Methacrolein → 1,2-Butanediol

HRID 1576593Notes

Reaction equation

HRID 1576593 reaction equation
[O:1]=[CH:2][C:3](=[CH2:5])[CH3:4].C(OCC=C)(=[O:8])C.[CH:13]([OH:18])(O)[CH2:14][CH2:15][CH3:16].C(O)CCC[OH:23]>C(O)(=O)C.O>[CH3:5][CH:3]([CH2:4][OH:8])[CH2:2][OH:1].[CH2:13]([OH:18])[CH:14]([OH:23])[CH2:15][CH3:16]

Participants

8

Reactant 4

HCID 6562MethacroleinHCID 80641,4-ButanediolHCID 11584Allyl acetate2×HCID 165788Butanediol

Product 2

HCID 114291,2-ButanediolYield 13%HCID 75103MethylpropanediolYield 5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

The low boiling components of the hydrogenation mixture (principally water, acetic acid and hydrogenation products derived from methacrolein and allyl acetate) are distilled off under reduced pressure. The residue is subjected to the magnesia - promoted methanolysis in a manner similar to that described in Example II. It is passed continuously down through an 8 ft. × 1 in. diameter tube packed with one liter of the catalyst described in Example II and maintained at 130°C, against a countercurrent of methanol vapor (2000 grams per 800 gram charge per hour). Methyl acetate and the excess methanol are condensed from the top effluent, and a butanediol-rich trickle phase is taken into the boiler. Analysis of the latter (in a case using a single charge) by quantitative glpc shows the presence of 248 g of 1.4 - butanediol (69% yield in the conversion from allyl acetate), 17 grams of 2-methyl-1,3-propanediol (5% yield), and 47 grams of 1,2-butanediol (13% yield).

Workup

  1. distillationare distilled off under reduced pressure
  2. customdiameter tube packed with one liter of the catalyst
  3. customcondensed from the top effluent
  4. additiona single charge) by quantitative glpc

Sources & evidence

ORD record
ord-29375fc2b3c74f6daf204b96a6513d6f
Source dataset
uspto-grants-1976_09
Patent number
US03981931

Reaction notes

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