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  • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
  • B01J23/80—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with zinc, cadmium or mercury
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  • B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
  • B01J23/889—Manganese, technetium or rhenium
  • B01J23/8896—Rhenium
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  • B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
  • B01J23/8933—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
  • B01J23/8953—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals also combined with metals, or metal oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with zinc, cadmium or mercury
• • 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
  • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
  • B01J27/24—Nitrogen compounds
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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  • B01J35/00—Catalysts, in general, characterised by their form or physical properties
  • B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
  • B01J35/61—Surface area
  • B01J35/615—100-500 m2/g
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  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
  • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
  • C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
  • C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
  • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
  • C07D295/023—Preparation; Separation; Stabilisation; Use of additives
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
  • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
  • C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
  • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
  • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
  • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
  • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
  • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
  • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
  • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
  • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Definitions

• the present invention relates to a catalyst for the synthesis of ethyleneamine and its use. More specifically, it relates to the conversion of ethanolamine (MEA) and ammonia to ethylenediamine (EDA), diethylenetriamine (DETA;), hydroxyethylethylenediamine (AEEA), piperazine under hydrogen conditions.
• MEA ethanolamine
• EDA ethylenediamine
• DETA diethylenetriamine
• AEEA hydroxyethylethylenediamine
• a catalyst for ethyleneamine such as PIP), hydroxyethylpiperazine (HEP) or aminoethylpiperazine (AEP), and a method for producing ethyleneamine.
• Ethyleneamine products are important chemical raw materials and fine chemical intermediates, which mainly include ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, polyethene polyamine, piperazine and other products.
• Epoxy resin curing agent, emulsifier, antifreeze, organic solvent and chemical analysis reagent used in the production of pesticides, fungicides, herbicides, fuels, pharmaceuticals, surfactants, metal complexing agents, etc.
• Additives also used in the production of chelating agents, corrosion inhibitors, soil improvers, lubricants, lubricant additives and rubber accelerators, as well as textiles, paper, coatings and adhesives.
• the industrial synthesis of ethyleneamine is mainly a dichloroethane process and an ethanolamine process.
• the ethanolamine process route has low investment and low environmental pollution.
• the ethanolamine process is further divided into a reduction process and a condensation process, wherein the reduction process needs to be carried out under high pressure hydrogen conditions, and the product is mostly ethylenediamine; and the condensation process does not require hydrogen, and the reaction product is mainly cyclic amine.
• the synthesis process of industrial ethyleneamine was developed earlier in foreign countries. Among them, BASF first developed the ethanolamine process, and realized industrialization in the 1960s. Later, it was adopted by many European and American companies.
• the ethanolamine process developed by BASF uses metal catalysts such as M, Co and Cu.
• the reaction temperature is 150 ⁇ 230°C and the pressure is 20.0 ⁇ 30.0MPa.
• the products are mainly ethylenediamine, diethylenetriamine and hydroxyethylethylene. Amine, piperazine, aminoethylpiperazine, hydroxyethylpiperazine, and the like.
• most of the current industrial ethyleneamine products rely on imports.
• Ethylamine and ammonia are aminated in the presence of a catalyst to form ethylenediamine. Since the intermediate imine has higher reactivity than ammonia, the reaction inevitably produces complex polyalkylene polyamine by-products, resulting in ethylenediamine. Yield Lowering and causing difficulty in product separation. Common methods can increase the selectivity of the product, but the conversion rate is reduced, which affects the production capacity of ethylenediamine. Therefore, there is a need for a catalyst that not only improves the selectivity of the target product, but also maintains a good amination conversion.
• US5068330 uses different nickel-based metal catalysts, adding noble metals such as Ir, Pt, Ru, etc.
• the conversion of ethanolamine is 20% ⁇ 45% at 120 ⁇ 300 °C, and the selectivity of ethylenediamine is 15% ⁇ 55%. And the selectivity of diethylenetriamine is 10% to 20%.
• the ethanolamine conversion rate and the ethylenediamine selectivity of the catalyst are difficult to meet the requirements, and the precious metal is repeatedly added continuously during the preparation process, which increases the complexity of the process operation and the production cost.
• U.S. Patent 4,642,303 discloses that under the action of a Ni-Cu-Cr catalyst, the amination temperature of the ethanolamine is advantageous for the formation of ethylenediamine at a low temperature.
• US 4,123,462 teaches that the activity of the catalyst is closely related to the support material, wherein changing the surface properties of the surface area, pore size, pore volume and shape of the support will affect the activity of the catalyst to a certain extent.
• the carrier material and the catalyst activity are closely related, and the carrier used for the catalyst is subjected to amination treatment, and the surface of the carrier is acidic due to the presence of a large amount of hydroxyl groups on the surface of the carrier SiO 2 or A1 2 0 3 .
• the present invention provides a catalyst for synthesizing ethyleneamine, the catalyst comprising three main components: a main active component, an auxiliary agent, and an ammoniated carrier, wherein the main active component Selecting one or more of the group consisting of M and Co selected from the group consisting of Fe, Cu, Ru, Re, K, Zn and PB, and One or more of their respective oxide composition groups; the ammoniated carrier is aminated by one or more carriers selected from the group consisting of SiO 2 and A1 2 0 3 It is obtained that the amination treatment comprises: contacting the carrier with an ammonia source at a temperature of 200 to 400 ° C for 0.5 to 24 hours.
• the support has a specific surface area of from 150 to 350 m 2 /g and an average pore diameter of from 8 to 80 nm.
• the ammonia source is selected from one or more of the group consisting of ammonia, liquid ammonia, ammonia, and urea.
• the primary active component comprises from 1 to 40%, preferably from 5 to 30%, based on the total weight of the catalyst.
• the adjuvant comprises from 0.1 to 20%, preferably from 0.1 to 15%, based on the total weight of the catalyst.
• the present invention provides a process for the preparation of ethyleneamine from ethanolamine and ammonia, the process comprising: converting ethanolamine and ammonia to ethylene under hydrogen conditions in the presence of a catalyst as described above amine.
• the method is carried out at a temperature of 135 to 200 ° C, a pressure of 6.0 to 22.0 MPa, and a liquid space velocity of ethanolamine of OJ l ⁇ h- 1 .
• the catalyst is reductively activated under a hydrogen atmosphere and at a pressure of atmospheric pressure at a temperature of 150 to 400 ° C and a hydrogen space velocity of 500 to 4000 h" 1 prior to use.
• the present invention provides a supported catalyst for synthesizing an ethyleneamine product, which is composed of a main active component, an auxiliary agent and an ammoniated carrier, and the main active component is Ni and/or Co.
• the auxiliary agent is one or more of the group consisting of Fe, Cu, Ru, Re, K, Zn and B and their respective oxides;
• the carrier is selected from Si0 2 and/or A1 2 0 3 , and the carrier has passed Special treatment for ammoniation.
• the catalyst is prepared by an impregnation method in which the support is impregnated with a solution of a soluble salt of M and/or Co, which is a nitrate, a chloride, an acetate, an oxalate or a sulfuric acid of M and/or Co. Salt, citrate or other soluble salt.
• the main active component accounts for 1 ⁇ 40% of the total weight of the catalyst; the auxiliary agent accounts for 0.1-20% of the total weight of the catalyst; the carrier Si0 2 or A1 2 0 3 has a specific surface area of 150-350 m 2 /g, and the average pore diameter is 8-80 nm.
• the carrier Si0 2 and/or A1 2 0 3 are subjected to ammoniation treatment using ammonia gas, liquid ammonia, ammonia water or urea.
• the catalyst of the invention is reductively activated in a hydrogen atmosphere before application: the pressure is normal pressure, the temperature is 150-400 ° C, the space velocity of hydrogen is SOO ⁇ OO h ⁇ , and the conversion of ethanolamine and ammonia to ethyleneamine under hydrogen conditions
• Product Reaction conditions temperature is 135 ⁇ 200 °C, pressure is 6.0 ⁇ 22.0MPa, liquid air velocity of ethanolamine is
• the reactor of the present invention may employ a fixed bed reactor, a slurry bed reactor or a trickle bed reactor. Among them, a trickle bed reactor is preferred.
• the liquid ethanolamine and ammonia mixture can be directly pumped into the preheater and mixed with hydrogen, and then preheated to 135 to 200 ° C and then introduced into the trickle bed reactor.
• the catalyst is applied to the reaction of ethanolamine and ammonia under hydrogen conditions, and exhibits excellent activity, selectivity and stability.
• the ethyleneamine product formed includes ethylenediamine, diethylenetriamine and hydroxyethylethylenediamine.
• Ethyleneamine such as piperazine, aminoethylpiperazine or hydroxyethylpiperazine.
• the hydrogen-producing condition means that hydrogen is present.
• the present invention has a remarkable effect that the carrier of the catalyst of the present invention, SiO 2 or A1 2 0 3 , is subjected to ammoniation treatment using ammonia gas, liquid ammonia, ammonia water or urea. Due to the presence of a large amount of hydroxyl groups on the surface of the carrier SiO 2 or A1 2 0 3 to make the surface of the carrier acidic, it is advantageous to polymerize the intermediate product imine to produce a large amount of by-products, thereby reducing the selectivity of ethylenediamine.
• the treated carrier After the surface of the carrier is ammoniated, a large amount of hydroxyl groups on the surface are converted into an amine group to be alkaline, which lowers the possibility of polymerization of the imine and improves selectivity and stability.
• the treated carrier After the treated carrier is loaded with the main active component and the auxiliary agent, it is applied to the reaction of ethanolamine and ammonia under the hydrogen condition, and exhibits excellent activity, selectivity and stability, optimizes the reaction conditions, and realizes the B.
• the flexible modulation of the amine products provides the possibility for industrial production to adapt to market fluctuations.
• the temperature and pressure of the reaction process conditions are significantly lower than those of the prior art. Optimization of production process conditions will reduce the pressure requirements on the reaction equipment, reduce the one-time investment and production costs of the reaction unit, and reduce the difficulty of operation.
• Example 1 The method of the present invention will be further described below in conjunction with the examples, which are not intended to limit the invention. Parts, percentages and amounts in this application are by weight unless otherwise indicated. Example 1
• the ammoniated SiO 2 carrier was impregnated with half of the aqueous solution and allowed to dry naturally, followed by It was dried at 120 ° C for 4 hours and then calcined at 500 ° C for 4 hours. Then, the ammoxidation-treated SiO 2 carrier was impregnated a second time with the remaining remaining half of the aqueous solution, followed by natural drying, drying at 120 ° C for 4 hours, and calcination at 500 ° C for 4 hours.
• the catalyst was reduced in a hydrogen stream at 375 ° C (atmospheric pressure, ZOOOh- 1 ) for 4 hours before use. When the temperature inside the reactor naturally drops to 160 °C, the pressure is increased to 8 MPa.
• the metal-loaded A1 2 0 3 carrier was secondarily impregnated with the remaining remaining half of the aqueous solution, followed by drying naturally, and drying at 120 ° C. The hour was calcined at 500 ° C for 4 hours. See Table 1 for the catalyst evaluation scheme and Table 1 for the reaction results.
• Conv. (%) (l- NEDA XCEDA / (N E DA > ⁇ C EDA + ⁇ NixCi)) x 100%
• NEDA the number of moles of ethanolamine in the product
• Ni the number of moles of product i in the product
• Ci The number of carbon atoms of the product i in the product.
• the catalyst components of Example 2 and Comparative Example 1 were the same, except that the carrier of Example 2 was subjected to ammoniation treatment, and the carrier of Comparative Example 1 was not subjected to ammoniation treatment.
• the conversion of ethanolamine was improved. 31%, the selectivity of ethylenediamine increased by 32%.
• Example 14 and Comparative Example 2 were the same, except that the carrier of Example 14 was subjected to ammoniation treatment, and the carrier of Comparative Example 2 was not subjected to ammoniation treatment. As a result of comparison, it was found that the conversion of ethanolamine was improved. 34%, the selectivity of ethylenediamine increased by 27%.
• the agent and the method for preparing ethyleneamine realize one or more of the following: (1) being realized at a lower reaction pressure, and (2) modulating the reaction condition to flexibly modulate the composition of the ethyleneamine, 3) Reduce the one-time investment and production costs of the production equipment, (4) to achieve easy operation, (5) to improve the activity of the catalyst, (6) to improve the selectivity of the product, (7) to provide conversion rate of raw materials, and (8) Improve the stability of the method.

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