Sulfonation of polyhydroxyaromatics
AssigneeAmyris, Inc.
InventorsJohn W Frost, Vu Bui
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Abstract
The present invention provides improved process for the sulfonation of hydroxyaromatics amenable to direct isolation of the sulfonylated hydroxyaromatics in their free-acid forms. The process allows for the recyclization of sulfuric acid and minimizes waste. The starting materials are from a renewal resource, e.g., biomass, and contain detectable 14C up to a 14C content of 0.0000000001% (one part per trillion). The products made include sulfonated catechol, disulfonated pyrogallol and sulfonated protocatechuic acid.
Claims17
A process for preparing a sulfonated hydroxyaromatic compound of formula I:
- wherein:
- X is H or Na;
- R1 is SO3H, SO3Na, CO2H, or CO2Na;
- and R2 is H or OH;
- said process comprising:
- reacting a compound of formula II derived from biomass:
- wherein:
- R1 is H or CO2H;
- and R2 is H or OH;
- with concentrated sulfuric acid at a temperature from room temperature to about 120° C. to form the sulfonated hydroxyaromatic compound of Formula I;
- and separating the sulfonated hydroxyaromatic compound therefrom based on precipitation of the free acid of the sulfonated hydroxyaromatic compound.
A sulfonated hydroxyaromatic compound of formula I:
- wherein:
- X is H or Na;
- R1 is SO3H, SO3Na, CO2H, or CO2Na;
- and R2 is H or OH;
- and wherein all carbon atoms of said sulfonated hydroxyaromatic compound are derived from biomass.
A process for preparing a sulfonated hydroxyaromatic compound of formula I:
- wherein:
- X is H or Na;
- R1 is SO3H, SO3Na, CO2H, or CO2Na;
- and R2 is H or OH;
- said process comprising:
- providing a compound of formula II derived from biomass:
- wherein R1 is H or CO2H, and R2 is H or OH;
- and
- reacting the compound of formula II with concentrated sulfuric acid at a temperature from room temperature to about 120° C. to form the sulfonated hydroxyaromatic compound of Formula I.
Dependencies are inferred from the claim text.