WO1997024310A1 - Process for manufacturing terephthalic acid - Google Patents
Process for manufacturing terephthalic acid Download PDFInfo
- Publication number
- WO1997024310A1 WO1997024310A1 PCT/KR1995/000185 KR9500185W WO9724310A1 WO 1997024310 A1 WO1997024310 A1 WO 1997024310A1 KR 9500185 W KR9500185 W KR 9500185W WO 9724310 A1 WO9724310 A1 WO 9724310A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- terephthalic acid
- alkali metal
- earth metal
- manufacturing
- acid
- Prior art date
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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
Definitions
- This invention relates to a process for manufacturing terephthalic acid and more particularly, to a process for manufacturing the highly purified terephthalic acid in a high recovery rate, in accordance with the practice of this invention comprising the following procedures: polyethylene terephthalate (hereinafter referred to as "PET") scrap is hydrolyzed with an akaline aqueous solution to give the slurry of terephthalic acid alkali metal /earth metal salt, then the particle of terephthalic acid formed from acid-neutralization is enlarged to recover the highly purified terephthalic acid.
- PET polyethylene terephthalate
- the PET waste scrap materials which are discharged after using them from the end-users, refer to polyester scrap textiles, PET scrap bottles, PET scrap containers, polyethylene terephthalate scrap chips generated in the polymerization process of PET, or polyester scrap yarns generated from the process of manufacturing polyester fibers yarns and textiles.
- the need for the reutilization of the PET scrap being incessantly discharged by one's daily life or in the manufacturing process, has created a great issue in the viewpoint of reducing production costs and abating environmental problems.
- various processes have been proposed for the recovery of terephthalic acid from the PET scrap but they arenot efficient and economical.
- PET was hydrolyzed with a solvent such as water in the presence of decoloring carbon at 200 to 300°C, then cooled under reduced pressure to 5 recover terephthalic acid.
- PET was reacted by saponification with 20 sodium hydroxide solution at 150°C in the presence of ethylene glycol, to prepare disodium terephthalate. Then, the resulting solution was filtered, washed with ethylene glycol or aqueous solution of disodium terephthalate at over 90°C and dissolved in water. Activated charcoal was added to the solution at 90°C, agitated and neutralized with sulfuric acid. Then,
- PET was reacted with alkali metal/earth metal hydroxide at atmospheric pressure and 140 to 180 °C, to prepare terephthalic acid alkali metal/earth metal salt.
- This material was dissolved in water to extract impurities with C 3 to C 8 , alcohols, then neutralized with acid and followed by filtration to recover terephthalic acid.
- PET was reacted with sodium hydroxide in the presence of a mixing extruder without the addition of solvent and then, the obtained disodium terephthalate was dissolved in water, passed through activated charcoal and neutralized with sulfuric acid. The resulting solution was filtered and washed to recover terephthalic acid.
- the particle size of terephthalic acid should be sufficiently enlarged because small particles of terephthalic acid cause insufficient separation into solids and liquids which is responsible for reduction of recovery rate, and also make it difficult to perform the drying process. Nevertheless, said reported methods did not mention any steps of enlarging the particle sizes of terephthalic acid.
- the drawing is a schematic diagram showing the process of manufacturing terephthalic acid in accordance with this invention.
- the object of present invention is to provide a process for ⁇ o manufacturing terephthalic acid in accordance with the practice of this invention comprising the following procedures: PET was hydrolyzed with an alkali aqueous solution containing a wetting agent, and terephthalic acid was prepared by the neutralization of acid.
- PET was hydrolyzed with an alkali aqueous solution containing a wetting agent
- terephthalic acid was prepared by the neutralization of acid.
- the present invention may be described in more detail as shown below.
- the present invention is characterized by a process for manufacturing terephthalic acid comprising the following steps:
- the present invention also relates to several kinds of successively installed tanks for manufacturing terephthalic acid from PET scrap, a raw material, which is charaterized by the following systems: hydrolysis system (1) where said PET scrap is hydrolyzed to prepare terephthalic acid alkali metal/earth metal salt; dissolving system (2) where terephthalic acid alkali metal/earth metal salt is dissolved; centrifuge (3); adsorption tower (4); neutralization system(5) where terephthalic acid alkali metal /earth metal salt is neutralized with acid to prepare terephthalic acid; crystallization system (6) where the particle of terephthalic acid is enlarged; cooling system (7); filtering system (8) where the enlarged particle of terephthalic acid is filtered; drying system (9) where filtered terephthalic acid is dried.
- hydrolysis system (1) where said PET scrap is hydrolyzed to prepare terephthalic acid alkali metal/earth metal salt
- dissolving system (2) where terephthalic
- PET scrap is hydrolyzed with an alkali aqueous solution to prepare the slurry of terephthalic acid alkali metal/earth metal salt. Then, the resulting solution is dissolved in water, and impurities are removed during adsorption. The solution was neutralized with acid to prepare terephthalic acid and prior to the recovery of terephthalic acid, the particle of terephthalic acid is sufficiently enlarged so as to enhance the recovery rate of terephthalic acid.
- PET scrap (1 to 25 weight%), alkali metal/earth 5 metal hydroxide (5 to 30 weight%) and a wetting agent (1 to 30 weight%) are charged into reaction tank(l), then agitated by agitator (la), at reaction pressure of 1 to 20 kg/ cm 2 and 30 to 200 ⁇ to conduct the hydrolysis reaction at the agitation rate of 60 to 300rpm for 30 to 120 mins.
- agitator la
- reaction pressure 1 to 20 kg/ cm 2 and 30 to 200 ⁇ to conduct the hydrolysis reaction at the agitation rate of 60 to 300rpm for 30 to 120 mins.
- i o PET scrap is cut into small particles and pulverized in less than 1cm 3 and then, charged into a reaction tank(l).
- alkali metal/earth metal hydroxide used in this invention refers to alkali metal hydroxide or alkali earth metal hydroxide. From said hydrolysis reaction, if less than 5 weight% of alkali metal/earth metal hydroxide is contained in the total volume of reactants, the conversion yield in reaction is low and in case of exceeding 30 weight%, there
- a wetting agent may be selected from the group containing alcohols of C, to C 4 and surfactant. If less than 1 weight% of said wetting agent is contained in the total volume of reactants, the reaction rate become
- the relative decrease of water content may enhance the concentration of terephthalic acid alkali metal/earth metal salt and thus, the increased viscosity makes it difficult to operate the reaction in an efficient manner.
- the reaction temperature in said hydrolysis is less than 30°C or reaction pressure is less than lkg/cm 2 , the reaction rate becomes very low and this proved to be economically infeasible.
- PET is converted to terephthalic acid alkali metal /earth metal salt.
- solubility of terephthalic acid alkali metal /earth metal salt to water is about 13 weight% at room temperature, so it may exist in ⁇ o the form of slurry.
- reaction tank (1) The solution of terephthalic acid alkali metal/earth metal salt is transferred from reaction tank (1) to dissolving tank(2). Said solution is added with water and agitated constantly by agitator (2a) at 60 to 300 rpm for 10 to 60 mins, at atmospheric pressure and 20 to 100°C to prepare an aqueous
- the reaction in dissolving tank 5 (2) is preferably conducted at atmospheric pressure and 20 to 100°C. In order to ensure better adsorption efficiency in the next adsorption process, the dissolving condition exceeding 100°C is not preferable. In addition, the evaporated alcohol and water in the process of solubility is condensed and fed back to reaction tank (1).
- Adsorption tower (4) plays a role of removing impurities contained in PET (e.g., metal, metal compound, organic compound, dirt, etc.).
- the purity of terephthalic acid, a final product, is determined based upon the removal efficiency in adsorption tower (4).
- activated carbon as a filling material of adsorption tower (4) which is stable in alkali solution, is selected for use and in consideration of its adsorption rate, the surface area of activated carbon per unit volume should be preferably within 500 to 1,500 m 2 /g.
- the reaction of adsorption tower (4) should be preferably conducted at reaction pressure of 0.01 to 10.0 kg/cm 2 and 20 to 100°C, so as to further enhance the efficiency of removing impurities.
- the appropriate residence time in adsorption tower (4) is 1 to 60 mins but the residence time may be more or less adjusted in accordance with the reaction pressure.
- the aqueous solution of terephthalic acid alkali metal/earth metal salt, passed through adsorption tower (4), is transferred to neutralization tank (5) for neutralization with acid. While agitating by agitator (5a) in neutralization tank (5), said solution is mixed slowly with such strong acid as hydrochloric acid, sulfuric acid, nitric acid and phosphoric acid. Then, terephthalic acid alkali metal/earth metal salt is neutralized to prepare terephthalic acid and alkali metal /earth metal salt individually.
- the obtained alkali metal/earth metal salt is freely soluble in water due to its larger solubility to water, while terephthalic acid in solid state is crystallized. Since the particle size of crystallized terephthalic acid is so small, terephthalic acid may not be efficiently separated by a method of separating solids and liquids (e.g., centrifugation or filtration). Even if separated, its recovery rate is quite low and thus, the commercial application is not economically feasible. According to this invention, therefore, the slurry of terephthalic acid, so obtained from said neutralization process, is charged into crystallization tank (6) to sufficiently enlarge the particles size of terephthalic acid.
- Crystallization temperature drop in tank (6) should be preferably within 30 to 50°C.
- All the crystallization tanks (6) should be operatable with in the following specification : temperature in 120 to 300°C, pressure in 2 to 86 kg/cm 2 and agitation rate at 60 to 300 rpm.
- the total residence time required to completely pass through crystallization tank (6) is preferably 30 to 180 mins.
- any acid contained in the slurry of terephthalic acid, passed through said neutralization process should be lower than 10 weight%.
- Strong corrosion-resistant material should be selected such as stainless steel type 316 or titanum for crystallization tank.
- the sufficiently enlarged terephthalic acid in said crystallization tank (6) is charged into the next cooling tank (7) and cooled at pressure of 0.1 to 1.0kg/ cm 2 and temperature of 60 to 90°C. Hence, alcohol contained in the slurry is evaporated with water.
- the evaporated alcohol and water are condensed and then, fed back to reaction tank (1).
- the slurry of cooled terephthalic acid is delivered to filter (8) to separate solids and liquids.
- the operation temperature of filter (8) depends on the slurry temperature of terephthalic acid and the temperature is preferably maintained at 60 to 80°C.
- the pressure should be preferably 0.1 to 0.8kg/ cm 2 .
- terephthalic acid is separated as wet cake and alkali metal/earth metal as filtrate solution.
- the filtered terephthalic acid is washed with water and in consideration of washing efficiency 0.5 to 1.2 times of water to terephthalic acid (30 to 80°C) in proportion to terephthalic acid is preferably used.
- the filtered terephthalic acid is charged into dryer (9) and dried at pressure of 0.5 to 1.0 kg/cm 2 and 100 to 150°C for 10 to 120 mins, to give terephthalic acid, a final product of this invention.
- the filtrate discharged from said filtration process is concentrated by evaporating water, or without evaporation of water, the filtrate is charged into electrodialyzer (10) using bipolar membrane, to individually separate acid and base of alkali metal/earth metal hydroxide.
- the acid, so separated and recovered, is fed back to neutralization tank (5), while alkali metal hydroxide /earth metal is also fed back to reaction tank (1).
- alkali metal/earth metal salt e.g., sodium hydrochloride or sodium sulfate
- alkali metal/earth metal ion such as Na + ion
- alkali metal /earth metal hydroxide such as sodium hydroxide
- the acidic anion such as Cl " ion or S0 4 2" ion, passed through anion membrane, is bound with H + ion to form acids such as hydrochloric acid or sulfuric acid.
- this invention is intended to provide a process for reusing the feed-back reacting raw materials including solvents discharged from each manufacturing step, thus making it possible to reduce product costs and also to abate environmental problems caused by waste materials. Futher, terephthalic acid, so separated and recovered from said manufacturing process, may be obtained with a high yield of 98% or better.
- EXAMPLE 1 EXAMPLE 1.
- reaction tank (1) 500g of water and 30g of sodium hydroxide were charged into reaction tank (1) and dissolved. After the addition of 200g of methanol and lOg of pulverized PET scrap, the mixture was agitated by agitator (300 rpm) at pressure of 8kg/cm 2 and temperature of 150°C for 120 mins. The reaction solution in reaction tank (1) was transferred to dissolving tank (2), added with 400g of water and agitated by agitator (2a, 60 rpm) at atmospheric pressure and temperature of 65°C for 10 mins
- PET was contained in said solids and thus, it is well understood that the reaction rate of PET was 98.6%.
- the adsorption tower (4) was filled with activated charcoal of surface area of 1,500 m 2 /g. 5
- the particle of ⁇ o terephthalic acid formed from said neutralization process its particle size (5 to 20 wn) was very small.
- the crystallization tank (6) is of stainless steel type 316 and has the following reaction requirements:
- reaction tank (1) 20 reaction tank (1).
- the cooled slurry of terephthalic acid was delivered to filter (8) to individually separate solids and liquids, at reaction pressure of 0.8kg/cm 2 and temperature of ⁇ O'C. Then, terephthalic acid in solid state was recovered.
- the filtered terephthalic acid was charged into dryer (9) and dried at reaction pressure of lkg/cm 2 and temperature of 150°C for 10
- reaction solution in reaction tank (1) was transferred to dissolving ⁇ o tank (2), added with 400g of water and agitated by agitator (2a, 200 rpm) at atmospheric pressure and temperature of 50°C for 30 mins.
- the temperature of the first crystallization tank was determined at 200°C in such a fabrication that the temperature of said crystallization tank was lowered to 50°C stepwise and the total residence time, passed through the whole crystallization tank(6), was 60 mins.
- the sufficiently enlarged slurry of terephthalic acid in said crystallization tank (6) was charged into the next cooling tank (7) and cooled under reduced pressure, at pressure of lkg/cm 2 and temperature of 90°C.
- the evaporated methanol and water were condensed and fed back to reaction tank (1).
- the slurry of cooled terephthalic acid was delivered to filter (8) to individually separate solids and liquids, at pressure of 0.5kg/cm 2 and temperature of 80°C.
- terephthalic acid in wet cake was recovered.
- the filtered terephthalic acid was charged into dryer (9) and dried at pressure of 0.5kg/cm 2 and temperature of 150°C for 60 mins to give 16.2g of terephthalic acid.
- the filtrate discharged from said filter (8) was charged into electrodialyzer (10) with 3 chamber-type bipolar membrane and sodium sulfate contained in said filtrate was electrolyzed to separate sulfuric acid and sodium hydroxide. Then, each of said alkali and acid was individually fed back to reaction tank (1) or neutralization tank (5).
- EXAMPLE 3 EXAMPLE 3.
- reaction tank (1) 300g of water and 150g of sodium hydroxide were charged into reaction tank (1) and dissolved. After the addition of 300g of methanol, 5g of surfactant (SURMAX CS 727, Chemax Inc.) and 250g of pulverized PET scrap, the mixture was agitated by an agitator (100 rpm) at pressure of 5 kg/cm 2 and temperature of lOO'C for 120 mins.
- surfactant SURMAX CS 727, Chemax Inc.
- reaction tank (1) The solution in reaction tank (1) was transferred to dissolving tank (2), added with l,500g of water and agitated by agitator (2a, 300 rpm) at atmospheric pressure and temperature of 50°C for 60 mins. Hence, the evaporated alcohol and water were condensed and fed back to reaction tank
- the crystallization tank (6) is of titanum or stainless steel type 316 which was connected with five crystallization tanks in series and each of crystallization tank has the following reaction requirements: pressure in 2 to 86 kg/cm 2 and agitation rate at 120 to 200 rpm.
- the temperature of the first crystallization tank was determined at 300°C in such a fabrication that the temperature of said crystallization tank was lowered to 30 to 50°C stepwise and the total residence time, passed through the whole crystallization tank (6), was 180 mins.
- reaction tank (1) 735g of water and 50g of sodium hydroxide were charged into reaction tank (1) and dissolved.
- reaction tank (1) The solution in reaction tank (1) was transferred to dissolving tank (2), added with l,000g of water and agitated by agitator (2a, 300 rpm) at pressure of 1 kg/cm 2 and temperature of 100°C for 20 mins. Hence, the evaporated alcohol and water were condensed and fed back to reaction tank (1).
- the crystallization tank (6) is of titanum or stainless steel type 316 which was connected with three crystallization tanks in series and each of crystallization tank has the following reaction requirements: pressure in 2 to 15 kg/cm 2 and agitation rate in 200 to 300 rpm.
- the temperature of the first crystallization tank was determined at 200°C in such a fabrication 5 that the temperature of said crystallization tank was lowered to 30 to 50°C stepwise and the total residence time, passed through the whole crystallization tank (6), was 60 mins.
- the filtered terephthalic acid was charged into dryer (9) and dried at pressure of 0.8kg/cm 2 and temperature of 120°C for 120 mins to give 99g of terephthalic acid.
- the filtrate discharged from said filter (8) was charged into electrodialyzer (10) with 3 chamber-type bipolar membrane and sodium sulfate contained in said filtrate was electrolyzed to separate sulfuric acid and sodium hydroxide. Then, each of said alkali and acid was individually fed back to reaction tank (1) or neutralization tank (5).
- Color value DIANO Match Scan II Colorimeter was introduced to monior the values of color L, a and b.
- Metal content XRF (X-ray refractive fluorescence) was introduced to monitor the metal content of Co, Mn and Fe.
- Average particle size (tun) 54 66 102 81
- terephthalic acid recovered by the methods of this invention does not contain any metals and also maintain a high purity, it is very useful in preparing polyester resin.
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Abstract
Description
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Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/KR1995/000185 WO1997024310A1 (en) | 1995-12-30 | 1995-12-30 | Process for manufacturing terephthalic acid |
JP09524218A JP3140469B2 (en) | 1995-12-30 | 1995-12-30 | Method for producing terephthalic acid |
EP95941923A EP0873296B1 (en) | 1995-12-30 | 1995-12-30 | Process for manufacturing terephthalic acid |
US09/101,001 US6075163A (en) | 1995-12-30 | 1995-12-30 | Process for manufacturing terephthalic acid |
DE69522479T DE69522479T2 (en) | 1995-12-30 | 1995-12-30 | METHOD FOR PRODUCING TEREPHTALIC ACID |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/KR1995/000185 WO1997024310A1 (en) | 1995-12-30 | 1995-12-30 | Process for manufacturing terephthalic acid |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1997024310A1 true WO1997024310A1 (en) | 1997-07-10 |
Family
ID=19406465
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/KR1995/000185 WO1997024310A1 (en) | 1995-12-30 | 1995-12-30 | Process for manufacturing terephthalic acid |
Country Status (5)
Country | Link |
---|---|
US (1) | US6075163A (en) |
EP (1) | EP0873296B1 (en) |
JP (1) | JP3140469B2 (en) |
DE (1) | DE69522479T2 (en) |
WO (1) | WO1997024310A1 (en) |
Cited By (8)
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WO1999038835A1 (en) * | 1998-01-30 | 1999-08-05 | Tredi | Method for producing a purified alkaline metal terephthalate, derived from the products of saponification of polyterephthalates |
WO2003042288A1 (en) * | 2001-11-16 | 2003-05-22 | Hitachi Chemical Co., Ltd. | Method for dissolving saturated polyester, solution for decomposing saturated polyester and method for decomposition using the same |
US9550713B1 (en) | 2015-07-09 | 2017-01-24 | Loop Industries, Inc. | Polyethylene terephthalate depolymerization |
US10252976B1 (en) | 2017-09-15 | 2019-04-09 | 9449710 Canada Inc. | Terephthalic acid esters formation |
WO2019174656A1 (en) | 2018-03-12 | 2019-09-19 | JBPV s.r.o. | Method of obtaining terephthalic acid from waste polyethylene terephthalate |
US10808096B2 (en) | 2018-06-25 | 2020-10-20 | 9449710 Canada Inc. | Terephthalic acid esters formation |
US11248103B2 (en) | 2019-03-20 | 2022-02-15 | 9449710 Canada Inc. | Process for the depolymerization of polyethylene terephthalate (PET) |
US12071519B2 (en) | 2017-09-15 | 2024-08-27 | 9449710 Canada Inc. | Terephthalic acid esters formation |
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JP3808672B2 (en) * | 1999-11-26 | 2006-08-16 | 東洋製罐株式会社 | Industrial recovery method of terephthalic acid from recovered pulverized polyethylene terephthalate |
US6720448B2 (en) * | 2000-10-11 | 2004-04-13 | Massimo Broccatelli | Method of recovering chemical species by depolymerization of poly (ethylene terephthalate) and related use |
US7157139B2 (en) * | 2004-04-19 | 2007-01-02 | Grant W. Doney | Polymer manufacturing process |
MX2008012690A (en) * | 2006-04-03 | 2008-10-10 | Cobarr Spa | Recovery of aromatic dicarboxylic acids from waste polyester resin in the presence of a polyamide. |
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WO2012115984A2 (en) | 2011-02-21 | 2012-08-30 | Felice Kristopher M | Polyurethane dispersions and methods of making and using same |
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US9732026B2 (en) | 2012-12-14 | 2017-08-15 | Resinate Technologies, Inc. | Reaction products containing hydroxyalkylterephthalates and methods of making and using same |
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DE102018122210B4 (en) | 2018-09-12 | 2023-06-29 | Rittec Umwelttechnik Gmbh | Process and use of a device for recycling waste containing polyalkylene terephthalate |
JP7419716B2 (en) * | 2019-09-20 | 2024-01-23 | 東洋紡株式会社 | Manufacturing method of recycled polymer material |
TWI708761B (en) * | 2019-09-26 | 2020-11-01 | 遠東新世紀股份有限公司 | Method for manufacturing terephthalic acid |
DE102019135578A1 (en) | 2019-12-20 | 2021-06-24 | Rittec Umwelttechnik Gmbh | Process, apparatus and use for reprocessing |
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- 1995-12-30 EP EP95941923A patent/EP0873296B1/en not_active Expired - Lifetime
- 1995-12-30 DE DE69522479T patent/DE69522479T2/en not_active Expired - Fee Related
- 1995-12-30 WO PCT/KR1995/000185 patent/WO1997024310A1/en active IP Right Grant
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Cited By (18)
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FR2774374A1 (en) * | 1998-01-30 | 1999-08-06 | Tredi | PROCESS FOR THE PRODUCTION OF TEREPHTHALATE FROM A PURIFIED ALKALINE METAL FROM SAPONIFICATION PRODUCTS OF RECOVERY ALKYLENE POLYTEREPHTHALATES |
US6657077B1 (en) | 1998-01-30 | 2003-12-02 | Tredi | Method for producing a purified alkaline metal terephthalate, derived from the products of saponification of polyterephthalates |
WO1999038835A1 (en) * | 1998-01-30 | 1999-08-05 | Tredi | Method for producing a purified alkaline metal terephthalate, derived from the products of saponification of polyterephthalates |
WO2003042288A1 (en) * | 2001-11-16 | 2003-05-22 | Hitachi Chemical Co., Ltd. | Method for dissolving saturated polyester, solution for decomposing saturated polyester and method for decomposition using the same |
US7202283B2 (en) | 2001-11-16 | 2007-04-10 | Hitachi Chemical Co., Ltd. | Method for dissolving saturated polyester solution for decomposing saturated polyester and method for decomposition using the same |
US9550713B1 (en) | 2015-07-09 | 2017-01-24 | Loop Industries, Inc. | Polyethylene terephthalate depolymerization |
US10087130B2 (en) | 2015-07-09 | 2018-10-02 | Loop Industries, Inc. | Polyethylene terephthalate depolymerization |
US10640442B2 (en) | 2015-07-09 | 2020-05-05 | Loop Industries, Inc. | Polyethylene terephthalate depolymerization |
US11866404B2 (en) | 2017-09-15 | 2024-01-09 | 9449710 Canada Inc. | Terephthalic acid esters formation |
US10252976B1 (en) | 2017-09-15 | 2019-04-09 | 9449710 Canada Inc. | Terephthalic acid esters formation |
US10793508B2 (en) | 2017-09-15 | 2020-10-06 | 9449710 Canada Inc. | Terephthalic acid esters formation |
US12071519B2 (en) | 2017-09-15 | 2024-08-27 | 9449710 Canada Inc. | Terephthalic acid esters formation |
WO2019174656A1 (en) | 2018-03-12 | 2019-09-19 | JBPV s.r.o. | Method of obtaining terephthalic acid from waste polyethylene terephthalate |
US11401398B2 (en) | 2018-06-25 | 2022-08-02 | 9449710 Canada Inc. | Terephthalic acid esters formation |
US12071520B2 (en) | 2018-06-25 | 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 |
US11795291B2 (en) | 2019-03-20 | 2023-10-24 | 9449710 Canada Inc. | Process for the depolymerization of polyethylene terephthalate (PET) |
US11248103B2 (en) | 2019-03-20 | 2022-02-15 | 9449710 Canada Inc. | Process for the depolymerization of polyethylene terephthalate (PET) |
Also Published As
Publication number | Publication date |
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EP0873296B1 (en) | 2001-08-29 |
DE69522479T2 (en) | 2002-05-08 |
JP3140469B2 (en) | 2001-03-05 |
US6075163A (en) | 2000-06-13 |
DE69522479D1 (en) | 2001-10-04 |
JPH11502868A (en) | 1999-03-09 |
EP0873296A1 (en) | 1998-10-28 |
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