1806-54-8

Basic information

• Product Name: trioctyl phosphate
• Synonyms: TRI-N-OCTYLPHOSPHATE;tri-n-octyl;Phosphoric acid trioctyl;WVPGXJOLGGFBCR-UHFFFAOYSA-N
• CAS NO: 1806-54-8
• Molecular Formula: C₂₄H₅₁O₄P
• Molecular Weight: 434.63
• EINECS: 217-305-1
• Mol File: 1806-54-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: -73.8°C
• Boiling Point: 230.5°C
• Flash Point: 218°C
• Appearance: /liquid
• Density: 0.928
• Vapor Pressure: 1.06E-06mmHg at 25°C
• Refractive Index: 1.448
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: trioctyl phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: trioctyl phosphate(1806-54-8)
• EPA Substance Registry System: trioctyl phosphate(1806-54-8)

Safety Data

• Hazardous Substances Data: 1806-54-8(Hazardous Substances Data)

Usage

Chemical Properties

colourless viscous liquid

General Description

Clear colorless liquid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Organophosphates, such as trioctyl phosphate, are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides. trioctyl phosphate is probably combustible. Producing noxious gases, i.e. phosphine, phosphorus oxides..

Health Hazard

ACUTE/CHRONIC HAZARDS: trioctyl phosphate is a cholinesterase inhibitor.

Fire Hazard

trioctyl phosphate is probably combustible.

InChI:InChI=1/C24H51O4P/c1-4-7-10-13-16-19-22-26-29(25,27-23-20-17-14-11-8-5-2)28-24-21-18-15-12-9-6-3/h4-24H2,1-3H3

Synthetic route

octanol (111-87-5) → tri-n-octyl phosphate (1806-54-8)

Conditions	Yield
With trichlorophosphate In cyclohexanone at 10 - 30℃; under 10 Torr; for 4h;	97.6%
With sodium hexachloroplatinate; phosphan at 174.9℃; Rate constant; Mechanism; var. temp., other alcohols;
With pyridine; diethyl ether; trichlorophosphate
With sodium hexachloroplatinate; phosphan at 25 - 40℃; Condensation;
With pyridine; iodine; triphenylphosphine at 50℃; under 1.7E-05 Torr; Kinetics;	100 % Chromat.

octanol (111-87-5) → 1-Chlorooctane (111-85-3) + tri-n-octyl phosphate (1806-54-8)

Conditions	Yield
With phosphan; chlorine Rate constant; Thermodynamic data; Ea, ΔS(excit.); also in the presence of pyridine;

excessive octanol(1) → tri-n-octyl phosphate (1806-54-8)

Conditions	Yield
With trichlorophosphate at 30 - 55℃;
With trichlorophosphate at 30 - 55℃;

octanol (111-87-5) + diphenylzinc (1078-58-6) → tri-n-octyl phosphate (1806-54-8) + octyl phenyl(phenyl)phosphinate (3389-73-9) + dioctyl phenylphosphonate (1754-47-8)

Conditions	Yield
Stage #1: diphenylzinc With trichlorophosphate In diethyl ether at 20℃; for 21.5h; Inert atmosphere; Stage #2: octanol With pyridine In diethyl ether at 20℃; for 29h; Inert atmosphere;	A n/a B n/a C 0.55 g

tri-n-octyl phosphate (1806-54-8) + toluene-4-sulfonic acid (104-15-4) → 1-octyl p-toluenesulfonate (3386-35-4) + 4-sec-octyltoluene (90734-22-8)

Conditions	Yield
In toluene for 9h; Heating;	A 30% B 60%

tri-n-octyl phosphate (1806-54-8) + toluene-4-sulfonic acid (104-15-4) + toluene (108-88-3) → 1-octyl p-toluenesulfonate (3386-35-4) + 4-sec-octyltoluene (90734-22-8)

Conditions	Yield
In toluene for 9h; Heating;	A 30% B 60%

maleic anhydride (108-31-6) + 1,2-dimethoxybenzene (91-16-7) + tri-n-octyl phosphate (1806-54-8) → C20H28O5

Conditions	Yield
Stage #1: maleic anhydride; tri-n-octyl phosphate; aluminum (III) chloride In chlorobenzene at 10℃; Stage #2: 1,2-dimethoxybenzene In chlorobenzene at 10 - 15℃; for 4h; Product distribution / selectivity;	59.8%

tri-n-octyl phosphate (1806-54-8) → phosphoric acid dioctyl ester; magnesium salt (27560-35-6)

Conditions	Yield
With magnesium bromide In dichloromethane Heating;

tri-n-octyl phosphate (1806-54-8) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8) → hydrogenchloride (7647-01-0) + 1-Chlorooctane (111-85-3) + oct-1-ene (111-66-0)

Conditions	Yield

Upstream product

• 111-87-5 octanol 
• 1078-58-6 diphenylzinc 

Downstream Products

• 7647-01-0 hydrogenchloride 
• 111-85-3 n-chlorooctane 
• 111-66-0 oct-1-ene 
• 3386-35-4 1-octyl p-toluenesulfonate 
• 90734-22-8 4-sec-octyltoluene 
• 27560-35-6 phosphoric acid dioctyl ester; magnesium salt 

Relevant articles and documents

Selective Substitution of POCl 3 with Organometallic Reagents: Synthesis of Phosphinates and Phosphonates

The selectivity of the substitution reaction of phosphoryl chloride with organometallic reagents was investigated using NMR spectroscopy. This led to the discovery that the selectivity of the substitution reaction can be tuned by choosing a proper organometallic reagent. A phosphinate could be obtained by using a Grignard reagent whereas an organozinc reagent provided a phosphonate. Based on these results, one-pot synthetic methods for the preparation of phosphinates and phosphonates using commercially available starting materials were developed. Both methods allow the synthesis of a broad range of either phosphinate or phosphonate derivatives in a straightforward and general procedure. Moreover, using these one-pot procedures, mixed systems substituted with different alkyl/aryl groups can be prepared.

Oxidizing alkoxylation of phosphine in alcoholic solutions of iodine

Oxidizing alkoxylation of PH3 to trialkyl phosphates was performed in pyridine-alcoholic solutions of iodine. The optimal conditions of the reaction were found.

PREPARATION OF ALKYLDIHYDROXYALKYLPHOSPHINE OXIDES AND TRIALKYL PHOSPHATES FROM PHOSPHINE AND ALCOHOLS IN THE PRESENCE OF PLATINUM(IV) HALIDES

31P NMR spectroscopy, gas chromatography, and potentiometric methods indicate that an alcoholic solution of Na2PtCl6 rapidly absorbs even traces of PH3 at 373-423 K to give trialkyl phosphates and alkyldihydroxyalkylphosphine oxides, platinum(IV) being reduced to platinum(0). At high temperatures oxidative C-phosphorylation prevails, while at low temperatures O-phosphorylation of alcohols by phosphine dominates. The rate of oxidative C- and O-phosphorylation of alcohol increases with increase in the concentrations of alcohol, phosphine, NaBr, NaI, Pt(IV) and Pt(II) and falls when H2O, HCl, or NaCl are added. Methods of chemical modeling and isolation of intermediate products show that phosphates are formed via stages of oxidation of dialkyl hydrogen phosphites resulting from dealkylation of trialkyl phosphites, while phosphine oxides are formed by isomerization of trihydroxyalkylphosphines.