Dimethyl 1,4-cyclohexanedicarboxylate → Bis(2-ethylhexyl) cyclohexane-1,4-dicarboxylate

HRID 2070222Notes

Reaction equation

[CH2:1]([CH:3]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4][OH:5])[CH3:2].CO[C:12]([CH:14]1[CH2:19][CH2:18][CH:17]([C:20]([O:22][CH3:23])=[O:21])[CH2:16][CH2:15]1)=[O:13]>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4]>[CH2:1]([CH:3]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4][O:5][C:12]([CH:14]1[CH2:15][CH2:16][CH:17]([C:20]([O:22][CH2:23][CH:3]([CH2:1][CH3:2])[CH2:6][CH2:7][CH2:8][CH3:9])=[O:21])[CH2:18][CH2:19]1)=[O:13])[CH3:2]

Participants

Conditions

Temperature: 180 °C

Procedure

2-Ethylhexyl alcohol (8.1 mol), dimethylcyclohexane-1,4-dicarboxylate (DMCD, cis 1.7%, trans 98.3%, Eastman, 3.0 mol) and tetraisopropyl titanate catalyst (0.85 g) were added to a 2.5 L reactor equipped with a stirrer and two condensers and heated to 180° C. Di(2-ethylhexyl)cyclohexane-1,4-dicarboxylate (cis 3%, trans 97%) was obtained with a purity of 99.8% in the same manner as in Example 1.

Workup

customequipped with a stirrer

Sources & evidence

ORD record: ord-a210ae1ce1ce423aa4a6b16130e602bf
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299292B2

Reaction notes

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