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WO2008104579A1 - Procédé de fabrication d'éthylène-diamine-diacétonitrile - Google Patents

Procédé de fabrication d'éthylène-diamine-diacétonitrile Download PDF

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Publication number
WO2008104579A1
WO2008104579A1 PCT/EP2008/052407 EP2008052407W WO2008104579A1 WO 2008104579 A1 WO2008104579 A1 WO 2008104579A1 EP 2008052407 W EP2008052407 W EP 2008052407W WO 2008104579 A1 WO2008104579 A1 WO 2008104579A1
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WO
WIPO (PCT)
Prior art keywords
eddn
mol
eda
edmn
formaldehyde
Prior art date
Application number
PCT/EP2008/052407
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German (de)
English (en)
Inventor
Kirsten Dahmen
Alfred Oftring
Randolf Hugo
Thilo Hahn
Katrin Baumann
Johann-Peter Melder
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 WO2008104579A1 publication Critical patent/WO2008104579A1/fr

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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
    • C07C211/02—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C211/14—Amines containing amino groups bound to at least two aminoalkyl groups, e.g. diethylenetriamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups

Definitions

  • the invention relates to a process for the preparation of ethylenediaminediacetonitrile (EDDN) starting from ethylenediamine (EDA), formaldehyde and hydrogen cyanide (HCN).
  • EDDN ethylenediaminediacetonitrile
  • HCN hydrogen cyanide
  • EDMN ethylenediamine monoacetonitrile
  • This oleaginous product contains not only a cyclic compound but also EDMN as a minor component.
  • the reaction was carried out with exclusion of water.
  • the oily product is then further reacted in a multi-step process to the desired 2-piperazinone derivatives.
  • this document also describes the preparation of EDDN.
  • EDDN is obtained if a molar excess of EDA with FACH is reacted in methanol at 55 to 60 0 C.
  • the product isolation is carried out by vacuum distillation. In this case, a yield of about 27.3% based on the EDA used is obtained.
  • US-A 2006/0041 170 relates to a process for the preparation of triethylenetetraamine (TETA), in particular of TETA salts and their use as medicaments.
  • EDDN is used as starting material.
  • EDDN can be prepared in principle by two methods. On the one hand EDDN can be prepared by direct alkylation of EDA with a haloacetonitrile such as chloro or bromoacetonitrile.
  • EDDN is prepared by the above-described reaction of EDA, in particular the dihydrochloride of EDA, first with formaldehyde and then with cyanogen salts such as KCN. The reaction product obtained is additionally treated with an acid.
  • EDA is used as the educt, there is first an additional conversion of EDA into its salt form, in particular into the dihydrochloride, before it is reacted further with formaldehyde.
  • a disadvantage of this process is the salt attack through the use of cyanogen salts. Also disadvantageous is the solids handling of EDA salts, since EDA is either used directly as a salt or is first converted into a salt.
  • the method described in US-A 2006/0041170 is not suitable for continuous use.
  • the resulting EDDN is then derivatized with compounds such as benzaldehyde or compounds containing Boc protecting groups. These protected EDDN derivatives are hydrogenated to give the corresponding TETA derivatives, from which in turn the appropriate TETA salts are liberated with acids.
  • the object underlying the present invention is to provide a simplified process for the preparation of EDDN and optionally of EDMN.
  • the object is achieved by a process for the preparation of ethylenediaminediacetonitrile (EDDN), whereby ethylenediamine (EDA) with formaldehyde and hydrocyanic acid (HCN) is reacted, wherein the molar ratio of EDA to formaldehyde to HCN 1: 1, 5: 1, 5 to 1: 2: 2 [mol / mol / mol].
  • EDDN ethylenediaminediacetonitrile
  • HCN hydrocyanic acid
  • a further advantage of the process according to the invention is that cyanogen salts such as KCN and Ca (CN) 2 can be dispensed with.
  • EDA is advantageously not used as salt but in the form of the free base as starting material.
  • the proportion of salts in the reaction solution is lower, and consequently less saline by-products or unreacted starting materials are also produced.
  • a high salt content in the reaction solution is particularly disadvantageous if the process according to the invention is carried out in an aqueous phase.
  • the desired product can be readily prepared.
  • it is advantageous that the process according to the invention can be carried out continuously, while this is not possible in processes as described, for example, in US Pat. No. 2006/0041170.
  • a further advantage of the process according to the invention is that, if EDDN or, if appropriate, an aminonitrile mixture comprising EDDN and EDMN is subjected to catalytic hydrogenation following their preparation, ethylene amines such as triethylenetetraamine (TETA), diethylenetriamine (DETA) can be prepared in a simple manner. Although the hydrogenation of nitriles to amines is generally known, TETA can also be prepared by direct hydrogenation of EDDN, but has not been described to date.
  • TETA triethylenetetraamine
  • DETA diethylenetriamine
  • TETA is manufactured on an industrial scale using either the EDC process or the MEOA process.
  • EDC ethylene dichloride
  • DETA ethyleneamine
  • TETA ethylene dichloride
  • DETA ethyleneamine
  • higher ethyleneamines such as TETA or tetraethylenepentaamine (TEPA) can (still) be used in this process described in EP-A 222 934. getting produced.
  • a disadvantage of this process is that a mixture of different ethylene amines is always relatively unselective.
  • TETA can be selectively produced by starting from preferably EDA and FACH with a small number of process steps. If, in one embodiment, an aminonitrile mixture is prepared in one embodiment by appropriate choice of the process parameters, which also contains EDMN in addition to EDDN, besides TETA, DETA can also be obtained as another main reaction product in the catalytic hydrogenation. In addition to TETA, DETA represents another important ethylene amine of great economic interest.
  • EDDN is produced in the process according to the invention by reacting ethylenediamine (EDA) with formaldehyde and hydrocyanic acid (HCN), the molar ratio of EDA to formaldehyde to HCN being 1: 1, 5: 1, 5 to 1 :
  • Option a) - is used without excess to the amino groups of the starting materials, an improvement in selectivity can be achieved in the optionally subsequently carried out hydrogenation.
  • EDDN is preferably prepared according to one of the following options a) to d).
  • EDDN is prepared according to option a).
  • EDA and FACH can in principle be prepared by methods known to those skilled in the art.
  • EDA is used in the process according to the invention in the form of its free base; however, it is also possible to use salts such as the dihydrochloride of EDA as starting material.
  • the preparation of FACH can be carried out by reacting aqueous formaldehyde with hydrocyanic acid.
  • formaldehyde is present as a 30 to 50% aqueous solution
  • hydrocyanic acid is preferably used in 90 to 100% purity.
  • This reaction is preferably carried out at a pH of 5.5, which is preferably adjusted with sodium hydroxide or ammonia.
  • the reaction can be carried out at temperatures of 20 to 70 0 C, for example in the loop and / or tubular reactor.
  • HCN hydrocyanic acid
  • HCN crude gas can be chemisobiert in aqueous formaldehyde solution under the above conditions to FACH.
  • the crude HCN gas is preferably prepared by pyrolysis of formamide and contains, in addition to water, in particular small amounts of ammonia.
  • the obtained aqueous FACH solution can be concentrated by careful vacuum evaporation, for example with a falling-film or thin-film evaporator.
  • a concentration is carried out on a 50-80% FACH solution.
  • stabilization of the FACH solution by lowering the pH to ⁇ 4, preferably to ⁇ 3, is advantageous, for example by addition of acid, for example by addition of phosphoric acid or preferably of sulfuric acid.
  • the molar ratio of EDA to FACH is preferably about 1: 1, 8 to 1: 2 [mol / mol], in particular about 1: 2 [mol / mol].
  • EDDN is reacted by reacting an ethylenediamine-formaldehyde adduct (EDFA) with hydrocyanic acid (HCN), the molar ratio of EDFA to HCN being 1: 1.5 to 1: 2 [mol / mol].
  • EDFA is preferably prepared by mixing approximately equimolar amounts of EDA and formaldehyde.
  • EDA is reacted with a mixture of formaldehyde and hydrocyanic acid (GFB), wherein the molar ratio of EDA to GFB 1: 1, 5 to 1: 2 [mol / mol].
  • the molar ratio of EDA to GFB is 1: 1, 8 to 1: 2 [mol / mol].
  • the GFB is prepared by mixing approximately equimolar amounts of formaldehyde and hydrocyanic acid.
  • EDA is reacted with formaldehyde and hydrogen cyanide (HCN) simultaneously (in parallel), the molar ratio of EDA to formaldehyde to HCN being 1: 1, 5: 1, 5 to 1: 2: 2 [mol / mol / mol ] is.
  • the molar ratio of EDA to formaldehyde to HCN is preferably 1: 1, 8: 1, 8 to 1: 2: 2 [mol / mol / mol].
  • the three reactant components are added to the reaction vessel at the same time or stepwise in equal molar portions, based on the total amount of starting material.
  • the respective reactant components can be added in any desired order to the reaction vessel.
  • one reactant can be completely charged and a second reactant can be added.
  • the respective starting materials can be used directly after their preparation in the process according to the invention.
  • FACH can be used as starting material without prior isolation in the process according to the invention.
  • FACH can first be isolated following its preparation to be subsequently used in the process of the invention.
  • the method of producing EDND is performed substantially free of cyanogen salts, such as KCN.
  • the process according to the invention is normally carried out in the presence of a solvent.
  • a solvent Preferably, in the process according to the invention for the preparation of EDDN, the starting materials are reacted in the aqueous phase.
  • further solvents which are known to the person skilled in the art and which are miscible with water. Less preferred, however, are alcohols, especially methanol, used as the solvent.
  • the inventive method is preferably carried out at a temperature of 10 to 90 0 C, in particular at 30 to 70 0 C.
  • the reaction can be carried out at atmospheric pressure or optionally also at elevated pressure (overpressure).
  • the process according to the invention is preferably carried out in a tubular reactor or a stirred tank cascade.
  • the process according to the invention can also be carried out as a continuous process, in particular as a large-scale process.
  • an aminonitrile mixture is prepared which, in addition to EDDN, also contains EDMN (as the major product).
  • EDMN ethylenediaminemonoacetonitrile
  • aminonitrile mixtures are prepared containing at least 30% by weight EDDN and at least 5% by weight EDMN.
  • EDDN is normally contained in the aminonitrile mixture at from 30 to 95% by weight, preferably from 50 to 95% by weight, more preferably from 75 to 90% by weight.
  • the aminonitrile mixture normally contains EDMN at 5 to 70% by weight, preferably at 5 to 50% by weight, particularly preferably at 10 to 25% by weight.
  • an increase in the proportion of EDMN in the aminonitrile mixture is achieved in that in the options a) - d) in the specified parameter ranges in each case a lower molar fraction of FACH (option a)), HCN (option b)), GFB (option c )) or formaldehyde and HCN (option d)) is used.
  • a molar ratio of EDA to FACH 1: 1, 5 to 1: 1, 8 [mol / mol] is used to increase the EDMN content.
  • an aminonitrile mixture which contains a lower proportion of EDMN for example ⁇ 10% by weight, in particular 5 to 10% by weight
  • EDA electrospray dilution rate
  • an aqueous solution> 40 wt .-% of FACH or pure FACH is used.
  • the molar ratio of EDA to FACH in this case is preferably 1: 2.
  • the content of EDMN and possibly of further by-products, for example other aminonitriles, is preferably ⁇ 10% by weight, in particular ⁇ 5% by weight, based on EDDN.
  • the product EDDN obtained in the process according to the invention and optionally the further product EDMN can be isolated from the reaction mixture or worked up further by methods known to the person skilled in the art. This relates for example to the separation of the reaction product from unreacted starting material and any solvent present.
  • the reaction mixture can be stripped with nitrogen to remove traces of hydrocyanic acid, which can also occur as a decomposition product of FACH.
  • a low boiler removal and / or ii) a water depletion of the reaction product is preferably carried out.
  • the low boilers are separated from the reaction product.
  • FACH is used for the preparation of EDDN and, if appropriate, EDMN
  • the low boiler removal can take place even before the conversion of FACH with EDA.
  • HCN hydrocyanic acid
  • HCN can also be used as a decomposition of FACH.
  • any existing ammonia can be separated at this point.
  • the separation is carried out by distillation, for example in the form of a thin film evaporation such. A Sambay distillation ("Chemie Ingenieurtechnik, Vol. 27, pp. 257-261).
  • the reaction mixture can also be stripped with nitrogen.
  • Water can either be depleted in whole or in part, preferably together with the low boilers or after the low boiler removal.
  • the depletion of the water takes place as distillation. This can be done in one or more stages in an evaporator or an evaporator cascade, wherein different pressures or temperatures can be set from stage to stage.
  • the water separation can also be carried out in a distillation column. The water separation preferably takes place in vacuo.
  • the remaining aminonitrile or aminonitrile mixture may still contain residues of water and low boilers. A residual water content of at least 10% by weight is preferred.
  • the low-boiling components are then only contained in minor traces.
  • EDDN or the aminonitrile mixture containing EDDN and EDMN as main components is subsequently processed further.
  • the resulting EDDN or aminonitrile mixture containing EDDN and EDMN are then subjected to catalytic hydrogenation to obtain at least one ethyleneamine. If necessary, depletion of water contained in the reaction mixture can be carried out before the hydrogenation.
  • the hydrogenation is carried out with the exception of the Wassabreichtation without additional intermediate steps following the preparation of EDDN or the Aminonitrilgemisch containing EDDN and EDMN.
  • the resulting reaction product is subjected to adsorption of impurities, preferably prior to subsequent catalytic hydrogenation.
  • the aminonitrile (mixture) obtained either directly or after completion of low boiler removal or after completion of low boiler and water removal by adsorption of impurities on an adsorbent, e.g. Activated carbon or ion exchanger be cleaned. This can e.g. carried out in an adsorption column filled with the adsorbent.
  • Hydrogenation in the context of the present invention means the reaction of EDDN and optionally EDMN with hydrogen. Hydrogenation processes of, for example, aliphatic nitriles are known in principle to those skilled in the art, but the specific hydrogenation of EDDN or EDMN has not yet been described.
  • This embodiment of the present invention is illustrated in the following Scheme 1, starting from EDA and FACH (option a)) an aminonitrile mixture containing EDDN and EDMN is prepared.
  • TETA triethylenetetraamine
  • DETA diethylenetriamine
  • pip cyclic compounds piperazine
  • AEPip aminoethylene piperazine
  • the catalytic hydrogenation of EDDN to TETA or EDMN to DETA is the subject of another European patent application, which was filed by the same applicant at the same time as the present invention.
  • the exact hydrogenation conditions can be found in the expert of this further application.
  • the hydrogenation is preferably carried out in the presence of a Raney catalyst, in particular a Raney nickel or Raney cobalt catalyst.
  • the hydrogenation is carried out in the presence of a solvent, which is preferably water and / or an organic solvent, in particular tetrahydrofuran or methanol.
  • a solvent which is preferably water and / or an organic solvent, in particular tetrahydrofuran or methanol.
  • TETA is prepared from EDDN and optionally DETA from EDMN.
  • TETA and optionally DETA can be isolated from the reaction solution.
  • the hydrogenation is preferably carried out in the presence of an additive, in particular in the presence of EDA or ammonia.
  • Another object of the present invention is thus the use of EDDN produced by the inventive process or an aminonitrile mixture containing EDDN and EDMN for the production of ethylene amines by catalytic hydrogenation, wherein TETA and / or DETA optionally isolated after the hydrogenation from the reaction solution become.
  • TETA and / or DETA optionally isolated after the hydrogenation from the reaction solution become.
  • a 6 l reaction vessel with propeller stirrer is charged with 6000 g (60 mol) of formaldehyde (30%) and the pH is adjusted to 5.5 using sodium hydroxide solution (1 mol / l).
  • 1661 g (61.2 mol) of hydrogen cyanide over a heated U-tube Below the stirrer with the reaction temperature at 30 0 C and the pH is maintained at 5.5 are metered in in gaseous form.
  • the pH is adjusted to 2.5 with sulfuric acid (50%). The appropriate content is determined by Liebig titration.
  • FACH is produced according to the general rule according to variant b).
  • FACH is produced according to the general rule according to variant b).
  • a) The product obtained is hydrogenated in a semi-batch process.
  • 3.25 g of a Cr-doped Raney cobalt catalyst and 15 ml of THF are placed in a 270 ml autoclave.
  • the autoclave is heated to 120 0 C and hydrogen is pressed up to a total pressure of 100 bar.
  • a mixture of 13.8 g of the crude EDDN solution, 13.8 g of an internal standard and 10 g of water in 106 g of THF is added.
  • the reaction mixture is stirred for an additional 60 minutes under reaction conditions.
  • the output is homogenized by means of methanol.
  • the selectivity is 10% AEPip and 69% TETA.
  • 13% of C4 products (Pip and DETA) are obtained.
  • Example 2a For the sake of comparability, more water is added compared to Example 2a.
  • the excess EDA in the EDDN synthesis forms EDMN, which is hydrogenated to the C4 products DETA and Pip.
  • Example 3a In comparison with Example 3a, an additional addition of water is dispensed with, which has a positive effect on TETA.
  • FACH is produced according to the general rule according to variant b).
  • Ethylenediaminediacetonitrile 132 g (2.2 mol) of EDA are placed in a 2 l reaction vessel and 340.8 g (4 mol) of FACH (67%) are added dropwise with ice cooling at a maximum temperature of 50 ° C. over 35 minutes. After stirring for 1 hour, the almost clear solution is filled. According to Liebig titration, the sales volume is 99.2%.
  • the reaction mixture contains 0.07% free hydrogen cyanide (determined by Volhard titration). By titration, an EDDN yield of 87.7% based on used FACH is obtained.
  • EDMN can not be determined by titration. Assuming that EDMN is formed from reacted ethylenediamine, which does not react to EDDN, the overall aminonitrile yield is 93% and thus a yield of EDMN of 5%.
  • Example 4 Example 4:
  • Formaldehyde cyanohydrin FACH is prepared according to the general procedure according to variant b).
  • FACH is produced according to the general rule according to variant b).
  • Ethylenediaminediacetonitrile 132 g (2.2 mol) of EDA are placed in a 2 l reaction vessel and 340.8 g (4 mol) of FACH (67%) are added dropwise with ice cooling at a maximum temperature of 50 ° C. over 35 minutes. After stirring for 1 hour, the almost clear solution is filled. According to Liebig titration, the sales volume is 99.2%.
  • the reaction mixture contains 0.07% free hydrogen cyanide (determined by Volhard titration). By titration, an EDDN yield of 87.7% based on used FACH is obtained.
  • EDMN can not be determined by titration. Assuming that EDMN is formed from reacted ethylenediamine, which does not react to EDDN, the overall aminonitrile yield is 93% and thus a yield of EDMN of 5%.
  • Example 6 Example 6:
  • FACH is produced according to the general rule according to variant b).

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

Abstract

L'invention concerne un procédé de fabrication d'éthylène-diamine-diacétonitrile (EDDN) consistant à faire réagir de l'éthylène-diamine (EDA) avec du formaldéhyde et de l'acide cyanhydrique (HCN), le rapport molaire de EDA sur formaldéhyde sur HCN étant 1 : 1,5 : 1,5 à 1 : 2 : 2 [mol/mol/mol].
PCT/EP2008/052407 2007-03-01 2008-02-28 Procédé de fabrication d'éthylène-diamine-diacétonitrile WO2008104579A1 (fr)

Applications Claiming Priority (2)

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EP07103291 2007-03-01
EP07103291.6 2007-03-01

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Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013030258A1 (fr) 2011-08-31 2013-03-07 Basf Se Procédé pour traiter des produits réactionnels issus de l'hydrogénation de eddn ou edmn
WO2013030023A1 (fr) 2011-08-31 2013-03-07 Basf Se Procédé pour la production d'eddn et/ou d'edmn ainsi que procédé pour la production de deta et/ou de teta
WO2013030249A1 (fr) 2011-08-31 2013-03-07 Basf Se Procédé pour produire des amines par hydratation de nitriles
WO2013030144A1 (fr) 2011-08-31 2013-03-07 Basf Se Procédé pour produire de l'eddn, de l'edmn, de la teta et de la deta
WO2013030161A1 (fr) 2011-08-31 2013-03-07 Basf Se Procédé pour produire eddn et/ou edmn par mise en réaction de edfa et/ou de edmfa avec hcn
WO2013030174A1 (fr) 2011-08-31 2013-03-07 Basf Se Procédé de production de edfa et/ou edmfa, et deta et/ou teta
WO2013030143A1 (fr) 2011-08-31 2013-03-07 Basf Se Procédé de production d'eddn et/ou d'edmn
WO2013030287A1 (fr) 2011-08-31 2013-03-07 Basf Se Procédé de préparation de eddn et/ou edmn par réaction de fach et eda
WO2013030172A1 (fr) 2011-08-31 2013-03-07 Basf Se Procédé de régénération de catalyseurs de raney
WO2013030255A1 (fr) 2011-08-31 2013-03-07 Basf Se Procédé de préparation de eddn et/ou de edmn et procédé de préparation de deta et/ou de teta
WO2013030254A1 (fr) 2011-08-31 2013-03-07 Basf Se Procédé pour produire teta et/ou deta
WO2013030259A1 (fr) 2011-08-31 2013-03-07 Basf Se Procédé de préparation de teta
US8466323B2 (en) 2008-12-19 2013-06-18 Basf Se Process for preparing pure triethanolamine (TEOA)
WO2014131674A2 (fr) 2013-03-01 2014-09-04 Basf Se Composition d'amine
WO2014131620A1 (fr) 2013-02-28 2014-09-04 Basf Se Procédé de production d'éthylène diamine en utilisant de l'acide prussique dépourvu de so2
US8946459B2 (en) 2011-08-31 2015-02-03 Basf Se Process for preparing EDDN and/or EDMN by reacting EDFA and/or EDMFA with HCN
US8952156B2 (en) 2011-08-31 2015-02-10 Basf Se Process for working up reaction outputs from the hydrogenation of EDDN or EDMN
US9012638B2 (en) 2011-08-31 2015-04-21 Basf Se Process for preparing EDDN and/or EDMN by conversion of FACH and EDA
US9096497B2 (en) 2011-08-31 2015-08-04 Basf Se Process for preparing EDDN and EDMN
US9828329B2 (en) 2014-03-13 2017-11-28 Basf Se Method for the distillative purification of EDA

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE638071C (de) * 1935-04-05 1936-11-09 I G Farbenindustrie Akt Ges Verfahren zur Herstellung von Polyaminocarbonsaeurenitrilen, den entsprechenden Saeuren oder deren Abkoemmlingen
DE1064952B (de) * 1957-06-12 1959-09-10 Bergwerksgesellschaft Hibernia Verfahren und Vorrichtung zur Herstellung von Amino-carbonsaeurenitrilen
JPS5459228A (en) * 1977-10-17 1979-05-12 Showa Denko Kk Preparation of ethylenediamine diacetonitrile
EP0085277A1 (fr) * 1981-12-21 1983-08-10 Ciba-Geigy Ag Procédé de préparation d'acide éthylènediaminetétracétique
US20060041170A1 (en) * 2004-07-19 2006-02-23 Marco Jonas Synthesis of triethylenetetramines

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE638071C (de) * 1935-04-05 1936-11-09 I G Farbenindustrie Akt Ges Verfahren zur Herstellung von Polyaminocarbonsaeurenitrilen, den entsprechenden Saeuren oder deren Abkoemmlingen
DE1064952B (de) * 1957-06-12 1959-09-10 Bergwerksgesellschaft Hibernia Verfahren und Vorrichtung zur Herstellung von Amino-carbonsaeurenitrilen
JPS5459228A (en) * 1977-10-17 1979-05-12 Showa Denko Kk Preparation of ethylenediamine diacetonitrile
EP0085277A1 (fr) * 1981-12-21 1983-08-10 Ciba-Geigy Ag Procédé de préparation d'acide éthylènediaminetétracétique
US20060041170A1 (en) * 2004-07-19 2006-02-23 Marco Jonas Synthesis of triethylenetetramines

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHEMISCHE BERICHTE , 90, 2944-9 CODEN: CHBEAM; ISSN: 0009-2940, 1957 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; BAGANZ, HORST ET AL: "Preparation of N,N'-ethylenebisamino acid derivatives", XP002478217, retrieved from STN Database accession no. 1958:87851 *
DATABASE WPI Week 197925, Derwent World Patents Index; AN 1979-46463B, XP002478238 *

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE45240E1 (en) 2008-12-19 2014-11-11 Basf Se Process for preparing pure triethanolamine (TEOA)
US8466323B2 (en) 2008-12-19 2013-06-18 Basf Se Process for preparing pure triethanolamine (TEOA)
WO2013030161A1 (fr) 2011-08-31 2013-03-07 Basf Se Procédé pour produire eddn et/ou edmn par mise en réaction de edfa et/ou de edmfa avec hcn
WO2013030258A1 (fr) 2011-08-31 2013-03-07 Basf Se Procédé pour traiter des produits réactionnels issus de l'hydrogénation de eddn ou edmn
WO2013030249A1 (fr) 2011-08-31 2013-03-07 Basf Se Procédé pour produire des amines par hydratation de nitriles
WO2013030174A1 (fr) 2011-08-31 2013-03-07 Basf Se Procédé de production de edfa et/ou edmfa, et deta et/ou teta
WO2013030143A1 (fr) 2011-08-31 2013-03-07 Basf Se Procédé de production d'eddn et/ou d'edmn
CN103764617A (zh) * 2011-08-31 2014-04-30 巴斯夫欧洲公司 通过使edfa和/或edmfa与hcn反应制备eddn和/或edmn的方法
WO2013030172A1 (fr) 2011-08-31 2013-03-07 Basf Se Procédé de régénération de catalyseurs de raney
WO2013030255A1 (fr) 2011-08-31 2013-03-07 Basf Se Procédé de préparation de eddn et/ou de edmn et procédé de préparation de deta et/ou de teta
WO2013030254A1 (fr) 2011-08-31 2013-03-07 Basf Se Procédé pour produire teta et/ou deta
WO2013030287A1 (fr) 2011-08-31 2013-03-07 Basf Se Procédé de préparation de eddn et/ou edmn par réaction de fach et eda
CN103764614A (zh) * 2011-08-31 2014-04-30 巴斯夫欧洲公司 Eddn或edmn氢化反应出料的后处理方法
WO2013030023A1 (fr) 2011-08-31 2013-03-07 Basf Se Procédé pour la production d'eddn et/ou d'edmn ainsi que procédé pour la production de deta et/ou de teta
WO2013030259A1 (fr) 2011-08-31 2013-03-07 Basf Se Procédé de préparation de teta
US9096497B2 (en) 2011-08-31 2015-08-04 Basf Se Process for preparing EDDN and EDMN
US9012638B2 (en) 2011-08-31 2015-04-21 Basf Se Process for preparing EDDN and/or EDMN by conversion of FACH and EDA
US8952156B2 (en) 2011-08-31 2015-02-10 Basf Se Process for working up reaction outputs from the hydrogenation of EDDN or EDMN
WO2013030144A1 (fr) 2011-08-31 2013-03-07 Basf Se Procédé pour produire de l'eddn, de l'edmn, de la teta et de la deta
US8946459B2 (en) 2011-08-31 2015-02-03 Basf Se Process for preparing EDDN and/or EDMN by reacting EDFA and/or EDMFA with HCN
WO2014131620A1 (fr) 2013-02-28 2014-09-04 Basf Se Procédé de production d'éthylène diamine en utilisant de l'acide prussique dépourvu de so2
US9914693B2 (en) 2013-02-28 2018-03-13 Basf Se Process for preparing EDA using SO2-free hydrocyanic acid
WO2014131674A3 (fr) * 2013-03-01 2014-10-23 Basf Se Composition d'amine
WO2014131674A2 (fr) 2013-03-01 2014-09-04 Basf Se Composition d'amine
US9828329B2 (en) 2014-03-13 2017-11-28 Basf Se Method for the distillative purification of EDA

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