Methane → (2E,4Z)-2,4-Hexadienedioic acid

HRID 385193Notes

Reaction equation

HRID 385193 reaction equation
[C:1]([OH:10])(=[O:9])/[CH:2]=[CH:3]\[CH:4]=[CH:5]/[C:6]([OH:8])=[O:7].[OH-].[Na+].C>O>[C:1]([OH:10])(=[O:9])/[CH:2]=[CH:3]\[CH:4]=[CH:5]\[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 297MethaneHCID 14798Sodium HydroxideHCID 5280518cis,cis-Muconic acid

Product 1

HCID 5280614(2E,4Z)-2,4-Hexadienedioic acidYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Cis,cis-Muconic acid (100 g) is dissolved in water (1 L, then adjusted to pH 6 by adding base, sodium hydroxide) and the mixture is heated at 90° C. for 3.5 hours. Samples are taken every 30 minutes and analyzed by HPLC. HPLC analyses of these samples show that the isomerization process is almost complete after 1 hour of heating at 90° C. After 3.5 hours of heating at 90° C., the mixture is treated with charcoal (10 g) for 30 minutes and filtered through a Whatman filter paper (#2). The pH of the solution is adjusted to 3.5 by adding base, sodium hydroxide. The precipitate is obtained by filtration, washed with ice-cold water (200 mL), and dried under reduced pressure to yield 64.5 g (65 percent yield) of light yellow cis,trans-muconic acid.

Workup

  1. waitis almost complete after 1 hour
  2. temperatureof heating at 90° C
  3. temperatureAfter 3.5 hours of heating at 90° C.
  4. filtrationfiltered through a Whatman
  5. filtrationfilter paper (#2)
  6. additionby adding base, sodium hydroxide
  7. customThe precipitate is obtained by filtration
  8. washwashed with ice-cold water (200 mL)
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-c3e0827a438a45c8be807ae42a2b1203
Source dataset
uspto-grants-2013_02
Patent number
US08367858B2

Reaction notes

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