à partir d’un mélange monomérique comprenant un diester |
NL2023686B1 (en) * | 2019-08-22 | 2021-04-13 | Ioniqa Tech B V | Composition of BHET and use thereof |
KR102431854B1 (ko) * | 2019-11-08 | 2022-08-10 | 코오롱인더스트리 주식회사 | 스펀본드 부직포 및 이를 이용한 타일카페트 |
FR3105235B1 (fr) | 2019-12-19 | 2022-10-07 | Ifp Energies Now | Procédé amélioré de dépolymérisation d’un polyester comprenant du polyéthylène téréphtalate |
FR3105236B1 (fr) | 2019-12-19 | 2022-12-16 | Ifp Energies Now | Procédé optimisé de dépolymérisation d’un polyester comprenant du polyéthylène téréphtalate |
IT201900025039A1 (it) | 2019-12-20 | 2021-06-20 | Garbo S R L | Processo per purificare il bis(2-idrossietil)tereftalato. |
FR3106134B1 (fr) | 2020-01-09 | 2022-12-16 | Ifp Energies Now | Procédé optimisé de dépolymérisation par glycolyse d’un polyester comprenant du polyéthylène téréphtalate |
US11845863B2 (en) | 2020-05-04 | 2023-12-19 | Carlisle Construction Materials, LLC | Polyurethane dispersions and their use to produce coatings and adhesives |
KR102583652B1 (ko) * | 2020-10-26 | 2023-09-26 | 에스케이케미칼 주식회사 | 재사용 단량체를 포함하는 폴리에스테르 공중합체의 제조 방법 |
KR102583653B1 (ko) * | 2020-11-11 | 2023-09-26 | 에스케이케미칼 주식회사 | 재사용 단량체를 포함하는 폴리에스테르 공중합체 |
CN114656684A (zh) * | 2020-12-23 | 2022-06-24 | 科泽新材料有限公司 | 一种利用废旧pet聚酯制备高纯再生pet聚酯的方法 |
GB2604098A (en) * | 2021-02-12 | 2022-08-31 | Poseidon Plastics Ltd | Polymerisation |
CN115141363A (zh) * | 2021-03-30 | 2022-10-04 | 科泽新材料股份有限公司 | 一种利用废聚酯制备再生阳离子聚酯的方法 |
FR3124186B1 (fr) | 2021-06-17 | 2024-04-12 | Ifp Energies Now | Procédé de preparation d’un monomere diester purifie et decolore par dépolymérisation d’une charge polyester |
KR20230050891A (ko) * | 2021-10-08 | 2023-04-17 | 에스케이케미칼 주식회사 | 재사용 단량체를 포함하는, 압출 가공성이 개선된 폴리에스테르 공중합체 |
KR20230072045A (ko) * | 2021-11-17 | 2023-05-24 | 에스케이케미칼 주식회사 | 재사용 비스-2-히드록시에틸테레프탈레이트를 사용한 폴리에스테르 공중합체의 제조 방법 |
FR3130278A1 (fr) | 2021-12-10 | 2023-06-16 | IFP Energies Nouvelles | Procede de production d’un polyester ayant une temperature de cristallisation reduite |
FR3130804A1 (fr) | 2021-12-17 | 2023-06-23 | IFP Energies Nouvelles | Bis(2-hydroxyethyle) terephtalate ayant une teneur en azote faible |
KR20230132222A (ko) * | 2022-03-08 | 2023-09-15 | 에스케이케미칼 주식회사 | 재생 비스-2-히드록시에틸테레프탈레이트를 이용한 폴리에스테르 수지 및 이를 포함하는 물품 |
KR20230149644A (ko) * | 2022-04-20 | 2023-10-27 | 에스케이케미칼 주식회사 | 재생 비스(2-히드록시에틸)테레프탈레이트를 포함하는 폴리에스테르 수지 및 이를 이용한 필름 |
WO2023217707A1 (en) | 2022-05-10 | 2023-11-16 | Polymetrix Ag | Method for the preparation of a polyester |
EP4276131A1 (en) | 2022-05-10 | 2023-11-15 | Polymetrix AG | Method for the preparation of a polyester |
KR20240024420A (ko) * | 2022-08-16 | 2024-02-26 | 에스케이케미칼 주식회사 | 폴리에스테르 수지 혼합물, 이의 제조방법 및 이로부터 제조된 폴리에스테르 필름 |
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-
1999
- 1999-12-24 ES ES99961372T patent/ES2228142T3/es not_active Expired - Lifetime
- 1999-12-24 US US09/622,518 patent/US6630601B1/en not_active Expired - Lifetime
- 1999-12-24 AT AT99961372T patent/ATE275538T1/de not_active IP Right Cessation
- 1999-12-24 AU AU18005/00A patent/AU764053B2/en not_active Expired
- 1999-12-24 CN CNA2004100013328A patent/CN1511823A/zh active Pending
- 1999-12-24 WO PCT/JP1999/007284 patent/WO2001010812A1/ja active IP Right Grant
- 1999-12-24 KR KR1020067019510A patent/KR100740059B1/ko active IP Right Grant
- 1999-12-24 KR KR1020067019511A patent/KR100740060B1/ko active IP Right Grant
- 1999-12-24 CA CA002318761A patent/CA2318761A1/en not_active Abandoned
- 1999-12-24 KR KR1020007009039A patent/KR100701842B1/ko active IP Right Grant
- 1999-12-24 DE DE69920025T patent/DE69920025T2/de not_active Expired - Lifetime
- 1999-12-24 CN CNA2004100013313A patent/CN1511821A/zh active Pending
- 1999-12-24 CN CNB998114219A patent/CN1195727C/zh not_active Expired - Lifetime
- 1999-12-24 EP EP99961372A patent/EP1120394B1/en not_active Expired - Lifetime
- 1999-12-24 ID IDW20001563A patent/ID26736A/id unknown
-
2000
- 2000-01-03 TW TW089100024A patent/TW506968B/zh not_active IP Right Cessation
-
2002
- 2002-02-19 HK HK02101199.5A patent/HK1040236A1/zh unknown
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2003
- 2003-07-18 US US10/623,002 patent/US7193104B2/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
KR20060107858A (ko) | 2006-10-16 |
EP1120394A1 (en) | 2001-08-01 |
HK1040236A1 (zh) | 2002-05-31 |
CN1320113A (zh) | 2001-10-31 |
DE69920025D1 (de) | 2004-10-14 |
CA2318761A1 (en) | 2001-02-04 |
KR100740059B1 (ko) | 2007-07-16 |
AU1800500A (en) | 2001-03-05 |
KR100740060B1 (ko) | 2007-07-16 |
ID26736A (id) | 2001-02-08 |
CN1511823A (zh) | 2004-07-14 |
KR20060107859A (ko) | 2006-10-16 |
KR20010086254A (ko) | 2001-09-10 |
US20040019234A1 (en) | 2004-01-29 |
US7193104B2 (en) | 2007-03-20 |
EP1120394A4 (en) | 2002-07-24 |
KR100701842B1 (ko) | 2007-04-02 |
ES2228142T3 (es) | 2005-04-01 |
CN1511821A (zh) | 2004-07-14 |
ATE275538T1 (de) | 2004-09-15 |
TW506968B (en) | 2002-10-21 |
US6630601B1 (en) | 2003-10-07 |
WO2001010812A1 (fr) | 2001-02-15 |
AU764053B2 (en) | 2003-08-07 |
DE69920025T2 (de) | 2005-09-08 |
EP1120394B1 (en) | 2004-09-08 |
WO2001010812A9 (fr) | 2001-04-26 |
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