2-Naphthoic acid → 2,6-Dimethylnaphthalene

HRID 2081348Notes

Reaction equation

HRID 2081348 reaction equation
C(O)(=O)C1C(=CC(=CC=1)C(O)=O)C(O)=O.[CH:16]1[C:25]2[C:20](=[CH:21][C:22]([C:26](O)=O)=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1[C:29](O)=O.BrC1C2C(=CC(C(O)=O)=CC=2)C=CC=1C(O)=O.C(C1C=CC2C(=CC=C(C(O)=O)C=2)C=1)=O.C1C2C(=CC=CC=2)C=CC=1C(O)=O>>[CH3:26][C:22]1[CH:23]=[CH:24][C:25]2[C:20](=[CH:19][CH:18]=[C:17]([CH3:29])[CH:16]=2)[CH:21]=1

Participants

6

Reactant 5

HCID 71232-Naphthoic acidHCID 10708Trimellitic acidHCID 143572,6-Naphthalenedicarboxylic acidHCID 15919523HCID 15919523, compoundHCID 21189096HCID 21189096, compound

Product 1

HCID 113872,6-Dimethylnaphthalene

Procedure

In the following Examples, "TMLA" is trimellitic acid, "2,6-NDA" is 2,6-naphthalenedicarboxylic acid, "Br-NDA" is bromo-2,6-naphthalenedicarboxylic acid, "FNA" is 2-formyl-6-naphthoic acid and "2-NA" is 2-naphthoic acid. "Reactor Yield" or "Molar Reactor Yield," is the percent yield of each component listed in the oxidation reactor effluent and based on the moles of the component produced relative to the moles of 2,6-dimethylnaphthalene feedstock added. The values reported for carbon monoxide and carbon dioxide are the amounts of those oxidation products produced in gram moles per hour. "HCTP" corresponds to hydrocarbon throughput and is defined as the molar feed rate of 2,6-dimethylnaphthalene in pound moles per hour divided by the volume of solvent in the oxidation reactor. The units for HCTP are pound moles of 2,6-dimethylnaphthalene added to the reactor per cubic foot of reactor solvent in the reactor, per hour. "Solvent Ratio" is approximately the rate of removal of solvent by weight divided by the rate of addition of 2,6-dimethylnaphthalene by weight. This value approximately equals the rate of addition of oxidation reaction solvent divided by the rate of addition of 2,6-dimethylnaphthalene, by weight, i.e. the amount of solvent exiting the oxidation reactor may be greater than that added due to the formation of water in the reaction by the oxidation reaction. "Residence Time" is the oxidation reactor drain weight divided by the reaction mixture effluent rate in pounds per minute. "Wt. % Co" is the weight percent cobalt, measured as elemental cobalt, based on the oxidation reaction solvent added to the oxidation reactor. "Co:Mn:Br." is the gram atom ratio of cobalt:manganese:bromine in the catalyst added to the oxidation reaction mixture. The molten 2,6-dimethylnaphthalene (DMN) feed rate values are in pounds per hour.

Workup

  1. custom"Reactor Yield" or "Molar Reactor
  2. customYield

Sources & evidence

ORD record
ord-900c1b5f05d84cb7ab405ee936d915ba
Source dataset
uspto-grants-1993_02
Patent number
US05183933

Reaction notes

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