164462-16-2

Basic information

• Product Name: N,N-BIS(CARBOXYLATOMETHYL)ALANINE TRISODIUM SALT
• Synonyms: N,N-BIS(CARBOXYLATOMETHYL)ALANINE TRISODIUM SALT;N-(1-CARBOXYLATOETHYL)IMINODIACETIC ACID TRISODIUM SALT;TRISODIUM 2-METHYLNITRILOTRIACETATE;TRISODIUM N-(1-CARBOXYLATOETHYL)IMINODIACETATE;TRISODIUM DICARBOXYMETHYL ALANINATE;Alanine, N,N-bis(carboxymethyl)-, trisodium salt;N,N-Bis(carboxymethyl)-DL-alanine, trisodium salt;DL-Alanine-N,N-diacetic acid trisodium salt
• CAS NO: 164462-16-2
• Molecular Formula: C₇H₈NO₆*3Na
• Molecular Weight: 271.11
• Mol File: 164462-16-2.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 479.9ºC at 760 mmHg
• Flash Point: 244.1ºC
• Appearance: /
• Density: 1.464[at 20℃]
• Vapor Pressure: 1.57E-10mmHg at 25°C
• Solubility: Soluble in water
• PKA: 10.6[at 20 ℃]
• Water Solubility: 500g/L at 24℃
• CAS DataBase Reference: N,N-BIS(CARBOXYLATOMETHYL)ALANINE TRISODIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-BIS(CARBOXYLATOMETHYL)ALANINE TRISODIUM SALT(164462-16-2)
• EPA Substance Registry System: N,N-BIS(CARBOXYLATOMETHYL)ALANINE TRISODIUM SALT(164462-16-2)

Safety Data

• Hazardous Substances Data: 164462-16-2(Hazardous Substances Data)

Usage

Application

Green chelating agent MGDA.Na3 as chelating agent, is applicable to a variety of fields. Meanwhile, it has excellent toxicological safety property and stable biodegradability. As a metal ion chelating agent, MGDA.Na3 can chelate metal ions to form stable soluble complexes. MGDA.Na3 can be used in wide pH scope, and create synergistic effect with boicides in the system. MGDA.Na3 can work as substitute for salts of phosphonates, NTA, EDTA, citrate and the other chelating agents in detergent. MGDA(Na3) is a stablizer for sodium perborate and sodium percarbonate and effective builder in non-phosphor detergent formulation. MGDA.Na3 was proofed as high-efficiency bleaching and stubborn strains removing ability in commercial non-phosphor dishwashing formulations. MGDA(Na3) has wonderful clean ability in high efficiency washing powder, washing liquid and soap detergent, e.g. after adding MGDA.Na3 into various soaps, it has the effect to prevent rancidity, color change and dirt precipitation. MGDA(Na3) is used as scale remover and scale inhibitor to prevent scale formulation and soften water, which can also resolve metal salts and hydroxide to clean indissolvable salt scales in various industries.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C7H11NO6.3Na/c1-4(7(13)14)8(2-5(9)10)3-6(11)12;;;/h4H,2-3H2,1H3,(H,9,10)(H,11,12)(H,13,14);;;/q;3*+1/p-3

Synthetic route

L-alanin (56-41-7) + chloroacetic acid (79-11-8) → N,N-bis(carboxymethyl)-DL-alanine trisodium salt (164462-16-2)

Conditions	Yield
With sodium hydroxide In water at 87 - 90℃; for 1.5h; pH=10 - 10.5; Temperature; pH-value; Large scale;	99.75%

formic acid (64-18-6) + L-alanin (56-41-7) + Glyoxilic acid (298-12-4) → N,N-bis(carboxymethyl)-DL-alanine trisodium salt (164462-16-2)

Conditions	Yield
Stage #1: formic acid; L-alanin In water at 23 - 27℃; for 0.666667h; Stage #2: Glyoxilic acid In water at 78 - 82℃; for 5h; Stage #3: With sodium hydroxide In water at 50℃; for 0.5h; pH=11; Temperature; pH-value;	97%

DL-alanine sodium salt (23338-69-4) + chloroacetic acid (79-11-8) → N,N-bis(carboxymethyl)-DL-alanine trisodium salt (164462-16-2)

Conditions	Yield
With sodium hydroxide In water at 82 - 98℃; for 5.01h;	96.63%

chloroacetic acid (79-11-8) + rac-Ala-OH (302-72-7) → N,N-bis(carboxymethyl)-DL-alanine trisodium salt (164462-16-2)

Conditions	Yield
Stage #1: rac-Ala-OH With sodium carbonate; sodium iodide In water at 55℃; for 1.08333h; pH=9.5 - 9.9; Large scale; Stage #2: chloroacetic acid In water at 45 - 92℃; Reagent/catalyst; Large scale;	96%

oxirane (75-21-8) + rac-Ala-OH (302-72-7) → N,N-bis(carboxymethyl)-DL-alanine trisodium salt (164462-16-2) + N-(1-Carboxyethyl)glycine disodium salt

Conditions	Yield
Stage #1: oxirane; rac-Ala-OH With sodium hydroxide In water at 40 - 45℃; under 15001.5 Torr; for 15.5h; Autoclave; Inert atmosphere; Stage #2: With sodium hydroxide; Cu-doped zirconium dioxide In water at 170 - 190℃; under 3750.38 - 7500.75 Torr; for 16.25h; Product distribution / selectivity; Autoclave; Inert atmosphere;	A 90% B 5.2%

methylglycinenitrile-N,N-diacetonitrile (185257-07-2) → N,N-bis(carboxymethyl)-DL-alanine trisodium salt (164462-16-2)

Conditions	Yield
With sodium hydroxide; water at 25 - 95℃; for 10 - 12.25h; Product distribution / selectivity;	85%

N,N-bis(carboxymethyl)-DL-alanine trisodium salt (164462-16-2) → N,N-bis(phosphonomethyl)-1-aminoethylphosphonic acid (45203-32-5)

Conditions	Yield
With phosphorus(III) oxide; methanesulfonic acid at 35℃; for 16h; Concentration; Time; Temperature;	55.6 %Spectr.

N,N-bis(carboxymethyl)-DL-alanine trisodium salt (164462-16-2) → α-alanine-N-diacetic acid (22149-55-9)

Conditions	Yield
With methanesulfonic acid In water at 22℃; pH=2 - 10;

4-amino-2-methylquinoline (6628-04-2) + bis(acetylacetonate)oxovanadium (3153-26-2) + N,N-bis(carboxymethyl)-DL-alanine trisodium salt (164462-16-2) + water (7732-18-5) → [4-amino-2-methylquinolinium][VO(2-methylnitrilotriacetate)(H2O)]2H2O

Conditions	Yield
Stage #1: bis(acetylacetonate)oxovanadium; N,N-bis(carboxymethyl)-DL-alanine trisodium salt; water at 70℃; Stage #2: 4-amino-2-methylquinoline In ethanol

Upstream product

• 79-11-8 chloroacetic acid 
• 302-72-7 rac-Ala-OH 
• 64-18-6 formic acid 
• 56-41-7 L-alanin 
• 298-12-4 Glyoxilic acid 
• 23338-69-4 DL-alanine sodium salt 
• 75-21-8 oxirane 
• 50-00-0 formaldehyd 
• 74-90-8 hydrogen cyanide 
• 64033-02-9 C₇H₁₄NO₄^(1-)*Na⁽¹⁺⁾ 
• 185257-07-2 methylglycinenitrile-N,N-diacetonitrile 

Relevant articles and documents

PROCESS FOR MANUFACTURE OF A COMPLEXING AGENT

A process for making a complexing agent with an enantiomeric excess of at least 60%, wherein said process comprises the following steps: (a) reacting an aqueous slurry of alanine with an enantiomeric excess of at least 60% with formaldehyde and hydrocyanic acid, thereby forming an aqueous solution of alanine- bisacetonitrile, (b) saponifying the alanine-bisacetonitrile from step (a) by combining the aqueous solution obtained in step (a) with an aqueous solution of alkali metal hydroxide.

Preparation method of green chelating agent trisodium N,N-bis(carboxymethyl)alanine

The invention provides a preparation method of a green chelating agent trisodium N,N-bis(carboxymethyl)alanine. The method specifically comprises the steps as follows: partially or completely neutralized L-alanine and chloroacetic acid are subjected to an SN2 bimolecular nucleophilic substitution under an alkaline condition that the pH value is 10-12 in a water solution reaction system to producetrisodium methyl glutamate diacetate. In the reaction process, water in the reaction system is timely removed out at constant speed under the negative pressure of 0-minus 0.005 MPa, so that reaction substrates always keep higher reaction activity. The method is short in reaction cycle and simple in production process, and the production process is simple, and the product yield can reach 99%; chloroacetic acid replaces highly toxic substances such as hydrocyanic acid and the like, thus, the method is safe and environmentally friendly; produced water can be recycled to be used for reaction synthesis and product dilution, no toxic byproducts or wastewater is produced, the cost is low, and large-scale industrial production is facilitated.

Amino acid type chelating agent as well as large-scale preparation method and application thereof

The invention provides degradable amino acid type chelating agent composition suitable for large-scale industrial production and a preparation method of the degradable amino acid type chelating agentcomposition. Amino acid, haloacetic acid and alkali in an aqueous solution are subjected to a reaction at reaction temperature of 40-120 DEG C in a regulated pH range of 8-13 under the action of an iodide catalyst, and after the reaction, the amino acid type chelating agent composition is obtained. The method has the characteristics of being safe, efficient and free of amplification effect, containing fewer impurities and facilitating realization of large-scale production; the raw materials are easily available, and reaction yield is high; an obtained product has better application performance. The invention further provides an application of the composition as a chelating agent in the fields of daily chemicals, food, agriculture, forestry, papermaking, textile, printing and dyeing, watertreatment, coal and the like.