Process for converting disulfides to conversion products and process for producing cysteic acid
a technology of conversion products and process, applied in the field of process for converting disulfides to conversion products and process for producing cysteic acid, can solve the problems of high production cost of cysteic acid, high production cost, and high production cos
Pending Publication Date: 2022-11-17
FXI INC LTD
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Benefits of technology
The process achieves high-purity cysteic acid production in high yields, is cost-effective, and safe for large-scale commercial applications, eliminating the need for hazardous chemicals and complex purification protocols.
Problems solved by technology
The production costs in making cysteic acid, however, is high (˜$200 / kg), as compared to cystine (˜$30 / kg) from which it is commonly synthesized.
The high production costs are largely due to state-of-the-art methods of making cysteic acid.
The cost of molecular bromine, its safety, and post-synthesis work-up protocols render this method too time intensive and potentially hazardous.
On large scales, however, the in situ formation of bromine from HBr is hazardous.
The oxidizing agent tert-butyl hypochlorite, however, is costly and hazardous on a large scale due to its decomposition in water with subsequent generation of chlorine gas.
Electrochemical methods for producing cysteic acid are also known, but are typically not practical for large-scale commercial applications.
Each of these known methods are inefficient, require high amounts of oxidizing agents, are not useful for large-scale production, generate hazardous materials, and are too costly.
The oxidation of cystine is not unique, however, as the oxidation of other compounds having disulfide bonds to useful materials is costly, inefficient, and potentially hazardous by known methods.
Method used
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[0037]Cystine, glacial acetic acid (CH3CO2H), nitric acid (HNO3), formic acid (HCO2H), and hydrogen peroxide solution were obtained commercially. The crude materials of the reaction product (e.g., the conversion product) for the examples and comparative examples below were analyzed by 500 MHz 1H NMR, using suitable amounts of D2O as the deuterated solvent. The 1H NMR spectra for the examples and comparative examples, as well as the 1H NMR spectrum of commercially available cysteic acid, are shown in FIG. 3.
[0038]Example 1: Cystine powder (˜0.1 g) was dissolved in a mixture of glacial acetic acid (˜30 mL) and ˜20 mL H2O2 (30% (w / w) in H2O) by stirring for 4 h at ˜25° C. The excess of peracetic acid was slowly evaporated by stirring on a hot plate at about 40° C. to about 45° C. and the residue analyzed by 1H NMR. The 1H NMR spectrum of the residue is shown in FIG. 3 as Ex. 1. The yield of L-cysteic acid was >99% and the percent conversion of cystine was determined to be >99%. The res...
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Abstract
Embodiments of the present disclosure generally relate to processes for converting disulfides to conversion products and to processes for producing cysteic acid. In an embodiment, a process for converting cystine to a conversion product is provided. The process include introducing an organic peroxide and water to cystine to form a mixture. The process further includes reacting the mixture, under conversion conditions, to form the conversion product, wherein the conversion product comprises cysteic acid, an amount of cysteic acid in the conversion product is greater than about 90 wt % based on a total weight of the conversion product, and the conversion conditions comprise a conversion temperature from about 15° C. to about 50° C. The process further includes heating the conversion product to remove the organic peroxide.
Description
CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application is a continuation of U.S. patent application Ser. No. 17 / 319,921, filed May 13, 2021, now U.S. Pat. No. 11,401,239, which claims priority to U.S. Provisional Patent Application No. 63 / 090,739, filed Oct. 13, 2020, both of which are incorporated herein by reference in their entirety.BACKGROUNDField[0002]Embodiments of the present disclosure generally relate to processes for converting disulfides to conversion products and to processes for producing cysteic acid.Description of the Related Art[0003]Cysteic acid, also known as 3-sulfo-L-alanine, is an organic compound having the formula HO3SCH2CH(NH2)CO2H. Cysteic acid is a nontoxic and nonallergenic physiological compound found in, e.g., platelets and leukocytes of human and animal blood. Cysteic acid has myriad applications, including pharmaceutical and water-decontamination uses. For example, cysteic acid has efficacy in treating ichthyotic conditions, body odor, hangovers...
Claims
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IPC IPC(8): C07C303/16
CPCC07C303/16C07C309/18
InventorSTANULIS, ANDRIUSBARRON, ANDREW R.
OwnerFXI INC LTD