Methyl iodide → Methyltriphenylphosphonium iodide
Reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[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.[CH3:20][I:21]>>[I-:21].[CH3:20][P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1Participants
Procedure
If the alkane distillation bottoms stream is contacted with a phosphine, the phosphine is preferably added to the alkane distillation bottoms stream at moderate temperatures. Suitable temperatures are in the range of about 10° C. to 100° C., preferably 15° C. to 80° C. The phosphine reacts with the methyl iodide in solution to produce a methyl phosphonium iodide species; for example, the reaction of triphenylphosphine and methyl iodide produces methyl triphenylphosphonium iodide. This compound is a valuable starting material used in the pharmaceutical and small molecule industries to make olefins from carbonyls using the Wittig reaction. The methyl phosphonium iodide may be recovered from the alkane distillation bottoms stream by any suitable process, but is preferably recovered by filtration as the methyl phosphonium iodide species is insoluble in the alkane distillation bottoms stream.
Sources & evidence
- ORD record
- ord-53b9023774ef40cdba3943afa989cf7e
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394987B2
Reaction notes
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