PL131961B1 - Method of recovery and regeneration of catalyst of oxidation in industrial process of manufacture of dimethyl terephtalate - Google Patents

Method of recovery and regeneration of catalyst of oxidation in industrial process of manufacture of dimethyl terephtalate Download PDF

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Publication number
PL131961B1
PL131961B1 PL1981230102A PL23010281A PL131961B1 PL 131961 B1 PL131961 B1 PL 131961B1 PL 1981230102 A PL1981230102 A PL 1981230102A PL 23010281 A PL23010281 A PL 23010281A PL 131961 B1 PL131961 B1 PL 131961B1
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catalyst
oxidation
weight
methyl
toluate
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PL1981230102A
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Polish (pl)
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PL230102A1 (en
Inventor
Zofia Pokorska
Renata Fiszer
Jerzy Witkos
Mieczyslaw Smolarek
Jan Pastuchow
Franciszek Blaszkiewicz
Henryk Boebel
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Inst Ciezkiej Syntezy Orga
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Priority to PL1981230102A priority Critical patent/PL131961B1/en
Publication of PL230102A1 publication Critical patent/PL230102A1/xx
Publication of PL131961B1 publication Critical patent/PL131961B1/en

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    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/584Recycling of catalysts

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Przedmiotem wynalazku jest sposób odzyskiwania i regeneracji katalizatora utleniania p-ksylenu 1 p-toluilanu metylu w przemyslowym procesie wytwarzania dwumetylotereftalanu przez ekstrakcje wodami reakcyjnymi lub wodnym roztworem kwasu ootowego skladników katali¬ zatora z pozostalosci po destylacji surowych estrów* W procesie wytwarzania dwumetylotereftalanu skladniki katalizatora utleniania p-ksy¬ lenu i p-toluilanu metylu ekstrahuje sie z pozoatalosci po destylacji surowych estrów rozoienozonymi wodnymi roztworami kwasu ootowego lub mrówkowego lub ich mieszaninamit lub wodami reakcyjnymi z utleniania, W metodach odzyskiwania katalizatora utleniania p-ksylenu 1 p-toluilanu metylu zna¬ nych z opisu patentowego PRL nr 70 344 i 94 790, ekstrakcje skladników katalizatora pro¬ wadzi sie w podwyzszonej temperaturze 1 przy odpowiednich stosunkach wagowych faz, naj¬ korzystniej przy nadmiarze fazy wodnej do organloznej stanowiaoej pozostalosc po desty¬ lacji surowyoh estrów. Stosowanie nadmiaru wagowego wód reakcyjnyoh lub roztworu wodnego kwasu ootowego w stosunku do pozostalosci powodowalo potrzebe zachowawozego zatezanla rozcienczonych wodnych roztworów katalizatora. W wyniku oddestylowania wody nastepowalo nie tylko zatezanle skladników katalizatora ale równiez zwiazków organloznych takloh jak p-tolullan metylu, dwumetylotereftalan, kwasy p-tolullowy 1 monometylotereftalowy i Inne zwiazki wyekstrahowane z pozostalosci po destylacji surowych estrów. Zwiazki organiczne po zatezeniu roztworu wodnego katalizatora latwo wytraoaly sie utrudniajac dozowanie zre¬ generowanego katalizatora do prooesu utleniania p-ksylenu 1 p-toluilanu metylu.Istota sposobu odzyskiwania 1 regeneracji katalizatora prooesu utleniania p-ksylenu 1 p-toluilanu metylu w przemyslowym procesie wytwarzania dwumetylotereftalanu przez ekstrakcje skladników katalizatora z pozostalosci po destylaoji surowych estrów metylowych2 131 961 wodami reakcyjnymi pochodzacymi z procesu utleniania lub wodnym roztworem kwasu octowego, polega na tym, ze do odzyskanego wodnego roztworu katalizatora dodaje sie 5-30% wagowych alkoholu metylowego, po czym calosc zawraca sie do prooesu utleniania.Sposób wedlug wynalazku umozliwia zachowanie aktywnosci katalizatora niezaleznie od czasu i temperatury magazynowania, przeciwdziala wytracaniu sie zwiazków organicznymi) wy¬ ekstrahowanych z pozostalosoi po destylacji surowych estrów w postaci klaozkowatych osadów zatykajacych przewody, zawory 1 pompki dozujace roztwór katalizatora do prooesu utleniania p—ksylenu 1 p-toluilanu metylu* Dodatek alkoholu metylowego do odzyskanych roztworów wod¬ nych katalizatora przeciwdziala nie tylko wytracaniu sie zwiazków organicznych ale równiez nieorganicznych zawierajacych glównie skladniki katalizatora oraz pozwala na zachowanie wysokiej aktywnosci katalizatora* Mozna równiez dodawac alkohol metylowy do roztworów wod¬ nych katalizatora po wytraceniu sie osadów 1 spowodowac przez to ich ponowne rozpuszcze¬ nie w roztworach wodnych.Efektem stosowania sposobu wedlug wynalazku jest calkowite wyeliminowanie strat od¬ zyskanego roztworu wodnego katalizatora 1 zastapienie kosztownych i uciazliwych operacji technicznych takich jak wirowanie lub filtrowanie stosowanych dla usuniecia osadów z roz¬ tworów katalizatora, bardzo prostym sposobem dozowania odpowiedniej ilosci alkoholu mety¬ lowego i wymieszania roztworu katalizatora.Dobór ilosci alkoholu metylowego dodawanego do roztworu wodnego katalizatora zalezy od stosunku wagowego faz w procesie ekstrakcji, temperatury i stopnia zatezania rozcien¬ czonych roztworów wodnych katalizatora o ile prooes zatezania jest stosowany. W kazdym jednak przypadku dodawana ilosc metanolu nie przekraoza 80% wagowych i nie moze byc mniej¬ sza niz 5% wagowych w stosunku do ilosol roztworu katalizatora. W przypadkach nie wytra¬ cania sie osadów z odzyskanych roztworów wodnyoh katalizatora dodaje sie co najmniej 5% wagowych alkoholu metylowego w celu utrzymania wysokiej aktywnosoi katalizatora w cza¬ sie jego magazynowania. 3 Przyklad 1. Do reaktora ze stall Kwasoodpornej o pojemnosci roboozej 3 m zaopatrzonego w mieszadlo, wezownice grzewcza i kondensator par wprowadzono 4 Mg wód reakcyjnych o temperaturze 40°C z procesu utleniania p-ksylenu i p-toluilanu metylu zawie¬ rajacego okolo 4,0% wagowych kwasu octowego, okolo 0,8% wagowych kwasu mrówkowego, okolo 0,6% wagowych aldehydu mrówkowego i octowego 1 okolo 3,0% wagowych metanolu oraz okolo 0,4% wagowych innych ubocznych zwiazków z utleniania. Nastepnie do reaktora tego wprowa¬ dzano 4 Mg pozostalosoi o temperaturze ISO C po destylacji surowych estrów zawierajacych 0,30% wagowych kobaltu, 0,015% wagowych manganu i 0,0033% wagowych niklu. Zawartosc reaktora mieszano i utrzymywano w nim temperature okolo 95°C w ciagu 30 minut, nastepnie wylaczono mieszanie i po 90 minutach odebrano dolem reaktora pozostalosc. Nastepnie roz¬ twór octanów zawierajacyoh prawie cala ilosc kobaltu, manganu i niklu poddano zatezaniu przez wlaczenie pary 0,15 MPa do wezownicy grzewczej. Skroplone opary z zatezania octanów skierowano do zbiornika wód poreakcyjnych. Z poczatkowej ilosol 3,6 Mg octanów kobaltu, manganu i niklu uzyskano po zatezeniu 0,25 Mg ootanów. Oznaczone stezenie sumy metali ka¬ talizatora wynosi 4,58% wagowych.Do tak uzyskanego roztworu o temperaturze 50°C dodano 0J9 Mg metanolu. Oznaczona chromatograficznie analiza roztworu wykazala 3,4% wagowych kwasu octowego. 0,65% wagowych kwasu mrówkowego, 0,2% wagowyoh aldehydu mrówkowego i ootowego, 43% wagowych metanolu oraz 0,5% wagowych innych ubocznych zwiazków z utleniania. Oznaczona zawartosc kobaltu wynosila 2,45% wagowyoh, zawartosc manganu 0,12% wagowych a zawartosc niklu 0,027% wagowych. Przygotowany roztwór katalizatora skierowano do zbiornika magazynowego roztwo¬ ru katalizatora znajdujacego sie w wezle utleniania wytwórni dwumety lot eref talami. Roz¬ twór ten wprowadzano do reaktora utleniania w takiej ilosci, by stezenie metali kataliza¬ tora wynosilo 100 ppm. Uzyskana selektywnosc w przeliczeniu na p-keylen 1 p-toluilan me¬ tylu wyniosla 36% wagowych.Pobrana próbka zatezonego roztworu katalizatora po sohlodzeniu do temperatury 25°C zawierala okolo 4,5% wagowych osadu zawierajacego oprócz takioh zwiazków jak p-toluilan131 961 3 metylu, dwumetylotereftalan i kwas p-toluilowy, monometylotereitalowy i inne okolc 30^ wa¬ gowych skladników, glownie kobaltu* Przyklad II. Ekstrakoje skladników katalizatora z pozostalosci po destylacji surowych estrów prowadzono tak jak w przykladzie I z tym, ze na 4 Mg pozostalosci zastosowa¬ no 3 Mg wód poreakoyjnych z procesu utleniania p-ksylenu i p-toluilanu metylu. Uzyta do ekstrakcji pozostalosc po destylacji surowych estrów zawierala 0,49% wagowyob kobaltu, 0,024% wagowyoh manganu 1 0,0054% wagowych niklu* Po ekstrakcji skladników katalizatora 1 odstaniu odebrano dolen reaktora pozostalosc pozbawiona prawie w oalosol netali katali¬ zatora. Do tej samej porcji wód reakcyjnych dodano 3,8 Mg, pozostalosci po destylacji su¬ rowych estrów o skladzie jak wyzej i poddano ponownej ekstrakcji. Analiza zawartosci pier¬ wiastków metali katalizatora po pierwszej ekstrakcji wykazalo zawartosc 0,694% wagowych sumy metali w tym kobaltu 0,654% wagowych, manganu 0,033% wagowych 1 niklu 0,007% wagowych, natomiast po drugiej ekstrakojl zawartosc sumy metali wyniosla 1,453% wagowych.Po odebraniu dolem reaktora pozostalosci do wodnego roztworu octanów metali kataliza¬ tora dodano 15% wagowych metanolu* Tak otrzymany roztwór o stezeniu sumy metali katalizato¬ ra 1,262% wagowych w tym kobaltu 1,19% wagowych , manganu 0,059% wagowych 1 niklu 0,013% wagowych stosowano jako katalizator w procesie utleniania p-ksylenu 1 p-toluilanu metylu uzyskujac selektywnosc 36,5%.Przyklad III. Do ekstrakt ora jak w przykladzie I wprowadzono 4 Mg wód reak¬ cyjnych z procesu utleniania p-ksylenu i p-toluilanu metylu o temperaturze 40°C 1 skladzie jak w przykladzie Ifa nastepnie wprowadzono 4 Mg pozostalosci po destylacji surowych estrów o temperaturze 180°C o zawartosol skladników katalizatora jak w przykladzie I. Po ekstrakojl skladników katalizatora 1 odstaniu odebrano dolem reaktora pozostalosc,a wykonana analiza wykazala 0,316% wagowych sumy metali skladników katalizatora. Do tej samej porcji wód re- akoyjnyoh po pierwszej ekstrakojl dodano 4 Mg pozostalosol o temperaturze 1 skladzie jak powyzej. Podczas ekstrakcji skladników katalizatora utrzymywano temperature 95°C i po od¬ staniu odebrano dolem pozostalosc a analiza pozostawionyoh w ekstraktorze octanów wykazala 0,6624% wagowych sumy metali skladników katalizatora. Do ekstrakt ora dodano nastepna porcje 4 Mg pozostalosol o skladzie jak powyzej 1 przeprowadzono ekstrakcje skladników katalizatora. Po odstaniu dolem reaktora odebrano pozostalosc a do 3,1 Mg octanów metali skladników katalizatora dodano 15% metanolu /O,465 Mg/.Przeprowadzone analizy wykazaly przed dodaniem metanolu 1,037% wagowyoh sumy metali skladników katalizatora,a po dodaniu metanolu 0,9016% wagowych w tym 0,8498% wagowych kobaltu, 0,0425% wagowych manganu 1 0,00935% wagowych niklu.Przygotowany tym sposobem roztwór katalizatora skierowano do zbiornika magazynowego roztworu katalizatora i uzyto w procesie utleniania p-ksylenu i p-toluilanu metylu w ta- kle-jTilosoi, by stezenie metali katalizatora w mieszaninie reakcyjnej wynosilo 50 ppm.Uzyskana selektywnosc procesu utleniania p-ksylenu i p-toluilanu metylu w przeliczeniu na p-ksylen wynosila 36,5% wagowych.Zastrzezenie patentowe Sposób odzyskiwania 1 regeneraojl katalizatora utleniania w przemyslowym procesie wytwarzania dwumetylotereftalanu przez utlenianie p-ksylenu 1 p-toluilanu metylu i ekstrak¬ cje skladników katalizatora z pozostalosci po destylacji surowych estrów metylowych wodami reakoyjnyml poohodzacymi z procesu utleniania lub wodnym roztworem kwasu ootowego, zna¬ mienny tym, ze do odzyskanego wodnego roztworu katalizatora dodaje sie 5-80% wagowyoh alkoholu metylowego, po czym calosc zawraca sie do procesu utleniania. PLThe subject of the invention is a method of recovering and regenerating the oxidation catalyst of p-xylene and p-methyl toluate in the industrial process of producing dimethyl terephthalate by extraction with reaction water or aqueous ootic acid solution of the catalyst components from the residue after distillation of crude esters. In the process of producing dimethyl terephthalate oxidation catalyst components -Xylene and methyl p-toluate are extracted from the residues after distillation of crude esters with diluted aqueous solutions of ootic or formic acid or mixtures thereof or with oxidation reaction waters. In the recovery of the p-xylene 1 p-methyl toluate oxidation catalyst known from In Polish Patent Specification No. 70,344 and 94,790, the extraction of the catalyst components is carried out at an elevated temperature and with appropriate weight ratios of the phases, most preferably with an excess of water phase to organic phase remaining after distillation of crude esters. The use of an excess by weight of reaction waters or an aqueous solution of ootic acid in relation to the remainder resulted in the need for a conservative coking unit of diluted aqueous catalyst solutions. As a result of the distillation of the water, not only the catalyst components but also organophilic compounds, such as methyl p-tolullan, dimethyl terephthalate, p-toluic acid and monomethyl terephthalate and other compounds extracted from the residues after distillation of crude esters, took place. After concentrating the aqueous solution of the catalyst, the organic compounds easily precipitated, making it difficult to dose the regenerated catalyst for the oxidation of p-xylene and methyl p-toluate. The essence of the recovery process and regeneration of the catalyst for the oxidation of p-xylene and methyl p-toluate in the industrial process of producing dimethyl terephthalate by Extraction of the catalyst components from the distillation residue of crude methyl esters2 131 961 with reaction water from the oxidation process or with aqueous acetic acid consists in adding 5-30% by weight of methyl alcohol to the recovered aqueous catalyst solution and then returning the whole to The method according to the invention makes it possible to maintain the activity of the catalyst irrespective of the time and temperature of storage, it prevents the precipitation of organic compounds extracted from the residues after distillation of crude esters in the form of clog-like sediments clogging the pipes, valves 1 dosing pumps for the catalyst solution for the oxidation of p-xylene and methyl p-toluate * The addition of methyl alcohol to the recovered aqueous solutions of the catalyst counteracts not only the precipitation of organic compounds but also of inorganic compounds containing mainly catalyst components and allows the maintenance of high catalyst activity * also add methyl alcohol to the aqueous solutions of the catalyst after precipitation and thus cause their redissolution in the aqueous solutions. The result of the application of the method according to the invention is the complete elimination of losses of the recovered aqueous solution of the catalyst and replacement of the costly and burdensome technical operations such as such as centrifugation or filtering used to remove deposits from catalyst solutions, a very simple method of dosing the appropriate amount of methyl alcohol and mixing the catalyst solution. Selection of the amount of methyl alcohol added to the kata aqueous solution The lyser is dependent on the weight ratio of the phases in the extraction process, the temperature, and the concentration of the dilute aqueous solutions of the catalyst, if used. In each case, however, the amount of methanol added must not exceed 80% by weight and must not be less than 5% by weight, based on the amount of the catalyst solution. In cases where there is no precipitation of the recovered aqueous solutions of the catalyst, at least 5% by weight of methyl alcohol is added in order to maintain the high activity of the catalyst during its storage. 3 Example 1. Into an acid-resistant steel reactor with a working capacity of 3 m3, equipped with a stirrer, a heating coil and a vapor condenser, 4 Mg of reaction water at a temperature of 40 ° C was introduced from the process of oxidation of p-xylene and methyl p-toluate containing about 4 0 wt.% Acetic acid, about 0.8 wt.% Formic acid, about 0.6 wt.% Formic and acetic aldehyde, and about 3.0 wt.% Methanol, and about 0.4 wt.% Other oxidation by-products. Then, 4 Mg of residue at ISO C temperature was introduced into this reactor after distillation of crude esters containing 0.30% by weight of cobalt, 0.015% by weight of manganese and 0.0033% by weight of nickel. The contents of the reactor were mixed and held at a temperature of about 95 ° C for 30 minutes, then agitation was turned off and after 90 minutes the residue was collected at the bottom of the reactor. The acetate solution containing almost all of the cobalt, manganese and nickel was then subjected to concentration by applying 0.15 MPa steam to a heating coil. The condensed vapors from acetates were directed to the post-reaction water reservoir. From the initial quantity of salt, 3.6 mg of cobalt, manganese and nickel acetates were obtained after concentration of 0.25 mg of ootanes. The concentration of the sum of the catalyst metals was determined to be 4.58% by weight. To the thus obtained solution at a temperature of 50 ° C., 0.19 mg of methanol was added. Chromatographically determined analysis of the solution showed 3.4 wt% acetic acid. 0.65 wt.% Formic acid, 0.2 wt.% Formic and volatile aldehyde, 43 wt.% Methanol and 0.5 wt.% Other oxidation by-products. The cobalt content was determined to be 2.45% by weight, the manganese content was 0.12% by weight and the nickel content was 0.027% by weight. The prepared catalyst solution was directed to the catalyst solution storage tank located in the oxidation node of the two-lot erephallium plant. This solution was fed to the oxidation reactor in such an amount that the concentration of catalyst metals was 100 ppm. The obtained selectivity in terms of p-keylene and methyl p-toluate was 36% by weight. A sample of the concentrated catalyst solution after cooling to 25 ° C contained about 4.5% by weight of the sludge containing in addition to such compounds as p-toluate131 961 3 methyl, dimethyl terephthalate and p-toluic acid, monomethyl terephthalic acid and other approximately 30 weight components, mainly cobalt. Example II. Extraction of the catalyst components from the residue after distillation of crude esters was carried out as in Example 1, except that 3 mg of post-reaction water from the oxidation of p-xylene and p-methyl p-toluate were used for 4 mg of residue. The residue from the crude ester distillation used for extraction contained 0.49 wt.% Cobalt, 0.024 wt.% Manganese 1, 0.0054 wt.% Nickel. After extraction of the catalyst components and standing, the residue was removed from the bottom of the reactor, and the residue was almost devoid of catalyst saline. 3.8 mg of the residue after distillation of crude esters of the above composition was added to the same portion of the reaction water and extracted again. The analysis of the content of catalyst metals after the first extraction showed the content of 0.694 wt.% Of the total metals, including cobalt 0.654 wt.%, Manganese 0.033 wt.% And nickel 0.007 wt.%, And after the second extract, the total metal content was 1.453 wt.%. 15% by weight of methanol was added to the aqueous solution of catalyst metal acetates. The solution thus obtained with a total catalyst metal concentration of 1.262% by weight including cobalt 1.19% by weight, manganese 0.059% by weight and nickel 0.013% by weight was used as a catalyst in the process of oxidation of p-xylene and methyl p-toluate, obtaining a selectivity of 36.5%. Example III. 4 mg of reaction water from the oxidation of p-xylene and methyl p-toluate at a temperature of 40 ° C and composition as in the example of Ifa, then 4 mg of residues after distillation of crude esters at a temperature of 180 ° C were introduced. o the content of the catalyst components as in example I. After extraction of the catalyst components and standing, the residue was collected at the bottom of the reactor, and the analysis performed showed 0.316% by weight of the total metals of the catalyst components. To the same portion of reactive water after the first extract, 4 Mg of residual salt with the temperature of the 1st composition as above was added. During the extraction of the catalyst components, the temperature was held at 95 ° C., and after standing, the bottom residue was collected, and analysis of the acetates left in the extractor showed 0.6624 wt.% Of the total metals of the catalyst components. Another portion of 4 Mg of residual salt with the composition as above was added to the ora extract. Extraction of the catalyst components was carried out. After standing at the bottom of the reactor, the residue was collected, and 15% methanol (0.465 Mg) was added to 3.1 Mg of metal acetates of the catalyst components. The analyzes carried out showed 1.037% by weight of the total metals of the catalyst components before adding methanol, and 0.9016% by weight of methanol after adding methanol. including 0.8498 wt.% cobalt, 0.0425 wt.% manganese 1, 0.00935 wt.% nickel. The catalyst solution prepared in this way was directed to the catalyst solution storage tank and used in the oxidation of p-xylene and methyl p-toluate in ta- Kle-tilosoi so that the concentration of catalyst metals in the reaction mixture was 50 ppm. The obtained selectivity of the oxidation process of p-xylene and methyl p-toluate in terms of p-xylene was 36.5% by weight. Patent disclaimer. the process of producing dimethyl terephthalate by oxidation of p-xylene and methyl p-toluate and extraction of the catalyst components from the residue after distillation of the crude oil of these methyl esters with the reaction water from the oxidation process or with an aqueous solution of fatty acid, characterized in that 5-80% by weight of methyl alcohol is added to the recovered aqueous catalyst solution and the whole is recycled to the oxidation process. PL

Claims (1)

1. Zastrzezenie patentowe Sposób odzyskiwania 1 regeneraojl katalizatora utleniania w przemyslowym procesie wytwarzania dwumetylotereftalanu przez utlenianie p-ksylenu 1 p-toluilanu metylu i ekstrak¬ cje skladników katalizatora z pozostalosci po destylacji surowych estrów metylowych wodami reakoyjnyml poohodzacymi z procesu utleniania lub wodnym roztworem kwasu ootowego, zna¬ mienny tym, ze do odzyskanego wodnego roztworu katalizatora dodaje sie 5-80% wagowyoh alkoholu metylowego, po czym calosc zawraca sie do procesu utleniania. PL1. Patent claim The method of recovering 1 regeneration of the oxidation catalyst in the industrial process for the production of dimethyl terephthalate by oxidation of p-xylene and methyl p-toluate and extraction of the catalyst components from the residue after distillation of crude methyl esters with reaction water coming from the acid oxidation process or with aqueous acid, characterized in that 5-80% by weight of methyl alcohol is added to the recovered aqueous catalyst solution and the whole is recycled to the oxidation process. PL
PL1981230102A 1981-03-10 1981-03-10 Method of recovery and regeneration of catalyst of oxidation in industrial process of manufacture of dimethyl terephtalate PL131961B1 (en)

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