EP1937625A1 - Procede pour produire de l'aminodiglycol (adg) et de la morpholine - Google Patents

Procede pour produire de l'aminodiglycol (adg) et de la morpholine

Info

Publication number
EP1937625A1
EP1937625A1 EP06793775A EP06793775A EP1937625A1 EP 1937625 A1 EP1937625 A1 EP 1937625A1 EP 06793775 A EP06793775 A EP 06793775A EP 06793775 A EP06793775 A EP 06793775A EP 1937625 A1 EP1937625 A1 EP 1937625A1
Authority
EP
European Patent Office
Prior art keywords
catalyst
reaction
morpholine
adg
reactor
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Withdrawn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
EP06793775A
Other languages
German (de)
English (en)
Inventor
Bram Willem Hoffer
Holger Evers
Petr Kubanek
Till Gerlach
Johann-Peter Melder
Frank Funke
Matthias Frauenkron
Helmut Schmidtke
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.)
BASF SE
Original Assignee
BASF SE
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 BASF SE filed Critical BASF SE
Priority to EP06793775A priority Critical patent/EP1937625A1/fr
Publication of EP1937625A1 publication Critical patent/EP1937625A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups

Definitions

  • the present invention relates to a process for the preparation of aminodiglycol (ADG) and morpholine by reaction of diethylene glycol (DEG) of the formula
  • Aminodiglycol (ADG) and morpholine find inter alia. Use as solvents, stabilizers, for the synthesis of chelating agents, synthetic resins, pharmaceuticals, inhibitors and surfactants.
  • ADG aminodiglycol
  • morpholine For the preparation of aminodiglycol (ADG) and morpholine numerous methods are described in the literature.
  • EP-A-36331 and US-A-4,647,663 describe a process for the preparation of morpholine and morpholine derivatives by reacting a dialkylene glycol with ammonia in the presence of H2 and a hydrogenation catalyst in a trickle bed reactor.
  • Khim. Prom-st. (Moscow) (1 1), 653-5 (1982) (Chem. Abstr. 98: 91383q) describes the preparation of morpholine by gas-phase cycloamination of diethylene glycol with ammonia in the presence of H2 and a Cu, Co or Ni. Cr2 ⁇ 3 catalyst.
  • a parallel German patent application with the same filing date (BASF AG) relates to a process for the preparation of ethylene amines by reacting ethylenediamine (EDA) in the presence of specific heterogeneous catalyst molding.
  • a parallel German patent application with the same filing date (BASF AG) relates to a process for the preparation of ethylene amines by reacting monoethanolamine (MEOA) with ammonia in the presence of specific heterogeneous catalyst shaped bodies.
  • MEOA monoethanolamine
  • ADG aminodiglycol
  • the method is intended in particular the non-cyclic amine ADG of the formula
  • the proportion of ADG to morpholine in the product mix should be increased compared to the prior art, especially at a high DEG conversion, in particular at a DEG conversion of greater than 85%.
  • ADG aminodiglycol
  • DEG diethylene glycol
  • the volume can also be calculated using the following method, where:
  • the surface can also be calculated theoretically by the following method, in which one defines an envelope of the molding, the curve radii max. 5 ⁇ m (in order not to take the inner pore surface into the pores by "penetrating" the envelope) and which touches the mold body as intimately as possible (no cut surface with the support) and then creates a vacuum from the inside, so that the film lays as close as possible to the molding.
  • the diethylene glycol (DEG) required as starting material can be prepared by known processes, for example by reacting ethylene oxide (EO) with H 2 O or EO with monoethylene glycol.
  • EO ethylene oxide
  • the reaction according to the invention is generally carried out at an absolute pressure in the range of 1-260 bar, preferably 100-250 bar, in particular at 150-240 bar, especially at 175-225 bar, and generally at elevated temperature, e.g. in the temperature range of 100-300 ° C, in particular 130-240 ° C, preferably at 175-225 ° C.
  • the ratio of morpholine: ADG is determined in the process according to the invention in particular by the DEG conversion and the molar ratio NH 3: DEG.
  • the catalysts are preferably used in the form of catalysts which either consist only of catalytically active material and optionally a molding assistant (such as graphite or stearic acid), or the catalytically active components on a substantially inactive Su- material.
  • a molding assistant such as graphite or stearic acid
  • the catalytically active composition can be introduced into the reaction vessel as a powder or as a grit or, after milling, mixing with molding aids, shaping and heat treatment, as a shaped catalyst body - for example as tablets, spheres, rings, extrudates (eg strands, tubes) - in be introduced into the reactor.
  • the concentration data (in% by weight) of the components of the catalyst are in each case - unless stated otherwise - on the catalytically active composition of the catalyst prepared before treatment with hydrogen.
  • the catalytically active mass of the catalyst is defined as the sum of the masses of the catalytically active constituents and contains, prior to treatment with hydrogen, preferably substantially the catalytically active constituents oxygen-containing compounds of aluminum and / or zirconium, copper, nickel and cobalt.
  • the sum of the o.g. catalytically active constituents, calculated as Al 2 O 3, ZrO 2, CuO, NiO and CoO, in the catalytically active composition prior to treatment with hydrogen is for example 70 to 100 wt .-%, preferably 80 to 100 wt .-%, particularly preferably 90 to 100 wt .-%, in particular 95 to 100 wt .-%, most preferably> 99 to 100 wt .-%.
  • Preferred heterogeneous catalysts in the process according to the invention contain in their catalytically active composition prior to treatment with hydrogen
  • oxygen-containing compounds of nickel calculated as NiO, wherein preferably the molar ratio of nickel to copper greater than 1, in particular greater than 1, 2, very particularly 1, 8 to 8.5, and
  • the oxygen-containing compounds of copper, nickel and cobalt, each calculated as CuO, NiO and CoO, of the preferred catalysts are generally generally in amounts of 15 to 80 wt .-%, preferably 35 to 80 wt .-%, particularly preferred 60 to 78 wt .-%, in the catalytically active composition (before treatment with Hydrogen), wherein particularly preferably the molar ratio of nickel to copper is greater than 1.
  • catalysts comprising cobalt, nickel and copper and alumina having a metal content of 5 to 80 wt .-%, in particular 10 to 30 wt .-%, based on the total catalyst, wherein the catalysts, calculated on the metal content, contain from 70 to 95% by weight of a mixture of cobalt and nickel and from 5 to 30% by weight of copper, and wherein the weight ratio of cobalt to nickel is 4: 1 to 1: 4, in particular 2: 1 to 1: 2, is, for example, the catalyst used in the examples there with the composition 10 wt .-% CoO, 10 wt .-% NiO and 4 wt .-% CuO to Al 2 O 3 ,
  • EP-A-382 049 disclosed or correspondingly preparable catalysts whose catalytically active composition prior to treatment with hydrogen 20 to 85 wt .-%, preferably 70 to 80 wt .-%, ZrO 2 and / or AI 2 O 3 , 1 to 30 wt .-%, preferably 1 to 10 wt .-%, CuO, and in each case 1 to 40 wt .-%, preferably 5 to 20 wt .-%, CoO and NiO contains, for example, those in loc. cit. 76 wt% Zr calculated as ZrO 2 , 4 wt% Cu, calculated as CuO, 10 wt% Co, calculated as CoO, and 10 wt% Ni, on page 6 calculated as NiO,
  • EP-A-963 975 and EP-A-1 106 600 both BASF AG, whose catalytically active composition before treatment with hydrogen contains from 22 to 40% by weight ZrO 2 ,
  • Particularly preferred catalysts in the process according to the invention contain no chromium (Cr).
  • the catalyst is preferably at a temperature in the range of 100 to 500 ° C, especially 150 to 400 ° C, especially 180 to 300 ° C, over a period of at least 25 min., Particularly at least 60 min., A hydrogen - exposed to a living atmosphere or a hydrogen atmosphere.
  • the period of activation of the catalyst may be up to 1 h, especially up to 12 h, in particular up to 24 h.
  • At least a portion of the oxygen-containing metal compounds present in the catalysts is reduced to the corresponding metals, so that they are present together with the various oxygen compounds in the active form of the catalyst.
  • the catalyst used preferably has a bulk density in the range of 0.6 to 1.2 kg / l.
  • ADG selectivities are obtained when the catalyst is used in the form of small shaped articles.
  • a small shaped body are meant those whose diameter in spherical shape in each case below 3 mm, in particular below 2.5 mm, e.g. in the range of 1 to 2 mm.
  • a small shaped body those are also meant whose diameter in strand form (strand length >> strand diameter) or their height in the case of tablet form (tablet diameter >> tablet height) is in each case below 3 mm, in particular below 2.5 mm, e.g. in the range of 1 to 2 mm.
  • the catalyst is preferably present as a fixed bed in a reactor.
  • the reactor is preferably a tube reactor or tube bundle reactor.
  • the reaction of DEG in the reactor preferably takes place in a straight pass.
  • the catalyst bed is preferably surrounded by an inert material both at the inlet and at the outlet of the reactor.
  • an inert material e.g. Pall rings
  • balls of an inert material e.g., ceramic, steatite, aluminum
  • an inert material e.g., ceramic, steatite, aluminum
  • the reactor can be operated in both bottom and trickle mode.
  • a liquid distributor for the reactor feed is preferably used at the inlet of the reactor.
  • catalyst activity are preferably 0.01 to 1, 00 wt .-%, especially 0.20 to 0.60 wt .-%, hydrogen (based on the reactor feed DEG + NH3) in the reactor.
  • WHSV weight hourly space velocity
  • S selectivities
  • ADG and morpholine will be in a weight ratio ADG: morpholine greater than 0.20, especially greater than 0.24, especially greater than 0.27, e.g. in the range of 0.28 to 0.36.
  • the workup of the product streams obtained in the process according to the invention which contain, in particular, the particularly desired ADG but also morpholine, morpholine derivatives, higher polyalkylamines and unreacted DEG, can be carried out by distillation processes known to the person skilled in the art.
  • the distillation columns required for the pure distillation of the individual products, above all the particularly desired ADGs and also morpholines, can be designed by methods familiar to the person skilled in the art (eg number of separation stages, reflux ratio, etc.).
  • the separation of the reaction product resulting from the reaction takes place in particular by multi-stage distillation.
  • the separation of the reaction effluent resulting from the reaction into two separation sequences is carried out by multistage distillation, wherein in the first separation sequence ammonia and optionally present hydrogen are separated off and in the second separation sequence a separation into unreacted DEG and ADG, morpholine, Morpholine derivatives and higher polyalkylamines takes place.
  • an aqueous solution of nickel nitrate, copper nitrate, cobalt nitrate and zirconium acetate was added simultaneously with a 20% aqueous solution of sodium carbonate into a stirring vessel at a temperature of 70 ° C. in a constant flow so that the pH was within a range of 5.5 - 6.0 was maintained.
  • the metal salt solution and the sodium carbonate solution was stirred for a further hour at 70 ° C and then the pH was increased by the addition of some sodium carbonate solution to a value of 7.4.
  • the suspension obtained was filtered and the filter cake was washed with demineralized water. Thereafter, the filter cake was dried at a temperature of 200 ° C in a drying oven or a spray dryer. The hydroxide carbonate mixture obtained in this way was then tempered at a temperature of 400 ° C over a period of 2 hours.
  • the catalyst powder thus obtained had the composition:
  • the catalyst powder of A1 was mixed with 2% by weight of graphite and shaped into 5 ⁇ 3 mm tablets. After tabletting, the tablets were post-calcined for 2 h at 350 ° C in a muffle furnace. Before installation in the test reactor, it was reduced and then passivated. For the reduction, the catalyst was heated in a hydrogen / nitrogen stream to temperatures between 100 and 200 ° C. This temperature was maintained until no more water has formed. It was then heated to a final temperature of 280 ° C and held this temperature for 90-120 hours. The catalyst was cooled to room temperature under a nitrogen stream and then passivated with a dilute oxygen stream. During passivation, care was taken that the temperature in the reactor did not rise above 50 ° C at any point.
  • the catalyst powder of A1 was mixed with 2% by weight of graphite and shaped into 1.5 ⁇ 2 mm tablets.
  • the post-calcination, reduction and passivation was carried out as described in A2.
  • Example 1 small shaped article (catalyst B), according to the invention
  • ADG 31, 4% by weight of morpholine: 32.1% by weight
  • ADG 28.7% by weight of morpholine: 43.7% by weight
  • ADG 20.6% by weight of morpholine: 60.2% by weight
  • Morpholine 46.9% by weight

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

L'invention concerne un procédé pour produire de l'aminodiglycol (ADG) et de la morpholine par mise en réaction de diéthylène glycol (DEG) avec de l'ammoniac en présence d'un catalyseur hétérogène de métal de transition. L'invention est caractérisée en ce que la matière catalytiquement active du catalyseur, avant le traitement à l'hydrogène, contient des composés à teneur en oxygène d'aluminium et/ou de zirconium, de cuivre, de nickel et de cobalt. L'élément moulé catalyseur, lorsqu'il est de forme sphérique ou allongée, a un diamètre < 3 mm, lorsqu'il est en forme de pastille, il a une hauteur < 3 mm et, pour toutes les autres géométries, il a un diamètre équivalent L = 1/a' < 0,70 mm, a' étant la superficie externe par unité de volume (mms2/mmp3), pour une formule (AA), Ap étant la superficie externe de la particule de catalyseur (mms2) et Vp le volume de la particule de catalyseur (mmp3).
EP06793775A 2005-09-30 2006-09-25 Procede pour produire de l'aminodiglycol (adg) et de la morpholine Withdrawn EP1937625A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP06793775A EP1937625A1 (fr) 2005-09-30 2006-09-25 Procede pour produire de l'aminodiglycol (adg) et de la morpholine

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE102005047458A DE102005047458A1 (de) 2005-09-30 2005-09-30 Verfahren zur Herstellung von Aminodiglykol (ADG) und Morpholin
EP06101339 2006-02-06
EP06793775A EP1937625A1 (fr) 2005-09-30 2006-09-25 Procede pour produire de l'aminodiglycol (adg) et de la morpholine
PCT/EP2006/066665 WO2007036496A1 (fr) 2005-09-30 2006-09-25 Procede pour produire de l'aminodiglycol (adg) et de la morpholine

Publications (1)

Publication Number Publication Date
EP1937625A1 true EP1937625A1 (fr) 2008-07-02

Family

ID=37648393

Family Applications (1)

Application Number Title Priority Date Filing Date
EP06793775A Withdrawn EP1937625A1 (fr) 2005-09-30 2006-09-25 Procede pour produire de l'aminodiglycol (adg) et de la morpholine

Country Status (5)

Country Link
US (1) US20080255351A1 (fr)
EP (1) EP1937625A1 (fr)
JP (1) JP2009510018A (fr)
DE (1) DE102005047458A1 (fr)
WO (1) WO2007036496A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023135035A1 (fr) 2022-01-14 2023-07-20 Basf Se Procédé de fabrication ou de conversion d'alcanolamines

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WO2007036499A1 (fr) 2005-09-30 2007-04-05 Basf Se Procede de production d'ethyleneamines
EP1934165B1 (fr) 2005-09-30 2009-11-11 Basf Se Procede de production d'ethyleneamines
JP4938802B2 (ja) 2006-02-14 2012-05-23 ビーエーエスエフ ソシエタス・ヨーロピア モノエチレングリコール（ｍｅｇ）からのエチレンアミン及びエタノールアミンの製造方法
US7635790B2 (en) * 2006-02-14 2009-12-22 Basf Se Method for producing ethylene amines and ethanol amines by the hydrogenating amination of monoethylene glycol and ammonia in the presence of a catalyst
RU2009104740A (ru) 2006-07-14 2010-08-27 Басф Се (De) Способ получения амина
CN101489981B (zh) 2006-07-14 2013-03-20 巴斯夫欧洲公司 生产胺的方法
CN101489982A (zh) 2006-07-14 2009-07-22 巴斯夫欧洲公司 生产胺的方法
US7919655B2 (en) 2006-07-14 2011-04-05 Basf Se Method for producing an amine
CN101489673A (zh) * 2006-07-14 2009-07-22 巴斯夫欧洲公司 生产胺的方法
CN101484105B (zh) * 2006-07-20 2012-04-18 Sca卫生产品股份公司 用于形成气流成网吸收芯体的设备和方法
WO2008037590A1 (fr) 2006-09-28 2008-04-03 Basf Se Procédé pour la séparation continue par distillation de mélanges contenant de la morpholine, du mono-amino-diglycol, de l'ammoniac et de l'eau
WO2008037659A1 (fr) * 2006-09-28 2008-04-03 Basf Se Procédé pour la production de 2,2'-aminoéthoxyéthanol de qualité électronique
JP5200023B2 (ja) 2006-09-28 2013-05-15 ビーエーエスエフ ソシエタス・ヨーロピア モルホリン（ｍｏ）、モノアミノジグリコール（ａｄｇ）、アンモニア及び水を含有する混合物を連続的に蒸留により分離するための方法
US8197646B2 (en) 2006-09-28 2012-06-12 Basf Se Processes for continuous fractional distillation of mixtures comprising morpholine, monoaminodiglycol, ammonia and water
ATE553844T1 (de) * 2007-12-21 2012-05-15 Basf Se Verfahren zur herstellung eines amins
US8324430B2 (en) 2007-12-21 2012-12-04 Basf Se Processes for preparing amines and catalysts for use therein
CN101903092B (zh) 2007-12-21 2013-03-20 巴斯夫欧洲公司 生产胺的方法
US8278489B2 (en) 2007-12-21 2012-10-02 Basf Se Method for producing an amine
DK2237869T3 (da) * 2008-01-25 2011-12-05 Basf Se Reaktor til gennemførelse af højtryksreaktioner, fremgangsmåde til ibrugtagning samt fremgangsmåde til gennemførelse af en reaktion
EP2346602B1 (fr) 2008-09-19 2014-03-19 Basf Se Procédé de préparation en continu d'une amine au moyen d'un catalyseur à base d'aluminium et de cuivre
EP2488483B1 (fr) 2009-10-06 2014-06-25 Alkyl Amines Chemicals Ltd Procédé de préparation de 2-(2-aminoéthoxy) éthanol (2aee) et morpholine avec 2aee: morpholine >3
CN102781571B (zh) * 2009-12-03 2015-06-17 巴斯夫欧洲公司 用于制备胺的催化剂和方法
EP2506966B1 (fr) 2009-12-03 2017-08-16 Basf Se Catalyseur et procédé de production d'une amine
CN102933549B (zh) 2010-06-15 2015-08-12 巴斯夫欧洲公司 制备环状叔甲基胺的方法
US8637668B2 (en) 2010-06-15 2014-01-28 Basf Se Process for preparing a cyclic tertiary methylamine
US8933223B2 (en) 2010-10-14 2015-01-13 Basf Se Process for preparing a cyclic tertiary amine
WO2012049101A1 (fr) 2010-10-14 2012-04-19 Basf Se Procédé de production d'une amine tertiaire cyclique
IN2014DN10668A (fr) 2012-06-01 2015-08-28 Basf Se
US8884015B2 (en) 2012-06-01 2014-11-11 Basf Se Process for the preparation of a mono-N-alkypiperazine
US8981093B2 (en) 2012-06-06 2015-03-17 Basf Se Process for preparing piperazine
CN111741950B (zh) 2018-02-22 2024-03-05 巴斯夫欧洲公司 贫化2-甲氧基乙醇(moe)的方法
US11518749B2 (en) 2018-02-22 2022-12-06 Basf Se Method for the continuous separation by distillation of mixtures that contain morpholine (MO), monoaminodiglycol (ADG), ammonia, water and methoxyethanol (MOE)

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Also Published As

Publication number Publication date
JP2009510018A (ja) 2009-03-12
WO2007036496A1 (fr) 2007-04-05
US20080255351A1 (en) 2008-10-16
DE102005047458A1 (de) 2007-04-12

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