Purification of 2,5-furandicarboxylic acid, dimethyl ester and other esterified products
Inventors
Beheshti Tabar, Iman • Stensrud, Kenneth F. • Hoffman, William Christopher
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Assignees
Member
Glycos Biomedical LtdWe are UK/US entity with a team based in Maryland and North Carolina comprising an expert team that has linked triggers to disease states including TBI and acute injuries associated with radiation, acute lung injury and infection.
We are UK/US entity with a team based in Maryland and North Carolina comprising an expert team that has linked triggers to disease states including TBI and acute injuries associated with radiation, acute lung injury and infection.
Publication Number
US-12624013-B2
Publication Date
2026-05-12
Expiration Date
Abstract
Methods are disclosed for the purification of crude compositions comprising 2,5-furandicarboxylic acid, dimethyl ester (FDME) or other diester derivatives (e.g., dialkyl ester derivatives) of 2,5-furandicarboxylic acid (FDCA), by crystallization. In this regard, certain solvents, and classes of solvents, have been discovered to promote the selective crystallization of FDME over impurities often generated in its production by FDCA esterification and other upstream processing steps. Importantly, certain impurities that are selectively removed include those that would otherwise be detrimental to the color and/or color stability of the purified composition. Other improvements in crystallization reside in the use of techniques such as liquid-liquid extraction and pre-treatment of the crystallization solution by contact with a solid medium.
Core Innovation
The invention relates to purifying a crude composition comprising 2,5-furandicarboxylic acid, dimethyl ester (FDME). The process increases the content of FDME in a purified composition relative to the crude composition by crystallizing FDME from a solvent-based solution phase, and addresses impurities present in the crude composition, including impurities that can adversely affect color and color stability.
In one embodiment, the process forms a biphasic solution comprising an organic phase and a separate aqueous phase using the crude composition, then separates the organic phase from the aqueous phase. The separating step is a continuous liquid-liquid extraction in which one or more impurities are selectively solubilized in the aqueous phase relative to FDME in the crude composition, while FDME is selectively solubilized in the organic phase relative to the one or more impurities.
In another embodiment, the process dissolves the crude composition in a solvent to form a solution of the crude composition, contacts the solution with a solid treatment medium comprising diatomaceous earth and/or activated carbon to provide a treated solution, and then crystallizes from the treated solution to obtain a purified composition with increased FDME content relative to the crude composition. A further enhancement includes a second-stage purification using additional solvent and additional solid treatment medium, with associated crystallization to produce a second-stage purified composition.
Claims Coverage
The document provides two independent claims. One is directed to continuous liquid-liquid extraction followed by crystallization, and one is directed to solid-treatment medium followed by crystallization; both increase FDME content in a purified composition relative to the crude composition.
Continuous liquid-liquid extraction with selective solubilization and crystallization from organic phase
A process for purifying a crude composition comprising 2,5-furandicarboxylic acid, dimethyl ester (FDME) by forming a biphasic solution in an organic phase and a separate aqueous phase, separating the organic phase from the aqueous phase, and crystallizing from the organic phase a purified composition having an increased content of FDME relative to the crude composition; where one or more impurities are selectively solubilized in the aqueous phase relative to FDME, and FDME is selectively solubilized in the organic phase relative to one or more impurities.
Solid treatment medium and crystallization to increase FDME content
A process for purifying a crude composition comprising 2,5-furandicarboxylic acid, dimethyl ester (FDME) by dissolving the crude composition in a solvent to form a solution, contacting the solution with a solid treatment medium comprising diatomaceous earth and/or activated carbon to provide a treated solution, and crystallizing from the treated solution a purified composition having an increased content of FDME relative to the crude composition.
Across the two independent claims, the inventive coverage centers on increasing FDME content by crystallization using either continuous liquid-liquid extraction with selective solubilization of impurities and FDME into different phases, or contacting a solvent solution of the crude with a solid treatment medium comprising diatomaceous earth and/or activated carbon prior to crystallization.
Stated Advantages
Increases the content of FDME in a purified composition relative to the crude composition.
Lightens the color of the purification solution when using a solid treatment medium comprising diatomaceous earth and/or activated carbon.
Provides increased content of FDME in a second-stage purified composition relative to the purified composition and the crude composition.
Documented Applications
Purifying a crude composition comprising 2,5-furandicarboxylic acid dimethyl ester (FDME) to obtain a purified composition having an increased FDME content.
Purifying FDME-containing crude compositions using either continuous liquid-liquid extraction followed by crystallization from the organic phase or using a solid treatment medium (diatomaceous earth and/or activated carbon) followed by crystallization.
Second-stage purification of an FDME-containing purified composition by dissolving in a second-stage solvent, contacting with a solid treatment medium to lighten color, and crystallizing to obtain a second-stage purified composition.
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