Benzyl Alcohol → Tribenzylbenzene

HRID 1065587Notes

Reaction equation

HRID 1065587 reaction equation
[CH2:1](O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(F)(F)F.C1(CC2C=CC=CC=2)C=CC=CC=1.[CH2:26]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1C=CC=CC=1>[CH2:1]([C:35]1[C:34]([CH2:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)=[C:33]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:38]=[CH:37][CH:36]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 6356Boron trifluorideHCID 7580Diphenylmethane2×HCID 10934161Benzene, 1,2-bis(phenylmethyl)-

Product 1

HCID 14877094Tribenzylbenzene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

Two thousand one hundred and eighty (2,180) grams (2,060 cc) of benzyl alcohol and 1,560 g (1,780 cc) of benzene were introduced into a 10-liter flask, and 940 g of boron trifluoride gas was blown into the flask. The whole mass was transferred into an autoclave, agitated at 60° C. for 9 hours, heated, thereafter cooled and then separated into the lower layer (acid layer) and upper layer (oil layer). The upper layer (oil layer) was incorporated with 1.5 l of a 10% aqueous solution of sodium hydroxide, repeatedly agitated and washed eight times and then distilled to obtain 480 g of a distillate boiling in the range of 173°-176° C. at 72 mm Hg. This distillate had a boiling point of 261° C. at atmospheric pressure, 175° C. at 72 mm Hg, 149° C. at 29 mm Hg or 85° C. at 1 mm Hg, a specific gravity (30/4° C.) of 0.997, a viscosity of 0.01564 g/cm.sec (59° C.) ad a refractive index (nD25) of 1.570, and it was found to be diphenylmethane as the main ingredient from its NMR spectra and gas chromatography. The yield of the diphenylmethane was about 15% (about 460 g), and other distillates having a high boiling point such as dibenzylbenzene and tribenzylbenzene were produced in an amount of 989 g as by-products.

Workup

  1. temperatureheated
  2. temperaturecooled
  3. customseparated into the lower layer (acid layer) and upper layer (oil layer)
  4. stirringrepeatedly agitated
  5. washwashed eight times
  6. distillationdistilled
  7. customto obtain 480 g of a distillate
  8. customboiling in the range of 173°-176° C. at 72 mm Hg
  9. customat atmospheric pressure, 175° C.
  10. customat 72 mm Hg, 149° C.
  11. customat 29 mm Hg or 85° C.
  12. customa specific gravity (30/4° C.) of 0.997
  13. customsec (59° C.) ad

Sources & evidence

ORD record
ord-01dacb5dcbac47c6943ab823ed9c5ef0
Source dataset
uspto-grants-1982_05
Patent number
US04329529

Reaction notes

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