CA2128719A1 - Production Method of High Purity Isomers of Benzenedicarboxylic Acids - Google Patents

Production Method of High Purity Isomers of Benzenedicarboxylic Acids

Info

Publication number
CA2128719A1
CA2128719A1 CA2128719A CA2128719A CA2128719A1 CA 2128719 A1 CA2128719 A1 CA 2128719A1 CA 2128719 A CA2128719 A CA 2128719A CA 2128719 A CA2128719 A CA 2128719A CA 2128719 A1 CA2128719 A1 CA 2128719A1
Authority
CA
Canada
Prior art keywords
oxidation
solvent
oxidized
extraction
post
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.)
Granted
Application number
CA2128719A
Other languages
French (fr)
Other versions
CA2128719C (en
Inventor
Vladimir D. Manzurov
Vladimir F. Nazimok
Nadezhda N. Goncharova
Valerij P. Yurjev
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hanwha Total Petrochemicals Co Ltd
Hanwha Impact Corp
Original Assignee
Hanwha General Chemicals Co Ltd
Samsung General Chemicals Co Ltd
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
Priority claimed from RU93046191/04A external-priority patent/RU2047595C1/en
Priority claimed from RU93046190/04A external-priority patent/RU2047594C1/en
Application filed by Hanwha General Chemicals Co Ltd, Samsung General Chemicals Co Ltd filed Critical Hanwha General Chemicals Co Ltd
Publication of CA2128719A1 publication Critical patent/CA2128719A1/en
Application granted granted Critical
Publication of CA2128719C publication Critical patent/CA2128719C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
    • C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/14—Monocyclic dicarboxylic acids
    • C07C63/15—Monocyclic dicarboxylic acids all carboxyl groups bound to carbon atoms of the six-membered aromatic ring
    • C07C63/26—1,4 - Benzenedicarboxylic acid

Abstract

Disclosed herein is a process for producing highly purified benzenedicarboxylic acid isomers without an additional catalytic reductive purification step, which comprises (a) an oxidation step wherein xylene isomer is oxidized with molecular oxygen or molecular oxygen containing gas in the presence of a catalyst system composed of cobalt, manganese, bromine and at least one selected from nickel; chrornium, zirconium and cerium in lower aliphatic carboxylic acid; and (b) an extraction/post-oxidation step wherein the oxidation product is crystallized to give cake of crude benzenedicarboxylic acid isomer, the cake is reslurried by adding lower aliphatic carboxylic acid solvent thereto followed by heating in order to extract impurities contained therein into the solvent, and the resulting slurry is oxidized with said catalyst system at a temperature of 2 - 80°C lower than that or said heating, each of said oxidation and extraction/post-oxidation being carried out once or twice, provided that any one or both of said steps should be carried out twice. According to the invention, the solvent employed to extract impurities is recycled from the subsequent oxidation steps.
CA002128719A 1993-09-28 1993-11-30 Production method of high purity isomers of benzenedicarboxylic acids Expired - Lifetime CA2128719C (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
RU93046191 1993-09-28
RU93046191/04A RU2047595C1 (en) 1993-09-28 1993-09-28 Process for preparing phthalic acid isomers having high purification degree
RU93046190/04A RU2047594C1 (en) 1993-09-28 1993-09-28 Process for preparing benzenedicarboxylic acid isomers having high purification degree
RU93046190 1993-09-28

Publications (2)

Publication Number Publication Date
CA2128719A1 true CA2128719A1 (en) 1995-03-29
CA2128719C CA2128719C (en) 1998-06-09

Family

ID=26653761

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002128719A Expired - Lifetime CA2128719C (en) 1993-09-28 1993-11-30 Production method of high purity isomers of benzenedicarboxylic acids

Country Status (21)

Country Link
US (1) US5359133A (en)
JP (1) JP3009223B2 (en)
KR (1) KR970000136B1 (en)
CN (1) CN1050118C (en)
AU (1) AU5576394A (en)
BE (1) BE1008546A4 (en)
BG (1) BG62324B1 (en)
BR (1) BR9305996A (en)
CA (1) CA2128719C (en)
DE (2) DE4397599C2 (en)
ES (1) ES2081265B1 (en)
FR (1) FR2710638B1 (en)
GB (1) GB2286588B (en)
IT (1) IT1271011B (en)
MY (1) MY108978A (en)
PL (1) PL175685B1 (en)
RO (1) RO113850B1 (en)
SA (1) SA94140587B1 (en)
SK (1) SK280582B6 (en)
TW (1) TW307753B (en)
WO (1) WO1995009143A1 (en)

Families Citing this family (78)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5929274A (en) * 1995-06-07 1999-07-27 Hfm International, Inc. Method to reduce carboxybenzaldehyde isomers in terephthalic acid or isophthalic acid
WO1996041791A1 (en) * 1995-06-08 1996-12-27 Mogilev Order Of Lenin Proizvodstvennoe Obiedinenie Method of obtaining terephthalic acid of monomeric purity
JP3757995B2 (en) * 1996-07-12 2006-03-22 三菱瓦斯化学株式会社 Method for producing high purity isophthalic acid
JP3341620B2 (en) * 1997-03-19 2002-11-05 株式会社日立製作所 Method and apparatus for producing aromatic polycarboxylic acid
KR100549107B1 (en) * 1999-04-28 2006-02-06 삼성토탈 주식회사 Production method of aromatic polycarboxylic acids
US6180822B1 (en) 1998-12-22 2001-01-30 Samsung General Chemical Co., Ltd. Method of producing aromatic carboxylic acids by oxidizing alkyl aromatic compounds or partially oxidized intermediates thereof with carbon dioxide containing gas
KR20000041506A (en) * 1998-12-22 2000-07-15 유현식 Method for the preparation of aromatic polycarbonic acid
US6194607B1 (en) 1998-12-22 2001-02-27 Samsung General Chemicals Co., Ltd. Method of producing aromatic carboxylic acids by oxidizing alkyl aromatic hydrocarbons or partially oxidized intermediates thereof
US6399790B1 (en) 1999-11-24 2002-06-04 General Electric Company Method for oxidation of xylene derivatives
US6465685B1 (en) 1999-11-24 2002-10-15 General Electric Company Method for oxidation of xylene derivatives
CN1207259C (en) 2000-01-18 2005-06-22 因卡国际公司 Oxidation of alkyl aromatic compounds to aromatic acids in an aqueous medium
US6657068B2 (en) 2002-03-22 2003-12-02 General Electric Company Liquid phase oxidation of halogenated ortho-xylenes
US6649773B2 (en) 2002-03-22 2003-11-18 General Electric Company Method for the manufacture of halophthalic acids and anhydrides
US6657067B2 (en) 2002-03-22 2003-12-02 General Electric Company Method for the manufacture of chlorophthalic anhydride
US7074954B2 (en) * 2002-12-09 2006-07-11 Eastman Chemical Company Process for the oxidative purification of terephthalic acid
CA2505977C (en) * 2002-12-09 2009-08-25 Eastman Chemical Company Process for the oxidative purification of terephthalic acid
AU2003293252A1 (en) * 2002-12-09 2004-06-30 Eastman Chemical Company Process for the oxidative purification of terephthalic acid
US7132566B2 (en) * 2003-09-22 2006-11-07 Eastman Chemical Company Process for the purification of a crude carboxylic acid slurry
US7161027B2 (en) * 2002-12-09 2007-01-09 Eastman Chemical Company Process for the oxidative purification of terephthalic acid
MXPA05006046A (en) * 2002-12-09 2005-08-18 Eastman Chem Co Process for the purification of a crude carboxylic acid slurry.
US7546747B2 (en) * 2004-01-15 2009-06-16 Eastman Chemical Company Process for production of a dried carboxylic acid cake suitable for use in polyester production
US7348452B2 (en) * 2004-04-22 2008-03-25 Eastman Chemical Company Liquid phase oxidation of P-xylene to terephthalic acid in the presence of a catalyst system containing nickel, manganese, and bromine atoms
US20050283022A1 (en) * 2004-06-18 2005-12-22 Sheppard Ronald B Filtrate preparation process for terephthalic acid filtrate treatment
US7541489B2 (en) 2004-06-30 2009-06-02 Sabic Innovative Plastics Ip B.V. Method of making halophthalic acids and halophthalic anhydrides
US7568361B2 (en) 2004-09-02 2009-08-04 Eastman Chemical Company Optimized liquid-phase oxidation
US7910769B2 (en) 2004-09-02 2011-03-22 Eastman Chemical Company Optimized liquid-phase oxidation
US7589231B2 (en) 2004-09-02 2009-09-15 Eastman Chemical Company Optimized liquid-phase oxidation
US7692037B2 (en) 2004-09-02 2010-04-06 Eastman Chemical Company Optimized liquid-phase oxidation
US7371894B2 (en) * 2004-09-02 2008-05-13 Eastman Chemical Company Optimized liquid-phase oxidation
WO2006028817A2 (en) * 2004-09-02 2006-03-16 Eastman Chemical Company Optimized liquid-phase oxidation
US7683210B2 (en) 2004-09-02 2010-03-23 Eastman Chemical Company Optimized liquid-phase oxidation
US7504535B2 (en) 2004-09-02 2009-03-17 Eastman Chemical Company Optimized liquid-phase oxidation
US7741515B2 (en) 2004-09-02 2010-06-22 Eastman Chemical Company Optimized liquid-phase oxidation
US7615663B2 (en) * 2004-09-02 2009-11-10 Eastman Chemical Company Optimized production of aromatic dicarboxylic acids
US7507857B2 (en) 2004-09-02 2009-03-24 Eastman Chemical Company Optimized liquid-phase oxidation
US7381836B2 (en) 2004-09-02 2008-06-03 Eastman Chemical Company Optimized liquid-phase oxidation
US7572936B2 (en) 2004-09-02 2009-08-11 Eastman Chemical Company Optimized liquid-phase oxidation
US7582793B2 (en) 2004-09-02 2009-09-01 Eastman Chemical Company Optimized liquid-phase oxidation
US7692036B2 (en) 2004-11-29 2010-04-06 Eastman Chemical Company Optimized liquid-phase oxidation
US7550627B2 (en) * 2005-03-08 2009-06-23 Eastman Chemical Company Processes for producing aromatic dicarboxylic acids
US20060205974A1 (en) * 2005-03-08 2006-09-14 Lavoie Gino G Processes for producing aromatic dicarboxylic acids
US7834208B2 (en) * 2005-05-19 2010-11-16 Eastman Chemical Company Process to produce a post catalyst removal composition
US7741516B2 (en) * 2005-05-19 2010-06-22 Eastman Chemical Company Process to enrich a carboxylic acid composition
US7919652B2 (en) * 2005-05-19 2011-04-05 Eastman Chemical Company Process to produce an enriched composition through the use of a catalyst removal zone and an enrichment zone
US7557243B2 (en) * 2005-05-19 2009-07-07 Eastman Chemical Company Enriched terephthalic acid composition
US20060264662A1 (en) * 2005-05-19 2006-11-23 Gibson Philip E Esterification of an enriched composition
US7432395B2 (en) * 2005-05-19 2008-10-07 Eastman Chemical Company Enriched carboxylic acid composition
US20060264656A1 (en) * 2005-05-19 2006-11-23 Fujitsu Limited Enrichment process using compounds useful in a polyester process
US20060264664A1 (en) * 2005-05-19 2006-11-23 Parker Kenny R Esterification of an exchange solvent enriched composition
US7880031B2 (en) * 2005-05-19 2011-02-01 Eastman Chemical Company Process to produce an enrichment feed
US7884231B2 (en) * 2005-05-19 2011-02-08 Eastman Chemical Company Process to produce an enriched composition
US7897809B2 (en) * 2005-05-19 2011-03-01 Eastman Chemical Company Process to produce an enrichment feed
US7884232B2 (en) 2005-06-16 2011-02-08 Eastman Chemical Company Optimized liquid-phase oxidation
US20070155987A1 (en) * 2006-01-04 2007-07-05 O'meadhra Ruairi S Oxidative digestion with optimized agitation
US20070179312A1 (en) * 2006-02-02 2007-08-02 O'meadhra Ruairi Seosamh Process for the purification of a crude carboxylic axid slurry
US20070208194A1 (en) * 2006-03-01 2007-09-06 Woodruff Thomas E Oxidation system with sidedraw secondary reactor
US7816556B2 (en) * 2006-03-01 2010-10-19 Eastman Chemical Company Polycarboxylic acid production system employing enhanced multistage oxidative digestion
US7772424B2 (en) * 2006-03-01 2010-08-10 Eastman Chemical Company Polycarboxylic acid production system employing enhanced evaporative concentration downstream of oxidative digestion
US7326808B2 (en) * 2006-03-01 2008-02-05 Eastman Chemical Company Polycarboxylic acid production system employing cooled mother liquor from oxidative digestion as feed to impurity purge system
US7393973B2 (en) * 2006-03-01 2008-07-01 Eastman Chemical Company Polycarboxylic acid production system with enhanced residence time distribution for oxidative digestion
US7501537B2 (en) * 2006-03-01 2009-03-10 Eastman Chemical Company Polycarboxylic acid production system employing oxidative digestion with reduced or eliminated upstream liquor exchange
US7888529B2 (en) * 2006-03-01 2011-02-15 Eastman Chemical Company Process to produce a post catalyst removal composition
US7326807B2 (en) * 2006-03-01 2008-02-05 Eastman Chemical Company Polycarboxylic acid production system with enhanced heating for oxidative digestion
US7420082B2 (en) * 2006-03-01 2008-09-02 Eastman Chemical Company Polycarboxylic acid production system employing hot liquor removal downstream of oxidative digestion
WO2008082501A1 (en) * 2006-12-21 2008-07-10 E.I. Du Pont De Nemours And Company Process for the synthesis of halogenated aromatic diacids
US8614350B2 (en) 2008-01-15 2013-12-24 Eastman Chemical Company Carboxylic acid production process employing solvent from esterification of lignocellulosic material
US8455680B2 (en) 2008-01-15 2013-06-04 Eastman Chemical Company Carboxylic acid production process employing solvent from esterification of lignocellulosic material
US8927764B2 (en) 2011-12-29 2015-01-06 Uop Llc Process for producing terephthalic acid
US9024059B2 (en) 2011-12-29 2015-05-05 Uop Llc Process for producing terephthalic acid
CN104011005A (en) * 2011-12-29 2014-08-27 环球油品公司 Process for producing terephthalic acid
US9085522B2 (en) 2011-12-29 2015-07-21 Uop Llc Process for producing terephthalic acid
US9045408B2 (en) 2011-12-29 2015-06-02 Uop Llc Process for oxidizing alkyl-aromatic compounds
US9156765B2 (en) 2011-12-29 2015-10-13 Uop Llc Process for oxidizing alkyl-aromatic compounds
US9212121B2 (en) * 2013-09-24 2015-12-15 Eastman Chemical Company Processes for producing terephthalic acid
US9199906B2 (en) 2013-09-24 2015-12-01 Eastman Chemical Company Processes for producing isophthalic acid
CN105688988B (en) * 2014-12-16 2018-11-27 财团法人工业技术研究院 Oxidation reaction catalyst for furfural compound and oxidation method for furfural compound
CN107954850A (en) * 2017-11-02 2018-04-24 华东理工大学 The preparation method of M-phthalic acid
CN107963964A (en) * 2017-11-02 2018-04-27 华东理工大学 The preparation method of M-phthalic acid

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1270030C2 (en) * 1962-04-27 1973-07-19 METHOD FOR PURIFYING TEREPHTHALIC ACID
US3595908A (en) * 1966-11-01 1971-07-27 Inst Francais Du Petrole Two-step oxidation of paraxylene for the production of terephthalic acid
DE1643721B1 (en) * 1967-12-22 1971-10-21 Basf Ag Process for the continuous production of benzene dicarboxylic acids
US3626001A (en) * 1968-05-09 1971-12-07 Atlantic Richfield Co Method for the production of high-purity isophthalic or terephthalic acid
US3683017A (en) * 1970-04-01 1972-08-08 Fmc Corp Oxidation of p-xylene and p-tolujc acid to terephthalic acid
JPS5518698B1 (en) * 1971-04-03 1980-05-21
US3845117A (en) * 1972-12-14 1974-10-29 Halcon International Inc Process for preparation of phthalic acids
US3920735A (en) * 1973-05-21 1975-11-18 Standard Oil Co Zirconium enhanced activity of transition metal-bromine catalysis of di- and trimethyl benzene oxidation in liquid phase
JPS5291835A (en) * 1976-01-29 1977-08-02 Mitsubishi Chem Ind Ltd Prepation of terephtalic acid for direct polymerization
US4201871A (en) * 1978-02-23 1980-05-06 Asahi Kasei Kogyo Kabushiki Kaisha Process for recovering terephthalic acid
JPS5555138A (en) * 1978-10-19 1980-04-22 Mitsubishi Chem Ind Ltd Preparation of highly pure terephthalic acid
EP0021747B1 (en) * 1979-07-02 1983-05-18 Imperial Chemical Industries Plc Process for the preparation of terephthalic acid
US4334086A (en) * 1981-03-16 1982-06-08 Labofina S.A. Production of terephthalic acid
JPS57200328A (en) * 1981-06-03 1982-12-08 Mitsubishi Chem Ind Ltd Preparation of terephthalic acid
JPS59104345A (en) * 1982-12-03 1984-06-16 Kuraray Yuka Kk Production of terephthalic acid suitable for direct polymerization
JPS59106435A (en) * 1982-12-10 1984-06-20 Mitsubishi Chem Ind Ltd Production of high-purity terephthalic acid
JPS60233032A (en) * 1984-05-04 1985-11-19 Kuraray Yuka Kk Production of terephthalic acid suitable for direct polymerization
US4892970A (en) * 1985-12-30 1990-01-09 Amoco Corporation Staged aromatics oxidation in aqueous systems
JPH0662495B2 (en) * 1986-05-16 1994-08-17 三菱化成株式会社 Manufacturing method of high-purity terephthalic acid
JP2504461B2 (en) * 1987-04-24 1996-06-05 三菱化学株式会社 Manufacturing method of high quality terephthalic acid
US4786753A (en) * 1987-05-18 1988-11-22 Amoco Corporation Oxidation process for the manufacture of aromatic acids from alkylaromatic compounds
DE69104280T2 (en) * 1990-06-25 1995-02-16 Mitsubishi Gas Chemical Co Process for the production of high-purity isophthalic acid.
CA2050866A1 (en) * 1990-09-10 1992-03-11 George F. Schaefer Oxidation of dialkyl polyaromatics to dicarboxypolyaromatics
JP3231134B2 (en) * 1993-05-11 2001-11-19 住友化学工業株式会社 Particle measuring method and device therefor

Also Published As

Publication number Publication date
KR970000136B1 (en) 1997-01-04
CN1103860A (en) 1995-06-21
RO113850B1 (en) 1998-11-30
JP3009223B2 (en) 2000-02-14
BG62324B1 (en) 1999-08-31
BE1008546A4 (en) 1996-06-04
ITMI941879A0 (en) 1994-09-14
PL175685B1 (en) 1999-01-29
DE4397599T1 (en) 1997-07-24
TW307753B (en) 1997-06-11
GB9415915D0 (en) 1995-05-24
AU5576394A (en) 1995-04-18
ES2081265B1 (en) 1996-10-16
CN1050118C (en) 2000-03-08
IT1271011B (en) 1997-05-26
ITMI941879A1 (en) 1996-03-14
GB2286588B (en) 1996-09-11
MY108978A (en) 1996-11-30
BG98919A (en) 1995-05-31
BR9305996A (en) 1997-10-21
PL308537A1 (en) 1995-08-21
GB2286588A (en) 1995-08-23
SK87794A3 (en) 1995-05-10
US5359133A (en) 1994-10-25
CA2128719C (en) 1998-06-09
SA94140587B1 (en) 2006-11-12
KR950008467A (en) 1995-04-17
WO1995009143A1 (en) 1995-04-06
DE4397599C2 (en) 1998-02-19
ES2081265A1 (en) 1996-02-16
FR2710638B1 (en) 1996-04-26
JPH08506571A (en) 1996-07-16
FR2710638A1 (en) 1995-04-07
SK280582B6 (en) 2000-04-10

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