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Author:Jumppanen, Mikael
Title:Suberiinin rasvahappojen hyödyntäminen pinnoite- ja pakkaussovelluksissa
Exploiting suberin fatty acids in coating and packaging applications
Publication type:Master's thesis
Publication year:2013
Pages:viii + 73 + [29]      Language:   fin
Department/School:Kemian laitos
Main subject:Orgaaninen kemia   (Kem-4)
Supervisor:Jokela, Reija
Instructor:Pirttimaa, Minni ; Hulkko, Janne
OEVS:
Electronic archive copy is available via Aalto Thesis Database.
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Location:P1 Ark Aalto  1974   | Archive
Keywords:suberin
tungstic acid
phase transfer catalyst
aminidification
oxidation
suberiini
volframihappo
faasinsiirtokatalyytti
amidointi
hapetus
Abstract (eng): Generally, the literature survey introduces coating and packaging materials and reviews industrial carboxylic acid chemical modifications for polymerization applications like polyesterification, amidification and oxidation methods.
Focus is on tungstic acid and phase transfer catalyst catalysed hydrogen peroxide oxidation in a water solution and on deep study of its mechanism.
Factors affecting the function of catalyst are acidity of solvent and free ions, which can either improve or weaken the activity of catalyst through ligandation.
In addition, biosynthesis of suberin fatty acids main components is reviewed.

In the experimental part, a method for extracting suberin fatty acids is shown.
In the developed method the extraction solvent was changed from toluene to water, which led to much purer products.
In addition, experimental part covers chemical modification of suberin fatty acids for polymer industry applications.
Focus was on tungstic acid and phase transfer catalyst catalysed oxidative cleavage of fatty acids by using hydrogen peroxide as oxidant in water.
Best results were achieved by using tetrabutylammonium hydrogen sulfate (TBA) as phase transfer catalyst.
TBA's counter ion hydrogensulfate doesn't form a complex with tungsten which affects the reaction by lowering catalyst activity.
Also reduction, amidification through acid chloride by bubbling ammonia and direct amidification with urea were studied by using azelaic acid as a model substance.
Best amidification results were obtained by using direct amidification of carboxylic acids with urea.
Abstract (fin): Kirjallisessa osassa esitellään pinnoitteita ja pakkausmateriaaleja yleisesti sekä teollisia karboksyylihappojen modifiointimenetelmiä polymeerisovelluksiin kuten polyesterointi-, amidointi- sekä hapetusmenetelmiä.
Hapetusmenetelmissä keskitytään volframihappokatalysoituun vetyperoksidihapetukseen vesiliuoksessa faasinsiirtokatalyytin avulla ja katalyysimekanismin syvälliseen tarkasteluun.
Katalyytin toimintaan vaikuttavia tekijöitä ovat liuoksen happamuus ja liuoksessa olevat ionit, jotka voivat muodostaa joko katalyytin tehoa huonontavia tai parantavia komplekseja.
Lisäksi kirjallisessa osassa esitellään suberiinin rasvahappojen pääkomponentteina biosynteesi sekä suberiinin ja sen rasvahappojen nykyisiä sovelluksia.

Kokeellinen osa käsittelee suberiinin rasvahappojen eristysmenetelmän kehittämistä ja rasvahappojen analysointia.
Kehitetyssä menetelmässä vaihdettiin uuttoliuotin tolueenista veteen, minkä seurauksena saatiin eristettyä huomattavasti vähemmän epäpuhtauksia sisältäviä rasvahappoja.
Lisaksi kokeellinen osa käsittelee eristettyjen rasvahappojen kemiallista modifiointia polymeeriteollisuuden sovelluksiin.
Rasvahappojen kemiallinen modifiointi keskittyi volframihappo- ja faasinsiirtokatalysoituun hapettavaan katkaisuun vetyperoksidilla.

Tutkimusten perusteella havaittiin, että parhaaseen hapetustulokseen päästään käyttämällä faasinsiirtokatalyyttina tetrabutyyliammoniumvetysulfaattia, jonka vastaioni vetysulfaatti ei heikennä volframihappokatalyytin tehoa.
Myös rasvahappojen pelkistystä dioleiksi, amidointia happokloridin kautta kuplittamalla ammoniakkikaasulla sekä suoraa amidointia urealla tutkittiin käyttämällä malliaineena atselaiinihappoa.
Parhaaseen tulokseen päästiin atselaiinihapon reaktiolla urean kanssa.
ED:2013-04-08
INSSI record number: 46057
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