Alkandiil-α,ω-bis(dimetilalkilamonyumbromür) tipi dimerik sürfaktanların sentezi ve faz transfer katalizörü özelliklerinin incelenmesi
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Dosyalar
Tarih
2013
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Trakya Üniversitesi Fen Bilimleri Enstitüsü
Erişim Hakkı
info:eu-repo/semantics/openAccess
Özet
Bu tezin birinci kısmında alkandiil bis(dimetilalkilamonyum bromür) tipi dimerik sürfaktanların sentezi gerçekleştirilmiştir. Öncelikle fonksiyonel grup taşımayan düz zincirli dimerik sürfaktanlar ya N,N,N',N'-tetrametil etilendiamin 'in alkil halojenürlerle ya da dimetilalkil aminlerin dihaloalkanlarla SN2 tipi reaksiyonlarıyla sentezlenmiştir. Özellikle biyolojik olarak bozunabilirlikleriyle ilgi çeken esterkuat dimerik sürfaktanlar bromoasetil bromür veya çeşitli açil halojenürlerden yola çıkılarak iki aşamada sentezlenmiştir. Altı adet düz zincirli, ondört adet ester fonksiyonel olmak üzere toplam yirmi adet dimerik sürfaktanın sentezi yapılmıştır. Kuaterner amonyum bileşiklerinin organik sentezlerde faz transfer katalizörü olarak kullanımları bilinmektedir. Fakat dimerik kuaterner amonyum bileşiklerinin çift fazlı reaksiyonlarda faz transfer katalizörü olarak kullanıldığı örnek bulunmamaktadır. Tezin ikinci kısmında sentezlenen dimerik sürfaktanlardan seçilen sekiz tanesi izovanilin'in O-oktillenmesi ve O-siklopentillenmesi reaksiyonunda faz transfer katalizörü olarak kullanılmıştır. Reaksiyonlar faz transfer katalizörü olmaksızın ve klasik faz transfer katalizörü tetrabütilamonyum bromür ile de uygulanmış ve sonuçlar dimeriklerin reaksiyonları ile karşılaştırılmıştır. Alkandiil , bis(dimetil-alkilamonyum bromür) tipi dimerik sürfaktanların faz transfer katalizli alkilleme reaksiyonlarında başarılı şekilde faz transfer katalizörü davranışı sergilediği görülmüştür.
Abstract
In the first part of this thesis, synthesis of alkandiyl, bis(dimethyl-alkylammonium bromide) dimeric surfactants was accomplished. At first, quaternary ammonium dimeric surfactants which have simple chain without functional groups were synthesized by SN2 type reactions of either N,N,N',N'-tetramethylethylene diamine with different alkyl halides or dimethylalkyl amines with dihaloalkanes. Esterquat dimeric surfactants which recently have attracted attention with biodegradable properties were synthesized from bromoacetyl bromide or different acyl halides in two steps. Six of them have simple alkyl chains and fourteen of them have hydrophobic alkyl chains containing ester functional groups in different chain lenghts totally twenty dimeric surfactants were synthesized. It is known that quaternary ammonium compounds are used as phase transfer catalyst in organic synthesis. But there is no example that dimeric quaternary ammonium compounds are used as phase transfer catalyst in two phase reactions. In the second part of this thesis, eight compounds from synthesized dimeric surfactants were used in O-octylation and O-cyclopentylation of isovanilin as phase transfer catalysts. These reactions were made both by traditional phase transfer catalyst tetrabutylammonium bromide and without catalyst and results were compared with those of dimeric surfactants. Consequently, ıt was expressed that alkandiy ,bis(dimethylalkylammonium bromide) dimeric surfactants successively exhibit character of phase transfer catalysts.
Abstract
In the first part of this thesis, synthesis of alkandiyl, bis(dimethyl-alkylammonium bromide) dimeric surfactants was accomplished. At first, quaternary ammonium dimeric surfactants which have simple chain without functional groups were synthesized by SN2 type reactions of either N,N,N',N'-tetramethylethylene diamine with different alkyl halides or dimethylalkyl amines with dihaloalkanes. Esterquat dimeric surfactants which recently have attracted attention with biodegradable properties were synthesized from bromoacetyl bromide or different acyl halides in two steps. Six of them have simple alkyl chains and fourteen of them have hydrophobic alkyl chains containing ester functional groups in different chain lenghts totally twenty dimeric surfactants were synthesized. It is known that quaternary ammonium compounds are used as phase transfer catalyst in organic synthesis. But there is no example that dimeric quaternary ammonium compounds are used as phase transfer catalyst in two phase reactions. In the second part of this thesis, eight compounds from synthesized dimeric surfactants were used in O-octylation and O-cyclopentylation of isovanilin as phase transfer catalysts. These reactions were made both by traditional phase transfer catalyst tetrabutylammonium bromide and without catalyst and results were compared with those of dimeric surfactants. Consequently, ıt was expressed that alkandiy ,bis(dimethylalkylammonium bromide) dimeric surfactants successively exhibit character of phase transfer catalysts.
Açıklama
Yüksek Lisans Tezi
Anahtar Kelimeler
Faz Transfer Katalizörü, O-Alkilasyon, Katyonik Gemini Sürfaktanlar, Esterkuat Geminiler, Phase Transfer Catalyst, O- Alkylation, Cationic Gemini Surfactants, Esterquat Geminis
