CA1188708A - Continuous procedure for obtaining pure terephthalic acid and glycol starting from polyethylene terephthalate waste - Google Patents
Continuous procedure for obtaining pure terephthalic acid and glycol starting from polyethylene terephthalate wasteInfo
- Publication number
- CA1188708A CA1188708A CA000404984A CA404984A CA1188708A CA 1188708 A CA1188708 A CA 1188708A CA 000404984 A CA000404984 A CA 000404984A CA 404984 A CA404984 A CA 404984A CA 1188708 A CA1188708 A CA 1188708A
- Authority
- CA
- Canada
- Prior art keywords
- terephthalic acid
- glycol
- polyethylene terephthalate
- continuous method
- waste
- 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
- 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 88
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims abstract description 72
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 239000002699 waste material Substances 0.000 title claims abstract description 32
- -1 polyethylene terephthalate Polymers 0.000 title claims abstract description 29
- 239000005020 polyethylene terephthalate Substances 0.000 title claims abstract description 28
- 229920000139 polyethylene terephthalate Polymers 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title abstract description 24
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 27
- 230000007062 hydrolysis Effects 0.000 claims abstract description 26
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000011437 continuous method Methods 0.000 claims abstract description 18
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 17
- 238000001914 filtration Methods 0.000 claims abstract description 10
- 238000004821 distillation Methods 0.000 claims abstract description 6
- 230000007935 neutral effect Effects 0.000 claims abstract description 5
- 238000002425 crystallisation Methods 0.000 claims description 16
- 230000008025 crystallization Effects 0.000 claims description 16
- 239000013078 crystal Substances 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 238000001816 cooling Methods 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 239000004698 Polyethylene Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 229920000573 polyethylene Polymers 0.000 claims description 3
- 239000006228 supernatant Substances 0.000 claims description 3
- 238000013022 venting Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 238000010924 continuous production Methods 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 208000036366 Sensation of pressure Diseases 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 4
- 206010037660 Pyrexia Diseases 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 6
- 238000001179 sorption measurement Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 238000003795 desorption Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000004061 bleaching Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 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
- 238000002360 preparation method Methods 0.000 description 2
- 238000002203 pretreatment Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000007420 reactivation Effects 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229930002875 chlorophyll Natural products 0.000 description 1
- 235000019804 chlorophyll Nutrition 0.000 description 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 239000000049 pigment Substances 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
- 229920000728 polyester Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/095—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of organic acids
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MX18778581A MX157433A (es) | 1981-06-12 | 1981-06-12 | Procedimiento continuo para la obtencion de acido tereftalico y glicol puros,a partir de desperdicios de tereftalato de polietileno |
| MX187785 | 1981-06-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1188708A true CA1188708A (en) | 1985-06-11 |
Family
ID=19747646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000404984A Expired CA1188708A (en) | 1981-06-12 | 1982-06-11 | Continuous procedure for obtaining pure terephthalic acid and glycol starting from polyethylene terephthalate waste |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS584735A (enrdf_load_stackoverflow) |
| BR (1) | BR8203311A (enrdf_load_stackoverflow) |
| CA (1) | CA1188708A (enrdf_load_stackoverflow) |
| DE (1) | DE3221341A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2507595A1 (enrdf_load_stackoverflow) |
| MX (1) | MX157433A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6660236B1 (en) | 1998-11-30 | 2003-12-09 | Takeda Chemical Industries, Ltd. | Apparatus for decomposition and recovery of polyurethane resin |
| CN110950751A (zh) * | 2018-09-26 | 2020-04-03 | 远东新世纪股份有限公司 | 对苯二甲酸的制造方法及其系统 |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60163844A (ja) * | 1984-02-06 | 1985-08-26 | Mitsubishi Chem Ind Ltd | ジメチルテレフタレ−トの製造法 |
| FR2672049A1 (fr) * | 1991-01-30 | 1992-07-31 | Benzaria Jacques | Procede de fabrication de terephtalate de metal alcalin ou alcalino-terreux ou de l'acide terephilique de purete elevee. |
| JP3659717B2 (ja) | 1995-11-30 | 2005-06-15 | 株式会社神戸製鋼所 | 化学プラント内廃棄物の分解方法および装置 |
| DE19605474C2 (de) * | 1996-02-14 | 1997-12-18 | Ems Polyloy Gmbh | Verfahren zur Herstellung von teilaromatischen Copolyamiden aus aromatischen Dicarbonsäureestern |
| AUPP598098A0 (en) * | 1998-09-17 | 1998-10-08 | West, Simon Michael | Process for decontaminating ethanediol |
| JP4937521B2 (ja) * | 2005-03-31 | 2012-05-23 | 三井化学株式会社 | ポリエステルより高純度モノマーを回収する方法及び高純度モノマー、ポリエステル |
| CN101979422B (zh) * | 2010-10-15 | 2012-02-22 | 济南大学 | 一种绿色高分子聚合物制备方法和应用 |
| JP2012219210A (ja) * | 2011-04-12 | 2012-11-12 | Ａｓ Ｒ＆Ｄ合同会社 | 低分子ポリマーの製造方法、その方法により得られる低分子ポリマー、その低分子ポリマーを用いた塗料、粉体塗料、接着剤、繊維及び不織布 |
| WO2019140245A1 (en) * | 2018-01-12 | 2019-07-18 | Tyton Biosciences, Llc | Methods for recycling cotton and polyester fibers from waste textiles |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1015422B (de) * | 1953-07-17 | 1957-09-12 | Ici Ltd | Verfahren zum Reinigen von Terephthalsaeure |
| DE1061772B (de) * | 1957-02-08 | 1959-07-23 | Rhodiaceta | Verfahren zur Herstellung von Terephthalsaeure durch Abbau von Polymethylenterephthalaten |
| NL245503A (enrdf_load_stackoverflow) * | 1958-11-18 |
-
1981
- 1981-06-12 MX MX18778581A patent/MX157433A/es unknown
-
1982
- 1982-06-04 BR BR8203311A patent/BR8203311A/pt unknown
- 1982-06-05 DE DE19823221341 patent/DE3221341A1/de active Granted
- 1982-06-11 FR FR8210264A patent/FR2507595A1/fr active Pending
- 1982-06-11 CA CA000404984A patent/CA1188708A/en not_active Expired
- 1982-06-11 JP JP9942082A patent/JPS584735A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6660236B1 (en) | 1998-11-30 | 2003-12-09 | Takeda Chemical Industries, Ltd. | Apparatus for decomposition and recovery of polyurethane resin |
| CN110950751A (zh) * | 2018-09-26 | 2020-04-03 | 远东新世纪股份有限公司 | 对苯二甲酸的制造方法及其系统 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3221341A1 (de) | 1982-12-30 |
| FR2507595A1 (fr) | 1982-12-17 |
| JPS584735A (ja) | 1983-01-11 |
| JPH0316328B2 (enrdf_load_stackoverflow) | 1991-03-05 |
| DE3221341C2 (enrdf_load_stackoverflow) | 1992-05-07 |
| MX157433A (es) | 1988-11-23 |
| BR8203311A (pt) | 1983-05-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |