Continuous Process for the Production of Taurine from Monoethanolamine

Abstract

Taurine, 2-aminoethane-1-sulfonic acid, is a commercial amino acid manufactured from either ethylene oxide or monoethanolamine (MEA). Taurine is a valuable nutritional additive that is widely used in the production of energy drinks, pet food, nutritional supplements, and infant formula. The industrial production of taurine from MEA is a two-step batch process in which the first step is the reaction of MEA with sulfuric acid to produce the ester 2-aminoethyl hydrogen sulfate (AES) and the second step is the reaction of AES with a sulfite reagent. This report summarizes the results of a study of the fundamental chemistry for this two-step MEA-based chemical route to taurine as well as the application of this fundamental understanding to a process design for a scalable and cost-advantaged continuous process that is capable of commercial-scale production of taurine on a multikiloton scale. In order to maximize taurine yields, the water formed during the first esterification step must be effectively removed to avoid equilibrium limitations on the conversions of MEA and sulfuric acid to form the solid AES intermediate product. For the second AES sulfonation step in aqueous medium, we found that operation above 100 °C under a moderate pressure of an inert gas resulted in significantly higher taurine yields (>80 mol %) compared to those reported in current commercial production technology (typically 55–65 mol %).

General Construction of Asymmetric Amine Ethers via Efficient Transesterification

“…[25] The influence of steric hindrance was subsequently examined. Surprisingly, good yields were obtained for both hydrogen sulfates in the reactions with secondary alcohols (20,21,23,24), superior to conventional etherification method as reported previously. [11] However, tertiary alcohols as substrates are not able to achieve the desired transesterification yields due to the difficulty of weakly nucleophilic reagents with enhanced steric resistances to initiate transesterification reaction [26] and the generation of a large number of symmetric amine ethers as byproducts detected by GC-MS (22,25).…”

“…Such a method successfully avoids the competing intramolecular and homomolecular dehydration processes, as well as the use of high‐risk or expensive reagents and the generation of corrosive waste such as sodium metal, [19] potassium hydride, [20] copper‐containing ligands, [21] and chlorides, [22] etc., and drastically reduces reaction time compared to conventional etherification processes. In this work, we first focused on the esterification of N,N‐dimethylethanolamine or N‐hydroxyethylmorpholine with sulfuric acid (98 wt %) using the method reported by Ma et al., [23] followed by the investigation on the transesterification of hydrogen sulfates and alcohols. In addition, this method can be applied to substrates with electron‐donating, electron‐withdrawing, large steric hindrance, or dihydroxyl groups to prepare various asymmetric amine ethers (Scheme 1).…”

A Key Metabolic Regulator of Bone and Cartilage Health

“…The primary source of taurine for humans is the diet, especially seafood and meat [9]. Human milk or formula compensates for insufficient synthesis in infants and children, which develops until adulthood.…”

Toward Replacing Ethylene Oxide in a Sustainable World: Glycolaldehyde as a Bio‐Based C2 Platform Molecule

“…The reaction mechanism mostly results in high selectivity for ethylenediamines, and not for aminoalcohols, which was explained as a side effect of the high amine ratios needed to induce the sugar C−C bond scission. Another example of an alternative bio‐derived route for an EO application has recently been published by Ma et al [108] . This publication elaborates on the continuous production process of taurine from monoethanolamines.…”

“…Finally, GA production routes have progressed significantly over the years and are catching up to MEG production methods. GA may thus be considered as the true platform chemical to potentially replace EO in an even larger portfolio of commodity and specialty chemicals, [32, 66, 68–72, 81, 108–110] and may form the basis of a novel holistic biorefinery concept.…”