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Tributyl phosphate

Product Name:
Tributyl phosphate
CAS No.
126-73-8
Chemical Name:
Tributyl phosphate
CBNumber:
CB4187323
Molecular Formula:
C12H27O4P
Formula Weight:
266.31
MOL File:
126-73-8.mol
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Tributyl phosphate Property

Melting point:
-79 °C
Boiling point:
289 °C
Density 
0.979 g/mL at 25 °C(lit.)
vapor density 
9.2 (vs air)
vapor pressure 
27 mm Hg ( 178 °C)
refractive index 
n20/D 1.424(lit.)
Flash point:
380 °F
storage temp. 
Store below +30°C.
solubility 
water: soluble1ml in 165ml water
form 
Liquid
color 
Clear
Odor
Odorless
Water Solubility 
0.6 g/100 mL
Merck 
14,9618
BRN 
1710584
Exposure limits
TLV-TWA 2.18 mg/m3 (0.2 ppm) (ACGIH), 5 mg/m3 (OSHA and NIOSH); IDLH 1300 mg/m3 (120 ppm) (NIOSH).
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents. May be water sensitive.
CAS DataBase Reference
126-73-8(CAS DataBase Reference)
NIST Chemistry Reference
Tri-n-butylphosphate(126-73-8)
EPA Substance Registry System
Tributyl phosphate (126-73-8)
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Safety

Hazard Codes 
Xn,F
Risk Statements 
22-38-40-62-48/20-36/37/38-11-20/22
Safety Statements 
36/37-46-45-36/37/39-16-53
RIDADR 
UN 1208 3/PG 2
WGK Germany 
2
RTECS 
TC7700000
Autoignition Temperature
770 °F
TSCA 
Yes
HS Code 
29190010
Hazardous Substances Data
126-73-8(Hazardous Substances Data)
Toxicity
LD50 orally in rats: 3.0 g/kg (Smyth, Carpenter)
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N-Bromosuccinimide Price More Price(20)

Sigma-Aldrich Gold
Product number:
00675
Product name :
Tributyl phosphate
Purity:
for extraction analysis, ≥99.0% (GC)
Packaging:
100ml
Price:
$54.4
Updated:
2019/12/02
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Sigma-Aldrich Gold
Product number:
00675
Product name :
Tributyl phosphate
Purity:
for extraction analysis, ≥99.0% (GC)
Packaging:
500ml
Price:
$164
Updated:
2019/12/02
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Alfa Aesar Gold
Product number:
A16084
Product name :
Tri-n-butyl phosphate, 98%
Packaging:
1000ml
Price:
$52.8
Updated:
2020/06/24
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Alfa Aesar Gold
Product number:
A16084
Product name :
Tri-n-butyl phosphate, 98%
Packaging:
250ml
Price:
$20.2
Updated:
2020/06/24
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Sigma-Aldrich Gold
Product number:
34108
Product name :
Tributyl phosphate
Purity:
analytical standard
Packaging:
2ml
Price:
$31.1
Updated:
2019/12/02
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Tributyl phosphate Chemical Properties,Usage,Production

Chemical Properties

Tributyl phosphate is an odorless colorless to yellow liquid. The solubility of TBP is only 280 mg/L in water at 25°C. It is soluble in diethyl ether, benzene, carbon disulfide. It can be miscible with ethanol. It is stable, but it is incompatible with strong oxidizing agents.

Uses

TBP is a trialkyl phosphate that is the tributyl ester of phosphoric acid. TBP is a toxic organophosphorous compound widely used in many industrial applications, including significant usage in nuclear processing. TBP is a solvent and plasticizer for cellulose esters such as nitrocellulose and cellulose acetate. The major uses of TBP in industry are as a component of aircraft hydraulic fluid and as a solvent for extraction and purification of rare earth metals from their ores, such as uranium and plutonium. TBP is used also in mercerizing liquids, where it improves their wetting properties. TBP is also used as a heat exchange medium. TBP is used in some consumer products such as herbicides and water thinned paints and tinting bases.

Potential Exposure

The industrial application of this chemical is responsible for occupational exposure and environmental pollution. Exposure to TBP can be from ingestion, inhalation, or skin or eye contact. This exposure will most often happen from occupational use of hydraulic fluid. If TBP is released to the environment, it will bind tightly to dust particles in the air. Unbound TBP will break down in air. It will move slowly through soil because it will bind with soil particles. It may volatilize slowly from moist soil and water surfaces. It may build up in aquatic organisms. It will be broken down in water by microbes.

Description

On decomposition, TBP releases COx, toxic fumes of phosphoric acid, phosphorus oxides, and/or phosphine. TBP is incompatible with strong oxidising agents and alkalis. The major uses of TBP in industry are as a component of aircraft hydraulic fluid and as a solvent for rare earth extraction and purification. Minor uses of TBP include use as a defoamer additive in cement casings for oil wells, an anti-air entrainment additive for coatings and floor finishes, as well as a carrier for fluorescent dyes. The major uses of TBP comprise over 80% of the volume produced.

Chemical Properties

Stable, colorless liquid; odorless. Miscible with most solvents and diluents; soluble in water. Combustible.

Physical properties

Clear, colorless to pale yellow, odorless, slightly flammable, oily liquid

Uses

Tributyl phosphate is used as a plasticizer for cellulose esters, vinyl resins, and lacquers; and in making fireretardants, biocides, defoamers, and catalysts.

Uses

Extractant for metal complexes.1

Uses

Plasticizer for cellulose esters, lacquers, plastics, and vinyl resins.

Definition

ChEBI: A trialkyl phosphate that is the tributyl ester of phosphoric acid.

Production Methods

Prepared by the reaction of phosphorus oxychloride with butyl alcohol.

Air & Water Reactions

Water insoluble. Reacts slowly with water under basic conditions.

Reactivity Profile

Tributyl phosphate is incompatible with strong oxidizing agents and strong bases. Attacks some forms of plastics and rubber .

Health Hazard

Toxic by ingestion and inhalation, irritant to skin, bladder, eye and upper respiratory tract. May cause stimulation of the central nervous system.

Health Hazard

Acute
Non-industrial:
There are no data on the toxicity of TBP to man. The TLV is established by the American Council of Governmental Industrial Hygienists on the basis of analogy with triphenyl phosphate with which it bears some similarities in its toxic properties (ACGIH 1986).
Industrial:
A personal communication to ACGIH notes that workers exposed to 15 mg/m3 of TBP have complained of nausea and headache (ACGIH 1986). There are no other documented reports of deleterious effects of TBP in industrial situations.
Chronic
Inhibition of human erythrocyte and plasma cholinesterase is reported to be weak, even in vitro (Hayes and Sabine 1952; Sandmeyer and Kirwin 1981).

Health Hazard

Tributyl phosphate is a neurotoxic compound and an irritant. The toxic effects are characteristic of organic phosphates. It inhibits cholinesterase activity and causes paralysis. Inaddition,itcancausedepressionofthecentralnervoussystem,aswellasirritationofthe skin,eyes,andrespiratorypassage.Inhalation toxicity data in the literature are inconsistent.
The oral toxicity in rats was low; the LD50 value was reported as 1189 mg/kg (NIOSH 1986).
The pure liquid instilled into rabbits’ eyes caused severe irritation but no permanent damage. The irritation effect on the skin is mild.
Tributyl phosphate exhibited teratogenic effects in rats. There is no report on its carcinogenicity..

Fire Hazard

Special Hazards of Combustion Products: Toxic fumes of PO x

Industrial uses

1. As an antifoaming agent.
2. As a plasticizer for cellulose esters, lacquers, plastics, and vinyl resins.
3. As a complexing agent in the extraction of heavy metals, especially for the extraction of metal ions from solutions of reactor products in nuclear fuel reprocessing.
4. As an aircraft hydraulic fluid.
5. As a heat exchange medium and dielectric.
6. As a pigment-grinding agent.

Safety Profile

Poison by intraperitoneal and intravenous routes. Moderately toxic by ingestion, inhalation, and subcutaneous routes. Experimental reproductive effects. A skin, eye, and mucous membrane irritant. Combustible when exposed to heat or flame. To fight fire, use CO2, dry chemical, fog, mist. When heated to decomposition it emits toxic fumes of POx.

Environmental Fate

Biological. Indigenous microbes in Mississippi River water degraded tributyl phosphate to carbon dioxide. After 4 wk, 90.8% of the theoretical carbon dioxide had evolved (Saeger et al., 1979).
Chemical/Physical. Complete hydrolysis yields 1-butanol and phosphoric acid via the intermediates dibutyl phosphate and monobutyl phosphate (Thomas and Macaskie, 1996).

Metabolism

A system was developed utilizing isolated anterior forearm stratum corneum conjunctum of man to study skin penetrating capacity of a series of organic phosphates. TBP was tested in the system and was among the least penetrating of the compounds tested, only phosphoric acid and tri-o-cresyl phosphate penetrating less well. The value given was μmoles/cm2/min as the average maximum steady-state rate of penetration. In a comparative study with 3 living subjects, penetration was essentially the same as in the isolated skin preparation (Marzulli et al 1965).
Rats given a single oral dose of [14C]-labeled TBP at 14 mg/kg excreted 50, 10, and 6% of the administered dose in the urine, exhaled air, and feces, respectively, within 24 h. A single intraperitoneal dose at the same rate resulted in 70,7, and 4% of the administered dose in the urine, exhaled air, and feces within the first 24 h (Suzuki et al 1984).
Single oral administration of TBP to rats at 156 mg/kg led to its appearance in all the tissues in the first 30 min. The major amount was in the gastrointestinal tract where it was poorly absorbed and was rapidly eliminated. The total level of TBP in all other organs and tissues was 5.73%, but none was detected after 3 d (Khalturin and Andryushkeeva 1986).
A single i.p. dose of TBP at 250 mg/kg to rats resulted in 11 phosphoruscontaining metabolites in the urine within 24 h. The principal metabolic pathway resulted in stepwise debutylation, through hydroxylated intermediates, to give dibutyl hydrogen phosphate and butyl dihydrogen phosphate. Butyl bis(3-hydroxybutyl) phosphate and small amounts of monohydroxylated butyl derivatives also were isolated. Several metabolites, presumably resulting from omegaoxidation of the ?-butyl moieties to give butyric acid derivatives, also were detected, the result of a secondary pathway. In addition, butyl 2-hydroxybutyl hydrogen phosphate was isolated and characterized. The administration of a possible intermediate, dibutyl 3-oxobutyl phosphate, gave a metabolic profile similar to that of dibutyl 3-hydroxybutyl phosphate, the major metabolite, thus supporting the view that this compound was on the major metabolic pathway. Separate direct administration of various hydroxylated metabolites supported the metabolic pathways proposed (Suzuki et al 1984).
Rat liver microsomal preparations also metabolized TBP to mono- and dihydroxylated intermediates, giving dibutyl hydrogen phosphate as the terminal metabolite (Sasaki et al 1984). Microsomal preparations from goldfish liver and killifish also resulted in dibutyl 3-hydroxybutyl phosphate and dibutyl hydrogen phosphate (Sasaki et al 1985).

Purification Methods

The main contaminants in commercial samples are organic pyrophosphates, monoand dibutyl phosphates and butanol. It is purified by washing successively with 0.2M HNO3 (three times), 0.2M NaOH (three times) and water (three times), then fractionally distilled under vacuum. [Yoshida J Inorg Nucl Chem 24 1257 1962.] It has also been purified via its uranyl nitrate addition compound, obtained by saturating the crude phosphate with uranyl nitrate. This compound is crystallised three times from n-hexane by cooling to -40o, and then decomposed by washing with Na2CO3 and water. Hexane is removed by steam distillation; the water is then evaporated under reduced pressure, and the residue is distilled under reduced pressure. [Siddall & Dukes J Am Chem Soc 81 790 1959.] Alternatively, wash it with water, then with 1% NaOH or 5% Na2CO3 for several hours, then finally with water. Dry it under reduced pressure and fractionate it carefully under vacuum. It is a stable colourless oil, sparingly soluble in H2O (1mL dissolves in 165mL of H2O), but freely miscible in organic solvents. [Kuivila & Masterton J Am Chem Soc 74 4953 1952, Cox & Westheimer J Am Chem Soc 80 5441 1958, 31P NMR: Van Wazer J Am Chem Soc 78 5715 1956, Fertig et al. J Chem Soc 1488 1957, Beilstein 1 IV 1531.]

Waste Disposal

Tributyl phosphate is dissolved in a combustible solvent and is burned in a chemical incinerator equipped with an afterburner and scrubber.

Tributyl phosphate Preparation Products And Raw materials Raw materials

Raw materials

Preparation Products

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Chemical Properties Uses Potential Exposure