1,3-Propanediol → 1,3-Propanediol

HRID 379356Notes

Reaction equation

HRID 379356 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]=[O:5].[CH2:6]([OH:10])[CH2:7][CH2:8][OH:9]>>[OH:5][CH2:4][CH2:3][CH:2]=[O:1].[CH2:6]([OH:10])[CH2:7][CH2:8][OH:9].[OH:5][CH2:4][CH2:3][CH:2]1[O:9][CH2:8][CH2:7][CH2:6][O:1]1

Participants

5

Reactant 2

HCID 104421,3-PropanediolHCID 75049Reuterin

Product 3

HCID 104421,3-PropanediolHCID 75049ReuterinHCID 2319742-(1,3-Dioxan-2-yl)ethanol

Procedure

When hydrogenating 3-hydroxypropanal to 1,3-propanediol on a large industrial scale, it is vital, with regard to the economic viability of the hydrogenation process and the quality of the product, for conversion and selectivity to be as close as possible to 100%. The 1,3-propanediol may be separated from the water as well as remaining 3-hydroxypropanal and secondary products contained in the product stream by distillation after the hydrogenation. However, this distillative separation is rendered very difficult by residual 3-hydroxypropanal and secondary products and may even become impossible due to reactions between the residual 3-hydroxypropanal and 1,3-propanediol to yield acetals such as 2-(2′-hydroxyethyl)-1,3-dioxane (HED), which have a boiling point close to the boiling point of 1,3-propanediol. Thus, the lower the conversion and selectivity, the poorer the achievable product quality.

Workup

  1. customas close as possible to 100%
  2. customThe 1,3-propanediol may be separated from the water as well
  3. distillationcontained in the product stream by distillation after the hydrogenation
  4. customHowever, this distillative separation

Sources & evidence

ORD record
ord-464ddb1f40f3485388c46fb68041527a
Source dataset
uspto-grants-2001_10
Patent number
US06297408B1

Reaction notes

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