1-Butanol → HCID 22218522, compound

HRID 596929Notes

Reaction equation

HRID 596929 reaction equation
C(O)(=O)C=C.[CH2:6]([OH:10])[CH2:7][CH2:8][CH3:9].[CH2:11]([O:15][C:16](=[O:19])[CH:17]=[CH2:18])[CH2:12][CH2:13][CH3:14].C(OCCCC)CCC>O>[CH2:6]([OH:10])[CH2:7][CH2:8][CH3:9].[CH2:11]([O:15][C:16](=[O:19])[CH:17]=[CH2:18])[CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 2631-Butanol3×HCID 6581Acrylic Acid4×HCID 8846Butyl AcrylateHCID 8909Butyl ether

Product 1

HCID 22218522HCID 22218522, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

The reaction temperature was increased to 140° C and was accordingly outside the temperature range described herein. The molar ratio of acrylic acid to n-butanol of 1:1.7 and the working pressure of 7 atmospheres gauge used in Example 1 remained unchanged. 102 g of acrylic acid and 178 g of n-butanol were passed per hour through the reactor. The acrylic acid conversion rate was 85.1%. 280 g of reaction product containing 52.9 weight % of butylacrylate, 5.35 weight % of acrylic acid, 31.45 weight % of n-butanol, 7.85 weight % of water, 0.35 weight % of dibutylether and 2.1 weight % of residue was obtained. The butanol/butylacrylate-azeotrope obtained at the head of third distillation column 17 contained 0.5 weight % of dibutylether and was, therefore, not recycled to the reactor, 146 g/h, including the butylacrylate fraction contained in the azeotrope, of butylacrylate contaminated with 0.3 weight % of dibutylether was obtained. This corresponded to yield of 94.4%, based on the acrylic acid converted. The catalyst performance was 942 g of butylacrylate per kg of catalyst per hour.

Workup

  1. custom280 g of reaction product
  2. customwas obtained

Sources & evidence

ORD record
ord-c7b6aae7652d465fa078ffb8f34fe077
Source dataset
uspto-grants-1977_03
Patent number
US04012439

Reaction notes

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