Modeling of Toluene Sulfonic Acid Catalyzed Oxide Addition Reaction for Soy-Based Polyol

Abstract

Polyol oligomers formed from reactions of mono-, di-, and triethylene glycols with epoxidized soybean oil were synthesized and the reaction conversions were modeled. The data verified the effectiveness of a model that is based on the simultaneous solution of eight ordinary differential equations. In addition, the data demonstrated that di-and triethylene glycols produced lower viscosity oligomers than monoethylene glycol. Since the model is fundamentally based, it provides insight into the reaction mechanisms and allows for simulation of reaction conditions with reasonable extrapolation. Within the accuracy of the data, the reaction rate coefficients for all alcohol and epoxy moieties were equal, independent of the molecule to which they were attachedreaction rates varied based only on temperature and dilution of reacting moieties. The model provides an effective means to simulating concentration, viscosity, and temperature profiles including estimates of degrees of polymerization, which are dependent on a parameter related to inter versus intra-oligomerization.

Natural Oil Polyol from High-Oleic Palm Oil─Reaction Kinetics and Monitoring Using Near-Infrared Spectroscopy

“…The obtained kinetic parameters were similar to those reported in the oxirane ring opening of epoxidized soybean oil with EG 32 and in the oxirane cleavage of epoxidized palm oil with carboxylic acids. 66,67 Nonetheless, the obtained energy of activation was lower due to the use of more active catalysts (i.e., H 2 SO 4 ) compared with those previously studied (i.e., selfcatalyzed, toluene sulfonic acid).…”

“…Mixtures of diols with alcohols or water are also used because the lasts enable formation of sterically hindered secondary hydroxyl groups that are less susceptible to intermolecular ring opening, thus reducing undesired cross-linking and high viscosity of the obtained polyol. 31 Despite the large number of reports on NOP production, there is only one kinetic study on the hydroxylation of epoxidized oils; 32 this describes the reaction between soybean oil with mono-, di-, and triethylene glycols. In the case of palm-based or HOPO-based polyols, there are no kinetic studies in the open literature.…”

Impact of the maximum foam reaction temperature on reducing foam shrinkage

“…A205 Gels -A205 polyol is synthesized by reaction of epoxidized soybean oil with ethylene glycol in the presence of toluene sulfonic acid in a controlled temperature of 161 C. The epoxy number of A205 is around 1.3 and its water content is 0.2%. 15 The amount of A205 is calculated so that it has the same total moles of hydroxyl functional group as the control.…”

Curing behavior of epoxidized soybean oil with biobased dicarboxylic acids

“…In corporation of high reactive double bond by reacting with acrylic acid or allyl alcohol provides an efficient way for ESO to produce polymers via free radical polymerization [14][15][16] . In addition, suitable chemical reactions are able to transform ESO to polyols towards fabrication of polyurethanes [17][18][19] .…”