Phenylphosphine

Structural formula
General
Surname	Phenylphosphine
other names	Monophenylphosphine; Monophenylphosphine;
Molecular formula	C 6 H 7 P
Brief description	colorless liquid
External identifiers / databases
EC number	211-325-4
ECHA InfoCard	100.010.297
PubChem	12519
Wikidata	Q7181435
properties
Molar mass	110.10 g mol −1
Physical state	liquid
density	1.001 g cm −3 (15 ° C)
Melting point	13.8 ° C
boiling point	160-161 ° C
Vapor pressure	13 hPa (40 ° C)
solubility	almost insoluble in water
Refractive index	1.5796 (20 ° C)
safety instructions
H and P phrases	H: 250-252-332-315-319-335
	P: 210-222-305 + 351 + 338-405-422-501
MAK	Switzerland: 0.05 ml m −3 or 0.25 mg m −3
	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

Phenylphosphine is an organic phosphorus compound or a monosubstituted phosphine derivative .

Presentation and extraction

Phenylphosphine is synthesized by reducing dichlorophenylphosphine using lithium aluminum hydride .

{\ displaystyle \ mathrm {2 \ C_ {6} H_ {5} PCl_ {2} \ + \ LiAlH_ {4} \ longrightarrow \ 2 \ C_ {6} H_ {5} PH_ {2} \ + \ LiAlCl_ {4 }}}

properties

Phenylphosphine is a colorless liquid with an unpleasant to nauseating odor. Similar to phosphine, the compound tends to spontaneously ignite in air. It is therefore to be regarded as pyrophoric. The controlled oxidation by atmospheric oxygen produces the corresponding phosphonic acid.

{\ displaystyle \ mathrm {C_ {6} H_ {5} PH_ {2} \ + \ O_ {2} \ longrightarrow \ C_ {6} H_ {5} P (OH) _ {2}}}

use

Phenylphosphine is used in polymer synthesis, where it forms phosphorus-containing polymers in a polyaddition with 1,4-divinylbenzene or 1,4-diisopropenylbenzene . These have self-extinguishing properties in the event of ignition. Flame-resistant materials can be obtained when mixed with flammable polymers such as polyethylene or polypropylene .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Lutz Roth, Ursula Weller-Schäferbarthold: Hazardous chemical reactions. 41. Supplementary delivery, ecomed-Verlag 2003.
↑ ^a ^b ^c ^d ^e Entry for CAS no. 638-21-1 in the GESTIS substance database of the IFA , accessed on May 7, 2013 (JavaScript required)
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-430.
↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 638-21-1 or phenylphosphine ), accessed on November 2, 2015.
^ ^A ^b Leon D. Freedman, GO Doak: The Reduction of Benzenephosphonyl Dichloride . In: Journal of the American Chemical Society . tape 74 , no. 13 , July 1, 1952, p. 3414–3415 , doi : 10.1021 / ja01133a504 .
↑ Takatsugu Obata, Eiichi Kobayashi, Sadahito Aoshima, Junji Furukawa: Synthesis of new linear polymers containing phosphorus atom in the main chain by the radical polyaddition: Addition polymers of phenylphosphine with 1,4-divinylbenzene or 1,4-diisopropenylbenzene and their properties . In: Journal of Polymer Science Part A: Polymer Chemistry . tape 32 , no. 3 , 1994, p. 475-483 , doi : 10.1002 / pola.1994.080320309 .

[Roth-Weller-1] ↑ ^a ^b ^c ^d ^e ^f Lutz Roth, Ursula Weller-Schäferbarthold: Hazardous chemical reactions. 41. Supplementary delivery, ecomed-Verlag 2003.

[GESTIS-2] Entry for CAS no. 638-21-1 in the GESTIS substance database of the IFA , accessed on May 7, 2013 (JavaScript required)

[CRC90_3_430-3] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-430.

[4] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 638-21-1 or phenylphosphine ), accessed on November 2, 2015.

[Freedman-5] A ^b Leon D. Freedman, GO Doak: The Reduction of Benzenephosphonyl Dichloride . In: Journal of the American Chemical Society . tape 74 , no. 13 , July 1, 1952, p. 3414–3415 , doi : 10.1021 / ja01133a504 .

[6] Takatsugu Obata, Eiichi Kobayashi, Sadahito Aoshima, Junji Furukawa: Synthesis of new linear polymers containing phosphorus atom in the main chain by the radical polyaddition: Addition polymers of phenylphosphine with 1,4-divinylbenzene or 1,4-diisopropenylbenzene and their properties . In: Journal of Polymer Science Part A: Polymer Chemistry . tape 32 , no. 3 , 1994, p. 475-483 , doi : 10.1002 / pola.1994.080320309 .