Carboxylic Acids, Aromatic

Röhrscheid, Freimund

doi:10.1002/14356007.a05_249

Cited by 7 publications

(8 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In most cases, aromatic amines are produced via the reduction of nitro compounds since a wide variety can be prepared economically . Similarly, carboxylic acids represent widely available and cheap starting materials and can be converted to anilines via the Schmidt reaction . For this reason, the Schmidt reaction of carboxylic acids offers a convenient alternative to nitration/reduction protocols which can result in mixtures or regioisomers.…”

Section: Temperaturementioning

confidence: 99%

The Hitchhiker’s Guide to Flow Chemistry

et al. 2017

View full text Add to dashboard Cite

Flow chemistry involves the use of channels or tubing to conduct a reaction in a continuous stream rather than in a flask. Flow equipment provides chemists with unique control over reaction parameters enhancing reactivity or in some cases enabling new reactions. This relatively young technology has received a remarkable amount of attention in the past decade with many reports on what can be done in flow. Until recently, however, the question, "Should we do this in flow?" has merely been an afterthought. This review introduces readers to the basic principles and fundamentals of flow chemistry and critically discusses recent flow chemistry accounts.

show abstract

Section: Temperaturementioning

confidence: 99%

The Hitchhiker’s Guide to Flow Chemistry

et al. 2017

View full text Add to dashboard Cite

show abstract

“…Utilizing CO 2 as a feedstock for chemical production is a major goal for the creation of a circular economy that minimizes non-renewable inputs . C–H carboxylation, the conversion of a C–H bond into a carboxylate (C–CO 2 – ) with CO 2 and a base (Scheme ), has attracted interest as a way to utilize CO 2 for the preparation of carboxylic acids and their derivatives, which comprise a large number of fine and commodity chemicals. − C–H carboxylation is conceptually appealing because it takes advantage of the oxidation state of CO 2 and avoids the limitations of other methods to synthesize carboxylic acid derivatives, such as the need to pre-install heteroatom functionality or perform harsh oxidations. − However, most C–H carboxylation methods require (super)-stoichiometric amounts of highly reactive, resource-intensive reagents to activate the C–H bond, which negates the carbon benefit of using CO 2 as a feedstock, generates large amounts of waste products, and incurs prohibitive costs for anything other than specialty chemicals. To impact sustainability, it is critical to develop alternative carboxylation methods that utilize simple reagents that can be easily regenerated.…”

Section: Introductionmentioning

confidence: 99%

Improving Carbonate-Promoted C–H Carboxylation Using Mesoporous Carbon Supports

Chant

Kanan

2023

ACS Sustainable Chem. Eng.

View full text Add to dashboard Cite

C–H carboxylation is an attractive way to utilize CO2 for chemical production provided that it does not consume resource-intensive reagents. Alkali carbonates dispersed into the pores of mesoporous supports display strongly basic reactivity under CO2, allowing them to be used as base promoters for C–H carboxylation of (hetero)arenes in the absence of other reagents or catalysts. Mesoporous oxides are convenient support materials, but only a relatively small fraction of the dispersed carbonate (ca. 10–20%) is converted to carboxylate products when metal oxide supports are used. Here, we compare mesoporous oxide and carbon supports and investigate the dependence of carbonate reactivity on the pore structure. We show that using mesoporous carbon supports can increase the carbonate conversion by 2–4× when compared to oxide supports. This improved carbonate reactivity is maintained across a variety of mesoporous carbons with different pore structures (ordered vs disordered) and pore diameters, indicating that the dispersed carbonate is intrinsically more reactive on the surface of a carbon material compared to an oxide surface. Reaction of the carboxylate products with dimethyl carbonate yields isolable methyl esters as the final product and regenerates the dispersed carbonate. We show that mesoporous carbon supports are robust to at least five cycles of successive C–H carboxylation and methylation. Understanding how the support structure affects dispersed carbonate reactivity is valuable for advancing C–H carboxylation toward practical application and utilizing these materials in other CO2 transformations.

show abstract

“…10 Trimellitic anhydride (TMA), i.e., 1,3-dioxo-1,3-dihydroisobenzofuran-5-carboxylic acid, is used, to the most part, to make plasticizers for PVC, characterized by lower volatility than phthalate ones. Polyesters and polyimides of TMA have high thermal resistance and are used in the production of wire enamels, baking varnishes, and coatings, 5 even though TMA is much more expensive compared to PA (ca. 90 vs 25 EUR for 1 kg).…”

Section: Introductionmentioning

confidence: 99%

“…As far as plasticizer production is concerned, some of the most important building blocks are maleic, phthalic, and trimellitic anhydrides. − Maleic anhydride (MA), i.e., 2,5-furandione, has a considerable industrial importance due to the presence in the molecule of the olefinic and dicarboxylic anhydride functionalities; therefore, it can be applied for both polyaddition and polycondensation. Besides plasticizers, MA is widely employed in many fields of polymer production, such as copolymers, lubricants, alkyd resins, lacquers, and, as the main application, polyester resins .…”

Section: Introductionmentioning

confidence: 99%

“…Trimellitic anhydride (TMA), i.e., 1,3-dioxo-1,3-dihydroisobenzofuran-5-carboxylic acid, is used, to the most part, to make plasticizers for PVC, characterized by lower volatility than phthalate ones. Polyesters and polyimides of TMA have high thermal resistance and are used in the production of wire enamels, baking varnishes, and coatings, even though TMA is much more expensive compared to PA (ca. 90 vs 25 EUR for 1 kg). , Thanks to its properties, TMA is widely used, and for 2020, the global market size for TMA is estimated at USD 356.5 million and is expected to reach USD 459.2 million by 2027 at a CAGR of 3.7% during the period of 2022–2027 .…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Simultaneous Determination by Selective Esterification of Trimellitic, Phthalic, and Maleic Anhydrides in the Presence of Respective Acids

et al. 2023

View full text Add to dashboard Cite

Trimellitic, phthalic, and maleic anhydrides are important building blocks to produce polymers and additives, such as plasticizers. In humans, the exposure to these compounds can cause several health issues. In European Union and USA, their presence in substances and mixtures is restricted by CLP Regulation (no. 1272/2008) and HCS/HazCom 2012, respectively, but no information about the corresponding acids is reported. For this reason, a selective method to determine anhydrides in mixtures, in the presence of acids, could be interesting. Nowadays, methods in the literature are either not selective or use explosive and toxic reagents (as diazomethane). In this work, an innovative, greener, and safer method for the simultaneous recognition and quantification of anhydrides and acids, via direct injection gas chromatography−mass spectrometry, is developed. The sample pretreatment consists in selective esterification with absolute ethanol on the anhydride, followed by a treatment with boron trifluoride-methanol for the methylation of remaining carboxylic groups. The optimization of the functionalization, a crucial step of the method, was optimized by experimental design. The limit of detection−limit of quantification (LOD−LOQ) values for trimellitic, phthalic, and maleic anhydrides are 0.31− 0.93, 0.47−1.41, and 0.06−0.18 μg/mL, respectively.

show abstract

Carboxylic Acids, Aromatic

Abstract: The article contains sections titled: 1. Introduction 2. Physical and Chemical Properties … Show more

Cited by 7 publications

References 12 publications

The Hitchhiker’s Guide to Flow Chemistry

The Hitchhiker’s Guide to Flow Chemistry

Improving Carbonate-Promoted C–H Carboxylation Using Mesoporous Carbon Supports

Simultaneous Determination by Selective Esterification of Trimellitic, Phthalic, and Maleic Anhydrides in the Presence of Respective Acids

Contact Info

Product

Resources

About