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Formaldehyde → Glycolic Acid

HRID 74142
Notes
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Reaction equation

HRID 74142 reaction equation
[C]=O.C=O.[C:5]([OH:9])(=[O:8])[CH2:6][CH3:7].C([O:14][CH2:15][C:16]([OH:18])=[O:17])(=O)CC>O>[C:16]([OH:18])(=[O:17])[CH2:15][OH:14].[C:5]([OH:9])(=[O:8])[CH2:6][CH3:7]
ParticipantsProcedureSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 1032Propionic Acid2×HCID 12136775(Propionyloxy)acetic acidHCID 178418416HCID 178418416, compound

Product 2

HCID 757Glycolic AcidHCID 1032Propionic Acid

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent
2×

Procedure

FIGS. 1 and 2 present two, non-limiting embodiments or the instant invention described herein in detail. In a first embodiment of the invention as laid out in FIG. 1, Carbon Monoxide Stream 1, Aqueous Formaldehyde Stream 2, and Propionic Acid Stream 3 are fed to Hydrocarboxylation Reactor 50 which comprises a fixed bed, solid catalyst (not shown). The Effluent Stream 4 comprises the esters of glycolic and propionic acid including 2-propionoxyacetic acid and (2′-(propionyloxy)acetoxyacetic acid. Effluent Stream 4 and Water Stream 8 are fed to Hydrolyzer 55. Hydrolyzer 55 is operated at sufficient temperature, pressure, and residence time to produce Hydrolyzed Mixture Stream 9 comprising glycolic acid, propionic acid, and water. Hydrolyzed Mixture Stream 9 is extracted with Hydrophobic Solvent Stream 11, such as methyl tertiary-butyl ether, in Extractor 60, to produce Organic Extract Stream 10 and Aqueous Raffinate Stream 12. Organic Extract Stream 10 can be separated into Propionic Stream 3 and Hydrophobic Solvent Stream 11 in Separator 70. Separator 70 can be, for example a distillation column. Propionic Acid Stream 3 is recycled to Hydrocarboxylation Reactor 50 and Hydrophobic Solvent Stream 11 is recycled to Extractor 60.

Sources & evidence

ORD record
ord-8b130d8ddbf74773a2643cdd973addf3
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08829234B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes