Sulfuric Acid → 2-(2-Methylphenyl)octadecanoic acid

HRID 223779

Reaction equation

HRID 223779 reaction equation
S(=O)(=O)(O)O.[C:6]([OH:25])(=[O:24])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[C:26]1([CH3:32])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[C:26]1([CH3:32])[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH:7]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:6]([OH:25])=[O:24]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 1140Toluene2×HCID 445639Oleic Acid

Product 1

HCID 223239372-(2-Methylphenyl)octadecanoic acid

Conditions

Temperature
5 °C

Procedure

Concentrated sulfuric acid (1470 gms; 15 moles) were charged to a glass reactor equipped with a condenser, mechanical stirrer, thermometer, and addition funnel and cooled to about 5° C. Toluene (1380 gms; 15 moles) was then added over a two hour period while maintaining the temperature below 10° C. When the addition of toluene was complete, 831 gms (3 moles) oleic acid was incrementally added over a period of two hours. The reaction mixture was maintained below 10° C. for 1/2 hour and then allowed to rise to room temperature with continued stirring for 2 hours. Tolylstearic acid (1118.6 gms; 86.1% crude yield; acid value 154) was recovered and vacuum distilled.

Workup

  1. customequipped with a condenser, mechanical stirrer
  2. additionthermometer, and addition funnel
  3. temperaturewhile maintaining the temperature below 10° C
  4. temperatureThe reaction mixture was maintained below 10° C. for 1/2 hour
  5. customto rise to room temperature
  6. customTolylstearic acid (1118.6 gms; 86.1% crude yield; acid value 154) was recovered
  7. distillationvacuum distilled

Sources & evidence

ORD record
ord-4c7dd1e700c140e090338e4b9b5d59ff
Source dataset
uspto-grants-1982_10
Patent number
US04356315

Linked notes

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