Natural Oil Polyols using Self-Metathesis

Patent Title: POLYOLS FORMED FROM SELF-METATHESIZED NATURAL OILS AND THEIR USE IN MAKING POLYURETHANE FOAMS

 Number/Link: US2017/0291983

Applicant/Assignee:  Trent Univ.

Publication date: 12 october 2017

Gist”: NOPs from self-metathesized soy oils

Why it is interesting: The use of metathesis chemistry to modify natural oils before converting them to polyols has been discussed before in this blog:  see e.g. US2015/0337073, to the same applicant, which relates to cross-metathesis of natural oils using (e.g.) 1-butene. The current case is about self-metathesis of unsaturated natural oils, resulting in ‘metathesis oligomers’ which are then (partially) epoxidated and hydroxylated to prepare the polyols. In the examples soybean oil is turned into polyols with OH values between about 100 and 250, which are used to make flexible foams with densities of more than 150 kg/m³.

Oligomer from self-metathesis of unsaturated triglycerid


Natural Oil Polyols Using Metathesis Chemistry

Patent Title: METATHESIZED TRIACYLGLYCEROL POLYOLS FOR USE IN POLYURETHANE APPLICATIONS AND THEIR RELATED PROPERTIES

 Number/Link: US2015/0337073

Applicant/Assignee: Trent University

Publication date: 26-11-2015

Gist”: Palm oil is metathesized before hydroxylation.

Why it is interesting: Natural-oil based polyols (NOPs) prepared from unsaturated plant oils are well known in the PU industry. In this case however, the oil is first modified into a ‘metathesized triacylglycerol’ by cross-metathesis using (e.g.) 1,2-butene and an appropriate catalyst. The result is a complex mixture of triglycerids, the unsaturations of which are then epoxidized and hydrolyzed into the final polyol.  In the examples palm-oil metathezised triacylglycerol (PMTAG) is compared to a commercially available soy-oil polyol when used to perpare both flexible and rigid foams. While the chemistry is interesting there does not appear to be much advantage to this type of NOP.

Metathesis reaction of triolein with butene

Metathesis reaction of triolein with butene