Azobisisobutyronitrile → Sodium 3,4-bis[(2-ethylhexyl)oxycarbonyl]cyclohexanesulfonate

HRID 41836Notes

Reaction equation

[CH2:1]([CH:3]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:4][O:5][C:6]([CH:8]1[CH2:13][CH:12]=[CH:11][CH2:10][CH:9]1[C:14]([O:16][CH2:17][CH:18]([CH2:23][CH3:24])[CH2:19][CH2:20][CH2:21][CH3:22])=[O:15])=[O:7])[CH3:2].[S:29]([O-:32])([OH:31])=[O:30].[Na+:33].N(C(C)(C)C#N)=NC(C)(C)C#N>C(O)(C)C>[CH2:23]([CH:18]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:17][O:16][C:14]([CH:9]1[CH:8]([C:6]([O:5][CH2:4][CH:3]([CH2:1][CH3:2])[CH2:25][CH2:26][CH2:27][CH3:28])=[O:7])[CH2:13][CH2:12][CH:11]([S:29]([O-:32])(=[O:31])=[O:30])[CH2:10]1)=[O:15])[CH3:24].[Na+:33]

Participants

Conditions

Temperature: 81.5 °C

Procedure

In the stream of an argon gas, 80 g of 4-cyclohexene-1,2-dicarboxylic di(2-ethylhexyl)ester (manufactured by Tokyo Chemical Industry Co., Ltd.) and 900 mL of isopropyl alcohol was placed. 660 mL of an aqueous solution of 42.3 g of sodium hydrogen sulfite (manufactured by Wako Pure Chemical Industries, Ltd.) was added. The resulting solution was heated to a reflux temperature, and stirred at 80 to 83° C. for 16 hours. During this stirring, every one hour from the start to 1 to 5 hours after the start of refluxing, as well as after 9 hours and 10 hours, 1.66 g of 2,2′-azobis(isobutyronitrile) (manufactured by Wako Pure Chemical Ltd.) was added. After cooling to room temperature, the reaction liquid was concentrated under reduced pressure.

Workup

temperatureThe resulting solution was heated to a reflux temperature
temperatureDuring this stirring, every one hour from the start to 1 to 5 hours after the start of refluxing
waitas well as after 9 hours
temperatureAfter cooling to room temperature
customthe reaction liquid
concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record: ord-43f62bcafd254a00bdc53b94ba711a8f
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08535812B2

Reaction notes

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