126-71-6

Basic information

• Product Name: Triisobutyl phosphate
• Synonyms: PHOSPHORIC ACID TRIISOBUTYL ESTER;isobutylphosphate;Phosphoricacid,tris(2-methylpropyl)ester;TRIISOBUTYL PHOSPHATE;TIBP;TRIS-ISOBUTYLPHOSPHATE;Triisobutylphosphat;Tris(2-methylpropyl) phosphate
• CAS NO: 126-71-6
• Molecular Formula: C₁₂H₂₇O₄P
• Molecular Weight: 266.31
• EINECS: 204-798-3
• Product Categories: Extracting agent;Other
• Mol File: 126-71-6.mol

Chemical Properties

• Boiling Point: ~205 °C(lit.)
• Flash Point: 150 °C
• Appearance: Colorless transparent liquid
• Density: 0.965 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0191mmHg at 25°C
• Refractive Index: n20/D 1.420
• Storage Temp.: Store below +30°C.
• Solubility: 0.26g/l
• Water Solubility: 264mg/L at 25℃
• CAS DataBase Reference: Triisobutyl phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: Triisobutyl phosphate(126-71-6)
• EPA Substance Registry System: Triisobutyl phosphate(126-71-6)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• WGK Germany: 1
• RTECS: TC9300000
• Hazardous Substances Data: 126-71-6(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 126-71-6 differently. You can refer to the following data:
1. Phosphate esters are used as flame retardants, plasticizers, hydraulic fluids, solvents, extraction agents, antifoam agents, Partition behavior in water, sediment, and soil Phosphate ester flame retardants enter the environment from industrial sources and disposal of consumer products containing flame retardants. These anthropogenic compounds have been detected in water, soil, and air owing to widespread use following their fast emergence and popularization during 1970s. Occurrence of these phosphate ester flame retardants is widespread in surface water and groundwater because of the leaching of PVC plastics and polyurethane foams, effluent from industrial sources, and spills of hydraulic fluids. This primary contaminated water is then transported to a secondary source, such as drinking water. Hydrolysis, although slow because of poor solubility and pH dependence, is the most important abiotic elimination process. In soil and sediment, phosphate ester flame retardants are persistent because they have the tendency to adsorb strongly. Volatilization and biodegradation are potential elimination processes for phosphate esters adsorbed to soil. Environmental persistency (degradation/speciation) These retardants can change chemical composition in the environment. Generally, most phosphate esters are poorly soluble in water and adsorb strongly to soils. These compounds are considered emerging pollutants because of their prevalence and persistence in the environment. Particulate-phase phosphate esters are subject to wet and dry deposition, whereas semi-volatile phosphate esters have the potential to hydrolyze to diesters, monoesters, and phosphoric acid. There is no information available that suggests that selected phosphate ester flame retardants undergo transformation or degradation in the atmosphere. Long-range transport This is highly dependent on the specific compound. Bioaccumulation and biomagnification Phosphate esters are subject to biodegradation in aquatic and terrestrial environments.
2. Phosphoric Acid Tris(2-?methylpropyl) Ester is found in the groundwater downgradient of a landfill (Grindsted, Denmark). It is also a flame retardant and plasticizer.

Flammability and Explosibility

Notclassified

Environmental Fate

Routes and pathways relevant physicochemical properties (e.g., solubility, Pow, Henry constant.)consumer and industrial items and play an important role in safeguarding life and property. A large and diverse group of anthropogenic compounds constitute flame retardants, which are added to combustible materials to render them more resistant to ignition. They are designed to minimize the risk of a fire in the event of contact with a small heat source such as a cigarette. A wide range of different flame retardants is produced, because many materials and products that are to be rendered fire safe are very different in nature and composition. Therefore, having variety in flame retardant products is necessary so as to retain key material functionality. For example, plastics have a wide range of mechanical and chemical properties and differ in combustion behavior. These materials in particular are the main focus of phosphate ester flame retardants.Phosphate esters are derivatives of tri protic acid, phosphoric acid, with a general formula of RxH3°xPO4. Flame retardants are composed of a group of chemicals with similar properties but slightly different structures. They are typically liquids and some are solids at room temperature. Some examples of the phosphate ester flame retardants include: tris(2-chloroethyl)phosphate (TCEP), tributyl phosphate (TnBP), tris(2-butoxyethyl) phosphate (TBEP), tris(1,3-dichloro-2-propyl) phosphate (TDCP), triphenyl phosphate (TPP), tris(2-chloro-isopropyl) phosphate (TCPP), and triisobutyl phosphate (TiBP). These compounds are trisubstituted and categorized as alkyl (TnBP, TiBP), alkyl ether (TBEP), chloroalkyl (TCEP, TCPP, TDCP), and aryl (TPP) phosphate esters.

Purification Methods

Purify it by repeated crystallisation, from hexane, of its addition compound with uranyl nitrate. (see tributyl phosphate.) [Siddall J Am Chem Soc 81 4176 1959; see Cherbuliez in Organo Phosphorus Compounds (Kosolapoff & Maier eds) Wiley Vol 6 pp 211-577 1973.]

InChI:InChI=1/C12H27O4P/c1-10(2)7-14-17(13,15-8-11(3)4)16-9-12(5)6/h10-12H,7-9H2,1-6H3

Synthetic route

2-methyl-propan-1-ol (78-83-1) → triisobutyl phosphate (126-71-6) + diphosphoric acid tetraisobutyl ester (3846-81-9)

Conditions	Yield
With phosphorous; tetraethylammonium iodide In water at 50℃; Electrolysis;	A 4% B 81%

2-methyl-propan-1-ol (78-83-1) → diisobutyl phosphite (1189-24-8) + diisobutyl phosphoric acid (6303-30-6) + triisobutyl phosphate (126-71-6)

Conditions	Yield
With sodium hypophosphite; copper dichloride at 24.9℃; for 148h;	A 5.6% B 66.6% C 27.8%

2-methyl-propan-1-ol (78-83-1) → triisobutyl phosphate (126-71-6)

Conditions	Yield
With pyridine; trichlorophosphate; benzene
With argon; phosphan; copper(l) chloride; copper dichloride In acetonitrile
With argon; phosphan; copper(l) chloride; copper dichloride In acetonitrile at 24.9℃; Rate constant; Thermodynamic data; Product distribution; E(excit.), ΔS(excit.);

sodium isobutoxide (13259-29-5) → triisobutyl phosphate (126-71-6)

Conditions	Yield
With diethyl ether; trichlorophosphate
With phosphorus trichloride

triisobutyl phosphite (1606-96-8) → triisobutyl phosphate (126-71-6)

Conditions	Yield
With 2-methyl-propan-1-ol; chlorine

triisobutyl phosphite (1606-96-8) → triisobutyl phosphate (126-71-6) + diphosphoric acid tetraisobutyl ester (3846-81-9)

Conditions	Yield
With iodoacetophenone; silver perchlorate In benzene for 0.316667h; Title compound not separated from byproducts;

phosphorochloridic acid diisobutyl ester (17158-87-1) + 2-methyl-propan-1-ol (78-83-1) → triisobutyl phosphate (126-71-6)

Conditions	Yield
at 60℃; Rate constant; Thermodynamic data; activation energy, activation enthalpy, other temperature (40, 50, 70, 80 deg C);

2-methyl-propan-1-ol (78-83-1) → triisobutyl phosphate (126-71-6) + diisobutyl ether (628-55-7)

Conditions	Yield
With phosphan; copper dichloride In N,N-dimethyl-formamide at 59.9℃;

2-methyl-propan-1-ol (78-83-1) → triisobutyl phosphate (126-71-6) + isobutyryl chloride (513-36-0)

Conditions	Yield
With phosphan; chlorine at 20℃; Rate constant; Thermodynamic data; Ea, ΔS(excit.); var. temp.; also in the presence of pyridine;

phosphonic acid diisobutyl ester (13529-77-6) → triisobutyl phosphate (126-71-6) + diphosphorus (IV)-oic acid tetraisobutyl ester (75340-94-2) + diphosphoric acid tetraisobutyl ester (3846-81-9)

Conditions	Yield
With sodium perchlorate In acetonitrile electrochemical oxidation, 2.4 A h; Pt anode, Ni cathode; Ag/AgNO3 reference electrode; Title compound not separated from byproducts;

hydrogenchloride (7647-01-0) + zinc(II) phosphide + 2-methyl-propan-1-ol (78-83-1) + oxygen (80937-33-3) → diisobutyl phosphoric acid (6303-30-6) + triisobutyl phosphate (126-71-6) + isobutyryl chloride (513-36-0) + zinc(II) chloride (7646-85-7)

Conditions	Yield
copper dichloride In further solvent(s) Kinetics;

copper phosphide + 2-methyl-propan-1-ol (78-83-1) → triisobutyl phosphate (126-71-6) + isobutyryl chloride (513-36-0) + copper dichloride

Conditions	Yield
With O2; CuCl2 In neat (no solvent) Kinetics; byproducts: H2O, HCl; the alcohol was loaded together with CuCl2 into the reactor and purged with an Ar-O2 mixture; then Cu3P was added and the mixt. reacted at 293 K, 323 K or 343 K;;

n-butyllithium (109-72-8, 29786-93-4) + triisobutyl phosphate (126-71-6) → diisobutyl butylphosphonate (10092-77-0)

Conditions	Yield
In tetrahydrofuran; hexane at -78 - 0℃;	93%

triisobutyl phosphate (126-71-6) + uranium(IV) perrhenate pentahydrate → [U(perrhenato)4(tri-iso-butyl phosphate)4]

Conditions	Yield
In acetonitrile (N2 or Ar); ligand added to a soln. of U salt; crystd. overnight at room temp.; elem. anal.;	87%

triisobutyl phosphate (126-71-6) + (232)thorium perrhenate*4H2O → [(232)Th(perrhenato)4(triisobutylphosphate)4]

Conditions	Yield
In methanol addn. of phosphorus compd. to a soln. of thorium compd. in methanol; centrifugation, sepn., washing ppt. with methanol, centrifugation, sepn., evapn. of supernatant, drying in vac., dissolving in methanol, filtration, keeping at 4°C for 3 d; elem. anal.;	75%

UO2(2+)*2ReO4(1-)*H2O=[UO2(ReO4)2(H2O)] + triisobutyl phosphate (126-71-6) → [UO2(ReO4)2(H2O)(tri-iso-butylphosphate)2] + bis[(μ2-perrhenato)(perrhenato)bis(tri-iso-butylphosphate)dioxouranium(VI)]

Conditions	Yield
In ethanol soln. of P ligand (2 equiv.) in EtOH was added dropwise to soln. of U compd. in EtOH; evapd.; crystd. (hexane, away from direct sunlight); filtered; dried in air; elem. anal.;	A n/a B 70%

chloral hydrate (302-17-0) + triisobutyl phosphate (126-71-6) → (2,2,2-trichloro-1-hydroxy-ethyl)-phosphonic acid diisobutyl ester (38457-66-8)

Conditions	Yield
In hexane Heating;	60%

europium(III) chloride hexahydrate + triisobutyl phosphate (126-71-6) + 1,2,4,5-benzenetetracarboxylic acid (89-05-4) → Eu4(PM)3*3H2O*TIBP3

Conditions	Yield
In ethanol; water To an aqueous soln. of EuCl3*6H2O was added an ethanolic soln. of pyromellitic acid and triisobutyl phosphate, neutralization with NH3 to pH 6 and warming to 30°C for 30-40 min.; Elem. anal.;	55%

UO2(2+)*2ReO4(1-)*H2O=[UO2(ReO4)2(H2O)] + triisobutyl phosphate (126-71-6) → [U(perrhenato)4(tri-iso-butyl phosphate)4]

Conditions	Yield
In ethanol Irradiation (UV/VIS); allowed to evap. slowly in direct sunlight; decanted; elem. anal.;	35%

triisobutyl phosphate (126-71-6) + 1-amino-naphthalene (134-32-7) → diisobutyl-[1]naphthyl-amine (109556-56-1)

triisobutyl phosphate (126-71-6) + naphthalen-2-ylamine (91-59-8) → diisobutyl-[2]naphthyl-amine (109554-95-2)

triisobutyl phosphate (126-71-6) + 9-Phenylfluorene (789-24-2) → 9-Isobutyl-9-phenyl-fluoren (102889-20-3)

Conditions	Yield
Multistep reaction;

n-butyllithium (109-72-8, 29786-93-4) + triisobutyl phosphate (126-71-6) → C12H26LiO3P

Conditions	Yield
In diethyl ether at 0℃; Yield given;
In tetrahydrofuran; hexane at -78 - 0℃;

triisobutyl phosphate (126-71-6) → tris(2-methyl-1-propyl) phosphate radical (83561-06-2)

Conditions	Yield
In water at 18.9℃; pulse radiolysis, pH 4.5-5; fast hydrolysis of alkyl radicals radiolytically formed;

triisobutyl phosphate (126-71-6) → Phosphorsaeure-sec.-butylester (2466-73-1) + diisobutyl phosphoric acid (6303-30-6)

Conditions	Yield
With sodium hydroxide In methanol; water at 100℃; for 2h; Title compound not separated from byproducts.;

triisobutyl phosphate (126-71-6) → diisobutyl (1-methylbutyl)phosphonate (112292-29-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran; hexane / -78 - 0 °C 2: 89 percent / tetrahydrofuran; hexane / -78 - -20 °C View Scheme
Multi-step reaction with 2 steps 1: diethyl ether / 0 °C 2: 83 percent View Scheme

triisobutyl phosphate (126-71-6) → diisobutyl butylphosphonate (10092-77-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether / 0 °C 2: 73 percent / H3O(1+) View Scheme

4-chloro-1H-isoindole-1,3(2H)-dione (51108-30-6) + 3-chlorophthalic anhydride (117-21-5) + triisobutyl phosphate (126-71-6) + aminosulfonic acid (5329-14-6) → 5-Chloroisatoic anhydride (4743-17-3) + 8-chloro-2H-benzo[d][1,3]oxazine-2,4(1H)-dione (63497-60-9)

Conditions	Yield
In water; formamide

Upstream product

• 78-83-1 2-methyl-propan-1-ol 
• 13259-29-5 sodium isobutoxide 
• 1606-96-8 triisobutyl phosphite 
• 17158-87-1 phosphorochloridic acid diisobutyl ester 
• 13529-77-6 phosphonic acid diisobutyl ester 
• 7647-01-0 hydrogenchloride 
• 80937-33-3 oxygen 
• 12019-57-7 copper phosphide 

Downstream Products

• 102889-20-3 9-Isobutyl-9-phenyl-fluoren 
• 2466-73-1 Phosphorsaeure-sec.-butylester 
• 6303-30-6 diisobutyl phosphoric acid 
• 4743-17-3 5-Chloroisatoic anhydride 
• 63497-60-9 8-chloro-2H-benzo[d][1,3]oxazine-2,4(1H)-dione 
• 5749-75-7 B-tris(di-i-butoxy phosphoryl) borazine 

Relevant articles and documents

Absolute viscosity and density of trisubstituted phosphoric esters

This paper presents measurements on the absolute viscosity (η) and density (ρ) of trisubstituted phosphoric esters which are useful in understanding their flow mechanism necessary for accessing their role as plasticizers. The effect of chain length and branching has been examined on the η and ρ trends. From η data, by using the Vogel-Tammann-Fulchur (VTF) equation, the VTF temperature (To) has been obtained which also represents the ideal glass transition temperature. To is related to the flexibility of the molecules. It is observed that To initially decreases with molecular weight, reaches a minimum, and increases thereafter. The initial decrease in To has been attributed to the enhanced flexibility of the phosphate esters. Reversal of flexibility with relative molar mass beyond 400 is due to the gentle collision of the arms of the trisubstituted phosphoric esters. This has been further corroborated from the molar mass exponent as exhibited in the η-molar mass plot. The isomeric effect on η has also been investigated in tricresyl phosphates, hitherto for the first time. The ortho isomer has highest η among the isomers. The para isomer was found to have lowest To and hence highest flexibility compared to the ortho and meta isomers.

Trends in small angle neutron scattering of actinide-trialkyl phosphate complexes: A molecular insight into third phase formation

The "third phase" formation phenomenon in solvent extraction is due to the aggregation of extracted species and formation of reverse micelles. As Small Angle Neutron Scattering (SANS) is a powerful tool to probe colloidal particles, it is considered as an important technique to study the aggregation behaviour of actinide complexes in solvent extraction systems. The actinide specific trialkyl phosphate (TalP) based extractants, namely, tri-n-butyl phosphate (TBP), tri-iso-butyl phosphate (TiBP), tri-sec-butyl phosphate (TsBP) and tri-sec-amyl phosphate (TsAP) have been examined for the first time using the SANS technique to investigate third phase formation phenomena with some of the actinides. SANS was employed to get insight into third phase formation in the extraction of Th(iv) and U(vi) from 1 M HNO3 by 1.1 M solutions of TalP in deuterated dodecane (n-C12D26, 98 atom% D). Deuterated diluent was used in order to provide contrast during the neutron scattering measurements. Potential energy and the stickiness parameter of reverse micelles formed in the above solvent systems have been quantified as a function of organic metal loading. The data are fitted using Baxter's sticky-sphere model. The stickiness parameter, (τ-1) a measure of the attractive interaction between the micelles, as well as the attractive potential energy (U0) was quantified. A clear correlation has been established between the stickiness parameter and the tendency for third phase formation with TalP systems. As U(vi) does not form a third phase with these extractants at 1 M HNO3, comparative studies were carried out with U(vi)-TalP complexes. These studies established lower stickiness and attraction between the micelles with the U(vi) system. The correlation between SANS parameters and third phase formation tendency was extended to a temperature dependence study and these studies established higher third phase limits when the temperature was enhanced, corroborating well with our experimental results. Our studies also revealed the "prediction of third phase formation" before its occurrence for a range of actinide-extractant systems.

Obtaining of trialkylphosphates in anodic dissolution of copper phosphide

Due to obtain trialkylphosphate is suggested to use anodic solution of copper phosphide in alcohol solutions. At this, it can use copper phosphide, obtained at the processing of wastes of phosphorus production. Moreover, it is presented ways of obtaining of tri-n-butylphosphate and tri-izo-butylphosphate.

Electrocatalytic eco-efficient functionalization of white phosphorus

The novel eco-efficient methods to transform white phosphorus into the esters of phosphoric, phosphorous and phosphonic acids, tertiary phosphines and other organophosphorus compounds under conditions of electrochemical catalysis were elaborated. The mechanism of these processes was investigated using the method of cyclic voltammetry and preparative electrolysis.

Oxidative alkoxylation of zinc phosphide in alcoholic solutions of copper(II) chloride

Oxidative alkoxylation of Zn3P2 with the formation of valuable phosphoric and phosphorous acid esters occurred at a high rate and with a high selectivity in alcoholic solutions of CuCl2 under the action of oxygen at 30-60°C. Depending on the nature of the alcohol, two products were formed, namely, trialkyl phosphates (RO)3PO and dialkyl phosphites (RO)2HPO. Water favored the formation of dialkyl phosphates (RO)2(HO)PO. The kinetics and mechanism of the new catalytic reaction were studied, and the optimal conditions for conducting this reaction were found. The reaction proceeded in a topochemical mode by a separate redox mechanism.

Transesterification process

PCT No. PCT/GB95/01883 Sec. 371 Date Jul. 21, 1997 Sec. 102(e) Date Jul. 21, 1997 PCT Filed Aug. 9, 1995 PCT Pub. No. WO96/05208 PCT Pub. Date Feb. 22, 1996A process for the preparation of a phosphate ester is disclosed. A triaryl phosphate is reacted with an alcohol in the presence of a catalytic quantity of a base to produce the phosphate ester product. The base has a base strength of less than 11, and is preferably potassium fluoride or potassium carbonate. Trialkyl phosphates, dialkyl monoaryl phosphates, monoalkyl diaryl phosphates, and mixtures of these compounds can be produced by this process.

Electrochemical Oxidation of Metal Dialkyl Phosphites and Their Reaction with Halogens

Electrochemical oxidation of sodium dialkyl phosphites with alkyl radicals of normal structure leads to formation of tetraalkyl pyrophosphites as the main products, while electrochemical oxidation of litium dialkyl phosphites and sodium salts with branched alkyl radicals yields tetraalkyl hypophosphates. The reaction of metal dialkyl phosphites with halogens leads to analogous results.

Synthesis of dialkyl phosphites and trialkyl phosphates by oxidation of sodium hypophosphite by copper(II) chloride

Sodium hypophosphite oxidazies in alcoholic solution of CuCl2 at 50-80 deg C to give dialkyl phosphite and trialkyl phosphate.The yield of trialkyl phosphate increases with decreasing molecular weight of the alcohol and reaches ca. 100percent for MeOH and EtOH.The optimal conditions were found, and the mechanism of oxidation of NaPH2O2 to (RO)2PHO and (RO)3PO by copper(II) chloride was studied.The reaction proceeds via the formation of alkyl hypophosphite and copper(II) complexes with alkyl hypophosphite and dialkyl phosphite, which undergo inner-sphere two-electron redox decomposition with the liberation of dialkyl phosphite and trialkyl phosphate, respectively.

THE INTERACTION OF PHOSPHITE ESTERS WITH α-IODOKETONES IN THE PRESENCE OF SILVER ION

The reactions of trialkyl phosphites with α-iodoketones in the presence of silver perchlorate or silver tetrafluoroborate yield the corresponding trialkyl phosphates and tetra-alkyl pyrophosphates. Under certain conditions, CIDNP effects indicate the involvement of radical-pairs in the formation of unstable betaine intermediates.

CHLORINATION OF PHOSPHINE IN ALCOHOLS

Trialkyl phosphates are rapidly and selectively formed when dilute gaseous PH-Ar and Cl2-Ar mixtures are passed into alcohols (ROH, R=Bu, i-Bu, Am, i-Am, Oct) at 50-70 deg C.Analogous results are obtained in the presence of pyridine at 8-25 deg C.The reaction was studied by gas chromatography, 31P NMR spectroscopy, and potentiometry.The reaction was shown to pass successively through the stages of the chlorination of phosphine to PCl5, the alcoholysis of phosphorus pentachloride to phosphoryl chloride, and finally by the esterification of phsophoryl chloride to trialkyl and dialkyl phosphates.Pyridine, excess af alcohol, and high temperature accelerate the stage of the esterification of phosphoryl chloride to the trialkyl phosphate.