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Kinetic Study on the Preparation of Fumaric Acid from Maleic Acid by Batch Noncatalytic Isomerization.

ABSTRACT: In recent years, the increase in demand for fumaric acid from industry has resulted in an increased need for a high-selectivity process for the conversion of maleic acid to fumaric acid. A highly selective conversion of fumaric acid was achieved without a catalyst by a simple one-step hydrothermal reaction. In addition, the competitive conversion of maleic acid, fumaric acid, and malic acid was first systematically investigated in detail without using a catalyst. The products were characterized by X-ray diffraction and Fourier transform infrared, which demonstrated that the product was fumaric acid. The highly selective conversion of fumaric acid was achieved, and the yield of fumaric acid could reach 92%. Furthermore, a reaction kinetic model was put forward to study the competitive transformation process. The kinetic model predictions were found to agree well with the experimental data. The kinetic parameters were used to explain the changes in the content of every substance at different reaction temperatures and reaction times. In addition, the initial maleic acid concentration in the reaction was also considered as an influencing factor. These results can facilitate the conditional control and product control of industrial processes for the production of fumaric acid or malic acid using latter without a catalyst.

SUBMITTER: Chen W

PROVIDER: S-EPMC6545549 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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Kinetic Study on the Preparation of Fumaric Acid from Maleic Acid by Batch Noncatalytic Isomerization.

Chen Wangmi W Chen Xiaoting X Yi Shouzhi S

ACS omega 20190508 5

In recent years, the increase in demand for fumaric acid from industry has resulted in an increased need for a high-selectivity process for the conversion of maleic acid to fumaric acid. A highly selective conversion of fumaric acid was achieved without a catalyst by a simple one-step hydrothermal reaction. In addition, the competitive conversion of maleic acid, fumaric acid, and malic acid was first systematically investigated in detail without using a catalyst. The products were characterized ...[more]

PMID: 31172038

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Project description:ObjectiveTo test the hypothesis that dimethyl fumarate (DMF, Tecfidera) elicits different biological changes from DMF combined with monoethyl fumarate (MEF) (Fumaderm, a psoriasis therapy), we investigated DMF and MEF in rodents and cynomolgus monkeys. Possible translatability of findings was explored with lymphocyte counts from a retrospective cohort of patients with MS.MethodsIn rodents, we evaluated pharmacokinetic and pharmacodynamic effects induced by DMF and MEF monotherapies or in combination (DMF/MEF). Clinical implications were investigated in a retrospective, observational analysis of patients with MS treated with DMF/MEF (n = 36).ResultsIn rodents and cynomolgus monkeys, monomethyl fumarate (MMF, the primary metabolite of DMF) exhibited higher brain penetration, whereas MEF was preferentially partitioned into the kidney. In mice, transcriptional profiling for DMF and MEF alone identified both common and distinct pharmacodynamic responses, with almost no overlap between DMF- and MEF-induced differentially expressed gene profiles in immune tissues. The nuclear factor (erythroid-derived 2)-like 2 (Nrf2)-mediated oxidative stress response pathway was exclusively regulated by DMF, whereas apoptosis pathways were activated by MEF. DMF/MEF treatment demonstrated that DMF and MEF functionally interact to modify DMF- and MEF-specific responses in unpredictable ways. In patients with MS, DMF/MEF treatment led to early and pronounced suppression of lymphocytes, predominantly CD8+ T cells. In a multivariate regression analysis, the absolute lymphocyte count (ALC) was associated with age at therapy start, baseline ALC, and DMF/MEF dosage but not with previous immunosuppressive medication and sex. Furthermore, the ALC increased in a small cohort of patients with MS (n = 6/7) after switching from DMF/MEF to DMF monotherapy.ConclusionsFumaric acid esters exhibit different biodistribution and may elicit different biological responses; furthermore, pharmacodynamic effects of combinations differ unpredictably from monotherapy. The strong potential to induce lymphopenia in patients with MS may be a result of activation of apoptosis pathways by MEF compared with DMF.

Dataset Information

Kinetic Study on the Preparation of Fumaric Acid from Maleic Acid by Batch Noncatalytic Isomerization.

Publications

Kinetic Study on the Preparation of Fumaric Acid from Maleic Acid by Batch Noncatalytic Isomerization.

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