Farklı fonksiyonel gruplar taşıyan katyonik gemini surfaktanların sentezi
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Dosyalar
Tarih
2014
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Trakya Üniversitesi Fen Bilimleri Enstitüsü
Erişim Hakkı
info:eu-repo/semantics/openAccess
Özet
Bu tez çalışmasında amit ve aminoasit fonksiyonel gruplarına sahip katyonik gemini sürfaktanların sentezi yapılmıştır. Amit fonksiyonlu katyonik gemini sürfaktanların sentezi için gerekli ara ürünler 3-dimetilaminopropilamin ile farklı açil halojenürlerin amitleşmesiyle elde edilmiştir. Bir ucunda amit fonksiyonel uzun bir alkil zinciri bulunan tersiyer amin ara ürünün dihaloalkanlar ile SN2 tipi reaksiyonuyla amit fonksiyonel katyonik gemini sürfaktanların sentezleri toplam iki basamakta gerçekleştirilmiştir. Sentezlerde birinci aşamada dekanoil klorür, dodekanoil klorür (Lauroil klorür), heksadekanoil klorür (palmitoil klorür) açil halojenür olarak kullanılmış, ikinci aşamada bağlantıyı oluşturmak içinse dihaloalkan olarak 1,3-dibromo propan, 1,6-dibromo heksan ve 1,10-dibromo dekan kullanılmıştır. Dokuz adet amit fonksiyonel katyonik gemini sürfaktan sentezlenmiştir. Amino asit fonksiyonel katyonik gemini sürfaktanların sentezi L-lizin metil ester dihidroklorür, L-Serine, L-Tirozin ve N-Asetil L-Sistein amino asitleri kullanılarak denenmiş, fakat bunlardan sadece L-lizin metil ester dihidroklorür ile gemini sürfaktan eldesi başarılmıştır. Öncelikle L-lizin metil ester dihidroklorür, bromoasetil bromür ile açillendirilmiş böylece aminoasit bağlantılı dihalojenür ara ürünü elde edilmiştir. İkinci aşamada ise bu ara ürünün farklı dimetilalkilaminlerle reaksiyonu vasıtasıyla dört adet L-Lizin bağlantısına sahip katyonik gemini sürfaktanın sentezi başarılmıştır. Bromoasetil bromür ile diğer aminoasitler fonksiyonellendirilememiştir.
Abstract
In this study, the synthesis of cationic gemini surfactants with amide and aminoacid functional groups were made. Required intermediates were produced from amidization of 3-dimethylaminopropylamine and acyl halides for the synthesis of amide functionalized cationic gemini surfactants. The synthesis of amide functionalized cationic gemini surfactants by SN2 type reaction of dihaloalkanes and tertier amine intermediates with amide functionalized long alkyl chain was performed in total two steps. In the first step, decanoyl chloride, dodecanoyl chloride (Lauroyl chloride), hexadecanoyl chloride (palmitoyl chloride) were used as acyl halide. In the second step, to making spacers 1,3-dibromopropane, 1,6-dibromohexane, 1,10-dibromodecane were used as dihaloalkane. Totally, nine amide functionalized cationic gemini surfactants were synthesized. In the synthesis of aminoacid functionalized cationic gemini surfactants, L-Lysine methyl ester dihydrochloride, L-Serine, L-Tyrosine and N-Acetyl L-Cystein were used but, the synthesis of aminoacid functionalized gemini surfactants was succeed only with L-Lysine methyl ester dihydrochloride. Initially, acylation of L-Lysine methyl ester dihydrochloride with bromoacetylbromide was performed consequently, aminoacid functionalized dihalogen compound was synthesized. Secondly, the synthesis of four cationic gemini surfactants with L-Lysine spacer were succeed by reaction of this intermediate with different dimethylalkylamines. Functionalization of other aminoacids with bromoacetylbromide was not achieved.
Abstract
In this study, the synthesis of cationic gemini surfactants with amide and aminoacid functional groups were made. Required intermediates were produced from amidization of 3-dimethylaminopropylamine and acyl halides for the synthesis of amide functionalized cationic gemini surfactants. The synthesis of amide functionalized cationic gemini surfactants by SN2 type reaction of dihaloalkanes and tertier amine intermediates with amide functionalized long alkyl chain was performed in total two steps. In the first step, decanoyl chloride, dodecanoyl chloride (Lauroyl chloride), hexadecanoyl chloride (palmitoyl chloride) were used as acyl halide. In the second step, to making spacers 1,3-dibromopropane, 1,6-dibromohexane, 1,10-dibromodecane were used as dihaloalkane. Totally, nine amide functionalized cationic gemini surfactants were synthesized. In the synthesis of aminoacid functionalized cationic gemini surfactants, L-Lysine methyl ester dihydrochloride, L-Serine, L-Tyrosine and N-Acetyl L-Cystein were used but, the synthesis of aminoacid functionalized gemini surfactants was succeed only with L-Lysine methyl ester dihydrochloride. Initially, acylation of L-Lysine methyl ester dihydrochloride with bromoacetylbromide was performed consequently, aminoacid functionalized dihalogen compound was synthesized. Secondly, the synthesis of four cationic gemini surfactants with L-Lysine spacer were succeed by reaction of this intermediate with different dimethylalkylamines. Functionalization of other aminoacids with bromoacetylbromide was not achieved.
Açıklama
Yüksek Lisans Tezi
Anahtar Kelimeler
Katyonik Gemini Sürfaktan, Nükleofilik Yer Değiştirme, Dihaloalkan, Tersiyer Amin, Aminoasit, Amit
