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Showing papers on "Carboxylic acid published in 2011"


Journal ArticleDOI
TL;DR: In this paper, the carbon dioxide sorption properties for a series of conjugated microporous polymer (CMP) networks were investigated and the carboxylic acid functionalised network, rather than its amine analogue, showed the highest isosteric heat of sorption for CO2.
Abstract: We report here the carbon dioxide sorption properties for a series of conjugated microporous polymer (CMP) networks. These CMP materials incorporate a range of chemical functionalities including carboxylic acids, amines, hydroxyl groups, and methyl groups. The carboxylic acid functionalised network, rather than its amine analogue, shows the highest isosteric heat of sorption for CO2. This supports recent computational predictions for metal–organic frameworks and suggests that acid-functionalised frameworks could outperform more widely studied amine sorbents in CO2 capture and separation application.

516 citations


Journal ArticleDOI
TL;DR: The first catalytic alkynylation of unactivated C(sp(3))-H bonds has been accomplished and can be applied to the rapid elaboration of complex aliphatic acids, for example, via azide/alkyne cycloaddition.
Abstract: The first catalytic alkynylation of unactivated C(sp3)–H bonds has been accomplished. The method allows for the straightforward introduction of an ethynyl group into aliphatic acid derivatives under palladium catalysis. This new reaction can be applied to the rapid elaboration of complex aliphatic acids, for example, via azide/alkyne cycloaddition.

323 citations


Journal ArticleDOI
TL;DR: Kinetic data for the C-H bond activation of 2-phenylpyridine by Ru(II)(carboxylate)(2)(p-cymene) I (acetate) and I' (pivalate) are available for the first time and reveal an irreversible autocatalytic process catalyzed by the coproduct HOAc or HOPiv.
Abstract: Kinetic data for the C-H bond activation of 2-phenylpyridine by Ru(II)(carboxylate)(2)(p-cymene) I (acetate) and I' (pivalate) are available for the first time. They reveal an irreversible autocatalytic process catalyzed by the coproduct HOAc or HOPiv (acetonitrile, 27 °C). The overall reaction is indeed accelerated by the carboxylic acid coproduct and water. It is retarded by a base, in agreement with an autocatalytic process induced by HOAc or HOPiv that favors the dissociation of one carboxylate ligand from I and I' and consequently the ensuing complexation of 2-phenylpyridine (2-PhPy). The C-H bond activation initially delivers Ru(O(2)CR)(o-C(6)H(4)-Py)(p-cymene) A or A', containing one carboxylate ligand (OAc or OPiv, respectively). The overall reaction is accelerated by added acetates. Consequently, C-H bond activation (faster for acetate I than for pivalate I') proceeds via an intermolecular deprotonation of the C-H bond of the ligated 2-PhPy by the acetate or pivalate anion released from I or I', respectively. The 18e complexes A and A' easily dissociate, by displacement of the carboxylate by the solvent (also favored by the carboxylic acid), to give the same cationic complex B(+) {[Ru(o-C(6)H(4)-Py)(p-cymene)(MeCN)](+)}. Complex B(+) is reactive toward oxidative addition of phenyl iodide, leading to the diphenylated 2-pyridylbenzene.

313 citations


Journal ArticleDOI
TL;DR: In this paper, a post-functionalization method for metal-organic frameworks (MOFs) was developed to introduce acidity for catalysis, resulting in a Bronsted sulfoxy acid group attached to up to 50% of the aromatic terephthalate linkers of the structure.

266 citations


Journal ArticleDOI
TL;DR: Low current densities and Fe(2+) contents are preferable to remove more efficiently these acids by the most potent AO-BDD-Fe(2+)-UVA method.

249 citations


Journal ArticleDOI
TL;DR: In this article, a series of carboxyl-group-functionalized imidazolium-based ionic liquids (CILs) were synthesized and grafted onto silica gel.

237 citations


Journal ArticleDOI
TL;DR: A cobalt(II) hangman porphyrin with a xanthene backbone and a carboxylic acid hanging group catalyzes the electrochemical production of hydrogen from benzoic and tosic acid in acetonitrile solutions and is shown to be exclusively involved in the generation of H(2) from weak acids.
Abstract: A cobalt(II) hangman porphyrin with a xanthene backbone and a carboxylic acid hanging group catalyzes the electrochemical production of hydrogen from benzoic and tosic acid in acetonitrile solutions. We show that CoIIH is exclusively involved in the generation of H2 from weak acids. In a stronger acid, a CoIIIH species is observed electrochemically, but it still needs to be further reduced to CoIIH before H2 generation occurs. Overpotentials for H2 generation are lowered as a result of the hangman effect.

235 citations


Journal ArticleDOI
TL;DR: In this paper, solid Bronsted catalysts such as Cs2HPW12O40 and HY zeolite have been used to accelerate cellulose depolymerization.
Abstract: Crystalline cellulose treated in hydrothermal conditions (190 °C, 24 h) is partially solubilised, 30%, into water soluble oligosaccharides/polymers with the formation of small amounts of glucose and 5-HMF. In the presence of solid Bronsted catalysts such as Cs2HPW12O40 and HY zeolite, the extent of the cellulose depolymerisation was not changed when no leaching occurred. However, a quite different products distribution was obtained, in favour of further transformations of glucose and HMF in levulinic and formic acids. On the opposite, solid Lewis acids such as tungstated zirconia (ZrW) and tungstated alumina (AlW) exhibited a remarkable promoting effect on the cellulose depolymerisation which was raised up to 45% while an unexpected decrease of the proportion of water soluble oligosaccharides/polymers was observed. Yields of 27 mol% and 18.5 mol% in lactic acid were achieved on AlW and ZrW, respectively. Moreover, these tungsten based Lewis acids exhibited a good stability and recyclability. The efficiency of the solid Lewis acids ZrW and AlW to produce lactic acid directly from crystalline cellulose was explained by a positive synergy between water autoprotolysis responsible of the cellulose depolymerisation into soluble intermediates which are further converted on the solid Lewis catalyst surface.

233 citations


Journal ArticleDOI
TL;DR: In this paper, a model study of the radical addition of 2-mercaptoethanol onto oleic acid was performed under mild conditions (generation of radicals under UV light at room temperature without any photoinitiator).
Abstract: A model study of the radical addition of 2-mercaptoethanol onto oleic acid was performed under mild conditions (generation of radicals under UV light at room temperature without any photoinitiator). To evaluate the efficiency and the robustness of thiol−ene reaction, experimental parameters were varied, such as the irradiation intensity (ranging from 0.5 to 15.0 W/cm2), the thiol/double bond ratio (ranging from 1.2/1 to 5.0/1), the solvent/double bond ratio (ranging from 0/1 to 500/1), and the number of double bonds per chain. It was especially shown that the higher the content of polyunsaturated fatty chains, the lower the rate of 2-mercaptoethanol grafting. Best yields were reached in 1 h reaction for a thiol/ene ratio of 3/1, without solvent, using maximum UV intensity. Side reactions, identified by NMR, FT-IR, LC-MS, and iodine titration, were upon esterification between the carboxylic acid function of oleic acid and the hydroxyl function of 2-mercaptoethanol, disulfide formation, double-bond isomeriz...

211 citations


Journal ArticleDOI
TL;DR: A mechanistic study on the homogeneously ruthenium/phosphine catalyzed transformations of levulinic acid and itaconic acid to the corresponding lactones, diols, and cyclic ethers, forming a rational basis for further catalyst development.
Abstract: Selective hydrogenation of biogenic carboxylic acids is an important transformation for biorefinery concepts based on platform chemicals. We herein report a mechanistic study on the homogeneously ruthenium/phosphine catalyzed transformations of levulinic acid (LA) and itaconic acid (IA) to the corresponding lactones, diols, and cyclic ethers. A density functional theory (DFT) study was performed and corroborated with experimental data from catalytic processes and NMR investigations. For [Ru(TriPhos)H](+) as the catalytically active unit, a common mechanistic pathway for the reduction of the C═O functionality in aldehydes, ketones, lactones, and even free carboxylic acids could be identified. Hydride transfer from the Ru-H group to the carbonyl or carboxyl carbon is followed by protonation of the resulting Ru-O unit via σ-bond metathesis from a coordinated dihydrogen molecule. The energetic spans for the reduction of the different functional groups increase in the order aldehyde < ketone < lactone ≈ carboxylic acid. This reactivity pattern as well as the absolute values are in full agreement with experimentally observed activities and selectivities, forming a rational basis for further catalyst development.

208 citations


Journal ArticleDOI
TL;DR: Under the rhodium catalysis, the cine-olefination of heteroarene carboxylic acids such as thiophene-2-car boxylic acid proceeds smoothly accompanied by decarboxylation to selectively produce the corresponding vinylheteroarenes derivatives.
Abstract: The ortho-olefination of benzoic acids can be achieved effectively through rhodium-catalyzed oxidative coupling with alkenes. The carboxylic group is readily removable to allow ortho-olefination/decarboxylation in one pot. α,β-Unsaturated carboxylic acids such as methacrylic acid also undergo the olefination at the β-position. Under the rhodium catalysis, the cine-olefination of heteroarene carboxylic acids such as thiophene-2-carboxylic acid proceeds smoothly accompanied by decarboxylation to selectively produce the corresponding vinylheteroarene derivatives.

Journal ArticleDOI
TL;DR: This finding clarifies the long proposed reaction mechanism that operates via the generation of an alkenylpalladium intermediate and subsequent transformation of this complex in a variety of reactions catalyzed by a combination of Brϕnsted acid and Pd(0) complex.
Abstract: A facile, highly stereo- and regioselective hydrometalation of alkynes generating alkenylmetal complex is disclosed for the first time from a reaction of alkyne, carboxylic acid, and a zerovalent group 10 transition metal complex M(PEt3)4 (M = Ni, Pd, Pt). A mechanistic study showed that the hydrometalation does not proceed via the reaction of alkyne with a hydridometal generated by the protonation of a carboxylic acid with Pt(PEt3)4, but proceeds via a reaction of an alkyne coordinate metal complex with the acid. This finding clarifies the long proposed reaction mechanism that operates via the generation of an alkenylpalladium intermediate and subsequent transformation of this complex in a variety of reactions catalyzed by a combination of Brϕnsted acid and Pd(0) complex. This finding also leads to the disclosure of an unprecedented reduction of alkynes with formic acid that can selectively produce cis-, trans-alkenes and alkanes by slightly tuning the conditions.

Journal ArticleDOI
TL;DR: In this paper, the copolymerization of cyclohexene oxide (CHO) with alicyclic anhydrides applying chromium tetraphenylprophyrinato (TPPCrCl, 1) and salophen (SalophenCrCl, 2) catalysts resulted in polyesters or polyester-co-ethers, depending on the nature of the catalyst, presence of a cocatalyst, solvent and type of anhydride.
Abstract: Copolymerization of cyclohexene oxide (CHO) with alicyclic anhydrides applying chromium tetraphenylprophyrinato (TPPCrCl, 1) and salophen (SalophenCrCl, 2) catalysts resulted in polyesters or poly(ester-co-ether)s, depending on the nature of the catalyst, presence of a cocatalyst, solvent and type of anhydride. The combination of 1 as catalyst and 4-N,N-dimethylamino-pyridine (DMAP) as cocatalyst in the copolymerization of CHO with succinic anhydride (SA), cyclopropane-1,2-dicarboxylic acid anhydride (CPrA), cyclopentane-1,2-dicarboxylic acid anhydride (CPA) or phthalic anhydride (PA) invariably resulted in a completely alternating topology and therefore a pure polyester. Contrarily, 2 in combination with DMAP did not afford pure polyesters for the copolymerization of CHO with SA or CPrA but did render the alternating topology when CPA or PA was used as anhydride comonomer. Water proved to be an efficient bifunctional CTA affording α,ω-hydroxyl-terminated polyesters without loss of catalytic activity. Whe...

Journal ArticleDOI
01 Nov 2011-Fuel
TL;DR: In this paper, a model feed consisting of oleic acid and tripalmitin in molar ratio 1:3 was hydrotreated at 325°C with 20 bars H2 in a stirred batch autoclave with a 5% Pt/γ-Al2O3 catalyst, and samples were extracted periodically and analyzed on GC.

Journal ArticleDOI
Cuiying Hao1, Shengping Wang1, Maoshuai Li1, Liqiong Kang1, Xinbin Ma1 
TL;DR: In this article, the authors reported on the preparation and application of novel heterogeneous supported ruthenium catalysts, which are active in the synthesis of formic acid from the hydrogenation of carbon dioxide.

Journal ArticleDOI
TL;DR: Ruthenium nanoparticles supported on titania are over three times more active than conventional ruthenia on carbon for the hydrogenation of lactic acid.

Journal ArticleDOI
TL;DR: It is demonstrated that their corresponding hemiacetals are the kinetically important intermediates in both their acylation and annulation reactions, and strongly suggested that generation of substantial amounts of the a,b-unsaturated acyl azolium intermediate should be possible in the absence of a nucleophile.
Abstract: Catalytically generated acyl azoliums I and their α,β-unsaturated counterparts II are thought to be key reactive intermediates in a rapidly growing number of transformations promoted by N-heterocyclic carbene (NHC) catalysts.[1] Acyl azoliums are invoked in the postulated catalytic cycles of nearly all of the new NHC-catalyzed reactions of α-functionalized aldehydes reported since 2004, in which they are generally assumed to possess the reactivity of an activated carboxylic acid, that is, analogous to an activated ester.[2] In NHC-catalyzed processes, they are most often obtained through internal redox reactions of functionalized aldehydes but have also been prepared by oxidations of the Breslow intermediates[3] or additions to ketenes.[4] Acyl azoliums I are important intermediates in thiamine pyrophosphate (ThPP) dependent enzymatic reactions.[5] Townsend et al. have recently proposed that unsaturated acyl azolium III is the key intermediate in clavulanic acid biosynthesis;[6] despite careful efforts, III or its analogues II have never been characterized or independently synthesized. Here, we document the observation and characterization of α,β-unsaturated acyl azoliums 1 and 2 (Scheme 1) and demonstrate that their corresponding hemiacetals (1′ and 2”) are the kinetically important intermediates in both their acylation and annulation reactions. Open in a separate window Scheme 1 Various acyl azoliums and the hemiacetals.

Journal ArticleDOI
TL;DR: In this article, the effect of support on the reaction routes may be attributed to these factors of catalysts, i.e., surface acidity, metal-support interaction and electronic state of Ru species.
Abstract: For the aqueous-phase hydrodeoxygenation (APHDO) of carboxylic acids over the Ru/C, Ru/ZrO2 and Ru/Al2O3 catalysts, the C O hydrogenation and C–C bond cleavage reactions were studied by collecting reaction kinetics data and the measures of DRIFTS. The C–C bond cleavage was improved at high temperature and with high metal loadings. The acidic supports in combination with Ru metal can favor the C O hydrogenation of carboxyl. The C–C bond cleavage derived from the decarbonylation of acyl on the catalyst was studied by the measures of DRIFTS. The APHDO and DRIFTS results demonstrated that the C–C bond cleavage was favored in the order of Ru/C > Ru/ZrO2 > Ru/Al2O3. The catalysts were characterized by multiple methods (H2-TPR, NH3-TPD, CO-FTIR and DRIFTS of propanoic acid). It is concluded that the effect of support on the reaction routes may be attributed to these factors of catalysts, i.e., surface acidity, metal–support interaction and electronic state of Ru species.

Journal ArticleDOI
TL;DR: An efficient arylation of carboxylic acids with diaryliodonium salts has been developed, giving aryl esters in high yields within short reaction times for both aromatic and aliphatic substrates.

Journal ArticleDOI
TL;DR: In this paper, ten new co-crystals of an antibacterial drug sulfamethazine (SFZ) with various carboxylic acid and amide co-formers have been synthesized.
Abstract: Ten new co-crystals of an antibacterial drug sulfamethazine (SFZ) with various carboxylic acid and amide co-formers have been synthesized. These new forms are characterized by single crystal X-ray diffraction, infrared spectroscopy, differential scanning calorimetry (DSC), and thermogravimetric analysis (TGA). Crystal structures with 4-hydroxybenzoic acid (HBA), 2,4-dihydroxybenzoic acid (DHB), 3,4-dichlorobenzoic acid (DCB), sorbic acid (SOR), fumaric acid (FUM), 1-hydroxy-2-naphthoic acid (1HNA), benzamide (BEN), picolinamide (PIC), 4-hydroxybenzamide (HBEN), and 3-hydroxy-2-naphthoic acid (3HNA) are determined. The SFZ molecule displays co-former assisted amidine to imidine tautomerism in the co-crystals in that the sulfonamide NH proton moves to one of the pyrimidine N atoms. In all the cases, the SFZ forms a robust hydrogen bonded synthon with a carboxylic acid (amidine(SFZ)···acid/imidine(SFZ)···acid) or amide (imidine(SFZ)···amide) group from the co-former. The SFZ molecule, in all the carboxylic a...

Journal ArticleDOI
TL;DR: In this paper, a negative-ion electrospray ionization (ESI) Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS) was used for selective ionization of acidic components of crude oils and naphthenates.

Journal ArticleDOI
14 Mar 2011-Langmuir
TL;DR: It has been found that side chain functionalization of Fmoc-Phe exerts a significant effect on the self-assembly and hydrogelation behavior of these molecules; fluorinated derivatives, including pentafluorophenylalanine and 3-F-phenylalanines, spontaneously self-assemble into fibrils that form a hydrogels network upon dissolution into water.
Abstract: The development of hydrogels resulting from the self-assembly of low molecular weight (LMW) hydrogelators is a rapidly expanding area of study. Fluorenylmethoxycarbonyl (Fmoc) protected aromatic amino acids derived from phenylalanine (Phe) have been shown to be highly effective LMW hydrogelators. It has been found that side chain functionalization of Fmoc-Phe exerts a significant effect on the self-assembly and hydrogelation behavior of these molecules; fluorinated derivatives, including pentafluorophenylalanine (F5-Phe) and 3-F-phenylalanine (3-F-Phe), spontaneously self-assemble into fibrils that form a hydrogel network upon dissolution into water. In this study, Fmoc-F5-Phe-OH and Fmoc-3-F-Phe-OH were used to characterize the role of the C-terminal carboxylic acid on the self-assembly and hydrogelation of these derivatives. The C-terminal carboxylic acid moieties of Fmoc-F5-Phe-OH and Fmoc-3-F-Phe-OH were converted to C-terminal amide and methyl ester groups in order to perturb the hydrophobicity and h...

Journal ArticleDOI
01 Nov 2011-Carbon
TL;DR: In this article, the surface of carbon fibers is functionalized by a reaction of naturally existing surface hydroxyl groups with isopropylidene malonate to graft terminal malonic esters, effectively creating a carboxyl functionalized surface.

Journal ArticleDOI
Huaiqing Zhao1, Ye Wei1, Jing Xu1, Jian Kan1, Weiping Su1, Maochun Hong1 
TL;DR: By using Pd(TFA)(2)/PCy(3) as a catalyst, a broad range of aromatic carboxylic acids efficiently underwent decarboxylative coupling with an array of polyfluoroarenes in the presence of stoichiometric amount of silver salts to generate biaryls.
Abstract: By using Pd(TFA)2/PCy3 as a catalyst, a broad range of aromatic carboxylic acids, including heteroaromatic carboxylic acids, efficiently underwent decarboxylative coupling with an array of polyfluoroarenes in the presence of stoichiometric amount of silver salts to generate biaryls. Silver salts were adjusted to the reactivity of aromatic carboxylic acids to efficiently suppress the protodecarboxylation and therefore improve decarboxylative cross-couplings. It was established that the palladium complex containing the PCy3 ligand was capable of catalyzing the decarboxylation of electron-rich aromatic carboxylic acids, and silver salts promoted the decarboxylation of both electron-rich and -deficient ones. To explain the two different decarboxylation processes, two possible reaction pathways are proposed, which were further supported by the facts that the stoichiometric arylpalladium complex can directly arylate pentafluorobenzene in the presence of PCy3 and the arylpalladium complex can catalyze the decarb...

Journal ArticleDOI
TL;DR: In this article, the synthesis of esters from trimethylolpropane (TMP) and carboxylic acids from C5 to C18 has been studied and compared using different heterogeneous catalysts (silica-sulphuric acid, Amberlyst-15, and immobilised lipase B from Candida antarctica ).
Abstract: Biolubricants derived from vegetable oils are environmentally compatible products due to their low toxicity and good biodegradability. Synthetic esters based on polyols and fatty acids possess suitable properties for lubricant applications, even at extreme temperatures. In this work, synthesis of esters from trimethylolpropane (TMP) and carboxylic acids from C5 to C18 has been studied and compared using different heterogeneous catalysts (silica–sulphuric acid, Amberlyst-15, and immobilised lipase B from Candida antarctica ). Silica–sulphuric acid was found to be the most efficient catalyst followed by Amberlyst-15, especially when using short chain carboxylic acids. The reaction efficiency decreased with increasing alkyl chain length. On the other hand, the immobilised lipase (Novozym ® 435) did not exhibit any activity with C5 acid and the activity increased with increase in length of the fatty acid chain. For synthesis of C18-ester, the biocatalytic production turned out to be comparable to silica–sulphuric acid, and moreover led to a better quality of the final product. The products showed suitable cold-flow properties for application at low temperature. A general trend of increasing pour point (−75 °C to −42 °C) and viscosity index (80–208) with increase in alkyl chain of the carboxylic acid from C5 to C18 was observed. The synthesis of TMP-trioleate using the solid acid catalysts and the biocatalyst was compared using the freeware package EATOS (environmental assessment tool for organic synthesis) and showed the enzymatic route to have the least environmental impact.

Journal ArticleDOI
TL;DR: The theoretical aspects of the present article have led to propose the most efficient pathway leading to carboxylic acid functional groups on the surface, which ends up with the synergistic formation of dangling -COOH groups and the enlargement of the vacancies.
Abstract: The nitric acid oxidation of multiwalled carbon nanotubes leading to surface carboxylic groups has been investigated both experimentally and theoretically. The experimental results show that such a reaction involves the initial rapid formation of carbonyl groups, which are then transformed into phenol or carboxylic groups. At room temperature, this reaction takes place on the most reactive carbon atoms. At higher temperatures a different mechanism would operate, as evidenced by the difference in activation energies. Experimental data can be partially related to first-principles calculations, showing a multistep functionalization mechanism. The theoretical aspects of the present article have led us to propose the most efficient pathway leading to carboxylic acid functional groups on the surface. Starting from mono-vacancies, it ends up with the synergistic formation of dangling -COOH groups and the enlargement of the vacancies.

Journal ArticleDOI
TL;DR: Carboxylic acid esters can be prepared in excellent yields at room temperature from an acid and either a phenol or an aliphatic alcohol using the peptide coupling reagents, TBTU, TATU, or COMU, in the presence of organic bases.

Journal ArticleDOI
08 Aug 2011-Analyst
TL;DR: The functional groups of CNTs therefore modulate the electrochemical properties, and the increase in sensitivity from CNT modification facilitates measurements in biological samples.
Abstract: The surface properties of carbon-based electrodes are critically important for the detection of biomolecules and can modulate electrostatic interactions, adsorption and electrocatalysis. Carbon nanotube (CNT) modified electrodes have previously been shown to have increased oxidative sensitivity and reduced overpotential for catecholamine neurotransmitters, but the effect of surface functionalities on these properties has not been characterized. In this study, we modified carbon-fiber microelectrodes (CFMEs) with three differently functionalized single-wall carbon nanotubes and measured their response to serotonin, dopamine, and ascorbic acid using fast-scan cyclic voltammetry. Both carboxylic acid functionalized and amide functionalized CNTs increased the oxidative current of CFMEs by approximately 2–6 fold for the cationic neurotransmitters serotonin and dopamine, but octadecylamine functionalized CNTs resulted in no significant signal change. Similarly, electron transfer was faster for both amide and carboxylic acid functionalized CNT modified electrodes but slower for octadecylamine CNT modified electrodes. Oxidation of ascorbic acid was only increased with carboxylic acid functionalized CNTs although all CNT-modified electrodes showed a trend towards increased reversibility for ascorbic acid. Carboxylic acid-CNT modified disk electrodes were then tested for detection of serotonin in the ventral nerve cord of a Drosophila melanogaster larva, and the increase in sensitivity was maintained in biological tissue. The functional groups of CNTs therefore modulate the electrochemical properties, and the increase in sensitivity from CNT modification facilitates measurements in biological samples.

Journal ArticleDOI
TL;DR: Using air as oxidant and a balloon pressure of CO, indoles, thiophenes and benzothiophenses are converted in the presence of different alcohols into carboxylic acid esters as discussed by the authors.
Abstract: Using air as oxidant and a balloon pressure of CO, indoles, thiophenes and benzothiophenes are converted in the presence of different alcohols into carboxylic acid esters.

Journal ArticleDOI
Kyoohee Woo1, Youngwoo Kim1, Byungyoon Lee, Jong-Hee Kim, Jooho Moon1 
TL;DR: The oxalic acid more effectively reduces copper oxide than formic acid and its usage can shorten the annealing time for highly conductive printed copper film, allowing fabrication of copper patterns with low resistivity comparable to the resistivity of bulk copper.
Abstract: The reduction effect of various carboxylic acids on inkjet-printed copper film was investigated. Carboxylic acids were exposed to the film by nitrogen gas that was bubbled through the liquid acids during the annealing process. It was observed that in the case of saturated monocarboxylic acid (formic, acetic, propionic, butyric), the acids with shorter hydrocarbon chains perform better in reducing the surface copper oxides in the printed copper conductive film. The printed films exposed to formic acid vapor exhibited the lowest resistivity (3.10 and 2.30 μΩ cm when annealed at 200 and 250 °C, respectively). In addition, the oxalic acid more effectively reduces copper oxide than formic acid and its usage can shorten the annealing time for highly conductive printed copper film. This reductive annealing process allows fabrication of copper patterns with low resistivity, (3.82 μΩ cm annealed at 250 °C) comparable to the resistivity of bulk copper.