Syntheses Of Pentaerythritol Tetrakis(3-dodecylthiopionate)

Pentaerythritol tetrakis(3-dodecylthiopionate) was synthesized by two steps, which 3-dodecylthiopionic acid was first preparaed from a free addition of 1-dodecene withβ-mercaptopropionic acid, and then the intermediate carried out esterification with pentaerythritol to get pentaerythritol tetrakis(3-dodecylthiopionate).In the presence of some initiators, 3-dodecylthiopiopic acid can be conveniently synthesized by heating 1 -dodecene withβ-mercaptopropionic acid, up to a yield of 95 %. Otherwise, various reaction conditions and mechanism for product formation were discussed in detail. It was found that DMSO could be efficiently used as substitution for initiators to promote the reaction to good yield in a high purity.3-Dodecylthiopiopic acid was used as precursor to employ a selective esterifcation with pentaerythritol to form pentaerythritol tetrakis(3-dodecylthiopionate) in a 95 % yield in the presence of para-toluenesulfonic acid catalyst. The reaction conditions and mechanism were discussed. The desired compound could be also obtained in a 90 % yield from pentaerythritol and 3-dodecylthiopionic acid without any separation. The work up was relatively simple, and a small amount of inhibitor additive could improve the quality and purity of the desired product.