WO2022259026A1 - Procédé pour l'obtention d'acide téréphtalique et récupération d'hydroxyde de sodium d'une solution de téréphtalate de sodium produit à partir de polyéthylène téréphtalate (pet) de réutilisation - Google Patents

Procédé pour l'obtention d'acide téréphtalique et récupération d'hydroxyde de sodium d'une solution de téréphtalate de sodium produit à partir de polyéthylène téréphtalate (pet) de réutilisation Download PDF

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Publication number
WO2022259026A1
WO2022259026A1 PCT/IB2021/055081 IB2021055081W WO2022259026A1 WO 2022259026 A1 WO2022259026 A1 WO 2022259026A1 IB 2021055081 W IB2021055081 W IB 2021055081W WO 2022259026 A1 WO2022259026 A1 WO 2022259026A1
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WO
WIPO (PCT)
Prior art keywords
terephthalic acid
sodium hydroxide
sodium
pet
recovery
Prior art date
Application number
PCT/IB2021/055081
Other languages
English (en)
Spanish (es)
Inventor
Arturo Guadalupe FREGOSO INFANTE
Jorge Guillermo IBAÑEZ CORNEJO
Rubén César VÁSQUEZ MEDRANO
Jorge Alberto BENÍTEZ ARÉVALO
Diego MILLÁN GONZÁLEZ
Original Assignee
Universidad Iberoamericana, A.C.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Universidad Iberoamericana, A.C. filed Critical Universidad Iberoamericana, A.C.
Priority to EP21944450.2A priority Critical patent/EP4353876A1/fr
Priority to PCT/IB2021/055081 priority patent/WO2022259026A1/fr
Priority to CA3221682A priority patent/CA3221682A1/fr
Priority to CN202180101442.3A priority patent/CN117858981A/zh
Publication of WO2022259026A1 publication Critical patent/WO2022259026A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B1/00—Electrolytic production of inorganic compounds or non-metals
    • C25B1/01—Products
    • C25B1/14—Alkali metal compounds
    • C25B1/16—Hydroxides
    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B3/00—Electrolytic production of organic compounds

Definitions

  • the present invention is related to obtaining terephthalic acid, and more particularly it is related to a process for obtaining terephthalic acid and recovery of sodium hydroxide from a sodium terephthalate solution produced from reusable PET.
  • Terephthalic acid has various applications in the chemical, cosmetic, and even pharmaceutical industries.
  • the most common way to obtain terephthalic acid is from oil, however, this way of obtaining it is not a good viable option in the long term, since oil is a non-renewable resource.
  • sodium hydroxide NaOH
  • sodium hydroxide can be obtained electrolytically using ion exchange membranes from aqueous sodium chloride solutions.
  • this industrial process typically only produces solutions of between 20 and 40% sodium hydroxide and requires more operations to obtain it in the solid state.
  • JP2004250544 refers to a process for recovering terephthalic acid from a terephthalic acid polyester by electrolysis.
  • the method uses an alcoholic solution of ethylene glycol, sodium sulfate, and water as catholyte for electrolysis.
  • this document does not consider the recovery of sodium hydroxide from a sodium terephthalate solution, so it is not suitable as a complement to the PET recycling process.
  • Document JP11302208 describes a method for producing terephthalic acid and ethylene glycol from PET.
  • the method comprises contacting PET with sodium hydroxide in ethylene glycol and subsequently separating the sodium terephthalate produced.
  • the method described in the document JP11302208 requires reaching high temperatures of between 170 °C and 180 °C, which increases the cost of the process to recycle PET, since a large amount of energy and special equipment are needed to that these temperatures can be reached, in addition to the fact that some acid is used to obtain terephthalic acid, eg sulfuric acid, thus obtaining sodium sulfate as a by-product.
  • Another object of the present invention is to provide a process for obtaining terephthalic acid and recovery of sodium hydroxide from a sodium terephthalate solution produced from reusable PET that does not need to use large amounts of water and electricity.
  • Another object of the present invention is to provide a process for obtaining terephthalic acid and recovering sodium hydroxide from a sodium terephthalate solution produced from reusable PET that does not generate a large amount of by-products.
  • the present invention refers to a process for obtaining terephthalic acid and sodium hydroxide recovery from a sodium terephthalate solution produced from reusable PET, which comprises the following steps: i) placing in a cell electrolytic a sodium terephthalate solution obtained from a PET hydrolysis process on the anodic side; ii) placing an alcoholic medium on the cathode side of the electrolytic cell; iii) applying an electric current that flows through the anodic side and the cathodic side of the electrolytic cell and; iv) recover terephthalic acid and sodium hydroxide.
  • Figure 1 shows a diagram of the chemical reaction of a process for obtaining terephthalic acid and recovery of sodium hydroxide from a solution of sodium terephthalate produced from PET for reuse within the electrolytic cell in accordance with the present invention.
  • a process has been found for obtaining terephthalic acid and recovering sodium hydroxide from a sodium terephthalate solution produced from reusable PET, which does not require large amounts of water or energy.
  • one aspect of the present invention is a process for obtaining terephthalic acid and sodium hydroxide recovery from a sodium terephthalate solution produced from reusable PET, which comprises the following steps: i) placing in a cell electrolytic a sodium terephthalate solution obtained from a PET hydrolysis process on the anodic side; i i) placing an alcoholic medium on the cathodic side of the electrolytic cell; iii) applying an electric current that flows through the anodic side and the cathodic side of the electrolytic cell and; iv) recover terephthalic acid and sodium hydroxide.
  • the alcoholic medium placed on the cathode side of the electrolytic cell is methanol, ethanol, propanol, butanol, or a mixture thereof.
  • sodium hydroxide is added to the alcoholic medium placed on the cathode side of the electrolytic cell to obtain an alcoholic solution.
  • the alcoholic solution with sodium hydroxide has a molarity of 0.25 M to 1 M.
  • the electrolytic cell has a membrane or diaphragm between the anodic side and the cathodic side.
  • the electrical current applied to the electrolytic cell has a density between 0.1 to 0.5 Amperes/cm 2 .
  • the applied electrical current is continuously measured to determine the number of Coulombs passing the electrodes.
  • electrical current is applied to the electrolytic cell for a period of 50 to 70 minutes. Preferably, after the period of time the electrodes are removed.
  • a cell could be designed to work continuously.
  • a solution of terephthalic acid is obtained from the anodic side of the electrolytic cell and sodium hydroxide and sodium alkoxide in an alcoholic solution are obtained from the cathodic side of the electrolytic cell.
  • the solution on the anodic side, which contains precipitated terephthalic acid is filtered.
  • the water-washed terephthalic acid is dried in an oven at a temperature of between 125 to 135°C.
  • the terephthalic acid is dried in the oven for 50 to 70 minutes.
  • the percent electronic efficiency of terephthalic acid recovery relative to sodium terephthalate solution is 50 to 85%.
  • the sodium alkoxide is in an alcoholic solution and in a concentration between 5% to 30% (m/V).
  • sodium hydroxide is obtained by adding the stoichiometric amount of water.
  • Solid sodium hydroxide is obtained by evaporation of the corresponding alcohol. It should be noted that the production of terephthalic acid and sodium hydroxide occurs simultaneously.
  • Figure 1 shows a schematic of the chemical reaction of the process for obtaining terephthalic acid and recovery of sodium hydroxide from a solution of sodium terephthalate produced from reused PET within the electrolytic cell.
  • the anodic side is shown, that is to say, from the left side of figure 1 and the cathodic side, that is to say, from the right side of figure 1 seen frontally.
  • an aqueous solution of sodium terephthalate is introduced on the anode side of said electrolytic cell and on the cathode side an alcoholic medium with sodium hydroxide is introduced.
  • a test was carried out to recover terephthalic acid and sodium hydroxide from a sodium terephthalate solution obtained from a PET hydrolysis process in accordance with the present invention.
  • the sodium terephthalate solution was prepared with 12 g of sodium terephthalate and 100 mL of water. From the cathodic side of the electrolytic cell, 90 mL of a methanol solution with sodium hydroxide were added. The solution was prepared with 1 g of NaOH and 100 mL of methanol.
  • a platinum electrode was placed on the anodic side and a stainless steel electrode on the cathodic side, and the electrolytic cell was connected to a power source.
  • the power source was turned on and the current was controlled, which for one hour was maintained with an electrical intensity of 0.4 to 0.6 Amperes.
  • the electrolytic cell was connected to an ammeter that continuously measured and recorded the current that passed through the electrodes and in this way the amount of electricity in Coulombs that passed through the electrodes of the electrolytic cell was determined.
  • the power source was turned off, the electrodes on each side of the electrolytic cell were removed and the solution on the anodic side, which contained precipitated terephthalic acid, was filtered, said precipitate was washed and the washed terephthalic acid was dried in oven at 130°C for one hour and then weighed. From the cathodic side, sodium methoxide was obtained. Adding water to this solution gives sodium hydroxide in methanol. Solid sodium hydroxide is obtained by evaporation of the corresponding alcohol. During the test, the temperatures of the two half-cells were measured, as well as the variations in the current between the two electrodes of the electrolytic cell, in order to know the efficiency of the precipitated terephthalic acid obtained.
  • the amount of terephthalic acid obtained is good considering the amount of mL of sodium terephthalate solution with which the reaction started.
  • the mL of water that was used and the electrical energy necessary for the reaction represent a very low cost in relation to the cost at which terephthalic acid and sodium hydroxide can be sold.
  • a test was carried out using different reaction times in a process for obtaining terephthalic acid and recovery of sodium hydroxide from a sodium terephthalate solution produced from reuse PET, in accordance with the present invention.
  • the purpose of this test is to see if there is variation in the efficiency of the process. From the results obtained it can be seen that there is no significant difference.
  • a test was carried out using different electrical currents in a process for obtaining terephthalic acid and recovery of sodium hydroxide from a sodium terephthalate solution produced from reuse PET, in accordance with the present invention.
  • the purpose of this test is to observe variation in the efficiency of obtaining terephthalic acid.
  • the experiments were carried out in the same cell and under the same conditions as in Example 1, except that there was variation in the amount of current during electrolysis. Table 3 shows the results obtained.
  • the described method does not require large amounts of water or energy, and practically does not generate by-products, and it will be evident to any person skilled in the art that the modalities of a process for obtaining terephthalic acid and recovering sodium hydroxide from a solution of sodium terephthalate produced from reuse PET as previously described and illustrated in the accompanying drawing, are only illustrative and not limiting of the present invention, since numerous considerable changes are possible in its details without departing from the scope of the invention.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Electrochemistry (AREA)
  • Materials Engineering (AREA)
  • Metallurgy (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Un procédé pour l'obtention d'acide téréphtalique et la récupération d'hydroxyde de sodium d'une solution de téréphtalate de sodium produit à partir de PET de réutilisation comprend les étapes suivantes qui consistent à i) placer dans une cellule électrolytique une solution de téréphtalate de sodium obtenue d'un processus d'hydrolyse de PET côté anode; ii) placer du côté cathode de la cellule électrolytique un milieu alcoolique; iii) appliquer un courant électrique circulant à travers le côté anode et le côté cathode de la cellule électrolytique et; iv) récupérer l'acide téréphtalique et l'hydroxyde de sodium. Le procédé a été conçu pour ne pas générer les sous-produits générés dans le processus de recyclage de PET, et ainsi comprendre un processus "vert". En outre, le procédé décrit ne requiert pas de grandes quantités d'eau ni d'énergie.
PCT/IB2021/055081 2021-06-09 2021-06-09 Procédé pour l'obtention d'acide téréphtalique et récupération d'hydroxyde de sodium d'une solution de téréphtalate de sodium produit à partir de polyéthylène téréphtalate (pet) de réutilisation WO2022259026A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP21944450.2A EP4353876A1 (fr) 2021-06-09 2021-06-09 Procédé pour l'obtention d'acide téréphtalique et récupération d'hydroxyde de sodium d'une solution de téréphtalate de sodium produit à partir de polyéthylène téréphtalate (pet) de réutilisation
PCT/IB2021/055081 WO2022259026A1 (fr) 2021-06-09 2021-06-09 Procédé pour l'obtention d'acide téréphtalique et récupération d'hydroxyde de sodium d'une solution de téréphtalate de sodium produit à partir de polyéthylène téréphtalate (pet) de réutilisation
CA3221682A CA3221682A1 (fr) 2021-06-09 2021-06-09 Procede pour l'obtention d'acide terephtalique et recuperation d'hydroxyde de sodium d'une solution de terephtalate de sodium produit a partir de polyethylene terephtalate (pet) de reutilisatio
CN202180101442.3A CN117858981A (zh) 2021-06-09 2021-06-09 从再利用的聚对苯二甲酸乙二醇酯(pet)生产的对苯二甲酸钠溶液中获取对苯二甲酸并回收氢氧化钠的工艺

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/IB2021/055081 WO2022259026A1 (fr) 2021-06-09 2021-06-09 Procédé pour l'obtention d'acide téréphtalique et récupération d'hydroxyde de sodium d'une solution de téréphtalate de sodium produit à partir de polyéthylène téréphtalate (pet) de réutilisation

Publications (1)

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WO2022259026A1 true WO2022259026A1 (fr) 2022-12-15

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Country Status (4)

Country Link
EP (1) EP4353876A1 (fr)
CN (1) CN117858981A (fr)
CA (1) CA3221682A1 (fr)
WO (1) WO2022259026A1 (fr)

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4093528A (en) * 1977-03-10 1978-06-06 Suntech, Inc. Terephthalic acid process
EP0573042A1 (fr) * 1992-06-04 1993-12-08 MITSUI TOATSU CHEMICALS, Inc. Procédé de décomposition des matières plastiques contenant un polymère d'acide hydroxycarboxylique
US5290404A (en) * 1990-10-31 1994-03-01 Reilly Industries, Inc. Electro-synthesis of alcohols and carboxylic acids from corresponding metal salts
FR2697839A1 (fr) * 1992-11-09 1994-05-13 Inst Francais Du Petrole Procédé amélioré de récupération de téréphtalate de métal alcalin et d'alkylène glycol à partir de polytéréphtalates d'alkylènes.
JPH11302208A (ja) 1998-04-22 1999-11-02 Akira Oku ポリエチレンテレフタレートからテレフタル酸およびエチレングリコールを回収する方法
US6312582B1 (en) * 1997-08-06 2001-11-06 Tredi Formation terephthalic acid by electrochemical acidification of a sodium terephthalate solution
JP2004250544A (ja) 2003-02-19 2004-09-09 Kansai Tlo Kk ポリ（テレフタル酸エステル）からテレフタル酸を回収する方法
US20100038231A1 (en) * 2006-09-08 2010-02-18 Vaclav Vesely Process for recovering terephthalic acid

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4093528A (en) * 1977-03-10 1978-06-06 Suntech, Inc. Terephthalic acid process
US5290404A (en) * 1990-10-31 1994-03-01 Reilly Industries, Inc. Electro-synthesis of alcohols and carboxylic acids from corresponding metal salts
EP0573042A1 (fr) * 1992-06-04 1993-12-08 MITSUI TOATSU CHEMICALS, Inc. Procédé de décomposition des matières plastiques contenant un polymère d'acide hydroxycarboxylique
FR2697839A1 (fr) * 1992-11-09 1994-05-13 Inst Francais Du Petrole Procédé amélioré de récupération de téréphtalate de métal alcalin et d'alkylène glycol à partir de polytéréphtalates d'alkylènes.
US6312582B1 (en) * 1997-08-06 2001-11-06 Tredi Formation terephthalic acid by electrochemical acidification of a sodium terephthalate solution
JPH11302208A (ja) 1998-04-22 1999-11-02 Akira Oku ポリエチレンテレフタレートからテレフタル酸およびエチレングリコールを回収する方法
JP2004250544A (ja) 2003-02-19 2004-09-09 Kansai Tlo Kk ポリ（テレフタル酸エステル）からテレフタル酸を回収する方法
US20100038231A1 (en) * 2006-09-08 2010-02-18 Vaclav Vesely Process for recovering terephthalic acid

Also Published As

Publication number Publication date
EP4353876A1 (fr) 2024-04-17
CA3221682A1 (fr) 2022-12-15
CN117858981A (zh) 2024-04-09

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