Hydrocarbon Fuel Analysis by Gas Chromatography and Mass Spectrometer with Hexane Solvent

Transcription

1 International Journal of Engineering & Technology IJET-IJENS Vol:13 No:02 23 Hydrocarbon Fuel Analysis by Gas Chromatography and Mass Spectrometer with Hexane Solvent Moinuddin Sarker*, Mohammad Mamunor Rashid Natural State Research Inc, Department of Research and Development, 37 Brown House Road (2 nd Floor), Stamford, CT-06902, USA, Phone: (203) , Fax: (203) * Abstract-- Waste plastic (HDPE) to fuel production and product fuel was analysis with hexane solvent by using Gas Chromatography and Mass Spectrometer (GC/MS). Liquid fuel sample was mixture with hexane solvent in ratio fuel 1 ml: solvent 5 ml on the other hand fuel 5 ml: solvent 1 ml. Two types of liquid sample was analysis by GC/MS one was liquid fuel 1 ml and hexane solvent was 5 ml, 2 nd sample was liquid fuel 5 ml and hexane solvent was 1 ml. GC/MS analysis chromatogram result showed 1 ml fuel and 5 ml hexane solvent mixture to carbon compounds range C 6 to C 27, on the other hand 5 ml fuel and 1 ml hexane solvent mixture to carbon compounds chain range showed C 6 to C 24. Index Term-- chromatography, mass spectrometer fuel, hydrocarbon, hexane solvent, gas I. INTRODUCTION Plastics are being produced and utilized worldwide at an increasing rate with each subsequent year.[1] Plastics are produced from petroleum and are composed primarily of hydrocarbons but also contain antioxidants and colorants.[2] Plastics once used are not effectively recycled[3] and are difficult to collect from the consumer and then to separate into specific types.[4] Postconsumer plastics are disposed of by landfilling, thereby removing a potential hydrocarbon fuel or chemical feedstock source from the market. Tertiary recycling of the waste plastics produces fuels and chemical feedstocks from mixed waste plastics and offers an alternative to primary recycling where the plastics must be carefully separated in order to recover the monomer.[5,6] Currently, around 20% of the volume and 8% of the weight of all municipal solid waste in the U.S. is made up of waste plastics.[7] Of the approximately 80 billion pounds of plastics currently produced in the United States, most eventually ends up in landfills, with only 2-3% being recycled.[8] In contrast to paper and garbage wastes, most plastics are not readily biodegradable and will remain in the landfill for indeterminate periods. The ever increasing costs of landfill disposal coupled with a significant public resistance to the creation of new waste landfills has led to increased efforts toward finding economically feasible and environmentally acceptable means of recycling these materials. Most polymers, however, will give a mixture of products that must undergo extensive separation to recover a monomer stream, and the depolymerization of postconsumer commingled (mixed) waste plastics to pure monomers does not appear feasible. Thus, other processes for dealing with commingled waste plastics have been proposed including pyrolysis,[9-14] gasification,[15] and catalytic coliquifaction.[16] In a pyrolysis type process, such as the Conrad process,[11,12] shredded mixed plastics are heated in the absence of oxygen and depolymerized back into liquids (70-80%) and gases (5-10%). The gases are burned in the process to provide heat needed for the depolymerization and pyrolysis. Although the pyrolysis process produces substantial quantities of light naphtha range (-205 C) liquids, significant quantities of heavier gas oil range liquids are also produced. The heavier gas oil fraction is potentially valuable as upgrading feedstock for naphtha range material with an end use in the transportation fuel pool[17]. The coprocessing of other hydrocarbon resources such as our most abundant U.S. hydrocarbon resource, coal, to the tertiary recycling of plastics will provide an additional source of hydrocarbon fuels and chemical feedstocks.[18] Typical household plastic waste consists of 63% high- and low-density polyethylene (HDPE, LDPE), 11% polypropylene (PP), 11% polystyrene (PS), 7% polyethylene terephthalate (PET), and 5% polyvinyl chloride (PVC),[19] causing these wastes to be highly aliphatic. By contrast, coal is highly aromatic. These differences in their chemistry cause the two materials to be incompatible during simultaneous coprocessing. The conditions and catalysts that

2 Intensity [a. u.] International Journal of Engineering & Technology IJET-IJENS Vol:13 No:02 24 are optimal for liquefying coal and for converting waste plastics are different,[20,21] requiring some additional component or components in the reaction to improve the compatibility. The desire to produce highly isomerized alkanes for highoctane transportation fuels has led to the use of bifunctional catalysts containing dispersed transition metals on acidic supports for alkane hydrocracking.[22] Bifunctional catalysts consisting of hydrogenation components such as sulfided Ni, Mo, or W promoted on acidic supports such as Al 2 O 3 or SiO 2 - Al 2 O 3 have been used; they crack n-alkanes to a significant extent but result in little isomerization.[23-25] Noble metals, such as Pt and Pd, are strong hydrogenation catalysts which balance the acidity of supports and were reported [26, 27] to result in high selectivities to isomerized products in alkane hydrocracking.[28] Strong solid acid catalysts have high activity in cracking and skeletal isomerization of n- alkanes[29-31] and could serve as effective hydrocracking catalysts, especially when promoted by strong hydrogenation metals such as Pt and Ni. The thermal degradation of LDPE has been widely studied.[32-36] Among the volatile products obtained in the pyrolysis of this polymer, C 3 -C 5 olefins are the most valuable products since they are the basic building blocks for the manufacturing of petrochemical products, and their demand is steadily increasing. [37] Furthermore, light olefins such as ethylene and propylene are raw materials for the production of polymers and alkylbenzenes. [38, 39] Other valuable products present in the volatile compounds generated during LDPE pyrolysis are propane and butane, which are very useful products that constitute a nonrenewable source of energy. On the other hand, the condensable products generated contain valuable gasoline-range hydrocarbons. [40] All these compounds have interesting industrial applications. These valuable compounds can be compared with those obtained in the thermal cracking of petroleum.[41] In this process, lowvalue heavy oils are converted into more valuable products like gasoline, light cycle oil, and lighter products.[41-45] II. METHOD DESCRIPTION HDPE waste plastic to fuel production process was described [46]. Whole process description in the journal of Abundant High-Density Polyethylene (HDPE-2) Turns into Fuel by Using of HZSM-5 Catalyst, Journal of Fundamentals of Renewable Energy and Applications, Vol. 1 (2011), Article ID R110201, 12 pages, doi: /jfrea/r III. LIQUID FUEL ANALYSIS WITH HEXANE Retention Time [M] Fig. 1. GC/MS chromatogram of HDPE to fuel 1 ml and hexane solvent 5 ml mixture

3 International Journal of Engineering & Technology IJET-IJENS Vol:13 No:02 25 Number of Peak T ABLE I GC/MS CHROMATOGRAM COMPOUNDS LIST OF HDPE TO FUEL 1 ML AND SOLVENT 5 ML MIXTURE Retention Time (min.) Trace Mass (m/z) Compound Name Compound Formula Molecular Weight Probability % NIST Library Number Ethylidenecyclobutane C6H Heptene C7H Heptane C7H Heptene C7H Cyclopropane, C7H trimethylmethylene Cyclopentane, 1-methyl-2- C7H methylene Cyclohexane, methyl- C7H Cyclopentane, ethyl- C7H ,4-Heptadiene C7H Cyclobutane, (1- C7H methylethylidene) Cyclopentane, ethylidene- C7H Cyclobutene, 2- C7H propenylidene Cyclohexene, 1-methyl- C7H Oxabicyclo[4.3.0]non-8- C8H10O en-2-one, cis Octene C8H Octane C8H Octene C8H Octyn-1-ol C8H14O ,3- C8H14N Diazabicyclo[2.2.1]hept-2- ene, 7-isopropyl Bicyclo[4.1.0]heptane, 3- C8H methyl Methylcycloheptene C8H Cyclohexane, ethyl- C8H Cyclopentane, (1- C8H methylethylidene) Spiro[2.5]octane C8H ,4-Dimethyl-cyclohex-2- C8H14O en-1-ol Nonene C9H Nonane C9H cis-4-nonene C9H Cyclohexane, propyl- C9H Cyclodecane C10H Decene C10H Decane C10H Cyclodecane C10H Butyl-1-decene C14H Undecene C11H Undecane C11H

4 International Journal of Engineering & Technology IJET-IJENS Vol:13 No: Undecene, (Z)- C11H Dodecene C12H Dodecane C12H Dodecene, (E)- C12H Z-10-Pentadecen-1-ol C15H30O Tridecene C13H Tridecane C13H Tridecene C13H (R)-(-)-(Z)-14-Methyl-8- C17H34O hexadecen-1-ol Tetradecene, (E)- C14H Tetradecane C14H Tetradecene C14H Tridecen-1-ol C13H26O Pentadecene C15H Pentadecane C15H Pentadecene C15H Hexadecanol C16H34O Hexadecane C16H Hexadecene, (Z)- C16H Nonadecene C19H Hexadecanol C16H34O Heptadecane C17H E-15-Heptadecenal C17H32O Nonadecane C19H E-7-Octadecene C18H Nonadecene C19H Nonadecane C19H Nonadecene C19H Eicosane C20H Nonadecene C19H Heneicosane C21H Heneicosane C21H Tetracosane C24H Nonadecane C19H Heptacosane C27H Heptadecane, 2,6,10,15- C21H tetramethyl- Liquid sample was analysis by Perkin Elmer (Clarus 500) GC/MS with auto sampler equipment. Column was use Perkin Elmer Elite-5MS, 30 meter length, 0.25 mmid, 0.5um df, maximum column program temperature 350 ºC and minimum bleed temperature at 330 ºC. Catalog number is N and serial number GC Carrier gas was helium. GC operating temperature was 300 ºC and MS program was setup MS scan Ion Mode EI+, data format centroid, mass scan start 35 to 528. Scan time 0.25 (sec) and inter scan time 0.15 (sec). HDPE waste plastic to fuel product was mixture with hexane solvent for run into GC/MS. Liquid fuel was only 1 ml and hexane solvent was 5 ml, both liquid mixed and keep for while then placed into GC auto sampler system. Hexane solvent collected from VWR. Com Company. GC/MS fuel chromatogram analysis (figure 1 and table 1) compounds was traced base one retention time (m), trace mass (m/z), compound formula, molecular weight, probability percentage and NIST library number. Liquid analysis compounds table showed liquid product has aliphatic compounds such as alkane, alkene and alkyl compounds. Some alcoholic

5 Intensity [a. u.] International Journal of Engineering & Technology IJET-IJENS Vol:13 No:02 27 compounds, nitrogen content compound, and oxygen content compounds also detected from GC/MS chromatogram. 1ml fuel and 5ml hexane mixture solvent mixture fuel to GC/MS starting compounds is appeared Ethylidenecyclobutane (C6H10) (t=2.61, m/z=67) compounds probability percentage is 20.0%. All compounds detected from small carbon number to large carbon number accordingly from GC/MS chromatogram. GC/MS chromatogram compounds appeared based on compounds boiling point small number to large number and low temperature to higher temperature. Heptacosane (C27H56) (t= 26.25, m/z=55) is large carbon number compound detected from GC/MS Chromatogram. Most of the long chain hydrocarbon compounds found this fuel because high density polyethylene has long chain only carbon and hydrogen combination. HDPE chemical structure is ( H2C-CH2-) n. Product fuel has some alcoholic group compounds such as 2-Octyn-1-ol (C8H14O) (t=4.56, m/z=55), 4, 4-Dimethyl-cyclohex-2-en-1-ol (C8H14O) (t=5.87, m/z=56), Z-10-Pentadecen-1-ol (C15H30O) (t=12.41, m/z=55), (R)-(-)-(Z)-14-Methyl-8-hexadecen-1-ol (C17H34O) (t=13.81, m/z=55) and so on. Nitrogen and oxygen content compounds are 2,3-Diazabicyclo[2.2.1]hept-2-ene,7- isopropyl-(c8h14n2)(t=4.65, m/z=55) and cis-3- Oxabicyclo[4.3.0]non-8-en-2-one, (C8H10O2) (t=4.01, m/z=79). Single bond compounds and double bonds compounds are present in this fuel. Some compounds are described in this analysis section from compounds table such as 1-Heptene (C7H14) (t=2.71, m/z=56) compound molecular weight 98 and probability percentage is 38.1%, Heptane (C7H16) (t=2.81, m/z=43) compound molecular weight 100 and probability percentage is 72.0%, 1-methyl-2-methylene- Cyclopentane (C7H12) (t=3.09, m/z=81) compound molecular weight 96 and probability percentage is 15.6%, (1- methylethylidene)-cyclobutane (C7H12) (t=3.54, m/z=81) compound molecular weight 96 and probability percentage is 16.4%, 1-Octene (C8H16) (t=4.17, m/z=55) compound molecular weight 112 and probability percentage is 26.3%, ethyl-cyclohexane (C8H16) (t=4.95, m/z=83) compound molecular weight 112 and probability percentage is 49.1%, 1-Nonene (C9H18) (t=5.97, m/z=56) compound molecular weight 126 and probability percentage is 15.1%, propyl- Cyclohexane (C9H18) (t=6.71, m/z=55) compound molecular weight 126 and probability percentage is 39.3%, 2-Butyl-1- decene (C14H28) (t=9.35, m/z=56) compound molecular weight 196 and probability percentage is 6.50%, (Z)-4- Undecene (C11H22) (t=9.67, m/z=55) compound molecular weight 154 and probability percentage is 8.13%, and so on. 1 ml fuel and 5 ml hexane solvent mixture is change fuel density and fuel look like is thin. High percentage of hexane solvent mixture can change fuel inside compounds structure Retention time [M] Fig. 2. GC/MS chromatogram of HDPE to fuel 5 ml and solvent 1 ml mixture

6 International Journal of Engineering & Technology IJET-IJENS Vol:13 No:02 28 Number of Peak Retention Time (min.) T ABLE II GC/MS CHROMATOGRAM COMPOUND LIST OF HDPE TO FUEL 5 ML AND SOLVENT 1 ML MIXTURE Trace Mass (m/z) Compound Name Compound Formula Molecular Weight Probability % NIST Library Number Cyclopentane, methylene- C6H Heptene C7H Heptane C7H Heptene C7H Cyclopentene, 4,4- C7H dimethyl Cyclopentane, 1-methyl-2- C7H methylene Cyclohexane, methyl- C7H Cyclopentane, ethyl- C7H ,3-Pentadiene, 2,3- C7H dimethyl Cyclohexene, 4-methyl- C7H ,4-Heptadien-1-ol, (E,E)- C7H12O Cyclobutane, (1- C7H methylethylidene) Ethylcyclopentene C7H ,3,5-Cycloheptatriene C7H Cyclohexene, 1-methyl- C7H ,3-Cycloheptadiene C7H Octene C8H Octane C8H Octene, (E)- C8H Cyclopropane, (2,2- C8H dimethylpropylidene) Cyclopentane, (1- C8H methylethylidene) Methyl-2- C8H methylenecyclohexane Cyclopentane, propyl- C8H Cyclohexane, ethyl- C8H Cyclopentene, 1-propyl- C8H Cyclohexene, 1-ethyl- C8H ,4-Dimethyl-cyclohex-2- C8H14O en-1-ol Bicyclo[2.1.1]hexan-2-ol, C8H12O ethenyl Cyclohexanol, 2,4- C8H16O dimethyl Methyl-2- C8H methylenecyclohexane Cyclohexanemethanol, 4- C8H14O methylene ,5-Nonadiene C9H ,8-Nonadiene C9H Cyclohexanone, 4-ethyl- C8H14O

7 International Journal of Engineering & Technology IJET-IJENS Vol:13 No: Nonene C9H Nonane C9H cis-2-nonene C9H Cyclohexane, 1-ethyl-4- C9H methyl-, cis ,4-Octadiene, 7-methyl- C9H Cyclohexane, propyl- C9H Cyclopentene, 1-butyl- C9H Cyclononen-1-ol C9H16O Cyclohexene,3-propyl- C9H Cyclopentanol, 1-(1- C9H14O methylene-2-propenyl) Heptane, 5-ethyl-2,2,3- C12H trimethyl cis-3-decene C10H Decene C10H Decane C10H Cyclopentane, 1-methyl-3- C10H (2-methylpropyl) Cyclohexane, butyl- C10H ,5,7-Octatrien-3-o l, 2,6- C10H16O dimethyl Undecene, (Z)- C11H Cyclopropane, 1-heptyl-2- C11H methyl Undecane C11H Undecene, (E)- C11H Undecene, (Z)- C11H Carane, 4,5-epoxy-, trans C10H16O ,11-Dodecadiene C12H Dodecene C12H Dodecene, (Z)- C12H Dodecane C12H Dodecene, (E)- C12H Dodecene, (Z)- C12H Tridecene C13H Tridecane C13H Tridecene, (E)- C13H Tridecene, (Z)- C13H Heptylcyclohexane C13H Dodeca-1,6-dien-12-ol, C14H26O ,10-dimethyl Hexadecyne C16H Tridecene C13H Tetradecane C14H Tetradecene, (E)- C14H Tetradecene, (E)- C14H Cyclotetradecane C14H Hexadecanol C16H34O

8 International Journal of Engineering & Technology IJET-IJENS Vol:13 No: Z-10-Pentadecen-1-ol C15H30O Pentadecene C15H Pentadecane C15H E-2-Hexadecacen-1-ol C16H32O E-2-Octadecadecen-1-ol C18H36O Hexadecene C16H Hexadecane C16H Hexadecene C16H E-14-Hexadecenal C16H30O Heptadecane C17H Heptadecene, (Z)- C17H E-15-Heptadecenal C17H32O Octadecane C18H E-7-Octadecene C18H E-2-Octadecadecen-1-ol C18H36O Nonadecene C19H Nonadecane C19H Nonadecene C19H Nonadecene C19H Eicosane C20H Eicosene C20H Heneicosene (c,t) C21H Heneicosane C21H Docosene C22H Heneicosane C21H Docosene C22H Heneicosane C21H Tetracosane C24H Heneicosane C21H ml hexane solvent and 5 ml fuel product mixture also analysis by GC/MS and method and column was same as figure 1. Less percentage of fuel product and high percentage of hexane solvent mixture chromatogram and compounds data table showed figure 2 and table 2. Five (5) ml fuel and 1 ml hexane mixture after run into GC/MS and chromatogram analysis was performing according to NIST library compound number wise. Compounds was traced same as table 1 procedure. 1 ml hexane and 5 ml fuel mixture GC/MS traced compounds quantity are bigger than 1ml fuel and 5 ml hexane mixture GC/MS chromatogram compounds. 1 ml hexane solvent and 5 ml fuel mixture to compounds was determined based on trace mass (m/z), retention time (m), molecular weight, probability percentage and NIST library number wise. Analysis data table 2 showed product fuel has aliphatic group compounds such as alkane, alkene, and alkyl group compounds. Alcoholic and oxygen content compounds also appeared in this fuel because production was not vacuumed system. When HDPE waste plastic to fuel production process was performing it was open system process, it means that production process was in presence of oxygen. GC/MS chromatogram analysis result showed 1 ml hexane and 5 ml fuel mixture has carbon chain C 6 to C 24. Starting compound is methylene-cyclopentane (C6H10) (t=2.60, m/z=67) compound molecular weight 82 and probability percentage is 15.8%, and large number hydrocarbon compound is Tetracosane (C24H50) (t=24.97, m/z=57) compound molecular weight 338 and probability percentage is 14.7%. In this section some compounds are different from 1ml fuel and 5 ml hexane mixture to compounds. Both GC/MS analysis main object was to check what types compounds appeared less percentage solvent mixture and high percentage solvent mixture. All compounds are traced based on trace mass and retention time, retention time is increasing and compounds are appeared small to bigger. Low boiling point to higher boiling point compounds are such as Heptane (C7H16) (t=2.83, m/z=43) compound molecular weight 100 and probability percentage is 74.4%, 1-methyl-2-methylene- Cyclopentane

9 International Journal of Engineering & Technology IJET-IJENS Vol:13 No:02 31 (C7H12) (t=3.09, m/z=81) compound molecular weight 96 and probability percentage is 17.7%, 4-methyl- Cyclohexene (C7H12) (t=3.42, m/z=81) compound molecular weight 96 and probability percentage is 11.0%, Octane (C8H18) (t=4.36, m/z=43) compound molecular weight 114 and probability percentage is 46.6%, propyl-cyclopentane (C8H16) (t=4.91, m/z=55) compound molecular weight 112 and probability percentage is 13.8%, 2,4-dimethyl-Cyclohexanol (C8H16O) (t=5.50, m/z=43) compound molecular weight 128 and probability percentage is 6.50%, 4-ethyl-Cyclohexanone (C8H14O) (t=5.89, m/z=56) compound molecular weight 126 and probability percentage is 5.91%, Nonane (C9H20) (t=6.19, m/z=43) compound molecular weight 128 and probability percentage is 25.9%, 7-methyl-3,4-Octadiene (C9H16) (t=6.46, m/z=67) compound molecular weight 124 and probability percentage is 7.11%, 4-Cyclononen-1-ol (C9H16O) (t=7.09, m/z=57) compound molecular weight 140 and probability percentage is 7.13%, Decane (C10H22) (t=7.99, m/z=57) compound molecular weight 142 and probability percentage is 42.3%, 2,6-dimethyl-1,5,7-Octatrien- 3-ol (C10H16O) (t=8.81, m/z=105) compound molecular weight 152 and probability percentage is 6.64%, Undecane (C11H24) (t=9.68, m/z=57) compound molecular weight 156 and probability percentage is 32.5%, Dodecane (C12H26) (t=11.25, m/z=57) compound molecular weight 170 and probability percentage is 37.6%, Tridecane (C13H28) (t=12.73, m/z=57) compound molecular weight 184 and probability percentage is 43.7%, 6,10-dimethyl-Dodeca-1,6- dien-12-ol (C14H26O) (t=13.41, m/z=67) compound molecular weight 210 and probability percentage is 3.66%, Tetradecane (C14H30) (t=14.11, m/z=57) compound molecular weight 198 and probability percentage is 37.0%, Pentadecane (C15H32) (t=15.42, m/z=57) compound molecular weight 212 and probability percentage is 37.7%, Hexadecane (C16H34) (t=16.66, m/z=57) compound molecular weight 226 and probability percentage is 36.4%, Heptadecane (C17H36) (t=17.83, m/z=57) compound molecular weight 240 and probability percentage is 38.6%, Octadecane (C18H38) (t=18.95, m/z=57) compound molecular weight 254 and probability percentage is 18.0%, Nonadecane (C19H40) (t=20.00, m/z=57) compound molecular weight 268 and probability percentage is 22.3%, Eicosane (C20H42) (t=21.02, m/z=57) compound molecular weight 282 and probability percentage is 16.6%, and Tetracosane (C24H50) (t=24.97, m/z=57) compound molecular weight 338 and probability percentage is 14.7%. IV. CONCLUSION HDPE waste plastic to fuel product was analysis by using GC/MS with hexane solvent. The fuel and solvent mixture analysis main goal was extra chemical adding with product fuel and compounds structure change determination inside the fuel at less hexane solvent and high hexane solvent percentage. High percentage hexane solvent mixture fuel was thin and compounds structure change, on the other hand less percentage hexane solvent mixture with fuel thickness was not change and compounds structure was not substantial change. 1 ml fuel and 5 ml hexane solvent mixture to fuel analysis compounds data table showed compounds percentage is less than 5 ml fuel and 1 ml hexane mixture compounds data table compare. 1 ml fuel and 5 ml hexane solvent mixture fuel GC/MS analysis compounds table showed hydrocarbon chain length C 6 to C 27. Same way 5 ml fuel and 1 ml hexane solvent mixture fuel GC/MS chromatogram compounds hydrocarbon chain length C 6 to C 24. High percentage solvent adding to fuel can change main compounds structure and it make also thin. ACKNOWLEDGEMENT The authors acknowledge the support (financial) of Dr. Karin Kaufman, the founder and sole owner of Natural State Research, Inc. The authors also acknowledge the valuable contributions NSR laboratory team members during the preparation of this manuscript. REFERENCES [1] Resin Report. Mod. Plastics 1996, January, 70. [2] Leidner, J. Plastics Waste; Marcel Dekker: New York, [3] Porter, J. W. National Recycling Goal Met, But... Chemunique 1996, April. [4] Huffman, G. P.; Anderson, L.; Shah, N. Report on a Trip to Ascertain the Status of Feedstock Recycling of Waste Plastics in Europe. Consortium for Fossil Fuel Liquefaction Science, October, 16, [5] Leaversuch, R. D. Chemical Recycling Brings Real Vesatility to Solid-Waste Management. Mod. Plastics 1991, July, 40. [6] Miller, A. Back to Basics. Chem. Ind. 1994, 8 (2), 1. [7] Reisch, Marc S. Chem. Eng. News 1995, May 22, 30. 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