US20040215036A1 - Method for heating a crude carboxylic acid slurry in a post oxidation zone by the addition of steam - Google Patents

Method for heating a crude carboxylic acid slurry in a post oxidation zone by the addition of steam Download PDF

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Publication number
US20040215036A1
US20040215036A1 US10/423,389 US42338903A US2004215036A1 US 20040215036 A1 US20040215036 A1 US 20040215036A1 US 42338903 A US42338903 A US 42338903A US 2004215036 A1 US2004215036 A1 US 2004215036A1
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United States
Prior art keywords
post oxidation
product
zone
carboxylic acid
post
Prior art date
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Abandoned
Application number
US10/423,389
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English (en)
Inventor
Robert Lin
Marcel de Vreede
John Sluijmers
Martin de Boer
Thomas Woodruff
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Eastman Chemical Co
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Eastman Chemical Co
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 Eastman Chemical Co filed Critical Eastman Chemical Co
Priority to US10/423,389 priority Critical patent/US20040215036A1/en
Assigned to EASTMAN CHEMICAL COMPANY reassignment EASTMAN CHEMICAL COMPANY ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: DE VREEDE, MARCEL, LIN, ROBERT, WOODRUFF, THOMAS EARL, DE BOER, MARTIN, SLUIJMERS, JOHN WILHELMUS
Priority to KR1020057020195A priority patent/KR20060006938A/ko
Priority to JP2006532432A priority patent/JP2006528682A/ja
Priority to RU2005136662/04A priority patent/RU2005136662A/ru
Priority to EP04785490A priority patent/EP1620385A1/en
Priority to MXPA05011302A priority patent/MXPA05011302A/es
Priority to CA002522440A priority patent/CA2522440A1/en
Priority to PCT/US2004/012076 priority patent/WO2004103945A1/en
Priority to CNA2004800111371A priority patent/CN1780806A/zh
Priority to BRPI0409500-6A priority patent/BRPI0409500A/pt
Priority to ARP040101326A priority patent/AR043893A1/es
Publication of US20040215036A1 publication Critical patent/US20040215036A1/en
Priority to US11/254,406 priority patent/US7342128B2/en
Abandoned legal-status Critical Current

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    • 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
    • C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
    • 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
    • C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
    • C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
    • C07C51/46—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation by azeotropic distillation
    • 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

Definitions

  • the present invention relates to a process for heating carboxylic acid slurry in a post oxidation zone by the addition of steam. More specifically, the present invention relates to a process for heating a terephthalic acid slurry in a post oxidation zone by the addition of steam in a process for the production of a crystallized product.
  • Terephthalic acid is commercially produced by oxidation of paraxylene in the presence of a catalyst, such as, for example, Co, Mn, Br and a solvent.
  • a catalyst such as, for example, Co, Mn, Br and a solvent.
  • Terephthalic acid used in the production of polyester fibers, films, and resins must be further treated to remove impurities present due to the initial oxidation of paraxylene.
  • Typical commercial processes remove impurities by isolating a crude terephthalic acid solid, dissolving the solid in water at high temperatures and pressures, hydrogenating the resultant solution, cooling and crystallizing the terephthalic acid product out of solution, and separating the solid terephthalic product from the liquid as discussed in U. S. Pat. No.
  • a method of producing a terephthalic acid product suitable for polyester production is to completely or nearly completely react paraxylene in a multiple stage oxidation process.
  • a unique and novel process is provided wherein a crude terephthaic slurry produced by the oxidation of an aromatic feedstock, typically p-xylene, is further oxidized in a multiple step process wherein heat is provided to a post oxidation zone by steam addition. The addition of steam to an oxidation zone subsequent to the primary oxidation zone results in a higher quality terephthalic acid product compared to conventional techniques.
  • This invention provides a process to produce a crystallized product from a crude carboxylic acid slurry by injecting steam in a post oxidation zone subsequent to the primary oxidation zone.
  • a process to produce a crystallized product comprises oxidizing in a post oxidation zone a crude carboxylic acid slurry in the presence of steam to form the post oxidation product; wherein the crude carboxylic acid slurry comprises terephthalic acid; wherein the post oxidation zone comprises at least one post oxidation device; wherein the post oxidation product has a b* color of less than about 4.5.
  • a process to produce a crystallized product comprises the following steps:
  • FIG. 1 is a schematic of a process for heating a crude carboxylic acid slurry in a post oxidation zone by the addition of steam to produce a post oxidation product.
  • the present invention provides a process to produce a post oxidation product comprising oxidizing a crude carboxylic acid slurry in the presence of steam to form the post oxidation product 120 and a offgas stream 80 .
  • a process to produce a post oxidation product 120 comprises oxidizing in a post oxidation zone 90 a crude carboxylic acid slurry 30 in the presence of steam 100 to form the post oxidation product 120 and an offgas stream 80 ; wherein the post oxidation zone 90 - comprises at least one post oxidation device; wherein the carboxylic acid slurry comprises at least one carboxylic acid; and wherein the post oxidation product 120 has a b* color of less than 4.5.
  • a process to produce a crystallized product 180 is provided as shown in FIG. 1.
  • the process comprises the following steps.
  • Step (a) comprises oxidizing the crude carboxylic acid slurry 30 in a post oxidation zone 90 in the presence of steam 100 to form a post oxidation product 120 .
  • the crude carboxylic acid slurry 30 is produced by oxidizing in a primary oxidation zone 20 an aromatic feed stock 10 .
  • the primary oxidation zone 20 comprises at least one oxidation reactor, and the crude carboxylic acid slurry 30 comprises at least one carboxylic acid.
  • the oxidizing in the primary oxidation zone 20 is completed under reaction conditions, which produces a crude carboxylic acid slurry 30 from an aromatic feedstock 10 .
  • the crude carboxylic acid slurry 30 comprises at least one carboxylic acid.
  • the carboxylic acid is terephthalic acid.
  • the crude carboxylic acid slurry 30 would be referred to as crude terephthalic acid slurry.
  • suitable carboxylic acids include, but are not limited to, terephthalic acid, isophthalic acid, naphthalene dicarboxylic acid, and mixtures thereof.
  • Crude terephthalic acid slurry is conventionally synthesized via the liquid phase oxidation of paraxylene in the presence of metal oxidation catalyst.
  • Suitable catalysts include, but are not limited to, cobalt, manganese and bromide compounds, which are soluble in the selected solvent.
  • Suitable solvents include, but are not limited to, aliphatic mono-carboxylic acids, preferably containing 2 to 6 carbon atoms, or benzoic acid and mixtures thereof and mixtures of these compounds with water.
  • the solvent is acetic acid mixed with water in a ratio of about 5:1 to about 25:1, preferably between about 10:1 and about 15:1.
  • suitable solvents such as those disclosed herein, may also be utilized.
  • the primary oxidation zone 20 has a water concentration less than about 10 wt %, preferably the water concentration is less than about 8 wt %, and most preferably the water concentration is less than about 6 wt %.
  • the post oxidation zone 90 comprises at least one post oxidation device.
  • the crude carboxylic acid slurry 30 is fed to the post oxidation zone 90 .
  • the post oxidation zone 90 comprises at least one post oxidation device.
  • post oxidation means that the oxidation occurs after the primary oxidation zone 20 discussed previously.
  • the post oxidation zone 90 can comprise post oxidation devices in series.
  • the crude carboxylic acid slurry 30 in the post oxidation device is heated with steam 100 to between about 180° C. and about 280° C., preferably between about 190° C. and about 240° C., and most preferably between 195° C. to 215° C. and further oxidized with air or a source of molecular oxygen fed by line 115 to produce a post oxidation product 120 .
  • the temperature is the internal temperature of the post oxidation device.
  • the post oxidation zone comprises more than one post oxidation device, the temperature can vary within the specified range for each post oxidation device.
  • the steam 100 can be fed in the post oxidation zone 90 by any means known in the art.
  • a connection can be made for the steam 100 to be directly fed to the acetic acid vapor line. So the steam could be injected into the digester through the sparge ring.
  • the post oxidation zone 90 can be heated with acetic acid vapor.
  • Additional air or molecular oxygen may be fed to the post oxidation zone 90 in an amount necessary to oxidize a substantial portion of the partially oxidized products and 4-carboxybenzaldehyde (4-CBA) in the crude carboxylic acid slurry 30 to the corresponding carboxylic acid.
  • 4-CBA 4-carboxybenzaldehyde
  • terephthalic acid in the post oxidation zone 90
  • at least 80% by weight of the 4-CBA is converted to terephthalic acid in the post oxidation zone 90 .
  • Typical terephthalic acid product contains on a weight basis less than 500 parts per million (ppm) 4-carboxybenzaldehyde and less than 250 ppm p-toluic acid.
  • the post oxidation zone is operated at a temperature and pressure sufficient that the b* color of the post oxidation product 120 ranges from about 0.5 to about 4.5.
  • Step (b) comprises purifying the post oxidation product before or after a crystallization zone to form a decolorized post oxidation product having b* color of less than 4.5.
  • the purifying of the post oxidation product can be accomplished by any means known in the art.
  • colored impurities from the benzil, anthroquinone, and fluorenone families can be hydrogenated to colorless products.
  • any amount of process steps can be between the post oxidation zone and the purifying of the post oxidation product and the isolation or recovery of the post oxidation product if desired.
  • the b* color of the post oxidation product in conduit 180 is between about 0.5 to about 4.5.
  • the b* color of the decolorized post oxidation product in conduit 120 is between 0.5 to 2.0.
  • the b* color in the decolorized post oxidation product in conduit 120 is between 0.5 to 1.5.
  • the b* color is one of the three-color attributes measured on a spectroscopic reflectance-based instrument. The color can be measured by any device known in the art. A Hunter Ultrascan XE instrument is typically the measuring device. Positive readings signify the degree of yellow (or absorbance of blue), while negative readings signify the degree of blue (or absorbance of yellow).
  • Offgas from the post oxidation zone is withdrawn via line 80 and fed to a recovery system where the solvent is removed from the offgas.
  • the solvent comprising volatile organic compounds (VOCs).
  • VOCs and any hazardous pollutants may be incinerated.
  • Step (c) comprises crystallizing the post oxidation product 120 in the crystallization zone 160 to form a crystallized product 180 ; wherein the crystallized product 180 has a b* color of less than 4.5.
  • the crystallization zone 160 comprises at least one crystallizer. Vapor product from the crystallization zone 160 is withdrawn via line 130 , condensed in a condenser zone 170 , which comprises at least one condenser and returned to the crystallization zone 160 .
  • the liquid in conduit 140 or vapor 130 in the condenser zone 170 can be recycled, or it can be withdrawn or sent to an energy recovery device.
  • the liquid crystallization offgas 150 from the condenser zone 170 is removed via line 150 and can be routed to a recovery system where the solvent is removed and crystallization offgas 150 comprising VOCs and pollutants are burned.
  • the post oxidation product 120 from the post oxidation zone 90 is withdrawn via line 120 and fed to a crystallization zone 160 comprising at least one crystallizer where it is cooled to a temperature between about 110° C. and about 190° C. to form a crystallized product 180 , preferably to a temperature between about 140° C. to about 180° C., most preferably 150° C. to 170° C.
  • the b* color of the crystallized product in conduit 180 is between about 0.5 to about 4.5. More preferably, the b* color of the crystallized product in conduit 135 is between 0.5 to 2.0. Most preferably, the b* color in the crystallized product in conduit 135 is between 0.5 to 1.5
  • the crystallized product 180 from the crystallization zone 160 is withdrawn via line 180 .
  • the crystallized product 180 is then fed directly to a vessel and cooled to form a cooled crystallized product.
  • the cooled crystallized product is cooled in a vessel to typically a temperature of approximately 90° C. or less than before being introduced into a process for recovering the carboxylic acid as a dry powder or wet cake.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US10/423,389 2003-04-25 2003-04-25 Method for heating a crude carboxylic acid slurry in a post oxidation zone by the addition of steam Abandoned US20040215036A1 (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
US10/423,389 US20040215036A1 (en) 2003-04-25 2003-04-25 Method for heating a crude carboxylic acid slurry in a post oxidation zone by the addition of steam
BRPI0409500-6A BRPI0409500A (pt) 2003-04-25 2004-04-19 processos para produzir um produto de pós oxidação e um produto cristalizado
CA002522440A CA2522440A1 (en) 2003-04-25 2004-04-19 A purification process of crude terephthalic acid in a post oxidation zone by the addition of steam
JP2006532432A JP2006528682A (ja) 2003-04-25 2004-04-19 水蒸気添加による後酸化ゾーンでの粗原料カルボン酸スラリーの加熱方法
RU2005136662/04A RU2005136662A (ru) 2003-04-25 2004-04-19 Способ очистки сырой терефталевой кислоты в зоне последующего окисления путем введения водяного пара
EP04785490A EP1620385A1 (en) 2003-04-25 2004-04-19 A purification process of crude terephtalic acid in a post oxidation zone by the addition of steam
MXPA05011302A MXPA05011302A (es) 2003-04-25 2004-04-19 Proceso de purificacion de acido tereftalico crudo en una zona post oxidacion por la adicion de corriente.
KR1020057020195A KR20060006938A (ko) 2003-04-25 2004-04-19 후 산화 대역에서 증기의 첨가에 의한 조질의 테레프탈산의정제방법
PCT/US2004/012076 WO2004103945A1 (en) 2003-04-25 2004-04-19 A purification process of crude terephthalic acid in a post oxidation zone by the addition of steam
CNA2004800111371A CN1780806A (zh) 2003-04-25 2004-04-19 在后氧化区通过水蒸汽的添加对粗品对苯二酸进行纯化的方法
ARP040101326A AR043893A1 (es) 2003-04-25 2004-04-20 Un metodo para calentar una suspension de acido carboxilico cruda en una zona de posoxidacion mediante la adicion de vapor
US11/254,406 US7342128B2 (en) 2003-04-25 2005-10-20 Method for oxidizing a slurry composition in a post oxidation zone in the presence of added steam

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Application Number Priority Date Filing Date Title
US10/423,389 US20040215036A1 (en) 2003-04-25 2003-04-25 Method for heating a crude carboxylic acid slurry in a post oxidation zone by the addition of steam

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US11/254,406 Continuation-In-Part US7342128B2 (en) 2003-04-25 2005-10-20 Method for oxidizing a slurry composition in a post oxidation zone in the presence of added steam

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US10/423,389 Abandoned US20040215036A1 (en) 2003-04-25 2003-04-25 Method for heating a crude carboxylic acid slurry in a post oxidation zone by the addition of steam
US11/254,406 Expired - Lifetime US7342128B2 (en) 2003-04-25 2005-10-20 Method for oxidizing a slurry composition in a post oxidation zone in the presence of added steam

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US (2) US20040215036A1 (ru)
EP (1) EP1620385A1 (ru)
JP (1) JP2006528682A (ru)
KR (1) KR20060006938A (ru)
CN (1) CN1780806A (ru)
AR (1) AR043893A1 (ru)
BR (1) BRPI0409500A (ru)
CA (1) CA2522440A1 (ru)
MX (1) MXPA05011302A (ru)
RU (1) RU2005136662A (ru)
WO (1) WO2004103945A1 (ru)

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US20040037633A1 (en) * 2002-02-14 2004-02-26 Dr. Jorg Guhring Heavy-duty coupling for tool holder arms of modular design
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US20050283022A1 (en) * 2004-06-18 2005-12-22 Sheppard Ronald B Filtrate preparation process for terephthalic acid filtrate treatment
US20060047149A1 (en) * 2004-09-02 2006-03-02 De Vreede Marcel Optimized liquid-phase oxidation
US20060047152A1 (en) * 2004-09-02 2006-03-02 Wonders Alan G Optimized liquid-phase oxidation
US20060128987A1 (en) * 2002-12-09 2006-06-15 Sheppard Ronald B Process for the oxidative purification of terephthalic acid
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
US20070208191A1 (en) * 2006-03-01 2007-09-06 Wonders Alan G Polycarboxylic acid production system employing enhanced multistage oxidative digestion
US20070208190A1 (en) * 2006-03-01 2007-09-06 Wonders Alan G Polycarboxylic acid production system employing oxidative digestion with reduced or eliminated upstream liquor exchange
US20070208192A1 (en) * 2006-03-01 2007-09-06 Wonders Alan G Polycarboxylic acid production system employing hot liquor removal downstream of oxidative digestion
US20070208194A1 (en) * 2006-03-01 2007-09-06 Woodruff Thomas E Oxidation system with sidedraw secondary reactor
US20070208193A1 (en) * 2006-03-01 2007-09-06 Wonders Alan G Polycarboxylic acid production system employing cooled mother liquor from oxidative digestion as feed to impurity purge system
US20070219392A1 (en) * 2006-03-01 2007-09-20 Alan George Wonders Polycarboxylic acid production system with enhanced heating for oxidative digestion
US20070219393A1 (en) * 2006-03-01 2007-09-20 Robert Lin Polycarboxylic acid production system with enhanced residence time distribution for oxidative digestion
US20070244340A1 (en) * 2006-03-01 2007-10-18 Alan George Wonders Polycarboxylic acid production system employing enhanced evaporative concentration downstream of oxidative digestion
US7659427B2 (en) 2004-09-02 2010-02-09 Eastman Chemical Company Optimized liquid-phase oxidation
US7683210B2 (en) 2004-09-02 2010-03-23 Eastman Chemical Company Optimized liquid-phase oxidation
US7692037B2 (en) 2004-09-02 2010-04-06 Eastman Chemical Company Optimized liquid-phase oxidation
US7692036B2 (en) 2004-11-29 2010-04-06 Eastman Chemical Company Optimized liquid-phase oxidation
US7884232B2 (en) 2005-06-16 2011-02-08 Eastman Chemical Company Optimized liquid-phase oxidation
US7901636B2 (en) 2004-09-02 2011-03-08 Eastman Chemical Company Optimized liquid-phase oxidation
US7910071B2 (en) 2004-09-02 2011-03-22 Eastman Chemical Company Optimized liquid-phase oxidation
US7910769B2 (en) 2004-09-02 2011-03-22 Eastman Chemical Company Optimized liquid-phase oxidation
US7960581B2 (en) 2004-09-02 2011-06-14 Grupo Petrotemex, S.A. De C.V. Optimized liquid-phase oxidation
US7977505B2 (en) 2004-09-02 2011-07-12 Eastman Chemical Company Optimized liquid-phase oxidation
US8114356B2 (en) 2004-09-02 2012-02-14 Grupo Pretrotemex, S.A. de C.V. Optimized liquid-phase oxidation
US8470257B2 (en) 2004-09-02 2013-06-25 Grupo Petrotemex, S.A. De C.V. Optimized liquid-phase oxidation
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