Nitric Acid → 2-Methylbenzoic acid

HRID 1953195Notes

Reaction equation

HRID 1953195 reaction equation
C1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=[O:12])=[CH:8][CH:9]=2)C=CC=1C(O)=O.[C:17](O)(=O)C1C=CC(C(O)=O)=CC=1.[N+]([O-])(O)=O>C1(C)C(C)=CC=CC=1>[CH3:17][C:8]1[CH:9]=[CH:10][CH:5]=[CH:6][C:7]=1[C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 944Nitric Acid2×HCID 7489Terephthalic Acid2×HCID 143572,6-Naphthalenedicarboxylic acid

Product 1

HCID 83732-Methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent3×

Procedure

Organic acids, such as naphthalene-2,6-dicarboxylic acid or terephthalic acid, are highly useful in the manufacture of polyester-type and polyamide-type resins, including polyethyleneterephthalate. Such organic acids customarily have been prepared by a liquid phase oxidation of an alkyl-substituted aromatic precursor in the presence of an aqueous acidic reaction medium, and usually in the presence of a metal catalyst. For example, U.S. Pat. No. 2,766,281 discloses the preparation of phthalic acids, including terephthalic acid, by a step-wise oxidation of a corresponding xylene with concentrated nitric acid at atmospheric pressure and in the presence of an inert organic reaction medium that is liquid at the reaction temperatures. In the first step, the xylene starting material is reacted with the nitric acid at a temperature of from about 120 ° C. up to the boiling point of the xylene starting material, while removing water by distillation, to form a toluic acid. In the second step, nitric acid is slowly added to the toluic acid at a temperature in excess of about 140 ° C., while removing water by distillation, to form the product phthalic acid.

Workup

  1. customat the reaction temperatures
  2. customwhile removing water
  3. distillationby distillation

Sources & evidence

ORD record
ord-901f6e084e774ae39b1a3fb3569abeae
Source dataset
uspto-grants-2000_09
Patent number
US06114574

Reaction notes

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