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

HRID 2070219Notes

Reaction equation

[CH2:1]([CH:3]([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4][OH:5])[CH3:2].[CH:10]1([C:20]([O:22]C)=O)[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH3:19])=[O:17])[CH2:12][CH2:11]1>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:20]([CH:10]1[CH2:11][CH2:12][CH:13]([C:16]([O:18][CH2:19][CH:3]([CH2:1][CH3:2])[CH2:6][CH2:7][CH2:8][CH3:9])=[O:17])[CH2:14][CH2:15]1)=[O:22])[CH3:2]

Participants

Conditions

Temperature: 180 °C

Procedure

2-Ethylhexyl alcohol (8.1 mol), dimethyl cyclohexane-1,4-dicarboxylate (DMCD, cis 81.8%, trans 18.2%, SK NJC, 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 81%, trans 19%) was obtained with a purity of 99.3% in the same manner as in Example 1.

Workup

customequipped with a stirrer

Sources & evidence

ORD record: ord-11a887d1871b4249818b7742005d7a79
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08299292B2

Reaction notes

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