[C]=O.C=O.[C:5]([OH:11])(=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9].C([O:18][CH2:19][C:20]([OH:22])=[O:21])(=O)CCCC>O>[C:20]([OH:22])(=[O:21])[CH2:19][OH:18].[C:5]([OH:11])(=[O:10])[CH2:6][CH2:7][CH2:8][CH3:9]
Use of a hydrophobic solvent for extraction of the carboxylic acid from the hydrolyzed mixture is necessary if the carboxylic acid and aqueous glycolic acid does not phase separate and may be helpful to improve the separation even if not required to form two phases. In a second embodiment of the invention as set forth in FIG. 2, Carbon Monoxide Stream 1, Aqueous Formaldehyde Stream 2, and Valeric 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 valeric acid including 2-valeryloxyacetic 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, valeric acid, and water. Hydrolyzed Mixture Stream 9 is separated into two phases in Decanter 65. The organic phase is recycled to Hydrocarboxylation Reactor 50 as Valeric Acid Stream 3. Aqueous Glycolic Acid Stream 12 exits Decanter 65 and is fed, along with First Ethylene Glycol Stream 13 to Esterification Unit 80. Water Stream 14 and Glycolate Ester Oligomer Stream 15 exit Esterification Unit 80. Glycolate Ester Oligomer Stream 15 is hydrogenated using Hydrogen Stream 16 in Hydrogenation Unit 90. Hydrogenation Unit 90 produces Second Ethylene Glycol Stream 17 which can be split into Ethylene Glycol Product Stream 18 and First Ethylene Glycol Stream 13 which is recycled to Esterification Unit 80.
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