EP2364286A1 - Verfahren zur herstellung von adipinsäure - Google Patents

Verfahren zur herstellung von adipinsäure

Info

Publication number
EP2364286A1
EP2364286A1 EP09759959A EP09759959A EP2364286A1 EP 2364286 A1 EP2364286 A1 EP 2364286A1 EP 09759959 A EP09759959 A EP 09759959A EP 09759959 A EP09759959 A EP 09759959A EP 2364286 A1 EP2364286 A1 EP 2364286A1
Authority
EP
European Patent Office
Prior art keywords
adipic acid
devices
stainless steel
nitric
x2crnin23
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.)
Withdrawn
Application number
EP09759959A
Other languages
English (en)
French (fr)
Inventor
Philippe Carvin
Fabien Bellenger
Serge Crottier-Combe
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.)
Rhodia Operations SAS
Original Assignee
Rhodia Operations SAS
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 Rhodia Operations SAS filed Critical Rhodia Operations SAS
Publication of EP2364286A1 publication Critical patent/EP2364286A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22C—ALLOYS
    • C22C38/00—Ferrous alloys, e.g. steel alloys
    • C22C38/02—Ferrous alloys, e.g. steel alloys containing silicon
    • 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
    • C07C51/27—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with oxides of nitrogen or nitrogen-containing mineral acids
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/02—Apparatus characterised by being constructed of material selected for its chemically-resistant properties
    • 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
    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22C—ALLOYS
    • C22C38/00—Ferrous alloys, e.g. steel alloys
    • C22C38/001—Ferrous alloys, e.g. steel alloys containing N
    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22C—ALLOYS
    • C22C38/00—Ferrous alloys, e.g. steel alloys
    • C22C38/04—Ferrous alloys, e.g. steel alloys containing manganese
    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22C—ALLOYS
    • C22C38/00—Ferrous alloys, e.g. steel alloys
    • C22C38/18—Ferrous alloys, e.g. steel alloys containing chromium
    • C22C38/40—Ferrous alloys, e.g. steel alloys containing chromium with nickel
    • C22C38/42—Ferrous alloys, e.g. steel alloys containing chromium with nickel with copper
    • C—CHEMISTRY; METALLURGY
    • C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
    • C22C—ALLOYS
    • C22C38/00—Ferrous alloys, e.g. steel alloys
    • C22C38/18—Ferrous alloys, e.g. steel alloys containing chromium
    • C22C38/40—Ferrous alloys, e.g. steel alloys containing chromium with nickel
    • C22C38/44—Ferrous alloys, e.g. steel alloys containing chromium with nickel with molybdenum or tungsten
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/02—Apparatus characterised by their chemically-resistant properties
    • B01J2219/0204—Apparatus characterised by their chemically-resistant properties comprising coatings on the surfaces in direct contact with the reactive components
    • B01J2219/0236—Metal based
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/02—Apparatus characterised by their chemically-resistant properties
    • B01J2219/025—Apparatus characterised by their chemically-resistant properties characterised by the construction materials of the reactor vessel proper
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/02—Apparatus characterised by their chemically-resistant properties
    • B01J2219/025—Apparatus characterised by their chemically-resistant properties characterised by the construction materials of the reactor vessel proper
    • B01J2219/0277—Metal based
    • B01J2219/0286—Steel

Definitions

  • the present invention relates to a method of manufacturing adipic acid used in devices made of material resistant to corrosion of the synthesis medium.
  • Adipic acid is an important chemical compound used as a raw material for many products and applications.
  • adipic acid is used as an intermediate for the synthesis of macromolecular compounds such as polyamides, more particularly PA6-6, polyesters, polyurethanes, for example.
  • This article is also used for the manufacture of plasticizer or as additives.
  • adipic acid Several processes for the manufacture of adipic acid are known and exploited industrially.
  • the main method used industrially is to oxidize cyclohexane with oxygen to obtain cyclohexanol and cyclohexanone intermediates, generally a mixture of these two compounds.
  • the intermediate compounds, cyclohexanol / cyclohexanone are oxidized to adipic acid with nitric acid in the presence of a catalyst.
  • the adipic acid is recovered and purified by the usual techniques and preferably by crystallization.
  • nitric oxidation reaction of the intermediate compounds is carried out in devices and reactors to resist nitric corrosion.
  • these devices and reactors are constructed of special steels marketed for their resistance to nitric corrosion.
  • the adipic acid is purified in particular during a crystallization step to obtain adipic acid crystals.
  • the crystallization of adipic acid is carried out from solutions obtained during the nitric oxidation of cyclohexanone / cyclohexanol mixtures. These solutions are acidic and contain a significant amount of nitric acid and / or nitrate ions.
  • This shielding requires the periodic shutdown of the process to remove adipic acid deposits on the heat exchange walls or the walls of the crystallizer.
  • the surface state is measured in particular by the surface roughness of the material, for example according to the method defined by standards NF EN ISO 3274 and NF EN ISO 4288.
  • One of the aims of the present invention is to remedy these drawbacks by proposing to carry out the step of manufacturing adipic acid, namely the nitric oxidation of the cyclohexanone and cyclohexanol compounds in devices and reactors constructed of a material limiting the corrosion phenomenon and thus decreasing the presence of impurities in the adipic acid product.
  • Another aim is to limit the phenomenon of shielding the walls of the crystallization devices with adipic acid.
  • the invention proposes a method for manufacturing adipic acid comprising a step of oxidation with nitric acid of cyclohexanol / cyclohexanone compounds implemented in an installation comprising at least one reactor and devices or apparatus, characterized in that at least the parts of the reactor in contact with the nitric oxidation reaction medium and, optionally, parts of the devices and / or apparatus are made of a material called a duplex stainless steel austenitic ferritic type X2 CrNiN23-4 (1.4362) according to the European nomenclature. These steels may be marketed under the trade names URANUS 35N or SAF 2304.
  • the devices or reactors can be made completely with stainless steel austenitic-ferritic said duplex type X2 CrNiN23-4 or only partially with this material.
  • the parts made of austeno-ferritic stainless steel said duplex X2 CrNiN23-4 are those coming into contact with the reaction medium or the vapors and gases from this reaction medium.
  • the austeno-ferritic stainless steel said duplex type X2 CrNiN23-4 is a material whose composition is defined in standards NF EN 10088-1 (formerly NFA35-574) and NF EN 10028-7 applicable in their latest revision.
  • the nitric oxidation medium of cyclohexanol and / or cyclohexanone comprises metal compounds.
  • the nitric oxidation medium of cyclohexanol and / or cyclohexanone comprises nitric acid at a concentration advantageously of between 20 and 35% by weight, metal compounds forming the nitric oxidation catalyst and metal compounds present in cyclohexanol. and / or cyclohexanone and corresponding to the catalysts used in the oxidation of cyclohexane by oxygen or the decomposition of hydroxycyclohexyl peroxide.
  • the nitric oxidation reaction is carried out at a temperature of between 70 and 120 ° C., and advantageously between 70 and 100 ° C., generally under an absolute pressure of between 1 bar and 5 bars.
  • the reactors used for carrying out the nitric oxidation are constructed of so-called duplex stainless steel austenitic ferritic type X2 CrNiN23-4. It is also advantageous to make the other devices and devices of the installation with this material austenitic-ferritic stainless steel said duplex type X2 CrNiN23-4.
  • the process of the invention comprises a step of crystallization of adipic acid
  • the devices or apparatus comprise a crystallization tank equipped with stirring means, cooling means and / or concentration of the solution of adipic acid.
  • adipic acid and at least a part of the walls of the crystallization vessel and / or cooling means and / or concentration in contact with the adipic acid solution is made of stainless steel austenitic-ferritic said duplex type X2CrNiN23- 4 (1.4362) according to the European nomenclature.
  • 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 X2CrNiN23-4 (Uranus 35N equivalent or SAF2304) The composition of these steel grades is given in Table I below:
  • test piece 2 which corresponds to the invention, has a roughness which varies very little over time compared with that measured for a steel of type AISI 304L (test piece 1) and which remains
  • This characteristic illustrates the fact that the use of a steel of the X2CrNiN23-4 type according to the invention makes it possible to maintain a good surface state over time for the reaction in question and therefore to limit at the maximum the shielding phenomenon.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP09759959A 2008-12-01 2009-11-27 Verfahren zur herstellung von adipinsäure Withdrawn EP2364286A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0806728A FR2939131B1 (fr) 2008-12-01 2008-12-01 Procede de fabrication d'acide adipique
PCT/EP2009/065995 WO2010063655A1 (fr) 2008-12-01 2009-11-27 Procede de fabrication d'acide adipique

Publications (1)

Publication Number Publication Date
EP2364286A1 true EP2364286A1 (de) 2011-09-14

Family

ID=40763864

Family Applications (1)

Application Number Title Priority Date Filing Date
EP09759959A Withdrawn EP2364286A1 (de) 2008-12-01 2009-11-27 Verfahren zur herstellung von adipinsäure

Country Status (10)

Country Link
US (1) US20110306789A1 (de)
EP (1) EP2364286A1 (de)
JP (1) JP2012510491A (de)
KR (1) KR20110091721A (de)
CN (1) CN102227398A (de)
BR (1) BRPI0916164A2 (de)
FR (1) FR2939131B1 (de)
RU (1) RU2011127011A (de)
SG (1) SG171448A1 (de)
WO (1) WO2010063655A1 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012121300A1 (ja) * 2011-03-09 2012-09-13 三菱化学株式会社 共役ジエンの製造方法
JP6297602B2 (ja) 2013-02-08 2018-03-20 コベストロ、ドイチュラント、アクチエンゲゼルシャフトＣｏｖｅｓｔｒｏ Ｄｅｕｔｓｃｈｌａｎｄ Ａｇ ホスゲン化のガス状粗生成物からの、気相中の第一級アミンをホスゲン化することにより調製されたイソシアネートの分離方法
WO2015074802A1 (en) * 2013-11-25 2015-05-28 Exxonmobil Chemical Patents Inc. Lean duplex stainless steel as construction material

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5446117A (en) * 1977-09-21 1979-04-11 Nippon Stainless Steel Co Twoophase stainless steel having good hot working property
JPS60262946A (ja) * 1984-06-11 1985-12-26 Kawasaki Steel Corp 熱間加工性に優れた二相ステンレス鋼
KR910002280B1 (ko) * 1987-11-17 1991-04-11 한국과학기술원 아디프산의 제조방법
US5472680A (en) * 1994-01-26 1995-12-05 E. I. Du Pont De Nemours And Company Production of NO from N2 O
TW460452B (en) * 1998-09-14 2001-10-21 Rhodia Fiber & Amp Resin Inter Process for the crystallization of carboxylic acid and process for manufacturing crystalline carboxylic acid
TWI238157B (en) * 2001-01-25 2005-08-21 Asahi Kasei Corp Process for producing alkanedicarboxylic acid
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
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
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。

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2010063655A1 *

Also Published As

Publication number Publication date
FR2939131A1 (fr) 2010-06-04
FR2939131B1 (fr) 2010-12-17
US20110306789A1 (en) 2011-12-15
KR20110091721A (ko) 2011-08-12
JP2012510491A (ja) 2012-05-10
CN102227398A (zh) 2011-10-26
RU2011127011A (ru) 2013-01-10
BRPI0916164A2 (pt) 2018-07-17
WO2010063655A1 (fr) 2010-06-10
SG171448A1 (en) 2011-07-28

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