Styrene → HCID 131712717, compound

HRID 1065588Notes

Reaction equation

HRID 1065588 reaction equation
[OH-].[Na+].[CH3:3][CH:4]([C:11]1C(C(C)C2C=CC=CC=2)=C(C)C(C)=CC=1)[C:5]1C=CC=C[CH:6]=1.[CH3:27][CH:28]([CH:35]([CH:43]([CH3:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[CH2:36][C:37]1C=CC=CC=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[CH2:51]=[CH:52][C:53]1C=CC=[CH:55][CH:54]=1>>[CH:29]1([CH:28]([C:35]2([CH:43]([CH:44]3[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]3)[CH3:50])[CH2:36][CH2:37][C:4]([CH3:11])([CH3:3])[CH2:5][CH2:6]2)[CH3:27])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.[CH:44]1([CH:43]([C:35]2([CH:28]([CH:29]3[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]3)[CH3:27])[CH2:36][CH2:37][CH:53]([CH2:54][CH3:55])[CH2:52][CH2:51]2)[CH3:50])[CH2:45][CH2:46][CH2:47][CH2:48][CH2:49]1

Participants

4

Reactant 3

HCID 7501StyreneHCID 14798Sodium HydroxideHCID 86738371HCID 86738371, compound

Product 1

HCID 131712717HCID 131712717, compound

Conditions

Temperature
14 °C

Procedure

Twenty-one (21) Kl/hr of the distillate (a mixture of α-methylbenzylxylene and α-methylbenzylethylbenzene) boiling in the range of 300°-319° C. obtained in Example 2, 0.1 Kl/hr of styrene and 0.4 Kl/hr of sulphuric acid (92%) were supplied into a 17-Kl reactor (average residence time: about 48 minutes) and so cooled from outside as to maintain the reaction temperature at 14° C. The resulting effluent from the autoclave was allowed to stand still thereby to separate the lower layer (sulphuric acid) for re-circulation and obtain the upper layer (oil layer). The upper layer so obtained was neutralized with an aqueous solution of sodium hydroxide, washed with water and distilled to recover the unreacted α-methylbenzylxylene/α-methylbenzylethylbenzene mixture for re-circulation and then obtain 270 Kg/hr of a distillate boiling in the range of 193°-220° C. at 3 mm Hg. This distillate was found to be a mixture corresponding to the bis-(α-methylbenzyl) xylene/bis-(α-methylbenzyl) ethylbenzene mixture (9:1) obtained in Example 4. As the residue (after the distillation), 3 Kg/hr of styrene polymers was obtained. Thus, it was found that 95% of the styrene was consumed for the alkylation. Four hundred (400) grams of the aforesaid distillate boiling in the range of 193°-220° C. at 3 mm Hg were hydrogenated to obtain 440 cc of a bis-(α-cyclohexylethyl) dimethylcyclohexane/bis-(α-cyclohexylethyl) ethylcyclohexane mixture (traction fluid (II) of this invention) having a specific gravity (15/4° C.) of 0.90, a refractive index (nD20) of 1.490, a kinetic viscosity of 10.9 cSt (98.9° C.), and a traction coefficient of 0.093 (25° C.) or 0.075 (80° C.).

Workup

  1. customwere supplied into a 17-Kl reactor
  2. temperature(average residence time: about 48 minutes) and so cooled from outside as
  3. customto separate the lower layer (sulphuric acid) for re-circulation
  4. customobtain the upper layer (oil layer)
  5. customThe upper layer so obtained
  6. washwashed with water
  7. distillationdistilled
  8. customto recover the unreacted α-methylbenzylxylene/α-methylbenzylethylbenzene mixture for re-circulation
  9. customobtain 270 Kg/hr of a distillate
  10. customboiling in the range of 193°-220° C. at 3 mm Hg
  11. customobtained in Example 4
  12. distillationAs the residue (after the distillation), 3 Kg/hr of styrene polymers
  13. customwas obtained
  14. customwas consumed for the alkylation
  15. customboiling in the range of 193°-220° C. at 3 mm Hg

Sources & evidence

ORD record
ord-1288f2cc7d85493eb9f73615b604a64a
Source dataset
uspto-grants-1982_05
Patent number
US04329529

Reaction notes

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