58976-65-1

Basic information

• Product Name: N,N-bis(carboxymethyl)-L-glutamic acid
• Synonyms: N,N-bis(carboxymethyl)-L-glutamic acid;(2S)-2-[Bis(carboxymethyl)amino]pentanedioic acid;N,N-Bis(2-hydroxy-2-oxoethyl)-L-glutamic acid;N,N-Bis[2-hydroxy-2-oxoethyl]-L-glutamic acid;Einecs 261-530-8
• CAS NO: 58976-65-1
• Molecular Formula: C₉H₁₃NO₈
• Molecular Weight: 263.20142
• EINECS: 261-530-8
• Mol File: 58976-65-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 587.1°C at 760 mmHg
• Flash Point: 308.9°C
• Appearance: /
• Density: 1.612g/cm³
• Vapor Pressure: 2.64E-15mmHg at 25°C
• Refractive Index: 1.571
• Water Solubility: 291g/L at 20℃
• CAS DataBase Reference: N,N-bis(carboxymethyl)-L-glutamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-bis(carboxymethyl)-L-glutamic acid(58976-65-1)
• EPA Substance Registry System: N,N-bis(carboxymethyl)-L-glutamic acid(58976-65-1)

Safety Data

• Hazardous Substances Data: 58976-65-1(Hazardous Substances Data)

Usage

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C9H13NO8/c11-6(12)2-1-5(9(17)18)10(3-7(13)14)4-8(15)16/h5H,1-4H2,(H,11,12)(H,13,14)(H,15,16)(H,17,18)

Synthetic route

L-glutamic acid (56-86-0) + bromoacetic acid (79-08-3) → L-glutamic acid N,N-diacetic acid (58976-65-1) + L-N-(carboxymethyl)glutamic acid (41035-85-2)

Conditions	Yield
With water; magnesium oxide

L-glutamic acid (56-86-0) + chloroacetic acid (79-11-8) → L-glutamic acid N,N-diacetic acid (58976-65-1)

Conditions	Yield
With sodium hydroxide

formaldehyd (50-00-0) + hydrogen cyanide (74-90-8) + L-glutamic acid (56-86-0) → glutamic acid monoacetic acid (45084-14-8) + L-glutamic acid N,N-diacetic acid (58976-65-1)

Conditions	Yield
Stage #1: formaldehyd; hydrogen cyanide; L-glutamic acid With sodium hydroxide In water at 90 - 105℃; for 4h; Stage #2: With sulfuric acid In water at 33℃; pH=1.8;

L-glutamic acid N,N-diacetic acid tetra sodium salt → L-glutamic acid N,N-diacetic acid (58976-65-1)

Conditions	Yield
In water at 40℃; Inert atmosphere; Electrochemical reaction;

L-glutamic acid N,N-diacetic acid (58976-65-1) + [(RuCl2(2,2'-bipyridine))2Cl2]*0.5H2O + potassium chloride → K[Ru(2,2'-bipyridine)(N,N-bis(carboxymethyl)-S-glutamic acid)]

Conditions	Yield
With Et3N In ethanol under Ar, metal compd. and ligand (1:2), Et3N added, stirred at 40°C for 12 h; filtered, evapd., dissolved (water), chromd. (QAE Sephadex A-25, 0.1 M aq. KCl), filtered (Sephadex G-10);

Upstream product

• 56-86-0 L-glutamic acid 
• 50-00-0 formaldehyd 
• 74-90-8 hydrogen cyanide 
• 79-11-8 chloroacetic acid 
• 79-08-3 bromoacetic acid 

Downstream Products

• 1416880-75-5 D,L-GLDA-KH₃ 

Relevant articles and documents

CRYSTALLINE PARTICLES OF GLUTAMIC ACID N,N-DIACETIC ACID

The invention relates to glutamic acid N,N-diacetic acid (GLDA) of the formula GLDA-YmHn, wherein m is less than 0.5, n +m = 4, Y is a monovalent cation that is not a proton, in the form of crystals, a process to make these crystals,and their uses, in particular in detergent compositions.

CHELATING AGENT PRECURSORS, FLUIDS CONTAINING THEM, AND THEIR USE

The present invention relates to a chelating agent precursor that contains glutamic acid N,N-diacetic acid (GLDA) and/or methylglycine N,N-diacetic acid (MGDA) wherein at least one of the carboxylic acid groups is presentas a carboxylic acid derivative selected from the group of amides, anhydrides, and esters, combinations thereof, and salts thereof, provided that it is not the triethyl ester of GLDA, the triethyl mono-t-butyl ester of GLDA, the tri-t-butyl ester of GLDA, the monobenzyl tri-t-butyl ester of GLDA, any ester or amide that contains azacycloalkane groups, any amide that contains biotin groups, any amide that contains minoethylcarbamoyl based amide groups, (S)-diethyl 2,2'-(1-benzyloxy)-1,5-dioxo-5-(prop-2-ynylamino)pentan-2-ylazanediyl-diacetate, diethyl 2,2'-(5-(3-azidopropylamino)-1-(benzyloxy)-1,5-dioxo-pentan-2-ylazanediyl-diacetate, the trimethyl ester of MGDA, the monomethyl ester dimethylamide of MGDA, the dibenzyl ester of MGDA, the dibenzyl mono t-butyl ester of MGDA, the di t-butyl ester of MGDA, the di-t-butyl- monobenzyl ester of MGDA, N,N-bis(benzyloxycarbonylmethyl)-N'-methoxycarbonylmethyl-alanine amide, or N,N- bis(tert-butoxycarbonyl)-N'-methoxycarbonylmethyl-alanine amide, and esters of GLDA immobilized on a gel, and that the amide is not the amide of ammonia, to a fluid containing the above chelating precursor and a liquid, and to the use of a chelating agent precursor of MGDA and GLDA and fluids containing them in an application wherein delayed acidity or chelating capacity is useful, such as in descaling, bleaching, cleaning, and treating oil and/or gas-containing subterranean formations.