126-73-8 Usage
Uses
Used in Nuclear Processing:
Tributyl phosphate is used as a solvent for the extraction and purification of rare earth metals, such as uranium and plutonium, from their ores.
Used in Aircraft Hydraulic Fluids:
TBP is used as a component of aircraft hydraulic fluid, providing essential properties for the fluid's performance.
Used in Plastics and Coatings Industry:
Tributyl phosphate is used as a plasticizer for cellulose esters, lacquers, plastics, and vinyl resins, enhancing their flexibility and workability.
Used in Mercerizing Liquids:
TBP is used in mercerizing liquids to improve their wetting properties, which is important in the textile industry for treating cotton fibers.
Used as a Heat Exchange Medium:
TBP serves as a heat exchange medium and dielectric in various industrial processes.
Used in Consumer Products:
Tributyl phosphate is used in some consumer products such as herbicides, water-thinned paints, and tinting bases.
Used as an Antifoaming Agent:
TBP is used as an antifoaming agent in various industrial applications to control foam formation.
Used in Cement Casing for Oil Wells:
TBP is used as a defoamer additive in cement casings for oil wells, preventing the formation of air bubbles in the cement.
Used as an Anti-Air Entrainment Additive:
TBP is used as an anti-air entrainment additive for coatings and floor finishes, improving the quality and performance of these products.
Used as a Carrier for Fluorescent Dyes:
TBP serves as a carrier for fluorescent dyes, enabling their effective application in various industries.
Used in the Extraction of Heavy Metals:
TBP acts as a complexing agent in the extraction of heavy metals, particularly in the extraction of metal ions from solutions of reactor products in nuclear fuel reprocessing.
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.
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.
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
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..
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.
Carcinogenicity
TBP was not genotoxic in a variety of
in vivo and in vitro assays.7 It has been suggested
that the carcinogenic effects of TBP are
species- and organ specific. The necrotic
actions of TBP (or a metabolite) on rat urinary
bladder epithelium may induce chronic repair
processes that cause the normal epithelium to
be transformed into its metaplastic and neoplastic
forms.
TBP was not teratogenic when administered
to rats and rabbits during gestation;
fetotoxic effects (delayed ossification and reduced
fetal body weights) occurred in rats at
doses that caused severe maternal toxicity.
There was no evidence of reproductive toxicity
or reproductive organ pathology in twogeneration
studies in rats fed TBP in the diet.
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).
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.
Check Digit Verification of cas no
The CAS Registry Mumber 126-73-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 6 respectively; the second part has 2 digits, 7 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 126-73:
(5*1)+(4*2)+(3*6)+(2*7)+(1*3)=48
48 % 10 = 8
So 126-73-8 is a valid CAS Registry Number.
InChI:InChI=1/C12H27O4P/c1-4-7-10-14-17(13,15-11-8-5-2)16-12-9-6-3/h4-12H2,1-3H3
126-73-8Relevant articles and documents
Cu-catalyzed oxidative phosphorylation of alkanols with white phosphorus and H2O2
Trofimov, Boris,Timokhin, Boris,Gusarova, Nina,Kazantseva, Marina,Golubin, Alexander
, p. 2385 - 2390 (2002)
Oxidative phosphorylation of alkanols with white phosphorus in the presence of catalytic amounts of CuCl2 has been effected. The reaction proceeds in the aqueous H2O2-HCl system exothermically to form dialkylphosphites and trialkylphosphates in a total yield of up to 35%. Conditions for selective synthesis of dialkylphosphites in moderate yield have been found.
Catalytic method of synthesis of phosphorus acids esters from zinc phosphide and alcohol
Polimbetova,Ibraimova,Borangazieva
, p. 1081 - 1086 (2013)
Ecologically safe effective catalytic method for preparing phosphorous and phosphoric acid esters by oxidation of zinc phosphide with oxygen in the solution of copper(II) halides in butanol at 50-70 C is developed. It is found that in the presence of Cu(II) chloride a mixture of dibutyl hydrogen phosphite and tributyl phosphate is formed, while at the catalysis with Cu(II) bromide tributyl phosphate is mainly obtained. Promoting action of hydrogen chloride on the reaction rate and yield of organophosphorus compounds is established. Optimal reaction conditions are found and redox mechanism of catalytic process is assumed.
Phosphadioxirane Intermediates in the Reaction of Singlet Oxygen with Phosphites and Phosphines
Tsuji, Shoei,Kondo, Masaaki,Ishiguro, Katsuya,Sawaki, Yasuhiko
, p. 5055 - 5059 (1993)
Intermediates in the singlet oxygen reaction of phosphites and phosphines have been studied by trapping and tracer experiments.Trapping study with diphenyl sulfoxide revealed that the added substrate and phosphite are competing toward the same intermediate.The relative reactivity of (BuO)3P/Ph2S/Ph2SO = 300:4:1 and the negative ρ-value of -0.63 for diphenyl sulfoxides are not consistent with 1,3-dipolar phosphine peroxides, but suggest electrophilic O-transfers by cyclic phosphadioxiranes.Intermediacy of phosphadioxiranes was supported by an 18O-tracer study on the formation of rearranged diphenylphosphinate from 1O2 and triphenylphosphine.Theoretical calculations also supported the dioxirane intermediate by predicting no existence of 1,3-dipolar peroxide.
Oxidizing alkoxylation of phosphine in alcoholic solutions of iodine
Polimbetova,Borangazieva
, p. 2079 - 2082 (2001)
Oxidizing alkoxylation of PH3 to trialkyl phosphates was performed in pyridine-alcoholic solutions of iodine. The optimal conditions of the reaction were found.
Utilization of Oxidizing Character of TeCl4 in the Reaction with Trialkyl Phosphite. A Novel Redox Phosphorylation
Watanabe, Yutaka,Yamamoto, Takashi,Iwasaki, Taroh,Ozaki, Shoichiro
, p. 1881 - 1884 (1994)
Oxidation-reduction reaction of a trialkyl phosphite with TeCl4 in the presence of an alcohol and tert-amine proceeded smoothly to afford the corresponding phosphorylation product in good yield.
ELECTROCHEMICALLY INDUCED PROCESSES IN THE FORMATION OF PHOSPHORUS ACID DERIVATIVES. 1. SYNTHESIS OF TRIALKYL PHOSPHATES FROM WHITE PHOSPHORUS
Romakhin, A. S.,Budnikova, Yu. G.,Zaripov, I. M.,Kargin, Yu. M.,Nikitin, E. V.,et al.
, p. 1031 - 1035 (1992)
An electrochemical method, based on the joint action of nucleophilic and electrophilic reagents on P4, is proposed in order to utilize white phosphorus in the formation of the esters of phosphorus acids.The action of alkoxide ions on white phosphorus in an alcohol medium in the presence of iodine generated at the anode leads to the formation of phosphate esters.A scheme in which the intermediate products are dialkyl and trialkyl phosphites and the side product is dialkyl alkylphosphonate is proposed for the process.Key words: Phosphate esters, white phosphorus, electrosynthesis.
Oxidation of phosphine with quinone and quinoid redox polymers in alcohol solutions of copper
Polimbetova,Mukhitdinova,Ergozhin,Borangazieva,Khakimbolatova, K. Kh.,Tasmagambet,Dauletkulova,Ibraimova, Zh. U.
, p. 2344 - 2349 (2017)
New quinoid redox polymers were obtained by chemical modification of commercial weakly basic anion exchangers with quinone and its derivatives. The redox properties of quinone and quinoid redoxites with respect to phosphine were studied in alcohol solutions of copper complexes.
Synthesis of mixed alkylphosphites and alkylphosphates
Ilia, Gheorghe,Popa, Adriana,Iliescu, Smaranda,Bora, Alina,Dehelean, Gheorghe,Pascariu, Aurelia
, p. 1513 - 1519 (2003)
Some mixed phosphites having two different alkyl chain were obtained as forerunners for mixed phosphates Mixed dialkyl phosphates were obtained in good yields (40-80%) by phase transfer catalysis in liquid-liquid sistem, starting from different dialkyl phosphites and aliphatic alcohols. The reaction conditions were optimized in order to obtain good yields in phosphites and phosphates respectively. Compounds were analyzed by IR, P31-NMR.
METHOD FOR PRODUCING PHOSPHOESTER COMPOUND
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Paragraph 0023; 0026-0028, (2021/09/27)
PROBLEM TO BE SOLVED: To provide a method whereby, a phosphate compound selected from the group consisting of orthophosphoric acid, phosphonic acid, phosphinic acid, and anhydrides of them is used as raw material and, by one stage reaction, a corresponding phosphoester compound is produced. SOLUTION: To an aqueous solution of a phosphate compound, added is an organic silane or siloxane compound having an alkoxy group or an aryloxy group, and the mixture is subjected to a heating reaction, thereby producing a corresponding phosphoester compound without requiring a catalyst. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT
Hydrophosphonylation of Alkynes with Trialkyl Phosphites Catalyzed by Nickel
Islas, Rosa E.,García, Juventino J.
, p. 4125 - 4131 (2017/10/09)
The use of simple and inexpensive NiCl2?6 H2O as a catalyst precursor for C?P bond formation in the presence of commercially available trialkyl phosphites (P(OR)3, R=Et, iPr, Bu, SiMe3) along with several alkynes is presented. Control experiments showed the in situ formation of (RO)2P(O)H as the species that undergo the addition into the C≡C bond at the alkynes to yield the product of P?H addition. The hydrophosphonylation of diphenylacetylene with P(OEt)3, P(OiPr)3, and P(OSiMe3)3 proceeds in high yields (>92 %) without the need of a specific solvent or ligand. This method is useful for the preparation of organophosphonates for both phenylacetylene as a terminal alkyne model and internal alkynes in yields that range from good to modest.
