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1

Tothadi, Srinu, et Amala Phadkule. « Does stoichiometry matter ? Cocrystals of aliphatic dicarboxylic acids with isonicotinamide : odd–even alternation in melting points ». CrystEngComm 21, no 15 (2019) : 2481–84. http://dx.doi.org/10.1039/c9ce00299e.

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This study outlines the synthesis of four cocrystals of aliphatic dicarboxylic acids {pimelic acid to sebacic acid (HOOC–(CH2)n–COOH, n = 5, 6, 7 and 8)} and isonicotinamide in a ratio of 1 : 2.
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2

Dou, Qiang. « Effect of Calcium Salts of Aliphatic Dicarboxylic Acids on the Formation of β Crystalline Form in Isotactic Poly(Propylene) ». Advanced Materials Research 391-392 (décembre 2011) : 875–82. http://dx.doi.org/10.4028/www.scientific.net/amr.391-392.875.

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The effects of calcium salts of aliphatic dicarboxylic acids on the polymorphism of iPP have been investigated by means of WAXD, DSC and PLM. It is found that β crystalline form content and nucleation ability of the nucleated iPP are dependent on the carboatomic numbers of the acids. Calcium salts of malonic acid, glutaric acid, pimelic acid and suberic acid are good β nucleators. Calcium salts of succinic acid and adipic acid are α nucleators. Calcium salts of acids with carboatomic numbers of 5 to 8 are good nucleators. The β spherulite size is the smallest in iPP doped with calcium pimelate.
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Ahmed, Barham Sharif, Luqman Omar Hamasalih, Kosar Hikmat Hama Aziz, Yousif M. Salih, Fryad S. Mustafa et Khalid Mohammad Omer. « Efficient Oxidative Desulfurization of High-Sulfur Diesel via Peroxide Oxidation Using Citric, Pimelic, and α-Ketoglutaric Acids ». Separations 10, no 3 (15 mars 2023) : 206. http://dx.doi.org/10.3390/separations10030206.

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The widespread use of diesel fuel for transportation, industry, and electricity generation causes several environmental issues via an increase in the amount of sulfur compound emissions. Commercial diesel fuel must be free of sulfur-containing compounds since they can cause several environmental problems. Considering the currently available processes to eliminate sulfur compounds, oxidative desulfurization (ODS) is one of the effective means for this purpose. This work presented a simple, low cost, and efficient ODS system of high-sulfur diesel fuels using peroxide oxidation with the aid of citric, pimelic, and α-ketoglutaric acids. The aim of the study was to investigate the potential of these acids as hydrogen peroxide (H2O2) activators for ODS and to optimize the reaction conditions for maximum sulfur removal. The results showed that citric, pimelic, and α-ketoglutaric acids were effective catalysts for the desulfurization of high-sulfur diesel with an initial sulfur content of 2568 mg L−1, achieving a sulfur removal efficiency of up to 95%. The optimized reaction conditions were found to be 0.6 g of carboxylic acid dosage and 10 mL of H2O2 at 95 °C. The desulfurization efficiency of the real diesel sample (2568 mg L−1) was shown to be 27, 34, and 84.57%, using citric acid, α-ketoglutaric acid, and pimelic acid after 1h, respectively. The effectiveness of the oxidation process was characterized by gas chromatographic pulsed flame photometric detector (GC-PFPD) and Fourier-transform infrared spectroscopy (FTIR) techniques. The experimental results demonstrated that the developed system exhibited high efficiency for desulfurization of real high-sulfur diesel fuels that could be a good alternative for commercial application with a promising desulfurization efficiency.
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Burger, Artur, Jan-Olav Henck et Maria N. D�nser. « On the polymorphism of dicarboxylic acids : I pimelic acid ». Mikrochimica Acta 122, no 3-4 (septembre 1996) : 247–57. http://dx.doi.org/10.1007/bf01245785.

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5

Schaefer, Thomas, Liang Wen, Arne Estelmann, Joely Maak et Hartmut Herrmann. « pH- and Temperature-Dependent Kinetics of the Oxidation Reactions of OH with Succinic and Pimelic Acid in Aqueous Solution ». Atmosphere 11, no 4 (26 mars 2020) : 320. http://dx.doi.org/10.3390/atmos11040320.

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Rate constants for the aqueous-phase reactions of the hydroxyl radical with the dicarboxylic acids, succinic acid and pimelic acid were determined using the relative rate technique over the temperature range 287 K ≤ T ≤ 318 K and at pH = 2.0, 4.6 or 4.9 and 8.0. OH radicals were generated by H2O2 laser flash photolysis while thiocyanate was used as a competitor. The pH values were adjusted to obtain the different speciation of the dicarboxylic acids. The following Arrhenius expressions were determined (in units of L mol−1 s−1): succinic acid, k(T, AH2) (2.1 ± 0.1) × 1010 exp[(−1530 ± 250 K)/T], k(T, AH−) (1.8 ± 0.1) × 1010 exp[(−1070 ± 370 K)/T], k(T, A2−) (2.9 ± 0.2) × 1011 exp[(−1830 ± 350 K)/T] and pimelic acid, k(T, AH2) (7.3 ± 0.2) × 1010 exp[(−1040 ± 140 K)/T], k(T, AH−) (1.8 ± 0.1) × 1011 exp[(−1200 ± 240 K)/T], k(T, A2−) (1.4 ± 0.1) × 1012 exp[(−1830 ± 110 K)/T]. A general OH radical reactivity trend for dicarboxylic acids was found as k(AH2) < k(AH−) < k(A2−). By using the pH and temperature dependent rate constants, source and sinking processes in the tropospheric aqueous phase can be described precisely.
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6

López-Sánchez, Aroa, Belén Floriano, Eloisa Andújar, Maria José Hernáez et Eduardo Santero. « Tetralin-Induced and ThnR-Regulated Aldehyde Dehydrogenase and β-Oxidation Genes in Sphingomonas macrogolitabida Strain TFA ». Applied and Environmental Microbiology 76, no 1 (6 novembre 2009) : 110–18. http://dx.doi.org/10.1128/aem.01846-09.

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ABSTRACT A new cluster of genes has been found downstream of the previously identified thnA2 gene. The gene products are similar to nonacylating aldehyde dehydrogenases (ThnG) and to proteins representing a complete β-oxidation pathway (ThnH to ThnP). ThnG has a nonacylating NAD-dependent pimelic semialdehyde dehydrogenase activity that renders pimelic acid a seven-carbon dicarboxylic acid. For further metabolism via β-oxidation, pimelic acid could be acylated by a constitutive acyl coenzyme A (acyl-CoA) ligase found in Sphingomonas macrogolitabida strain TFA or by ThnH, which would transfer CoA from a previously acylated molecule. The first round of β-oxidation is expected to render glutaryl-CoA and acetyl-CoA. Glutaryl-CoA dehydrogenase (ThnN) would catalyze the oxidation and decarboxylation of glutaryl-CoA and yield crotonyl-CoA, which enters the central metabolism via acetyl-CoA. Mutagenesis studies have shown that these genes are not essential for growth on tetralin or fatty acids, although a thnG disruption mutant showed threefold less pimelic semialdehyde dehydrogenase activity. Transcriptional analysis indicated that these genes are induced by tetralin, subjected to catabolite repression, and regulated by the same regulatory factors previously identified to regulate other thn structural genes. In the present study, transcription initiation upstream of thnH and thnM has been detected by primer extension analysis, and putative promoters were identified by sequence analysis. In addition, binding of the activator ThnR to its putative binding sites at the PH and PM promoter regions has been characterized. These results provide a complete characterization of the biodegradation pathway of tetralin to central metabolites and describe the transcriptional organization of the thn operons in S. macrogolitabida strain TFA.
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Xu, Wei, Wen-xiang Huang et Hong-yan Chen. « Pimelic acid–urea (1/2) ». Acta Crystallographica Section E Structure Reports Online 67, no 7 (25 juin 2011) : o1795. http://dx.doi.org/10.1107/s1600536811023439.

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8

Li, Hua, Juan Liu, Jiang Zhu, Lei Zhao et Yadong Zhang. « Solubility of pimelic acid in water ». Russian Journal of Physical Chemistry A 85, no 8 (8 juillet 2011) : 1472–74. http://dx.doi.org/10.1134/s0036024411080139.

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9

Roy, Siddhartha, Desh Deepak Singh et M. Vijayan. « X-ray studies on crystalline complexes involving amino acids and peptides. XLII. Adipic acid complexes of L- and DL-arginine and supramolecular association in arginine–dicarboxylic acid complexes ». Acta Crystallographica Section B Structural Science 61, no 1 (19 janvier 2005) : 89–95. http://dx.doi.org/10.1107/s0108768104030010.

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The adipic acid complexes of DL-arginine and L-arginine are made up of zwitterionic, singularly positively charged arginium ions and doubly negatively charged adipate ions, with a 2:1 stoichiometry. One of the two crystallographically independent arginium ions in the L-arginine complex has a conformation hitherto unobserved in crystal structures containing the amino acid. In the present study the structural data on arginine complexes of saturated dicarboxylic acids with 0–5 C atoms separating the two carboxyl functions are given. In terms of molecular aggregation, formic and acetic acid complexes behave in a similar way to those involving fairly long carboxylic acids such as adipic acid. By and large, the supramolecular assembly in complexes involving dicarboxylic acids with 3 or more C atoms separating the carboxyl groups (glutaric, adipic and pimelic acids), and those involving formic and acetic acids, have common features. The aggregation patterns in complexes involving oxalic, malonic and maleic acids do not share striking features among themselves (except for the mode of hydrogen-bonded dimerization of arginium ions) or with those involving larger dicarboxylic acids. Complexes of succinic acid, the shortest linear dicarboxylic acid, share features with those involving shorter as well as longer dicarboxylic acids. The difference in the behaviour of long and short dicarboxylic acids and the ambiguous behaviour of succinic acid can be broadly related to their lengths.
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10

Broda, Jan, Marcin Baczek, Janusz Fabia, Dorota Binias et Ryszard Fryczkowski. « Nucleating agents based on graphene and graphene oxide for crystallization of the β-form of isotactic polypropylene ». Journal of Materials Science 55, no 4 (26 septembre 2019) : 1436–50. http://dx.doi.org/10.1007/s10853-019-04045-y.

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Abstract During the investigations, functionalization of graphene oxide synthesized using modified Hummers’ method and its reduced form was performed. Mixtures of graphene oxide and reduced graphene oxide with pimelic acid and calcium hydroxide were prepared for functionalization. During the reaction, the molecules of pimelic acid were attached to the surface of graphene sheets. By forming links between the carboxylic groups of pimelic acid and graphene oxide, the durable connection was achieved. The functionalized graphene oxide and the reduced graphene oxide were used as additives in isotactic polypropylene crystallization. The influence of additives on crystallisation in non-isothermal conditions was examined using polarized optical microscopy and differential scanning calorimetry. The effect of the additives on the polypropylene structure was analysed using wide-angle X-ray scattering. For both functionalized compounds, the nucleating ability towards β-form of polypropylene was detected. Both additives showed the increase in the nucleation rate and promotion of growth of the β-form crystals. Nucleation efficiency similar to other nucleating agents used in the crystallization of the β-form of polypropylene was revealed.
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11

BINIEDA, Andrew, Martin FUHRMANN, Bruno LEHNER, Claudine REY-BERTHOD, Séverine FRUTIGER-HUGHES, Graham HUGHES et Nicholas M. SHAW. « Purification, characterization, DNA sequence and cloning of a pimeloyl-CoA synthetase from Pseudomonas mendocina 35 ». Biochemical Journal 340, no 3 (8 juin 1999) : 793–801. http://dx.doi.org/10.1042/bj3400793.

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A pimeloyl-CoA synthetase from Pseudomonas mendocina 35 was purified and characterized, the DNA sequence determined, and the gene cloned into Escherichia coli to yield an active enzyme. The purified enzyme had a pH optimum of ≈ 8.0, Km values of 0.49 mM for pimelic acid, 0.18 mM for CoA and 0.72 mM for ATP, a subunit Mr of ≈ 80000 as determined by SDS/PAGE, and was found to be a tetramer by gel-filtration chromatography. The specific activity of the purified enzyme was 77.3 units/mg of protein. The enzyme was not absolutely specific for pimelic acid. The relative activity for adipic acid (C6) was 72% and for azaleic acid (C9) was 18% of that for pimelic acid (C7). The N-terminal amino acid was blocked to amino acid sequencing, but controlled proteolysis resulted in three peptide fragments for which amino acid sequences were obtained. An oligonucleotide gene probe corresponding to one of the amino acid sequences was synthesized and used to isolate the gene (pauA, imelic cid-tilizing ) coding for pimeloyl-CoA synthetase. The pauA gene, which codes for a protein with a theoretical Mr of 74643, was then sequenced. The deduced amino acid sequence of the enzyme showed similarity to hypothetical proteins from Archaeoglobus fulgidus, Methanococcus jannaschii, Pyrococcus horikoshii, E. coli and Streptomyces coelicolor, and some limited similarity to microbial succinyl-CoA synthetases. The similarity with the protein from A. fulgidus was especially strong, thus indicating a function for this unidentified protein. The pauA gene was cloned into E. coli, where it was expressed and resulted in an active enzyme.
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12

Yang, Peng, Ian Rosbottom, Zhonghua Li, Vivek Verma, Songgu Wu, Junbo Gong et Jerry Y. Y. Heng. « The heterogeneous nucleation of pimelic acid under the effect of a template : experimental research and molecular simulation ». CrystEngComm 24, no 15 (2022) : 2825–35. http://dx.doi.org/10.1039/d1ce01591e.

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Leontiadis, Konstantinos, Dimitris S. Achilias et Ioannis Tsivintzelis. « Effect of the Filler Modification on the Thermal and Mechanical Properties of Composite Polypropylene/Wollastonite Drawn Fibers ». Polymers 15, no 14 (8 juillet 2023) : 2986. http://dx.doi.org/10.3390/polym15142986.

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Polypropylene (PP) is one of the most commercially used thermoplastics, while a significant amount of PP is used in the form of fibers. In this study, the effects of modification of the filler on the thermal and mechanical properties of composite polypropylene/wollastonite drawn fibers were investigated. In this direction, the surface modification of wollastonite with various organic acids, such as myristic, maleic, malonic glutaric, pimelic, and suberic acid, and the use of two solvents were studied. The surface-modified wollastonite particles were used to produce composite polypropylene drawn fibers. The modification efficiency was found to be slightly better when a non-polar solvent (carbon tetrachloride) was used instead of a polar one (ethanol). FTIR experiments showed that myristic, maleic, malonic, and pimelic acid can strongly interact with wollastonite’s surface. However, the mechanical strength of the composite fibers was not increased compared to that of the neat PP fibers, suggesting inadequate interactions between PP and wollastonite particles. Furthermore, it was observed that the drawing process increased around 10% the crystallinity of all samples. Wollastonite modified with malonic acid acted as a nucleating agent for β-crystals. The onset decomposition temperature increased by 5–10 °C for all samples containing 2% wollastonite, either modified or not. The suggested modifications of wollastonite might be more suitable for less hydrophobic polymers.
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14

Yan, Yan, Jia-Mei Chen et Tong-Bu Lu. « Thermodynamics and preliminary pharmaceutical characterization of a melatonin–pimelic acid cocrystal prepared by a melt crystallization method ». CrystEngComm 17, no 3 (2015) : 612–20. http://dx.doi.org/10.1039/c4ce01921k.

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15

Li, Hua, Juan Liu, Daokui Tang et Hongkai Wang. « Solubilities of Pimelic Acid in Ionic Liquids ». Industrial & ; Engineering Chemistry Research 50, no 17 (7 septembre 2011) : 10370–72. http://dx.doi.org/10.1021/ie200695w.

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Müller-Tautges, C., A. Eichler, M. Schwikowski, G. B. Pezzatti, M. Conedera et T. Hoffmann. « Historic records of organic compounds from a high Alpine glacier : influences of biomass burning, anthropogenic emissions, and dust transport ». Atmospheric Chemistry and Physics 16, no 2 (28 janvier 2016) : 1029–43. http://dx.doi.org/10.5194/acp-16-1029-2016.

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Abstract. Historic records of α-dicarbonyls (glyoxal, methylglyoxal), carboxylic acids (C6–C12 dicarboxylic acids, pinic acid, p-hydroxybenzoic acid, phthalic acid, 4-methylphthalic acid), and ions (oxalate, formate, calcium) were determined with annual resolution in an ice core from Grenzgletscher in the southern Swiss Alps, covering the time period from 1942 to 1993. Chemical analysis of the organic compounds was conducted using ultra-high-performance liquid chromatography (UHPLC) coupled to electrospray ionization high-resolution mass spectrometry (ESI-HRMS) for dicarbonyls and long-chain carboxylic acids and ion chromatography for short-chain carboxylates. Long-term records of the carboxylic acids and dicarbonyls, as well as their source apportionment, are reported for western Europe. This is the first study comprising long-term trends of dicarbonyls and long-chain dicarboxylic acids (C6–C12) in Alpine precipitation. Source assignment of the organic species present in the ice core was performed using principal component analysis. Our results suggest biomass burning, anthropogenic emissions, and transport of mineral dust to be the main parameters influencing the concentration of organic compounds. Ice core records of several highly correlated compounds (e.g., p-hydroxybenzoic acid, pinic acid, pimelic, and suberic acids) can be related to the forest fire history in southern Switzerland. P-hydroxybenzoic acid was found to be the best organic fire tracer in the study area, revealing the highest correlation with the burned area from fires. Historical records of methylglyoxal, phthalic acid, and dicarboxylic acids adipic acid, sebacic acid, and dodecanedioic acid are comparable with that of anthropogenic emissions of volatile organic compounds (VOCs). The small organic acids, oxalic acid and formic acid, are both highly correlated with calcium, suggesting their records to be affected by changing mineral dust transport to the drilling site.
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OHSUGI, Masahiro, Kayoko MIYAUCHI, Kayoko TACHIBANA et Shoko NAKAO. « Formation of a biotin precursor, pimelic acid, in yeasts from C18 fatty acids. » Journal of Nutritional Science and Vitaminology 34, no 4 (1988) : 343–52. http://dx.doi.org/10.3177/jnsv.34.343.

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Xiong, Chun, Xueyan Chen, Xiaolei Ding, Binyu Kuang, Xiangyu Pei, Zhengning Xu, Shikuan Yang, Huan Hu et Zhibin Wang. « Reconsideration of surface tension and phase state effects on cloud condensation nuclei activity based on the atomic force microscopy measurement ». Atmospheric Chemistry and Physics 22, no 24 (23 décembre 2022) : 16123–35. http://dx.doi.org/10.5194/acp-22-16123-2022.

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Abstract. Dicarboxylic acids are ubiquitous in atmospheric aerosol particles, but their roles as surfactants in cloud condensation nuclei (CCN) activity remain unclear. In this study, we investigated CCN activity of inorganic salt (sodium chloride and ammonium sulfate) and dicarboxylic acid (including malonic acid (MA), phenylmalonic acid (PhMA), succinic acid (SA), phenylsuccinic acid (PhSA), adipic acid (AA), pimelic acid (PA), and octanedioic acid (OA)), mixed particles with varied organic volume fractions (OVFs), and then directly determined their surface tension and phase state at high relative humidity (over 99.5 %) via atomic force microscopy (AFM). Our results show that CCN-derived κCCN of studied dicarboxylic acids ranged from 0.003 to 0.240. A linearly positive correlation between κCCN and solubility was obtained for slightly dissolved species, while negative correlation was found between κCCN and molecular volume for highly soluble species. For most inorganic salts and dicarboxylic acids (MA, PhMA, SA, PhSA and PA), a good closure within 30 % relative bias between κCCN and chemistry-derived κChem was obtained. However, κCCN values of inorganic salt–AA and inorganic salt–OA systems were surprisingly 0.3–3.0 times higher than κChem, which was attributed to surface tension reduction, as AFM results showed that their surface tensions were 20 %–42 % lower than that of water (72 mN m−1). Meanwhile, semisolid phase states were obtained for inorganic salt–AA and inorganic salt–OA and also affected hygroscopicity closure results. Our study highlights that surface tension reduction should be considered when investigating aerosol–cloud interactions.
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Adler, Heidi, et Heli Sirén. « Study on Dicarboxylic Acids in Aerosol Samples with Capillary Electrophoresis ». Journal of Analytical Methods in Chemistry 2014 (2014) : 1–10. http://dx.doi.org/10.1155/2014/498168.

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The research was performed to study the simultaneous detection of a homologous series ofα,ω-dicarboxylic acids (C2–C10), oxalic, malonic, succinic, glutaric, adipic, pimelic, suberic, azelaic, and sebacic acids, with capillary electrophoresis using indirect UV detection. Good separation efficiency in 2,6-pyridinedicarboxylic acid as background electrolyte modified with myristyl trimethyl ammonium bromide was obtained. The dicarboxylic acids were ionised and separated within five minutes. For the study, authentic samples were collected onto dry cellulose membrane filters of a cascade impactor (12 stages) from outdoor spring aerosols in an urban area. Hot water and ultrasonication extraction methods were used to isolate the acids from membrane filters. Due to the low concentrations of acids in the aerosols, the extracts were concentrated with solid-phase extraction (SPE) before determination. The enrichment of the carboxylic acids was between 86 and 134% with sample pretreatment followed by 100-time increase by preparation of the sample to 50 μL. Inaccuracy was optimised for all the sample processing steps. The aerosols contained dicarboxylic acids C2–C10. Then, mostly they contained C2, C5, and C10. Only one sample contained succinic acid. In the study, the concentrations of the acids in aerosols were lower than 10 ng/m3.
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Wu, Ze Xin, Wen Zhe Ma, Lei Wang, Chang Lin Yao, Shuang Song et Xin Yuan Wang. « Co-Amorphous Telmisartan-Pimelic Acid with Improved Solubility ». Materials Science Forum 993 (mai 2020) : 776–84. http://dx.doi.org/10.4028/www.scientific.net/msf.993.776.

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Telmisartan (TEL), a type of antihypertensive drug, has poor solubility. To improve its solubility, the co-amorphous telmisartan with pimelic acid (PA) in molar ratio of 1:1 and 2:1, respectively, were obtained using a liquid-assisted grinding method. The co-amorphous system was characterized by the powder X-ray diffraction and differential scanning calorimetry. The molecular interactions of the co-amorphous were studied by the infrared spectra. After the formation of co-amorphous, the solubility of TELwas much improved, and the apparent solubility values were approximately 9-15 times as high as that of crystalline TEL. Moreover, the co-amorphous TEL-PA was stored under 25 °C/20% RH for a month without any evidence of conversion by powder X-ray diffraction analysis.
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Li, Guohui, Dixuan Huang, Xue Sui, Shiyun Li, Bing Huang, Xiaojuan Zhang, Hui Wu et Yu Deng. « Advances in microbial production of medium-chain dicarboxylic acids for nylon materials ». Reaction Chemistry & ; Engineering 5, no 2 (2020) : 221–38. http://dx.doi.org/10.1039/c9re00338j.

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Medium-chain dicarboxylic acids (MDCAs) are widely used in the production of nylon materials, and among which, succinic, glutaric, adipic, pimelic, suberic, azelaic and sebacic acids are particularly important for that purpose.
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Hansen, A. M. K., K. Kristensen, Q. T. Nguyen, A. Zare, F. Cozzi, J. K. Nøjgaard, H. Skov et al. « Organosulfates and organic acids in Arctic aerosols : speciation, annual variation and concentration levels ». Atmospheric Chemistry and Physics 14, no 15 (7 août 2014) : 7807–23. http://dx.doi.org/10.5194/acp-14-7807-2014.

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Abstract. Sources, composition and occurrence of secondary organic aerosols in the Arctic were investigated at Zeppelin Mountain, Svalbard, and Station Nord, northeastern Greenland, during the full annual cycle of 2008 and 2010, respectively. Speciation of organic acids, organosulfates and nitrooxy organosulfates – from both anthropogenic and biogenic precursors were in focus. A total of 11 organic acids (terpenylic acid, benzoic acid, phthalic acid, pinic acid, suberic acid, azelaic acid, adipic acid, pimelic acid, pinonic acid, diaterpenylic acid acetate and 3-methyl-1,2,3-butanetricarboxylic acid), 12 organosulfates and 1 nitrooxy organosulfate were identified in aerosol samples from the two sites using a high-performance liquid chromatograph (HPLC) coupled to a quadrupole Time-of-Flight mass spectrometer. At Station Nord, compound concentrations followed a distinct annual pattern, where high mean concentrations of organosulfates (47 ± 14 ng m−3) and organic acids (11.5 ± 4 ng m−3) were observed in January, February and March, contrary to considerably lower mean concentrations of organosulfates (2 ± 3 ng m−3) and organic acids (2.2 ± 1 ng m−3) observed during the rest of the year. At Zeppelin Mountain, organosulfate and organic acid concentrations remained relatively constant during most of the year at a mean concentration of 15 ± 4 ng m−3 and 3.9 ± 1 ng m−3, respectively. However during four weeks of spring, remarkably higher concentrations of total organosulfates (23–36 ng m−3) and total organic acids (7–10 ng m−3) were observed. Elevated organosulfate and organic acid concentrations coincided with the Arctic haze period at both stations, where northern Eurasia was identified as the main source region. Air mass transport from northern Eurasia to Zeppelin Mountain was associated with a 100% increase in the number of detected organosulfate species compared with periods of air mass transport from the Arctic Ocean, Scandinavia and Greenland. The results from this study suggested that the presence of organic acids and organosulfates at Station Nord was mainly due to long-range transport, whereas indications of local sources were found for some compounds at Zeppelin Mountain. Furthermore, organosulfates contributed significantly to organic matter throughout the year at Zeppelin Mountain (annual mean of 13 ± 8%) and during Arctic haze at Station Nord (7 ± 2%), suggesting organosulfates to be important compounds in Arctic aerosols.
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Li, J. X., et W. L. Cheung. « Pimelic acid-based nucleating agents for hexagonal crystalline polypropylene ». Journal of Vinyl and Additive Technology 3, no 2 (juin 1997) : 151–56. http://dx.doi.org/10.1002/vnl.10182.

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Gündüz, Turgut, Esma Kiliç, Mustafa Tastekin et Güleren Ozkan. « Conductimetric titrations of symmetrical aliphatic dicarboxylic acids in solvents pyridine and pyridine–benzene mixtures ». Canadian Journal of Chemistry 68, no 3 (1 mars 1990) : 431–34. http://dx.doi.org/10.1139/v90-065.

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Nine symmetrical aliphatic dicarboxylic acids, namely oxalic, malonic, succinic, glutaric, adipic, pimelic, suberic, azelaic, and sebacic acids, were titrated conductimetrically with tetrabutylammonium hydroxide in pyridine and pyridine–benzene mixtures ((2 + 1), (1 + 1), (1 + 2), (1 + 3), and (1 + 4)). Titration curves of the acids exhibited two distinct and stoichiometric end-points in media of dielectric constants 13.5, 10.0, 8.2, 6.3, 5.3, and 4.7, respectively. The closer investigations of the titration curves revealed that three factors mainly influence the shapes of the titration curves: dielectric constant of the medium, number of the methylene groups in the acid, and formation of hydrogen bonds between several species. As dielectric constant of the medium decreases, conductivity of the medium also decreases at any point in the titration curve. Increase in the number of methylene groups from one to five decreases conductivity of the medium linearly at the first end-points of the acids, from then the conductivity becomes practically constant in acids having five to eight methylene groups in pyridine and pyridine–benzene mixtures of 2 + 1 and 1 + 1 ratios. Keywords: conductimetric titration in pyridine, conductimetric titration in pyridine–benzene mixtures, symmetrical aliphatic dicarboxilic acids.
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Ermer, Otto, Andreas Kusch et Christof Röbke. « Distorted Fivefold-Diamond Structure of 4,4-Bis(2-carboxyethyl)pimelic Acid (‘Methanetetrapropionic Acid’) ». Helvetica Chimica Acta 86, no 4 (avril 2003) : 922–29. http://dx.doi.org/10.1002/hlca.200390110.

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Cryle, Max J. « Selectivity in a barren landscape : the P450BioI–ACP complex ». Biochemical Society Transactions 38, no 4 (26 juillet 2010) : 934–39. http://dx.doi.org/10.1042/bst0380934.

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The cytochromes P450 (P450s) are a superfamily of oxidative haemoproteins that are capable of catalysing a vast range of oxidative transformations, including the oxidation of unactivated alkanes, often with high stereo- and regio-selectivity. Fatty acid hydroxylation by P450s is widespread across both bacteria and higher organisms, with the sites of oxidation and specificity of oxidation varying from system to system. Several key examples are discussed in the present article, with the focus on P450BioI (CYP107H1), a biosynthetic P450 found in the biotin operon of Bacillus subtilis. The biosynthetic function of P450BioI is the formation of pimelic acid, a biotin precursor, via a multiple-step oxidative cleavage of long-chain fatty acids. P450BioI is a member of an important subgroup of P450s that accept their substrates not free in solution, but rather presented by a separate carrier protein. Structural characterization of the P450BioI–ACP (acyl-carrier protein) complex has recently been performed, which has revealed the basis for the oxidation of the centre of the fatty acid chain. The P450BioI–ACP structure is the first such P450–carrier protein complex to be characterized structurally, with important implications for other biosynthetically intriguing P450–carrier protein complexes.
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Li, Hua, Xingli Jiao et Xiaoshuang Chen. « Thermodynamic analysis for solubility of pimelic acid in ionic liquids ». Russian Journal of Physical Chemistry A 88, no 7 (18 juin 2014) : 1133–37. http://dx.doi.org/10.1134/s0036024414070188.

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Bennett, M. J., M. C. Ragni, I. Hood et D. E. Hale. « Azelaic and pimelic acids : Metabolic intermediates or artefacts ? » Journal of Inherited Metabolic Disease 15, no 2 (mars 1992) : 220–23. http://dx.doi.org/10.1007/bf01799635.

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Amarandei, Cornelia, Romeo Iulian Olariu et Cecilia Arsene. « Implications of Matrix Effects in Quantitative HPLC/ESI-ToF-MS Analyses of Atmospheric Organic Aerosols ». Proceedings 55, no 1 (21 septembre 2020) : 6. http://dx.doi.org/10.3390/proceedings2020055006.

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Matrix-induced signal suppression or enhancements are known phenomena in electrospray ionization mass spectrometry. Very few studies report on method development for organic aerosols analyses with the evaluation of the matrix effects. The matrix effects lead to errors in the quantification of the analytes and affect the detection capability, precision, and accuracy of an analysis method. The present study reports on the matrix effects in the analysis of organic chemical compounds present in atmospheric aerosol particles collected on quartz filters. A total number of 19 analytes, including different classes of organic compounds, such as monoaromatic phenols and derivatives (e.g., catechol, 4-methylcatechol, 3-methoxycatechol, 4-nitrocatechol, 4-nitrophenol, 2,4-dinitrophenol, 2,6-dimethyl-4-nitrophenol), carboxylic acids (terebic acid, adipic acid, pimelic acid, phthalic acid, vanillic acid), and sulfonic acids (e.g., camphor-10-sulfonic acid), was investigated by high-performance liquid chromatography coupled to electrospray ionization time-of-flight mass spectrometry (HPLC/ESI-ToF-MS). The HPLC and ESI set-up parameters used in this study were previously optimized for the investigated compounds. Different volumes of a standard mixture were added to sample extracts, with final solutions concentrations in the 50–1500 μg L−1 range. For the investigated concentration range, the observed matrix effect was independent of the standard concentration level. For quartz filter extracts, the average matrix effect determined on a concentration-based method was 109.5 ± 6.1%. Both signal suppression and enhancement effects were observed for different compounds. For other analytes, the influence of the matrix effect is variable, suggesting that the use of an internal standard is not sufficient for the matrix effects correction. Competition between analyte ions and matrix components in the gas-phase ionization processes occurring in electrospray might explain signal suppression while generated coeluted isobaric compounds might induce signal enhancement.
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Subhapriya, P., P. S. Vijayanand et M. L. N. Madhu Mohan. « Synthesis and Characterization of Supramolecular Hydrogen-Bonded Liquid Crystals Comprising of p-n-Alkyloxy Benzoic Acids with Suberic Acid and Pimelic Acid ». Molecular Crystals and Liquid Crystals 571, no 1 (1 janvier 2013) : 40–56. http://dx.doi.org/10.1080/15421406.2012.741338.

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Ohsawa, Ikuroh, Tsugio Kisou, Kazuko Kodama, Ikuhiro Yoneda, Denis Speck, Rémi Gloeckler, Yves Lemoine et Kouichi Kamogawa. « Bioconversion of pimelic acid into biotin by Bacillus sphaericus bioB transformants ». Journal of Fermentation and Bioengineering 73, no 2 (1992) : 121–24. http://dx.doi.org/10.1016/0922-338x(92)90475-a.

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Li, Hua, Juan Liu, Jiang Zhu, Lei Zhao, Hongkai Wang et Yadong Zhang. « Correlation and comparison for solubility of pimelic acid in different solvents ». Russian Journal of Physical Chemistry A 86, no 2 (10 janvier 2012) : 314–16. http://dx.doi.org/10.1134/s0036024412020148.

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Hernáez, M. J., B. Floriano, J. J. Ríos et E. Santero. « Identification of a Hydratase and a Class II Aldolase Involved in Biodegradation of the Organic Solvent Tetralin ». Applied and Environmental Microbiology 68, no 10 (octobre 2002) : 4841–46. http://dx.doi.org/10.1128/aem.68.10.4841-4846.2002.

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ABSTRACT Two new genes whose products are involved in biodegradation of the organic solvent tetralin were identified. These genes, designated thnE and thnF, are located downstream of the previously identified thnD gene and code for a hydratase and an aldolase, respectively. A sequence comparison of enzymes similar to ThnE showed the significant similarity of hydratases involved in biodegradation pathways to 4-oxalocrotonate decarboxylases and established four separate groups of related enzymes. Consistent with the sequence information, characterization of the reaction catalyzed by ThnE showed that it hydrated a 10-carbon dicarboxylic acid. The only reaction product detected was the enol tautomer, 2,4-dihydroxydec-2-ene-1,10-dioic acid. The aldolase ThnF showed significant similarity to aldolases involved in different catabolic pathways whose substrates are dihydroxylated dicarboxylic acids and which yield pyruvate and a semialdehyde. The reaction products of the aldol cleavage reaction catalyzed by ThnF were identified as pyruvate and the seven-carbon acid pimelic semialdehyde. ThnF and similar aldolases showed conservation of the active site residues identified by the crystal structure of 2-dehydro-3-deoxy-galactarate aldolase, a class II aldolase with a novel reaction mechanism, suggesting that these similar enzymes are class II aldolases. In contrast, ThnF did not show similarity to 4-hydroxy-2-oxovalerate aldolases of other biodegradation pathways, which are significantly larger and apparently are class I aldolases.
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34

Maji, Siuli, Satendra Kumar et Sundararajan Kalyanasundaram. « Luminescence studies of uranyl-aliphatic dicarboxylic acid complexes in acetonitrile medium ». Radiochimica Acta 108, no 5 (28 avril 2020) : 361–73. http://dx.doi.org/10.1515/ract-2019-3131.

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AbstractThe uranyl (UO22+)-aliphatic dicarboxylic acid complexes are studied by luminescence and UV-Vis spectroscopy in acetonitrile (MeCN) medium. The ligands used are malonic acid (MA), succinic acid (SA), glutaric acid (GA), adipic acid (AA) and pimelic acid (PA). The complexes of UO22+ with the above ligands showed well resolved luminescence spectra at pH 4.0 with M/L = 5. Both luminescence and UV-Vis spectra indicated the formation of 1:2 and 1:3 complexes of UO22+ with MA and GA, AA, PA, respectively. DFT computations indicated the formation of 1:2 chelate complex of UO22+ with MA and two types of 1:3 complexes of UO22+ with SA, GA, AA and PA. Furthermore, the effect of solvent (water and acetonitrile) on the UO22+-ligand complexes has been performed using COSMO model. The present study demonstrates, for the first time, the formation of tris complexes of uranyl with these ligands in acetonitrile medium.
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Hansen, A. M. K., K. Kristensen, Q. T. Nguyen, A. Zare, F. Cozzi, J. K. Nøjgaard, H. Skov et al. « Organosulfates and organic acids in Arctic aerosols : speciation, annual variation and concentration levels ». Atmospheric Chemistry and Physics Discussions 14, no 4 (20 février 2014) : 4745–85. http://dx.doi.org/10.5194/acpd-14-4745-2014.

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Abstract. Sources, composition and occurrence of secondary organic aerosols (SOA) in the Arctic were investigated at Zeppelin Mountain, Svalbard, and Station Nord, northeast Greenland, during the full annual cycle of 2008 and 2010 respectively. We focused on the speciation of three types of SOA tracers: organic acids, organosulfates and nitrooxy organosulfates from both anthropogenic and biogenic precursors, here presenting organosulfate concentrations and compositions during a full annual cycle and chemical speciation of organosulfates in Arctic aerosols for the first time. Aerosol samples were analysed using High Performance Liquid Chromatography coupled to a quadrupole Time-of-Flight mass spectrometer (HPLC-q-TOF-MS). A total of 11 organic acids (terpenylic acid, benzoic acid, phthalic acid, pinic acid, suberic acid, azelaic acid, adipic acid, pimelic acid, pinonic acid, diaterpenylic acid acetate (DTAA) and 3-methyl-1,2,3-butanetricarboxylic acid (MBTCA)), 12 organosulfates and one nitrooxy organosulfate were identified at the two sites. Six out of the 12 organosulfates are reported for the first time. Concentrations of organosulfates follow a distinct annual pattern at Station Nord, where high concentration were observed in late winter and early spring, with a mean total concentration of 47 (±14) ng m−3, accounting for 7 (±2)% of total organic matter, contrary to a considerably lower organosulfate mean concentration of 2 (±3) ng m−3 (accounting for 1 (±1)% of total organic matter) observed during the rest of the year. The organic acids followed the same temporal trend as the organosulfates at Station Nord; however the variations in organic acid concentrations were less pronounced, with a total mean organic acid concentration of 11.5 (±4) ng m−3 (accounting for 1.7 (±0.6)% of total organic matter) in late winter and early spring, and 2.2 (±1) ng m−3 (accounting for 0.9 (±0.4)% of total organic matter) during the rest of the year. At Zeppelin Mountain, organosulfate and organic acid concentrations remained relatively constant during most of the year at amean concentration of 15 (±4) ng m−3 (accounting for 4 (±1)% of total organic matter) and 3.9 (±1) ng m−3 (accounting for 1.1 (±0.1)% of total organic matter) respectively. However during four weeks of spring remarkably higher concentrations of total organosulfates (23–36 ng m−3) and total organic acids (7–10 ng m−3) were observed. The periods of observed elevated organosulfate and organic acid concentration at Station Nord and at Zeppelin Mountain coincided with the Arctic Haze period. Furthermore, backwards air mass trajectories indicated northern Eurasia as the main source region of the Arctic haze aerosols at both sites. Periods with air mass transport from Russia to Zeppelin Mountain were associated with a doubled number of detected organosulfate species compared with periods of air mass transport from the Arctic Ocean, Scandinavia and Greenland. Our analysis showed the presence of organosulfates and organic acids of both biogenic and anthropogenic origin throughout the year at both Arctic sites. As the formation of organosulfates binds inorganic sulfate, their presence may possibly affect the formation and lifetime of clouds in the Arctic atmosphere.
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Shi, Peng, Shijie Xu, Huaiyu Yang, Songgu Wu, Weiwei Tang, Jingkang Wang et Junbo Gong. « Use of additives to regulate solute aggregation and direct conformational polymorph nucleation of pimelic acid ». IUCrJ 8, no 2 (6 février 2021) : 161–67. http://dx.doi.org/10.1107/s2052252521000063.

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Understanding the nucleation pathway and achieving regulation to produce the desired crystals are mutually beneficial. The authors previously proposed a nucleation pathway of conformational polymorphs in which solvation and solute self-assembly could affect the result of the conformational rearrangement and further nucleation outcomes. Based on this, herein α,ω-alkanedicarboxylic acids (DAn, where n represents the number of carbon atoms in the molecule, n = 2–6, 8–11) were designed as homologous additives to interfere with the self-assembly of pimelic acid (DA7) to further induce the form II compound, which differs from form I only in conformation. Interestingly, longer-chain additives (DA6–11) have a stronger form II-inducing ability than short-chain ones (DA2–4). In addition, an apparent gradient of the degree of interference with solute self-assembly, consistent with form II-inducing ability, was detected by infrared and nuclear magnetic resonance spectroscopy. The calculated molecular electrostatic potential charges also clearly indicate that additive–solute electrostatic interactions gradually increase with increasing carbon chain length of the additives, reaching a maximum value with DA6–11. This novel use of additives demonstrates a direct link between solute aggregation and conformational polymorph nucleation.
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37

Aitipamula, Srinivasulu, Annie B. H. Wong, Pui Shan Chow et Reginald B. H. Tan. « Polymorphism and phase transformations of a cocrystal of nicotinamide and pimelic acid ». CrystEngComm 14, no 23 (2012) : 8193. http://dx.doi.org/10.1039/c2ce26151k.

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Williams, Robert M., Myeong Nyeo Im et Jianhua Cao. « Asymmetric synthesis of 2,6-diamino-6-(hydroxymethyl)pimelic acid : assignment of stereochemistry ». Journal of the American Chemical Society 113, no 18 (août 1991) : 6976–81. http://dx.doi.org/10.1021/ja00018a040.

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39

Zhang, Zishou, Chunguang Wang, Zhang Junping et Kancheng Mai. « β-Nucleation of pimelic acid supported on metal oxides in isotactic polypropylene ». Polymer International 61, no 5 (18 janvier 2012) : 818–24. http://dx.doi.org/10.1002/pi.4148.

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40

Marsh, Aleksandra, Rachael E. H. Miles, Grazia Rovelli, Alexander G. Cowling, Lucy Nandy, Cari S. Dutcher et Jonathan P. Reid. « Influence of organic compound functionality on aerosol hygroscopicity : dicarboxylic acids, alkyl-substituents, sugars and amino acids ». Atmospheric Chemistry and Physics 17, no 9 (3 mai 2017) : 5583–99. http://dx.doi.org/10.5194/acp-17-5583-2017.

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Abstract. Hygroscopicity data for 36 organic compounds, including amino acids, organic acids, alcohols and sugars, are determined using a comparative kinetics electrodynamic balance (CK-EDB). The CK-EDB applies an electric field to trap-charged aqueous droplets in a chamber with controlled temperature and relative humidity (RH). The dual micro dispenser set-up allows for sequential trapping of probe and sample droplets for accurate determination of droplet water activities from 0.45 to > 0.99. Here, we validate and benchmark the CK-EDB for the homologous series of straight-chain dicarboxylic acids (oxalic–pimelic) with measurements in better agreement with Universal Quasichemical Functional Group Activity Coefficients (UNIFAC) predictions than the original data used to parametrise UNIFAC. Furthermore, a series of increasingly complex organic compounds, with subtle changes to molecular structure and branching, are used to rigorously assess the accuracy of predictions by UNIFAC, which does not explicitly account for molecular structure. We show that the changes in hygroscopicity that result from increased branching and chain length are poorly represented by UNIFAC, with UNIFAC under-predicting hygroscopicity. Similarly, amino acid hygroscopicity is under-predicted by UNIFAC predictions, a consequence of the original data used in the parametrisation of the molecular subgroups. New hygroscopicity data are also reported for a selection of alcohols and sugars and they show variable levels of agreement with predictions.
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41

Lee, Chia Yuan C., et Anthony L. Hines. « Adsorption of glutaric, adipic, and pimelic acids on activated carbon ». Journal of Chemical & ; Engineering Data 32, no 4 (octobre 1987) : 395–97. http://dx.doi.org/10.1021/je00050a001.

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42

Mekala, R., P. Jagdish et R. Mathammal. « Synthesis and structure identification of 2-amino-4, 6- dimethyl pyrimidine with gallic acid and pimelic acid ». Journal of Molecular Structure 1164 (juillet 2018) : 501–15. http://dx.doi.org/10.1016/j.molstruc.2018.03.059.

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43

Horányi, G., et E. M. Rizmayer. « Radiotracer study of the adsorption of pimelic acid at a platinized platinum electrode ». Electrochimica Acta 32, no 7 (juillet 1987) : 1057–62. http://dx.doi.org/10.1016/0013-4686(87)90033-8.

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44

Martinsson, Johan, Guillaume Monteil, Moa K. Sporre, Anne Maria Kaldal Hansen, Adam Kristensson, Kristina Eriksson Stenström, Erik Swietlicki et Marianne Glasius. « Exploring sources of biogenic secondary organic aerosol compounds using chemical analysis and the FLEXPART model ». Atmospheric Chemistry and Physics 17, no 18 (18 septembre 2017) : 11025–40. http://dx.doi.org/10.5194/acp-17-11025-2017.

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Abstract. Molecular tracers in secondary organic aerosols (SOAs) can provide information on origin of SOA, as well as regional scale processes involved in their formation. In this study 9 carboxylic acids, 11 organosulfates (OSs) and 2 nitrooxy organosulfates (NOSs) were determined in daily aerosol particle filter samples from Vavihill measurement station in southern Sweden during June and July 2012. Several of the observed compounds are photo-oxidation products from biogenic volatile organic compounds (BVOCs). Highest average mass concentrations were observed for carboxylic acids derived from fatty acids and monoterpenes (12. 3 ± 15. 6 and 13. 8 ± 11. 6 ng m−3, respectively). The FLEXPART model was used to link nine specific surface types to single measured compounds. It was found that the surface category sea and ocean was dominating the air mass exposure (56 %) but contributed to low mass concentration of observed chemical compounds. A principal component (PC) analysis identified four components, where the one with highest explanatory power (49 %) displayed clear impact of coniferous forest on measured mass concentration of a majority of the compounds. The three remaining PCs were more difficult to interpret, although azelaic, suberic, and pimelic acid were closely related to each other but not to any clear surface category. Hence, future studies should aim to deduce the biogenic sources and surface category of these compounds. This study bridges micro-level chemical speciation to air mass surface exposure at the macro level.
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45

Grzesiak, M., A. Rafalska-Łasocha et W. Łasocha. « Synthesis and XRPD studies of new barium dicarboxylates ». Powder Diffraction 26, no 1 (mars 2011) : 53–65. http://dx.doi.org/10.1154/1.3548073.

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New salts of barium with dicarboxylic acids (glutaric, adipic, pimelic, suberic, sebacic, and dodecanedioic) were synthesized and characterized by powder diffraction techniques. In addition to the basic crystallographic data and chemical analyses of barium glutarate hexahydrate {1}, barium adipate {2}, barium pimelate {3}, barium disuberate {4}, barium sebacate {5}, and barium dodecanedioate {6}, the processes of their thermal decomposition were investigated by XRPD. All the compounds decompose to barium carbonate at temperatures between 400 and 500 °C.
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46

Arnaud, Sacha Pérocheau, Linglin Wu, Maria-Angelica Wong Chang, James W. Comerford, Thomas J. Farmer, Maximilian Schmid, Fei Chang, Zheng Li et Mark Mascal. « New bio-based monomers : tuneable polyester properties using branched diols from biomass ». Faraday Discussions 202 (2017) : 61–77. http://dx.doi.org/10.1039/c7fd00057j.

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A family of monomers, including 2,5-hexandiol, 2,7-octandiol, 2,5-furandicarboxylic acid (FDCA), terephthalic acid (TA), and branched-chain adipic and pimelic acid derivatives, all find a common derivation in the biomass-derived platform molecule 5-(chloromethyl)furfural (CMF). The diol monomers, previously little known to polymer chemistry, have been combined with FDCA and TA derivatives to produce a range of novel polyesters. It is shown that the use of secondary diols leads to polymers with higher glass transition temperatures (Tg) than those prepared from their primary diol equivalents. Two methods of polymerisation were investigated, the first employing activation of the aromatic diacids via the corresponding diacid chlorides and the second using a transesterification procedure. Longer chain diols were found to be more reactive than the shorter chain alternatives, generally giving rise to higher molecular weight polymers, an effect shown to be most pronounced when using the transesterification route. Finally, novel diesters with high degrees of branching in their hydrocarbon chains are introduced as potential monomers for possible low surface energy materials applications.
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47

Manandhar, Miglena, et John E. Cronan. « Pimelic acid, the first precursor of theBacillus subtilisbiotin synthesis pathway, exists as the free acid and is assembled by fatty acid synthesis ». Molecular Microbiology 104, no 4 (3 mars 2017) : 595–607. http://dx.doi.org/10.1111/mmi.13648.

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Li, Hua, Jiang Zhu, Guoqin Hu, Pinliang Jiang, Lei Zhao et Yadong Zhang. « Measurement and Correlation of Solubility of Pimelic Acid in Ether, Tetrahydrofuran, Ethanol, and Methanol ». Journal of Chemical & ; Engineering Data 55, no 3 (11 mars 2010) : 1443–45. http://dx.doi.org/10.1021/je900629v.

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Flakus, Henryk T., et Artur Miros. « Infrared spectra of the hydrogen bond in pimelic acid crystals : polarization and temperature effects ». Spectrochimica Acta Part A : Molecular and Biomolecular Spectroscopy 57, no 12 (octobre 2001) : 2391–401. http://dx.doi.org/10.1016/s1386-1425(01)00404-8.

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Cooke, Claire L., Roger J. Davey, Simon Black, Chris Muryn et Robin G. Pritchard. « Binary and Ternary Phase Diagrams as Routes to Salt Discovery : Ephedrine and Pimelic Acid ». Crystal Growth & ; Design 10, no 12 (décembre 2010) : 5270–78. http://dx.doi.org/10.1021/cg1011296.

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