JP3341912B2 - テレフタル酸の製法 - Google Patents
テレフタル酸の製法Info
- Publication number
- JP3341912B2 JP3341912B2 JP17993A JP17993A JP3341912B2 JP 3341912 B2 JP3341912 B2 JP 3341912B2 JP 17993 A JP17993 A JP 17993A JP 17993 A JP17993 A JP 17993A JP 3341912 B2 JP3341912 B2 JP 3341912B2
- Authority
- JP
- Japan
- Prior art keywords
- terephthalic acid
- polyalkylene terephthalate
- reaction
- hydrolysis
- hydrolysis reaction
- 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
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title claims abstract description 319
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 103
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 90
- 238000000034 method Methods 0.000 claims abstract description 70
- 229920001283 Polyalkylene terephthalate Polymers 0.000 claims abstract description 69
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 55
- 239000000203 mixture Substances 0.000 claims abstract description 42
- 230000007062 hydrolysis Effects 0.000 claims abstract description 36
- -1 alkylene glycol Chemical compound 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
- 239000007790 solid phase Substances 0.000 claims abstract description 28
- 238000010438 heat treatment Methods 0.000 claims abstract description 15
- 239000002245 particle Substances 0.000 claims description 41
- 239000000243 solution Substances 0.000 claims description 28
- 239000007787 solid Substances 0.000 claims description 27
- 239000012736 aqueous medium Substances 0.000 claims description 26
- 239000011541 reaction mixture Substances 0.000 claims description 14
- 239000011343 solid material Substances 0.000 claims description 13
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 238000000227 grinding Methods 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 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 2
- 238000001953 recrystallisation Methods 0.000 abstract description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 26
- 229920000139 polyethylene terephthalate Polymers 0.000 description 26
- 238000003756 stirring Methods 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- 239000012535 impurity Substances 0.000 description 14
- 238000005406 washing Methods 0.000 description 13
- 238000002474 experimental method Methods 0.000 description 11
- 239000004800 polyvinyl chloride Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229920000915 polyvinyl chloride Polymers 0.000 description 10
- 239000000460 chlorine Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 8
- 229910021641 deionized water Inorganic materials 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 6
- 238000004140 cleaning Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 238000013019 agitation Methods 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000013213 extrapolation Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 238000003921 particle size analysis Methods 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 235000004869 Tussilago farfara Nutrition 0.000 description 1
- 240000000377 Tussilago farfara Species 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- VIQSRHWJEKERKR-UHFFFAOYSA-L disodium;terephthalate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 VIQSRHWJEKERKR-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000003947 neutron activation analysis Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- 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
- 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)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Biological Depolymerization Polymers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9200176A GB9200176D0 (en) | 1992-01-07 | 1992-01-07 | Process for the production of terephthalic acid |
| GB9200176.7 | 1992-01-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05255182A JPH05255182A (ja) | 1993-10-05 |
| JP3341912B2 true JP3341912B2 (ja) | 2002-11-05 |
Family
ID=10708157
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17993A Expired - Fee Related JP3341912B2 (ja) | 1992-01-07 | 1993-01-05 | テレフタル酸の製法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5426217A (OSRAM) |
| EP (1) | EP0550979B1 (OSRAM) |
| JP (1) | JP3341912B2 (OSRAM) |
| AT (1) | ATE158273T1 (OSRAM) |
| BR (1) | BR9300024A (OSRAM) |
| DE (1) | DE69222285T2 (OSRAM) |
| DK (1) | DK0550979T3 (OSRAM) |
| ES (1) | ES2106836T3 (OSRAM) |
| GB (2) | GB9200176D0 (OSRAM) |
| GR (1) | GR3024869T3 (OSRAM) |
| TW (1) | TW267160B (OSRAM) |
| ZA (1) | ZA9210084B (OSRAM) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5504121A (en) * | 1992-05-18 | 1996-04-02 | Swig Pty Ltd. | Polyethylene terephthalate decontamination |
| US5602187A (en) * | 1992-05-18 | 1997-02-11 | Swig Pty Ltd. | Polyethylene terephthalate decontamination |
| US5750776A (en) * | 1993-07-05 | 1998-05-12 | Imperial Chemical Industries Plc | Production of dicarboxylic acids or esters thereof |
| US5580905A (en) * | 1994-04-28 | 1996-12-03 | United Resource Recovery Corporation | Process for recycling polyesters |
| US5502247A (en) * | 1994-11-17 | 1996-03-26 | Amoco Corporation | Process for recovery of aromatic acid or ester and polyol from waste polyester resins |
| US5958987A (en) * | 1996-04-10 | 1999-09-28 | The Coca-Cola Company | Process for separating polyester from other materials |
| RS3604A (sr) | 2001-06-19 | 2007-04-10 | United Resource Recovery Corporation, | Postupak za odvajanje poliestera od drugih materijala |
| US7098299B1 (en) | 2005-03-16 | 2006-08-29 | United Resource Recovery Corporation | Separation of contaminants from polyester materials |
| US20090099388A1 (en) * | 2006-04-03 | 2009-04-16 | Hussain Al Ghatta | Recovery of aromatic dicarboxylic acids from waste polyester resin in the presence of a polyamide |
| BRPI0621743A2 (pt) * | 2006-06-21 | 2011-12-20 | Cobarr Spa | recuperação de ácidos dicarboxìlicos aromáticos a partir de resìduos de resina de poliéster |
| DE102007025945B3 (de) * | 2007-06-04 | 2009-01-02 | Far East University | Tandemfahrrad mit mehreren Fahrweisen |
| DE102008007791B4 (de) * | 2008-02-06 | 2013-02-21 | Söhnke Kleiner | Vorrichtung und verbessertes Verfahren zur wässrigen Verkohlung / hydrothermalen Karbonisierung von Biomasse sowie dadurch erhaltene Karbonisierungsprodukte |
| JP2016124841A (ja) * | 2015-01-06 | 2016-07-11 | 日東電工株式会社 | テレフタル酸の製造方法および再生ポリエチレンテレフタレートの製造方法 |
| CN116323547A (zh) * | 2021-07-19 | 2023-06-23 | 株式会社Lg化学 | 用于合成再生塑料的单体组合物、其制备方法、使用其的再生塑料、模制品、增塑剂组合物 |
| JP2025510233A (ja) * | 2022-03-24 | 2025-04-14 | イネオス ユーエス ケミカルズ カンパニー | 芳香族ジカルボン酸を製造する方法及び装置 |
| WO2023250158A2 (en) | 2022-06-24 | 2023-12-28 | Hybridworks Chemical, Llc | Polyester-cotton blend textile recycling process and system with rotating hydrolysis reactor |
| JP7829937B2 (ja) * | 2023-05-25 | 2026-03-16 | ＡＣ Ｂｉｏｄｅ株式会社 | ポリエステル樹脂の分解方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1130695A (en) | 1966-04-18 | 1968-10-16 | Hercules Inc | Production of terephthalic acid by hydrolysis of an alkyl terephthalate |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE14854C (de) * | M. M. goldenstein & COMP, in Wien | Mauerkonservator zum Befestigen und Aufhängen von Karniefsen, Spiegeln, Bildern u. dgl | ||
| GB2123403A (en) * | 1982-07-09 | 1984-02-01 | Celanese Mexicana Sa | Continuous procedure for obtaining pure terephthalic acid and glycol starting from polyethylene terephthalate waste |
| US4620032A (en) * | 1984-12-11 | 1986-10-28 | Celanese Corporation | Depolymerization of condensation polymers involving a pre-molecular weight reduction step |
| US4578510A (en) * | 1984-12-11 | 1986-03-25 | Celanese Corporation | Process for minimizing formation of low molecular weight oligomers during hydrolytic depolymerization of condensation polymers |
| US5095145A (en) * | 1990-11-05 | 1992-03-10 | Amoco Corporation | Preparation of purified terephthalic acid from waste polyethylene terephthalate |
-
1992
- 1992-01-07 GB GB9200176A patent/GB9200176D0/en active Pending
- 1992-11-15 GB GB9226106A patent/GB9226106D0/en active Pending
- 1992-12-15 DK DK92311421T patent/DK0550979T3/da active
- 1992-12-15 AT AT92311421T patent/ATE158273T1/de not_active IP Right Cessation
- 1992-12-15 ES ES92311421T patent/ES2106836T3/es not_active Expired - Lifetime
- 1992-12-15 DE DE69222285T patent/DE69222285T2/de not_active Expired - Fee Related
- 1992-12-15 EP EP19920311421 patent/EP0550979B1/en not_active Expired - Lifetime
- 1992-12-22 TW TW81110279A patent/TW267160B/zh active
- 1992-12-29 ZA ZA9210084A patent/ZA9210084B/xx unknown
-
1993
- 1993-01-05 JP JP17993A patent/JP3341912B2/ja not_active Expired - Fee Related
- 1993-01-06 BR BR9300024A patent/BR9300024A/pt not_active IP Right Cessation
- 1993-01-06 US US08/001,548 patent/US5426217A/en not_active Expired - Lifetime
-
1997
- 1997-09-26 GR GR970402514T patent/GR3024869T3/el unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1130695A (en) | 1966-04-18 | 1968-10-16 | Hercules Inc | Production of terephthalic acid by hydrolysis of an alkyl terephthalate |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0550979A2 (en) | 1993-07-14 |
| DE69222285D1 (de) | 1997-10-23 |
| BR9300024A (pt) | 1993-07-13 |
| DE69222285T2 (de) | 1998-01-22 |
| GB9200176D0 (en) | 1992-02-26 |
| GB9226106D0 (en) | 1993-02-10 |
| US5426217A (en) | 1995-06-20 |
| TW267160B (OSRAM) | 1996-01-01 |
| GR3024869T3 (en) | 1998-01-30 |
| ES2106836T3 (es) | 1997-11-16 |
| ATE158273T1 (de) | 1997-10-15 |
| ZA9210084B (en) | 1993-09-27 |
| EP0550979A3 (en) | 1993-09-08 |
| JPH05255182A (ja) | 1993-10-05 |
| DK0550979T3 (da) | 1998-05-11 |
| EP0550979B1 (en) | 1997-09-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
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| R250 | Receipt of annual fees |
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| FPAY | Renewal fee payment (event date is renewal date of database) |
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| LAPS | Cancellation because of no payment of annual fees |