WO1983004020A1 - Procede pour la preparation d'amino-cetonitriles - Google Patents

Procede pour la preparation d'amino-cetonitriles Download PDF

Info

Publication number
WO1983004020A1
WO1983004020A1 PCT/EP1983/000118 EP8300118W WO8304020A1 WO 1983004020 A1 WO1983004020 A1 WO 1983004020A1 EP 8300118 W EP8300118 W EP 8300118W WO 8304020 A1 WO8304020 A1 WO 8304020A1
Authority
WO
WIPO (PCT)
Prior art keywords
acid
catalyst
cooh
preparation
nta
Prior art date
Application number
PCT/EP1983/000118
Other languages
German (de)
English (en)
Inventor
Georg L. Busch
Hans-Peter Meier
Original Assignee
Cemona Ag
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 Cemona Ag filed Critical Cemona Ag
Publication of WO1983004020A1 publication Critical patent/WO1983004020A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles

Definitions

  • the invention relates to a process for the preparation of aminoacetonitriles, in particular nitrilotriacetonitrile (NTAN), iminodiacetonitrile (IDAN), ethylenediamine-tetraacetonitrile (EDTN), diethylenetriamine-pentaacetonitrile (DTPAN) and diethylenetriamine-tetraacetonitrile of the general formula (I)
  • NTAN nitrilotriacetonitrile
  • IDAN iminodiacetonitrile
  • EDTN ethylenediamine-tetraacetonitrile
  • DTPAN diethylenetriamine-pentaacetonitrile
  • I diethylenetriamine-tetraacetonitrile
  • NTA nitrilotriacetic acid
  • IDA iminodiacetic acid
  • EDTA ethylenediaminetetraacetic acid
  • DTPA diethylenetriaminepentaacetic acid
  • nitrilotriacetonitrile is obtained in the highest yields by reacting ammonia with formaldehyde and hydrocyanic acid in the presence of nitrilotriacetic acid as a catalyst.
  • the nitriloacetonitrile obtained contains slightly more than half of those used.
  • Nitrilotriacetic acid. The rest is in the mother liquor. After evaporation and replacement of the nitrilotriacetic acid (NTA) separated off with the nitriloacetonitrile by fresh NTA, this is used again as a catalyst in the subsequent batch, etc.
  • NTA nitrilotriacetic acid
  • ethylenediaminetetraacetonitrile (EDTN) is obtained in yields of 95 to 98% of theory if ethylenediamine, formaldehyde and hydrocyanic acid are reacted in the presence of about 3 mol% of ethylenediaminetetraacetic acid (EDTA).
  • EDTA ethylenediaminetetraacetic acid
  • the mother liquor can be reused after evaporating and supplementing the EDTA separated with the EDTN. The reuse can be repeated a few times.
  • the process for the preparation of aminoacetonitriles of the general formula (I) by reacting ammonia, ethylenediamine or diethylenetriamine with formaldehyde and hydrocyanic acid is accordingly characterized in that the catalyst comprises the aminoacetic acid of the formula I belonging to the acetonitrile of the formula I to be prepared (II)
  • NTAN nitrilotriacetic acid
  • EDTA ethylene diamine tetraacetic acid
  • DTPAN diethylenetriaminepentaacetonitrile
  • DTPA diethylenetriaminepentaacetic acid
  • Ammonia is "converted by reaction with formalin in hexamethylene lentetramin.
  • NTA nitrilotriacetic acid
  • the product is filtered off and dried. It contains 510 g nitrilotriacetonitrile "(NTAN), which are 95% of theory, and 8 g of nitrilotriacetic acid (NTA).
  • NTAN nitrilotriacetonitrile
  • the Mut ⁇ terlauge is evaporated, the evaporation residue with 8 g of fresh NTA added and used in subsequent approach with equal success as a catalyst .
  • ethylenediaminetetraacetonitrile forms.
  • the product is filtered off and dried. It consists of 210 g of ethylenediaminetetraacetonitrile (that is 97% of theory) and 7.2 g of ethylenediaminetetraacetic acid.
  • the mother liquor is evaporated.
  • the residue contains 1.6 g of ethylenediaminetetraacetic acid.
  • it is fresher after being mixed with 7.2 g
  • Ethylene diamine tetraacetic acid was used again as a catalyst.
  • the mother liquor is evaporated, 5.6 g of fresh ethylenediaminetetraacetic acid are added, and the approach is used again as a catalyst, etc.
  • the mother liquor After evaporation and the addition of 8.3 g of DTPA, the mother liquor can be used with practically the same success as a catalyst for the subsequent same batch.
  • iminodiacetonitrile which contains small amounts of EDA is obtained by reacting ammonia with a little formalin and hydrocyanic acid in the presence of iminodiacetic acid (IDA). After evaporation and replacement of lost EDA, the mother liquor can be used as a catalyst in the subsequent batch.
  • IDA iminodiacetic acid
  • the mother liquor can be used repeatedly after evaporation and addition of the lost diethylenetriamine tetraacetic acid.

Landscapes

  • 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

Les composés répondant à la formule (I), dans laquelle R signifie: -H, -CH2CN, -CH2CH2-N(CH2CN)2, -CH2CH2-N(CH2CN)-CH2CH2-N(CH2CN)2 ou -CH2CH2-NH-CH2CH2-N(CH2CN)2 sont préparés par réaction d'ammoniac, d'éthylène diamine ou de diéthylènetriamine avec le formaldéhyde et l'acide cyanhydrique. Le procédé est caractérisé en ce qu'on utilise comme catalyseur l'acide aminoacétique également employé pour la préparation de l'acétonitrile de formule I. L'acide aminoacétique répond à la formule (II), dans laquelle R' signifie: -H, -CH2COOH, -CH2CH2N(CH2COOH)2, -CH2CH2-N(CH2COOH)-CH2CH2-N(CH2COOH)2 ou -CH2CH2-NH-CH2CH2-N(CH2COOH)2.
PCT/EP1983/000118 1982-05-18 1983-05-06 Procede pour la preparation d'amino-cetonitriles WO1983004020A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH3077/82-3 1982-05-18
CH307782A CH646140A5 (de) 1982-05-18 1982-05-18 Verfahren zur herstellung von aminoacetonitrilen.

Publications (1)

Publication Number Publication Date
WO1983004020A1 true WO1983004020A1 (fr) 1983-11-24

Family

ID=4248115

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1983/000118 WO1983004020A1 (fr) 1982-05-18 1983-05-06 Procede pour la preparation d'amino-cetonitriles

Country Status (5)

Country Link
EP (1) EP0109406A1 (fr)
CH (1) CH646140A5 (fr)
ES (1) ES522516A0 (fr)
IT (1) IT1163385B (fr)
WO (1) WO1983004020A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104387285A (zh) * 2014-10-27 2015-03-04 石家庄杰克化工有限公司 制备二乙烯三胺五乙酸五钠盐的工艺

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1177646B (de) * 1957-06-12 1964-09-10 Bergwerksgesellschaft Hibernia Verfahren zur Herstellung von Aminocarbonsaeurenitrilen
DE2027972A1 (de) * 1969-08-26 1971-04-15 W R Grace & Cc , New York, N Y (VStA) Verfahren zur Herstellung von eckige Klammer auf ,N Bis(cyanmethyl)glycin eckige Klammer zu
GB1342045A (en) * 1971-01-21 1973-12-25 Monsanto Co Process for producing nitrilotriacetonitrile
FR2350332A2 (fr) * 1976-05-08 1977-12-02 Basf Ag Procede de preparation de nitriles de glycocolles
GB2061271A (en) * 1979-10-20 1981-05-13 Degussa Production of iminodiacetonitrile

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1177646B (de) * 1957-06-12 1964-09-10 Bergwerksgesellschaft Hibernia Verfahren zur Herstellung von Aminocarbonsaeurenitrilen
DE2027972A1 (de) * 1969-08-26 1971-04-15 W R Grace & Cc , New York, N Y (VStA) Verfahren zur Herstellung von eckige Klammer auf ,N Bis(cyanmethyl)glycin eckige Klammer zu
GB1342045A (en) * 1971-01-21 1973-12-25 Monsanto Co Process for producing nitrilotriacetonitrile
FR2350332A2 (fr) * 1976-05-08 1977-12-02 Basf Ag Procede de preparation de nitriles de glycocolles
GB2061271A (en) * 1979-10-20 1981-05-13 Degussa Production of iminodiacetonitrile

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104387285A (zh) * 2014-10-27 2015-03-04 石家庄杰克化工有限公司 制备二乙烯三胺五乙酸五钠盐的工艺

Also Published As

Publication number Publication date
ES8505513A1 (es) 1984-09-16
EP0109406A1 (fr) 1984-05-30
CH646140A5 (de) 1984-11-15
IT1163385B (it) 1987-04-08
ES522516A0 (es) 1984-09-16
IT8321155A1 (it) 1984-11-18
IT8321155A0 (it) 1983-05-18

Similar Documents

Publication Publication Date Title
EP1247800B1 (fr) Utilisation de sels d'acide iminodisuccinique dans la production de papier
EP2262760B1 (fr) Procede de preparation d'acides n,n-diacetiques d'acide aminodicarboxylique
EP1334961A1 (fr) Procédé de préparation de dérivés d'acide N,N-diacétique de glycine
EP0745582A2 (fr) Procédé pour la préparation de dérivés de glycine-N,N-diacétique par réaction de dérivés de la glycine ou de leurs précurseurs avec le formaldéhyde et l'acide cyanhydrique (ou ...) en milieu acide aqueux
DE1543542A1 (de) Chemisches Verfahren
DE2555769A1 (de) Verfahren zur herstellung von n-alkylglycinnitrilen
EP0745581B1 (fr) Procédé pour la préparation de dérivés de glycine-N,N-diacétique par réaction de dérivés de la glycine ou de leurs précurseurs avec le formaldéhyde et du cyanure de métal alcalin dans un milieu acide aqueux
WO1983004020A1 (fr) Procede pour la preparation d'amino-cetonitriles
EP0045386B1 (fr) Méthode de préparation d'aminonitriles
EP1199302B1 (fr) Procédé de cyanoalkylation en continu de composés ayant une ou plusieurs fonctions NH
DE2164393C2 (de) Verfahren zur Herstellung von Lysin oder eines Lysinsalzes
EP0079623B1 (fr) Procédé de préparation d'esters de l'acide 1H-pyrrole-2-acétiques
EP0059259B1 (fr) Procédé de préparation d'acides N-(carboxy-alkyl) amino-1 alcane diphosphoniques-1,1 et leurs sels alcalins
EP0641310B1 (fr) PROCEDE DE FABRICATION D'ACIDE $g(b)-ALANINE-DIACETIQUE OU DE SES SELS DE METAUX ALCALINS OU D'AMMONIUM
DE1126885B (de) Verfahren zur Herstellung aliphatischer Diaminopolycarbonsaeuren
DD292239A5 (de) Verfahren zur herstellung von alkalisalzen der n-alkylsubstituierten aminoalkansaeuren
DE2640616B2 (de) Verfahren zur Herstellung von N-Acyl-2-arylglycinen
DE1965004C3 (de) Verfahren zur Herstellung von N-Acyl-aminocyclohexancarbonsäurenitrilen
DE1493550C3 (de) Verfahren zur Herstellung von Azoverbindungen
AT218019B (de) Verfahren zur Herstellung von α-substituierten Isonikotinsäurethioamiden
DE1222927B (de) Verfahren zur Herstellung von Cyanocarbonsaeureestern
CH504410A (de) Verfahren zur Herstellung von Nitrilotriacetonitril und dessen Verwendung
DD301829A7 (de) Verfahren zur Erhoehung der Ausbeute bei der einstufigen, drucklosen Synthese des Natriumsalzes der Nitrilotriessigsaeure
DE19947332A1 (de) Verfahren zur Herstellung von 3-Alkyl-N-nitro-4H-1,3,5-oxadiazin-3-iminen
CH437248A (de) Verfahren zur Herstellung von Derivaten aliphatischer Dicarbonsäuren

Legal Events

Date Code Title Description
AK Designated states

Designated state(s): JP US

AL Designated countries for regional patents

Designated state(s): AT BE CH DE FR GB LU NL SE