Gamma-Butyrolactone → Glutaric Acid

HRID 1834134Notes

Reaction equation

HRID 1834134 reaction equation
C(O)CCO.I.[C]=O.[CH:9]([OH:13])([OH:12])[CH2:10][CH3:11].OCCCI.[C:19]1(=[O:24])[O:23]CC[CH2:20]1>O>[C:19]([OH:24])(=[O:23])[CH2:20][CH2:11][CH2:10][C:9]([OH:13])=[O:12]

Participants

8

Reactant 6

HCID 7302Gamma-ButyrolactoneHCID 104421,3-PropanediolHCID 24841Hydrogen iodideHCID 693903-Iodo-1-propanol2×HCID 134919Propanediol2×HCID 178418416HCID 178418416, compound2×

Product 1

HCID 743Glutaric Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
175 °C

Procedure

A solution containing 2 mls 1,3-propanediol, 15 mls water, 3 mls of 57% hydriodic acid and 0.1 g RhCl3.XH2O were placed in an autoclave, pressurized with 1200 psi of carbon monoxide, and heated with shaking at 175° C. for 6 hours. Analysis indicated the presence of 7.8 millimoles of gamma-butyrolactones (28.2% conversion based on the propanediol introduced). Unreacted propanediol and 3-hydroxypropyliodide were also present. The solution was returned to the autoclave, pressurized with 1100 psi of carbon monoxide and heated with shaking at 175° C. for 6 hours more. The product now contained 15.1 millimoles of gamma-butyrolactone (54.4% conversion), but some 3-hydroxypropyliodide was also present. No glutaric acid was formed.

Workup

  1. temperatureheated
  2. additionintroduced)
  3. temperatureheated
  4. stirringwith shaking at 175° C. for 6 hours more

Sources & evidence

ORD record
ord-bf0a1a14f5734e3eb9ffed35886f76e3
Source dataset
uspto-grants-1978_01
Patent number
US04069232

Reaction notes

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