CA1043947A - Apparatus and a continuous process for converting polyester wastes to dialkyl terephthalate - Google Patents
Apparatus and a continuous process for converting polyester wastes to dialkyl terephthalateInfo
- Publication number
- CA1043947A CA1043947A CA220,203A CA220203A CA1043947A CA 1043947 A CA1043947 A CA 1043947A CA 220203 A CA220203 A CA 220203A CA 1043947 A CA1043947 A CA 1043947A
- Authority
- CA
- Canada
- Prior art keywords
- solution
- liquid
- zone
- reaction zone
- reboiler
- 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
Links
- 239000002699 waste material Substances 0.000 title claims abstract description 46
- 229920000728 polyester Polymers 0.000 title claims abstract description 29
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 title claims description 19
- 238000010924 continuous production Methods 0.000 title abstract description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 131
- 150000002148 esters Chemical class 0.000 claims abstract description 58
- 239000003054 catalyst Substances 0.000 claims abstract description 41
- -1 polyethylene terephthalate Polymers 0.000 claims abstract description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000005020 polyethylene terephthalate Substances 0.000 claims abstract description 18
- 229920000139 polyethylene terephthalate Polymers 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 230000036961 partial effect Effects 0.000 claims abstract description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 75
- 239000000243 solution Substances 0.000 claims description 55
- 239000007788 liquid Substances 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 43
- 230000004888 barrier function Effects 0.000 claims description 19
- 239000003352 sequestering agent Substances 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000006193 liquid solution Substances 0.000 claims description 8
- 239000000376 reactant Substances 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 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 claims description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical group [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 239000004246 zinc acetate Substances 0.000 claims description 3
- 230000001174 ascending effect Effects 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000012263 liquid product Substances 0.000 claims description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract description 2
- 125000004185 ester group Chemical group 0.000 abstract 2
- 238000004064 recycling Methods 0.000 abstract 1
- 230000008016 vaporization Effects 0.000 abstract 1
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 62
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 58
- 229940093476 ethylene glycol Drugs 0.000 description 12
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 11
- 238000011084 recovery Methods 0.000 description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DJQMYWWZWUOCBQ-UHFFFAOYSA-N 4-o-(2-hydroxyethyl) 1-o-methyl benzene-1,4-dicarboxylate Chemical compound COC(=O)C1=CC=C(C(=O)OCCO)C=C1 DJQMYWWZWUOCBQ-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000012668 chain scission Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 230000002844 continuous effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 125000004990 dihydroxyalkyl group Chemical group 0.000 description 1
- OVPXRLUTUWRYEY-UHFFFAOYSA-N dimethyl naphthalene-1,8-dicarboxylate Chemical compound C1=CC(C(=O)OC)=C2C(C(=O)OC)=CC=CC2=C1 OVPXRLUTUWRYEY-UHFFFAOYSA-N 0.000 description 1
- BTVWZWFKMIUSGS-UHFFFAOYSA-N dimethylethyleneglycol Natural products CC(C)(O)CO BTVWZWFKMIUSGS-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- OYFJQPXVCSSHAI-QFPUQLAESA-N enalapril maleate Chemical compound OC(=O)\C=C/C(O)=O.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 OYFJQPXVCSSHAI-QFPUQLAESA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012527 feed solution Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 230000034659 glycolysis Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000005487 naphthalate group Chemical group 0.000 description 1
- 239000000615 nonconductor Substances 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229920006280 packaging film Polymers 0.000 description 1
- 239000012785 packaging film Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229940094537 polyester-10 Drugs 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000874 polytetramethylene terephthalate Polymers 0.000 description 1
- 230000003405 preventing effect Effects 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/24—Stationary reactors without moving elements inside
- B01J19/2415—Tubular reactors
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J4/00—Feed or outlet devices; Feed or outlet control devices
- B01J4/001—Feed or outlet devices as such, e.g. feeding tubes
- B01J4/004—Sparger-type elements
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00761—Details of the reactor
- B01J2219/00763—Baffles
- B01J2219/00765—Baffles attached to the reactor wall
- B01J2219/00777—Baffles attached to the reactor wall horizontal
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44290874A | 1974-02-15 | 1974-02-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1043947A true CA1043947A (en) | 1978-12-05 |
Family
ID=23758647
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA220,203A Expired CA1043947A (en) | 1974-02-15 | 1975-02-14 | Apparatus and a continuous process for converting polyester wastes to dialkyl terephthalate |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS50112330A (en, 2012) |
| BE (1) | BE825520A (en, 2012) |
| CA (1) | CA1043947A (en, 2012) |
| DE (1) | DE2506353A1 (en, 2012) |
| FR (1) | FR2261254B1 (en, 2012) |
| GB (1) | GB1458486A (en, 2012) |
| IT (1) | IT1031761B (en, 2012) |
| LU (1) | LU71855A1 (en, 2012) |
| NL (1) | NL7501735A (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR200458147Y1 (ko) * | 2008-11-10 | 2012-01-20 | 김철호 | 혁대 |
| CN112705124B (zh) * | 2019-10-25 | 2022-07-12 | 中国石油化工股份有限公司 | 用于合成碳酸酯的反应器、系统以及合成碳酸酯的方法 |
-
1975
- 1975-02-13 JP JP1752475A patent/JPS50112330A/ja active Pending
- 1975-02-14 NL NL7501735A patent/NL7501735A/xx not_active Application Discontinuation
- 1975-02-14 FR FR7504604A patent/FR2261254B1/fr not_active Expired
- 1975-02-14 IT IT2029675A patent/IT1031761B/it active
- 1975-02-14 GB GB627275A patent/GB1458486A/en not_active Expired
- 1975-02-14 CA CA220,203A patent/CA1043947A/en not_active Expired
- 1975-02-14 BE BE153345A patent/BE825520A/xx unknown
- 1975-02-14 LU LU71855A patent/LU71855A1/xx unknown
- 1975-02-14 DE DE19752506353 patent/DE2506353A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| BE825520A (fr) | 1975-08-14 |
| FR2261254A1 (en, 2012) | 1975-09-12 |
| FR2261254B1 (en, 2012) | 1978-12-29 |
| IT1031761B (it) | 1979-05-10 |
| DE2506353A1 (de) | 1975-08-21 |
| GB1458486A (en) | 1976-12-15 |
| NL7501735A (nl) | 1975-08-19 |
| JPS50112330A (en, 2012) | 1975-09-03 |
| LU71855A1 (en, 2012) | 1975-06-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3907868A (en) | Polyester waste recovery | |
| US4146729A (en) | Process for preparing poly(ethylene terephthalate) | |
| US4605762A (en) | Depolymerization of condensation polymers | |
| US5656757A (en) | Monomer recovery from multi-component materials | |
| EP0526572B1 (en) | Recovery of ethylene glycol and dimethyl terephthalate from polyethylene terephthalate | |
| US6262294B1 (en) | Process for continuously producing monomer components from aromatic polyester | |
| AU617767B2 (en) | Atmospheric pressure process for preparing pure cyclic esters | |
| US4289871A (en) | Method to increase reactor capacity for polycondensation of polyesters | |
| EP0724559B1 (en) | Process for separating cyclohexane dimethanol from dimethyl terephthalate | |
| US3185670A (en) | Pressure esterification | |
| AU640589B2 (en) | Purifying glycolide and lactides using high pressure gas stream | |
| US4254246A (en) | Column system process for polyester plants | |
| EP0662466B1 (en) | Continuous process for the recovery of terephthalic acid from waste or used products of polyalkylene terephthalate polymers | |
| CA1043947A (en) | Apparatus and a continuous process for converting polyester wastes to dialkyl terephthalate | |
| CA2396473C (en) | Continuous process for producing bis(3-hydroxypropyl) terephthalate | |
| US3963446A (en) | Apparatus for conducting a continuous chemical reaction with internal recycle | |
| JPS60163918A (ja) | ポリエステルの連続製造方法 | |
| EP0761713B1 (en) | Method for producing polyesters | |
| JP2002105185A (ja) | ポリエステルの製造方法 | |
| KR810001745B1 (ko) | 연속 직접 에스테르화 방법 | |
| WO2022139675A1 (en) | Process for the production of lactide | |
| CA1234569A (en) | Depolymerization of condensation polymers | |
| JP2003113125A (ja) | ポリエステルからモノマー製造方法 | |
| CA2183699A1 (en) | Method for producing polyesters |