Nitrogen → Octanethioic acid, S-(3-(triethoxysilyl)propyl) ester

Participants

Reaction Steps

Into a 12 liter, 3 necked round bottom flask equipped with mechanical stirrer, addition funnel, thermocouple, heating mantle, N2 inlet and temperature controller was charged 1,021 grams of 3-mercaptopropyltriethoxysilane (SILQUEST® A-1891 silane from OSi Specialties, Inc., a subsidiary of Witco Corp. of Greenwich, Conn.), and 433 grams of triethylamine and 3,000 ml hexane. The solution was cooled in an ice bath, and 693 grams of octanoyl chloride was added over a two hour period via the addition funnel. After addition of the acid chloride was complete, the mixture was filtered two times, first through a 0.1 μm filter and then through a 0.01 μm filter, using a pressure filter, to remove the salt. The solvent was removed under vacuum. The remaining yellow liquid was vacuum distilled to yield 1,349 grams of octanoylthiopropyltriethoxysilane as a clear, very light yellow liquid The yield was 87 percent.

Provenance & Evidence