Phosphoric Acid → Methyl 3-pentenoate

HRID 231354Notes

Reaction equation

HRID 231354 reaction equation
P(=O)(O)(O)O.CO[CH:8]([CH2:14][CH3:15])[CH2:9][C:10]([O:12][CH3:13])=[O:11]>>[C:10]([O:12][CH3:13])(=[O:11])[CH2:9][CH:8]=[CH:14][CH3:15].[C:10]([O-:12])(=[O:11])/[CH:9]=[CH:8]/[CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 12636344Methyl 3-methoxyvalerate

Product 2

HCID 101865Methyl 3-pentenoateHCID 69933462-Pentenoate

Conditions

Temperature
300 °C

Procedure

A 1 l stirred flash was charged with 500 g of vacuum gas oil and 6 g of an 85% strength phosphoric acid, and the mixture was heated to 300° C. 40 g/hour of methyl 3-methoxyvalerate from a stock vessel were fed, together with 10 l/hour of nitrogen, below the surface of the stirred oil/catalyst mixture. The gaseous products leaving the reaction vessel were cooled, and the condensate was investigated by gas chromatography. In this manner, 11.0 g/hour of methyl 3-pentenoate and 10.7 g/hour of 2-trans-pentenoate were obtained, inter alia, in addition to 7.5 g/hour of unconverted methyl 3-methoxyvalerate.

Workup

  1. customThe gaseous products leaving the reaction vessel
  2. temperaturewere cooled

Sources & evidence

ORD record
ord-68a06b2bde974580b8225e70167e4adc
Source dataset
uspto-grants-1989_07
Patent number
US04845269

Reaction notes

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