Bis(2-ethylhexyl) phosphate supplier

Name
Bis(2-ethylhexyl) phosphate
EINECS 206-056-4
CAS No. 298-07-7
Article Data18
CAS DataBase
Density 0.983 g/cm³
Solubility slightly soluble in water
Melting Point -60 °C(lit.)
Formula C₁₆H₃₅O₄P
Boiling Point 393.4 °C at 760 mmHg
Molecular Weight 322.425
Flash Point 191.7 °C
Transport Information UN 1902 8/PG 3
Appearance clear colorless to light yellow liquid
Safety 26-36/37/39-45-25
Risk Codes 21-34
Molecular Structure
Hazard Symbols C
Synonyms 1-Hexanol,2-ethyl-, hydrogen phosphate (7CI);2-Ethyl-1-hexanol hydrogen phosphate;A208;A 208 (phosphate);Bis(2-ethylhexyl) hydrogen phosphate;Bis(2-ethylhexyl)orthophosphate;D 2EHPA;Dehpa extractant;DP 8;DP 8R;Di(2-ethylhexyl) phosphate;Di(2-ethylhexyl)phosphoric acid;O,O-Di(2-ethylhexyl)phosphoric acid;Phosphoric acid di(2-ethylhexyl) ester;Di-(2-ethylhexyl) phosphoric acid;
PSA 65.57000
LogP 5.55280

Synthetic route

: 104-76-7
2-Ethylhexyl alcohol

A: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

B: 78-42-2
tris(2-ethylhexyl) phosphate

Conditions

Conditions	Yield
With pyridine; trichlorophosphate In neat (no solvent) at 88℃; for 0.0208333h; Microwave irradiation;	A n/a B 75%

: 104-76-7
2-Ethylhexyl alcohol

A: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

B: 78-42-2
tris(2-ethylhexyl) phosphate

C: 1070-03-7
2-ethylhexylphosphoric acid

Conditions

Conditions	Yield
With phosphorus pentoxide at 21℃; for 0.616667h; Product distribution; Mechanism; var.temps. and time;	A 21.9% B 25% C 15.6%

...Expand

: 3658-48-8
bis(2-ethylhexyl)phosphite

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

Conditions

Conditions	Yield
With Nitrogen dioxide
Multi-step reaction with 2 steps 1: sulfuryl chloride 2: aqueous NaOH-solution View Scheme
Multi-step reaction with 2 steps 1: chlorine 2: aqueous NaOH-solution View Scheme
With Nitrogen dioxide at 35℃; Cooling;

: 63449-80-9
bis(2-ethylhexyl) phosphorochloridate

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

Conditions

Conditions	Yield
With sodium hydroxide
With sodium hydroxide
With water In toluene for 1h; Reflux;	49.3 g

: 104-76-7
2-Ethylhexyl alcohol

A: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

B: 1070-03-7
2-ethylhexylphosphoric acid

Conditions

Conditions	Yield
With phosphorus pentaoxide microwave irradiation;

: 78-42-2
tris(2-ethylhexyl) phosphate

A: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

B: 1070-03-7
2-ethylhexylphosphoric acid

Conditions

Conditions	Yield
With sodium hydroxide In methanol; water at 100℃; for 2h; Title compound not separated from byproducts.;

: 104-76-7
2-Ethylhexyl alcohol

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium / 160 °C 2: nitrogen dioxide View Scheme
Multi-step reaction with 3 steps 1: sodium / 160 °C 2: sulfuryl chloride 3: aqueous NaOH-solution View Scheme
Multi-step reaction with 2 steps 1: sodium / 160 °C 2: nitrogen dioxide View Scheme

: 685498-13-9
di-2-ethylhexyl phosphite

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: (chlorination) 2: aq. NaOH View Scheme

: copper(II) di(2-ethylhexyl)phosphate

: 144-62-7
oxalic acid

A: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

B: 814-91-5
copper(II) oxalate

Conditions

Conditions	Yield
In tetrachloromethane; water at 29.2℃; for 0.388889h; Kinetics; Further Variations:; reaction times, electrostatic field effects;

...Expand

: 1369964-84-0
(1,1-dioxido-4-oxo-3-phenyl-4H-thiochromen-2-yl)methyl bis(2-ethylhexyl) phosphate

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

Conditions

Conditions	Yield
In chloroform-d1 for 0.216667h; Irradiation;	> 99 %Spectr.

: 258864-54-9
trihexyl(tetradecyl)phosphonium chloride

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: trihexyltetradecylphosphonium bis(2-ethylhexyl) phosphate

Conditions

Conditions	Yield
With sodium hydroxide In water; toluene at 70℃;	99%

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: 2304-30-5
tetra-n-butylphosphonium chloride

: tetrabutylphosphonium bis(2-ethylhexyl) phosphate

Conditions

Conditions	Yield
With sodium hydroxide In water; toluene at 70℃;	98%

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: aluminum L-lactate

: 3C16H34O4P(1-)*Al(3+)

Conditions

Conditions	Yield
In water for 24h; Reflux;	98%
In water Reflux;

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: 683-10-3
carboxymethyl-dodecyl-dimethyl-ammonium betaine

: C16H34NO2(1+)*C16H34O4P(1-)

Conditions

Conditions	Yield
In ethanol at 25℃; for 0.5h;	98%

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: 97-93-8
triethylaluminum

: 3C16H34O4P(1-)*Al(3+)

Conditions

Conditions	Yield
In toluene for 12h; Inert atmosphere; Reflux;	96%

: neodymium(III) chloride

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: 82356-80-7
(1,3-dibutyl-1,1,3,3-tetramethyldisilyl)amine

: C12H30NSi2(1-)*C16H34O2P(1-)*C16H34O4P(1-)*Nd(3+)

Conditions

Conditions	Yield
In tetrahydrofuran at 30℃; for 0.333333h; Inert atmosphere;	95%

...Expand

: 35203-44-2
1-propyl-1H-imidazole

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: 51065-82-8
(3-bromopropyl)(phenyl)phosphinic acid ethyl ester

: C17H26N2O2P(1+)*C16H34O4P(1-)

Conditions

Conditions	Yield
Stage #1: 1-propyl-1H-imidazole; (3-bromopropyl)(phenyl)phosphinic acid ethyl ester In toluene at 85℃; for 6h; Stage #2: Bis(2-ethylhexyl)phosphoric acid With sodium for 24h; Reflux; Stage #3: In dichloromethane at 20℃; for 3h;	94%

...Expand

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: 107-43-7
betaine

: betainium bis(2-ethylhexyl)phosphate

Conditions

Conditions	Yield
In ethanol at 25℃; for 0.5h;	94%

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: 100-39-0
benzyl bromide

: benzyl bis(2-ethylhexyl) phosphate

Conditions

Conditions	Yield
With caesium carbonate In acetonitrile at 100℃; for 12h; Inert atmosphere;	93%

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: 7281-04-1
ajatin

: benzyldimethyldodecylammonium di (2-ethylhexyl)phosphate

Conditions

Conditions	Yield
With sodium carbonate In water at 25℃; for 24h; Inert atmosphere;	93%

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: 121934-92-7
3-(bromopropyl)(diphenyl)phosphine oxide

: 33529-01-0
1-hexylimidazole

: C24H32N2OP(1+)*C16H34O4P(1-)

Conditions

Conditions	Yield
Stage #1: 3-(bromopropyl)(diphenyl)phosphine oxide; 1-hexylimidazole In toluene at 85℃; for 6h; Stage #2: Bis(2-ethylhexyl)phosphoric acid With sodium for 24h; Reflux; Stage #3: In dichloromethane at 20℃; for 3h;	93%

...Expand

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: C8H17NO2

: C8H18NO2(1+)*C16H34O4P(1-)

Conditions

Conditions	Yield
In ethanol at 25℃; for 0.5h;	92%

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: 121934-92-7
3-(bromopropyl)(diphenyl)phosphine oxide

: 19768-54-8
N-pentyl imidazole

: C23H30N2OP(1+)*C16H34O4P(1-)

Conditions

Conditions	Yield
Stage #1: 3-(bromopropyl)(diphenyl)phosphine oxide; N-pentyl imidazole In toluene at 85℃; for 6h; Stage #2: Bis(2-ethylhexyl)phosphoric acid With sodium for 24h; Reflux; Stage #3: In dichloromethane at 20℃; for 3h;	91%

...Expand

: neodymium(III) chloride

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: (1,3-diphenyl-1,1,3,3-tetrapropyldisilyl)amine

: C16H34O2P(1-)*C16H34O4P(1-)*C24H38NSi2(1-)*Nd(3+)

Conditions

Conditions	Yield
In tetrahydrofuran at 40℃; for 0.333333h; Inert atmosphere;	91%

...Expand

: 35203-44-2
1-propyl-1H-imidazole

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: 121934-92-7
3-(bromopropyl)(diphenyl)phosphine oxide

: C21H26N2OP(1+)*C16H34O4P(1-)

Conditions

Conditions	Yield
Stage #1: 1-propyl-1H-imidazole; 3-(bromopropyl)(diphenyl)phosphine oxide In toluene at 85℃; for 8h; Stage #2: Bis(2-ethylhexyl)phosphoric acid With sodium for 23h; Reflux; Stage #3: In dichloromethane at 20℃; for 3h;	90%

...Expand

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: 1186-10-3
diethyl 3-(bromopropyl)phosphonic acid

: 33529-01-0
1-hexylimidazole

: C16H32N2O3P(1+)*C16H34O4P(1-)

Conditions

Conditions	Yield
Stage #1: diethyl 3-(bromopropyl)phosphonic acid; 1-hexylimidazole In toluene at 85℃; for 6h; Stage #2: Bis(2-ethylhexyl)phosphoric acid With sodium for 25h; Reflux; Stage #3: In dichloromethane at 20℃; for 2h;	90%

...Expand

: 4316-42-1
1-Butylimidazole

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: 121934-92-7
3-(bromopropyl)(diphenyl)phosphine oxide

: C22H28N2OP(1+)*C16H34O4P(1-)

Conditions

Conditions	Yield
Stage #1: 1-Butylimidazole; 3-(bromopropyl)(diphenyl)phosphine oxide In toluene at 85℃; for 4h; Stage #2: Bis(2-ethylhexyl)phosphoric acid With sodium for 24h; Reflux; Stage #3: In dichloromethane at 20℃; for 3h;	90%

...Expand

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: 130776-67-9
7,7-dimethyloctanoic acid

: neodymium chloride hydrate

: Nd [(neodecanoate)2(bis(2-ethylhexyl)phosphate)1]

Conditions

Conditions	Yield
Stage #1: Bis(2-ethylhexyl)phosphoric acid; 7,7-dimethyloctanoic acid With sodium hydroxide In ethanol; water at 50℃; for 2h; Stage #2: neodymium chloride hydrate In tetrahydrofuran; water at 50℃; for 15h;	89%

...Expand

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: 1186-10-3
diethyl 3-(bromopropyl)phosphonic acid

: 19768-54-8
N-pentyl imidazole

: C15H30N2O3P(1+)*C16H34O4P(1-)

Conditions

Conditions	Yield
Stage #1: diethyl 3-(bromopropyl)phosphonic acid; N-pentyl imidazole In toluene at 85℃; for 6h; Stage #2: Bis(2-ethylhexyl)phosphoric acid With sodium for 24h; Reflux; Stage #3: In dichloromethane at 20℃; for 4h;	88%

...Expand

: neodymium(III) chloride

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: 3449-26-1
1,1,3,3-tetramethyl-1,3-diphenyldisilazane

: C16H22NSi2(1-)*C16H34O2P(1-)*C16H34O4P(1-)*Nd(3+)

Conditions

Conditions	Yield
In tetrahydrofuran at 25℃; for 0.5h; Inert atmosphere;	88%

...Expand

: 4316-42-1
1-Butylimidazole

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: 1186-10-3
diethyl 3-(bromopropyl)phosphonic acid

: C14H28N2O3P(1+)*C16H34O4P(1-)

Conditions

Conditions	Yield
Stage #1: 1-Butylimidazole; diethyl 3-(bromopropyl)phosphonic acid In toluene at 85℃; for 6h; Stage #2: Bis(2-ethylhexyl)phosphoric acid With sodium for 24h; Reflux; Stage #3: In dichloromethane at 20℃; for 3h;	87%

...Expand

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: 121934-92-7
3-(bromopropyl)(diphenyl)phosphine oxide

: 603-35-0
triphenylphosphine

: C33H31OP2(1+)*C16H34O4P(1-)

Conditions

Conditions	Yield
Stage #1: 3-(bromopropyl)(diphenyl)phosphine oxide; triphenylphosphine In toluene at 80℃; for 10h; Stage #2: Bis(2-ethylhexyl)phosphoric acid With sodium In dichloromethane at 20℃; for 2h;	86%

...Expand

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: 121934-92-7
3-(bromopropyl)(diphenyl)phosphine oxide

: 121-44-8
triethylamine

: C21H31NOP(1+)*C16H34O4P(1-)

Conditions

Conditions	Yield
Stage #1: 3-(bromopropyl)(diphenyl)phosphine oxide; triethylamine In toluene at 80℃; for 0.333333h; Microwave irradiation; Stage #2: Bis(2-ethylhexyl)phosphoric acid With sodium In dichloromethane; water at 20℃; for 27h;	86%

...Expand

: 35203-44-2
1-propyl-1H-imidazole

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: 1186-10-3
diethyl 3-(bromopropyl)phosphonic acid

: C13H26N2O3P(1+)*C16H34O4P(1-)

Conditions

Conditions	Yield
Stage #1: 1-propyl-1H-imidazole; diethyl 3-(bromopropyl)phosphonic acid In toluene at 85℃; for 6h; Stage #2: Bis(2-ethylhexyl)phosphoric acid With sodium for 24h; Reflux; Stage #3: In dichloromethane at 20℃; for 3h;	86%

...Expand

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: 603-35-0
triphenylphosphine

: 176849-72-2
5-(bromopentyl)(diphenyl)phosphine oxide

: C35H35OP2(1+)*C16H34O4P(1-)

Conditions

Conditions	Yield
Stage #1: triphenylphosphine; 5-(bromopentyl)(diphenyl)phosphine oxide In benzene at 85℃; for 9h; Stage #2: Bis(2-ethylhexyl)phosphoric acid With sodium In dichloromethane at 20℃; for 3h;	85%

...Expand

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: 603-35-0
triphenylphosphine

: 156488-37-8
4-bromo-n-butyldiphenylphosphine oxide

: C34H33OP2(1+)*C16H34O4P(1-)

Conditions

Conditions	Yield
Stage #1: triphenylphosphine; 4-bromo-n-butyldiphenylphosphine oxide In toluene at 75℃; for 10h; Stage #2: Bis(2-ethylhexyl)phosphoric acid With sodium In dichloromethane at 20℃; for 4h;	85%

...Expand

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: 51065-82-8
(3-bromopropyl)(phenyl)phosphinic acid ethyl ester

: 121-44-8
triethylamine

: C17H31NO2P(1+)*C16H34O4P(1-)

Conditions

Conditions	Yield
Stage #1: (3-bromopropyl)(phenyl)phosphinic acid ethyl ester; triethylamine In benzene at 85℃; for 0.416667h; Microwave irradiation; Stage #2: Bis(2-ethylhexyl)phosphoric acid With sodium In dichloromethane; water at 20℃; for 27h;	85%

...Expand

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: 66003-76-7
Diphenyliodonium triflate

: C21H37O4P

Conditions

Conditions	Yield
With triethylamine In toluene at 110℃; for 3h; Inert atmosphere;	83%

: 67-56-1
methanol

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: bis(2-ethylhexyl) methyl phosphate

Conditions

Conditions	Yield
With copper(l) iodide; sodium carbonate; triethylamine In tetrachloromethane at 80℃; for 12h;	83%
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In 1,2-dichloro-ethane at 20℃; for 12h; Schlenk technique; Inert atmosphere;	55%

: Iron(III) nitrate nonahydrate

: 298-07-7
Bis(2-ethylhexyl)phosphoric acid

: Fe2{di(2-ethylhexyl)phosphate}5{di(2-ethylhexyl)phosphoric acid}(NO3)

Conditions

Conditions	Yield
In acetic acid the phosphoric acid/acetic acid added dropwise with vigorous stirring to Fe-compd./acetic acid, color change of soln. from rust-red to yellow with rapid deposition of solids, mixt. white after addn. completed; solid collected, dispersed in acetic acid, stirred, filtered off, dried (vac., room temp., to constant wt.), recrystn. (min. amt. cyclohexane contg. small amt. acetone, pptn. with acetone; half the product remains in mother liquor), elem. anal.;	82%

Yield

In acetic acid the phosphoric acid/acetic acid added dropwise with vigorous stirring to Fe-compd./acetic acid, color change of soln. from rust-red to yellow with rapid deposition of solids, mixt. white after addn. completed; solid collected, dispersed in acetic acid, stirred, filtered off, dried (vac., room temp., to constant wt.), recrystn. (min. amt. cyclohexane contg. small amt. acetone, pptn. with acetone; half the product remains in mother liquor), elem. anal.;

82%

Bis(2-ethylhexyl) phosphate Consensus Reports

Reported in EPA TSCA Inventory.

Bis(2-ethylhexyl) phosphate Specification

The Bis(2-ethylhexyl) phosphate, with the CAS registry number 298-07-7 and EINECS registry number 206-056-4, has the systematic name and IUPAC name of bis(2-ethylhexyl) hydrogen phosphate. It is a kind of clear colorless to light yellow liquid, and belongs to the following product categories of Industrial/Fine Chemicals and Organics. And the molecular formula of this chemical is C₁₆H₃₅O₄P. What's more, it is usually used as plasticizer and solvent in the synthesis of plastic.

The physical properties of Bis(2-ethylhexyl) phosphate are as followings: (1)ACD/LogP: 6.09; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 2.7; (4)ACD/LogD (pH 7.4): 2.59; (5)ACD/BCF (pH 5.5): 10.17; (6)ACD/BCF (pH 7.4): 7.87; (7)ACD/KOC (pH 5.5): 19.95; (8)ACD/KOC (pH 7.4): 15.44; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 14; (12)Polar Surface Area: 54.57 Å²; (13)Index of Refraction: 1.449; (14)Molar Refractivity: 87.99 cm³; (15)Molar Volume: 327.7 cm³; (16)Polarizability: 34.88×10^-24cm³; (17)Surface Tension: 34 dyne/cm; (18)Density: 0.983 g/cm³; (19)Flash Point: 191.7 °C; (20)Enthalpy of Vaporization: 70.61 kJ/mol; (21)Boiling Point: 393.4 °C at 760 mmHg; (22)Vapour Pressure: 2.75E-07 mmHg at 25°C.

Preparation: First, 2-Ethylhexyl alcohol react with phosphorus to produce iso-octyl phosphate chloride, and it is a esterification reaction. Second, dissove the iso-octyl phosphate chloride with lye. Third, acidified it with sulfuric acid.
2C₈H₁₇OH+POCl₃→(C₈H₁₇)₂POCl+2HCl
C₈H₁₇)₂POCl+NaOH→(C₈H₁₇)₂POONa+HCl
(C₈H₁₇)₂POONa+H₂SO₄→(C₈H₁₇)₂POOH+Na₂SO₄

You should be cautious while dealing with this chemical. It is harmful in contact with skin, and may cause burns. Therefore, you had better take the following instructions: Avoid contact with eyes; Wear suitable protective clothing, gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice; In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: O=P(OCC(CC)CCCC)(OCC(CCCC)CC)O
(2)InChI: InChI=1/C16H35O4P/c1-5-9-11-15(7-3)13-19-21(17,18)20-14-16(8-4)12-10-6-2/h15-16H,5-14H2,1-4H3,(H,17,18)
(3)InChIKey: SEGLCEQVOFDUPX-UHFFFAOYAP

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LDLo	intraperitoneal	62500ug/kg (62.5mg/kg)		"Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 9, Pg. 132, 1957.
rabbit	LD50	skin	1250uL/kg (1.25mL/kg)		Union Carbide Data Sheet. Vol. 5/18/1972,
rat	LD50	intraperitoneal	50mg/kg (50mg/kg)	LIVER: OTHER CHANGES	Hydrometallurgy. Vol. 3, Pg. 201, 1978.
rat	LD50	oral	4940uL/kg (4.94mL/kg)		Union Carbide Data Sheet. Vol. 5/18/1972,

Product Name

Bis(2-ethylhexyl) phosphate

Synthetic route

Bis(2-ethylhexyl) phosphate Consensus Reports

Bis(2-ethylhexyl) phosphate Specification

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