Continuous ion exchange and esterification of fermented malonic acid
AssigneeLygos, Inc.
InventorsNicholas Ohler, Johan Van Walsem, Chi Le, Kelvin Shing, Daniel Blackburn, Owen Budavich
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Abstract
Provided herein is a process of ion exchange comprising malonic acid or a salt thereof and a cation or an anion cation exchange resin. The ion exchange is accomplished, e.g., and without limitation by continuous ion exchange. A valve and resin bed configuration is useful in this regard. The malonic acid separated by ion exchange is esterified, e.g., by Fisher esterification by using an acid and an alcohol.
Claims26
A process of ion exchange comprising:
- contacting malonic acid or a salt thereof and a cation or anion exchange resin
- wherein the cation exchange resin is regenerated periodically with an acid into the protonated form so that the malonic acid salt is protonated while contacting the resin and reports to the raffinate stream as an aqueous malonic acid solution free of a cation and the cation is adsorbed onto the resin to be eluted as the corresponding salt of the regenerating acid, or
- wherein the anion exchange resin is regenerated periodically with an acid so that the malonic acid that has previously been adsorbed on the resin is eluted from the resin and the conjugate base of the regenerating acid is adsorbed on the resin ready for the next cycle
- wherein the ion exchange is accomplished by continuous ion exchange, using a resin bed system configuration designed to simulate a resin bed moving countercurrent-wise to the fluid flow.
A process according to claim 10, in which the acid used for regeneration is aqueous sulfuric acid.
A process in which a diester of malonic acid is produced comprising the following elements:
- a. fermentation to generate malonate as a salt;
- b. separation of crude liquid malonate from cells;
- c. optionally, ultrafiltration or nanofiltration to separate malonate from impurities with high molecular weight;
- d. crystallization of solid malonic acid from liquor;
- e. filtration of solid malonic acid from liquor, and optionally drying of solid malonic acid crystals;
- f. dissolution of the resulting crystals in alcohol;
- g. contacting the resulting solution with solid catalyst to generate a solution containing diester, monoester, and residual malonic acid;
- h. optionally, distillation of the resulting solution to remove water as well as alcohol;
- i. optionally, mixing the resulting material with alcohol and contacting it with solid catalyst to generate a solution containing diester, monoester, and residual malonic acid;
- j. optionally, repeating steps h and i one or more times to maximize the amount of diester generated;
- k. separating the diester product from other remaining components by fractional distillation;
- l. recycling distilled alcohol after separating it from water by distillation, or swing adsorption of water onto an adsorbent, or pervaporation, or vapor permeation.
Dependencies are inferred from the claim text.