WO2010063619A1 - Installation de cristallisation d'acide adipique - Google Patents
Installation de cristallisation d'acide adipique Download PDFInfo
- Publication number
- WO2010063619A1 WO2010063619A1 PCT/EP2009/065758 EP2009065758W WO2010063619A1 WO 2010063619 A1 WO2010063619 A1 WO 2010063619A1 EP 2009065758 W EP2009065758 W EP 2009065758W WO 2010063619 A1 WO2010063619 A1 WO 2010063619A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- adipic acid
- solution
- austenitic stainless
- aisi
- stainless steel
- Prior art date
Links
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/0004—Crystallisation cooling by heat exchange
- B01D9/0013—Crystallisation cooling by heat exchange by indirect heat exchange
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
- C07C55/14—Adipic acid
Definitions
- the present invention relates to an adipic acid crystallization plant.
- Adipic acid is an important chemical compound used as a raw material in the synthesis of many compounds.
- adipic acid is an important intermediate compound in the synthesis of polyamides and more particularly of PA 6.6., As well as in the manufacture of polyesters and polyurethanes.
- Adipic acid is also used as an additive in many other applications such as the manufacture of plasticizers, for example.
- Adipic acid is generally synthesized from cyclohexane, by oxidation thereof to a cyclohexanone / cyclohexanol mixture and then nitric oxidation of this mixture to adipic acid.
- the nitric oxidation of the cyclohexanol / cyclohexanone mixture is carried out in the presence of a metal catalyst, the adipic acid being generally recovered and purified by successive crystallizations.
- the purification methods generally used implement crystallization steps conventionally consisting of concentrating and / or cooling the adipic acid solution to obtain the formation of pure adipic acid crystals.
- a crystallization plant may comprise several crystallizers mounted in series or an apparatus comprising several compartments for performing a continuous purification or several crystallizers operating in a batch process.
- the crystallizers are generally equipped with stirring means, means for cooling and / or concentrating the solution.
- the latter means may consist of devices placed in contact with the solution and in which circulates a heat transfer fluid, means for evaporating the solution in particular by placing under reduced pressure.
- the means for cooling and / or concentrating the solution may comprise several devices used alone or in combination, such as, for example, a jacket in the wall of the crystallizer, elements comprising means for circulating a coolant disposed in the solution or an external circulation circuit of the solution comprising a heat exchanger.
- This list of means for cooling and / or concentrating the solution is given for information only and is not limiting in nature.
- shielding depends on the nature of the material and the surface condition of the walls. More particularly, it will be favored by the difference in temperature between the solution and the walls in contact with the solution. Indeed, if this temperature difference is greater than a critical value depending on the concentration and temperature of the solution, the flow rate of the solution in the crystallizer, the nature of the material and surface state of the wall, a deposit of adipic acid occurs which adheres to the wall. The adipic acid deposit is also observed, regardless of the temperature difference on the walls whose surface state is degraded, especially in the case of crystallization by concentration of the solution obtained by pressurizing the crystallizer.
- the internal walls of the crystallizer and the walls of the device for cooling and / or concentrating the solution are polished to obtain a surface state with a minimum roughness. These polished surfaces can also be cleaned and washed by conventional cleaning techniques used in the field of metal surface treatment.
- the surface state of the walls can deteriorate rapidly under the effect of chemical corrosion, especially when the crystallization of adipic acid is carried out from the solutions obtained during the nitric oxidation of the cyclohexanone / cyclohexanol mixtures. Indeed, these solutions are acidic and contain a significant amount of nitric acid and / or nitrate ions.
- the crystallizers and the walls of the exchange devices are often made of austenitic stainless steel of the AISI 304L type. However, these phenomena of shielding and corrosion are still observed. The use of this type of material does not make it possible to eliminate or reduce the shutdowns of the installation to eliminate the shielding.
- the present invention proposes to overcome this problem to use for the manufacture of walls in contact with the adipic acid solution a material selected from particular stainless steel grades.
- the invention proposes an installation or crystallizer for the crystallization of adipic acid comprising a tank or crystallizer, stirring means and means for cooling and / or concentrating the adipic acid solution, characterized in that at least part of the walls in contact with the adipic acid solution and forming part of the tank or crystallizer and / or means for concentrating and / or cooling the solution is made of austenitic stainless steel of the AISI 310L type according to the AISI nomenclature (USA).
- the austenitic stainless steel type AISI 310L is also designated XlCrNi25-21 (1.4335) according to the European nomenclature.
- the means for cooling and / or concentrating the adipic acid solution consist of devices in contact with the solution. More particularly, devices comprising a circulation of coolant can be advantageously used to cool the solution.
- the walls of these cooling devices in contact with the adipic acid solution are made of austenitic stainless steel of the AISI 310L type.
- the parts of the plant such as the internal walls of the crystallizer, for example, are made of austenitic stainless steel type AISI 310L.
- the surfaces or walls made of austenitic stainless steel of the AISI 310L type are subjected to a polishing operation before being installed in the crystallizer.
- This polishing can be achieved by any known means using physical and / or chemical methods to reduce the roughness of the surface.
- the roughness of the surface is advantageous for the roughness of the surface to be less than 0.3 ⁇ m, measured according to the method defined by standards NF EN ISO 3274 and NF EN ISO 4288.
- the means for cooling and / or concentrating the adipic acid solution may be of various shapes such as coils, double-walled plates comprising a circulation of fluids or the like.
- the crystallizer of the invention is particularly suitable for crystallizing adipic acid from the solutions obtained at the exit of the nitric oxidation stage of the cyclohexanone / cyclohexanol mixture.
- the solution is maintained at a temperature of 90 ° C. under atmospheric pressure and is stirred for the entire duration of immersion. After 400 hours of immersion, the surface condition of the test pieces and the loss of thickness are determined. These specimens are again immersed for a new duration of 400 hours in the same medium. However, the solution is renewed before each new immersion.
- test pieces tested were made in two grades of stainless steel:
- Specimen 1 steel type AISI 304L
- Specimen 2 steel type AISI 310L
- Table I The composition of these steel grades is given in Table I below:
- test piece 2 which corresponds to the invention, has a roughness that varies very little over time compared to that measured for a type 304L steel. (test tube 1).
- This characteristic illustrates the fact that the use of a type 310L steel according to the invention makes it possible to maintain a good surface state over time for the reaction in question and thus to limit as much as possible the shielding phenomenon.
Abstract
Description
Claims
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US13/132,188 US9108121B2 (en) | 2008-12-01 | 2009-11-24 | Plant for the crystallization of adipic acid |
EP09756509.7A EP2358455B1 (fr) | 2008-12-01 | 2009-11-24 | Installation de cristallisation d'acide adipique |
CN2009801481218A CN102227243A (zh) | 2008-12-01 | 2009-11-24 | 用于己二酸结晶的设备 |
RU2011127008/04A RU2480262C2 (ru) | 2008-12-01 | 2009-11-24 | Установка для кристаллизации адипиновой кислоты |
SG2011039021A SG171449A1 (en) | 2008-12-01 | 2009-11-24 | Adipic acid crystallization equipment |
UAA201108300A UA107070C2 (uk) | 2008-12-01 | 2009-11-24 | Установка для кристалізації адипінової кислоти |
BRPI0916487A BRPI0916487B8 (pt) | 2008-12-01 | 2009-11-24 | equipamento de cristalização de ácido adípico |
ES09756509T ES2746499T3 (es) | 2008-12-01 | 2009-11-24 | Instalación de cristalización de ácido adípico |
KR1020147015028A KR20140085590A (ko) | 2008-12-01 | 2009-11-24 | 아디프산 결정화 장치 |
JP2011538955A JP5694181B2 (ja) | 2008-12-01 | 2009-11-24 | アジピン酸を結晶化させるための装置 |
PL09756509T PL2358455T3 (pl) | 2008-12-01 | 2009-11-24 | Instalacja do krystalizacji kwasu adypinowego |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0806729A FR2939052B1 (fr) | 2008-12-01 | 2008-12-01 | Installation de cristallisation d'acide adipique |
FR08/06729 | 2008-12-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2010063619A1 true WO2010063619A1 (fr) | 2010-06-10 |
Family
ID=40578483
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2009/065758 WO2010063619A1 (fr) | 2008-12-01 | 2009-11-24 | Installation de cristallisation d'acide adipique |
Country Status (13)
Country | Link |
---|---|
US (1) | US9108121B2 (fr) |
EP (1) | EP2358455B1 (fr) |
JP (2) | JP5694181B2 (fr) |
KR (2) | KR20110081329A (fr) |
CN (1) | CN102227243A (fr) |
BR (1) | BRPI0916487B8 (fr) |
ES (1) | ES2746499T3 (fr) |
FR (1) | FR2939052B1 (fr) |
PL (1) | PL2358455T3 (fr) |
RU (1) | RU2480262C2 (fr) |
SG (1) | SG171449A1 (fr) |
UA (1) | UA107070C2 (fr) |
WO (1) | WO2010063619A1 (fr) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113201419A (zh) * | 2020-01-31 | 2021-08-03 | 英威达纺织(英国)有限公司 | 用于己二酸至己二腈工艺设备的清洁方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4014903A (en) * | 1975-08-11 | 1977-03-29 | Allied Chemical Corporation | Recovery of dicarboxylic acids from aqueous solution containing nitric acid |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3607926A (en) * | 1969-03-18 | 1971-09-21 | Texaco Inc | Dicarboxylic acid manufacture |
DE3508532A1 (de) * | 1985-03-09 | 1986-09-18 | Bayer Ag, 5090 Leverkusen | Verwendung einer chromhaltigen legierung |
US5321157A (en) * | 1992-09-25 | 1994-06-14 | Redox Technologies Inc. | Process for the preparation of adipic acid and other aliphatic dibasic acids |
DE4342188C2 (de) * | 1993-12-10 | 1998-06-04 | Bayer Ag | Austenitische Legierungen und deren Verwendung |
US5472680A (en) * | 1994-01-26 | 1995-12-05 | E. I. Du Pont De Nemours And Company | Production of NO from N2 O |
DE19718088A1 (de) * | 1997-04-29 | 1998-11-05 | Basf Ag | Verfahren zur Kristallisation durch Verdampfung und Brüdenkondensation |
TWI238157B (en) * | 2001-01-25 | 2005-08-21 | Asahi Kasei Corp | Process for producing alkanedicarboxylic acid |
US7122083B2 (en) * | 2002-04-02 | 2006-10-17 | E. I. Du Pont De Nemours And Company | Apparatus and process used in growing crystals |
JP4494770B2 (ja) * | 2002-12-27 | 2010-06-30 | 住友化学株式会社 | 晶析方法および晶析装置 |
JP2004358351A (ja) * | 2003-06-04 | 2004-12-24 | Sumitomo Chem Co Ltd | 晶析方法 |
US6946572B2 (en) * | 2003-10-16 | 2005-09-20 | Invista North America S.A.R.L. | Crystallization of adipic acid from its solution in aqueous nitric acid |
JP2006298803A (ja) * | 2005-04-19 | 2006-11-02 | Mitsubishi Rayon Co Ltd | 光学活性α−ヒドロキシカルボン酸結晶の製造方法及び製造装置 |
JP4946071B2 (ja) * | 2006-01-20 | 2012-06-06 | 日本ゼオン株式会社 | 環状ケトン化合物の連続製造装置および連続製造方法。 |
JP2008271994A (ja) * | 2006-08-18 | 2008-11-13 | Daio Kensetsu Kk | 有機化合物の分解処理方法及びその装置 |
-
2008
- 2008-12-01 FR FR0806729A patent/FR2939052B1/fr not_active Expired - Fee Related
-
2009
- 2009-11-24 KR KR1020117012434A patent/KR20110081329A/ko active Application Filing
- 2009-11-24 EP EP09756509.7A patent/EP2358455B1/fr active Active
- 2009-11-24 US US13/132,188 patent/US9108121B2/en active Active
- 2009-11-24 WO PCT/EP2009/065758 patent/WO2010063619A1/fr active Application Filing
- 2009-11-24 ES ES09756509T patent/ES2746499T3/es active Active
- 2009-11-24 RU RU2011127008/04A patent/RU2480262C2/ru not_active IP Right Cessation
- 2009-11-24 PL PL09756509T patent/PL2358455T3/pl unknown
- 2009-11-24 CN CN2009801481218A patent/CN102227243A/zh active Pending
- 2009-11-24 SG SG2011039021A patent/SG171449A1/en unknown
- 2009-11-24 JP JP2011538955A patent/JP5694181B2/ja active Active
- 2009-11-24 UA UAA201108300A patent/UA107070C2/ru unknown
- 2009-11-24 BR BRPI0916487A patent/BRPI0916487B8/pt active IP Right Grant
- 2009-11-24 KR KR1020147015028A patent/KR20140085590A/ko not_active Application Discontinuation
-
2014
- 2014-10-17 JP JP2014212859A patent/JP2015017128A/ja not_active Abandoned
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4014903A (en) * | 1975-08-11 | 1977-03-29 | Allied Chemical Corporation | Recovery of dicarboxylic acids from aqueous solution containing nitric acid |
Non-Patent Citations (2)
Title |
---|
KACHANOV V A ET AL: "CORROSION OF WELD JOINTS IN THE MANUFACTURE OF ADIPIC ACID", PROTECTION OF METALS, PLENUM PUBLISHING CO, NEW YORK, US, vol. 17, no. 6, 1 November 1981 (1981-11-01), pages 599 - 602, XP009116448, ISSN: 0033-1732 * |
TSINMAN A I ET AL: "Corrosion of stainless steels in fused dicarboxylic acids", JOURNAL OF APPLIED CHEMISTRY OF USSR, CONSULTANTS BUREAU, NEW YORK, NY, US, vol. 38, no. 8, 1 August 1965 (1965-08-01), pages 1828 - 1831, XP009116445, ISSN: 0021-888X * |
Also Published As
Publication number | Publication date |
---|---|
KR20140085590A (ko) | 2014-07-07 |
JP2015017128A (ja) | 2015-01-29 |
BRPI0916487B8 (pt) | 2019-10-01 |
UA107070C2 (uk) | 2014-11-25 |
EP2358455A1 (fr) | 2011-08-24 |
PL2358455T3 (pl) | 2020-01-31 |
CN102227243A (zh) | 2011-10-26 |
JP5694181B2 (ja) | 2015-04-01 |
US9108121B2 (en) | 2015-08-18 |
JP2012510488A (ja) | 2012-05-10 |
RU2011127008A (ru) | 2013-01-10 |
KR20110081329A (ko) | 2011-07-13 |
FR2939052B1 (fr) | 2010-12-10 |
ES2746499T3 (es) | 2020-03-06 |
BRPI0916487A2 (pt) | 2016-02-16 |
US20110274591A1 (en) | 2011-11-10 |
FR2939052A1 (fr) | 2010-06-04 |
SG171449A1 (en) | 2011-07-28 |
EP2358455B1 (fr) | 2019-07-24 |
RU2480262C2 (ru) | 2013-04-27 |
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