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Synthesis of Sulfonated Aryl Alkyl Ether Monomers in Cost Effective Solvents

IP.com Disclosure Number: IPCOM000250326D
Publication Date: 2017-Jun-28
Document File: 4 page(s) / 101K

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4772733: PATENT [+3]

Abstract

This paper describes the synthesis of sulfonated aromatic monomers. More specifically, this paper will focus on the synthesis of allyl and methallyl ethers of sulfonated pyranine derivatives in cost effective solvents or solvent blends of methanol, ethanol, isopropanol and water. These solvents are both cost effective from a chemical acquisition facet and from an operational facet. Intrinsic properties of these readily available solvents include relatively low boiling point for easy removal, arguably better safety profile or both. Past publications describe the synthesis of these ethers using solvent/base combinations that are difficult to scale up to commercial quantities, expensive due to solvent costs, or present unnecessary health hazards.

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Synthesis of Sulfonated Aryl Alkyl Ether Monomers in Cost Effective Solvents

Abstract:  This paper describes the synthesis of sulfonated aromatic monomers.  More specifically, this paper will focus on the synthesis of allyl and methallyl ethers of sulfonated pyranine derivatives in cost effective solvents or solvent blends of methanol, ethanol, isopropanol, acetone and/or water. These solvents are both cost effective from a chemical acquisition facet and from an operational facet.   Intrinsic properties of these readily available solvents include relatively low boiling point for easy removal, arguably better safety profile or both.  Past publications describe the synthesis of these ethers using solvent/base combinations that are difficult to scale up to commercial quantities, expensive due to solvent costs, or present unnecessary health hazards.

Two examples of monomers used in polymers include sodium salts of the allyl ether of hydroxypyrenetrisulfonic acid, with the most common isomer being 8-Hydroxypyrene-1,3,6-trisulfonic acid (1), and sodium salts of the allyl ether of hydroxybenzenesulfonic acid, with the most common isomer being 4-allyloxybenzene sulfonic acid (2).  The structures of 1 and 2 can be seen in Figure 1 below.  Published syntheses for 1 include a synthesis using dimethylsulfoxide (DMSO) as a solvent for this reaction.  After the reaction is complete, it is isolated by vacuum distillation of DMSO or precipitation in acetone.  DMSO is relatively expensive and has a boiling point of 189 °C, making hard to remove by vacuum distillation.  By comparison methanol, ethanol, isopropanol and water have significantly lower boiling points as shown in Table 1. While mixtures of methanol/water and acetone/water do not form azeotropic mixtures, solvent mixtures of ethanol/water and isopropanol/water will form an azeotropic solution having a boiling point somewhere between that of the two components.  If conducting the reaction at reflux, this allows for the temperature of the reaction to be controlled during reflux by choosing the appropriate mixture of alcohol and water.

Table 1: Boiling points of solvents

Moreover, DMSO has a unique property that allows DMSO, and compounds solubilized in it, to penetrate skin and epidermal layers.  Historically some medicines have been administered epidermally using DMSO.  There is anecdotal evidence that once DMSO is absorbed through the skin, it can be tasted in the mouth shortly after, as it circulates throughout the body.  This can cause concern if a reaction mixture containing hazardous compounds - including reagents, intended reaction products or reaction byproducts – were to come in contact with persons while conducting a synthesis using DMSO.  

A synthesis of 2 describes the use of acetone as a solvent.  Acetone is relatively safe to handle.  At the time of this writing, the spot price of acetone ($0.43/lb) is higher than methanol ($0.17/lb) and isopropanol ($0.42/lb).

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