Conditions | Yield |
---|---|
With oxygen; phosphan; copper dichloride at 24.9℃; Rate constant; Product distribution; other acohols and reagents, var. concentration of reagents and temperatures; | 100% |
With oxygen; phosphan; copper dichloride at 24.9℃; | 100% |
With oxygen; copper dichloride at 59.9℃; | 100% |
Conditions | Yield |
---|---|
With hydrogenchloride; water; oxygen; copper dichloride at 59.9℃; Product distribution; Mechanism; other alcohols, var. conc. of reagents, var. temperat.; | A 100% B n/a |
With phosphan; chlorine Rate constant; Thermodynamic data; Ea, ΔS(excit.); also in the presence of pyridine; |
Conditions | Yield |
---|---|
With trichlorophosphate In butan-1-ol at 10 - 30℃; for 1.83333h; | 98% |
With diethyl ether; trichlorophosphate; butan-1-ol at 0℃; |
Conditions | Yield |
---|---|
With sodium hypophosphite; copper dichloride at 24.9℃; for 214h; | A 5.5% B 94.5% |
With hydrogenchloride; zinc(II) phosphide; iron(III) chloride at 70℃; | A 90% B 9% |
With sodium hypophosphite; copper dichloride at 24.9℃; for 173h; | A 16.7% B 87.3% |
Conditions | Yield |
---|---|
With ozone In dichloromethane at -75℃; | 92% |
butan-1-ol
A
phosphoric acid tributyl ester
B
n-Butyl chloride
C
dibutyl ether
Conditions | Yield |
---|---|
With oxygen; phosphan; copper(l) chloride; copper dichloride at 24.9℃; Kinetics; Product distribution; Mechanism; ΔE(excit.), ΔS(excit.); other reagents, other catalysts; | A 90% B n/a C n/a |
With oxygen; phosphan; copper(l) chloride; copper dichloride at 24.9℃; | A 90% B n/a C n/a |
butan-1-ol
A
n-butyl phosphoric acid
B
phosphoric acid tributyl ester
C
dibutyl phosphate
Conditions | Yield |
---|---|
With phosphorus; tetraethylammonium iodide In water; acetonitrile electrolysis; | A n/a B 87% C n/a |
Conditions | Yield |
---|---|
With cesium fluoride In acetonitrile for 6h; Ambient temperature; also with n-butylbromide; | 86% |
butan-1-ol
A
phosphoric acid tributyl ester
B
butylbis(α-hydroxybutyl)phosphine oxide
Conditions | Yield |
---|---|
With phosphan; p-benzoquinone at 80℃; Kinetics; Condensation; oxidation; | A 15% B 85% |
Conditions | Yield |
---|---|
With sodium bromate; phosphan at 80℃; Kinetics; Condensation; | A 20% B 80% |
With sodium hypophosphite; copper dichloride at 24.9℃; for 4h; | A 22.2% B 77.8% |
With phosphorous; air; ruthenium hydroxide trichloride; copper dichloride at 80℃; oxidative alkoxylation; | A 33.7% B 11.3% |
Conditions | Yield |
---|---|
With sodium hydroxide; tetrabutylammomium bromide In tetrachloromethane; dichloromethane at 15℃; for 3h; | 71.6% |
tri-n-butyl phosphite
A
sulfuric acid dibutyl ester
B
phosphoric acid tributyl ester
C
dibutyl butylphosphonate
Conditions | Yield |
---|---|
With sulfur trioxide In dichloromethane at -50℃; | A 28% B 70% C 2% |
Conditions | Yield |
---|---|
With lutidine; tellurium tetrachloride In dichloromethane for 3h; Ambient temperature; | A 30% B 70% |
tri-n-butyl phosphite
A
sulfuric acid dibutyl ester
B
phosphoric acid tributyl ester
C
O,O,O-tributyl phosphorothioate
D
dibutyl butylphosphonate
Conditions | Yield |
---|---|
With sulfur trioxide In dichloromethane at -50℃; | A 2% B 64% C 22% D 12% |
Conditions | Yield |
---|---|
With phosphorous; tetraethylammonium iodide In acetonitrile at 56℃; electrolysis; | A 60% B 15% |
With phosphorous In acetonitrile at 56℃; Electrolysis; | A 60% B 15% |
Conditions | Yield |
---|---|
With tetraethylammonium iodide; water In acetonitrile at 55℃; electrosynthesis; | A 16% B 51% |
tri-n-butyl phosphite
A
dibutyl hydrogen phosphite
B
phosphoric acid tributyl ester
Conditions | Yield |
---|---|
With HOF* CH3CN In dichloromethane at 0℃; for 0.0833333h; | A 50% B 40% |
tri-n-butyl phosphite
3-Phenyl-1-propanol
A
phosphoric acid tributyl ester
B
dibutyl 3-phenylpropyl phosphate
C
butyl bis(3-phenylpropyl) phosphate
Conditions | Yield |
---|---|
Stage #1: tri-n-butyl phosphite; 3-Phenyl-1-propanol With 1H-tetrazole In dichloromethane at 20℃; for 22h; transesterification; Stage #2: With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -78 - 20℃; for 0.5h; Oxidation; | A 21% B 36% C 16% |
With 1H-tetrazole; 3-chloro-benzenecarboperoxoic acid multistep reaction: transesterification of trialkyl phosphites with an alcohol; | |
With 1H-tetrazole; 3-chloro-benzenecarboperoxoic acid 1) CH2Cl2, room temperature, 22 h; Yield given. Multistep reaction. Yields of byproduct given; |
Conditions | Yield |
---|---|
With Cumene hydroperoxide In benzene at 20℃; Rate constant; | |
With dinitrogen tetraoxide im Stickstoff-Strom; | |
With nitrosylchloride anschliessenden Erhitzen auf 150grad; |
Conditions | Yield |
---|---|
With trichlorophosphate; benzene |
Conditions | Yield |
---|---|
With sodium hydroxide at 255℃; |
methanol
tri-n-butyl phosphite
A
dibutyl methyl phosphate
B
phosphoric acid tributyl ester
Conditions | Yield |
---|---|
With oxygen; methylene blue In acetonitrile at 20℃; for 0.166667h; Mechanism; Product distribution; Irradiation; without methanol; other reaction time; also in the presence of diphenyl sulfides or sulfoxides as trapping agents of intermediates; | A n/a B 73 % Chromat. |
tri-n-butyl phosphite
chlorofluoronitromethane
A
phosphoric acid tributyl ester
B
n-Butyl chloride
C
C9H19FNO4P
D
C9H19FNO4P
Conditions | Yield |
---|---|
at 50℃; for 2h; Title compound not separated from byproducts; |
tri-n-butyl phosphite
trimethylsilyl(cumyl) peroxide
A
Trimethylsilanol
B
phosphoric acid tributyl ester
C
Hexamethyldisiloxane
D
1-methyl-1-phenylethyl alcohol
E
1-phenyl-1-methyl-1-trimethylsiloxyethane
F
acetophenone
Conditions | Yield |
---|---|
In various solvent(s) at 343℃; Rate constant; Mechanism; Product distribution; E(activ.); |
tri-n-butyl phosphite
A
phosphoric acid tributyl ester
B
dibutyl 3-phenylpropyl phosphate
C
butyl bis(3-phenylpropyl) phosphate
Conditions | Yield |
---|---|
With 1H-tetrazole; 3-Phenyl-1-propanol; 3-chloro-benzenecarboperoxoic acid 1) CH2Cl2, room temperature, 22 h; Yield given. Multistep reaction. Yields of byproduct given; |
tri-n-butyl phosphite
A
phosphoric acid tributyl ester
B
dibutyl chlorophosphate
Conditions | Yield |
---|---|
With sulfuryl dichloride at 20 - 30℃; | A 10 % Spectr. B 90 % Spectr. |
Conditions | Yield |
---|---|
at 60℃; Rate constant; Thermodynamic data; activation energy, activation enthalpy, other temperature (40, 50, 70, 80 deg C); | |
at 60℃; Rate constant; other temperature (50, 80 deg C); |
Conditions | Yield |
---|---|
With phosphan; copper dichloride In N,N-dimethyl-formamide at 24.9℃; Rate constant; Thermodynamic data; ΔS(excit); reaction also with FeCl3; | |
With phosphan; copper dichloride In N,N-dimethyl-formamide at 59.9℃; | |
With oxygen; phosphan; copper(ll) bromide at 50℃; Catalytic behavior; Kinetics; Mechanism; Reagent/catalyst; Temperature; |
butyl dichlorophosphate
dibutyl chlorophosphate
phosphoric acid tributyl ester
Conditions | Yield |
---|---|
at 20.1℃; Rate constant; Kinetics; var. molar ratios of edduct, temp., and solvents; also with HCl; |
sodium butanolate
dibutyl (4,6-dimethyl-2-pyrimidyl) phosphate
A
4,6-dimethylpirimidin-2-one
B
phosphoric acid tributyl ester
Conditions | Yield |
---|---|
In para-xylene at 140℃; for 2h; Product distribution; phosphorylation; |
Conditions | Yield |
---|---|
With salophen(tBu)AlBr In chloroform-d1 at 20℃; for 0.5 - 24h; Product distribution / selectivity; | 100% |
With (N,N'-ethylenebis(3,5-di-tert-butylsalicylideneimine))AlBr In chloroform-d1 at 20℃; for 0.5 - 24h; Product distribution / selectivity; | 12% |
With (N,N'-propylenebis(3,5-di-tert-butylsalicylideneimine))AlBr In chloroform-d1 at 20℃; for 0.5 - 24h; Product distribution / selectivity; | 7% |
phosphoric acid tributyl ester
[(N,N'-propylenebis(3,5-di-tert-butylsalicylideneimine))AlO]2[(BuO)2PO]2
Conditions | Yield |
---|---|
In toluene to soln. Al complex in toluene (BuO)3PO was added, stirred for 48 h; soln. was filtered, concd. and cooled to -30°C for several days, ppt. was filtered, washed with ether and hexane and dried in vacuo; elem. anal.; | 100% |
1,2,3,4-tetramethylimidazolium methyl carbonate
phosphoric acid tributyl ester
Conditions | Yield |
---|---|
Stage #1: phosphoric acid tributyl ester With diethylamine at 125℃; for 70h; Stage #2: 1,2,3,4-tetramethylimidazolium methyl carbonate In methanol | 99.5% |
trans-Crotonaldehyde
phosphoric acid tributyl ester
benzenesulfonyl cyanide
2-(phenylsulfonyl)pyridine
Conditions | Yield |
---|---|
In toluene; butan-1-ol | 99% |
Conditions | Yield |
---|---|
at 170℃; for 5h; | 98% |
at 150℃; for 24h; | 92% |
phosphoric acid tributyl ester
bromoacetic acid tert-butyl ester
t-butyl-2-(dibutoxyphosphoryl)acetate
Conditions | Yield |
---|---|
at 90℃; for 24h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol; water for 2.5h; Heating; | 97% |
With sodium hydroxide | |
With hydrogenchloride In hydrogenchloride byproducts: C4H9Cl; hydrolysis of TBP in concd. HCl;; hydrolytic decompn. of 18.5 % TBP in 6 days at ambient temp.;; | |
With HCl In hydrogenchloride byproducts: C4H9Cl; hydrolysis of TBP in concd. HCl;; hydrolytic decompn. of 18.5 % TBP in 6 days at ambient temp.;; |
Conditions | Yield |
---|---|
at 200 - 220℃; for 5h; | 96% |
Heating; |
phosphoric acid tributyl ester
sodium [2-13C,2H3]acetate
butyl <2-13C,2H3>acetate
Conditions | Yield |
---|---|
for 5h; Heating; | 96% |
phosphoric acid tributyl ester
Conditions | Yield |
---|---|
In tetrahydrofuran at 90℃; for 8h; | 95.1% |
Conditions | Yield |
---|---|
With urea In 2-methylchlorobenzene; water | 95% |
1,2-benzisothiazolin-3-one
phosphoric acid tributyl ester
2-butyl-1,2-benzothiazolin-3-one
Conditions | Yield |
---|---|
Stage #1: 1,2-benzisothiazolin-3-one With sodium methylate In methanol at 25℃; for 1h; Stage #2: phosphoric acid tributyl ester In methanol for 4h; | 95% |
n-butyllithium
phosphoric acid tributyl ester
dibutyl butylphosphonate
Conditions | Yield |
---|---|
In tetrahydrofuran; hexane at -78 - 0℃; | 94% |
Conditions | Yield |
---|---|
With sodium benzoate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; dichloro(dimethylglyoxime)(dimethylglyoximato)cobalt(III) In 1,2-dichloro-ethane; acetonitrile at 25℃; for 24h; Inert atmosphere; Schlenk technique; Irradiation; | 94% |
Conditions | Yield |
---|---|
at 120℃; for 12h; Inert atmosphere; | 92.5% |
phosphoric acid tributyl ester
2,3-oxynaphthoic acid phenylamide
dimethyl acetylenedicarboxylate
Conditions | Yield |
---|---|
In acetone at 20℃; for 24h; | 91% |
Conditions | Yield |
---|---|
With lithium In tetrahydrofuran at -30℃; for 0.25h; | 90% |
phosphoric acid tributyl ester
naphthol ASD
dimethyl acetylenedicarboxylate
Conditions | Yield |
---|---|
In acetone at 20℃; for 24h; | 90% |
Conditions | Yield |
---|---|
With iron(II) triflate In neat (no solvent) at 100℃; | 90% |
phosphoric acid tributyl ester
[2-13C]-sodium acetate
n-Butyl<2-(13)C>acetate
Conditions | Yield |
---|---|
at 210℃; for 6h; | 88% |
Conditions | Yield |
---|---|
With lithium In tetrahydrofuran at -30℃; for 0.25h; | 86% |
phosphoric acid tributyl ester
toluene-4-sulfonic acid
butyl para-toluenesulfonate
Conditions | Yield |
---|---|
In methyl cyclohexane for 72h; Heating; | 86% |
phosphoric acid tributyl ester
toluene-4-sulfonic acid
toluene
A
butyl para-toluenesulfonate
B
1-sec-butyl-4-methylbenzene
C
2-sec-butyltoluene
Conditions | Yield |
---|---|
In methyl cyclohexane for 72h; Product distribution; Heating; investigate effect of molar ratio, solvent and reaction time; | A 86% B n/a C n/a |
Reported in EPA TSCA Inventory.
OSHA PEL: TWA 0.2 ppm
ACGIH TLV: TWA 0.2 ppm
For occupational chemical analysis use NIOSH: Tributyl Phosphate, S208.
1. Introduction of Tributyl phosphate
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, 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.
2. Properties of Tributyl phosphate
H bond acceptors: 4
H bond donors: 0
Freely Rotating Bonds: 12
Polar Surface Area: 54.57Å2
Index of Refraction: 1.43
Molar Refractivity: 69.75 cm3
Molar Volume: 269.8 cm3
Surface Tension: 31.7 dyne/cm
Density: 0.986 g/cm3
Flash Point: 193.3 °C
Enthalpy of Vaporization: 50.64 kJ/mol
Boiling Point: 288.3 °C at 760 mmHg
Vapour Pressure: 0.00409 mmHg at 25°C
Melting point: -79 °C
Water Solubility: 0.6 g/100 mL
Merck :14,9618
BRN: 1710584
Stability: Stable. Combustible. Incompatible with strong oxidizing agents. May be water sensitive
Product Categories: Organics; Functional Materials; Phosphates (Plasticizer); Plasticizer; Organic Building Blocks; Organic Phosphates/Phosphites; Phosphorus Compounds; Alphabetic; TP - TZ;T-Z, Puriss p.a.; Analytical Reagents for General Use; Puriss p.a.; Analytical/Chromatography; Ion Sensor Materials; Plasticizer for ISE
3. Structure Descriptors of Tributyl phosphate
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
Smiles
P(OCCCC)(OCCCC)(OCCCC)=O
4. Toxicity of Tributyl phosphate
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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