Tetrahydrofuran → Methylpropanediol

HRID 1645464Notes

Reaction equation

HRID 1645464 reaction equation
C(OCCCCO)(=O)C.O1CCCC1.[C:15]([O:18][CH2:19][CH:20]([CH3:23])[CH2:21][OH:22])(=[O:17])[CH3:16]>[W]=O.C(O)(=O)C>[C:15]([O:18][CH2:19][CH:20]([CH3:23])[CH:21]=[O:22])(=[O:17])[CH3:16].[CH3:23][CH:20]([CH2:21][OH:22])[CH2:19][OH:18]

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 101032094-Hydroxybutyl acetateHCID 103745003-Acetoxy-2-methylpropan-1-ol

Product 2

HCID 75103MethylpropanediolHCID 109862492-Formyl-2-methylethyl acetate

Reagents, catalysts & solvents 2

HCID 139486OxotungstenCatalystHCID 176Acetic AcidSolvent

Procedure

Alternatively, at least a portion of the 4-acetoxybutyraldehyde reaction product may be preferably converted to produce tetrahydrofuran (THF). Preferably, the 4-acetoxybutyraldehyde is hydrogenated to produce 4-acetoxybutanol, which then is dehydroacetoxylated to produce THF. The hydrogenation to produce 4-acetoxybutanol is preferably conducted according to the conditions described above. The 4-acetoxybutanol can then undergo a dehydroacetoxylation reaction to produce THF and acetic acid. The dehydroacetoxylation step is preferably performed at temperatures in the range of from 20 to 300° C. in the presence of a dehydroacetoxylation catalyst, such as silica, silica-alumina, and/or tungsten oxide. A final hydrolysis step may be performed to convert any 3-acetoxy-2-methylpropanol, formed by the hydrogenation of 3-acetoxy-2-methylpropionaldehyde, to 2-methyl-1,3-propanediol (MPD)

Workup

  1. customa dehydroacetoxylation reaction
  2. customA final hydrolysis step

Sources & evidence

ORD record
ord-f84d89875c1b48b8a3c40caa0b57b1d6
Source dataset
uspto-grants-2012_02
Patent number
US08124805B2

Reaction notes

Loading…