58976-65-1

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

Downstream Products

• 1416880-75-5 D,L-GLDA-KH₃ 

Relevant academic research and scientific papers

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.

CRYSTALLINE PARTICLES OF SALTS OF GLUTAMIC ACID N,N-DIACETIC ACID

The invention relates to a salt of glutamic acid-N,N-diacetic acid (GLDA) of the formula GLDA-YmHn, wherein m is equal to or more than 0.5 and lower than or equal to 2.5, n +m = 4, and wherein Y is a monovalent cation that is not a proton, comprising L-GLDA-YmHn to D-GLDA-YmHn in a range between 100:0 and 50:50 (L:D), characterized in that the salt is crystalline, a process to make such crystalline salt, and to uses of such salt, such as, 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.

PROCESS TO PREPARE AMINO ACID-N, N-DIACETIC ACID COMPOUNDS

The invention relates to a process for the production of an amino acid having at least one secondary or tertiary amino group and three or more carboxyl groups or its salt with less than an equivalent of alkaline metal based on the number of carboxyl groups, said process comprising reducing alkali metal ions from an aqueous solution of an alkali metal salt of an amino acid having at least one secondary or tertiary amino group and three or more carboxyl groups and acidifying the amino carboxylate starting material by first performing a chemical acidification step using an organic or inorganic acid to get a compound in which at least one of the groups is protonated, and in a subsequent step further acidifying the amino carboxylate starting material and reducing alkali metal ions from an aqueous solution of the partially acidified alkali metal salt of the amino acid having at least one secondary or tertiary amino group and three or more carboxyl groups by electrodialysis, wherein the electrodialysis is performed using a hydrogen ion permselective membrane on the anode side and a cation-permeable membrane on the cathode side.