Effect of Liquid-phase Oxidation Impurities on Sol

230火炸药学报Chinese Journal of Explosives & Propellants第41卷第3期 2 0 18年6月DOI:10.14077/j. issn.1007-7812.2018.03.003Effect of Liquid-phase Oxidation Impurities on Solubility of Water in Hydrocarbon FuelsA. A. Boriaev(Saint Petersburg StateUniversityofArchitecture and Civil Engineering , 4 VtorayaKrasnoarmeyskayaSaint Petersburg , 199005，Russia )Abstract ： The effect of liquid-phase oxidation impurities on the solubility of water in hydrocarbon fuels was studied.The results show that the concentration of polar surfactant molecules i n the first region increases (true soluduring fuel oxidation ，and since the oxidation groups ( — COOH ，一O =O ，一OH ，etc. ) have similar dipolemoment#，the dielectric loss tangent tan # increases linearly in this region withsurfactant concentration. Upon further oxi­dation ， micelle structures begin to form at a certain point. Micelle formation leadsto asharpdecrease inmoment attributable to t he monomer unit #/%，where % is the number of molecules in a micelle. A several-fold de­crease in the dipole moment leads to a sharp drop in tan #. Upon further increase in the number and size of micelles ， the dipole moment remains practically unchanged ， and the dielectric loss tangent begins to increase linearly again with surfactant concentration. If the critical concentration for micelle formation is achieved upon further oxidation of hydrocarbon liquids ，micelle formation processes occur spontaneously in the solution ，and the true solution becomes a colloidal system (so l ). The resultingmicelles arestructuredwithhydrocarbonradicals ofmoloutside and hydrophilic (polar ) groups toward the inside. Water molecules are located inside micelles and held so se­curely that water m olecules do not aggregate as temperature decreases. The reason for significant differences in the equilibrium solubility of water in hydrocarbon fuels is the different oxidation factors of product samfrom the accumulation of various concentrations of oxidation products ，which are natural surfactants ，in hydrocarbonfuels.Keywords ： water solubility ； hydrocarbon fuels;oxidation factor CLC number ：T J55；O65Document Code ： AArticle ID ：1007-7812(2018)03-0230-06Introduct#onAppearance of free water in a hydrocarbon fuel during operation affects many performance properties ： it reduces the corrosion resistance of structural materials ， increases static ， and promotes biochemical decomposition ， fuel oxidation ， re­lease of hydrogen (which is an explosion hazard) in tribo- chemical reactions ， etc. Emulsified water lowers an impor­tant performance characteristic—low-temperature pump abili­ty—due to the deposition of ice crystals on fuel system pipe­line filters at freezing temperatures.Dehydration is important for improving the quality of hy­drocarbon fuels ； this process requires modern ，high-perform­ance technologies [1"3]. Kobyzev S. V. [1] proposes an expand­ed multi-element mathematical model of hydrocarbon fuel de­hydration as a part of pre-launch preparation. The paper dis­closes the following models based on the proposed integrated mathematical model ： the modii of mass transfer into an isola­ted gas bubble，the m odii of mass transfer from the fuel liq­uid phase tothedisperse gasphasewi t h int h e prepara t i o n u­nit volume，the modii of mass transfer on the liquid surfacein thepreparationunit，and themodel ofmass transfer on theliquid surface accoun t i n g for surface bubbling.Aleksandrov A. A. et a l [2] consider characteristicsof hydrocarbon full dehydration processes based on fuel spar­ging and the cyclic technology of discharge and super satura­tion using dry nitrogen. The specific consumption of nitrogen and time for fuel dehydration operations was compared and gave recommendations on their application in full storage and preparation systems and at launch sites.Goncharov R. A. et a l [3] present results of theoretical studies of heat and mass transfer processes in devices for cool­ing and dehydration of hydrocarbon fuels at launch and tech­nical areas of launch sites.The causes of reduced low-temperature pump ability and emulsion water in full cannot be eliminated without knowing the natural laws and specifics of how water dissolves in hy­drocarbon fuels in the presence of oxidation products ， which generally have a complex chemical composition that partially changes during storage. Of great importance references [4"11] studied the oxidation mechanism，which leads to a wide varie­ty of chemical substances (oxidation products)，as well as the effect of the hydrocarbon fuel oxidation factor on water solu-Received date ：2017-12-10 ; Revised date ：2018-01-18Biography ： A. A. Boriaev( 1953一），male ，D r.，research field: energeticmaterials. E-mail: sasal953@yandex. ru第41卷第3期 A. A. Boriaev：Effect of Liquid-phase Oxidation Impurities on Solubility of Water in Hydrocarbon231bility，which ultimately leads to various concentrations of chemical compounds that are products of oxidation reactions.M aX. et a l [4] described the study of a novel oxidative desulfurization (ODS) method for liquid hydrocarbon fuels. The ODS method was applied to a model jet fuel and a real jet fuel ((P-8) in a batch system at ambient conditions. The re­markable advantagesofthenewODSmethod are that ODS can be performed in the presence of O2 at ambient conditions without using peroxides and aqueous solvent and thus without involving a biphasic oil-aqueous-solution system.Fernandez-Tarrazo E et al. [5] explored the applicability of one-step irreversible Arrhenius kinetics of first-order reac­tions to a numerical description of the combustion of partially premixed hydrocarbons. Computations of planar premixed flames were used to select three model parameters ： heat of reaction q ， activation temperature T a， and preexponential factor B.You X. et al. C 6] proposed a detailed kinetic modll for the combustion of normal alkanes up to n-dodecane above 850 K. The modil was validated against experimental data. Com­bined withthebaseC "—C4model，the simplified m odil pre­dicted fuel pyrolysis rate and product distribution ， laminar flame speeds，and ignition delays as closely as the detailed re­action model.Murugan P. et al. C 7] investigated low-temperature oxi­dation (LTO) of Fosterton crude oil mixed with its reservoir sand in a t ubular reactor. The general model for an nt h order reaction was used to obtain the kinetic parameters of the coke oxidation reaction. The activation energy ， frequency factor and order of the reactions were determined using the model.Al-Hamamre Z. et a l [8] stated that a very high temper­ature fue--air mixture was necessary for the thermal partial oxidation of hydrocarbon fuels in order to have a high reaction temperature ， which accelerated the reaction kinetics. For diesel fuel and due to the ignition delay time behavior ， var­ying oxidation behavior may occur at various preheating tem-peraNures.Li D. et a l [9] described enhanced autoxidation experi­ments of hydrocarbon fuels ， which were performed simulta­neously. The therma--oxidation stabilities for these fuels un­der various conditions were compared using ultraviolet-visible spectrometry and infrared spectra.Thomas S. et a l C 10] described pyrolysis and fuel-rich oxidation experiments in an isothermal laminar-flow reactor ， using the model fuel catechol (ortho-dihydroxybenzene )， a phenol-type compound representative of structural entities in coal ， wood and biomass ， to better understand the effects of oxygen on the formation and destruction of polycyclic aromat­ic hydrocarbons (PAH) during the burning of complex solid fuels. The PAH products ， ranging in size from two to nine fused aromatic rings，had been analyzed by gas chromatogra­phy with flame-ionization and mass spectrometric detection ， and by high-pressure liquid chromatography with diode-array ultraviolet-visible absorbance detection.Shakeri A. et al. C 11] presented a new approach to reduce large detailed or skeletal mechanisms of hydrocarbon fuel oxi­dation to a low-cost skeletal mechanism. The method in­volved an integrated procedure including a Sensitivity Analy­sis (SA) and a Gradual Evaluation of Ignition Error (GEIE).According to the literature review ， the composition ofhydrocarbon fuel oxidation products depends on oxidation re­action conditions ， and is characterized by various reaction mechanisms and the variety of generated chemical com­pounds including significant concentrations of oxidation products，which can be considered surfactants based on their structures.The authors found no published data on the effect of the hydrocarbon fuel oxidation factor and ， correspondingly ， the effect of impurities generated from the liquid-phase oxidation reaction on the solubility of water in hydrocarbon fuels. Asshown below，it is impossible to create an effective procedurefor dehydrating hydrocarbon fuels without assessing the im­pact of oxidation factor ， since during our experiments we found a significant difference in the nature of equilibrium wa­ter solubility curves for various batches of the same hydrocar­bon fuel.Studying the solubility of water in hydrocarbon fuels is associated with an important performance characteristic ： low- temperature pump ability ， which causes various emergencies due to fuel supply failure C 12].The conducted experiments determined the reasons for significant differences in the equilibrium solubility of water as a function of temperature for various batches of the same hy­drocarbon fuel. The main reason is the different oxidation factors of product samples ， resulting from the accumulation of oxidation products ， which are natural surfactants ， in hy­drocarbon fuels. Surfactants are organic substances contai­ning a hydrocarbon radical and one or several active polar groups. The surfactant hydrocarbon portion may consist of paraffinic ，isoparaffinic，naphthenic aromatic ， and other hy­drocarbons of various structure. For the most common active group/are oxygen-containing (ether carboxyl hydroxyl etc. ) and nitrogen-containing (nitro-，amino-，amido -， etc.)groups+1 Experimental-theoretical studiesIt is known that water dissolved in a hydrocarbon liquid follows Henry’s law like a dissolved gas:C=Clm •• % (1)•i S H $ Owhere !;h 2o is the partial pressure of water vapor in the space above the fuel surface ； !S h 2o is the saturated water va-232火炸药学报第41卷第3期〇1-------------■-------------■-------------■--------------223 243 263 283 303T/K(b)Fig. 1 Limit water solubility versus temperature for variousbatches of hydrocarbon fuelConsidering differences in storage conditions for study samples of hydrocarbon fuels from various batches, it was as­sumed that various oxidation factors of fuel samples may af­fect water solubility, despite the fact that analysis of the main parameters of oxidation factor using current standardized methods (presence of soluble gums, acidity—determination according to state standards (GOST) or technical specifica­tions for fuels) showed there are practically no liquid-phase oxidation products. We assumed that surfactants accumula­ting in the fuel during its oxidation play the determining role in changes of the equilibrium water solubility in hydrocarbon fuels.Thus, the foregoing defines the need to carry out a set of experiments to confirm this assumption.This paper presents the results of experimental studies of the oxidation factorZ effect and the effect of artificially intro­duced surfactants on water solubility in naphthene-base fuel.According to standards, oxidation parameters of naph­thene-base fuel (acidity and gums) must not exceed 0. 5 and 2. 0 mg per 100 mL, respectively. Experiments have shown that water solubility in hydrocarbon fuels can vary considera­bly (Figure 1). However, water solubility for products with zero parameters of acidity and gums varies over a wide range as well [1314] , which indicates insufficient sensitivity of the methods used to determine these parameters at low oxidation factors of hydrocarbon fuels [15"17].which corresponds to the standards for production, while ex­periments have shown that permissible variations of these pa­rameters in the standards could not have a significant effect on water solubility.por pressure ； % is t he relative humidity ； CI im is the limit or maximum possible value ofwater dissolution at a given tem-peraNure .The value of CI im = /( 3) is similar to the Henry’s law constant for gases, which is a physical constant for individual liquid/gas systems ，i . e . it is constant for hydrocarbon liquid/ water systems.The limit solubility CI im determines the equilibrium solu­bility of water in the fuel and is a function of temperature. As for most liquid/gas systems , water solubility decreases as temperature decrease and , in accordance with thermodynamic laws of supersaturated solutions , free water forms in the product mass in the form of micro-droplets , followed by crys­tallization at temperatures below freezing. Ice crystals block up filters in fuel lines and stop fuel supply. This，in its turn , leads to emergencies. It should be noted that the equilibrium temperature corresponding to Cfm is referred to as the “cloud point，, since , during experimental determination of the solu­bility curve (to perform analysis) , a slight decrease in tem-peraNure relaNive No Nhe equilibrium NemperaNure leads N o clouding of the product due to formation of a new , finely dis­persed phase (free water or ice). After experimental determi­nation of the function Ciim= f(T ') , it is easy to establish per­missible limits for the dissolved water content in hydrocarbon fuels that exclude the possibility of ice crystal formation at specified low-temperature operating conditions.In the course of our experiments to determine the equi­librium function C \iia = f {T ) for hydrocarbon fuels , we found a significant difference in the nature of equilibrium water sol­ubility curves for various batches of the same hydrocarbon fu­el. Figure 1 shows experimental curves for the naphthene- base hydrocarbon fuel (Figure 1(a)) and T-6 hydrocarbon fu­el (Figure 1(b )).The results made it more difficutt to determine reasona­ble limits for the permissible water concentration in hydrocar­bon fuels to prevent fuel system failure due to the formation of ice crystals when fuel temperature decreases. For exam­ple ,at a residual water concentration in fuel of Cw ==0. 001 _ , ice crystals may form on curve 1 is possible only at temperatures below 40 ' , on curves 2 and 3 — at tempera­tures below 14 ' , and on curve 4 — at temperatures below 6 ' (Figure 1(a )). The same tendency is also observed for T-6 hydrocarbon fuel (Figure 1(b )).This fundamental difference in results requires an expla­nation to prevent emergencies in equipment operation and use oVhydrocarbonVuels.We have previously ascertained that the hydrocarbon group composition has significant influence on water solubility in hydrocarbon fuels. The fractional composition of fuels and the content of mechanical impurities have a particular influ­ence as well. However , their influence has a definite valuer /K s%/o I X MU第41卷第3期 A. A. Boriaev：Effect of Liquid-phase Oxidation Impurities on Solubility of Water in Hydrocarbon233Experimental researchTo assess the effect of oxidation products on water solu­bility in hydrocarbon fuels, stripped, silica-gel-filtered naph­thene-base fuel was selected from a certain batch, and sam­ples with various oxidation factors were prepared under the same conditions (samples were prepared with air sparging through the product layer at100 ' %. After oxidation, va­rious physical and chemical parameters were determined for each fuel sample that reacted with a defined quantity of oxy-gen.Surface tension was determined in accordance withGOST R 50003-92 (ISO 304-85). Electrical and physical pa­rameters (dielectric permittivity and dielectric loss tangent) were measured using an AC bridge with an automatic balanc­er and a transducer (three-electrode, contact, temperature- controlled sensor) [18].The limit water solubility within the temperature range of 20 ' to —40 ' was determined by creating 100% humid­ity in the volume above the fuel layer while stirring. The limit fuel dryness was determined as the amount of water remai­ning in the fuel after drying under vacuum for 1 hour. The content of soluble gums was determined in accordance with GOST 32404-2013, and acidity was determined according to ISO 3012-74. The content of water dissolved in the fuel was determined according to GOST 2477-2014. The total amount of reacted oxygen was determined with a LCMS-IT-TOF hy­brid liquid chromatograph/mass spectrometer. All measure­ments were carried out at t = 20The resulting experimen­tal data are shown in Figure 2. In which,e is dielectric per­mittivity ； &w f is surface tension at the water/fuel interface; &a f is surface tension at the air/fuel interface ； tand is dielec­tric loss tangent ； C—3 is limit water solubility at —30 '; C L M is limit dryness; C g is content of soluble gums; A is acid­ly.Fig 2. Changes in physical and chemical parameters of thehydrocarbon fuel depending on its oxidation factor(the total quantity of reacted oxygen)The data presented in Fi g ure 2 show that an increase in fuel oxidation factor leads to changes in all parameters except surface tension at the product/air interface. The horizontalaxis, showing the total quantity of reacted oxygen, can be di­vided into three characteristic regions ： the first region is the interval of 0 — 55cm3/L，the second region is the interval of 55 — 88cm3/L and the third region is the interval of 88 — 165 cm3/L. Gums and acidity (GOST parameters for fuel) begin to grow only in the third region, not reacting to oxida­tion prior tothat.Inthe first region, thesurfacethe product/air interface and the dielectric loss tangent tan § change most significantly. Their change indicates the appear­ance of oxygen compounds in the fuel. A sharp decrease in surface tension & is evidence that these compounds are surfac­tants. Baseduponthenatureofchanges ininflections in the second region) , surfactants are in the mo­lecular ,unassociated state (true surfactant solution in the hy­drocarbon liquid up to an oxidation factor of 55 cm3/L).Upon further oxidation in the second region, the surfac­tant concentration reaches critical micelle concentration (CMC) , and the full can be considered a colloidal surfactant solution in the hydrocarbon liquid with all properties inherent to them, in particular the capacity for solubilization, i. e. for increase in solubility of any substance due to its introduction into micelles. In this case, the solubilization of water mole­cules into surfactant micelles is observed.This is confirmed by a sharp increase in the limit dryness C(IM after CMC (the second region). As surfactant concentra­tion increases after CMC, even more water remains in the fu­el. It is not removed by vacuum drying, which is evidence that it is solubilized by micelles.Changes in electrical and physical parameters are notable as well. The tan^ increases more than three-fold upon increase in the oxidation factor in the first region. The value then drops sharply back to baseline and then increases slowly.According to the Debye theory, there is a relationship between tan # and the concentration of polarmolecules (here, oxy groups )：t a n #=4(7. /e+2、"27)T (,，5%(2 )1+«2 •where ( is theBoltzmann constant ; e is dielectric permi-- tivity ； % is angular frequency of measurement, and & is relax-NionNime.The mult.pl.er 4(7.is constant at constant tempera-27(3ture. The c hange in the dielectric permittivity e does not sig­nificantly affect tan# and, therefore, the second multiplier is also constant. The same is the case for the third multiplier if measurements are carried out at a constant angular frequency and the position of the dispersion area (accounted for by the value &=----) remains unchanged.%a n gTherefore ：tan#= 4'2C3)m 1c I s o s .b o s )/(V /J)234火炸药学报第41卷第3期where B is a constant multiplier.Thus, the concentration of polar surfactant molecules in the first region increases (true solution) during fuel oxida­tion, and since the oxidation groups (— COOH,—〇=0,—OH, etc. ) have similar dipole moment tan 8 increases lin­early in this region with surfactant concentration. Upon fur­ther oxidation, micelle structures begin to form at a certain point. Micelle formation leads to a sharp decrease in the di­pole moment attributable to the monomer unit ji/n,where is the number of molecules in a micelle. A several-fold de­crease in the dipole moment leads to a sharp drop in tan#. Upon further increase in the number and size of micelles, the dipole moment remains practically unchanged, and the dielec­tric loss tangent begins to increase linearly again with surfac­tant concentration.The deviation of the dielectric permittivity diagram from linearity is also explained by the decrease in dipole moment per surfactant molecule '/n.Figures 3 and 4 present the infrared spectra of hydrocar­bon fuel samples observed using a UV-1800 spectrometer.5-M=0. 8；6-M=10(M is a dimensionless coefficient)Fig. 3 IR spectra of naphthene-base fuel samples“limit dryness” for naphthene-base fuelWater dissolved in non-polar solvents has an asymmetri­cal oscillation frequency of y= 3 705 cm 1and a symmetrical oscillation frequency of y = 3 614 cm 1. Infrared spectra were determined for fuel samples with equilibrium solubility o f0. 000 6 — 0. 001 5 _ (mass fraction) , and the spectral bands cor­responding to these oscillations are almost negligible (absorp­tion increases somewhat at y = 3 630 cm 1 ). The most pro­nounced absorption band in the spectrum is at y=3 550 cm 1 ,increasing with fuel oxidation factor and 4<limit dryness”.Experimental data support the conclusion that the ab­sorption band at y= 3 550 cm 1corresponds to bound water molecules in non-polar organic solvents.The absorption band in the IR spectrum at y=3 550 cm 1 corresponding to water molecules bound to each other, and the relationship between its intensity and 4<limit dryness” con­firms micelle formation concentration upon fuel oxidation. Most likely, this band corresponds to the bound (solubilized) water located inside inverse surfactant micelles-products of liquid-phase oxidation.Apparently, the initial product contains a certain amount of neutral resins—substances of liquid or semi-liquid consis­tency with very weak surfactant properties. They have heter­ogeneous composition and are a mixture of various aromatic hydrocarbons with long chains$condensed aromatic and naphthenic aromatic compounds with short chains, phenolic and nitrogen bases , and other compounds.Neutral resins readily enter into oxidation , bodying and condensation reactions , reacting to form asphaltenes , carbe- nes , and carboids. Asphaltenes are quite strong surfactants at the hydrocarbon/ water interface. Due to their surfactant properties , resinous asphaltenes play an important role in the production , transport , and refining of oil , increasing its we-- tability. Naphthenic (carboxylic) acids , which are wide­spread oil-soluble surfactants , are also oxidation products. Colloidal surfactants are of particular interest. The main dis­tinctive feature of these substances is their ability to form thermodynamically stable heterogeneous disperse systems (associative ormicellar colloids). The main characteristics of colloidal surfactants are high surface activity , capacity for spontaneous micelle formation , and capacity of surfactant so­lutions to solubilize , i e. to increase the solubility of a sub­stance because its molecules penetrate into micelles.3 ConclusionsThus , we can conclude that if CMC is achieved upon fur­ther oxidation of hydrocarbon liquids , micelle formation processes occur spontaneously in the solution , and the true solution becomes a colloidal system (sol). The resulting m- celles are structured with hydrocarbon radicals of molecules toward the outside and hydrophilic (polar) groups toward the inside. Water molecules are located inside micelles and held so securely that water molecules do not aggregate as tempera­ture decreases. These processes explain the experimental data we obtained showing significant differences in the equilibrium solubility of water as a function of temperature for various batches of the same hydrocarbon fuiLThe conducted experiments determined the reasons for significant differences in the equilibrium solubility of water as a function of temperature for various batches of thesame hy­第41卷第3期 A. A. Boriaev：Effect of Liquid-phase Oxidation Impurities on Solubility of Water in Hydrocarbon235drocarbon fuel. The main reason is the different oxidation factors of product samples, resulting from the accumulation of oxidation products, which are natural surfactants, in hy­drocarbon fuels. Surfactants are organic substances contai­ning a hydrocarbon radical and one or several active polar groups. The surfactant hydrocarbon portion may consist of paraffinic , isoparaffinic , naphthenic aromatic , and other hy­drocarbons of various structure. For the most common active groups are oxygen-containing (eth er，carboxyl , hydroxyl , etc. %and nitrogen-containing (nitro-，amino-，amido-，etc. % groups. Thus，dehydration is important for improving the quality of hydrocarbon fuels; this process requires modern，high-performance technologies based on well-understood nat­ural laws and specific mechanisms of how water dissolves in hydrocarbon fuels，one of which is the effect of liquid-phase oxidation impurities on water solubility.References![1] Kobyzev S V. Modelirovanie obezvozhivanija uglevodorod-nogo gorjuchego s primeneniem azota pri vypolnenii tehno-logicheskih operaci- podgotovki raketnogo topliva na starto-vom kom plekse)]. 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