Synthetic routes to 3,4,5-trimethoxybenzaldehyde (review)

Erofeev, Yu. V.; Afanas'eva, V. L.; Глушков, Р. Г.

doi:10.1007/bf00765001

Cited by 19 publications

(14 citation statements)

References 26 publications

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“…Syringaldehyde is a possible precursor to 3,4,5-trimethoxybenzaldehyde and pharmaceuticals derived from the latter, and it is not produced in industry by lignin oxidation. Synthetic approaches to syringaldehyde production are more costly compared to vanillin [ 16 ], while production of the former by hardwood lignin oxidation can be cheaper compared to lignin-derived vanillin. This is because of a higher yield of syringaldehyde from hardwood lignins (up to 30 wt.…”

Section: Discussionmentioning

confidence: 99%

“…Syringaldehyde is potentially the most valuable product among the discussed ones, serving as a precursor to 3,4,5-trimethoxybenzaldehyde the price of which exceeds 25 USD/kg. 3,4,5-trimethoxybenzaldehyde is probably ordinarily synthesized from vanillin [ 16 ] and is used in production of pharmaceuticals and other speciality chemicals.…”

Section: Development Prospects For the Technology Of The Aromatic mentioning

confidence: 99%

“…Active research is devoted to the vanilloid class of drugs, e.g., capsaicin—a component of cayenne pepper and the basis of medical topical formulations [ 13 , 14 , 15 ]. Syringaldehyde can be used for the synthesis of trimethoxybenzaldehyde, trimethoprim and other pharmaceuticals [ 16 ]. Syringaldehyde can also be transformed into substituted anthraquinones—the catalysts for improving the processes of alkaline delignification [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

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Catalytic Oxidation of Lignins into the Aromatic Aldehydes: General Process Trends and Development Prospects

Tarabanko

2017

IJMS

120

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This review discusses principal patterns that govern the processes of lignins’ catalytic oxidation into vanillin (3-methoxy-4-hydroxybenzaldehyde) and syringaldehyde (3,5-dimethoxy-4-hydroxybenzaldehyde). It examines the influence of lignin and oxidant nature, temperature, mass transfer, and of other factors on the yield of the aldehydes and the process selectivity. The review reveals that properly organized processes of catalytic oxidation of various lignins are only insignificantly (10–15%) inferior to oxidation by nitrobenzene in terms of yield and selectivity in vanillin and syringaldehyde. Very high consumption of oxygen (and consequentially, of alkali) in the process—over 10 mol per mol of obtained vanillin—is highlighted as an unresolved and unexplored problem: scientific literature reveals almost no studies devoted to the possibilities of decreasing the consumption of oxygen and alkali. Different hypotheses about the mechanism of lignin oxidation into the aromatic aldehydes are discussed, and the mechanism comprising the steps of single-electron oxidation of phenolate anions, and ending with retroaldol reaction of a substituted coniferyl aldehyde was pointed out as the most convincing one. The possibility and development prospects of single-stage oxidative processing of wood into the aromatic aldehydes and cellulose are analyzed.

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Section: Discussionmentioning

confidence: 99%

Section: Development Prospects For the Technology Of The Aromatic mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Catalytic Oxidation of Lignins into the Aromatic Aldehydes: General Process Trends and Development Prospects

Tarabanko

2017

IJMS

120

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“…Herein, the vanillin reacts with the octylamine forming a Schiff base which is subsequently extracted into the heptane phase. The authors demonstrated that at the optimum pH (8)(9)(10), K reaches to about 600 ( A c c e p t e d M a n u s c r i p t 15 vanillin, selectivity and yield have been improved by complexing agents (78, 79) and electrolytes (69). Attempts to overcome stripping and/or extractant recovery problems are being made resorting to aqueous two-phase systems (ATPS) and ILs.…”

Section: Introductionmentioning

confidence: 98%

Recovery of Vanillin and Syringaldehyde from Lignin Oxidation: A Review of Separation and Purification Processes

Mota

Pinto

Loureiro

et al. 2015

Separation & Purification Reviews

108

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Lignin is an underexploited side-stream of pulp and paper industry and biorefineries, being used for energy production at mill site or as low value material for dispersants or binding applications.However, an integrated process of reaction and separation can be implemented for the production of high added-value monomeric phenolic chemicals such as vanillin and syringaldehyde. In this review, the main research advances in the recovery of vanillin and syringaldehyde resulting from oxidation of lignin are addressed, covering various separation methodologies namely liquidliquid extraction, supercritical fluid extraction, distillation, crystallization, membrane separation, and adsorption.A c c e p t e d M a n u s c r i p t 2 Studies in this area started in the early years of the 20 th century, but in the last decades several processes have been suggested, mainly for vanillin separation. Finding the ultimate industrially feasible process is still a necessary task and this review points out the most promising technologies and sequence of processes.

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“…[8]. Besides this, these molecules also possessed antimicrobial activities [9,10]. The overall objective of biotransformation of these molecules was to generate analogs of these compounds with improved selectivity/toxicity profiles and better/novel pharmacokinetic potentials.…”

Section: Introductionmentioning

confidence: 98%

Atropa belladonna Hairy Roots: Orchestration of Concurrent Oxidation and Reduction Reactions for Biotransformation of Carbonyl Compounds

Srivastava

Negi

Ajayakumar

et al. 2012

Appl Biochem Biotechnol

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The biotransformation potential of a selected Atropa belladonna hairy root clone (AB-09) had been evaluated with regard to three different aromatic carbonyl compounds, i.e., 3,4,5-trimethoxybenzaldehyde (1), 3,4,5-trimethoxyacetophenone (2), and 3,4,5-trimethoxy benzoic acid (3). The results demonstrated for the first time the untapped potentials of the selected hairy root clone to perform simultaneous oxidation (34.49%) and reduction (32.68%) of 3,4,5-trimethoxy benzaldehyde (1) into 3,4,5-trimethoxy benzoic acid (3), and 3,4,5-trimethoxy benzyl alcohol (4), respectively, without any intermediate separation or addition of reagents. The same hairy root clone also demonstrated reduction (<5%) of a 3,4,5-trimethoxyacetophenone (2) into a secondary alcohol, i.e., 1-(3,4,5-trimethoxyphenyl) ethanol (5), while in the case of aromatic carboxylic acid substrate (3), no biotransformation could be obtained under the similar conditions. The current observations revealed oxidation and reduction of the formyl group of the aromatic ring, and only reduction of the carbonyl group of acetophenone through the specific hairy root clone. The concurrent oxidation and reduction reactions by the selected hairy root clone highlight the importance of this study, which, as per our observations, is the first of its kind relating the hairy root culture of A. belladonna.

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Synthetic routes to 3,4,5-trimethoxybenzaldehyde (review)

Cited by 19 publications

References 26 publications

Catalytic Oxidation of Lignins into the Aromatic Aldehydes: General Process Trends and Development Prospects

Catalytic Oxidation of Lignins into the Aromatic Aldehydes: General Process Trends and Development Prospects

Recovery of Vanillin and Syringaldehyde from Lignin Oxidation: A Review of Separation and Purification Processes

Atropa belladonna Hairy Roots: Orchestration of Concurrent Oxidation and Reduction Reactions for Biotransformation of Carbonyl Compounds

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