DE1243684B - Kontinuierliches Verfahren zum Entpolymerisieren hochmolekularer, polymerer Ester aus gesaettigten aliphatischen, cycloaliphatischen oder aromatischen Dicarbonsaeuren und zweiwertigen Alkoholen - Google Patents
Kontinuierliches Verfahren zum Entpolymerisieren hochmolekularer, polymerer Ester aus gesaettigten aliphatischen, cycloaliphatischen oder aromatischen Dicarbonsaeuren und zweiwertigen AlkoholenInfo
- Publication number
- DE1243684B DE1243684B DEP33149A DEP0033149A DE1243684B DE 1243684 B DE1243684 B DE 1243684B DE P33149 A DEP33149 A DE P33149A DE P0033149 A DEP0033149 A DE P0033149A DE 1243684 B DE1243684 B DE 1243684B
- Authority
- DE
- Germany
- Prior art keywords
- molecular weight
- temperature
- reactor
- depolymerization
- liquid
- 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
- -1 aromatic dicarboxylic acids Chemical class 0.000 title claims description 33
- 150000002148 esters Chemical class 0.000 title claims description 14
- 125000001931 aliphatic group Chemical group 0.000 title claims description 6
- 150000001298 alcohols Chemical class 0.000 title claims description 5
- 238000010924 continuous production Methods 0.000 title claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 71
- 239000007788 liquid Substances 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- KKEYFWRCBNTPAC-UHFFFAOYSA-N terephthalic acid group Chemical group C(C1=CC=C(C(=O)O)C=C1)(=O)O KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- 238000009835 boiling Methods 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 34
- 229920000139 polyethylene terephthalate Polymers 0.000 description 24
- 239000005020 polyethylene terephthalate Substances 0.000 description 24
- 239000000178 monomer Substances 0.000 description 22
- 229920000728 polyester Polymers 0.000 description 20
- 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 17
- 239000000047 product Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 14
- 238000007710 freezing Methods 0.000 description 13
- 230000008014 freezing Effects 0.000 description 13
- 239000012263 liquid product Substances 0.000 description 8
- 238000003860 storage Methods 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 238000006068 polycondensation reaction Methods 0.000 description 6
- XRBXGZZMKCBTFP-UHFFFAOYSA-N 4-(2,2-dihydroxyethoxycarbonyl)benzoic acid Chemical compound OC(O)COC(=O)C1=CC=C(C(O)=O)C=C1 XRBXGZZMKCBTFP-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 5
- 239000002699 waste material Substances 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000002310 reflectometry Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- 208000001840 Dandruff Diseases 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- XFQHIELVPOKJIM-UHFFFAOYSA-N 1,4-dioxacyclotetradecane-5,14-dione Chemical compound O=C1CCCCCCCCC(=O)OCCO1 XFQHIELVPOKJIM-UHFFFAOYSA-N 0.000 description 2
- QABJRPWOBYCMBO-UHFFFAOYSA-N 1,4-dioxacyclotridecane-5,13-dione Chemical compound O=C1CCCCCCCC(=O)OCCO1 QABJRPWOBYCMBO-UHFFFAOYSA-N 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 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 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 230000007257 malfunction Effects 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 150000003503 terephthalic acid derivatives Chemical class 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000002706 hydrostatic effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000013138 pruning Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- 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
- 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
- C08G63/785—Preparation processes characterised by the apparatus used
-
- 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
-
- 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
- C08J2361/00—Characterised by the use of condensation polymers of aldehydes or ketones; Derivatives of such polymers
- C08J2361/02—Condensation polymers of aldehydes or ketones only
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Sustainable Development (AREA)
- Polyesters Or Polycarbonates (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US242790A US3257335A (en) | 1962-12-06 | 1962-12-06 | Two-stage process for depolymerizing polyesters |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1243684B true DE1243684B (de) | 1967-07-06 |
Family
ID=22916193
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEP33149A Pending DE1243684B (de) | 1962-12-06 | 1963-12-06 | Kontinuierliches Verfahren zum Entpolymerisieren hochmolekularer, polymerer Ester aus gesaettigten aliphatischen, cycloaliphatischen oder aromatischen Dicarbonsaeuren und zweiwertigen Alkoholen |
Country Status (7)
Country | Link |
---|---|
US (1) | US3257335A (en, 2012) |
BE (1) | BE640836A (en, 2012) |
DE (1) | DE1243684B (en, 2012) |
FR (1) | FR1386373A (en, 2012) |
GB (1) | GB1012652A (en, 2012) |
LU (1) | LU44949A1 (en, 2012) |
NL (1) | NL301426A (en, 2012) |
Families Citing this family (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1495251B2 (de) * | 1961-10-12 | 1976-12-02 | Hoechst Ag, 6000 Frankfurt | Verfahren zur aufarbeitung von abfaellen von schwerloeslichen, hochmolekularen terephthalsaeurediolestern |
US3446758A (en) * | 1966-01-12 | 1969-05-27 | Goodyear Tire & Rubber | Thermosettable resin from preformed linear polyester and a polyhydric alcohol |
US4054561A (en) * | 1975-01-27 | 1977-10-18 | Owens-Corning Fiberglas Corporation | Thermoplastic additives for molding compounds |
US4096102A (en) * | 1975-01-27 | 1978-06-20 | Owens-Corning Fiberglas Corporation | Moldable compositions comprising thermosetting polyester resin and thermoplastic resin |
US4138374A (en) * | 1978-02-03 | 1979-02-06 | E. I. Du Pont De Nemours And Company | Process for manufacturing shaped polyester article using scrap materials |
US4711912A (en) * | 1982-04-29 | 1987-12-08 | The Celotex Corporation | Polyisocyanurate foams from digestion products of polyalkylene terephthalate polymers and polyols |
US4873268A (en) * | 1984-02-22 | 1989-10-10 | Sloss Industries Corporation | Digestion products of polyalkylene terephthalate polymers and polycarboxylic acid-containing polyols and polymeric foams obtained therefrom |
US4539341A (en) * | 1984-02-22 | 1985-09-03 | Jim Walter Resources, Inc. | Digestion products of polyalkylene terephthalate polymers and polycarboxylic acid-containing polyols and polymeric foams obtained therefrom |
JPS60248646A (ja) * | 1984-05-25 | 1985-12-09 | Toray Ind Inc | ポリエステル屑の解重合方法 |
US4559370A (en) * | 1984-05-25 | 1985-12-17 | Blanpied Robert H | Copolyester polyol resins, polyol blends comprising the same, and resultant polyisocyanurate foams |
US5236959A (en) * | 1992-03-12 | 1993-08-17 | Hoechst Celanese Corporation | Process for recycling polyester/cotton blends |
US5602187A (en) * | 1992-05-18 | 1997-02-11 | Swig Pty Ltd. | Polyethylene terephthalate decontamination |
US5504121A (en) * | 1992-05-18 | 1996-04-02 | Swig Pty Ltd. | Polyethylene terephthalate decontamination |
PL181832B1 (pl) * | 1992-05-18 | 2001-09-28 | Swig Pty Ltd | Sposób odzyskiwania oczyszczonych komponentów politereftalanu etylenu z materialu zawierajacego zanieczyszczony politereftalan etylenu§ PL PL PL PL PL PL PL PL |
DE4227299C1 (de) * | 1992-08-18 | 1994-01-27 | Hoechst Ag | Verfahren zur Herstellung von monomeren Terephthalsäurediestern und Diolen aus Polyestern |
EP0707562B1 (en) * | 1993-07-05 | 2000-04-26 | E.I. Du Pont De Nemours And Company | Production of dicarboxylic acids |
US5380793A (en) * | 1993-07-13 | 1995-01-10 | Ashland Oil, Inc. | Styrene soluble unsatured polyester resin from polyethylene terephthalate |
TW330940B (en) * | 1993-12-22 | 1998-05-01 | Mitsui Petroleum Chemicals Ind | A method of manufacturing polyesters |
EP0749456A1 (en) * | 1994-03-11 | 1996-12-27 | Monsanto Company | Copolymers of recycled polyesters |
US5395858A (en) * | 1994-04-28 | 1995-03-07 | Partek, Inc. | Process for recycling polyester |
US5580905A (en) * | 1994-04-28 | 1996-12-03 | United Resource Recovery Corporation | Process for recycling polyesters |
IT1278166B1 (it) * | 1995-01-24 | 1997-11-17 | Ars Ing Srl | Processo per la preparazione di bis (2-idrossietil) teraftalato |
US5635584A (en) * | 1995-12-07 | 1997-06-03 | Eastman Chemical Company | Process including glycolysis and subsequent purification for recycling polyester materials |
US5756554A (en) * | 1996-02-02 | 1998-05-26 | Ashland Inc. | Low profile additives for polyester resin systems based on asymmetric glycols and aromatic diacids |
US5958987A (en) * | 1996-04-10 | 1999-09-28 | The Coca-Cola Company | Process for separating polyester from other materials |
US5821381A (en) * | 1997-02-03 | 1998-10-13 | Eastman Kodak Company | Low pressure process for purifying crude polyester by sublimation |
US5712410A (en) * | 1997-03-03 | 1998-01-27 | Eastman Kodak Company | Gas phase crystallization of dimethyl terephthalate |
IL159457A0 (en) * | 2001-06-19 | 2004-06-01 | United Resource Recovery Corp | Process for separating polyester from other materials |
US20030134915A1 (en) * | 2001-12-17 | 2003-07-17 | Scantlebury Geoffrey Raymond | Production of transparent polyester using waste |
US7098299B1 (en) * | 2005-03-16 | 2006-08-29 | United Resource Recovery Corporation | Separation of contaminants from polyester materials |
US9458354B2 (en) | 2010-10-06 | 2016-10-04 | Resinate Technologies, Inc. | Polyurethane dispersions and methods of making and using same |
EP2520601A1 (en) | 2011-05-05 | 2012-11-07 | Cytec Surface Specialties, S.A. | Process for producing polyesters |
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 |
WO2013025186A1 (en) | 2011-08-12 | 2013-02-21 | Eastman Chemical Company | Process for the preparation of polyesters with high recycle content |
KR20220041177A (ko) | 2019-07-29 | 2022-03-31 | 이스트만 케미칼 컴파니 | 열분해 및 가메탄올분해로부터의 재활용된 단량체를 갖는 폴리에스테르의 제조 방법 |
WO2023076209A1 (en) | 2021-10-25 | 2023-05-04 | Eastman Chemical Company | Processes for recovering dialkyl terephthalates from tetramethyl cyclobutanediol (tmcd)-containing polymers |
DE102021212695A1 (de) | 2021-11-11 | 2023-05-11 | Thyssenkrupp Ag | Vorrichtung und verfahren zur herstellung eines polyester-depolymerisats sowie vorrichtung und verfahren zur herstellung eines polyesters |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA490032A (en) * | 1953-01-27 | Lewis Heath Royden | Degradation of aromatic polyesters |
-
0
- NL NL301426D patent/NL301426A/xx unknown
-
1962
- 1962-12-06 US US242790A patent/US3257335A/en not_active Expired - Lifetime
-
1963
- 1963-12-05 LU LU44949D patent/LU44949A1/xx unknown
- 1963-12-05 BE BE640836D patent/BE640836A/xx unknown
- 1963-12-06 FR FR956260A patent/FR1386373A/fr not_active Expired
- 1963-12-06 GB GB48381/63A patent/GB1012652A/en not_active Expired
- 1963-12-06 DE DEP33149A patent/DE1243684B/de active Pending
Also Published As
Publication number | Publication date |
---|---|
LU44949A1 (en, 2012) | 1964-06-05 |
US3257335A (en) | 1966-06-21 |
FR1386373A (fr) | 1965-01-22 |
BE640836A (en, 2012) | 1964-06-05 |
NL301426A (en, 2012) | |
GB1012652A (en) | 1965-12-08 |
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