CA2419422C - Polyester precursor purification process - Google Patents
Polyester precursor purification process Download PDFInfo
- Publication number
- CA2419422C CA2419422C CA002419422A CA2419422A CA2419422C CA 2419422 C CA2419422 C CA 2419422C CA 002419422 A CA002419422 A CA 002419422A CA 2419422 A CA2419422 A CA 2419422A CA 2419422 C CA2419422 C CA 2419422C
- Authority
- CA
- Canada
- Prior art keywords
- oligomer
- catalyst
- hydrogenation
- hydrogen
- terephthalic 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.)
- Expired - Fee Related
Links
- 229920000728 polyester Polymers 0.000 title claims abstract description 39
- 238000000746 purification Methods 0.000 title claims abstract description 11
- 239000002243 precursor Substances 0.000 title abstract description 5
- 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 74
- 238000000034 method Methods 0.000 claims abstract description 39
- 150000002009 diols Chemical class 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims description 59
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 54
- 238000005984 hydrogenation reaction Methods 0.000 claims description 43
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 32
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 29
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 14
- 238000006116 polymerization reaction Methods 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- -1 platinum group metals Chemical class 0.000 claims description 8
- 229910052697 platinum Inorganic materials 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- 239000000155 melt Substances 0.000 claims description 6
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 3
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 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
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
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- 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
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- 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
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- 239000002994 raw material Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 150000003503 terephthalic acid derivatives Chemical class 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 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
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- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
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- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 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 |
|---|---|---|---|
| US22869500P | 2000-08-29 | 2000-08-29 | |
| US60/228,695 | 2000-08-29 | ||
| US09/812,581 US6380352B1 (en) | 2000-08-29 | 2001-03-20 | Polyester precursor purification process |
| US09/812,581 | 2001-03-20 | ||
| PCT/US2001/026487 WO2002018471A2 (en) | 2000-08-29 | 2001-08-24 | Polyester precursor purification process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2419422A1 CA2419422A1 (en) | 2002-03-07 |
| CA2419422C true CA2419422C (en) | 2007-07-17 |
Family
ID=26922575
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002419422A Expired - Fee Related CA2419422C (en) | 2000-08-29 | 2001-08-24 | Polyester precursor purification process |
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 |
| 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 |
| DE60123810T2 (de) | 2007-03-01 |
| 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 |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |