150-39-0

Basic information

• Product Name: Heedta
• Synonyms: N-(2-HYDROXYETHYL)ETHYLENEDIAMINE-N,N,N''-TRIACETIC ACID (HEDTA);Hydroxyethylenediaminetriacetic acid, n-;N-(2-Hydroxyethyl)ethylenediaminetriacetic acid, 98+%;HEDTA, HEEDTA, N-Carboxymethyl-Nμ-(2-hydroxyethyl)-N,Nμ-ethylenediglycine;(2-Hydroxyethyl)ethylenediaminetriacetic acid, trisodium salt;Trisodium hydroxyethyl ethylenediaminetriacetate;2-[Carboxymethyl(2-hydroxyethyl)amino]ethyliminodiacetic acid;N-(2-Hydroxyethyl)ethylenediaminetriacetic acid,99%
• CAS NO: 150-39-0
• Molecular Formula: C₁₀H₁₈N₂O₇
• Molecular Weight: 278.26
• EINECS: 205-759-3
• Product Categories: Analytical Chemistry;Chelating Reagents;Complexones;EDTA Analogs
• Mol File: 150-39-0.mol

Chemical Properties

• Melting Point: 212 °C (dec.)(lit.)
• Boiling Point: 421.08°C (rough estimate)
• Flash Point: 300 °C
• Appearance: White crystalline powder
• Density: 1.3300 (rough estimate)
• Vapor Pressure: 1.72E-15mmHg at 25°C
• Refractive Index: 1.4550 (estimate)
• Storage Temp.: Store at RT.
• Solubility: 3 M NaOH: 0.1 M, clear, colorless
• PKA: pK1:2.39;pK2:5.37;pK3:9.93 (25°C)
• Water Solubility: soluble
• BRN: 1804795
• CAS DataBase Reference: Heedta(CAS DataBase Reference)
• NIST Chemistry Reference: Heedta(150-39-0)
• EPA Substance Registry System: Heedta(150-39-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22-40-20/21/22
• Safety Statements: 26-37/39-36-22
• RTECS: MB9185000
• Hazardous Substances Data: 150-39-0(Hazardous Substances Data)

Usage

Uses

Used in Industrial Applications:
N-(2-Hydroxyethyl)ethylenediaminetriacetic acid is used as a chelating agent for its ability to bind and stabilize metal ions, preventing unwanted reactions and facilitating various processes in the industry.
Used in Water Treatment:
HEDTA is used as a sequestering agent in water treatment to remove metal ions, such as calcium and magnesium, which can cause scaling and corrosion in pipes and equipment.
Used in Agriculture:
In agriculture, N-(2-Hydroxyethyl)ethylenediaminetriacetic acid is used as a micronutrient chelator to improve the availability and uptake of essential metal ions by plants, enhancing their growth and health.
Used in Medical Applications:
HEDTA is employed as a chelating agent in medical applications, particularly for the treatment of heavy metal poisoning, where it helps to bind and remove toxic metal ions from the body.
Used in Analytical Chemistry:
In analytical chemistry, N-(2-Hydroxyethyl)ethylenediaminetriacetic acid is used as a complexing agent for the determination of metal ions through various analytical techniques, such as atomic absorption spectroscopy and inductively coupled plasma-optical emission spectroscopy.
Used in Personal Care Products:
HEDTA is also used in the formulation of personal care products, such as shampoos and conditioners, where it acts as a stabilizing agent and helps to maintain the product's consistency and effectiveness.

Purification Methods

Crystallise HEDTA from warm H2O, after filtering, by addition of 95% EtOH and allowing to cool. The crystals, collected on a sintered-glass funnel, are washed three times with cold absolute EtOH, then again crystallised from H2O. After leaching with cold H2O, the crystals are dried at 100o under vacuum. [Spedding et al. J Am Chem Soc 78 34 1956, Beilstein 4 IV 2449.]

InChI:InChI=1/C10H18N2O7/c13-4-3-11(5-8(14)15)1-2-12(6-9(16)17)7-10(18)19/h13H,1-7H2,(H,14,15)(H,16,17)(H,18,19)/p-1

Synthetic route

formaldehyd (50-00-0) + sodium cyanide (143-33-9) + 2-(2-Aminoethylamino)ethanol (111-41-1) → N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0)

Conditions	Yield
With sodium hydroxide

Fe(3+)*3ClO4(1-)*7H2O=[Fe(ClO4)3]*7H2O + N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) → [Fe(III)(N-hydroxyethyl-ethylenediamine triacetate)(H2O)]

Conditions	Yield
In water a ligand (0.01 mol) was suspended in water; the Fe-contg. compd. (0.01 mol) was added with stirring; acetone was added; the crystals were pptd. overnighnt being placed in a refrigerator; elem. anal.;	89%

N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) + vanadium(III) chloride (7718-98-1) + sodium carbonate (497-19-8) → {N'-(2-hydroxyethyl)ethylenediamine-N,N,N'-triacetato}aquavanadium(III)*2H2O

Conditions	Yield
In water under N2; ligand in H2O neutralized with Na2CO3; anhydrous VCl3 added, soln. stirred for a few minutes; crystals collected, washed with cold water and acetone; elem. anal.;	85%

malachite + N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) → [(N-(2-hydroxyethyl)-N'-carboxymethyl-1,2-ethylenediamine-N,N'-diacetato)copper(II) hydrate] (205673-75-2)

Conditions	Yield
In water byproducts: CO2, CuO; N-(2-hydroxyethyl)-1,2-ethylenediamine-N,N,N'-triacetic acid and Cu2CO3(OH)2 in water heated in a Kitasato-flask (t<50 °C), stirred at reduced pressure to remove CO2, then heated at 60 °C, stirred 30 min, cooled to room temp.; filtered, slow evapn. of solvent in 3-4 wk, crystn., filtered, washed with cold water, air-dried, recrystn. from hot water; elem. anal.;	85%

samarium(III) carbonate + N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) → Sm(3+)*C10H15N2O7(3-)*5H2O=Sm(C10H15N2O7)*5H2O

Conditions	Yield
With water In water in hot soln.; addn. of isopropanol with vigorous shaking then addn. of alcohol, washing (isopropanol), drying in air (24 h);	80%

yttrium(III) carbonate + N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) → Y(3+)*C10H15N2O7(3-)*6H2O=Y(C10H15N2O7)*6H2O

Conditions	Yield
With water In water in hot soln.; addn. of isopropanol with vigorous shaking then addn. of alcohol, washing (isopropanol), drying in air (24 h);	80%

neodymium carbonate + N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) → Nd(3+)*C10H15N2O7(3-)*6H2O=Nd(C10H15N2O7)*6H2O

Conditions	Yield
With water In water in hot soln.; addn. of isopropanol with vigorous shaking then addn. of alcohol, washing (isopropanol), drying in air (24 h);	80%

gadolinium(III) carbonate + N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) → Gd(3+)*C10H15N2O7(3-)*6H2O=Gd(C10H15N2O7)*6H2O

Conditions	Yield
With water In water in hot soln.; addn. of isopropanol with vigorous shaking then addn. of alcohol, washing (isopropanol), drying in air (24 h);	80%

europium(III) carbonate + N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) → Eu(3+)*C10H15N2O7(3-)*5H2O=Eu(C10H15N2O7)*5H2O

Conditions	Yield
With water In water in hot soln.; addn. of isopropanol with vigorous shaking then addn. of alcohol, washing (isopropanol), drying in air (24 h);	80%

thorium(IV) nitrate pentahydrate + N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) + sodium hydroxide (1310-73-2) → Th6(N-(2-hydroxoethyl)ethylenediaminetriacetate)

Conditions	Yield
In water for 48h; pH=8.4;	72.1%

N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) + water (7732-18-5) + dihydrogen peroxide (7722-84-1) + titanium tetrachloride (7550-45-0) → (NH4)[Ti(O2)(N-(2-hydroxyethyl)ethylenediaminetriacetate)]·H2O

Conditions	Yield
With ammonia at 20℃; for 48h; pH=2 - 5;	65.2%

N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) + water (7732-18-5) + titanium tetrachloride (7550-45-0) → [Ti((N-hydroxyethyl)ethylenediaminetriacetate)(H2O)]·2H2O

Conditions	Yield
With ammonia at 20℃; for 72h; pH=3;	55.9%

N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) + 4-Nitrophthalonitrile (31643-49-9) → C18H20N4O7

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 50℃; for 48.25h; Inert atmosphere;	55.45%

dysprosium(III) perchlorate + N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) + water (7732-18-5) + sodium hydroxide (1310-73-2) → {[Dy5(N-(2-hydroxyethyl)ethylenediamine-N,N',N'-triacetate)4(H2O)10][Dy(H2O)7][Na(H2O)5]}(ClO4)7·(H2O)15

Conditions	Yield
at 80℃; for 1h; Reflux;	50%

hafnium(IV) dichloride oxide octahydrate + N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) → HfHEDTA

Conditions	Yield
With hydrogenchloride In water for 3h; pH=5;	45%

N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) → 4-(2-(2-oxomorpholin-4-yl)ethyl)piperazine-2,6-dione

Conditions	Yield
Stage #1: N-(2-hydroxyethyl)ethylenediaminetriacetic acid With formamide at 110℃; under 22.5023 Torr; for 1.5h; Stage #2: at 150 - 160℃; for 5h; Inert atmosphere;	39%

potassium metavanadate + N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) + water (7732-18-5) + dihydrogen peroxide (7722-84-1) → K[VO(O2)(N-[2-(2-oxomorpholine-4-yl)ethyl]iminodiacetato(2-))]

Conditions	Yield
With KOH In ethanol; water ice-cooled aq. KVO3 soln. and H2O2 mixed, organic ligand added whilst stirring, pH adjusted to 3.0 with 2 M KOH, ethanol added dropwise, crystals formed in 2 weeks; washed with cooled ethanol, dried over silica gel at 5°C, elem. anal.;	31.5%

N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) + 1,2-diamino-benzene (95-54-5) → N-(2-Hydroxyethyl)-N,N',N'-tris(2-benzylimidazolylmethyl)-1,2-diaminoethane tetrahydrochloride (123994-30-9)

Conditions	Yield
With hydrogenchloride 1.) 175 deg C - 190 deg C, 70 min, 2.) 20 deg C, 24 h; Yield given. Multistep reaction;

N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) → N-(2-Hydroxyethyl)-N,N',N'-tris(2-benzylimidazolylmethyl)-1,2-diaminoethane (102651-58-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2.) conc. HCl / 1.) 175 deg C - 190 deg C, 70 min, 2.) 20 deg C, 24 h 2: 41 percent / conc. NH4OH View Scheme

ruthenium(III) chloride trihydrate + N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) → Na{Ru(hedta)(H2O)}*4H2O

Conditions	Yield
With hydrogenchloride In ethanol RuCl3*3H2O reduced by refluxing in hot EtOH and HCl, addn. of N-(2-hydroxyethyl)ethylenediaminetriacetic acid; pretreated with a Zn/Hg reduction step (to reduce Ru(III));

europium(III) carbonate + N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) → europium(III) N-(2-hydroxyethyl)ethylenediaminetriacetate*2H2O (77461-02-0)

Conditions	Yield
In not given heating (30 min); filtration, pptn. (isopropanol), drying in air (24 h);

N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) + vanadyl (20644-97-7) → oxo (N'-(2-hydroxy ethyl) ethylene diamine N,N,N' triacetato) vanadate (IV) (1-) (62560-22-9, 754942-28-4)

Conditions	Yield
In water reaction in an acidic solution;;
In water reaction in an acidic solution;;

N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) + titanium(III) → N-(2-hydroxyethyl)-ethylenediaminetriacetatoaquotitanium(III) (75431-40-2, 732977-43-4)

Conditions	Yield
In further solvent(s) mixt. of excess of soln. of HEDTA in aq. LiCl and soln. of Ti(3+) in aq. LiCl;

dysprosium((III) oxide + N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) → Dy(3+)*C10H15N2O7(3-)*8H2O=Dy(C10H15N2O7)*8H2O

Conditions	Yield
With water In water

erbium(III) oxide + N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) → Er(3+)*C10H15N2O7(3-)*6H2O=Er(C10H15N2O7)*6H2O

Conditions	Yield
With water In water

europium(III) oxide + N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) → Eu(3+)*C10H15N2O7(3-)*7H2O=Eu(C10H15N2O7)*7H2O

Conditions	Yield
With water In water

gadolinium(III) oxide + N-(2-hydroxyethyl)ethylenediaminetriacetic acid (150-39-0) → gadolinium N-(2-hydroxyethyl)ethylenediaminetriacetic acid aquo complex

Conditions	Yield
With water In water

Upstream product

• 50-00-0 formaldehyd 
• 143-33-9 sodium cyanide 
• 111-41-1 2-(2-Aminoethylamino)ethanol 

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