CH425761A - Verfahren zum drucklosen Abbau von Polyäthylenterephthalat zu Dimethylterephthalat - Google Patents
Verfahren zum drucklosen Abbau von Polyäthylenterephthalat zu DimethylterephthalatInfo
- Publication number
- CH425761A CH425761A CH928363A CH928363A CH425761A CH 425761 A CH425761 A CH 425761A CH 928363 A CH928363 A CH 928363A CH 928363 A CH928363 A CH 928363A CH 425761 A CH425761 A CH 425761A
- Authority
- CH
- Switzerland
- Prior art keywords
- aerosol
- polyethylene terephthalate
- methanol
- reaction
- dependent
- Prior art date
Links
- -1 polyethylene terephthalate Polymers 0.000 title claims description 42
- 229920000139 polyethylene terephthalate Polymers 0.000 title claims description 39
- 239000005020 polyethylene terephthalate Substances 0.000 title claims description 38
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 21
- 238000006731 degradation reaction Methods 0.000 title claims description 8
- 230000015556 catabolic process Effects 0.000 title claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 96
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 239000000443 aerosol Substances 0.000 claims description 27
- 239000000843 powder Substances 0.000 claims description 17
- 239000007795 chemical reaction product Substances 0.000 claims description 15
- 239000011261 inert gas Substances 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 9
- 239000002245 particle Substances 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- 238000001640 fractional crystallisation Methods 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- 150000003752 zinc compounds Chemical class 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 6
- 239000000470 constituent Substances 0.000 claims 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000007789 gas Substances 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 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
- 239000004135 Bone phosphate Substances 0.000 description 1
- 229910001208 Crucible steel Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 238000002074 melt spinning Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
Classifications
-
- 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
- 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
- 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
- C08J11/14—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 steam or water
-
- 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)
- Polyesters Or Polycarbonates (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEV22920A DE1169915B (de) | 1962-08-17 | 1962-08-17 | Verfahren zum Abbau von Polyaethylen-terephthalat zu Dimethylterephthalat |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH425761A true CH425761A (de) | 1966-12-15 |
Family
ID=7580187
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH928363A CH425761A (de) | 1962-08-17 | 1963-07-25 | Verfahren zum drucklosen Abbau von Polyäthylenterephthalat zu Dimethylterephthalat |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3321510A (en, 2012) |
| AT (1) | AT243252B (en, 2012) |
| BE (1) | BE635706A (en, 2012) |
| CH (1) | CH425761A (en, 2012) |
| DE (1) | DE1169915B (en, 2012) |
| GB (1) | GB976073A (en, 2012) |
| NL (2) | NL136399C (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0484963A3 (en) * | 1990-11-09 | 1992-10-21 | E.I. Du Pont De Nemours And Company | Recovery of methyl esters of aromatic acids and glycols from thermoplastic polyester scrap |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5051528A (en) * | 1990-04-24 | 1991-09-24 | Eastman Kodak Company | Recovery process for ethylene glycol and dimethylterephthalate |
| DE4227299C1 (de) * | 1992-08-18 | 1994-01-27 | Hoechst Ag | Verfahren zur Herstellung von monomeren Terephthalsäurediestern und Diolen aus Polyestern |
| US5298530A (en) * | 1992-11-25 | 1994-03-29 | Eastman Kodak Company | Process of recovering components from scrap polyester |
| US5498749A (en) * | 1993-10-22 | 1996-03-12 | Eastman Chemical Company | Process for separating cyclohexane dimethanol from dimethyl terephthalate |
| US5414106A (en) * | 1994-02-14 | 1995-05-09 | Hoechst Celanese Corporation | Process for recovering dimethyl terephthalate |
| US5414022A (en) * | 1994-03-10 | 1995-05-09 | Eastman Kodak Company | Process of recovering components from polyester resins |
| US5532404A (en) * | 1994-05-27 | 1996-07-02 | E. I. Du Pont De Nemours And Company | Monomer recovery process for contaminated polymers |
| US5710315A (en) * | 1994-05-27 | 1998-01-20 | E. I. Du Pont De Nemours And Company | Monomer recovery process for contaminated polymers |
| US5414107A (en) * | 1994-07-20 | 1995-05-09 | Hoechst Celanese Corporation | Process for recycling polyethylene terephthalate process residues containing alkali metal organic salts |
| US5765728A (en) * | 1995-03-27 | 1998-06-16 | Eastman Kodak Company | Method and apparatus for feeding chopped polyester scrap |
| US5502239A (en) * | 1995-08-07 | 1996-03-26 | Hoechst Celanese Corporation | Process for recovering dimethyl terephthalate |
| US5744503A (en) * | 1996-02-01 | 1998-04-28 | Hoechst Celanese Corporation | Recycling polyester and recovering glycols |
| US6136869A (en) * | 1997-10-17 | 2000-10-24 | Eastman Chemical Company | Depolymerization process for recycling polyesters |
| US6472557B1 (en) | 1999-02-10 | 2002-10-29 | Eastman Chemical Company | Process for recycling polyesters |
| US6919383B2 (en) * | 2001-04-10 | 2005-07-19 | North Carolina State University | CO2-assisted deploymerization, purification and recycling of step-growth polymers |
| US20050054757A1 (en) * | 2003-09-10 | 2005-03-10 | Pearson Jason Clay | Method for reducing the acetaldehyde level in polyesters |
| EP1802680A4 (en) * | 2004-10-18 | 2008-09-17 | Phoenix Technologies Int | PROCESS FOR ACCELERATING SOLIDIFICATION OF POLYETHYLENE TEREPHTHALATE |
| RU2384592C1 (ru) * | 2008-11-27 | 2010-03-20 | Учреждение Российской Академии Наук Институт Общей И Неорганической Химии Им. Н.С. Курнакова Ран (Ионх Ран) | Способ переработки отходов полиэтилентерефталата в порошкообразный продукт |
| US8966783B2 (en) * | 2010-07-29 | 2015-03-03 | Tanabe Engineering Corporation | Vacuum-pressure spray-drying method and vacuum-pressure spray-drying device |
| US9458354B2 (en) | 2010-10-06 | 2016-10-04 | Resinate Technologies, Inc. | Polyurethane dispersions and methods of making and using same |
| JP2014520008A (ja) | 2011-06-10 | 2014-08-21 | フェリス、クリストファー、エム． | 透明アクリルコーティング |
| US10000588B2 (en) | 2011-07-28 | 2018-06-19 | Eastman Chemical Company | Coating for the inner surface of plastic bottles for protection against degradation from volatile organic compounds |
| US20130029068A1 (en) | 2011-07-28 | 2013-01-31 | Eastman Chemical Company | Extrusion blow molded articles |
| WO2013025186A1 (en) | 2011-08-12 | 2013-02-21 | Eastman Chemical Company | Process for the preparation of polyesters with high recycle content |
| US12071519B2 (en) | 2017-09-15 | 2024-08-27 | 9449710 Canada Inc. | Terephthalic acid esters formation |
| US10808096B2 (en) | 2018-06-25 | 2020-10-20 | 9449710 Canada Inc. | Terephthalic acid esters formation |
| KR20220041177A (ko) | 2019-07-29 | 2022-03-31 | 이스트만 케미칼 컴파니 | 열분해 및 가메탄올분해로부터의 재활용된 단량체를 갖는 폴리에스테르의 제조 방법 |
| EP4048727A1 (en) | 2019-10-25 | 2022-08-31 | Eastman Chemical Company | Crystallizable shrinkable films and thermoformable films and sheets made from reactor grade resins with recycled content |
| WO2021126936A1 (en) | 2019-12-19 | 2021-06-24 | Eastman Chemical Company | Process for treating polyester methanolysis depolymerization product streams |
| EP4077267B1 (en) | 2019-12-19 | 2024-11-27 | Eastman Chemical Company | Method for producing dimethyl terephthalate from polyester methanolysis depolymerization systems |
| KR20220119656A (ko) | 2019-12-19 | 2022-08-30 | 이스트만 케미칼 컴파니 | 재활용물을 갖는 폴리에스터의 제조 방법 |
| EP4077263A1 (en) | 2019-12-20 | 2022-10-26 | Eastman Chemical Company | Catalysts for pet methanolysis |
| BR112022014929A2 (pt) * | 2020-02-10 | 2022-09-27 | Eastman Chem Co | Método para processar plástico residual, e, composição de coproduto de solvólise |
| EP4413066A1 (en) | 2021-10-06 | 2024-08-14 | Eastman Chemical Company | Production of virgin-quality pet and copolyester raw materials from polyester carpet fibers |
| WO2023076209A1 (en) | 2021-10-25 | 2023-05-04 | Eastman Chemical Company | Processes for recovering dialkyl terephthalates from tetramethyl cyclobutanediol (tmcd)-containing polymers |
| EP4437029A1 (en) | 2021-11-22 | 2024-10-02 | Eastman Chemical Company | Recyclable copolyesters articles with living hinges |
| US20250002642A1 (en) | 2021-11-22 | 2025-01-02 | Eastman Chemical Company | Process for making recyclable copolyesters articles with living hinges |
| WO2023091544A1 (en) | 2021-11-22 | 2023-05-25 | Eastman Chemical Company | Process for making recyclable copolyesters articles with living hinges |
| EP4436891A1 (en) | 2021-11-22 | 2024-10-02 | Eastman Chemical Company | Recyclable copolyesters articles with living hinges |
| EP4273190A1 (en) | 2022-05-03 | 2023-11-08 | Universität Hamburg | Method for the depolymerization of a terephthalate polyester |
| LU102949B1 (en) | 2022-05-03 | 2023-11-06 | Univ Hamburg | Method for the depolymerization of a terephthalate polyester |
| CN115353904B (zh) * | 2022-08-02 | 2024-02-23 | 中国矿业大学 | 一种过热蒸汽体系高效液化塑料垃圾制油的方法及其装置 |
| WO2024220458A1 (en) | 2023-04-19 | 2024-10-24 | Eastman Chemical Company | Copolyester compositions for recyclable heavy gauge sheet articles |
| WO2024220454A1 (en) | 2023-04-19 | 2024-10-24 | Eastman Chemical Company | Copolyester compositions for recyclable heavy gauge sheet articles |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3148208A (en) * | 1964-09-08 | Process for recovery of dimethyl | ||
| US3037050A (en) * | 1955-08-05 | 1962-05-29 | Glanzstoff Ag | Regeneration of terephthalic acid dimethyl ester from polyethylene terephthalate |
| DE1131202B (de) * | 1961-01-12 | 1962-06-14 | Glanzstoff Ag | Verfahren zum Abbau von Polyaethylenterephthalat zu Terephthalsaeuredimethylester |
-
0
- NL NL296330D patent/NL296330A/xx unknown
- NL NL136399D patent/NL136399C/xx active
- BE BE635706D patent/BE635706A/fr unknown
-
1962
- 1962-08-17 DE DEV22920A patent/DE1169915B/de active Pending
-
1963
- 1963-07-25 CH CH928363A patent/CH425761A/de unknown
- 1963-08-06 AT AT634063A patent/AT243252B/de active
- 1963-08-07 US US30070163 patent/US3321510A/en not_active Expired - Lifetime
- 1963-08-16 GB GB3254263A patent/GB976073A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0484963A3 (en) * | 1990-11-09 | 1992-10-21 | E.I. Du Pont De Nemours And Company | Recovery of methyl esters of aromatic acids and glycols from thermoplastic polyester scrap |
Also Published As
| Publication number | Publication date |
|---|---|
| BE635706A (en, 2012) | |
| DE1169915B (de) | 1964-05-14 |
| US3321510A (en) | 1967-05-23 |
| AT243252B (de) | 1965-11-10 |
| NL296330A (en, 2012) | 1900-01-01 |
| GB976073A (en, 2012) | 1964-11-25 |
| NL136399C (en, 2012) | 1900-01-01 |
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