1,2,3-Trimethoxypropane: A Glycerol-Derived Physical Solvent for CO₂ Absorption

Abstract

1,2,3-Trimethoxypropane (1,2,3-TMP) is the trimethyl ether of propane-1,2,3-triol, better known as glycerol, which can be derived from triglycerides originating from either plant or animal sources. Despite its simple structure and the ubiquity of its glycerol precursor, successful synthesis of 1,2,3-TMP was only recently reported in the literature, with studies suggesting it may be a "green" and nontoxic alternative to solvents such as diglyme, a constitutional isomer. However, no thermophysical properties of 1,2,3-TMP have yet been reported. Furthermore, the structure of 1,2,3-TMP is also analogous to polyether solvents used in the Selexol process for removal of CO 2 and other "acid" gases from CH 4 , H 2 , etc. As such, examining the solubility of CO 2 in 1,2,3-TMP is also of interest. This work details our initial studies and characterization of 1,2,3-TMP as a physical solvent for CO 2 absorption, as well as the characterization of its density, viscosity, and vapor pressure with respect to temperature. 1,2,3-TMP exhibits favorable properties, and glycerol-derived triethers warrant deeper consideration as new solvents for CO 2 absorption and other gas treating applications.

New Solvents for CO2 and H2S Removal from Gaseous Streams

“…Another potential physical solvent for CO 2 removal is 1,2,3 trimethoxypropane (1,2,3 TMP) that is characterized by properties comparable to diglyme, a key component of the SELEXOL™ solvent [164]. 1,2,3 TMP is a low-toxicity solvent obtainable with 78% yield and 96% selectivity, without any need for a solvent or heat power, directly from glycerol, which in turn can be derived from vegetable matter or animal fats.…”

“…Currently, this solvent is primarily investigated for applications in reduction of nitro, ester and acid functions [165], transesterification reactions between glycerol and vegetable oils organometallic, C-C coupling and etherification reactions, solvation of metal cations (such as Li + and Na + ) and solubilization of polymers such as polystyrene and polycaprolactone (at high extent), and of cellulose acetate and PVC, at moderate extent [165]. Flowers et al (2017) [164] has shown that TMP has low toxicity, negative skin synthetization and mutagenicity, and low toxicity for the aquatic environment, and has the same molecular weight and similar CO 2 solubility, density and viscosity in comparison with diglyme. When compared to DMPEG (Selexol™ solvent), TMP has 10-15% higher CO 2 solubility (mol/L) at 25-30 • C and more than five times lower viscosity at 25 • C [164].…”

“…Flowers et al (2017) [164] has shown that TMP has low toxicity, negative skin synthetization and mutagenicity, and low toxicity for the aquatic environment, and has the same molecular weight and similar CO 2 solubility, density and viscosity in comparison with diglyme. When compared to DMPEG (Selexol™ solvent), TMP has 10-15% higher CO 2 solubility (mol/L) at 25-30 • C and more than five times lower viscosity at 25 • C [164]. Moreover, the selectivity of CO 2 toward methane absorption reaches values up to 15 [166].…”

Thermal integration of different compression-train configurations for coal-fired power plant with carbon capture

“…Within these methods, the most advanced technology used for CO 2 sequestration is a process involving post-combustion capture using chemical absorption. This technology has been investigated with different absorbents, including ammonia (Linnenberg et al 2012 ), glycerol as a green absorbent (Flowers et al 2017 ), aqueous potassium carbonate (Ghosh et al 2009 ), and alcohol amines such as monoethanolamine (MEA), diethanolamine, and triethanolamine (Suleiman et al 2016 ; Boucif et al 2008 ; Nuchitprasittichai and Cremaschi 2013 ; Cormos et al 2018 ; Wang et al 2011a , 2011b ). Many investigations have been conducted on these types of amines in water solutions and using mixtures of two or more amines.…”

Optimization of the Synthesis of Glycerol Derived Monoethers from Glycidol by Means of Heterogeneous Acid Catalysis

“…Lemaire and co-workers have beautifully reviewed the synthesis of glycerol ethers, starting from both glycerol and platform molecules, such as glycidol, epichlorohydrin and 3-chloropropane-1,2-diol, which can in turn be prepared from glycerol [ 18 ]. As mentioned in this work, scarce data on the production of GMEs is found despite the numerous potential applications of glycerol alkyl ethers [ 19 , 20 , 21 ].…”