23911-25-3

Basic information

• Product Name: ETHYLENEDIAMINETETRAACETIC DIANHYDRIDE
• Synonyms: AURORA KA-3150;ETHYLENEDIAMINETETRAACETIC DIANHYDRIDE;EDTA DIANHYDRIDE;4,4'-ETHYLENEBIS(2,6-MORPHOLINEDIONE);ETHYLENEDIAMINETETRAACETIC DIANHYDRIDE 98+%;4,4μ-Ethylenebis(2,6-morpholinedione), EDTA dianhydride;Ethylenediaminetetraacetic dianhydride,4,4′-Ethylenebis(2,6-morpholinedione), EDTA dianhydride;1,2-Bis[2,6-dioxo-4-morpholinyl]ethane
• CAS NO: 23911-25-3
• Molecular Formula: C₁₀H₁₂N₂O₆
• Molecular Weight: 256.21
• Product Categories: Analytical Chemistry;Chelating Reagents;Complexones;EDTA Analogs;Ligands for Pharmaceutical Research;Magnetic Resonance Imaging (Chelating Reagents)
• Mol File: 23911-25-3.mol
• Article Data: 19

Chemical Properties

• Melting Point: 190 °C (dec.)(lit.)
• Boiling Point: 489.5°Cat760mmHg
• Flash Point: 249.8°C
• Appearance: /
• Density: 1.449
• Vapor Pressure: 9.93E-10mmHg at 25°C
• Refractive Index: 1.535
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO, Methanol
• PKA: 2.06±0.20(Predicted)
• CAS DataBase Reference: ETHYLENEDIAMINETETRAACETIC DIANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYLENEDIAMINETETRAACETIC DIANHYDRIDE(23911-25-3)
• EPA Substance Registry System: ETHYLENEDIAMINETETRAACETIC DIANHYDRIDE(23911-25-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 23911-25-3(Hazardous Substances Data)

Usage

Uses

Ethylenediaminetetraacetic Acid Dianhydride (A-EDTA) is used as a reagent in the synthesis of a new class of polymer, poly-2.6-piperazinedione. A-EDTA is also used in the synthesis of EDTA functionalized polyacrylnitriles (PANs) by direct reaction with amine and hydroxyl functionalized polyacrylnitrile.

General Description

Ethylenediaminetetraacetic dianhydride (EDTAD) is a ramification of ethylenediaminetetraacetate (EDTA), which consists of two anhydride groups that can react with the hydroxyl and the amino groups. It is a biodegradable compound that is used as a chelating agent.

InChI:InChI=1/C10H12N2O6/c13-7-3-11(4-8(14)17-7)1-2-12-5-9(15)18-10(16)6-12/h1-6H2

Upstream product

• 60-00-4 ethylenediaminetetraacetic acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 81329-81-9 EDTA monoanhydride 
• 2096-83-5 tetraphenyldiphosphine oxide 
• 919529-21-8 2-{{[N-({4-[2-(N-{(2S)-2-[(tert-butoxy)carbonylamino]-3-(phenylmethylthio)propanoylamino}carbamoyl)ethyl]phenyl}methyl)carbamoyl]methyl}[2-({[N-({4-[2-(N-{(2S)-2-[(tert-butoxy)carbonylamino]-3-(phenylmethylthio)-propanoylamino}carbamoyl)ethyl]phenyl}methyl)carbamoyl]methyl}(carboxymethyl)amino)ethyl]amino}acetic acid 
• 1072434-36-6 dithymol-EDTA 
• 1072434-37-7 dicarvacrol-EDTA 
• 1072434-38-8 dieugenol-EDTA 

Relevant articles and documents

A preliminary assay of the potential of soy protein isolate and its hydrolysates to provide interfiber bonding enhancements in lignocellulosic furnishes

Soy protein isolate (SPI) was extracted from soy flour and hydrolyzed with hydrochloric acid, sodium hydroxide, and enzyme, separately, to provide a series of hydrolysates. The SPI and its hydrolysis products were later cross-linked with ethylendiaminetetraacetic acid (EDTA) in the presence of sodium hypophosphite (SPH) after which they were complexed to chitosan as part of an on-going general chemical strategy in our laboratories to improve their incorporation into old corrugated container (OCC) matrix and thus increase inter-fiber bonding. Approximately 2% SPI-EDTA-chitosan and hydrolyzed SPI-EDTA-chitosan additives by mass (OCC-based slurry) were thoroughly mixed before generating a sheet for physical testing. The tensile and burst indices of the SPI-EDTA-chitosan additive-treated OCC pulp sheet increased 46.3% and 61.85%, respectively, while the inter fiber bonding of SPI-EDTA-chitosan additive-treated OCC pulp sheet increased 74.86% compared to the control, albeit having a decreased tear strength and roughness, with significantly increased gloss. The additive-treated pulp sheet was characterized by thermogravimetric analysis (TGA), dynamic mechanical analysis (DMA), and ATR to provide evidence for product synthesis.

90. Synthesis of Vitamin B12 Derivatives with a Peripheral Metal Binding Site

The synthesis and structural characterization of the vitamin B12 derivatives 9 and 10 equipped with a peripheral EDTA (ethylenediaminetetraacetic acid) binding site is described. It is based on the condensation of an activated ester of cobester-c-acid with ethane-1,2-diamine or 2-aminoethanol followed by acylation of the resulting amines with the monoanhydride 8 of EDTA. The title compounds 9 and 10 can be used as modifiers for metal oxide semiconductor electrodes and are potential precursors for the synthesis of bimetallic, supramolecular catalysts.

New compounds: fatty acid and long chain hydrocarbon derivatives containing a strong chelating agent

Fatty acid and long chain hydrocarbon analogs that contain a strong chelating group were synthesized as part of an effort to determine if the biological function of the fatty acid can be used to transport metallic isotopes to the myocardium.

Luminescent and magnetic materials with a high content of Eu3+-EDTA complexes

Bifunctional optical magnetic materials with a high europium content have been prepared. Chelating groups were introduced on the Fe3O4 surface with organosilanes containing ethylenediaminetetraacetic acid (EDTA) derivatives, which were previously prepared via a reaction between EDTA-dianhydride and aminoalkoxysilane agents: 3-(trimethoxysilyl)propylamine (1N), N-[3(trimethoxysilyl)propyl]ethylenediamine (2N) and N1-(3-trimethoxysilylpropyl)diethylenetriamine) (3N). The first coordination sphere of Ln-EDTA complexes present on the modified surfaces of Fe3O4 particles was completed by addition of β-diketonate ligands (tta: thenoyltrifluoroacetone, dbm: dibenzoylmethane, bzac: benzoylacetone and acac: acetylacetone) in order to improve their luminescence properties. The materials were characterized by powder X-ray diffraction (XRD), vibrating sample magnetometry (VSM), scanning electron microscopy (SEM), transmission electron microscopy (TEM), thermogravimetric analysis (TGA), and wavelength dispersive X-ray fluorescence (WDXRF) and Fourier-transform infrared (FT-IR) spectroscopy as well as by zeta potential measurements and luminescence spectroscopy. The hybrid materials exhibited intense red emission, which can be assigned to the 4f-4f transitions of the Eu3+ ion, indicating an efficient intramolecular ligand-to-metal energy transfer. The experimental intensity parameters (Ω2 and Ω4), lifetimes (τ), as well as radiative (Arad) and non-radiative (Anrad) decay rates of the Eu3+ ion were determined and discussed. The strategies used to obtain these materials may contribute to the development of several bifunctional systems for practical applications.

Anti-degradation gelatin films crosslinked by active ester based on cellulose

Functionalization of microcrystalline cellulose (MCC) with EDTA dianhydride (EDTAD) was first achieved using an esterification reaction. N-Hydroxysuccinimide-activated MCC-EDTAD ester (MEN), a novel macromolecule crosslinker based on MCC, was synthesized for the modification of gelatin films. The reaction between gelatin and MEN was verified by the residual free amino test, FTIR and XRD spectra. The introduction of MEN into gelatin decreased the film degradation ratio and increased its thermal stability, flexibility, hydrophobicity, light barrier performance and water uptake ability. Additionally, SEM images proved the successful surface grafting reaction and degradation phenomenon. This unique gelatin film material with advanced properties broke the limitation of the blending method for modification of gelatin with macromolecules and broadened its application as a novel sustained-release material.

Synthesis method of ethylenediamine tetraacetic dianhydride

The invention discloses a synthesis method of ethylenediamine tetraacetic dianhydride. The method includes: slowly mixing ethylenediamine tetraacetic acid (EDTA), acetic anhydride and a catalyst, performing stirring reflux, and at the end of the reaction, conducting filtering, washing and drying to obtain ethylenediamine tetraacetic dianhydride. The method provided by the invention has mild reaction conditions, the reaction process is safe and reliable, the used organic solvents petroleum ether and ethyl acetate have low boiling point, and small toxic and side effects, are easily purchasable on the market, and are convenient for recycling. The invention overcomes the current technical difficulty of hard industrial production of ethylenediamine tetraacetic dianhydride, and provides a safe and environment-friendly green synthesis method.

19F CEST imaging probes for metal ion detection

For detecting metal ions with 19F chemical exchange saturation transfer magnetic resonance imaging (19F CEST MRI), a class of novel fluorinated chelators with diverse fluorine contents and chelation properties were conveniently synthesized on gram scales. Among them, a DTPA-derived chelator with high sensitivity and selectivity was identified as a novel 19F CEST imaging probe for simultaneously detecting multiple metal ions.