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Published in Brajendra K. Sharma, Girma Biresaw, Environmentally Friendly and Biobased Lubricants, 2016
Kenneth M. Doll, Bryan R. Moser, Zengshe Liu, Rex E. Murray
The mose commercially significant acids are succinic, lactic, itaconic, 3-hydrosypropionic and glutamic acids [117–121]. Subjection of these fermentative products to organic synthesis yields monomers such as malonic acid from 3-hydroxypropionic acid, acrylic acid from lactic and 3-hydroxypropionic acids (Figure 5.6), and methacrylic acid from itaconic acid (Figure 5.7) [122–126]. Noncarboxylic acid monomers obtained from simple sugars include 1,2-propanediol from lactic acid, 1,3-propanediol from 3-hydroxypropionic acid, 1,4-butanediol from succinic acid, and acrylonitrile from 3-hydroxypropionic acid [127–129]. Additionally, terephthalic acid can be obtained from simple sugars as well as from lignin [130].
Carboxylic Acids, Carboxylic Acid Derivatives, and Acyl Substitution Reactions
Published in Michael B. Smith, A Q&A Approach to Organic Chemistry, 2020
Malonic acid is 1,3-propanedioic acid, HO2C-CH2-CO2H. Note that since the carboxyl groups must be at each terminus, the numbers are not necessary, and this compound is simply propanedioc acid. The common name is malonic acid. Is there an intermediate for the thermal decarboxylation described in the preceding question?
Mesomorphic properties of cyanobiphenyl dimers with a substituted central malonate unit: overruling effect of fluorination
Published in Liquid Crystals, 2022
Marco André Grunwald, Alexander-Nicholas Egler-Kemmerer, Soeren Magnus Bauch, Max Ebert, Gabriele Bräuning, Anna Zens, Sabine Laschat
The synthetic route of the C2-substituted cyanobiphenyl malonates 2(Cn) and 3(Cn) is shown in Scheme 3. The synthesis started with substitution of diethyl malonate 4 using sodium hydride and either hexyl or nonafluorohexyl iodide (65 and 79%) [31], followed by saponification using aqueous sodium hydroxide providing the respective substituted malonic acid 7 and 8 (96 and 97%). The building block 9(Cn) was synthesised according to earlier works [4,32–34]. In contrast to the previously described synthetic route, the dimers 2(Cn) and 3(Cn) were produced by Fischer esterification of the C2-substituted malonic acids 7 and 8 [4]. This method was intended to save synthetic and purification steps and thus should lead to a more efficient reaction control. The target molecules 2(Cn) and 3(Cn) were then obtained by esterification of the building blocks 9(Cn) and 7 or 8 using methane sulphonic acid in 57–81% or 35–70% yield, respectively, after column chromatography. In contrast to previous work [4], a ternary solvent mixture (hexanes/CH2Cl2/EtOAc = 60: 30: 1) instead of a binary one was used for chromatographic purification, resulting in an improved separation.
Biomass-derived rctt-3,4-di-2-furanyl-1,2-cyclobutanedicarboxylic acid: a polytopic ligand for synthesizing green metal-organic materials
Published in Journal of Coordination Chemistry, 2021
Rahul K. Shahni, Houssein Amjaour, Briana Krupinsky, Sarah Reagen, Zijun D. Wang, Xu Wu, Dominic Nkemngong, Julia X. Zhao, Angel Ugrinov, Joseph Robertson, Qianli Rick Chu
In this study, we reported a polytopic ligand, rctt-3,4-di-2-furanyl-1,2-cyclobutanedicarboxylic acid (CBDA-2, Scheme 1), synthesized from two bioadvantaged chemicals (i.e., furfural and malonic acid) [13–15]. Furfural is an important renewable feedstock, which is mainly produced from hemicellulose of crop residues such as corncobs, sugarcane bagasse, and wheat bran [16, 17]. Bio-production of malonic acid involves the use of genetically modified yeast cells to ferment sugar directly into malonic acid with up to over 100% yield due to carbon dioxide sequestration during the process [18, 19]. The polytopic ligand, CBDA-2, yielded from biomass has the potential to become a useful green building block, which will make metal-organic materials more environmentally friendly. To demonstrate the potential application of this multifunctional ligand, two different two-dimensional (2D) coordination polymers have been synthesized via a conventional solution method using copper and cobalt salts, respectively. We hope that our study will initiate more work into the design, synthesis, and application of biomass-derived ligands to make coordination chemistry more sustainable.
Removal of both basic and non-basic N-compounds from diesel fuel with deep eutectic solvent
Published in Petroleum Science and Technology, 2019
As can be seen from the FTIR spectrum (b) of malonic acid in Figure 2, the broad peak appeared at 2927 cm−1 can be assigned to stretching vibrations of –CH2–. The peaks near 1700 and 1301 cm−1 came from stretching vibrations of C=O and C–O, respectively. O–H bending vibration peak appeared at 911 cm−1. From the FTIR spectrum (c) of TEAB, the peaks that appeared at 1380 and 1490 cm−1 can be assigned to C–H deformation vibrations of methyl and methylene. The peaks near 1170 and 1000 cm−1 came from stretching vibrations of C–N and C–C, respectively. Obviously, the FTIR spectrum (a) of EIL was slightly different from those of TEAB (c) and malonic acid (b). It was noteworthy that the C=O absorption peak centered at 1700 cm−1 in malonic acid shifted to a higher frequency upon treating with TEAB, meanwhile O–H bending vibration at 911 cm−1 disappeared, implying that the interaction of TEAB and malonic acid occurred, consequently, the formation of new EIL.