Methane → Chlorodiphenylphosphine

HRID 1648429

Reaction equation

HRID 1648429 reaction equation
[C:1]1([P:7]([Cl:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=O.[CH4:17]>C1(C)C=CC=CC=1>[CH:4]1[CH:5]=[CH:6][C:1]([P:7]([P:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:17]2[CH:10]=[CH:9][CH:8]=[CH:13][CH:12]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:2][CH:3]=1.[C:1]1([P:7]([Cl:14])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 297MethaneHCID 977OxygenHCID 66180Chlorodiphenylphosphine

Product 2

HCID 66180ChlorodiphenylphosphineHCID 70673Tetraphenyldiphosphine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of diphenylphosphinous chloride, 7.0 grams, 0.03 moles, and calcium carbide, 2.0 grams, 0.038 moles is vigorously stirred for 22 hours under a nitrogen atmosphere and at a temperature of about 160° C., care being taken to avoid oxygen and moisture contamination. The hot mixture is cooled to room temperature and mixed with dry toluene, 60 ml, at 100° C. Charcoal is then added to the solution, which is filtered while hot. The toluene is removed by evaporation using a rotary evaporator, leaving crude tetraphenyldiphosphine and unreacted diphenylphosphinous chloride. Dry ether, 60 ml, is added to the mixture to precipitate the tetraphenyldiphosphine. The solids are isolated by filtration and washed with dry, cold ether three times in order to remove any unreacted diphenylphosphinous chloride, and the remaining solids are dried in vacuo at room temperature. The product is then treated with 1 percent aqueous KOH solution and washed three times with distilled water, three times with dry ether, and then vacuum dried at 35° C. for 24 hours. The yield is 7.4 grams, 63 percent. The product is characterized by its melting point, measured as 120° C., which is in good agreement with the melting point, 120.5° C., obtained from the literature. An infrared spectrum of the product is obtained which is found to be identical to an infrared spectrum of tetraphenylbiphosphine obtained from the literature, confirming the structure of the product obtained.

Workup

  1. temperatureThe hot mixture is cooled to room temperature
  2. filtrationis filtered while hot
  3. customThe toluene is removed by evaporation
  4. customa rotary evaporator

Sources & evidence

ORD record
ord-94ae65eb1e094a6db46d3a03b94d0660
Source dataset
uspto-grants-1995_07
Patent number
US05436280

Linked notes

Loading…