Tributyl phosphate

Iupac Name：tributyl phosphate

Molecular Weight：266.31

Modify Date.: 2022-10-30 08:54

Introduction: 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 majoruses of TBP in industry are as a component of aircraft hydraulic fluid and as a solvent forrare earth extraction and purification. Minor uses of TBP include use as a defoamer additivein cement casings for oil wells, an anti-air entrainment additive for coatings and floorfinishes, as well as a carrier for fluorescent dyes. The major uses of TBP comprise over 80%of the volume produced. View more+

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1. Names and Identifiers

1.1 Name: Tributyl phosphate
1.2 Synonyms: 1-Carbamoyl-7-diaethylamino-3,4-dihydroxy-phenoxazinylium,Chlorid 1-carbamoyl-7-diethylamino-3,4-dihydroxy-phenoxazinylium,chloride AURORA KA-1641 BUTYL PHOSPHATE Celestin blue Celestin blue B CELESTINE BLUE Celluphos 4 Coreine Blue B Coreine RR No. 65 EINECS 204-800-2 Gallo Sky Blue B Gallo Sky Blue S MFCD00009436 n-butyl phosphate Nitrogen-Oxygen free radical piperidycol O,O,O-Tributylphosphate Phosphoric acid tributyl Phosphoric acid tributyl ester PHOSPHORIC ACID TRI-N-BUTYL ESTER Phosphoric acid, tributyl ester Phosphoric acid, tri-n-butyl ester TBP Tributilfosfato Tributyl phosphate 10g [126-73-8] Tributyl phosphate 5g [126-73-8] Tributylfosfaat Tributylphosphate TRIBUTYLPHOSPHATE extrapure Tributylphsophate tri-n-butyl phosphate

1.3 CAS No.: 126-73-8

1.4 CID: 31357

1.5 EINECS(EC#): 204-800-2

1.6 Molecular Formula: C12H27O4P (isomer)

1.7 Inchi: InChI=1S/C12H27O4P/c1-4-7-10-14-17(13,15-11-8-5-2)16-12-9-6-3/h4-12H2,1-3H3

1.8 InChkey: STCOOQWBFONSKY-UHFFFAOYSA-N

1.9 Canonical Smiles: CCCCOP(=O)(OCCCC)OCCCC

1.10 Isomers Smiles: CCCCOP(=O)(OCCCC)OCCCC

2. Properties

2.1 Density: 0.979 g/mL at 25 °C(lit.)

2.1 Melting point: -79 °C

2.1 Boiling point: 289 °C

2.1 Refractive index: n20/D 1.424(lit.)

2.1 Flash Point: 380 °F

2.2 Precise Quality: 266.16500

2.2 PSA: 54.57000

2.2 logP: 4.54460

2.2 Solubility: water: soluble1ml in 165ml water

2.3 Viscosity: Viscosity is a measure of a fluid's resistance to flow. It describes the internal friction of a moving fluid.

2.4 VaporDensity: 9.2 (vs air)

2.5 AnalyticLaboratory Methods: Method: NIOSH 5034, Issue 1; Procedure: gas chromatography using flame photometric detector with a phosphorus; filter; Analyte: tributyl phosphate;; Matrix: air; Detection Limit: 2 ug/sample.

2.6 Appearance: Clear liquid

2.7 AutoIgnition: 770° F (USCG, 1999)

2.8 Storage: Ambient temperatures.

2.9 Carcinogenicity: TBP was not genotoxic in a variety ofin vivo and in vitro assays.7 It has been suggestedthat the carcinogenic effects of TBP arespecies- and organ specific. The necroticactions of TBP (or a metabolite) on rat urinarybladder epithelium may induce chronic repairprocesses that cause the normal epithelium tobe transformed into its metaplastic and neoplasticforms.TBP was not teratogenic when administeredto rats and rabbits during gestation;fetotoxic effects (delayed ossification and reducedfetal body weights) occurred in rats atdoses that caused severe maternal toxicity.There was no evidence of reproductive toxicityor reproductive organ pathology in twogenerationstudies in rats fed TBP in the diet.

2.10 Chemical Properties: Tributyl phosphateis 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.

2.11 Physical Properties: Clear, colorless to pale yellow, odorless, slightly flammable, oily liquid

2.12 Color/Form: Clear

2.13 Decomposition: When heated to decomposition it emits toxic fumes of /phosphorous oxide/ (PO(x)).

2.14 Heat of Combustion: -1905.7 kcal/mol at 25 deg C

2.15 Heat of Vaporization: 55.1 cal/g at 289 deg C

2.16 Odor: Odorless

2.17 Odor Threshold: Odor perception threshold 0.014 mg/L.

2.18 Physical: TRIBUTYL PHOSPHATE; is an odorless colorless to yellow liquid. Toxic by ingestion and inhalation.

2.19 Water Solubility: 0.6 g/100 mL

2.20 Spectral Properties: SADTLER REFERENCE NUMBER: 138 (IR, PRISM)
Index of refraction = 1.4224 at 25 deg C
Intense mass spectral peaks: 99 m/z (100%), 155 m/z (32%), 211 m/z (30%), 57 m/z (15%)
IR: 1548 (Coblentz Society Spectral Collection)
NMR: 6338 (Sadtler Research Laboratories Spectral Collection)
MASS: 65137 (NIST/EPA/MSDC Mass Spectral Database 1990 version); 1217 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)

2.21 Stability: Stable. Combustible. Incompatible with strong oxidizing agents. May be water sensitive.

2.22 StorageTemp: Store below +30°C.

2.23 Surface Tension: 27.55 dyne/cm at 20 deg C

2.24 Toxicity Summary: IDENTIFICATION AND USE: Tributyl phosphate; is a colorless to pale-yellow odorless liquid. It is used as a plasticizer for cellulose esters, lacquers, plastics, and vinyl resins. Used in fire-resistant aircraft hydraulic fluids. Other uses include heat-exchange medium, solvent extraction of metal ions from solution of reactor products, solvent for nitrocellulose;, cellulose acetate;, pigment grinding assistant, antifoaming agent, dielectric. HUMAN EXPOSURE AND TOXICITY: Breathing vapors of tributyl phosphate; causes irritation of mucous membranes and if inhalation is prolonged there can be general poisoning with paralysis. In contact with skin tributyl phosphate; can cause irritation. Tributyl phosphate; may cause irritation of the eyes, nose, and throat. It may also cause nausea and headache. In a series of 42 patients with furniture related dermatitis, a positive patch test reaction was seen in 1 patient. In vitro it acts as androgen receptor, and glucocorticoid receptor antagonist. ANIMAL STUDIES: Tributyl phosphate; was not acutely toxic by dermal exposure in the rabbit and in the guinea pig. Application to either intact or abraded skin of rabbits and guinea pigs produced irritation with edema and erythema. The instillation of tributyl phosphate; in the conjunctival sac of rabbits gave rise to mild irritation. Rats subjected to multiple intragastric administrations of tributyl phosphate; showed hyperemia of internal organs and brain. Tributyl phosphate; was not neurotoxic to rats, but induced paralysis in mice. Tributyl phosphate; did not cause organophosphorus compound-induced delayed neurotoxicity (OPIDN) in the adult hen. Tributyl phosphate; produced tumors of the bladder urothelium in rats at high doses, with greater effects in males than in females. It does not produce tumors in mice. The chemical was not teratogenic in rats. In the rabbit, maternal and embryo toxicity were suggested at 400 mg/kg/day with no observations of fetotoxicity or teratogenicity in any dosage group. No mutagenic activity was identified after treatment with tributyl phosphate;: when tested in the hypoxanthine;-guanine; phosphoribosyl transferase (HGPRT) mutation assay in Chinese hamster ovary (CHO) cells, both with and without metabolic activation and when testing in Salmonella typhimurium strains TA98, TA100, TA1535, or TA1537 with or without metabolic activations. Tributyl phosphate; did not induce chromosomal damage in rat bone marrow cells. ECOTOXICITY STUDIES: Rainbow trout treated with tributyl phosphate; had severe balance disturbances, which included highly atypical movements like darting, coiling swimming, and backward somersaults. At higher concentrations the fish were immobilized, lying on their sides at the bottom of the water;, and some of them died.

3. Use and Manufacturing

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

3.2 Environmental Fate: Biological. Indigenous microbes in Mississippi River water degraded tributyl phosphate tocarbon 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 theintermediates dibutyl phosphate and monobutyl phosphate (Thomas and Macaskie, 1996).

3.3 GHS Classification: Signal: Warning
GHS Hazard Statements
H302: Harmful if swallowed [Warning Acute toxicity, oral]
H315: Causes skin irritation [Warning Skin corrosion/irritation]
H351: Suspected of causing cancer [Warning Carcinogenicity]

Precautionary Statement Codes
P201, P202, P264, P270, P280, P281, P301+P312, P302+P352, P308+P313, P321, P330, P332+P313, P362, P405, and P501

3.4 Methods of Manufacturing: Prepared by reaction of POCL3 with butyl alcohol;.

3.5 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.

3.6 Produe Method: Prepared by the reaction of phosphorus oxychloride with butyl alcohol.

3.7 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.]

3.8 Usage: Tributyl phosphate (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.

3.9 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

4. Safety and Handling

4.1 Symbol: GHS07, GHS08

4.1 Hazard Codes: Xn,F

4.1 Signal Word: Warning

4.1 Risk Statements: 22-38-40-62-48/20-36/37/38-11-20/22

4.1 Safety Statements: 36/37-46-45-36/37/39-16-53

4.1 Exposure Standards and Regulations: Tributyl phosphate is an indirect food additive for use only as a component of adhesives.

4.2 Packing Group: I; II; III

4.2 Octanol/Water Partition Coefficient: log Kow = 4.00

4.3 Fire Hazard: Special Hazards of Combustion Products: Toxic fumes of PO x

4.4 Other Preventative Measures: SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
In order to handle industrial and commercial organic phosphites and phosphates, a careful evaluation should be undertaken to determine the precise effects of the individual phosphorus compound involved. Usually, all skin contact and inhalation of vapors or dusts should be avoided. All persons handling such materials should undergo regular medical examinations, with special stress on the central nervous system. /Esters of Organic Phosphorus Compounds/
Work clothing that becomes wet or significantly contaminated should be removed and replaced.
The worker should immediately wash skin when it become contaminated.
Avoidance of skin contact & inhalation of mist, dust, or vapor (esp if heated liq are handled) will usually be desirable... /Contaminated clothing removed & skin washed/. /Phosphate esters/
Being toxic, protect body against skin contact and inhalation.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

4.5 Hazard Class: 6.1

4.5 Hazard Declaration: H302-H315-H351-H412

4.5 Cleanup Methods: A study of nuclear fuel reprocessing solvent tributyl phosphate included its degradation and clean-up and disposal of degradation products.
Ventilate the area of spill or leak. For small quantities, absorb on paper towel .

4.6 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

4.7 RIDADR: UN 1208 3/PG 2

4.7 Fire Fighting Procedures: To fight fire use carbon dioxide, dry chemical, fog, mist.

4.8 FirePotential: Combustible when exposed to heat or flame.

4.9 Safety Profile: Poison byintraperitoneal and intravenous routes.Moderately toxic by ingestion, inhalation,and subcutaneous routes. Experimentalreproductive effects. A skin, eye, andmucous membrane irritant. Combustiblewhen exposed to heat or flame. To fightfire, use CO2, dry chemical, fog, mist. Whenheated to decomposition it emits toxicfumes of POx.

4.10 Caution Statement: P273-P301 + P312 + P330

4.10 Formulations/Preparations: Grade: Technical

4.11 WGK Germany: 2

4.11 RTECS: TC7700000

4.11 Protective Equipment and Clothing: Wear appropriate personnel protective clothing to prevent skin contact.
Wear appropriate eye protection to prevent eye contact.
Respirator Recommendations: Up to 2 ppm: (Assigned Protection Factor = 10) Any supplied-air respirator.
Respirator Recommendations: Up to 5 ppm: (Assigned Protection Factor = 25) Any supplied-air respirator operated in a continuous-flow mode.
Respirator Recommendations: Up to 10 ppm: (Assigned Protection Factor = 50) Any self-contained breathing apparatus with a full facepiece./(Assigned Protection Factor = 50) Any supplied-air respirator with a full facepiece.
Respirator Recommendations: Up to 30 ppm: (Assigned Protection Factor = 2000) Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode.
Respirator Recommendations: Emergency or planned entry into unknown concentrations or IDLH conditions: (Assigned Protection Factor = 10,000) Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode./(Assigned Protection Factor = 10,000) Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode in combination with an auxiliary self-contained positive-pressure breathing apparatus.
Respirator Recommendations: Escape: (Assigned Protection Factor = 50) Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister having an N100, R100, or P100 filter./Any appropriate escape-type, self-contained breathing apparatus.

4.12 Reactivities and Incompatibilities: Alkalis, oxidizers, water, moist air.

4.13 Report: Reported in EPA TSCA Inventory.

4.14 Skin, Eye, and Respiratory Irritations: Potential symptoms of overexposure are irritation of eyes, respiratory system and skin...
Breathing vapors of tributyl phosphate causes irritation of mucous membranes...

4.15 Safety: 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 PO_x.
Hazard Codes:?Xn,F
Risk Statements: 22-38-40-62-48/22-36/37/38-11
R22:Harmful if swallowed.?
R38:Irritating to skin.?
R40:Limited evidence of a carcinogenic effect.?
R62:Risk of impaired fertility.?
R48/22:Harmful: danger of serious damage to health by prolonged exposure if swallowed.?
R36/37/38:Irritating to eyes, respiratory system and skin.?
R11:Highly flammable.
Safety Statements: 36/37-46-45-36/37/39-16-53
S36/37:Wear suitable protective clothing and gloves.?
S46:If swallowed, seek medical advice immediately and show this container or label.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.?
S16:Keep away from sources of ignition.?
S53:Avoid exposure - obtain special instructions before use.
RIDADR: UN 1208 3/PG 2
WGK Germany: 2
RTECS: TC7700000
HS Code: 29190010

4.16 Specification: ? Tributyl phosphate , with CAS number of 126-73-8, can be called Tributilfosfato ; Celluphos 4 ; Butyl phosphate, tri- ; 1-dibutoxyphosphoryloxybutane ; Butyl phosphate ; Phosphoric acid tributyl ester ; tributyl ester ; Tributoxyphosphine oxide ; TBP Tributyl phosphate ; Tributyl phosphate (TBP)?. Tributyl phosphate (CAS NO.126-73-8) , known commonly as 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. Tributyl phosphate is used also in mercerizing liquids, where it improves their wetting properties. Tributyl phosphate 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.

4.17 Toxicity

1.	???	skn-rbt 10?mg/24H	???	JIHTAB ?? Journal of Industrial Hygiene and Toxicology. 26 (1944),269.
2.	???	eye-rbt 97?mg	???	AJOPAA ?? American Journal of Ophthalmology. 29 (1946),1363.
3.	???	orl-rat LD50:1390?mg/kg	???	JTSCDR ?? Journal of Toxicological Sciences. 5 (1980),270.
4.	???	ipr-rat LD50:251?mg/kg	???	GTPZAB ?? Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 15 (8)(1971),30.
5.	???	ivn-rat LDLo:100?mg/kg	???	NATUAS ?? Nature. 179 (1957),154.
6.	???	orl-mus LD50:1189?mg/kg	???	GTPZAB ?? Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 15 (8)(1971),30.
7.	???	ihl-mus LC50:1300?mg/m³	???	GTPZAB ?? Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 15 (8)(1971),30.
8.	???	ipr-mus LD50:159?mg/kg	???	GTPZAB ?? Gigiena Truda i Professionalnye Zabolevaniia. Labor Hygiene and Occupational Diseases. 15 (8)(1971),30.
9.	???	scu-mus LDLo:3?g/kg	???	EDWU** ?? Beitrag zur Toxikologie Technischer Weichmachungsmittel, Heinrich Eller Dissertation .(Pharmakologischen Institut der Universitat Wurzburg,Germany.:?1937).
10.	???	?

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin irritation, Category 2

Carcinogenicity, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H315 Causes skin irritation H351 Suspected of causing cancer
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

1H NMR : 400 MHz in CDCl3

IR : liquid film

Raman : 4880 A,200 M,liquid

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

126-73-8Total: 10 Synthesis Route

71-36-3 62 Suppliers

126-73-8 280 Suppliers

142-96-1 21 Suppliers

Literatures:
J. Gen. Chem. USSR (Engl. Transl.), , vol. 60, # 4.1 p. 837 - 840,736 - 742
Yield: null

71-36-3 62 Suppliers

1809-19-4 25 Suppliers

126-73-8 280 Suppliers

Literatures:
Russian Journal of General Chemistry, , vol. 65, # 4.1 p. 515 - 520 Zhurnal Obshchei Khimii, , vol. 65, # 4 p. 577 - 582
Yield: ~5%

71-36-3 62 Suppliers

126-73-8 280 Suppliers

109-69-3 145 Suppliers

142-96-1 21 Suppliers

Literatures:
Dorfman, Ya. A.; Levina, L. V.; Petrova, T. V.; Aleshkova, M. M.; Abdreimova, R. R.; et al. J. Gen. Chem. USSR (Engl. Transl.), 1990 , vol. 60, # 6 p. 1275 - 1282,1137 - 1144
Yield: null

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8. Other Information

8.0 Usage: Tri-n-butyl phosphate is used as a solvent for rare earth metals exaction and purification, and as a flame retardant component of aircraft hydraulic fluid. It is involved in the formation of stable hydrophobic complexes with some metals. It is also employed as a defoamer additive in cement casings for oil wells, as an anti-air entrainment additive for coatings and floor finishes and as a solvent in nuclear fuel processing. Further, it is used as a solvent in inks, synthetic resins, gums and adhesives. In addition, it is used as a plasticizer for cellulose esters like nitrocellulose and cellulose acetate.

8.1 Merck: 14,9618

8.2 BRN: 1710584

8.3 职业标准: TWA 5 mg/m3;STEL 5 mg/m3

8.4 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.

Tributyl phosphate (TBP) is an organophosphorus compound widely used as a solvent in nuclear fuel reprocessing for the extraction of uranium and plutonium from other radionuclides.
The major uses of tributyl phosphate (TBP) in industry are as a flame retardant 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, as an anti-air entrainment additive for coatings and floor finishes, as a solvent in nuclear fuel processing, and as a carrier for fluorescent dyes.
The microbial degradation of tributyl phosphate was carried out using Klebsiella pneumoniae S3 isolated from the soil. The solubilization behavior of TBP in aqueous solutions of L64-Pluronics was studied using light and small angle neutron scattering (SANS).

8.5 Uses: Tributyl phosphate (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.

8.6 Preparation: Tributyl phosphate is manufactured by reaction of phosphoryl chloride with n-butanol.
A 1-liter four-necked flask is fitted with an efficient condenser, an air-tight stirrer, a short-stemmed dropping funnel and a thermometer. Calcium chloride tubes are attached to the top of dropping funnel and the reflux condenser. 137 ml (111 g) of dry n-butyl alcohol, 132.5 ml (130 g) of dry pyridine and 140 ml of dry benzene are placed in the flask, which is stirred and cooled in an ice-salt mixture until the temperature falls to – 5° C. 40.5 ml (76.5 g) of freshly redistilled (b.p. 106-107° C) phosphorus oxychloride are dropwise added from the funnel at such a rate that the temperature does not rise above 10° C. When all phosphorus oxychloride has been added the reaction mixture is gently refluxed for 2 hours and cooled to room temperature. 250 ml of water are added in order to dissolve the pyridine hydrochloride, the benzene layer is separated, washed several times with water until the washings are neutral, and dried over anhydrous sodium or magnesium sulfate. The benzene is removed by evaporation and crude tributyl phosphate is purified by distillation in a vacuum. The fraction boiling at 160-162°/15 mm or 138-140°/6 mm is collected yielding 95 g of pure tributyl phosphate.

8.7 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.

8.8 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.

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

8.10 Physical properties: Clear, colorless to pale yellow, odorless, slightly flammable, oily liquid

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

8.12 Uses: Plasticizer for cellulose esters, lacquers, plastics, and vinyl resins.

8.13 Uses: Tributyl phosphate is used as an antifoaming agent; plasticizer for cellulose esters, lacquers, plastic, and vinyl resins; component in hydraulic fluids for aircraft control systems.

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

8.15 Production Methods: Prepared by the reaction of phosphorus oxychloride with butyl alcohol.

8.16 General Description: Tributyl phosphate is an organophosphorus compound, which is widely used as a flame retardant and plasticizer in a variety of industrial products.

9. Computational chemical data

Molecular Weight: 266.31g/mol
Molecular Formula: C₁₂H₂₇O₄P
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 266.16469634
Monoisotopic Mass: 266.16469634
Complexity: 175
Rotatable Bond Count: 12
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 44.8
Heavy Atom Count: 17
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceBwOAIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAAACAACACggAICAAAAARAAQAAAAIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAEAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10. Question & Answer

What is Tributyl phosphate? Mar 23 2020
Tributyl phosphate (TBP, C12H27O4P, CAS registry No. 126-73-8) is an odorless colorless to yellow liquid. Its melting point is -79 oC, and boiling point is 289 oC. The solubility of TBP is only 280 mg/L in water at 25 oC. It is soluble in diethyl ether, benzene, carbon disulfide. It can be miscible...

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Tributyl phosphate 99%min. TBP CAS NO 126-73-8

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Tributyl phosphate