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Author:Myöhänen, Mari
Title:Asfalteenimalliaineiden synteesi
Synthesis of asphaltene model compounds
Publication type:Master's thesis
Publication year:2014
Pages:viii + 75 s. + liitt. 9      Language:   fin
Department/School:Kemian laitos
Main subject:Kemia   (KE3001)
Supervisor:Koskinen, Ari
Instructor:Karvinen, Esko ; Karppanen, Essi
Electronic version URL: http://urn.fi/URN:NBN:fi:aalto-201408292530
OEVS:
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Location:P1 Ark Aalto  1657   | Archive
Keywords:asphaltene
hydrocracking
SARA
saturated hydrocarbons
resins
aromatic compounds
hexabenzocoronene
ovalene
asfalteenit
vetykrakkaus
SARA-analyysi
tyydyttyneet hiilivedyt
hartsit
aromaattiset yhdisteet
heksabentsokoroneeni
ovaleeni
Abstract (eng):The aim of this study was to synthesize asphaltene model compounds.
Asphaltenes are the heaviest fraction of crude oil, and they are defined as the fraction that is insoluble in n-heptane but soluble in toluene.
In oil refining, asphaltenes cause fouling of process equipment and deactivation of the hydrocracking catalyst.
In order to minimize these factors, the kinetics of pure asphaltene compounds needs to be examined.
Asphaltenes cannot be characterized by any single molecular structure.
Instead, various model compounds have been employed to mimic the structure and properties of asphaltenes.
The most commonly used model compounds are pyrene or polyaromatic derivatives.
At present, asphaltenes are thought to consist of an alkyl substituted polyaromatic core, which often also contains substitutional hetero atoms, such as sulfur.
The molecular weight of asphaltenes varies between 500-1000 g/mol and, on average, the polyaromatic core is comprised of seven fused rings.
The literature part of this thesis reviews both refining and composition of heavy oil fractions and the synthesis of large aromatic compounds.
In the experimental part, a large aromatic compound 4,6,9,12,15,17-hexa-tert-butyl-tetrabenzo[bc,ef,hi,uv]ovalene was synthesized according to the previous work of Müllen and coworkers.
In the synthesis, pyrene was alkylated with a Lewis-acid and was subsequently oxidized with sodium periodate and ruthenium chloride.
The formed 2,7-di-tert-butylpyrene-4,5-dienone was exposed to Knoevenagel-reaction with diarylacetone, after which Diels-Alder-reaction with diphenylacetylene produced polyphenylene.
The cyclodehydrogenation of polyphenylene yielded the final product.
In the experimental part, low selectivity and low yields resulted in difficulties obtaining the target molecule.
Therefore, the final step of this synthesis was performed only few times.
Abstract (fin):Diplomityön tarkoituksena oli syntetisoida asfalteenien mallimolekyylejä.
Asfalteenit ovat raakaöljyn raskain osa, joka ei liukene n-heptaaniin, mutta liukenee tolueeniin.
Ne aiheuttavat öljynjalostusprosesseissa prosessilaitteiden likaantumista ja vetykrakkauskatalyytin deaktivoitumista.
Tutkimalla puhtaiden asfalteenimolekyylien avulla hydrokrakkauksen kinetiikkaa voidaan prosessin parametreja optimoida, jotta likaantuminen ja katalyytin deaktivoituminen vähentyisivät.
Asfalteeneille ei ole olemassa tiettyä molekyylirakennetta, vaan rakennetta on pyritty jäljittelemään erilaisten malliaineiden avulla.
Käytetyimpiä malliaineita ovat olleet pyreeni- ja polyaromaattijohdannaiset.
Asfalteenit koostuvat nykytietämyksen mukaan yhdestä polyaromaattisesta ytimestä, johon on kiinnittynyt alkyylisubstituentteja.
Asfalteenit sisältävät usein myös heteroatomeja, kuten rikkiä.
Molekyylipaino vaihtelee 500-1000 g/mol välillä ja fuusioituneiden renkaiden määrä on keskimäärin seitsemän.
Työn kirjallisuusosassa perehdytään pohjaöljyn jalostukseen ja koostumukseen, sekä suurten aromaattisten keskusten synteesiin.
Kokeellisessa osassa mallimolekyylinä syntetisoitiin suuri aromaattinen molekyyli 4,6,9,12,15,17-heksa-tert-butyyli-tetrabentso[bc,ef,hi,uv]ovaleeni Müllen et al. synteesimenetelmällä.
Lähtöaineena käytettiin pyreeniä, joka alkyloitiin Lewis-hapolla.
Alkyloitu pyreeni hapetettiin tämän jälkeen natriumperjodaatilla ja ruteenikloridilla.
Hapetuksessa muodostunut 2,7-di-tert-butyylipyreeni-4,5-dienoni reagoi Knoevenagel-reaktiolla diaryyliasetonin kanssa, minkä jälkeen Diels-Alder-reaktio difenyyliasetyleenin kanssa tuotti polyfenyleenin.
Haluttuun tuotteeseen päästiin polyfenyleenin syklodehydrauksella.
Reaktioiden huonot selektiivisyydet ja alhaiset saannot tuottivat ongelmia kokeellisen työn suorittamisessa.
Tämän vuoksi viimeinen reaktioaskel ehdittiin tehdä vain muutaman kerran.
ED:2014-08-31
INSSI record number: 49658
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