Product Name

  • Name

    Ethylenebis(nitrilodimethylene)tetraphosphonic acid

  • EINECS 215-851-5
  • CAS No. 1429-50-1
  • Article Data16
  • CAS DataBase
  • Density 1.993 g/cm3
  • Solubility 19.6g/L at 20℃
  • Melting Point 247 °C
  • Formula C6H20N2O12P4
  • Boiling Point 878.7 °C at 760 mmHg
  • Molecular Weight 436.126
  • Flash Point 485.2 °C
  • Transport Information
  • Appearance
  • Safety 26-36/37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 1429-50-1 (Ethylenebis(nitrilodimethylene)tetraphosphonic acid)
  • Hazard Symbols IrritantXi
  • Synonyms Phosphonicacid, [1,2-ethanediylbis[nitrilobis(methylene)]]tetrakis- (9CI);Phosphonicacid, [ethylenebis(nitrilodimethylene)]tetra- (6CI,7CI,8CI);EDPA;EDTMP;EDTPA;Editempa;Ethylenediamine-N,N,N',N'-tetra(methylphosphonic acid);Ethylenediaminetetramethylenephosphonate;N,N,N',N'-Tetrakis(phosphonomethyl)ethylenediamine;[Ethylenebis(nitrilodimethylene)]tetraphosphonic acid;EDTMPS;
  • PSA 275.84000
  • LogP -1.86880

Synthetic route

formaldehyd
50-00-0

formaldehyd

ethylenediamine
107-15-3

ethylenediamine

1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

Conditions
ConditionsYield
Stage #1: ethylenediamine With hydrogenchloride; phosphonic Acid In water for 0.0333333h; Microwave irradiation;
Stage #2: formaldehyd In water for 0.166667h; Irani-Moedritzer reaction; Microwave irradiation;
63%
With hydrogenchloride; phosphonic Acid
With hydrogenchloride; phosphonic Acid In water Heating;
formaldehyd
50-00-0

formaldehyd

ethylenediamine
107-15-3

ethylenediamine

A

1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

B

N-methylethylenediamine-N,N',N'-trimethylenetris(phosphonic acid)

N-methylethylenediamine-N,N',N'-trimethylenetris(phosphonic acid)

Conditions
ConditionsYield
Stage #1: ethylenediamine With phosphorous acid In water at 136℃; Reflux;
Stage #2: formaldehyd In water at 130 - 136℃; for 4.33333h;
A 48.2%
B 28.8%
formaldehyd
50-00-0

formaldehyd

ethylenediamine
107-15-3

ethylenediamine

A

1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

B

<<(2-aminoethyl)imino>bis(methylene)>biphosphonic acid

<<(2-aminoethyl)imino>bis(methylene)>biphosphonic acid

Conditions
ConditionsYield
With hydrogenchloride; phosphoric acid In water at 100℃; for 3h;A 18.8%
B 36.7%
chloromethylphosphonic acid
2565-58-4

chloromethylphosphonic acid

ethylenediamino tris(methylenephosphonic acid)
1898-63-1

ethylenediamino tris(methylenephosphonic acid)

1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

Conditions
ConditionsYield
With sodium hydroxide
ethylenediamine
107-15-3

ethylenediamine

CH3Cl2O2P

CH3Cl2O2P

1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

Conditions
ConditionsYield
(i) aq. NaOH, (ii) /BRN= 605263/; Multistep reaction;
ethylenediamine
107-15-3

ethylenediamine

disodium-salt of/the/ chloromethylphosphonic acid

disodium-salt of/the/ chloromethylphosphonic acid

1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

Conditions
ConditionsYield
With sodium carbonate
formaldehyd
50-00-0

formaldehyd

ethylenediamine
107-15-3

ethylenediamine

A

1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

B

ethylenediamino tris(methylenephosphonic acid)
1898-63-1

ethylenediamino tris(methylenephosphonic acid)

Conditions
ConditionsYield
With phosphorous acid; methanesulfonic acid In water at 105 - 130℃; for 2.5 - 6h; Product distribution / selectivity; Heating / reflux;A 40 - 73.6 %Spectr.
B n/a
With phosphorous acid; methanesulfonic acid; sulfuric acid In water at 105℃; for 6.33333h; Product distribution / selectivity; Heating / reflux;A 75.5 %Spectr.
B n/a
formaldehyd
50-00-0

formaldehyd

ethylenediamine
107-15-3

ethylenediamine

A

1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

B

ethylenediamino tris(methylenephosphonic acid)
1898-63-1

ethylenediamino tris(methylenephosphonic acid)

C

<<(2-aminoethyl)imino>bis(methylene)>biphosphonic acid

<<(2-aminoethyl)imino>bis(methylene)>biphosphonic acid

D

N-methylethylenediamine-N,N',N'-trimethylenetris(phosphonic acid)

N-methylethylenediamine-N,N',N'-trimethylenetris(phosphonic acid)

Conditions
ConditionsYield
With hydrogenchloride; phosphorous acid In water at 110℃; for 3h; Product distribution / selectivity;
ethylenediaminetetraacetic acid
60-00-4

ethylenediaminetetraacetic acid

1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

Conditions
ConditionsYield
With phosphorus(III) oxide; methanesulfonic acid at 45 - 80℃; for 2h;94.5 %Spectr.
N,N,N',N'-tetrakis(hydroxymethyl)ethanediamine
98756-99-1

N,N,N',N'-tetrakis(hydroxymethyl)ethanediamine

1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

Conditions
ConditionsYield
Stage #1: N,N,N',N'-tetrakis(hydroxymethyl)ethanediamine With phosphorus(III) oxide; methanesulfonic acid at 50 - 80℃; for 1h;
Stage #2: With water at 25℃; for 1h; Temperature; Concentration;
aluminum sulfate octadecahydrate

aluminum sulfate octadecahydrate

1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

aluminum ethylenediamine tetra(methylene phosphonate)

aluminum ethylenediamine tetra(methylene phosphonate)

Conditions
ConditionsYield
With sodium hydroxide In water at 90℃; for 1h; Reagent/catalyst; Time; Large scale;97.4%
potassium aquapentachlororuthenate(III)

potassium aquapentachlororuthenate(III)

1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

K3{ruthenium(III)(ethylenediamine-N,N,N',N'-tetramethylphosphonato)*6H2O}

K3{ruthenium(III)(ethylenediamine-N,N,N',N'-tetramethylphosphonato)*6H2O}

Conditions
ConditionsYield
With KOH In water byproducts: RuO2; equimolar quantity of reagents; heated on water-bath for 30 min; filtered; heated for 1-1.5 h; added KOH (pH=5); filtered; evapd.; ground with acetone; filtered off; washed (mixture of methanol and ethanol (2/1)); elem. anal.; TA; UV;90%
potassium aquapentachlororuthenate(III)

potassium aquapentachlororuthenate(III)

1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

K3{ruthenium(III) (ethylenediamine-N,N,N',N'-tetramethylphosphonato)Cl4}*2H2O

K3{ruthenium(III) (ethylenediamine-N,N,N',N'-tetramethylphosphonato)Cl4}*2H2O

Conditions
ConditionsYield
In water byproducts: RuO2; equimolar quantity of reagents; heated on water-bath for 30-40 min; filtered; evapd. on water-bath; ground with acetone; filtered off; washed (acetone); dried in vac. desiccator; elem. anal.; TA; UV;83%
vanadium(IV) chloride

vanadium(IV) chloride

1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

water
7732-18-5

water

C6H16N2O12P4(VO)1.8*4H2O

C6H16N2O12P4(VO)1.8*4H2O

Conditions
ConditionsYield
In water ligand in H2O mixed with AlCl3 in H2O; centrifuged, treated with 0.02 M HCl, stirred in ultrasonic bath for 30 min, standed overnight at room temp., the same treatment repeated 3 times, H2O added, lyohpylized overnight, elem. anal.;78%
1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

water
7732-18-5

water

zinc(II) chloride
7646-85-7

zinc(II) chloride

([Zn2(N,N,N',N'-ethylenediaminetetrakis(methylenephosphonic acid)(-4H))]*2H2O)(n)

([Zn2(N,N,N',N'-ethylenediaminetetrakis(methylenephosphonic acid)(-4H))]*2H2O)(n)

Conditions
ConditionsYield
With LiF; (C2H5)3N In ethanol; water High Pressure; adjusted to pH 5.3 with (C2H5)3N, kept in an autoclave at 160°C for 4 d; elem. anal.;77%
aluminium trichloride
7446-70-0

aluminium trichloride

1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

water
7732-18-5

water

aluminium(III) ethylenediaminetetramethylenephosphonate tetrahydrate

aluminium(III) ethylenediaminetetramethylenephosphonate tetrahydrate

Conditions
ConditionsYield
In water ligand in H2O mixed with AlCl3 in H2O; centrifuged, treated with 0.02 M HCl, stirred in ultrasonic bath for 30 min, standed overnight at room temp., the same treatment repeated 3 times, H2O added, lyohpylized overnight, elem. anal.;76%
cobalt(II) nitrate hexahydrate

cobalt(II) nitrate hexahydrate

2-(1-(pyrazin-2-yl)ethylidene)hydrazine-1-carbothioamide
153736-25-5

2-(1-(pyrazin-2-yl)ethylidene)hydrazine-1-carbothioamide

sodium molybdate dihydrate
7631-95-0

sodium molybdate dihydrate

1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

Mo12O40P(3-)*3C14H16CoN10S2(1+)

Mo12O40P(3-)*3C14H16CoN10S2(1+)

Conditions
ConditionsYield
Stage #1: cobalt(II) nitrate hexahydrate; 1-(1-(pyrazin-2-yl)ethylidene)thiosemicarbazide; sodium molybdate dihydrate; 1,2-ethanediylbistetraphosphonic acid In water; acetonitrile at 20℃; for 2h;
Stage #2: With hydrogenchloride In water; acetonitrile at 130℃; for 72h; pH=2.7 - 3; Autoclave;
52.7%
cobalt(II) nitrate hexahydrate

cobalt(II) nitrate hexahydrate

sodium tungstate (VI) dihydrate
10213-10-2

sodium tungstate (VI) dihydrate

2-(1-(pyrazin-2-yl)ethylidene)hydrazine-1-carbothioamide
153736-25-5

2-(1-(pyrazin-2-yl)ethylidene)hydrazine-1-carbothioamide

1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

O40PW12(3-)*3C14H16CoN10S2(1+)

O40PW12(3-)*3C14H16CoN10S2(1+)

Conditions
ConditionsYield
Stage #1: cobalt(II) nitrate hexahydrate; sodium tungstate (VI) dihydrate; 1-(1-(pyrazin-2-yl)ethylidene)thiosemicarbazide; 1,2-ethanediylbistetraphosphonic acid In methanol; water at 20℃; for 2h;
Stage #2: With hydrogenchloride In methanol; water at 130℃; for 72h; pH=3 - 3.35; Autoclave;
47.8%
potassium aquapentachlororuthenate(III)

potassium aquapentachlororuthenate(III)

1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

A

K9{ruthenium(III)3(ethylenediamine-N,N,N',N'-tetramethylphosphonato)2Cl8}*7H2O

K9{ruthenium(III)3(ethylenediamine-N,N,N',N'-tetramethylphosphonato)2Cl8}*7H2O

B

K3.5{ruthenium(III)5(ethylenediamine-N,N,N',N'-tetramethylphosphonic)2Cl2.5}*5H2O

K3.5{ruthenium(III)5(ethylenediamine-N,N,N',N'-tetramethylphosphonic)2Cl2.5}*5H2O

Conditions
ConditionsYield
In water Ru/EDTP = 2/1; complex added to hot soln. of ligand, heated for 1 h; pentahydrate washed with water, dried in vac. desiccator, filtrate evapd.; ground with ethanol; dried in vac. desiccator; TA; UV, elem. anal.;A 37%
B 8.1%
1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

water
7732-18-5

water

lead acetate
301-04-2

lead acetate

([Pb7(N,N,N',N'-ethylenediaminetetrakis(methylenephosphonic acid)(-7H))2(H2O)]*7H2O)(n)

([Pb7(N,N,N',N'-ethylenediaminetetrakis(methylenephosphonic acid)(-7H))2(H2O)]*7H2O)(n)

Conditions
ConditionsYield
With LiF; (C2H5)3N In ethanol; water High Pressure; adjusted to pH 5-6 with (C2H5)3N, kept in an autoclave at 140°C for 4 d; cooled slowly to room temp., crystals sepd. manually; elem. anal.;35%
potassium aquapentachlororuthenate(III)

potassium aquapentachlororuthenate(III)

1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

K2H{ruthenium(III)2(ethylenediamine-N,N,N',N'-tetramethylphosphonato)3Cl6}*12H2O

K2H{ruthenium(III)2(ethylenediamine-N,N,N',N'-tetramethylphosphonato)3Cl6}*12H2O

Conditions
ConditionsYield
In water equimolar quantity of reagents; heated on water-bath for 30 min; filtered; evapd.; ground with acetone; filtered off; dried in vac. desiccator; elem. anal.; TA; UV;27.2%
1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

C6H20N2O14P4

C6H20N2O14P4

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide In water at 60℃; pH 9;
1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

lanthanum(III) chloride
10099-58-8

lanthanum(III) chloride

La(3+)*5H(1+)*(O3PCH2)2NCH2CH2N(CH2PO3)2(8-)*H2O=LaH5((O3PCH2)2NCH2CH2N(CH2PO3)2)*H2O

La(3+)*5H(1+)*(O3PCH2)2NCH2CH2N(CH2PO3)2(8-)*H2O=LaH5((O3PCH2)2NCH2CH2N(CH2PO3)2)*H2O

Conditions
ConditionsYield
With potassium hydroxide In not given molar ratio La:ligand=1:1, pH=1.24-2.16 (pptn.); filtration, washing (EtOH, acetone, ether), drying (105°C); elem.anal.;
1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

lanthanum(III) chloride
10099-58-8

lanthanum(III) chloride

K(1+)*La(3+)*4H(1+)*(O3PCH2)2NCH2CH2N(CH2PO3)2(8-)*H2O=KLaH4((O3PCH2)2NCH2CH2N(CH2PO3)2)*H2O

K(1+)*La(3+)*4H(1+)*(O3PCH2)2NCH2CH2N(CH2PO3)2(8-)*H2O=KLaH4((O3PCH2)2NCH2CH2N(CH2PO3)2)*H2O

Conditions
ConditionsYield
With potassium hydroxide In not given molar ratio La:ligand=1:1, pH=3.65 (pptn.); filtration, washing (EtOH, acetone, ether), drying (105°C); elem.anal.;
cis-dichlorobis(ethylenediamine)cobalt(III) chloride

cis-dichlorobis(ethylenediamine)cobalt(III) chloride

1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

[Co(NH2CH2CH2NH2)2]C6H15N2P4O12

[Co(NH2CH2CH2NH2)2]C6H15N2P4O12

Conditions
ConditionsYield
In water 50°C, cooling 0°C; without separation;
cis-[CoCl(NH3)(ethylenediamine)2]Cl2

cis-[CoCl(NH3)(ethylenediamine)2]Cl2

1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

[Co(N2H4C2H4)2(NH3)]C6H16N2P4O12

[Co(N2H4C2H4)2(NH3)]C6H16N2P4O12

Conditions
ConditionsYield
In water 50°C, cooling 0°C; without separation;
1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

holmium(III) nitrate

holmium(III) nitrate

Ho(3+)*5H(1+)*C6H12N2O12P4(8-)*3H2O=Ho(H5C6H12N2O12P4)*3H2O

Ho(3+)*5H(1+)*C6H12N2O12P4(8-)*3H2O=Ho(H5C6H12N2O12P4)*3H2O

Conditions
ConditionsYield
In water ligand metal ion mole ratio 1.0:1.6; washing, drying in dry air at 25°C;
1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

holmium(III) nitrate

holmium(III) nitrate

4Ho(3+)*12H(1+)*3C6H12N2O12P4(8-)*25H2O=Ho4(H4C6H12N2O12P4)3*25H2O

4Ho(3+)*12H(1+)*3C6H12N2O12P4(8-)*25H2O=Ho4(H4C6H12N2O12P4)3*25H2O

Conditions
ConditionsYield
In water ligand metal ion mole ratio 0.5:0.6; washing, drying in dry air at 25°C;
1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

gadolinium(III) nitrate

gadolinium(III) nitrate

4Gd(3+)*12H(1+)*3C6H12N2O12P4(8-)*20H2O=Gd4(H4C6H12N2O12P4)3*20H2O

4Gd(3+)*12H(1+)*3C6H12N2O12P4(8-)*20H2O=Gd4(H4C6H12N2O12P4)3*20H2O

Conditions
ConditionsYield
In water ligand metal ion mole ratio 0.5:0.6; washing, drying in dry air at 25°C;
1,2-ethanediylbistetraphosphonic acid
1429-50-1

1,2-ethanediylbistetraphosphonic acid

gadolinium(III) nitrate

gadolinium(III) nitrate

Gd(3+)*5H(1+)*C6H12N2O12P4(8-)*6H2O=Gd(H5C6H12N2O12P4)*6H2O

Gd(3+)*5H(1+)*C6H12N2O12P4(8-)*6H2O=Gd(H5C6H12N2O12P4)*6H2O

Conditions
ConditionsYield
In water ligand metal ion mole ratio 1.0:1.6; washing, drying in dry air at 25°C;

Ethylenebis(nitrilodimethylene)tetraphosphonic acid Chemical Properties


IUPAC Name: [2-[Bis(phosphonomethyl)amino]ethyl-(phosphonomethyl)amino]methylphosphonic acid
Molecular Formula: C6H20N2O12P4 
Molecular Weight: 436.12 g/mol
Canonical SMILES: P(CN(CP(O)(O)=O)CCN(CP(O)(O)=O)CP(O)(O)=O)(O)(O)=O
InChI: InChI=1/C6H20N2O12P4/c9-21(10,11)3-7(4-22(12,13)14)1-2-8(5-23(15,16)17)6-24(18,19)20/h1-6H2,(H2,9,10,11)(H2,12,13,14)(H2,15,16,17)(H2,18,19,20) 
EINECS: 215-851-5
Classification Code: Chelating agents
Product Categories: Organics; Phosphonate antiscalant
XLogP3-AA: -11.2
H-Bond Donor: 8
H-Bond Acceptor: 14
Rotatable Bond Count: 11
Exact Mass: 435.99667
MonoIsotopic Mass: 435.99667
Topological Polar Surface Area: 237
Heavy Atom Count: 24 
Complexity: 486
Index of Refraction: 1.622 
Molar Refractivity: 77.06 cm3 
Molar Volume: 218.7 cm3 
Polarizability: 30.55×10-24 cm3 
Surface Tension: 134.2 dyne/cm 
Density: 1.993 g/cm
Flash Point: 485.2 °C 
Enthalpy of Vaporization: 138.57 kJ/mol 
Boiling Point: 878.7 °C at 760 mmHg 
Vapour Pressure of Ethylenebis(nitrilodimethylene)tetraphosphonic acid (CAS NO.1429-50-1): 2.43E-34 mmHg at 25 °C

Ethylenebis(nitrilodimethylene)tetraphosphonic acid Safety Profile

Hazard Codes: IrritantXi
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements of Ethylenebis(nitrilodimethylene)tetraphosphonic acid (CAS NO.1429-50-1): 26-36/37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.

Ethylenebis(nitrilodimethylene)tetraphosphonic acid Specification

 Ethylenebis(nitrilodimethylene)tetraphosphonic acid (CAS NO.1429-50-1), its Synonyms are (Ethylenedinitrilo)-tetramethylenephosphonic acid ; Ethylenediamine tetrakis(methylene phosphonic acid) ; (Ethane-1,2-diylbis(nitrilobis(methylene)))tetrakisphosphonic acid ; Phosphonic acid, (1,2-ethanediylbis(nitrilobis(methylene)))tetrakis- ; Phosphonic acid, P,P',P'',P'''-(1,2-ethanediylbis(nitrilobis(methylene)))tetrakis- .

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