EP1856025A1 - Procede pour produire une xylylenediamine - Google Patents

Procede pour produire une xylylenediamine

Info

Publication number
EP1856025A1
EP1856025A1 EP06708480A EP06708480A EP1856025A1 EP 1856025 A1 EP1856025 A1 EP 1856025A1 EP 06708480 A EP06708480 A EP 06708480A EP 06708480 A EP06708480 A EP 06708480A EP 1856025 A1 EP1856025 A1 EP 1856025A1
Authority
EP
European Patent Office
Prior art keywords
hydrogenation
alkali metal
catalyst
nickel
carried out
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Withdrawn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
EP06708480A
Other languages
German (de)
English (en)
Inventor
Martin Ernst
Thilo Hahn
Johann-Peter Melder
Randolf Hugo
Kirsten Dahmen
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
Publication of EP1856025A1 publication Critical patent/EP1856025A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
    • C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
    • C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
    • C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains

Definitions

  • the present invention relates to a process for preparing a xylylenediamine by heterogeneously catalyzed hydrogenation of a phthalonitrile.
  • Xylylenediamine bis (aminomethyl) benzene
  • Xylylenediamine is a useful starting material, e.g. for the synthesis of polyamides, epoxy hardeners or as an intermediate for the preparation of isocyanates.
  • xylylenediamine includes the three isomers orffro-xylylenediamine, mete-xylylenediamine (MXDA) and para-xylylenediamine.
  • the phthalonitriles are solids (for example, melts isophthalonitrile (IPN) at 161 0 C) and have relatively poor solubilities in many organic solvents.
  • US-A-4,482,741 (UOP Inc.) describes the hydrogenation of PDN in the presence of ammonia, a supported Co / Ti catalyst and XDA as a solvent.
  • DE-A-21 64 169 (Mitsubishi Gas Chemical Co., Inc.) describes on page 6, last paragraph, the hydrogenation of IPDN to meta-XDA in the presence of a Ni and / or Co catalyst in ammonia as solvent.
  • JP-B-46008283 (Toray Industries Inc., ACS Abstract 75: 5222) relates to the hydrogenation of nitriles, such as aminocapronitrile, to primary amines in the presence of lead-containing nickel or cobalt catalysts.
  • FR-A1-2 722 784 (Rhone Poulenc) teaches the hydrogenation of dinitriles, such as adiponitrile, to diamines in the presence of Ti-doped Raney nickel catalysts.
  • No. 3,862,911 (and DE-A-2 260 978) (Rhone Poulenc) describes Ni / Cr / Fe / Al catalysts for the hydrogenation of nitriles, in particular adiponitrile.
  • Example 6 B succeeds the hydrogenation of IPDN to MXDA in ethanol at 85 ° C and 40 bar with a yield of only 75%.
  • EP-A1-1 449 825 (Mitsubishi Gas Chem. Comp.) Describes a two-stage preparation of aromatic diamines from aromatic dinitriles, such as IPDN, in the presence of a Pd catalyst in the first stage and in the presence of a Ni or Co catalyst. sators in the second stage.
  • US 2,970,170 and GB-B-821 404 (California Research Corp.) relate to a multi-step production process for xylylenediamines starting from the corresponding phthalic acids.
  • pressures in the range of 1500 to 10,000 psig (103.4 to 689.5 bar), especially 2000 to 5000 psig (137.9 to 344.7 bar), and temperatures in the range of 180 to 400 ° F (82 to 204 ° C) (U.S. Pat., Col. 3, lines 65-71).
  • EP-A1-1 454 895 (Mitsubishi Gas Chem. Comp.) Describes a two-stage process for the hydrogenation of dicyanobenzenes at pressures of 5 to 300 bar, in particular 10 to 200 bar, in the presence of supported or unsupported Co, Ni, Pd , Ru- or Rh catalysts, preferably in the presence of ammonia and optionally in the presence of additives such as alkali metal hydroxides or alkaline earth metal hydroxides.
  • US-B1-6,476,267 (Sagami Chemical Research Center) relates to the preparation of aromatic primary amines from nitriles, such as IPDN, in the presence of supported Ni catalysts and polar solvents, preferably in the presence of NH 3 , at pressures of 0.1 to 50 kg / cm 2 G (0.1 to 49 bar), eg ⁇ 19 kg / cm 2 G (18.6 bar), and temperatures up to 200 ° C.
  • Support material of the Ni catalyst is silica, alumina or activated carbon, preferably silica (all examples).
  • Example 22 the hydrogenation of IPDN in methanol in the presence of NH 3 on a silica-supported Ni catalyst succeeds at 170 ° C and 15 kg / cm 2 G (14.7 bar) in 79.5% yield.
  • GB-B-810 530 Teaches the hydrogenation of iso- or terephthalodinitrile in the presence of ammonia, nickel or cobalt catalysts and aromatic Hydrocarbons, water, DMF, methanol or ethanol as a solvent.
  • the pressure is up to 200 atm. (203 bar).
  • EP-A1-913 388 (Air Products) relates to the hydrogenation of nitriles, such as DMAPN, to amines in the presence of Raney cobalt catalysts, LiOH and water and in the absence of organic solvents, at pressures in the range of 1 to 300 bar, in particular 5 to 80 bar.
  • DE-A1-100 65 031 (Degussa AG) relates to the use of Raney catalysts in the form of hollow bodies in hydrogenation processes.
  • German patent applications with the file references 10341615.3, 10341632.3, 10341614.5, 10341633.1, 10341612.9 and 10341613.7 (BASF AG) of 10.09.03 and the two German patent applications with the file numbers 102004042947.2 and 102004042954.5 (BASF AG) from 02/03/04 relate respectively for the production of XDA.
  • German patent application with the file reference 102005003315.6 (BASF AG) of 24.01.05 describes a process for the preparation of a xylylenediamine by heterogeneously catalyzed hydrogenation of a phthalonitrile in the presence of a cobalt skeleton catalyst.
  • the present invention has for its object to find an improved economical process for the preparation of a xylylenediamine.
  • the method should overcome one or more disadvantages of the prior art methods.
  • the xylylenediamine, in particular MXDA, should thereby be obtained in high yield, in particular space-time yield, selectivity, purity and / or color quality.
  • a process for the preparation of a xylylenediamine by heterogeneously catalyzed hydrogenation of a phthalonitrile is characterized in that the hydrogenation in the presence of a nickel skeletal catalyst, water, an alkali metal hydroxide and an ether as a solvent, at an absolute pressure in the range of 1 to 100 bar, at a temperature in the range of 40 to 150 ° C and without addition of ammonia is performed.
  • the process according to the invention is preferably used for the preparation of meta-xylylenediamine (MXDA) by hydrogenation of isophthalonitrile (IPDN).
  • MXDA meta-xylylenediamine
  • IPDN isophthalonitrile
  • Advantages of the method according to the invention include the, due to the driving without NH 3 addition and low pressure driving, lower technical equipment and safety expenses and thus lower fixed costs (investment) and variable costs.
  • the PDN used in the process as starting material can be synthesized in a previous stage by ammoxidation of the corresponding xylene isomer. Such synthesis methods are e.g. in BASF patent applications EP-A-767 165,
  • the starting material PDN is preferably used in a purity of> 90% by weight, in particular> 98% by weight, e.g. 98.2 to 99.9 wt .-%, used.
  • Such purities may e.g. obtained by distillation or rectification of commercially available goods.
  • the hydrogenation process according to the invention is preferably used in the presence of from 0.5 to 15% by weight, especially from 2 to 10% by weight, very particularly from 2.5 to 7% by weight, in particular from 3 to 5% by weight, of water, each based on the used PDN performed.
  • the PDN is dissolved and / or suspended in an ether.
  • the dissolution process at elevated temperature e.g. at 50 to 145 ° C, take place.
  • the solvent and / or suspending agent used is preferably a C 4-12 -dialkyl ether and / or C 3-12 -alicyclic ether, in particular a C 4-6 -dialkyl ether and / or C 4-6 -alicyclic ether.
  • THF methyl tert-butyl ether
  • DEE diethyl ether
  • THF tetrahydrofuran
  • THF tetrahydrofuran
  • THF tetrahydropyran
  • 1,3-dioxepane 1,4-dioxane
  • 1,3-dioxane 1,3-dioxolane.
  • Particularly preferred is THF.
  • solvent and / or suspending agent it is also possible to use a mixture of two or more of the solvents mentioned.
  • a nickel-skeletal catalyst is used according to the invention.
  • Typical examples of such catalysts are Raney TM nickel catalysts.
  • the active catalyst as .Metallschwamm 'from a binary alloy of nickel and optionally other elements with z.
  • the catalysts used in the process according to the invention are preferably prepared starting from an alloy of nickel and a further alloying component which is soluble in alkalis.
  • a further alloying component which is soluble in alkalis.
  • aluminum is preferably used, but other components such as zinc and silicon or mixtures of such components may be used.
  • the soluble alloy component is wholly or partially extracted with alkali, for which example aqueous sodium hydroxide solution can be used.
  • alkali for which example aqueous sodium hydroxide solution can be used.
  • the catalyst can then z. B. be washed with water or organic solvents.
  • promoters are metals of subgroups IB, VIB and / or VIII of the periodic table, such as chromium, iron, molybdenum, cobalt, copper, etc.
  • Activation of the catalysts by leaching the soluble component may be either in the reactor itself or prior to charging to the reactor.
  • the preactivated catalysts are sensitive to air and pyrophoric and are therefore usually under a medium such.
  • a medium such as water, an organic solvent or a substance that is present in the reaction according to the invention (solvent, starting material, product) stored and handled or embedded in an organic compound which is solid at room temperature.
  • the catalysts can be used as powders for suspension hydrogenations, as granules or as shaped articles such as tablets or extrudates for fixed bed reactors.
  • a nickel skeletal catalyst which is prepared from a Ni / Al alloy by leaching with aqueous alkali metal hydroxide solution, e.g. Sodium hydroxide solution, and subsequent washing with water was obtained, and preferably as promoters at least one of the elements Fe, Cr contains.
  • aqueous alkali metal hydroxide solution e.g. Sodium hydroxide solution
  • Such activated catalysts typically still contain nickel besides nickel
  • 0-10 wt.% Cr especially 0.1-7 wt.% Cr, very particularly 1-4 wt.% Cr, and / or 0-10 wt.% Fe, especially 0.1-7 %
  • Fe very particularly 1 to 4% by weight of Fe, the weight data in each case being based on the total weight of catalyst.
  • a nickel skeleton catalyst A 4000 from Johnson Matthey can advantageously be used as the catalyst in the process according to the invention.
  • This catalyst has the following composition:
  • Al ⁇ 14% by weight
  • Ni > 80% by weight
  • Fe 1 to 4% by weight
  • Cr 1 to 4% by weight.
  • the nickel skeletal catalyst employed does not contain lead (Pb) and / or cobalt (Co) and / or transition group IVB metal, i. no Ti, Zr and / or Hf.
  • the PDN is in the presence of alkali metal hydroxide (MOH), especially 0.001 to 5 mol% MOH, more preferably 0.002 to 1.5 mol% MOH, more preferably 0.005 to 1.2 mol% MOH, e.g. 1 mol%, MOH, in each case based on the PDN used reacted.
  • MOH alkali metal hydroxide
  • the appropriate amount of MOH is an aqueous solution, e.g. as 1 to 25 wt .-% aqueous solution used.
  • Possible alkali metals M are Li, Na, K, Rb and Cs.
  • M is K or Na.
  • M K.
  • the catalyst used is previously treated with an alkali metal hydroxide (M'OH) or a mixture of two or more alkali metal hydroxides M'OH, for example a mixture of NaOH and KOH. This treatment is particularly advantageous when the hydrogenation is carried out in the absence of MOH in the initial reaction mixture.
  • This treatment of the catalyst with M 1 OH can be carried out by methods known to the person skilled in the art, for example by saturating the catalyst with M'OH, for example from 0.01 to 5.0% by weight of M'OH (based on the support material) Presence of a suitable solvent, eg water. (EP-A1-913388, US 6,429,338, US 3,636,108).
  • M ' are Li, Na, K, Rb and Cs.
  • M ' K or Na.
  • M ' K.
  • the hydrogenation is carried out without the addition of ammonia.
  • the reaction temperature of the hydrogenation is in the range of 40 to 150 0 C, preferably 50 to 120 0 C, in particular 60 to 110 ° C, especially 70 and 105 0 C 1, for example 80 to 100 ° C.
  • the absolute pressure in the hydrogenation is in the range from 1 to 100 bar, preferably from 2 to 80 bar, in particular from 5 to 60 bar, very particularly from 10 to 50 bar, e.g. 20 to 40 bar.
  • the hydrogenation is preferably carried out in a reaction stage. That Advantageously, several hydrogenation stages, e.g. taught in EP-A1-1 449 825 and EP-A1-1 454 895.
  • reactors for the process according to the invention for example, conventional high-pressure autoclave can be used.
  • the reactors known to the person skilled in the art for this reaction for example fixed-bed or suspension operation
  • processes continuously, semibatch, batch
  • suspension mode a continuous process or semibatch process is preferred.
  • the hydrogenation reactor can be run in straight passage.
  • a circulation mode of operation is possible in which a portion of the reactor output at the reactor gate input is returned, preferably without prior processing of the circulating current.
  • an optimal dilution of the reaction solution can be achieved, which has a favorable effect on the selectivity.
  • the circulation stream can be cooled by means of an external heat exchanger in a simple and cost-effective manner and thus the heat of reaction can be dissipated.
  • the reactor can also be operated adiabatically, wherein the temperature rise of the reaction solution can be limited by the cooled circulation stream. Since the reactor does not have to be cooled even then, a simple and cost-effective design is possible.
  • An alternative is a cooled tube bundle reactor.
  • the nickel skeleton catalyst, the alkali metal hydroxide and water in the reactor are preferably initially charged and subsequently under the reaction conditions (pressure, temperature) the phthalonitrile in the solvent over a certain period of time (eg 2 to 8 hours). closed (semi-continuous driving).
  • the XDA corresponding to the PDN used is additionally presented with, for example, in amounts of 500-1500% by weight, based on the PDN to be used.
  • the XDA corresponding to the PDN used is the ortho-XDA, in the case of the meta-dinitrile the MXDA and in the case of the para-dinitrile the para-XDA.
  • the conversions of PDN achievable with the process according to the invention are in the range of> 95%, in particular> 99%, e.g. > 96 to 99.9% or 99.5 to 100%, with selectivities (for the formation of XDA) in the range of ⁇ 80%, in particular> 85%, e.g. 86 to 99.5% or 90 to 99%.
  • the solvent-freed reaction product contains, in particular, ⁇ 2% by weight, very particularly ⁇ 1% by weight, e.g. 0 to 0.5% by weight, amidines of formula I and / or higher than the XDA boiling products, e.g. the corresponding (bisaminoalkyl) diarylamine II.
  • the isolation of the XDA can be carried out, for example, by distillation or rectification.
  • the autoclave was closed, the mixture made inert, and pressed to 10 bar Wasseroff. It was heated to 100 ° C. under autogenous pressure and with stirring (500 rpm). Upon reaching this temperature was pressed to 36 bar of hydrogen and the stirrer speed to 1200 rev / min, increased. Subsequently, a solution of 7.2 g of IPDN in 83 g of THF was pumped in over 5 hours, while hydrogen was continuously fed (under pressure maintenance of 32-36 bar).
  • the autoclave was closed, the mixture made inert, and pressed to 10 bar hydrogen. It was heated to 100 ° C. under autogenous pressure and with stirring (500 rpm). Upon reaching this temperature, hydrogen was injected to 36 bar and the stirrer speed was increased to 1200 rpm. Subsequently, a solution of 7.2 g of IPDN in 83 g of THF was pumped in over 1 h, while hydrogen was continuously fed (under pressure maintenance at 32-36 bar).

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

Abstract

L'invention concerne un procédé pour produire une xylyènediamine par hydrogénation catalysée de manière hétérogène d'un phtalodinitrile, l'hydrogénation en présence d'un catalyseur à squelette en nickel, d'eau, d'un hydroxyde de métaux alcalis et d'un éther utilisés en tant que solvants est effectuée à une pression comprise entre 1 et 100 bar, à une température comprise entre 40 et 150°C, sans ajout d'ammoniac.
EP06708480A 2005-02-24 2006-02-23 Procede pour produire une xylylenediamine Withdrawn EP1856025A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005008929A DE102005008929A1 (de) 2005-02-24 2005-02-24 Verfahren zur Herstellung eines Xylylendiamins
PCT/EP2006/060226 WO2006089931A1 (fr) 2005-02-24 2006-02-23 Procede pour produire une xylylenediamine

Publications (1)

Publication Number Publication Date
EP1856025A1 true EP1856025A1 (fr) 2007-11-21

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Family Applications (1)

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EP06708480A Withdrawn EP1856025A1 (fr) 2005-02-24 2006-02-23 Procede pour produire une xylylenediamine

Country Status (7)

Country Link
US (1) US20080154061A1 (fr)
EP (1) EP1856025A1 (fr)
JP (1) JP2008531521A (fr)
KR (1) KR20070105382A (fr)
CN (1) CN101128416A (fr)
DE (1) DE102005008929A1 (fr)
WO (1) WO2006089931A1 (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102005003315A1 (de) * 2005-01-24 2006-08-03 Basf Ag Verfahren zur Herstellung eines Xylylendiamins
WO2007014901A1 (fr) 2005-08-02 2007-02-08 Basf Se Procede pour preparer de la diamine de xylylene par hydratation continue de phthalodinitrile
DE102005045806A1 (de) * 2005-09-24 2007-03-29 Basf Ag Verfahren zur Herstellung von Xylylendiamin
EP1984320B1 (fr) 2006-02-01 2013-10-23 Basf Se Procede de production de xylylenediamine pure (xda)
EP2150342B1 (fr) * 2007-05-29 2018-02-21 Evonik Degussa GmbH Catalyseurs de métal de base activés
BRPI0721719A2 (pt) * 2007-05-29 2013-02-13 Evonik Degussa Gmbh catalisadores baseados em metais ativados
CN101678335B (zh) 2007-05-29 2014-04-16 赢创德固赛有限责任公司 活化的贱金属催化剂
KR101440178B1 (ko) 2007-10-15 2014-09-12 에보니크 데구사 게엠베하 급속 여과형 분체 촉매 혼합물
WO2010026920A1 (fr) * 2008-09-08 2010-03-11 三菱瓦斯化学株式会社 Procédé de production de xylylènediamine
CN103339098B (zh) * 2011-01-31 2015-04-22 三菱瓦斯化学株式会社 苯二甲胺的制造方法
CN102180799A (zh) * 2011-03-23 2011-09-14 南通泰禾化工有限公司 一种对苯二甲胺的制备方法
US20230265042A1 (en) * 2020-07-22 2023-08-24 Mitsubishi Gas Chemical Company, Inc. Method for producing aromatic aminomethyl

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DE502004005974D1 (de) * 2003-09-10 2008-03-06 Basf Ag Verfahren zur herstellung von xylylendiamin durch kontinuierliche hydrierung von flüssigem phthalodinitril
DE102005003315A1 (de) * 2005-01-24 2006-08-03 Basf Ag Verfahren zur Herstellung eines Xylylendiamins

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Also Published As

Publication number Publication date
JP2008531521A (ja) 2008-08-14
DE102005008929A1 (de) 2006-08-31
KR20070105382A (ko) 2007-10-30
US20080154061A1 (en) 2008-06-26
CN101128416A (zh) 2008-02-20
WO2006089931A1 (fr) 2006-08-31

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