Tributyl phosphate

Base Information

• Chemical Name: Tributyl phosphate
• CAS No.: 126-73-8
• Deprecated CAS: 15158-85-7,19824-61-4,80094-39-9,1238174-19-0,329184-61-4,1238174-19-0,19824-61-4,80094-39-9
• Molecular Formula: C12H27O4P
• Molecular Weight: 266.318
• Hs Code.: 29190010
• European Community (EC) Number: 204-800-2
• ICSC Number: 0584
• NSC Number: 8484
• UNII: 95UAS8YAF5
• DSSTox Substance ID: DTXSID3021986
• Nikkaji Number: J3.623D
• Wikipedia: Tributyl_phosphate
• Wikidata: Q613394
• NCI Thesaurus Code: C1259
• RXCUI: 1314418
• Metabolomics Workbench ID: 55063
• ChEMBL ID: CHEMBL1371096
• Mol file: 126-73-8.mol

Synonyms:TBP;tri-(n-butyl )-phosphate;tri-n-butyl phosphate;tri-n-butylphosphate;tributyl phosphate;tributylphosphate

Chemical Property of Tributyl phosphate

Chemical Property:

• Appearance/Colour: clear liquid
• Vapor Pressure: 27 mm Hg ( 178 °C)
• Melting Point: -79 °C
• Refractive Index: n20/D 1.424(lit.)
• Boiling Point: 288.3 °C at 760 mmHg
• Flash Point: 193.3 °C
• PSA: 54.57000
• Density: 0.986 g/cm³
• LogP: 4.54460
• Storage Temp.: Store below +30°C.
• Solubility.: water: soluble1ml in 165ml water
• Water Solubility.: 0.6 g/100 mL
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 12
• Exact Mass: 266.16469634
• Heavy Atom Count: 17
• Complexity: 175

Purity/Quality:

98% ^*data from raw suppliers

PhosphoricAcidTributylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,F
• Hazard Codes: Xn,F
• Statements: 22-38-40-62-48/20-36/37/38-11-20/22
• Safety Statements: 36/37-46-45-36/37/39-16-53

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organophosphates, Other
• Canonical SMILES: CCCCOP(=O)(OCCCC)OCCCC
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
• Effects of Short Term Exposure: The substance is severely irritating to the eyes, skin and respiratory tract.
• Effects of Long Term Exposure: Ingestion may cause effects on the bladder. This may result in tissue lesions.
• 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. Tributyl phosphate is used as a plasticizer for cellulose esters, vinyl resins, and lacquers; and in making fireretardants, biocides, defoamers, and catalysts. Plasticizer for cellulose esters, lacquers, plastics, and vinyl resins. 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.
• 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.
• Physical properties: Clear, colorless to pale yellow, odorless, slightly flammable, oily liquid

Technology Process of Tributyl phosphate

There total 54 articles about Tributyl phosphate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

butan-1-ol (71-36-3) → phosphoric acid tributyl ester (126-73-8) + n-Butyl chloride (109-69-3)

Guidance literature:

With hydrogenchloride; water; oxygen; copper dichloride; at 59.9 ℃; Product distribution; Mechanism; other alcohols, var. conc. of reagents, var. temperat.;

Reference yield: 100.0%

butan-1-ol (71-36-3) → phosphoric acid tributyl ester (126-73-8)

Guidance literature:

With oxygen; phosphan; copper dichloride; at 24.9 ℃; Rate constant; Product distribution; other acohols and reagents, var. concentration of reagents and temperatures;

Reference yield: 98.0%

sodium butanolate (2372-45-4) → phosphoric acid tributyl ester (126-73-8)

Guidance literature:

With trichlorophosphate; In butan-1-ol; at 10 - 30 ℃; for 1.83333h;

upstream raw materials:

tri-n-butyl phosphite

sodium butanolate

aluminum tri-n-butoxide

dibutyl phosphate

Downstream raw materials:

n-butyl phenyl ether

N,N,N',N'-tetrabutylhexane-1,6-diamine

1,1-diphenylpentane

N,N-dibutyl-4-methylaniline

Refernces

• 1、 Trofimov, Boris,Timokhin, Boris,Gusarova, Nina,Kazantseva, Marina,Golubin, Alexander. "Cu-catalyzed oxidative phosphorylation of alkanols with white phosphorus and H2O2". . p. 2385 - 2390. Retrieved 2002.
• 2、 Kochetkov et al.. "". . . Retrieved 1972.
• 3、 Polimbetova,Ibraimova,Borangazieva. "Catalytic method of synthesis of phosphorus acids esters from zinc phosphide and alcohol". . p. 1081 - 1086. Retrieved 2013.
• 4、 Polimbetova,Borangazieva. "Oxidizing alkoxylation of phosphine in alcoholic solutions of iodine". . p. 2079 - 2082. Retrieved 2001.
• 5、 Romakhin, A. S.,Budnikova, Yu. G.,Zaripov, I. M.,Kargin, Yu. M.,Nikitin, E. V.,et al.. "ELECTROCHEMICALLY INDUCED PROCESSES IN THE FORMATION OF PHOSPHORUS ACID DERIVATIVES. 1. SYNTHESIS OF TRIALKYL PHOSPHATES FROM WHITE PHOSPHORUS". . p. 1031 - 1035. Retrieved 1992.
• 6、 Gilyarov et al.. "". . . Retrieved 1974.
• 7、 -. "METHOD FOR PRODUCING PHOSPHOESTER COMPOUND". Paragraph 0023; 0026-0028. . Retrieved 2021/09/27.
• 8、 -. "Method of synthesizing alkyl phosphate". Paragraph 0033; 0034. . Retrieved 2017/01/02.