WO2020028262A1 - Procédés et catalyseurs pour la production de diéthanolamine à partir de glycolaldéhyde - Google Patents

Procédés et catalyseurs pour la production de diéthanolamine à partir de glycolaldéhyde Download PDF

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Publication number
WO2020028262A1
WO2020028262A1 PCT/US2019/043942 US2019043942W WO2020028262A1 WO 2020028262 A1 WO2020028262 A1 WO 2020028262A1 US 2019043942 W US2019043942 W US 2019043942W WO 2020028262 A1 WO2020028262 A1 WO 2020028262A1
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Prior art keywords
diethanolamine
glycolaldehyde
hydrogenation catalyst
noble metal
solid support
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PCT/US2019/043942
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English (en)
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James Brazdil
Chi Cheng Ma
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Archer Daniels Midland Company
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Publication of WO2020028262A1 publication Critical patent/WO2020028262A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Definitions

  • the present invention from one perspective relates to methods for the synthesis of biobased amines, and more particularly, to methods for the synthesis of such amines which are presently also made from non-renewable resources. From another perspective, the present invention relates to methods for the production of diethanolamine.
  • Biomass material derived from living or recently living organisms
  • Biomass is viewed as a readily available, inexpensive supply of renewable, non-petroleum based carbon from which many such known, high value chemicals can be derived.
  • the ability to convert biomass to fuels, chemicals, energy and other materials is expected to strengthen rural economies, decrease dependence on oil and gas resources, and reduce air and water pollution.
  • the generation of energy and chemicals from renewable resources such as biomass also reduces the net liberation of carbon dioxide, a greenhouse gas, into the environment, from fossil-based sources of otherwise“sequestered” carbon.
  • amines represent a class of known, useful chemical products from petroleum- based carbon-for example, as key monomers for the synthesis of polyamides, polyureas and polyepoxides, which are all of growing interest in automotive, aerospace, building and health applications-which present still an additional challenge in that very few natural amines are available from which biobased replacements might be obtained.
  • the ethanolamines - that is, monoethanolamine or 2-aminoethanol (MEA), diethanolamine (DEA) and triethanolamine (TEA) - are specific examples of known, commercially significant amines from petroleum-based carbon, specifically, through reacting ethylene oxide with aqueous ammonia to provide MEA, DEA, and TEA in admixture with one another.
  • the product distribution can be altered to an extent by various means, in particular, by changing the stoichiometry of the reactants. Nevertheless one seeking to make DEA, for example, for use as an acid gas removal agent (e.g.
  • Ethylene oxide as a starting material is also undesirable, posing significant toxicological, reactive safety and environmental concerns.
  • Glycolaldehyde (C2H4O2) is an example of just such an intermediate, having significant utility as a reactive intermediate in that it is the smallest molecule having both reactive aldehyde and hydroxyl groups, and being susceptible of production by several conversion pathways from biomass-derived carbohydrates, such as fructose or sucrose.
  • aspects of the invention are associated with the discovery of improvements in catalyst formulations for the conversion of glycolaldehyde to diethanolamine, which catalyst systems exhibit improved selectivity to this desired product and consequently reduced selectivity to monoethanol amine and byproducts such as ethylene glycol. More particular aspects relate to the beneficial effects of noble metal-containing hydrogenation catalysts in performing reductive ami nation of glycolaldehyde, to selectively produce diethanolamine ⁇
  • Such catalysts may be included in the reaction mixture, to which glycolaldehyde and an aminating agent are added, and from which diethanolamine is produced.
  • Suitable hydrogenation catalysts may be heterogeneous in the reaction mixture, and suitably present as a solid in a liquid and/or gaseous reaction mixture under reductive ami nation conditions.
  • a heterogeneous hydrogenation catalyst allows for ease of separation of the product mixture, following reaction, from this catalyst. In the case of batchwise operation, this allows for simple filtration of the catalyst from the product mixture.
  • a solid catalyst formulation also allows for catalyst particles to be made large enough, such that they may be contained in a reactor (e.g., fixed-bed reactor) with sufficiently low pressure drop as needed for the process to be performed continuously, and therefore in a manner that is more amenable to commercial operation. Continuous operation may involve continuous feeding of the reactant glycolaldehyde, for example with an aminating agent such as ammonia or aqueous ammonia (ammonium hydroxide), and also with hydrogen.
  • an aminating agent such as ammonia or aqueous ammonia (ammonium hydroxide)
  • These streams may be contacted with the noble metal-containing hydrogenation catalyst, contained in the reactor and operating under reductive ami nation conditions. Such operation may also involve the continuous withdrawal of a product mixture comprising diethanolamine, followed by the separation of a diethanolamine-containing product from this mixture. More particularly, the diethanolamine-containing product may be separated from unconverted reactants and/or byproducts. At least a portion of any unconverted reactants (e.g. , hydrogen) may be recycled to the reactor (e.g., using a recycle compressor to return hydrogen, in a recycle gas stream, back to the reactor).
  • a solid catalyst also allows for the formulation to include other active constituents, such as one or more promoter metals.
  • Embodiments of the invention are directed to methods or processes for producing or synthesizing diethanolamine from glycolaldehyde.
  • the desired reductive amination reaction pathway can be depicted as:
  • glycolaldehyde is meant to encompass the compound shown above, as well as various forms that this reactive compound may undertake, such as in an aqueous environment of a reaction mixture as described herein.
  • Such forms include glycolaldehyde dimer and oligomer forms, as well as hydrated forms.
  • Glycolaldehyde dimer is a particularly prevalent form, and this form is also known as the ringed structure, 2, 5-dihydroxy- l,4-dioxane.
  • each mole of glycolaldehyde dimer is considered equivalent to two moles of glycolaldehyde. Similar considerations apply to other glycolaldehyde oligomers.
  • Molar selectivity to diethanolamine is the percentage, on a molar basis, of converted glycolaldehyde, which results in the formation of diethanolamine.
  • the yield of diethanolamine is the amount obtained, expressed as a percentage of the theoretical amount that would be obtained by reacting glycolaldehyde with 100% conversion and 100% molar selectivity to diethanolamine. The yield can be determined as the product of conversion and selectivity.
  • Particular embodiments are directed to methods for producing diethanolamine, comprising reacting glycolaldehyde (including forms of this compound as described above) with an aminating agent in the presence of a noble metal-containing hydrogenation catalyst under reductive ami nation conditions, to produce the diethanolamine (e.g. , in a product mixture from which the diethanolamine may be recovered, such as in a purified form following one or more separation steps).
  • a representative hydrogenation catalyst is a noble metal-containing catalyst, meaning that it comprises at least one noble metal.
  • the hydrogenation catalyst may comprise platinum or palladium as a noble metal or may comprise both of these noble metals.
  • the hydrogenation catalyst may comprise either or both of these noble metals, or other noble metals, in an amount, or in a combined amount, generally from 0.1 wt-% to 15 wt-%, and typically from 0.5 wt-% to 10 wt-%, based on the weight of the catalyst.
  • the hydrogenation catalyst may be a solid supported noble metal-containing catalyst, meaning that the noble metals are disposed on a solid support, which may be substantially refractory (inert) under reductive ami nation conditions, or which may itself be functional (e.g., in the case of providing acidic or basic sites to provide or promote catalytic activity).
  • a solid support which may be substantially refractory (inert) under reductive ami nation conditions, or which may itself be functional (e.g., in the case of providing acidic or basic sites to provide or promote catalytic activity).
  • Carbon, including activated carbon is an exemplary solid support.
  • the at least one noble metal of the hydrogenation catalyst may be selected from the group consisting of platinum (Pt), rhodium (Rh), ruthenium (Ru), palladium (Pd), silver (Ag), osmium (Os), iridium (Ir), and gold (Au), with the term“consisting of’ being used merely to denote group members, according to a specific embodiment, from which the noble metal(s) are selected, but not to preclude the addition of other noble metals and/or other metals generally.
  • a hydrogenation catalyst comprising a noble metal embraces a catalyst comprising at least two noble metals, as well as a catalyst comprising at least three noble metals, and likewise a catalyst comprising two noble metals and a third, non-noble metal such as a promoter metal (e.g., a transition metal).
  • a promoter metal e.g., a transition metal
  • the noble metal(s) is/are present in an amount, or combined amounts, within the ranges given above.
  • a representative hydrogenation catalyst may comprise the two noble metals Pt and Pd, and the Pt and Pd may independently be present in an amount within any of these ranges (e.g., from 1 wt-% to 7.5 wt-%). That is, either the Pt may be present in such an amount, the Pd may be present in such an amount, or both Pt and Pd may be present in such amounts.
  • a single noble metal e.g. , either Pt or Pd
  • two noble metals e.g., both Pt and Pd
  • a single noble metal, or two noble metals are substantially the only metals present in the hydrogenation catalyst, with the exception of metals that may be present in the solid support (e.g., such as aluminum being present in the solid support as aluminum oxide).
  • the single noble metal, or two noble metals may be substantially the only metals present.
  • any other metal(s), besides the single noble metal, or two noble metals, and metals of the solid support (if any), may be present in an amount or a combined amount of less than 0.1 wt-%, or less than 0.05 wt-%, based on the weight of the hydrogenation catalyst.
  • Any metals present in the catalyst, including noble metal(s) may have a metal particle size in the range generally from 0.3 nanometers (nm) to 20 nm, typically from 0.5 nm to 10 nm, and often from 1 nm to 5 nm.
  • representative hydrogenation catalysts may be disposed or deposited on a solid support, which is intended to encompass catalysts in which the noble metal(s) is/are on the support surface and/or within a porous internal structure of the support. Therefore, in addition to such hydrogenation- active metal(s), representative hydrogenation catalysts may further comprise a solid support, with exemplary solid supports comprising carbon and/or one or more metal oxides. Exemplary metal oxides are selected from the group consisting of aluminum oxide, silicon oxide, titanium oxide, zirconium oxide, magnesium oxide, strontium oxide, tin oxide, etc.
  • the solid support may comprise all, or substantially all of the one or more of such metal oxides, for example such that the one or more metal oxides are present in an amount, or combined amount, of at least 95% by weight of the solid support.
  • carbon such as activated carbon, may be present in an amount of at least 95% by weight, or at least 99% by weight, of the solid support.
  • Activated carbon refers to forms of carbon following any of a number of possible treatments (e.g. , high temperature steaming) to increase porosity.
  • Activated carbon also refers to forms obtained by chemical treatment (e.g. , an acid or a base) to alter properties such as the concentration of acid sites.
  • the noble metal(s) may be incorporated in the solid support according to known techniques for catalyst preparation, including sublimation, impregnation, or dry mixing.
  • an impregnation solution of a soluble compound of one or more of the noble metals in a polar (aqueous) or non-polar (e.g., organic) solvent may be contacted with the solid support, preferably under an inert atmosphere.
  • this contacting may be carried out, preferably with stirring, in a surrounding atmosphere of nitrogen, argon, and/or helium, or otherwise in a non-inert atmosphere, such as air.
  • the solvent may then be evaporated from the solid support, for example using heating, flowing gas, and/or vacuum conditions, leaving the dried, noble metal-impregnated support.
  • the noble metal(s) may be impregnated in the solid support, such as in the case of two noble metals being impregnated simultaneously with both being dissolved in the same impregnation solution, or otherwise being impregnated separately using different impregnation solutions and contacting steps.
  • the noble metal- impregnated support may be subjected to further preparation steps, such as washing with the solvent to remove excess noble metal(s) and impurities, further drying, calcination, etc. to provide the hydrogenation catalyst.
  • the solid support itself may be prepared according to known methods, such as extrusion to form cylindrical particles (extrudates) or oil dropping or spray drying to form spherical particles.
  • the amounts of noble metal(s) being present in the hydrogenation catalyst refer to the weight of such noble metal(s), on average, in a given catalyst particle (e.g., of any shape such as cylindrical or spherical), independent of the particular distribution of the noble metals within the particle.
  • different preparation methods can provide different distributions, such as deposition of the noble metal(s) primarily on or near the surface of the solid support or uniform distribution of the noble metal(s) throughout the solid support.
  • weight percentages described herein being based on the weight of the solid support or otherwise based on the weight of hydrogenation catalyst, can refer to weight percentages in a single catalyst particle but more typically refer to average weight percentages over a large number of catalyst particles, such as the number in a reductive animation reactor that form a catalyst bed as used in processes described herein.
  • aspects of the present invention relate to improvements in methods for the reductive amination of glycolaldehyde, resulting from the use of the noble metal- containing hydrogenation catalyst.
  • Particular improvements are increased selectivity to the desired compound, diethanolamine, and/or decreased selectivity to monoethanolamine and/or the hydrogenated byproduct, ethylene glycol, which may be less desired for a given, overall synthesis (e.g., in the synthesis of glyphosate).
  • the amount of hydrogenation catalyst for obtaining a given effect is dependent on the particular catalyst used and given set of reductive amination conditions, and with the knowledge gained from the present disclosure, those skilled in the art can determine a suitable amount in each case.
  • any hydrogenation catalyst described above, or combination of catalysts may be present in the reaction mixture, including the solvent such as water, in an amount, or combined amount, from 0.1 wt-% to 10 wt-%, such as from 0.3 wt-% to 5 wt-% or from 0.5 wt- % to 3 wt-%.
  • the hydrogenation catalyst may be present in an amount needed to achieve a weight hourly space velocity (WHSV) as described below.
  • WHSV weight hourly space velocity
  • glycolaldehyde may be converted with a molar selectivity to diethanolamine of from 30% or more to 85% or less, in other embodiments with a molar selectivity of from 40% or more to 80% or less, and in still other embodiments from 50% or more to 75% or less, for example, a molar selectivity of at least 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68,69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84 up to 85%.
  • glycolaldehyde may be converted with a molar selectivity to monoethanolamine of less than 35%, less than 25%, or less than 15%, for example, less than 35, 34, 33, 32, 31, 30, 29, 28, 27, 26, 25, 24, 23, 22, 21, 20, 19, 18, 17, 16 or 15% to monoethanolamine ⁇
  • the molar selectivity to diethanolamine may be at least 1.5 times, or at least two times, the molar selectivity to monoethanolamine.
  • the selectivity improvement may be characterized with respect to a reference molar selectivity, obtained from a reference process in which all reductive ami nation conditions (e.g., pressure, temperature, residence time, feeds (including aminating agent), catalyst(s), etc.) are identical, except for the replacement of the noble metal- containing hydrogenation catalyst with an equal weight of the conventional catalyst, Raney nickel.
  • This material is namely a type of sponge nickel catalyst that is further characterized by being a fine-grained solid composed mostly of nickel that is present as a nickel- aluminum alloy.
  • glycolaldehyde may be converted with a molar selectivity to diethanolamine, which exceeds a reference molar selectivity by at least 15%. That is, in the case of a reference molar selectivity of 15%, the use of the hydrogenation catalyst compared to Raney nickel results in a molar selectivity that is increased to at least 30%.
  • glycolaldehyde may be converted with a molar selectivity to diethanolamine, which exceeds a reference molar selectivity by at least 20%, or even at least 30%.
  • the molar selectivities described above may be obtained at high levels of conversion of glycolaldehyde.
  • the glycolaldehyde conversion may be at least 85%, at least 90%, at least 95%, or even at least 99%.
  • representative yields of diethanolamine may be the same or substantially the same as the molar selectivity ranges given above, such as at least 30% (e.g., from 30% to 85%), at least 40% (e.g., from 40% to 80%), or at least 50% (e.g. , from 50% to 75%), of the theoretical yield obtainable, given that yield is determined as the product of conversion and selectivity.
  • Typical reductive ami nation conditions include an elevated hydrogen partial pressure, such as at least 3 megapascals (MPa) (435 psi), which, in combination with the noble metal-containing hydrogenation catalyst, provide a reductive ami nation environment for carrying out the conversion of glycolaldehyde, selectively to the product diethanolamine.
  • This hydrogen pressure may be contained in a reactor that is used for the contacting of the feed (e.g., an aqueous feed comprising glycolaldehyde) and an aminating agent (e.g., aqueous ammonia), with the noble metal-containing hydrogenation catalyst as described above, to obtain this product.
  • the feed e.g., an aqueous feed comprising glycolaldehyde
  • an aminating agent e.g., aqueous ammonia
  • the reaction mixture, to which the feed and aminating agent are added and from which a product mixture is withdrawn is preferably aqueous and comprises dissolved hydrogen under the reductive amination conditions.
  • the aminating agent may otherwise comprise gaseous ammonia that may be added batchwise or continuously to the reactor, for example it may be added, in the case of continuous operation, with hydrogen or a recycle gas stream comprising hydrogen.
  • gaseous ammonia will generally cause the in situ formation of aqueous ammonia in the presence of an aqueous reaction mixture.
  • aminating agents include primary and secondary amines of the formula NHR 1 R 2 , wherein at least one of R 1 and R 2 is a C1-C3 alkyl group.
  • the glycolaldehyde and aminating agent may be charged to the reactor batchwise, or otherwise continuously added to the reactor, with a molar excess of the aminating agent, for example, with an aminating agenkglycolaldehyde molar ratio of from 2: 1 to 20: 1 or from 5:1 to 15:1.
  • Reductive amination conditions under which the reaction mixture is maintained during the production of diethanolamine, include an elevated pressure and hydrogen partial pressure.
  • Representative absolute reactor pressures are in the range generally from 2.07 MPa (300 psi) to 24.1 MPa (3500 psi), typically from 3.45 MPa (500 psi) to 20.7 MPa (3000 psi), and often from 5.17 MPa (750 psi) to 10.3 MPa (1500 psi).
  • the reactor pressure may be generated predominantly or substantially from hydrogen, such that these ranges of total pressure may also correspond to ranges of hydrogen partial pressure.
  • the presence of gaseous ammonia or other aminating agent, as well as other gaseous species vaporized from the reaction mixture, may result in the hydrogen partial pressure being reduced relative to these total pressures, such that, for example, the hydrogen partial pressure may range generally from 1.38 MPa (200 psi) to 22.4 MPa (3250 psi), typically from 3.00 MPa (435 psi) to 20.0 MPa (2901 psi), and often from 4.82 MPa (700 psi) to 9.31 MPa (1350 psi).
  • reaction time i.e., time at which the reaction mixture is maintained under conditions of pressure and temperature at any target values or target sub-ranges within any of the ranges of pressure and temperature given above (e.g., a target, total pressure value of 8.27 MPa (1200 psi) and a target temperature of 85 °C (l85°F)
  • a target, total pressure value of 8.27 MPa (1200 psi) and a target temperature of 85 °C (l85°F) is from 0.5 hours to 24 hours, and preferably from 1 hour to 5 hours, in the case of a batchwise reaction. For a continuous process, these reaction times correspond to reactor residence times.
  • WHSV weight hourly space velocity
  • the reductive ami nation conditions include a WHSV generally from 0.01 hr 1 to 20 hr 1 , and typically from 0.05 hr 1 to 5 hr 1 .
  • a continuous process involving a heterogeneous (solid) hydrogenation catalyst may be performed by continuous feeding of glycolaldehyde, aminating agent, and hydrogen to the reaction mixture comprising the catalyst and contained within the reactor, and continuous withdrawal, from the reactor, of a product mixture comprising diethanolamine that is substantially free of the catalyst.
  • This product mixture may then be further processed by separating portions of the product mixture to purify and recover the diethanolamine and optionally recycle unconverted reactants, such as the aminating agent and/or hydrogen.
  • the product mixture may be subjected to flash separation to separate a primarily hydrogen-containing vapor phase, at least portion of which (e.g., following the removal of a purge stream to prevent excessive accumulation of unwanted impurities) may provide the recycle gas stream, described above.
  • the liquid phase recovered from the flash separation and also comprising the desired diethanolamine may be subjected to any of a number of possible separation steps, including one or more of phase separation, extraction (e.g., using an organic solvent having preferential affinity for monoethanolamine), and distillation, sequentially in any order. Extraction and distillation may alternatively be combined in a single, extractive distillation step.
  • any separated liquid products e.g.
  • aminating agent and/or unconverted glycolaldehyde may likewise be recycled to the reactor.
  • particular embodiments relate to methods for producing diethanolamine, comprising performing a reductive amination of glycolaldehyde, added to an aqueous reaction mixture with aqueous ammonia as a reactant. This may be performed by contacting this reaction mixture and hydrogen with the noble metal-containing hydrogenation catalyst under reductive ami nation conditions as described above.
  • the reductive ami nation selectively produces diethanolamine according to any of the conversion, selectivity, and yield performance criteria described above, such as a yield of at least about 40% of a theoretical yield.
  • the production of diethanolamine may be integrated with upstream and/or downstream processing steps in the overall production of chemicals, for example sourced from biomass.
  • the glycolaldehyde may be obtained from the pyrolysis of an aldose or a ketose (e.g. , glucose, fructose, or sucrose).
  • representative methods may further comprise synthesizing glyphosate from at least a portion of the diethanolamine. Glyphosate is recognized as a valuable chemical for its use to kill weeds, and particularly annual broadleaf weeds and grasses that compete with crops.
  • diethanolamine may be oxidized using sodium hydroxide (NaOH) and a copper-based catalyst to produce disodium iminodiacetic acid (DSIDA).
  • DSIDA disodium iminodiacetic acid
  • This intermediate is then reacted with phosphorous chloride (PCT) and formaldehyde (HCHO) to produce N- phosphonomethyliminodiacetic acid (PMIDA).
  • PCT phosphorous chloride
  • HCHO formaldehyde
  • the desired glyphosate is thereafter produced by oxidation of PMIDA using sodium molybdate, hydrogen peroxide, and iron (II) sulfate.
  • aspects of the invention relate to increases in reaction selectivity to diethanolamine, by reductive amination of glycolaldehyde, which can be achieved using noble metal-containing hydrogenation catalysts. Efficiencies and the associated economics of synthesis pathways from renewable feeds to high value chemicals are thereby improved.
  • Those having skill in the art with the knowledge gained from the present disclosure, will recognize that various changes can be made to the disclosed catalysts and processes in attaining these and other advantages, without departing from the scope of the present disclosure. As such, it should be understood that the features of the disclosure are susceptible to modifications and/or substitutions.
  • the specific embodiments illustrated and described herein are for illustrative purposes only, and not limiting of the invention as set forth in the appended claims.

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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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Abstract

L'invention concerne des améliorations apportées à des catalyseurs et des procédés associés pour la conversion de glycolaldéhyde en diéthanolamine. Les catalyseurs présentent une sélectivité améliorée vis-à-vis de ce produit souhaité et par conséquent une sélectivité réduite vis-à-vis de la monoéthanolamine, par comparaison avec des procédés classiques. Ces effets bénéfiques sont obtenus par l'utilisation d'un catalyseur d'hydrogénation comprenant au moins un métal noble.
PCT/US2019/043942 2018-08-02 2019-07-29 Procédés et catalyseurs pour la production de diéthanolamine à partir de glycolaldéhyde WO2020028262A1 (fr)

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CN114602461A (zh) * 2020-12-09 2022-06-10 中国科学院大连化学物理研究所 一种催化二元醛制备二元胺的方法

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