EP2364286A1 - Method for the production of adipic acid - Google Patents

Method for the production of adipic acid

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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Withdrawn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
German (de)
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
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Filing date
Publication date
Application filed by Rhodia Operations SAS filed Critical Rhodia Operations SAS
Publication of EP2364286A1 publication Critical patent/EP2364286A1/en
Withdrawn legal-status Critical Current

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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.

Abstract

The invention relates to a method for the production of adipic acid, carried out in devices made from a material resistant to corrosion from the synthesis medium. More specifically, the invention relates to a method for the production of adipic acid, carried out in devices, some of which are made from a material resistant to nitric corrosion. The corrosion-resistant material is a duplex ferritic-austenitic stainless steel of type X2 CrNiN23-4 (1.4362) according to European nomenclature.

Description

Procédé de fabrication d'acide adipique Process for producing adipic acid
La présente invention concerne un procédé de fabrication d'acide adipique mis en œuvre dans des dispositifs réalisés en matériau résistant à la corrosion du milieu de synthèse.The present invention relates to a method of manufacturing adipic acid used in devices made of material resistant to corrosion of the synthesis medium.
L'acide adipique est un composé chimique important utilisé comme matière première dans la fabrication de nombreux produits et dans de nombreuses applications. Ainsi, l'acide adipique est utilisé comme composé intermédiaire pour la synthèse de composés macromoléculaires tels que les polyamides, plus particulièrement le PA6-6, les polyesters, polyuréthannes, par exemple. Cet article est également utilisé pour la fabrication de plastifiant ou comme additifs.Adipic acid is an important chemical compound used as a raw material for many products and applications. Thus, 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.
Plusieurs procédés de fabrication de l'acide adipique sont connus et exploités industriellement. Actuellement, le procédé principal exploité industriellement consiste à oxyder par l'oxygène le cyclohexane pour obtenir des composés intermédiaires cyclohexanol et cyclohexanone, généralement un mélange de ces deux composés. Dans une étape ultérieure, les composés intermédiaires, cyclohexanol/cyclohexanone, sont oxydés en acide adipique par de l'acide nitrique, en présence d'un catalyseurSeveral processes for the manufacture of adipic acid are known and exploited industrially. Currently, the main method used industrially is to oxidize cyclohexane with oxygen to obtain cyclohexanol and cyclohexanone intermediates, generally a mixture of these two compounds. In a subsequent step, the intermediate compounds, cyclohexanol / cyclohexanone, are oxidized to adipic acid with nitric acid in the presence of a catalyst.
L'acide adipique est récupéré et purifié par les techniques habituelles et préférentiellement, par cristallisation.The adipic acid is recovered and purified by the usual techniques and preferably by crystallization.
La réaction d'oxydation nitrique des composés intermédiaires est mise en œuvre dans des dispositifs et réacteurs devant résister à la corrosion nitrique. Généralement, ces dispositifs et réacteurs sont construits en aciers spéciaux commercialisés pour leur résistance à la corrosion nitrique.The nitric oxidation reaction of the intermediate compounds is carried out in devices and reactors to resist nitric corrosion. Generally, these devices and reactors are constructed of special steels marketed for their resistance to nitric corrosion.
Toutefois, il est observé dans les conditions de température et selon la nature des composés présents dans le milieu d'oxydation du procédé de fabrication de l'acide adipique, un phénomène non négligeable de corrosion de ces aciers spéciaux. Ce phénomène de corrosion présente des inconvénients pour la fiabilité du matériel mais surtout introduit des impuretés métalliques dans l'acide adipique produit. De ce fait, le procédé de purification de l'acide adipique doit être adapté pour éliminer ces impuretés.However, it is observed under the conditions of temperature and according to the nature of the compounds present in the oxidation medium of the adipic acid manufacturing process, a significant phenomenon of corrosion of these special steels. This corrosion phenomenon has disadvantages for the reliability of the material but especially introduces metal impurities into the adipic acid product. As a result, the process for purifying adipic acid must be adapted to remove these impurities.
Par ailleurs, après l'étape d'oxydation par l'acide nitrique de composés cyclohexanol/cyclohexanone, l'acide adipique est purifié notamment lors d'une étape de cristallisation afin d'obtenir des cristaux d'acide adipique. La cristallisation de l'acide adipique est réalisée à partir des solutions obtenues lors de l'oxydation nitrique des mélanges cyclohexanone/cyclohexanol. Ces solutions sont acides et contiennent une quantité importante d'acide nitrique et/ou d'ions nitrates.Furthermore, after the step of nitric acid oxidation of cyclohexanol / cyclohexanone compounds, 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.
Il a été observé avec les matériels en aciers inoxydables de l'art antérieur, des phénomènes d'encrassement des dispositifs de cristallisation par dépôt d'acide adipique cristallisé sur les parois de l'appareillage. Ce phénomène appelé « blindage » dépend de la nature du matériau et de l'état de surface des parois.It has been observed with stainless steel materials of the prior art, fouling phenomena crystallization devices by deposition of crystallized adipic acid on the walls of the apparatus. This phenomenon called "shielding" depends on the nature of the material and the surface condition of the walls.
Ce blindage nécessite l'arrêt périodique du procédé pour éliminer les dépôts d'acide adipique sur les parois d'échange de chaleur ou les parois du cristallisoir.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.
L'état de surface se mesure notamment par la rugosité de surface du matériau par exemple selon la méthode définie par les normes NF EN ISO 3274 et NF EN ISO 4288. Plus la valeur de la rugosité est importante et plus le phénomène de blindage est favorisé.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. The higher the value of the roughness, the more the shielding phenomenon is favored. .
Un des buts de la présente invention est de remédier à ces inconvénients en proposant de réaliser l'étape de fabrication de l'acide adipique, à savoir l'oxydation nitrique des composés cyclohexanone et cyclohexanol dans des dispositifs et réacteurs construits en un matériau limitant le phénomène de corrosion et donc diminuant la présence d'impuretés dans l'acide adipique produit. Un autre but est de limiter le phénomène de blindage des parois des dispositifs de cristallisation par l'acide adipique.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.
A cet effet, l'invention propose un procédé de fabrication d'acide adipique comprenant une étape d'oxydation par l'acide nitrique de composés cyclohexanol/cyclohexanone mise en œuvre dans une installation comprenant au moins un réacteur et des dispositifs ou appareils, caractérisé en ce qu'au moins les parties du réacteur en contact avec le milieu réactionnel d'oxydation nitrique et, éventuellement, des parties des dispositifs et/ou appareils sont réalisés avec un matériau acier inoxydable austéno-ferritique dit duplex de type X2 CrNiN23-4 (1.4362) selon la nomenclature européenne. Ces aciers peuvent être commercialisés sous les désignations commerciales URANUS 35N ou SAF 2304.For this purpose, 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.
Par l'expression « au moins les parois en contact avec les milieux réactionnels », il faut comprendre que les dispositifs ou réacteurs peuvent être réalisés totalement avec de l'acier inoxydable austéno-ferritique dit duplex de type X2 CrNiN23-4 ou seulement partiellement avec ce matériau. Dans ce dernier cas, les parties réalisées en acier inoxydable austéno-ferritique dit duplex de type X2 CrNiN23-4 sont celles entrant en contact avec le milieu réactionnel ou les vapeurs et gaz provenant de ce milieu réactionnel.By the expression "at least the walls in contact with the reaction media", it should be understood that 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. In the latter case, 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.
Ainsi, il a été constaté que le phénomène de corrosion des parois ou parties réalisées en acier inoxydable austéno-ferritique dit duplex type X2 CrNiN23-4 est absent ou très limité par rapport au phénomène observé avec d'autres aciers inoxydables commercialisés comme résistants à la corrosion nitrique, comme par exemple l'acier inoxydable austénitique de type AISI 304L.Thus, it has been found that the phenomenon of corrosion of the walls or parts made of austeno-ferritic stainless steel said duplex type X2 CrNiN23-4 is absent or very limited compared to the phenomenon observed with other stainless steels marketed as resistant to corrosion. nitric corrosion, such as Ausi 304L austenitic stainless steel.
L'acier inoxydable austéno-ferritique dit duplex de type X2 CrNiN23-4 est un matériau dont la composition est définie dans les normes NF EN 10088-1 (anciennement NFA35- 574) et NF EN 10028-7 applicables dans leur dernière révision.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.
Le milieu d'oxydation nitrique du cyclohexanol et/ou cyclohexanone comprend des composés métalliques.The nitric oxidation medium of cyclohexanol and / or cyclohexanone comprises metal compounds.
Le milieu d'oxydation nitrique du cyclohexanol et/ou cyclohexanone comprend de l'acide nitrique à une concentration comprise avantageusement entre 20 et 35% en poids, des composés métalliques formant le catalyseur d'oxydation nitrique ainsi que des composés métalliques présents dans le cyclohexanol et/ou cyclohexanone et correspondant aux catalyseurs utilisés dans l'oxydation du cyclohexane par l'oxygène ou la décomposition du peroxyde d'hydroxycyclohexyle. La réaction d'oxydation nitrique est mise en œuvre à une température comprise entre 70 et 1200C, et avantageusement entre 70 et 1000C, généralement sous une pression absolue comprise entre 1 bar et 5 bars.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.
Selon l'invention, les réacteurs utilisés pour la réalisation de l'oxydation nitrique sont construits en acier inoxydable austéno-ferritique dit duplex de type X2 CrNiN23-4. Il est également avantageux de réaliser les autres appareils et dispositifs de l'installation avec ce matériau acier inoxydable austéno-ferritique dit duplex de type X2 CrNiN23-4.According to the invention, 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.
De façon avantageuse, le procédé de l'invention comprend une étape de cristallisation de l'acide adipique, les dispositifs ou appareils comprennent une cuve de cristallisation équipée avec des moyens d'agitation, des moyens de refroidissement et/ou concentration de la solution d'acide adipique et au moins une partie des parois de la cuve de cristallisation et/ou des moyens de refroidissement et/ou concentration en contact avec la solution d'acide adipique est réalisée en matériau acier inoxydable austéno-ferritique dit duplex de type X2CrNiN23-4 (1.4362) selon la nomenclature européenne.Advantageously, 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.
On peut aussi citer, à titre d'exemple, comme autres dispositifs et appareils réalisés avantageusement en acier inoxydable austéno-ferritique dit duplex de type X2CrNiN23-4, tout ou parties des réacteurs, des finisseurs, des colonnes de concentration nitrique, ou analogue. Cette liste n'a pas de caractère limitatif et est donnée uniquement à titre indicatif. En effet, tous les dispositifs de l'installation de fabrication de l'acide adipique en contact avec un milieu contenant de l'acide nitrique peuvent être réalisés en acier inoxydable austéno-ferritique dit duplex de type X2CrNiN23-4.By way of example, other devices and devices advantageously made of stainless steel austenitic-ferritic said duplex type X2CrNiN23-4, all or part of the reactors, pavers, nitric concentration columns, or the like. This list is not exhaustive and is given for information only. Indeed, all devices of the adipic acid manufacturing facility in contact with a medium containing nitric acid can be made of austenitic ferritic stainless steel said duplex type X2CrNiN23-4.
L'invention sera mieux illustrée au vu des exemples donnés ci-dessous uniquement à titre indicatif.The invention will be better illustrated in view of the examples given below for information only.
Les essais de corrosions donnés ci-dessous uniquement à titre d'illustration montrent clairement les avantages apportés par l'utilisation de l'acier inoxydable austéno-ferritique dit duplex de type X2CrNiN23-4 dans le procédé de fabrication de l'acide adipique par oxydation nitrique de cyclohexanol et/ou cyclohexanone. Des essais pour déterminer la tenue à la corrosion et d'évolution de l'état de surface d'articles réalisés en différentes nuances d'aciers inoxydables ont été réalisés selon le mode opératoire ci-dessous :The corrosion tests given below purely by way of illustration clearly show the advantages brought about by the use of duplex-type austenitic-ferritic stainless steel of type X2CrNiN23-4 in the process for the manufacture of adipic acid by oxidation. nitric acid of cyclohexanol and / or cyclohexanone. Tests to determine the resistance to corrosion and evolution of the surface condition of articles made in different grades of stainless steels were made according to the procedure below:
Des éprouvettes de forme parallélipédique de dimensions 50x30 mm dont la surface a été polie pour avoir une rugosité initiale Ra inférieure à 0,1 μm ont été immergées dans un milieu issu de l'oxydation nitrique d'un mélange cyclohexanone/cyclohexanol comprenant une concentration pondérale en acide adipique de 24% et une teneur en acide nitrique de l'ordre de 28%.Specimens of parallelepiped shape of dimensions 50 × 30 mm, the surface of which was polished to have an initial roughness Ra of less than 0.1 μm, were immersed in a medium resulting from the nitric oxidation of a cyclohexanone / cyclohexanol mixture comprising a weight concentration. adipic acid of 24% and a nitric acid content of the order of 28%.
La solution est maintenue à une température de 900C sous pression atmosphérique et est mise sous agitation pendant toute la durée d'immersion. Après 400 heures d'immersion, l'état de surface des éprouvettes et la perte d'épaisseur sont déterminées. Ces éprouvettes sont de nouveau immergées pour une nouvelle durée de 400 heures dans le même milieu. Toutefois, la solution est renouvelée avant chaque nouvelle immersion.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.
Les éprouvettes testées ont été réalisées en deux nuances d'acier inoxydable :The test pieces tested were made in two grades of stainless steel:
Eprouvette 1 : acier de type AISI 304LSpecimen 1: steel type AISI 304L
Eprouvette 2 : acier de type X2CrNiN23-4 (équivalent Uranus 35N ou SAF2304) La composition de ces nuances d'acier est donnée dans le tableau I ci-dessous :Specimen 2: Steel Type X2CrNiN23-4 (Uranus 35N equivalent or SAF2304) The composition of these steel grades is given in Table I below:
(bal. Signifie complément à 100%) Les résultats observés sont rassemblés dans le tableau II ci-dessous : (bal. Means 100% complement) The observed results are summarized in Table II below:
II ressort des résultats ci-dessus que l'éprouvette 2, qui correspond à l'invention, présente une rugosité qui varie très peu au cours du temps par rapport à celle mesurée pour un acier de type AISI 304L (eprouvette 1 ) et qui reste toujours inférieure à l'éprouvette 1. Cette caractéristique illustre le fait que l'utilisation d'un acier du type X2CrNiN23-4 selon l'invention permet de conserver un bon état de surface au cours du temps pour la réaction concernée et donc de limiter au maximum le phénomène de blindage. Par ailleurs, les résultats ci-dessus montrent que la résistance à la corrosion (perte d'épaisseur) pour un acier du type X2CrNiN23-4 dans le milieu issu de l'oxydation nitrique d'un mélange cyclohexanone/ cyclohexanol (selon l'invention) est accrue. It follows from the above results that the 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. Moreover, the results above show that the corrosion resistance (loss of thickness) for a steel of the X2CrNiN23-4 type in the medium resulting from the nitric oxidation of a cyclohexanone / cyclohexanol mixture (according to the invention ) is increased.

Claims

Revendications claims
1. Procédé de fabrication d'acide adipique par oxydation nitrique de cyclohexanol et/ou cyclohexanone le procédé étant mis en œuvre dans une installation comprenant au moins un réacteur et des dispositifs ou appareils, caractérisé en ce qu'au moins les parties du réacteur en contact avec le milieu réactionnel d'oxydation nitrique et, éventuellement, des parties des dispositifs et/ou appareils sont réalisés avec un matériau acier inoxydable austéno-ferritique dit duplex de type X2CrNiN23-4 (1.4362) selon la nomenclature européenne.Process for the manufacture of adipic acid by nitric oxidation of cyclohexanol and / or cyclohexanone, the process being carried out 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 devices are made of a so-called duplex austenitic-ferritic stainless steel material of the type X2CrNiN23-4 (1.4362) according to the European nomenclature.
2. Procédé selon la revendication 1 caractérisé en ce que le ou les réacteurs sont réalisés en acier inoxydable austéno-ferritique dit duplex de type X2CrNiN23-4 (1.4362).2. Method according to claim 1 characterized in that the reactor or reactors are made of austeno-ferritic stainless steel said duplex type X2CrNiN23-4 (1.4362).
3. Procédé selon les revendications 1 ou 2, caractérisé en ce que le milieu réactionnel d'oxydation nitrique comprend des composés métalliques.3. Method according to claims 1 or 2, characterized in that the nitric oxidation reaction medium comprises metal compounds.
4. Procédé selon l'une des revendications précédentes, caractérisé en ce que la réaction d'oxydation nitrique est réalisée à une température comprise entre 700C et 1200C.4. Method according to one of the preceding claims, characterized in that the nitric oxidation reaction is carried out at a temperature between 70 0 C and 120 0 C.
5. Procédé selon l'une des revendications précédentes, caractérisé en ce que les dispositifs de l'installation en contact avec le milieu réactionnel d'oxydation nitrique sont réalisés en acier inoxydable austéno-ferritique dit duplex de type X2CrNiN23-4 (1.4362).5. Method according to one of the preceding claims, characterized in that the devices of the installation in contact with the nitric oxidation reaction medium are made of stainless steel austenitic ferritic so-called duplex type X2CrNiN23-4 (1.4362).
6. Procédé selon l'une des revendications précédentes, caractérisé en ce que le procédé comprend une étape de cristallisation de l'acide adipique, en ce que les dispositifs ou appareils comprennent une cuve de cristallisation équipée avec des moyens d'agitation, des moyens de refroidissement et/ou concentration de la solution d'acide adipique et en ce qu'au moins une partie des parois de la cuve de cristallisation et/ou des moyens de refroidissement et/ou concentration en contact avec la solution d'acide adipique est réalisée en matériau acier inoxydable austéno-ferritique dit duplex de type X2CrNiN23-4 (1.4362) selon la nomenclature européenne. 6. Method according to one of the preceding claims, characterized in that the method comprises a step of crystallization of adipic acid, in that the devices or apparatus comprises a crystallization vessel equipped with stirring means, means cooling and / or concentration of the adipic acid solution and in that at least a portion of the walls of the crystallization vessel and / or cooling means and / or concentration in contact with the adipic acid solution is made of austenitic-ferritic stainless steel said duplex type X2CrNiN23-4 (1.4362) according to the European nomenclature.
EP09759959A 2008-12-01 2009-11-27 Method for the production of adipic acid Withdrawn EP2364286A1 (en)

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