Sample records for 1,2-ethanediol

  1. The role of nonbonding interactions and the presence of fluoride on the conformational isomerism of 1,2-ethanediol

    Silva, Weslley G. D. P.; Silla, Josué M.; Cormanich, Rodrigo A.; Fernandes, Sergio A.; Freitas, Matheus P.


    This work reports the analysis of the effects ruling the conformational preference of 1,2-ethanediol (1,2-ED) using theoretical calculations, since there is no general consensus about the role of intramolecular hydrogen bond on the conformational isomerism of 1,2-ED. While the predominance of the gauche conformers along with the Osbnd Csbnd Csbnd O fragment relative to the trans ones was found to be mainly due to hyperconjugation, the orientation of the hydroxyl groups is better described by a balance between low steric hindrance and high stabilization from hyperconjugation than by intramolecular hydrogen bond. Nevertheless, the presence of a fluoride anion induces a conformational change in 1,2-ED that maximizes hydrogen bonds between the fluoride and the hydroxyl groups. This effect was observed experimentally by the shift of 1H(O) and 19F NMR signals upon complexation, then suggesting that compounds containing the 1,2-ED moiety can be possible anion transporters.

  2. Synthesis of 1-[6-Fluoro-(2S)-3H,4H-dihydro-2H-2-chromenyl]-(1R)-1,2- ethanediol and 1-[6-Fluoro-(2R)-3H,4H-dihydro-2H-2-chromenyl]- (1R)-1,2-ethanediol

    YU,An-Guang; WANG,Nai-Xing; ZHANG,Jun-Ping; YANG,Yun-Xu; WANG,Wu-Wei; SHENG,Rui-Long


    @@ Benzopyran compounds possess diverse pharmacological properties such as β-blockade, anticonvulsant and antimicrobial.[1,2] Our interest has been focused on the synthesis of 1-[6-Fluoro-2S]-3H,4H-dihydro-2H-2-chromenyl]-(1R)-1,2-ethanediol (6) and 1-[6-fluoro-(2R)-3H,4H-dihydro-2H-2-chromenyl]-(1R)-1,2-ethanediol (7) which are particularly convenient precursor to (S,R,R,R)-NE (8). 8 containing four asymmetrical carbon atoms was reported to be the most active isomer.[3] Chandrasekhar[4] has reported on the synthesis of 8. The key step to synthesize this compound is to obtain the chiral chromanone 6 and 7. 6 was accomplished in 8 steps by the Clasien rearrangement and a one-pot Sharpless asymmetric epoxidation, but the compound 7 was accomplished in 10 steps. Johannes[5] used Zr-catalytic kinetic resolution of allylic ethers and Mo-catalyzed chromene formation to synthesize 8 in 14 steps. However both of the methods request many synthetic steps and expensive reagents.

  3. The Determination of the Stereochemistry of Erythro-1,2-Diphenyl-1,2-Ethanediol: An Undergraduate Organic Experiment.

    Rowland, Alex T.


    Describes an undergraduate organic chemistry experiment designed to illustrate the power of nuclear magnetic reasonance spectroscopy in a determination of the configurations at centers of chirality of various isomers of acyclic systems. Provides a background discussion and experimental procedure. (JM)

  4. Self-assembled microstructures from 1,2-ethanediol suspensions of pure and binary mixtures of neutral and acidic biological galactosylceramides.

    Archibald, D D; Mann, S


    Optical and electron microscopy were employed to characterize microstructures formed by thermal mechanical treatment of glycol suspensions of various pure and binary mixtures of the brain-derived galactosphingolipids hydroxy fatty acid cerebroside (HFA-Cer), non-hydroxy fatty acid cerebroside (NFA-Cer) and sulfatide (S-Cer). Negative staining indicated some new features of the neutral cerebroside suspensions in glycol. HFA-Cer formed a small fraction of both unilamellar cylinders (ULCs) (lumina ca. 27 nm) and giant multilamellar cochleates in addition to the typical nonhelical multilamellar cylinders (MLCs) (lumina ca. 10-30 nm). NFA-Cer formed a gel composed of a significant fraction of very long ULCs (lumina ca. 17 nm) without helical substructure, in addition to multilamellar helical structures such as ribbons and cylinders (lumina ca. 70 nm). Anisotropic lamellar micelle-shards of NFA-Cer were also detected by negative staining. S-Cer formed short ULCs (lumina ca. 44 nm) with no obvious helical substructure. Complex mixture data are thought to result from thermodynamic and kinetic factors. HFA-Cer is highly insoluble and promotes a network of rigid intralamellar hydrogen bonding that tends to exclude other lipids. NFA-Cer stabilizes helical defects in the lamellae, and S-Cer enhances disorder or micellization. The processes of microstructure nucleation and lipid phase separation were affected by mixtures such that metastable microstructures were trapped or the length of lamellar cylinders was altered.

  5. Two New Compounds from Melanosciadum pimpinelloideum H. Boiss


    Two new compounds, melanochromone and 2-ethoxyl-2-(4-hydroxyphenyl)ethanol, were isolated from the whole plants of Melanosoiadum pimpinelloideum H. Boiss. The known compounds isolated were 1-(4-hydroxyphenyl)-1,2-ethanediol, tymine, cimifugin, umtatin, bergenin, daucosterol and stigmasterol. Their structures were determined on the basis of spectral data.

  6. A thermodynamic study of glucose and related oligomers in aqueous solution: Vapor pressures and enthalpies of mixing

    Cooke, S.A.; Jonsdottir, Svava Osk; Westh, Peter


    -mentioned systems at 318.15 K. A theoretical model is examined in which existing interaction parameters, calculated for the water + 1,2-ethanediol system by using a molecular mechanical approach, are incorporated into the UNIQUAC equation to describe the vapor pressures of the aforementioned series of saccharides...

  7. Planar Mn4O cluster homochiral metal-organic framework for HPLC separation of pharmaceutically important (±)-ibuprofen racemate.

    Hailili, Reshalaiti; Wang, Li; Qv, Junzhang; Yao, Ruxin; Zhang, Xian-Ming; Liu, Huwei


    A planar tetracoordinated oxygen containing a homochiral metal-organic framework (MOF) has been synthesized and characterized that can be used as a new chiral stationary phase in high-performance liquid chromatography to efficiently separate racemates such as pharmaceutically important (±)-ibuprofen and (±)-1-phenyl-1,2-ethanediol.

  8. UNIQUAC interaction parameters for molecules with -OH groups on adjacent carbon atoms in aqueous solution determined by molecular mechanics - glycols, glycerol and glucose

    Jonsdottir, Svava Osk; Klein, R. A.


    UNIQUAC interaction parameters have been determined, using molecular mechanics calculations, for 1,2-ethanediol, 1,2-propanediol, glycerol and glucose with water in aqueous solution. Conformational space for individual pairs of molecules was explored using a stochastic method, the Boltzmann Jump...... for the other systems. This gave results in good agreement with the experimental data.The possibility of transferring interaction parameters is very interesting,especially as it can be applied to systems for which the additivity principle of the UNIFAC method fails.Simulations were carried out for 1......,2-ethanediol, 1,2-propanediol and glycerol, surrounded by different numbers of water molecules. The interaction energy was observed to be linearly dependent on the number of water molecules present. This constant increment means that the additional interaction energy for each water molecule added is the same...

  9. An efficient synthesis of S-[gamma]-[(4-trifluoromethyl)phenoxy] benzenepropanamine-[1-[sup 14]C]maleate, an important metabolite of fluoxetine hydrochloride. [Antidepressant, serotonin uptake inhibitor

    Wheeler, W.J. (Lilly (Eli) and Co., Indianapolis, IN (United States). Lilly Research Labs.)


    S-[gamma]-[(4-Trifluoromethyl)phenoxy]benzenepropanamine-[1-[sup 14]C] maleate has been prepared in six steps from R-(-)1-phenyl-1,2-ethanediol. The isotope was incorporated by the reaction of NaCN-[[sup 14]C] with the tert. butyldimethylsilyl ether of R-(-)1-phenyl-1,2-ethane-diol 2-tosylate. Borane reduction and arylation, followed by salt formation yielded S-[gamma]-[(4-trifluoromethyl)phenoxy]benzenepropanamine-[1-[sup 14]C] maleate. (Author).

  10. JPRS Report, Science & Technology, USSR: Chemistry.


    with 15-40% water were in some cases stabilized with emulsifying agent, such as OP-7, yielding products with a shelf - life of 6-8 months. Two fuels...Ammonia From Nitrogen and Hydrogen Under Influence of Catalysts Based on Potassium Salts of Transition Metal Carbonyl Hydrides and Metallic Potassium ...Dissolution of Argon in Tetraethylammonium Iodide Solutions in 1,2-Ethanediol at 263-343 K (D.P. Kuz’min, G.A. Krestov; IZVESTIYA VYSSHIKH UCHEBNYKH

  11. Sol–gel derived Tb{sub 3}Fe{sub 5}O{sub 12} and Y{sub 3}Fe{sub 5}O{sub 12} garnets: Synthesis, phase purity, micro-structure and improved design of morphology

    Opuchovic, Olga, E-mail:; Beganskiene, Aldona; Kareiva, Aivaras


    Yttrium iron garnet (Y{sub 3}Fe{sub 5}O{sub 12}; YIG) and terbium iron garnet (Tb{sub 3}Fe{sub 5}O{sub 12}; TbIG) were prepared by an aqueous sol–gel method using two different complexing agents (1,2-ethanediol and glycerol). For the synthesis of Tb{sub 3}Fe{sub 5}O{sub 12} two different molar ratios of complexing agent (1:1 and 3:1) to the total metal ions were used. Thermogravimetric analysis (TG) and differential scanning calorimetry (DSC) were performed to study the thermal behaviour of the prepared Y–Fe–O and Tb–Fe–O precursor gels. The effects of synthesis parameters on the garnet phase formation were studied by X-ray powder diffraction (XRD) analysis and scanning electron microscopy (SEM). Interestingly, the XRD data indicated that single-phase Y{sub 3}Fe{sub 5}O{sub 12} garnet can be prepared only with 1,2-ethanediol at lowest 1000 °C temperature. While Tb{sub 3}Fe{sub 5}O{sub 12} garnet can be obtained at lower temperatures depending on the nature and amount of complexing agent. The SEM results showed that parameters of sol–gel processing influence the morphological features of garnets considerably. For comparison, the conventional solid-state reaction method at 1000 °C was also used for the fabrication of both Y{sub 3}Fe{sub 5}O{sub 12} and Tb{sub 3}Fe{sub 5}O{sub 12} garnets. - Highlights: • Y{sub 3}Fe{sub 5}O{sub 12} and Tb{sub 3}Fe{sub 5}O{sub 12} were prepared by aqueous sol–gel route. • Single-phase Y{sub 3}Fe{sub 5}O{sub 12} can be prepared with 1,2-ethanediol at 1000 °C temperature. • Tb{sub 3}Fe{sub 5}O{sub 12} can be obtained at lower temperatures depending on complexing agent.

  12. Glycolysis of poly (3-hydroxybutyrate) catalyzed by an enzyme system; Glicolise do poli(3-hidroxibutirato) por via enzimatica

    Campos, T.F.; Mano, V., E-mail: [Universidade Federal de Sao Joao del Rei (UFSJ), MG (Brazil). Dept. de Ciencias Naturais


    In this work we report the studies of PHB glycolysis catalyzed by lipase Amano PS (Pseudomonas cepacia) in the presence of 1,2-ethanediol (ethylene glycol). The reactions were performed in toluene:dichloroethane 3:1 (v/v) at 60 deg C, varying reaction time and concentration of ethylene glycol. PHB and the products of glycolysis (polyols) were characterized by FTIR, {sup 1}H-NMR, and TG. The FTIR spectra of polyols showed no significant change compared to the spectrum of PHB. The {sup 1}H-NMR spectra of the products of glycolysis showed signs of interest between 3 and 4.7 ppm, related to the ethylene glycol protons inserted in the polymer chain. By analyzing the thermograms we observed that the polyols are more thermally stable than PHB. (author)


    Kamil Klier; Richard G. Herman; James G.C. Shen; Qisheng Ma


    A novel 1,2-ethanediol, bis(hydrogen sulfate), disodium salt precursor-based solid acid catalyst with a zirconia substrate was synthesized and demonstrated to have significantly enhanced activity and high selectivity in producing methyl isobutyl ether (MIBE) or isobutene from methanol-isobutanol mixtures. The precursor salt was synthesized and provided by Dr. T. H. Kalantar of the M.E. Pruitt Research Center, Dow Chemical Co., Midland, MI 48674. Molecular modeling of the catalyst synthesis steps and of the alcohol coupling reaction is being carried out. A representation of the methyl transfer from the surface activated methanol molecule (left) to the activated oxygen of the isobutanol molecule (right) to form an ether linkage to yield MIBE is shown.

  14. Naphthalene decomposition in a DC corona radical shower discharge

    Ming-jiang NI; Xu SHEN; Xiang GAO; Zu-liang WU; Hao LU; Zhong-shan LI; Zhong-yang LUO; Ke-fa CEN


    The naphthalene decomposition in a corona radical shower discharge (CRS) was investigated, with attention paid to the influences of voltage and initial naphthalene density. The OH emission spectra were investigated so as to know the naphthalene decomposing process. The by-products were analyzed and a decomposing theory in discharge was proposed. The results showed that higher voltage and relative humidity were effective on decomposition. The initial concentration affected the decomposing efficiency of naphthalene. When the mitial naphthalene density was 17 mg/m3, the decomposition rate was found to be 70% under 14 kV. The main by-products were carbon dioxide and water. However, a small amount of carbonic oxide, 1, 2-ethanediol and acetaldehyde were found due to the incomplete oxidization.

  15. Sol-Gel Synthesis and Characterization of Selected Transition Metal Nano-Ferrites

    Aurelija GATELYTĖ


    Full Text Available In the present work, the sinterability and formation of nanosized yttrium iron garnet (Y3Fe5O12, yttrium perovskite ferrite (YFeO3, cobalt, nickel and zinc iron spinel (CoFe2O4, NiFe2O4 and ZnFe2O4, respectively powders by an aqueous sol-gel processes are investigated. The metal ions, generated by dissolving starting materials of transition metals in the diluted acetic acid were complexed by 1,2-ethanediol to obtain the precursors for the transition metal ferrite ceramics. The phase purity of synthesized nano-compounds was characterized by infrared spectroscopy (IR and powder X-ray diffraction analysis (XRD. The microstructural evolution and morphological features of obtained transition metal ferrites were studied by scanning electron microscopy (SEM.

  16. Cloning and expression of the gene encoding (R)-specific carbonyl reductase from Candida parapsilosis CCTCC M203011


    The gene which encodes (R)-specific carbonyl reductase (rCR) from Candida parapsilosis CCTCC M203011 was cloned, sequenced and compared with genes from the GenBank. The results indicated that rCR gene was 1011 bp, encoding a protein of 336 amino acids with a molecular weight of 35.9 kDa, and its nucleotide sequence showed 99% similarity to those of other members of the alcohol dehydrogenase superfamily. The rCR gene could express in recombinant strain Escherichia coli JM 109, and the expression plasmid could produce (R)-1-pheny-1,2-ethanediol (100% e.e., 80.14% yield) fromβ-hydroxyacetophenone without any additive to regenerate NAD+ from NADH.

  17. The world of DNA in glycol solution.

    Lindahl, Tomas


    The properties of high-molecular-weight DNA are usually investigated in neutral aqueous solutions. Strong acids and strong alkaline solutions are obviously unsuitable, as are corrosive solvents, and DNA is insoluble in most organic solvents; precipitation of DNA from aqueous solution with ethanol or isopropanol is therefore frequently used as a purification step. An exception is the organic solvent glycol (ethylene glycol, 1,2-ethanediol, dihydroxyethane, HOCH2CH2OH) and the similar solvent glycerol. Double-stranded DNA remains soluble in salt-containing glycol, although it precipitates in polyethylene glycol. (DNA also remains soluble in formamide, but the double-helical structure of DNA is much less stable in this solvent than in glycol.) However, DNA in glycol has been little investigated during the last half-century.

  18. Measurement of liquid-liquid equilibria for condensate + glycol and condensate + glycol + water systems

    Riaz, Muhammad; Kontogeorgis, Georgios; Stenby, Erling Halfdan


    Today's oil and gas production requires the application of various chemicals in large amounts. To evaluate the effects of those chemicals on the environment, it is of crucial importance to know how much of the chemicals are discharged via produced water and how much is dissolved in the crude oil....... The ultimate objective of this work is to develop a predictive thermodynamic model for the mutual solubility of oil, water, and polar chemicals. But for the development and validation of the model, experimental data are required. This work presents new experimental liquid-liquid equilibrium (LLE) data for 1......,2-ethanediol (MEG) + condensate and MEG + water + condensate systems at temperatures from (275 to 323) K at atmospheric pressure. The condensate used in this work is a stabilized natural gas condensate from an offshore field in the North Sea. Compositional analysis of the natural gas condensate was carried out...

  19. Degradation of corn stalk by the composite microbial system of MC1


    The composite microbial system of MC1 was used to degrade corn stalk in order to determine properties of the degraded products as well as bacterial composition of MC1. Results indicated that the pH of the fermentation broth was typical of lignocellulose degradatioin by MC1, decreasing in the early phase and increasing in later stages of the degradation. The microbial biomass peaked on the day 3 after degradation. The MC1 effeciently degraded the corn stalk by nearly 70% during which its cellulose content decreased by 71.2%, hemicellulose by 76.5% and lignin by 24.6%. The content of water-soluble carbohydrates (WSC) in the fermentation broth increased progressively during the first three days, and decreased thereafter, suggesting an accumulation of WSC in the early phase of the degradation process. Total levels of various volatile products peaked in the third day after degradation , and 7 types of volatile products were detected in the fermentation broth. These were ethanol, acetic acid, 1,2-ethanediol, propanoic acid, butanoic acid, 3-methyl-butanoic acid and glycerine. Six major compounds were quantitatively analysed and the contents of each compound were ethanol (0.584 g/L), acetic acid (0.735 g/L), 1,2-ethanediol (0.772 g/L), propanoic acid (0.026 g/L), butanoic acid (0.018 g/L) and glycerine (4.203 g/L). Characterization of bacterial cells collected from the culture solution, based on 16S rDNA PCR-DGGE analysis of DNAs, showed that the composition of bacterial community in MC1 coincided basically with observations from previous studies. This indicated that the structure of MC1 is very stable during degradation of different lignocellulose materials.

  20. Highly selective anti-Prelog synthesis of optically active aryl alcohols by recombinant Escherichia coli expressing stereospecific alcohol dehydrogenase.

    Li, Ming; Nie, Yao; Mu, Xiao Qing; Zhang, Rongzhen; Xu, Yan


    Biocatalytic asymmetric synthesis has been widely used for preparation of optically active chiral alcohols as the important intermediates and precursors of active pharmaceutical ingredients. However, the available whole-cell system involving anti-Prelog specific alcohol dehydrogenase is yet limited. A recombinant Escherichia coli system expressing anti-Prelog stereospecific alcohol dehydrogenase from Candida parapsilosis was established as a whole-cell system for catalyzing asymmetric reduction of aryl ketones to anti-Prelog configured alcohols. Using 2-hydroxyacetophenone as the substrate, reaction factors including pH, cell status, and substrate concentration had obvious impacts on the outcome of whole-cell biocatalysis, and xylose was found to be an available auxiliary substrate for intracellular cofactor regeneration, by which (S)-1-phenyl-1,2-ethanediol was achieved with an optical purity of 97%e.e. and yield of 89% under the substrate concentration of 5 g/L. Additionally, the feasibility of the recombinant cells toward different aryl ketones was investigated, and most of the corresponding chiral alcohol products were obtained with an optical purity over 95%e.e. Therefore, the whole-cell system involving recombinant stereospecific alcohol dehydrogenase was constructed as an efficient biocatalyst for highly enantioselective anti-Prelog synthesis of optically active aryl alcohols and would be promising in the pharmaceutical industry.

  1. Water-deficit impact on fatty acid and essential oil composition and antioxidant activities of cumin (Cuminum cyminum L.) aerial parts.

    Bettaieb, Iness; Knioua, Sana; Hamrouni, Ibtissem; Limam, Ferid; Marzouk, Brahim


    This study is designed to examine the effect of water deficit on growth, fatty acid and essential oil composition, and antioxidant activities of Cuminum cyminum aerial part extracts. Plants were treated with different levels of water deficit: control (C), moderate water deficit (MWD), and severe water deficit (SWD). Plant growth (height, fresh and dry matter weights) as well as yield components were significantly increased under moderate water deficit and conversely reduced at severe level. Total fatty acid content decreased significantly with severity of constraint. Drought reduced considerably the proportions of major fatty acids and the unsaturated to saturated fatty acid ratio. The essential oil yield was 0.14% (based on the dry weight); it increased by 2.21-fold at MWD but decreased by 42.8% under SWD in comparison to the control. Drought results in the modification of the essential oil chemotype from 1-phenyl-1-butanol to 1-phenyl-1,2-ethanediol. Antioxidant activities of the acetone extracts were determined by two complementary test systems, namely, DPPH and β-carotene/linoleic acid. The highest activity was exhibited by moderately stressed plants and was reduced significantly under SWD. In control plants, the total phenolic amount was 10.23 mg GAE/g DW, which increased by 1.5-fold under MWD and decreased by 42% under SWD.

  2. Computational and experimental studies of 2-[(E)-hydrazinylidenemethyl]-6-methoxy-4-[(E)-phenyldiazenyl]phenol and its tautomers

    Sayin, Koray; Kurtoglu, Nurcan; Kose, Muhammet; Karakas, Duran; Kurtoglu, Mukerrem


    A new azo-chromophore group containing a hydrazine-Schiff base compound, 2-[(E)-hydrazinylidenemethyl]-6-methoxy-4-[(E)-phenyldiazenyl]phenol, was synthesized and structurally characterized by single crystal X-ray diffraction study. The compound was found to crystallise in orthorhombic crystal system with Pca2(1) space group. In the structure, the molecule exhibits a phenol-imine intramolecular hydrogen bond and the sbnd NH2 group also involves in intermolecular hydrogen bonding with one of the nitrogen atom of the azo group (-Ndbnd N-) forming a 1D zigzag chain. Computational studies were performed on the titled compound and its tautomers. As computationally, this compound and its tautomers were optimized by using M062X/6-311G(d,p) level. According to thermodynamic parameters, the most stable tautomer was found to be azo-enol form. This result was then taken into account and spectral studies, which are IR, UV-Vis and NMR spectra, of this compound were performed and examined in detail. All calculations were performed at gas phase (ε = 1.000), 2-propanol (ε = 19.264), 1,2-ethanediol (ε = 40.245), water (ε = 78.355), formamide (ε = 108.940) and N-methylformamide-mixture (ε = 181.560).

  3. Synthesis and characterization of new hydroxycarboxylate compounds obtained in the redox reaction between Fe(NO{sub 3}){sub 3} and diol

    Stefanescu, O., E-mail: [Politehnica University of Timisoara, Faculty of Industrial Chemistry and Environmental Engineering, P-ta Victoriei No. 2, Timisoara, RO-300006 (Romania); Vlase, T.; Vlase, G.; Doca, N. [West University of Timisoara, Research Center for Thermal Analysis in Environmental Problems, Str. Pestalozzi No. 16, Timisoara, RO-300115 (Romania); Stefanescu, M. [Politehnica University of Timisoara, Faculty of Industrial Chemistry and Environmental Engineering, P-ta Victoriei No. 2, Timisoara, RO-300006 (Romania)


    Highlights: {yields} New hydroxycarboxylate compounds obtained in the redox reaction Fe(NO{sub 3}){sub 3}-diols. {yields} Octahedral stereochemistry with [Fe(III)O{sub 6}] chromophore for the synthesized complexes. {yields} Fe(III) glyoxylate and succinate as precursors of iron oxide {gamma}-Fe{sub 2}O{sub 3} nanoparticles. - Abstract: The paper presents experimental studies and structural investigations of two new Fe(III) hydroxycarboxylate coordination compounds. The homopolynuclear complex combinations of Fe(III) glyoxylate and succinate type were obtained in the redox reaction between Fe(NO{sub 3}){sub 3} and diols (1,2-ethanediol and 1,4-butanediol). The synthesized coordination compounds and the products formed during their thermal conversion were characterized by thermal analysis (in air and nitrogen), FT-IR and UV-VIS spectrometry, Moessbauer spectrometry, electron microscopy and XRD. By thermal decomposition of the complex combinations, at 300 {sup o}C, the well crystallized pure phase {gamma}-Fe{sub 2}O{sub 3} as nanoparticles were formed.

  4. Purification and characterization of a novel carbonyl reductase with high stereo-selectivity

    YANG Ming; XU Yan; MU Xiaoqing; XIAO Rong


    A novel NADPH-dependent carbonyl reductase was separated from Candida parapsilosis CCTCC 203011.The enzyme gave a single band on sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE),which was purified through ammonium sulfate,Diethylamino Ethanol (DEAE) sepharose Fast flow (FF),phenyl-sepharose FF and blue sepharose FF chromatography from cell-free extract.The molecular mass of the enzyme was about 30 kDa.The optimum pH and temperature for reduction were 4.5℃ and 35℃,respectively.The Cu2+ had strong restrictive effect on enzyme activity.In addition,the carbonyl reductase was an enzyme with high substrate specificity and stereo-selectivity,and showed high asymmetric reduction activity towards α-hydroxyacetophenone and ethyl 4-chloro acetoacetate.For the asymmetric reduction of α-hydroxyacetophenone and ethyl 4-chloro acetoacetate,(S)-1-phenyl-1,2-ethanediol and (R)-ethyl 4-chloro-3-hydroxybutanoate were produced by the purified enzyme,with the 100% and 94.3% e.e.value,respectively.Therefore,the enzyme could be one of the effective biocatalysts for asymmetric synthesis of chiral alcohols.The amino acid sequences of one peptide from the purified enzyme were analyzed by LC-MASS-MASS,and the carbonyl reductase showed some identity to the hypothetical protein CaO 19.10414 reported.

  5. Use of hydrophilic ionic liquids in a two-phase system to improve Mung bean epoxide hydrolases-mediated asymmetric hydrolysis of styrene oxide.

    Chen, Wen-Jing; Lou, Wen-Yong; Yu, Chun-Yang; Wu, Hong; Zong, Min-Hua; Smith, Thomas J


    A comparative study was made of Mung bean epoxide hydrolases-catalyzed asymmetric hydrolysis of styrene oxide to (R)-1-phenyl-1,2-ethanediol in an n-hexane/buffer biphasic system containing various hydrophilic ionic liquids (ILs). Compared to the n-hexane/buffer biphasic system alone, addition of a small amount of hydrophilic ILs reduced the amount of non-enzymatic hydrolysis, and improved the reaction rate by up to 22%. The ILs with cation containing an alkanol group, namely [C(2)OHMIM][BF(4)] and [C(2)OHMIM][TfO], and the choline amino acid ILs [Ch][Arg] and [Ch][Pro] were found to be the most suitable co-solvents for the reaction, owing to their good biocompatibility with the enzyme, which led to high initial rates (0.99-1.25 μmol/min) and high product e.e.s (95%). When substrate concentration was around 30 mM, where optimal performance was observed with the IL-containing systems, the product e.e. was improved from 90% without ILs to ≥95% in the presence of ILs.

  6. Time-dependent radiolytic yields at room temperature and temperature-dependent absorption spectra of the solvated electrons in polyols


    The molar extinction coefficients at the absorption maximum of the solvated electron spectrum have been evaluated to be 900, 970, and 1000 mol-1·m2 for 1,2-ethanediol (12ED), 1,2-propanediol (12PD), and 1,3-propanediol (13PD), respectively. These values are two-third or three-fourth of the value usually reported in the published report.Picosecond pulse radiolysis studies have aided in depicting the radiolytic yield of the solvated electron in these solvents as a function of time from picosecond to microsecond. The radiolytic yield in these viscous solvents is found to be strongly different from that of the water solution. The temperature dependent absorption spectra of the solvated electron in 12ED, 12PD, and 13PD have been also investigated. In all the three solvents, the optical spectra shift to the red with increasing temperature. While the shape of the spectra does not change in 13PD, a widening on the blue side of the absorption band is observed in 12ED and 12PD at elevated temperatures.

  7. Hydrotreating of wheat straw in toluene and ethanol.

    Murnieks, Raimonds; Kampars, Valdis; Malins, Kristaps; Apseniece, Lauma


    In the present work, wheat straw was hydroliquefied at a temperature of 300°C for 4h in ethanol or toluene in order to obtain bio-components which are useful for fuel purposes. The experiments were performed in a 100mL batch reactor under hydrogen pressure of 70 bar. Typically, 2g of straw and 0.1g of catalyst (66%Ni/SiO2-Al2O3) were dispersed in 15 g of solvent. The main compounds of the oil produced during the liquefaction of hemicellulose, cellulose and lignin of wheat straw in both solvents are: tetrahydrofuran-2-methanol, 1,2-butanediol and butyrolactone. Besides the mentioned compounds, ethanol favoured the decomposition of bigger molecules to short-chain alcohols such as 1-butanol, 1,2-propanediol and 1,2-ethanediol. Toluene contributes to the production of furans and other cyclic compounds. The light fractions distilled together with the solvent also contain the following: 1-propanol, 2-methyl-cyclopentanone, acetic acid and ethyl acetate.

  8. Supercritical gasification of wastewater from updraft wood gasifiers

    Di Blasi, Colomba; Branca, Carmen; Galgano, Antonio [Dipartimento di Ingegneria Chimica, Universita degli Studi di Napoli Federico II, Napoli (Italy); Meier, Dietrich; Brodzinski, Ina [Institute of Wood Chemistry, Hamburg (Germany); Malmros, Olof [KommuneKemi, Nyborg (Denmark)


    Supercritical water gasification (SCWG) of the wood tar fraction soluble in water is discussed. The mixture is collected downstream of an updraft wood gasification plant and presents tar compounds typical of low-temperature pyrolysis, with the highest yields attained by acetic acid, levoglucosan and 1-hydroxy-2-propanone. SCWG tests, using a laboratory-scale reactor with a plug-flow behavior, temperatures of 723-821 K, residence times of 46-114 s and initial total organic carbon (TOC) contents of 6.5-31 g/l (pressure equal to 25 MPa), show TOC conversion roughly between 30% and 70%. The corresponding yields of gas (l) with respect to the initial TOC contents (g) vary from 0.4 to 1. Gasification of TOC is well described by an irreversible, first-order, Arrhenius rate reaction with an activation energy of 75.7{+-}22 kJ/mol and a pre-exponential factor of 897{+-}30 s{sup -1}. Quantification of 23 tar compounds of the product stream shows the prompt conversion of sugars and complex phenols, with the formation of intermediate products, such as furfurals, which successively decompose, and more thermally resistant species, such as acetic acid, propionic acid, 1,2-ethanediol, ketones and especially cresols and phenols. (author)

  9. Enhancing the anaerobic digestion of corn stalks using composite microbial pretreatment.

    Yuan, Xufeng; Li, Peipei; Wang, Hui; Wang, Xiaofen; Cheng, Xu; Cui, Zongjun


    A composite microbial system (XDC-2) was used to pretreat and hydrolyze corn stalk to enhance anaerobic digestion. The results of pretreatment indicated that sCOD concentrations of hydrolysate were highest (8,233 mg/l) at the fifth day. XDC-2 efficiently degraded the corn stalk by nearly 45%, decreasing the cellulose content by 22.7% and the hemicellulose content by 74.1%. Total levels of volatile products peaked on the fifth day. The six major compounds present were ethanol (0.29 g/l), acetic acid (0.55 g/l), 1,2-ethanediol (0.49 g/l), propionic acid (0.15 g/l), butyric acid (0.22 g/l), and glycerine (2.48 g/l). The results of anaerobic digestion showed that corn stalks treated by XDC-2 produced 68.3% more total biogas and 87.9% more total methane than untreated controls. The technical digestion time for the treated corn stalks was 35.7% shorter than without treatment. The composite microbial system pretreatment could be a cost-effective and environmentally friendly microbial method for efficient biological conversion of corn stalk into bioenergy.

  10. Thermodynamic study on some alkanediol solutions: Measurement and modeling

    Moosavi, Mehrdad; Motahari, Ahmad; Omrani, Abdollah, E-mail:; Rostami, Abbas Ali


    Highlights: • Measuring densities and viscosities for binary mixtures of some alkanediols. • Finding excess molar volume, partial molar volume and thermal expansion coefficient. • Fitting excess molar volume values with PFP and Redlich–Kister polynomial equations. • Deducing excess Gibbs free energy of activation and other thermodynamic parameters. • Predicting viscosity values with different single parameter semi empirical equations. - Abstract: The densities ρ and viscosities η of 1,2-ethanediol with 1,2-propanediol or 1,3-propanediol, and 1,2-propanediol with 1,3-propanediol binary liquid mixtures over the entire concentration range at temperatures (298.15 to 308.15) K with 5 K interval were measured. The experimental data were used to calculate the excess molar volume V{sub m}{sup E}, partial molar volume V{sup ¯}{sub m,i}, partial molar volume at infinite dilution V{sup ¯}{sub i}{sup ∞}, apparent molar volume V{sub φi}, coefficient of thermal expansion α{sub p}, excess coefficient of thermal expansion α{sub p}{sup E}, excess viscosity η{sup E}, excess Gibbs energy of activation ΔG{sup *E}, and other thermodynamic parameters. A Redlich–Kister equation and Prigogine–Flory–Patterson (PFP) model was applied to correlate the excess molar volume results. Moreover, the viscosity data were correlated with the Grunberg–Nissan, Tamura–Kurata, Hind–Ubbelohde and Katti–Chaudhary equations. Good agreement was found between experimental data and modeling results.

  11. The genome of Pelobacter carbinolicus reveals surprising metabolic capabilities and physiological features

    Aklujkar Muktak


    Full Text Available Abstract Background The bacterium Pelobacter carbinolicus is able to grow by fermentation, syntrophic hydrogen/formate transfer, or electron transfer to sulfur from short-chain alcohols, hydrogen or formate; it does not oxidize acetate and is not known to ferment any sugars or grow autotrophically. The genome of P. carbinolicus was sequenced in order to understand its metabolic capabilities and physiological features in comparison with its relatives, acetate-oxidizing Geobacter species. Results Pathways were predicted for catabolism of known substrates: 2,3-butanediol, acetoin, glycerol, 1,2-ethanediol, ethanolamine, choline and ethanol. Multiple isozymes of 2,3-butanediol dehydrogenase, ATP synthase and [FeFe]-hydrogenase were differentiated and assigned roles according to their structural properties and genomic contexts. The absence of asparagine synthetase and the presence of a mutant tRNA for asparagine encoded among RNA-active enzymes suggest that P. carbinolicus may make asparaginyl-tRNA in a novel way. Catabolic glutamate dehydrogenases were discovered, implying that the tricarboxylic acid (TCA cycle can function catabolically. A phosphotransferase system for uptake of sugars was discovered, along with enzymes that function in 2,3-butanediol production. Pyruvate:ferredoxin/flavodoxin oxidoreductase was identified as a potential bottleneck in both the supply of oxaloacetate for oxidation of acetate by the TCA cycle and the connection of glycolysis to production of ethanol. The P. carbinolicus genome was found to encode autotransporters and various appendages, including three proteins with similarity to the geopilin of electroconductive nanowires. Conclusions Several surprising metabolic capabilities and physiological features were predicted from the genome of P. carbinolicus, suggesting that it is more versatile than anticipated.

  12. Substrate dependent reaction channels of the Wolff–Kishner reduction reaction: A theoretical study

    Shinichi Yamabe


    Full Text Available Wolff–Kishner reduction reactions were investigated by DFT calculations for the first time. B3LYP/6-311+G(d,p SCRF=(PCM, solvent = 1,2-ethanediol optimizations were carried out. To investigate the role of the base catalyst, the base-free reaction was examined by the use of acetone, hydrazine (H2N–NH2 and (H2O8. A ready reaction channel of acetone → acetone hydrazine (Me2C=N–NH2 was obtained. The channel involves two likely proton-transfer routes. However, it was found that the base-free reaction was unlikely at the N2 extrusion step from the isopropyl diimine intermediate (Me2C(H–N=N–H. Two base-catalyzed reactions were investigated by models of the ketone, H2N–NH2 and OH−(H2O7. Here, ketones are acetone and acetophenone. While routes of the ketone → hydrazone → diimine are similar, those from the diimines are different. From the isopropyl diimine, the N2 extrusion and the C–H bond formation takes place concomitantly. The concomitance leads to the propane product concertedly. From the (1-phenylethyl substituted diimine, a carbanion intermediate is formed. The para carbon of the phenyl ring of the anion is subject to the protonation, which leads to a 3-ethylidene-1,4-cyclohexadiene intermediate. Its [1,5]-hydrogen migration gives the ethylbenzene product. For both ketone substrates, the diimines undergoing E2 reactions were found to be key intermediates.


    Kamil Klier; Richard G. Herman; Heock-Hoi Kwon; James G. C. Shen; Qisheng Ma; Robert A. Hunsicker; Andrew P. Butler; Scott J. Bollinger


    A tungstena-zirconia (WZ) catalyst has been investigated for coupling methanol and isobutanol to unsymmetrical ethers, i.e. methyl isobutyl ether (MIBE) and compared with earlier studied sulfated-zirconia (SZ) and Nafion-H catalysts. In all cases, the ether synthesis mechanism is a dual site S{sub N}2 process involving competitive adsorption of reactants on proximal acid sites. At low reaction temperatures, methylisobutylether (MIBE) is the predominant product. However, at temperatures >135 C the WZ catalyst is very good for dehydration of isobutanol to isobutene. The surface acid sites of the WZ catalyst and a Nafion-H catalyst were diagnosed by high resolution X-ray photoelectron spectroscopy (XPS) of N 1s shifts after adsorption of amines. Using pyridine, ethylenediamine, and triethylamine, it is shown that WZ has heterogeneous strong Broensted acid sites. Theoretical study located the transition state of the alcohol coupling reaction on proximal Broensted acid sites and accounted well for XPS core-level shifts upon surface acid-base interactions. While computations have not been carried out with WZ, it is shown that the SZ catalyst is a slightly stronger acid than CF{sub 3}SO{sub 3}H (a model for Nafion-H) by 1.3-1.4 kcal/mol. A novel sulfated zirconia catalyst having proximal strong Broensted acid sites was synthesized and shown to have significantly enhanced activity and high selectivity in producing MIBE or isobutene from methanol/isobutanol mixtures. The catalyst was prepared by anchoring 1,2-ethanediol bis(hydrogen sulfate) salt precursor onto zirconium hydroxide, followed by calcination to remove the -(CH{sub 2}CH{sub 2})- bridging residues.

  14. [Degradation of cassava residue by the cellulose degradation composite microbial system MC1].

    Guo, Peng; Wang, Xiao-Fen; Zhu, Wan-Bin; Cheng, Xu; Cui, Zong-Jun


    The lignocelluloses of cassava residue are good biomass resources. They are mainly used to produce feeds and alcohol. It is a promising approach to utilize them to produce methane. But it is difficult to use cassava residue for producing methane because of its dispersive solid matter and much water. A cellulose degradation composite microbial system MC1 was applied to degrade cassava residue discarded from cassava starch manufactory, and the composition of the lignocelluloses and the soluble ingredients of cassava residue were analyzed. After 18 days' cultivation, the total weight of the cassava residue was reduced by 47.3%, the cellulose, hemi-cellulose and lignin of the cassava residue were reduced by 22.7%, 90.4% and 11.3%, respectively, and 85% of the whole weight relief was made by MC1 within 6 days. The soluble ingredients of the cassava residue were increased from the incipient 18% to 33% in the third day which was the peak value in the process. The total amount of the volatile products, analyzed by GC-MS, came to a maximum in the sixth day. Twelve kinds of volatile products in the fermentation broth were determined, in which ethanol, acetic acid, 1, 2-ethanediol, butanoic acid and glycerine were the major compounds, and they can be utilized by methanogenic organism directly or be changed into compounds that can be utilized by methanogens organism directly. Accordingly, it is very hopeful to use MC1 to degrade cassava residue as a method of prefermentation in methane fermentation.

  15. Experiments and simulations of NOx formation in the combustion of hydroxylated fuels

    Bohon, Myles


    This work investigates the influence of molecular structure in hydroxylated fuels (i.e. fuels with one or more hydroxyl groups), such as alcohols and polyols, on NOx formation. The fuels studied are three lower alcohols (methanol, ethanol, and n-propanol), two diols (1,2-ethanediol and 1,2-propanediol), and one triol (1,2,3-propanetriol); all of which are liquids at room temperature and span a wide range of thermophysical properties. Experimental stack emissions measurements of NO/NO2, CO, and CO2 and flame temperature profiles utilizing a rake of thermocouples were obtained in globally lean, swirling, liquid atomized spray flames inside a refractory-lined combustion chamber as a function of the atomizing air flow rate and swirl number. These experiments show significantly lower NOx formation with increasing fuel oxygen content despite similarities in the flame temperature profiles. By controlling the temperature profiles, the contribution to NOx formation through the thermal mechanism were matched, and variations in the contribution through non-thermal NOx formation pathways are observed. Simulations in a perfectly stirred reactor, at conditions representative of those measured within the combustion region, were conducted as a function of temperature and equivalence ratio. The simulations employed a detailed high temperature chemical kinetic model for NOx formation from hydroxylated fuels developed based on recent alcohol combustion models and extended to include polyol combustion chemistry. These simulations provide a qualitative comparison to the range of temperatures and equivalence ratios observed in complex swirling flows and provide insight into the influence of variations in the fuel decomposition pathways on NOx formation. It is observed that increasing the fuel bound oxygen concentration ultimately reduces the formation of NOx by increasing the proportion of fuel oxidized through formaldehyde, as opposed to acetylene or acetaldehyde

  16. How polar are choline chloride-based deep eutectic solvents?

    Pandey, Ashish; Rai, Rewa; Pal, Mahi; Pandey, Siddharth


    Developing and characterizing green solvents with low toxicity and cost is one of the most important issues in chemistry. Deep Eutectic Solvents (DESs), in this regard, have shown tremendous promise. Compared to popular organic solvents, DESs possess negligible VOCs and are non-flammable. Compared to ionic liquids, which share many characteristics but are ionic compounds and not ionic mixtures, DESs are cheaper to make, much less toxic and mostly biodegradable. An estimate of the polarity associated with DESs is essential if they are to be used as green alternatives to common organic solvents in industries and academia. As no one physical parameter can satisfactorily represent solute-solvent interactions within a medium, polarity of DESs is assessed through solvatochromic optical spectroscopic responses of several UV-vis absorbance and molecular fluorescence probes. Information on the local microenvironment (i.e., the cybotactic region) that surrounds several solvatochromic probes [betaine dye, pyrene, pyrene-1-carboxaldehyde, 1-anilino-8-naphthalene sulfonate (ANS), p-toluidinyl-6-naphthalene sulfonate (TNS), 6-propionyl-2-(dimethylaminonaphthalene) (PRODAN), coumarin-153, and Nile Red] for four common and popular DESs formed from choline chloride combined with 1,2-ethanediol, glycerol, urea, and malonic acid, respectively, in 1 : 2 molar ratios termed ethaline, glyceline, reline, and maline is obtained and used to assess the effective polarity afforded by each of these DESs. The four DESs as indicated by these probe responses are found to be fairly dipolar in nature. Absorbance probe betaine dye and fluorescence probes ANS, TNS, PRODAN, coumarin-153, and Nile Red, whose solvatochromic responses are based on photoinduced charge-transfer, imply ethaline and glyceline, DESs formed using alcohol-based H-bond donors, to be relatively more dipolar in nature as compared to reline and maline. The pyrene polarity scale, which is based on polarity-induced changes in

  17. Reactivity of polyfunctional alcohols towards atmospheric radicals in the aqueous solution

    Hoffmann, D.; Herrmann, H.


    Alcohols such as ethylene glycol, propylene glycol and glycerol are widely used compounds in numerous applications. The oxidation of these compounds can influence the tropospheric oxidation budget as well as contribute significantly to the formation of low volatile organic particle constituents, such as mono- and dicarboxylic acids. Model simulations applying the multiphase chemistry mechanism CAPRAM 3.0i (Chemical Aqueous Phase Radical Mechanism) show that the aqueous phase oxidation of ethylene glycol contribute significantly to the formation of the known particle constituent oxalic acid under remote (up to 1.7%) and urban (up to 9.5%) conditions. Due to their high solubility oxidation processes of polyalcohols will take place mainly in the aqueous solution. Oxidation reactions of alcohols are triggered by reactions with atmospheric radicals such as OH, NO3 and SO4-. However, for the detailed implementation of the tropospheric degradation of alcohols in atmospheric chemistry mechanisms many kinetic data, in particular as a function of the temperature, are still needed. Therefore, the reactivity of 1,2-ethanediol (ethylene glycol), 1,2-propanediol (propylene glycol), 1,3-propanediol, 1,2,3-propanetriol (glycerol), 1,2-butanediol, 1,4-butanediol and 1,5-pentanediol was systematically investigated towards OH, NO3 and SO4- radicals in the aqueous solution. All kinetic measurements were done as a function of the temperature. During these experiments the temperature of the measurement solution was varied between 278 ≤ T [K] ≤ 318. Experiments were carried out using laser flash photolysis technique at a wavelength of 248 nm. Rate constants were measured directly or using competition kinetics in case of OH. The kinetic data and activation parameters obtained will be summarized and discussed with available literature data. Furthermore, the data obtained will be discussed in terms of reactivity correlations and atmospheric relevance. A more detailed implementation of

  18. Effect of boiling and roasting on the fermentation of soybeans into dawadawa (soy-dawadawa).

    Dakwa, Sarah; Sakyi-Dawson, Esther; Diako, Charles; Annan, Nana Takyiwa; Amoa-Awua, Wisdom Kofi


    Soybeans which had initially been dehulled by either boiling (boiled/dehulled) or roasting (roasted/dehulled) before peeling, were cooked and fermented into dawadawa, a traditional food condiment. The micropopulation, enzymatic activities, proximate composition, amino acid, and aroma profiles of the two types of soybean dawadawa were evaluated during fermentation. Only minor differences were found in the microbial profiles of the two types of soy-dawadawa. Although boiled/dehulled soy-dawadawa initially had lower microbial counts, it recorded higher counts at the advanced stages of fermentation. Proteolytic and amylolytic Bacillus species including Bacillus subtilis, Bacillus pumilus, Bacillus licheniformis, Bacillus cereus, and Bacillus firmus dominated the micropopulation of the two types of soy-dawadawa with Bacillus subtilis accounting for about 50% of the Bacillus species in all samples. Lactic acid bacteria and yeasts occurred in low numbers in the two types of soy-dawadawa. The proximate composition of the two types of soy-dawadawa were similar, and their contents of moisture and protein increased whilst fat and ash decreased during fermentation. Both types of fermenting soy-dawadawa recorded similar levels of alpha-amylase activity, but boiled/dehulled soy-dawadawa showed slightly higher protease activity. The levels of isoleucine, leucine, lysine, phenylalanine, arginine and proline increased significantly with fermentation time in both types of soy-dawadawa. With respect to differences in their aroma profiles, hexanodecanol, octadecyl acetate, 1,2-dimethyl benzene, tetradecene, (E)-5-eicosene, cyclohexadecane, and hexacosane were found only in the roasted/dehulled samples, whilst 1,2-ethanediol, ethyl acetate, dimethyl disulfide, cyclotetradecane, decene, indole , 2 butyl-octenal, acetophenone, and toluene were found only in the boiled/dehulled samples. A market focus group showed preference for roasted/dehulled soy-dawadawa over boiled/dehulled soy

  19. Novel technologies to improve the performance of biomass pyrolsis systems

    Liaw, Shi-Shen

    by grouping them in five groups or families. The C1 family is formed by products of cellulose fragmentation reactions (glycoaldehyde, acetol, 1,2-ethanediol, monoacetate, butanedial). The products grouped in the C2 family (levoglucosan, levoglucosenone, 1,4:3,6-dianhydro-alpha-D-glucopyranose) are derived from cellulose depolymerization reactions. The molecules derived from hemicellulose (Acetic acid, furfural, 2-furanmethanol) were grouped in the H family. The products derived from lignin were grouped in two families L1 (derived from p-hydroxyl phenol (H) and guaiacyl (G) structures) and L2 (derived from syringyl (S) structures). The yield and properties of bio-oil obtained from an auger pyrolysis reactor is comparable with other existing fluidized bed reactors in the similar pyrolysis condition. The system proposed required much lower volumes of carrier gas and result in the production of a sand-free bio-char. It was also found that the reactions leadings to the formation of bio-char products and the yield of bio-oil are not affected if the pretreatment (torrefaction) temperature is maintained below 290 °C. Torrefaction at higher temperatures results in a dramatic reduction of the bio-oil yield and an increase in the bio-char yield. A condensation system coupled with the auger pyrolysis reactor was constructed and studied for the separation of crude bio-oil produced from Douglas Fir wood. As the first condenser temperature increases up to 80 °C, the content of light oxygenated organic compounds (chiefly the acetic acid and water) in the first condenser decreased significantly. For the first time, this dissertation reports the anaerobic digestion of the aqueous phase obtained in the thermal pretreatment (torrefaction) step and in the second condenser during biomass pyrolysis to produce bio-methane. Acid washing was studied to minimize the inhibitors (hydroxyacetaldehyde and monophenols) in aqueous phase for higher bio-methane production. The results of this