Synthesis of 5-aminolevulinic acid with nontoxic regents and renewable methyl levulinate

Zai, Yuxia; Feng, Yunchao; Zeng, Xianhai; Tang, Xing; Sun, Yong; Lin, Lu

doi:10.1039/c9ra01517e

Cited by 9 publications

(4 citation statements)

References 24 publications

(22 reference statements)

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“…In related work, the selectivity toward 5-bromination was improved by brominating ML with CuBr 2 in a mixture of chloroform and methanol (1 : 1), and up to 85 % yield of 5-BrLA was ensured. [208] The side product, 3-bromolevulinic acid (3-BrLA), had to be separated from 5-BrLA (Scheme 16). In the second step of the synthesis, the bromomethyl group was substituted by a nitrogen-containing nucleophile such as azide or phthalimide.…”

Section: La To Angelica Lactone Dimer (Ald)mentioning

confidence: 99%

“…In recent work, the LAEs were found to provide better selectivity toward 5‐BrLA. In related work, the selectivity toward 5‐bromination was improved by brominating ML with CuBr 2 in a mixture of chloroform and methanol (1 : 1), and up to 85 % yield of 5‐BrLA was ensured [208] . The side product, 3‐bromolevulinic acid (3‐BrLA), had to be separated from 5‐BrLA (Scheme 16).…”

Section: Chemical Modification Of the Methyl And Methylene Groups In Lamentioning

confidence: 99%

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Recent Advances in the Value Addition of Biomass‐Derived Levulinic Acid: A Review Focusing on its Chemical Reactivity Patterns

Dutta

Bhat

2021

ChemCatChem

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Levulinic acid (LA) is one of the most prominent biomass‐derived chemical building blocks that can be transformed into specialty chemicals like fuels, solvents, monomers for polymers, plasticizers, surfactants, agrochemicals, and pharmaceuticals. Over the past three decades, an enormous amount of research data have been acquired on the preparation and downstream value addition of LA, and these works have been reviewed. However, considering the astonishing number of publications appearing every year on LA derivatives, the periodical review of recent works focusing on unique aspects of chemistry must be undertaken to critically evaluate the achievements to date, reassess the challenges, and recognize new opportunities. This review discusses the chemical‐catalytic synthesis of various derivatives of LA by focusing on its functionalities and reactivity patterns. Recent literature on some crucial derivatives such as γ‐valerolactone, 4,4’‐diphenolic acid, and ethyl levulinate have been tabulated and discussed. The synthetic interconversion between various derivatives, mechanistic insights, critical analysis of the reaction parameters toward selective preparation of various derivatives, and their potential commercial applications have been elaborated using predominantly heterogeneous catalysts. A critical assessment of the relative advantages and shortcomings of the existing synthetic strategies for various derivatives of LA has been presented to enkindle fresh ideas.

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Section: La To Angelica Lactone Dimer (Ald)mentioning

confidence: 99%

Section: Chemical Modification Of the Methyl And Methylene Groups In Lamentioning

confidence: 99%

Recent Advances in the Value Addition of Biomass‐Derived Levulinic Acid: A Review Focusing on its Chemical Reactivity Patterns

Dutta

Bhat

2021

ChemCatChem

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“…It is widely used in chemical industries because it can be transformed into various products, such as solvents, biodegradable plastics, food additives, and as an intermediate in synthesizing pharmaceutical products [12]. The most used levulinic acid (LA) derivative is aminolevulinic acid, a biodegradable herbicide used in Asia [13]. Other high-value-added compounds obtained from LA are γ-valerolactone (GVL) and 2-methyl-tetrahydrofuran (MTHF), which are green solvents, and methyl levulinate (ML), a promising fuel bioadditive [11,[14][15][16][17].…”

Section: Introductionmentioning

confidence: 99%

Furfural and Levulinic Acid: Synthesis of Platform Molecules from Keggin Heteropolyacid-Catalyzed Biomass Conversion Reactions

da Silva,

Rodrigues,

Batalha

2024

Reactions

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Among the different polyoxometalate compounds, Keggin heteropolyacids have been extensively used as catalysts in several acid-catalyzed reactions, due to their strong strength of Bronsted acidity. These metal–oxygen clusters have a highly versatile structure that allows their conversion to derivatives, which are catalysts that are much more efficient than their precursors, with a greater catalytic activity in a plethora of reactions of industrial interest. Particularly, due to the inevitable exhaustion of fossil sources, reactions to valorize biomass have attracted significant attention, since it is a precious renewable raw material that can provide fine chemicals or fuels, minimizing our dependence on petroproducts. Biorefinery processes can produce platform molecules to achieve this goal. In this review, the recent advances achieved in the development of routes to converting biomass feedstocks to levulinic acid and furfural, which are valuable ingredients in biorefinery processes, using Keggin heteropolyacid catalysts were assessed.

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“…In this case, the introduction of a copper(II) salt into the system deserves attention, since it can be one of the possible sources of anions and an additional oxidizing agent. It is known that copper(II) bromide can be used as a brominating agent in organic synthesis [20][21][22][23][24]. In this regard, a question arises: can copper(II) bromide function as a brominating agent in such a system?…”

Section: Introductionmentioning

confidence: 99%

CuBr2 ЯК БРОМУЮЧИЙ АГЕНТ ПІРАЗОЛЬНИХ ЛІГАНДІВ: СИНТЕЗ КООРДИНАЦІЙНИХ СПОЛУК КУПРУМУ(ІІ) ШЛЯХОМ ОКИСНОГО РОЗЧИНЕННЯ МІДНОГО ПОРОШКУ В ОРГАНІЧНИХ РОЗЧИННИКАХ

Виноградов,

Давиденко,

Павленко

et al. 2023

J. of Chem. and Tech.

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Методом прямого синтезу – окисним розчиненням мідного порошку в присутності CuBr2 і C5H8N2 (3,5-диметил-1H-піразол) було виділено та ідентифіковано три різні типи кристалів. Отримано три нові координаційні спо-луки, а саме триядерну [Cu3(µ3-OH)(µ2-C5H7N2Br)(µ2-Br)3(C5H8N2)5Br]·CHCl3 (де C5H7N2Br – 4-бром-3,5-диметил-піразол) (1) (орторомбічна, Pnma) біядерну [Cu2(µ2-C5H7N2Br)(µ2-Br)(C5H8N2)4Br2]·2CHCl3 (2) (моноклінна, C2/c) та моноядерну [CuBr2(C5H8N2)3] (3) (триклінна, P ). Згідно з результатами рентгеноструктурного ана-лізу, комплекс 1 є триядерним шестичленним циклом, де атоми купруму з’єднані між собою трьома типами містків: μ2-бромід-іонами, молекулою μ2-4-бром-3,5-диметилпіразолу та μ3-гідроксогрупою. Біядерний комп-лекс 2 формується сполученням двох атомів купруму бідентатно-містковим бромід-іоном та містковою моле-кулою бромованого у 4-е положення 3,5-диметилпіразолу. Координаційна сполука 3 є моноядерним триго-нально-біпірамідальним комплексом купруму(II). Відбулося бромування певної частини молекул 3,5-диме-тилпіразолу в 4-е положення піразольного кільця. Згідно з результатами аналізу поверхні Хіршфельда, між-молекулярні контакти H···H мають найбільший внесок у кристалічну упаковку всіх сполук: 66.9 % для 1, 54.4 % для 2 і 66.5 % для 3.

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Synthesis of 5-aminolevulinic acid with nontoxic regents and renewable methyl levulinate

Abstract: Synthesis of 5-aminolevulinic acid (5-ALA) was presented with novel bromination of biobased methyl levulinate (ML), followed by ammoniation and hydrolysis.

Cited by 9 publications

References 24 publications

Recent Advances in the Value Addition of Biomass‐Derived Levulinic Acid: A Review Focusing on its Chemical Reactivity Patterns

Recent Advances in the Value Addition of Biomass‐Derived Levulinic Acid: A Review Focusing on its Chemical Reactivity Patterns

Furfural and Levulinic Acid: Synthesis of Platform Molecules from Keggin Heteropolyacid-Catalyzed Biomass Conversion Reactions

CuBr2 ЯК БРОМУЮЧИЙ АГЕНТ ПІРАЗОЛЬНИХ ЛІГАНДІВ: СИНТЕЗ КООРДИНАЦІЙНИХ СПОЛУК КУПРУМУ(ІІ) ШЛЯХОМ ОКИСНОГО РОЗЧИНЕННЯ МІДНОГО ПОРОШКУ В ОРГАНІЧНИХ РОЗЧИННИКАХ

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