Tributylphosphine

Structural formula
General
Surname	Tributylphosphine
other names	Tri- n -butylphosphine; Tributylphosphine;
Molecular formula	C 12 H 27 P
Brief description	light yellow, pyrophoric liquid with a garlic-like odor
External identifiers / databases
EC number	213-651-2
ECHA InfoCard	100.012.410
PubChem	13831
ChemSpider	13231
Wikidata	Q7840573
properties
Molar mass	202.32 g mol −1
Physical state	liquid
density	0.82 g cm −3 (20 ° C)
Melting point	−60 ° C
boiling point	240-250 ° C
Vapor pressure	0.09 mbar (20 ° C)
solubility	practically insoluble in water
Refractive index	1.462 (20 ° C)
safety instructions
H and P phrases	H: 226-250-302-312-314-411
	P: 210-303 + 361 + 353-231 + 232-301 + 330 + 331-305 + 351 + 338-310
Toxicological data	750 mg kg −1 ( LD 50 , rat , oral ) ; 2000 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Tributylphosphine with the constitutional formula P (C ₄ H ₉ ) ₃ is a chemical compound of phosphorus from the group of organic phosphorus compounds .

Presentation and extraction

Tributylphosphine can be obtained from n-butyl bromide and magnesium by reacting phosphorus trichloride with the Grignard reagent .

{\ displaystyle \ mathrm {PCl_ {3} +3 \ BrMgC_ {4} H_ {9} \ longrightarrow P (C_ {4} H_ {9}) _ {3} +3 \ MgClBr}}

properties

Tributylphosphine is a slightly volatile, pyrophoric , light yellow liquid with a garlic-like odor, which is practically insoluble in water. However , the compound is miscible in any ratio with ethanol , diethyl ether and benzene .

The deep red crystalline addition compound (C ₄ H ₉ ) ₃ P · CS ₂ is formed with carbon disulfide .

use

Tributylphosphine is used as a catalyst for the trimerization of diisocyanates and for the production of phosphonium salts.

safety instructions

Tributylphosphine forms flammable vapor-air mixtures. The compound has a flash point of 94 ° C. The explosion range lies between 0.7% by volume (65 g / m ³ ) as the lower explosion limit (LEL) and 12.5% by volume (975 g / m ³ ) as the upper explosion limit (UEL). The ignition temperature is 200 ° C. The substance therefore falls into temperature class T4.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p Entry on tributylphosphine in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
↑ Data sheet Tri-n-butylphosphine, 99% from Sigma-Aldrich , accessed on August 10, 2014 ( PDF ).
↑ Baban, Jehan A .; Roberts, Brian P .: in J. Chem. Soc., Perkin Trans. 2: Phys. Org. Chem. (1972-1999), 1981, 161-166.
^ ^A ^b George B. Kauffman and Larry A. Teter: Tri-n-butylphosphine . In: Eugene G. Rochow (Ed.): Inorganic Syntheses . tape 6 . McGraw-Hill Book Company, Inc., 1960, pp. 87-90 (English).
^ ^A ^b ^c E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p Entry on tributylphosphine in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .

[Sigma-2] Data sheet Tri-n-butylphosphine, 99% from Sigma-Aldrich , accessed on August 10, 2014 ( PDF ).

[3] Baban, Jehan A .; Roberts, Brian P .: in J. Chem. Soc., Perkin Trans. 2: Phys. Org. Chem. (1972-1999), 1981, 161-166.

[IS6-4] A ^b George B. Kauffman and Larry A. Teter: Tri-n-butylphosphine . In: Eugene G. Rochow (Ed.): Inorganic Syntheses . tape 6 . McGraw-Hill Book Company, Inc., 1960, pp. 87-90 (English).

[Brandes-5] A ^b ^c E. Brandes, W. Möller: Safety-related parameters - Volume 1: Flammable liquids and gases , Wirtschaftsverlag NW - Verlag für neue Wissenschaft GmbH, Bremerhaven 2003.