Propylene Glycol → HCID 86754656, compound

HRID 1861566Notes

Reaction equation

HRID 1861566 reaction equation
[CH2:1]([OH:5])[CH:2]([OH:4])[CH3:3].[C:6]([OH:13])(=[O:12])/[CH:7]=[CH:8]/[C:9]([OH:11])=[O:10].C1(O)C(=CC(=CC=1)O)C.C(O)C(O)C.C(O)(=O)/C=C/C(O)=O.[OH-].[K+]>>[CH2:1]([OH:5])[CH:2]([OH:4])[CH3:3].[C:6]([O-:13])(=[O:12])/[CH:7]=[CH:8]/[C:9]([O-:11])=[O:10]

Participants

6

Reactant 5

HCID 1030Propylene Glycol2×HCID 7253MethylhydroquinoneHCID 14797Potassium HydroxideHCID 444972Fumaric Acid2×HCID 19804501HCID 19804501, compound

Product 1

HCID 86754656HCID 86754656, compound

Conditions

Temperature
193 °C

Procedure

A conventional ten-gallon stainless steel reactor was charged with 17.02 kg of propylene glycol (available from Ashland Chemical Company of Columbus, Ohio) and 12.98 kg of fumaric acid (available from Huntsman Specialty Chemical of Salt Lake City, Utah). For stability, 3.62 g (120 ppm) of toluhydroquinone (THQ) (available from Aldrich Chemical Company of Milwaukee, Wis.) was added into the reactor. The molar ratio of the charge was 2:1 propylene glycol (PG) to fumaric acid (FA). The mixture was heated under a nitrogen atmosphere at 380° F. (193° C.) for five hours. The endpoint of the reaction was determined by the viscosity of the PG-FA product, which was 360 to 450 cps at 120° F. (49° C.) as determined by a cone-and-plate viscometer, such as that made by ICI of Wilmington, Del. The acid value at the reaction endpoint is typically observed to be 10 to 36 Meq KOH/g of alkyd (milliequivalent of potassium hydroxide per gram of alkyd). This material may be used directly as a film former.

Workup

  1. customat 120° F.
  2. custom(49° C.)

Sources & evidence

ORD record
ord-2a0c5026e72542cd85dd8c88821c7c08
Source dataset
uspto-grants-2003_03
Patent number
US06533882B1

Reaction notes

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