Pentyl Alcohol Research Articles

Comparative description of the extraordinary phenomenon "thermally activated isobaric partial structure compaction" of water as a solute in some alkanols and alkylamines

This review summarises the data available in the literature. It also includes the authors' published results of precision densimetric measurements. The research concerns with the physically unusual phenomenon of "thermally activated isobaric partial densification of the structure" (TIPCS) of dissolved water, or its so-called "negative partial molar expandability" (NPEA) in several organic solvents. They contain amphiproton hydroxyl-containing media of three alcohols: methyl alcohol (MA), tertiary butyl alcohol (TBAlcohol), and amyl or pentyl alcohol (TPA), so asprotophilic media of two amines: tert butylamine (TBAmine) and ethylenediamine (EDA). The discussed TIPCS phenomenon, associated with a decrease in the standard (partial at infinite dilution) volume of solvated water with increasing temperature, was discovered about half a century ago in alkanol solutions of H2O and recently - in water-containing media of alkylamines. However, nowadays this extraordinary effect has not yet found its physically based interpretation. It allows ones to predict the possibility of TIPCS occurrence in the binary liquid-phase system specifically selected for the study. Our comprehensive data analysis allowed us to make several inferences regarding the main characteristics of a standard solution of H2O in an organic solvent. They cause extraordinary changes in the volume of the formed solvatocomplex of water under the influence of increasing temperature. Firstly, the energy parameters of the intermolecular interaction (relative affinity) water solvent noticeably dominate over those of the solvent-solvent interaction. Those differences become more evident with increasing temperature. Secondly, a higher rate of thermal expansion of the organic solvent structure in volume (inbulk) is found than influence of temperature on structural packing of the resulting mixed molecular aggregate or water solvates complex. Thirdly, the difference in the parameters of water-solvent and solvent-solvent interactions depends not only on the proton-donor/acceptor properties of the molecules contacting in solution, but also on the configuration of the structural packing of the solvating medium. It determines the nature of steric hindrances to the formation of H-bonds. Therefore, the absolute values of the mentioned parameters of relative affinity at 298.15 K increase in the series: MA << EDA ≈ TBAmine < TPAlcohol < TBAmine. It can indicate a relative strengthening of the specific interaction (mainly through the formation of hydrogen bonds) between the molecules of water and amphiprotonic or protophilic solvent in the above sequence. Indeed, difference in the solvent-solvent and water-solvent hydrogen bonding energies in the discussed liquid media of alkylamines (TBAmine and EDA) and tertiary isomeric alkanols (TBAlcohol and TPA) - with the most evident basicity - turned out to be noticeably larger than in the structural packing of water methanol solution. The ability of the components to specific interactions is quite comparable in those compounds.

Сравнительная характеристика неординарного явления «термоактивируемого изобарического парциального уплотнения структуры» воды как растворенного вещества в некоторых алканолах и алкиламинах

This review summarises the data available in the literature. It also includes the authors' published results of precision densimetric measurements. The research concerns with the physically unusual phenomenon of "thermally activated isobaric partial densification of the structure" (TIPCS) of dissolved water, or its so-called "negative partial molar expandability" (NPEA) in several organic solvents. They contain amphiproton hydroxyl-containing media of three alcohols: methyl alcohol (MA), tertiary butyl alcohol (TBAlcohol), and amyl or pentyl alcohol (TPA), so asprotophilic media of two amines: tert butylamine (TBAmine) and ethylenediamine (EDA). The discussed TIPCS phenomenon, associated with a decrease in the standard (partial at infinite dilution) volume of solvated water with increasing temperature, was discovered about half a century ago in alkanol solutions of H2O and recently - in water-containing media of alkylamines. However, nowadays this extraordinary effect has not yet found its physically based interpretation. It allows ones to predict the possibility of TIPCS occurrence in the binary liquid-phase system specifically selected for the study. Our comprehensive data analysis allowed us to make several inferences regarding the main characteristics of a standard solution of H2O in an organic solvent. They cause extraordinary changes in the volume of the formed solvatocomplex of water under the influence of increasing temperature. Firstly, the energy parameters of the intermolecular interaction (relative affinity) water solvent noticeably dominate over those of the solvent-solvent interaction. Those differences become more evident with increasing temperature. Secondly, a higher rate of thermal expansion of the organic solvent structure in volume (inbulk) is found than influence of temperature on structural packing of the resulting mixed molecular aggregate or water solvates complex. Thirdly, the difference in the parameters of water-solvent and solvent-solvent interactions depends not only on the proton-donor/acceptor properties of the molecules contacting in solution, but also on the configuration of the structural packing of the solvating medium. It determines the nature of steric hindrances to the formation of H-bonds. Therefore, the absolute values of the mentioned parameters of relative affinity at 298.15 K increase in the series: MA << EDA ≈ TBAmine < TPAlcohol < TBAmine. It can indicate a relative strengthening of the specific interaction (mainly through the formation of hydrogen bonds) between the molecules of water and amphiprotonic or protophilic solvent in the above sequence. Indeed, difference in the solvent-solvent and water-solvent hydrogen bonding energies in the discussed liquid media of alkylamines (TBAmine and EDA) and tertiary isomeric alkanols (TBAlcohol and TPA) - with the most evident basicity - turned out to be noticeably larger than in the structural packing of water methanol solution. The ability of the components to specific interactions is quite comparable in those compounds.

Effect of Solvent Topography and Steric Hindrance on Crystal Morphology

Effect of steric hindrance resulting from solvent topography on the resultant crystal morphology was examined via cooling crystallization of various carboxylic acids in isomeric butyl and pentyl alcohols. Our experiments show that the magnitude of hindrance is related to the degree of branching at the substituted carbon, with hindrance increasing in the order of 1° < 2° < 3° alcohols. The resulting crystals displayed a trend of low, intermediate, and high aspect ratios, corresponding to 1°, 2°, and 3° alcohols, respectively. In particular, 3° alcohols have a tendency to yield significantly different crystal morphologies, compared to 1° and 2° alcohols. Hence, the position of the hydroxyl functional group plays a major role in enhancing or limiting solute–solvent hydrogen bonding interactions and thereby influencing the resultant crystal morphology. A simple molecular model, with succinic acid as test case, was used to demonstrate the extended hydrogen bonding network and surface chemistry binding at the d...

Pentanol and Benzyl Alcohol Attack Bacterial Surface Structures Differently.

The genus Methylobacterium tolerates hygiene agents like benzalkonium chloride (BAC), and infection with this organism is an important public health issue. Here, we found that the combination of BAC with particular alcohols at nonlethal concentrations in terms of their solitary uses significantly reduced bacterial viability after only 5 min of exposure. Among the alcohols, Raman spectroscopic analyses showed that pentanol (pentyl alcohol [PeA]) and benzyl alcohol (BzA) accelerated the cellular accumulation of BAC. Fluorescence spectroscopic assays and morphological assays with giant vesicles indicated that PeA rarely attacked membrane structures, while BzA increased the membrane fluidity and destabilized the structures. Other fluorescent spectroscopic assays indicated that PeA and BzA inactivate bacterial membrane proteins, including an efflux pump for BAC transportation. These findings suggested that the inactivation of membrane proteins by PeA and BzA led to the cellular accumulation but that only BzA also enhanced BAC penetration by membrane fluidization at nonlethal concentrations.

Lateral Dynamics of Surfactants at the Free Water Surface: A Computer Simulation Study

Molecular dynamics simulations of the adsorption layer of five different surfactant molecules, i.e., pentyl alcohol, octyl alcohol, dodecyl alcohol, sodium dodecyl sulfate, and dodecyl trimethyl ammonium chloride are performed at the free surface of their aqueous solution at two surface densities, namely 1 and 4 μmol/m(2) at 298 K. The results are analyzed in terms of the two-dimensional single molecule dynamics, in particlular, lateral diffusion of the surfactants at the liquid surface, in order to distinguish between two possible adsorption scenarios, namely the assumptions of localized and mobile surfactants. The obtained results, in accordance with the dynamical nature of the liquid phase and liquid surface, clearly support the latter scenario, as the time scale of lateral diffusion of the surfactant molecules is found to be comparable with that of the three-dimensional diffusion of water in the bulk liquid phase. The mechanism of this lateral diffusion is also investigated in detail by calculating binding energy distribution of the water molecules in the first hydration shell of the surfactant headgroups and that of the nonfirst shell surface waters, and by calculating the mean residence time of the water molecules in the first hydration shell of the surfactant headgroups. This time is found to be at least an order of magnitude smaller than the characteristic time of the lateral diffusion of the surfactants, revealing that surfactant molecules move without their first shell hydration water neighbors at the surface.

Cholesteric Liquid Crystals Doped with Dodecylamine for Detecting Aldehyde Vapors

In this paper, we report a study of using cholesteric liquid crystals (CLCs) doped with dodecylamine for detecting aldehyde vapors. CLCs doped with dodecylamine show color change from red to yellow-green upon exposure to 300 ppmv pentyl aldehyde within 60 s. In contrast, no colorimetric response is observed when pure CLCs are used. Characterization by using FT-IR shows that the possible mechanism responsible for the colorimetric response is the formation of an imine bond between dodecylamine and pentyl aldehyde. A new C=N peak at 1670 cm(-1) appears in the spectrum after the exposure to aldehyde vapors. The CLCs doped with dodecylamine show good selectivity for pentyl aldehyde; they do not respond to 200 ppmv pentyl alcohol, pentylamine, acetone, ethanol, and water vapor. This study demonstrates the potential applications of doped CLCs as low-cost and portable gas sensors.

The production of myco-diesel hydrocarbons and their derivatives by the endophytic fungus Gliocladium roseum (NRRL 50072)

An endophytic fungus, Gliocladium roseum (NRRL 50072), produced a series of volatile hydrocarbons and hydrocarbon derivatives on an oatmeal-based agar under microaerophilic conditions as analysed by solid-phase micro-extraction (SPME)-GC/MS. As an example, this organism produced an extensive series of the acetic acid esters of straight-chained alkanes including those of pentyl, hexyl, heptyl, octyl, sec-octyl and decyl alcohols. Other hydrocarbons were also produced by this organism, including undecane, 2,6-dimethyl; decane, 3,3,5-trimethyl; cyclohexene, 4-methyl; decane, 3,3,6-trimethyl; and undecane, 4,4-dimethyl. Volatile hydrocarbons were also produced on a cellulose-based medium, including heptane, octane, benzene, and some branched hydrocarbons. An extract of the host plant, Eucryphia cordifolia (ulmo), supported the growth and hydrocarbon production of this fungus. Quantification of volatile organic compounds, as measured by proton transfer mass spectrometry (PTR-MS), indicated a level of organic substances in the order of 80 p.p.m.v. (parts per million by volume) in the air space above the oatmeal agar medium in an 18 day old culture. Scaling the PTR-MS profile the acetic acid heptyl ester was quantified (at 500 p.p.b.v.) and subsequently the amount of each compound in the GC/MS profile could be estimated; all yielded a total value of about 4.0 p.p.m.v. The hydrocarbon profile of G. roseum contains a number of compounds normally associated with diesel fuel and so the volatiles of this fungus have been dubbed 'myco-diesel'. Extraction of liquid cultures of the fungus revealed the presence of numerous fatty acids and other lipids. All of these findings have implications in energy production and utilization.

Structure-activity relationships of (S,Z)-2-aminopurine methylenecyclopropane analogues of nucleosides. Variation of purine-6 substituents and activity against herpesviruses and hepatitis B virus.

A series of 13 new (S,Z)-2-aminopurine methylenecyclopropane analogues was synthesized, and their antiviral activity was investigated. The nucleophilic displacement of chlorine of 2-amino-6-chloropurine derivative 5 with allyl-, propargyl-, cyclopropylmethyl-, isopropyl-, benzyl-, cyclohexyl-, and 2-hydroxyethylamine gave N(6)-alkyl compounds 2a, 2b, 2c, 2d, 2e,2f, and 2g. A similar reaction of 5 with allyl, cyclopropylmethyl, propyl, or pentyl alcohol catalyzed by K(2)CO(3) afforded O(6)-alkyl analogues 3a, 3c, 3h and 3i. Propane- and pentanethiol furnished S(6)-alkyl compounds 4h and 4i. The N(6)-alkyl derivatives 2a, 2b, O(6) analogues 3a, 3c, 3h, 3i, and S(6) compounds 4h, 4i which were highly effective in all CMV assays and exhibited the lowest cytotoxicity in proliferating HFF cells appear to be good candidates for in vivo assays. Activity of new analogues against HSV-1 or HSV-2 was restricted to BSC-1 and Vero cultures. Compounds 2c, 2b, 3a and 3h were effective against EBV in one of two assays (Daudi or H-1). Analogues 3a and 4i were the most active anti-VZV agents whereas compounds 3h, 3i, and 4h inhibited the replication of HBV in a micromolar concentration range.

Densities and Viscosities for Binary Mixtures of Anisole with Pentyl Alcohol Isomers

Densities and viscosities were measured for the binary mixtures of anisole with 2-pentanol, 3-pentanol, 2-methyl-1-butanol, 2-methyl-2-butanol, 3-methyl-1-butanol, and 3-methyl-2-butanol at 303.15 K, 313.15 K, and 323.15 K over the entire composition range. The excess volumes and viscosity deviations were calculated from the experimental data and are correlated by a Redlich−Kister type equation. McAllister's three-body and four-body interaction models were also used to correlate the kinematic viscosities.

Anodic stripping voltammetric determination of total lead, copper and selenium in whole blood and blood serum

A two-step procedure including appropriate wet-digestions, separation of selenium from interfering ions such as heavy metal ions with pentyl alcohol and anodic stripping voltammetric (ASV) determination of Pb2+, Cu2+ and SeO32– is developed. The elements in digested whole blood and serum sample solutions were determined by using a standard addition method. 1 × 10–9 mol/L SeO2–3, Cu2+ and Pb2+ were successfully determined with relative standard deviations of approximately 1–2% (n = 6–8).

Continuous extraction of vanadium(V) and iron(III) with acetylacetone under high-speed stirring with Teflon phase separator.

A continuous extraction system consisting of a distillation flask, an extraction flask (Morton flask) containing a high speed stirrer and a Teflon phase separator was investigated. The utility of the system was examined by the separation and concentration of V(V) and Fe(III) with acetylacetone(AA).m-Xylene was selected as the extraction solvent because distillation took place at about 140°C. Fe(III) was easily extracted into the organic solvent with AA. On the other hand, V(V) was not extracted with AA without adding pentyl alcohol. Therefore, V(V) was extracted by the synergism between AA and pentyl alcohol. The effect of stirring speed was examined on the extractions of V(V) and Fe(III). The recommended procedure for the stepwise determination of V(V) and Fe(III) was as follows: A solvent mixture ofm-xylene (15 cm3)and AA(1 cm3) was added to the sample solution (50 cm3, pH 4) containing Fe(III) and V(V) in the Morton flask (200cm3) containing a stirring rod and a Teflon phase separator. The stirring speed was kept at 1800 rpm. The rate of solvent-transport by the Peristaltic pump was regulated at 1.6 cm3/min. The extraction was stopped after 30 min and the distillation flask containing the concentrate for Fe(III) analysis was removed. The distillation flask in the extraction-apparatus was then exchanged and 1 cm3 of pentyl alcohol and 0.5 cm3 of AA were added to the extraction solvent in the Morton flask. Subsequently, 1 cm3 of 8 mol dm-3 HCl solution was added in order to adjust the pH to 2.5. The extraction was then performed again. After 60 min, the absorbance of the concentrated extract was measured at 449 nm after dilution to 10 cm3 with m-xylene. Similarly, the amount of Fe(III) in the previous flask was determined at 437 nm. The metal ions were quantitatively extracted by the proposed method. The extractability of V(V) by this batch method was 63%. The determination ranges of V(V) and Fe(III) were 20100 μg and 1080 μg, respectively.

Determination of alcohol partial molar volumes from single-droplet gravimetric and optical resonance data

The molar volume of pentyl alcohol in dibutylphthalate (DBP) is determined from weight changes in a DBP droplet during alcohol vapor absorption in conjunction with volumetric changes that are determined from optical resonance spectra.

Determination of selenium(IV) by anodic stripping voltammetry using extraction with pentyl alcohol

A method is described for the specific and accurate determination of Se in samples by anodic stripping voltammetry following separation of the Se with pentyl alcohol. The separation procedure removes CuII ions with a single extraction. After the extraction, the acidic solution can be used for the determination of CuII because most of these ions remain in the solution. The height of the anodic stripping peak and the standard additions method were used as a quantitative measurement. Following the extraction, 1 × 10–9 mol dm–3 Se can be determined; the relative standard deviation is 1%(n= 4).

Mössbauer spectroscopic investigation of the sorption of iron by polyether-type polyurethane-foam sorbents

The results of a study on the nature of the iron species sorbed by polyether-type open-cell polyurethane (PU) foam membranes are presented. The study has included freshly prepared anionic 57FeIII–halo complexes and 57Fe(SCN)3, in addition to the cationic 57FeII–phenanthroline complex. Conclusions concerning the most probable nature of the sorbed species have been drawn from the comparison of Mossbauer spectra for frozen Fe—PU foam complexes with the spectra for corresponding iron-containing frozen aqueous solutions and extracts in suitable organic solvents. For FeIII compounds, diethyl ether, and for the FeII complex, acetone, pentyl alcohol and nitrobenzene were used as organic solvents. The spectra were recorded at 80 K and evaluated to obtain isomer shifts, quadrupole splittings and internal magnetic fields for different iron species.

ChemInform Abstract: Homolytic Reactions of Ligated Boranes. Part 14. ESR Studies of Ring Opening of Cycloalkylaminyl‐Borane Radicals and Reactions of Aminyl‐Borane Radicals with Silicon‐Containing Compounds.

AbstractAminyl‐borane radicals (II) are generated photochemically from amine‐boranes such as (I) either in cyclopropane/oxirane or in tBuOH/tert.‐pentyl alcohol.

Interaction of Divalent Metal Acids with Pentyl Alcohol and Isopentyl Acetate

Abstract Extraction of monobasic divalent metal bromo acids in pentyl alcohol–benzene and isopentyl acetate–benzene mixtures was studied at room temperature (25 °C). Three molecules of pentyl alcohol ae well as of isopentyl acetate were associated with each metal acid molecule of cobalt and copper in the organic phase. Zinc, cadmium, and mercury acids take up two molecules of pentyl alcohol and one molecule of isopentyl acetate. Metal acids studied here mostly exist as monomer in the organic phase. In pentyl alcohol, however, copper acid is monomeric only at lower concentrations (4×10−5 to 2×10−4M) and dimeric at higher concentrations (3.3×10−4 to 1.4×10−3M).

Carboxylesterases in the respiratory tracts of rabbits, rats and syrian hamsters

Esters are a widespread class of organic compounds found both in industry and the environment. Because esters are often volatile and, therefore, readily inhaled, the capacity of respiratory tract tissues as well as liver S-9 homogenates from rats, rabbits, and Syrian hamsters to hydrolyze a variety of esters was investigated. A new technique to determine hydrolysis rates by measuring carboxylic acid residues using ion chromatography was proven effective. The results indicated that esters, including potentially carcinogenic β-lactones, are readily hydrolyzed by respiratory tract enzymes. Species and tissue differences were apparent. The nasal ethmoturbinates had especially high levels of esterase activity with tissue weight-normalized activities from rabbits and hamsters for most substrates exceeding all other tissues tested, including liver. Phenyl acetate was the most rapidly hydrolyzed by ethmoturbinate tissue of the esters tested. Among straight chain aliphatic alcohol acetates, hydrolysis rates increased with carbon number up to pentyl alcohol and then decreased. Branched 4-carbon alcohol acetates were less rapidly hydrolyzed than n-butyl acetate. Correlation of hydrophobicity constants with hydrolysis rates indicated that, for the straight chain aliphatic acetates, a bilinear model best fit the data.

Hydrates of Organic Compounds. V. The Clathrate Hydration of Alcohols

Abstract A new method for examining the ability of a given substance to form a hydrate with the same structure as that of a reference substance has been established. By using this method, for a series of alcohols ranging from methyl alcohol to pentyl alcohol, including their isomers, the ability to form a clathrate hydrate of either Structure I or Structure II has been investigated. It has been found that: (1) methyl alcohol has the ability to form both Structure I and II hydrates; (2) ethyl alcohol has the ability to form a Structure II hydrate; (3) all C3-alcohols (propyl, isopropyl, allyl, and propargyl alcohol) can actually form Structure II hydrates with relatively high (around −10 °C) incongruent melting points, and (4) among the C4- and C5-alcohols, only t-butyl alcohol has the ability to form a Structure II hydrate. However, it is uncertain for methyl and ethyl alcohols whether they actually can form such hydrates even in the absence of a reference substance. These results strongly suggest that the size and/or shape limitation plays an important role in the formation of alcohol hydrates with a gas-hydrate structure, just as has been found for the formation of ether and ketone hydrates.

Rate of exchange of surfactant monomer radicals and long chain alcohols between micelles and aqueous solutions. A pulse radiolysis study

Pulse radiolysis has been used to measure the rate at which sodium lauryl sulphate monomer surfactant units enter into and exit from surfactant micelles. The free radical of the monomer is generated via OH attack following radiolysis and its reaction with ferricyanide noted. The rate constant for this reaction is 3.2 × 108 dm3 mol–1 s–1 at 25°C. In micellar solution two distinct rate processes are observed corresponding to the previous reaction, which is in competition with monomer radical entering the micelle. Radicals in the micelle react slowly with ferricyanide due to like charge repulsion of the micelle and this ion. The rate constants for exit, k–, and entry, k+, are k–= 1.8 × 105 s–1 and k+= 1.5 × 109 dm3 mol–1 s–1. These data agree well with those obtained by other methods. The site of OH attack on the lauryl chain is discussed. Similar studies of the interaction of pentyl alcohol and cyclohexanol with sodium lauryl sulphate micelles are reported and discussed in the context of micellar equilibria. The equilibrium constant for pentyl alcohol/micelle interaction is K/N= 15 dm3 mol–1 and for cyclohexanol/micelle, K/N= 25 dm3 mol–1.

Dielectric Relaxation and Molecular Structure. XIV. The Dielectric Behavior of Six Isomeric Pentyl Alcohols

Abstract The dielectric constants and losses of six isomeric pentyl alcohols have been measured in the frequency range of 1–0.35 GHz at 25 °C. The relaxation times of these alcohols decrease with an increase in the steric hindrance of the hydroxyl group.