Araştırma Makalesi
BibTex RIS Kaynak Göster

Kimyasal Çöktürme Yöntemiyle Belirli Karboksilik Asitlerden Organosiklotrifosfazen Üretimi ve Kimyasal Özellikleri

Yıl 2019, Cilt: 4 Sayı: 3, 19 - 28, 25.12.2019

Öz

Belirli karboksilik asitlerden organosiklotirfosfazen üretimi için THF
çözücüsünde ve trietilamin varlığında oda koşullarında
hekzaklorosiklotrifosfazen ile bazı karboksilik
asitlerin tepkimeleri kimyasal çöktürme
yöntemiyle
yapıldı. Belirli karboksilik asitler olarak 4-kloro-benzoik
asit, 2-kloro-benzoik
asit ve 2-bromo-benzoik asit kullanıldı. Fosfazen
halkasına iki karboksilik asit grubunun bağlandığı bütün tepkimelerde
gözlemlendi. Reaksiyonda elde edilen trietilamonyum klorür tuzunun ağırlığı iki
tane karboksilik
asidin bağlandığını kanıtlamaktadır. Reaksiyonlarda karboksilik asidin
anhidridin oluştuğu gözlemlenmesine rağmen kaboksilik asidin nitrili ve
amidinin oluştuğu
gözlemlenmedi. NMR ve FTIR spektroskopileriyle üretilen
bileşiklerin yapıları incelendi. Sonuçların endüstriyel, biyomedikal ve kimya
mühendisliği uygulamaları için ilgi çekebileceği düşünülmektedir.

Kaynakça

  • [1] M. Gleria, R. D., Jaeger, “Aspects of phosphazene research” J. Inorg. Org. Polym., 2001, 11, pp.1-45.[2] S. B. Kocak, S. A, Z. A. Ozturk, T. Hokelek, Y. Oner, L. Acik, “Syntheses, spectroscopic properties, crystal structures, biological activities, and DNA interactions of heterocyclic amine substituted spiro-ansa-spiro- and spiro-bino-spiro-phosphazenes” Inorganıca Chımıca Acta , 2015, 406 , pp. 160-170.[3] C. J. Orme, M. K. Harrup, J. D. McCoy, D. H. Weinkauf, F. F. Stewart, “Pervaporation of water-dye, alcohol-dye, and water-alcohol mixtures using a polyphosphazene membrane” Journal Of Membrane Scıence, 2013, 197, 1-2, pp. 89-101.[4] H. R. Allcock, J. L. Desorcie, and G. H. Riding, “The organometallic chemistry of phosphazenes” Polyhedron, 1987, 6, pp. 119-157.[5] F. Aslan, A. I. Oztürk, B. Soylemez, “Synthesis of fluorescence organocyclotriphosphazene derivatives having functional groups such as formyl, Schiff base and both formyl and Schiff base without using Ar or N2 atmosphere” Journal of Molecular Structure, 2017, 1137, pp.387-395. [6] F. Aslan,1 A. I. Ozturk, M. Arslan, “The Reaction of N-Dichlorophosphoryl-P-trichlorophosphazene with Alkyl Grignard Reagents” Heteroatom Chemistry, 2003, 14, 5, pp. 413-416.[7] H. R. Allcock, “Phosphorue-Nitrogen Compounds,” Academic Press (New York and London), 1972, pp. 279- 281.[8] I. I. Bezman, W. R: Reed, “Nitrile Formation by Reaction of Triphosphonitrilic Chloride with Carboxylic Acid Salts,” J. Am. Chem Soc. 1960, Vol. 82 (May 5), pp. 2167-2168.[9] L. Caglıotı, M. Polonı, G. Rosını, “Phosphonitrilic Chloride as Activator of Carboxylic Acids. Formationof Amides and Hydrazides,” The Journal of Organic Chemistry, 1968, Vol. 99(No. 7), pp. 2979-2981.[10] M. Yokoyama, Y. Cho, R. Aıda, “Reactions of TriphosphonitrilicChloride with Carboxylic Acids,” Kgyo Kagaku Zasshi, 1963, 66, pp. 609-613.[11] A. Kılıç, S. Begeç, Z. Kılıç, T. Hökelek, “Phosphorus–nitrogen compounds: Part V. Phenolysis of p-trichloro-n-dichlorophosphorylmonophosphazene and the crystal structure of 1-(dichlorophosphinyl)-2-chloro-2,2-bis(2,4,6-tri-tertbutylphenoxy) phosphazene”, Journal of Molecular Structure, 2000, 516, pp. 255-262.[12] H. R. Allcock, R. Prange, “Poly(phosphazene-ethylene oxide) Di- and Triblock Copolymers as Solid Polymer Electrolytes”, Macromolecules, 2001, 34, pp. 4563-4570.Allcock, H. R.; Prange, R. Macromolecules 2001, 34,6858.Allcock, H. R.; Prange, R. Macromolecules 2001, 34,6858.[13] W. C. Allen, “The chemistry of phosphazenes”, journal of Chemical sociecity, Chemical Communication 1870, 32 pp. 152-157. [14] G. Bulloch, R. Keat, “Aminolysis reactions of 1-dichlorophosphinyl-2,2,2- trichlorophosphazene, Cl2P(O)•NxPCl3” Inorganica Chemica Acta, 1979, 33, pp. 245-248.[15] D. E. Brown, K. Ramachandran, K. R. Carter C. W. Allen, “Poly[(vinyloxy)cyclophosphazenes],” Macromolecules, 2001, 34, pp. 2870–2875.[16] M. Gümüşderelioğlu, A. Gür, “Synthesis, characterization, in vitro degradation and cytotoxicity of poly[bis(ethyl 4-aminobutyro) phosphazene]”Reactive & Functional Polymers, 2002, 52, pp. 71–80.[17] Y. Zhu, J. Fu, L. Zhu, X. Tang, X. Huang, “Preparation of novel hybrid inorganic–organic hollow microspheres via a self-template approach” Polymers International, 57, pp. 449–453, 2008.[18] B. Baroli, G. Delogu, A.M. Fadda, G. Podda C. Sinico, “Vesicle formation from hexasubstituted cyclophosphazenic derivatives,” International Journal of Pharmcy, 183, pp. 101–107, 1999.[19] A. Uslu, Ş. Güvenaltın, “The Investigation of Structural and Thermosensitive Poperties of New Phosphazene Derivatives Bearing Glycol and Amino Acid,” Dalton Trans. 2010, 39, pp.10685-10691.[20] A. Uslu, C. M. Balcı, F. Yuksel, E. Ozcan, S. Dural, S. Besli, “The investigation of thermosensitive properties of phosphazenederivatives bearing amino acid ester groups,” Journal of Molecular Structure, 2017, 1136, pp. 90-99.
Yıl 2019, Cilt: 4 Sayı: 3, 19 - 28, 25.12.2019

Öz

Kaynakça

  • [1] M. Gleria, R. D., Jaeger, “Aspects of phosphazene research” J. Inorg. Org. Polym., 2001, 11, pp.1-45.[2] S. B. Kocak, S. A, Z. A. Ozturk, T. Hokelek, Y. Oner, L. Acik, “Syntheses, spectroscopic properties, crystal structures, biological activities, and DNA interactions of heterocyclic amine substituted spiro-ansa-spiro- and spiro-bino-spiro-phosphazenes” Inorganıca Chımıca Acta , 2015, 406 , pp. 160-170.[3] C. J. Orme, M. K. Harrup, J. D. McCoy, D. H. Weinkauf, F. F. Stewart, “Pervaporation of water-dye, alcohol-dye, and water-alcohol mixtures using a polyphosphazene membrane” Journal Of Membrane Scıence, 2013, 197, 1-2, pp. 89-101.[4] H. R. Allcock, J. L. Desorcie, and G. H. Riding, “The organometallic chemistry of phosphazenes” Polyhedron, 1987, 6, pp. 119-157.[5] F. Aslan, A. I. Oztürk, B. Soylemez, “Synthesis of fluorescence organocyclotriphosphazene derivatives having functional groups such as formyl, Schiff base and both formyl and Schiff base without using Ar or N2 atmosphere” Journal of Molecular Structure, 2017, 1137, pp.387-395. [6] F. Aslan,1 A. I. Ozturk, M. Arslan, “The Reaction of N-Dichlorophosphoryl-P-trichlorophosphazene with Alkyl Grignard Reagents” Heteroatom Chemistry, 2003, 14, 5, pp. 413-416.[7] H. R. Allcock, “Phosphorue-Nitrogen Compounds,” Academic Press (New York and London), 1972, pp. 279- 281.[8] I. I. Bezman, W. R: Reed, “Nitrile Formation by Reaction of Triphosphonitrilic Chloride with Carboxylic Acid Salts,” J. Am. Chem Soc. 1960, Vol. 82 (May 5), pp. 2167-2168.[9] L. Caglıotı, M. Polonı, G. Rosını, “Phosphonitrilic Chloride as Activator of Carboxylic Acids. Formationof Amides and Hydrazides,” The Journal of Organic Chemistry, 1968, Vol. 99(No. 7), pp. 2979-2981.[10] M. Yokoyama, Y. Cho, R. Aıda, “Reactions of TriphosphonitrilicChloride with Carboxylic Acids,” Kgyo Kagaku Zasshi, 1963, 66, pp. 609-613.[11] A. Kılıç, S. Begeç, Z. Kılıç, T. Hökelek, “Phosphorus–nitrogen compounds: Part V. Phenolysis of p-trichloro-n-dichlorophosphorylmonophosphazene and the crystal structure of 1-(dichlorophosphinyl)-2-chloro-2,2-bis(2,4,6-tri-tertbutylphenoxy) phosphazene”, Journal of Molecular Structure, 2000, 516, pp. 255-262.[12] H. R. Allcock, R. Prange, “Poly(phosphazene-ethylene oxide) Di- and Triblock Copolymers as Solid Polymer Electrolytes”, Macromolecules, 2001, 34, pp. 4563-4570.Allcock, H. R.; Prange, R. Macromolecules 2001, 34,6858.Allcock, H. R.; Prange, R. Macromolecules 2001, 34,6858.[13] W. C. Allen, “The chemistry of phosphazenes”, journal of Chemical sociecity, Chemical Communication 1870, 32 pp. 152-157. [14] G. Bulloch, R. Keat, “Aminolysis reactions of 1-dichlorophosphinyl-2,2,2- trichlorophosphazene, Cl2P(O)•NxPCl3” Inorganica Chemica Acta, 1979, 33, pp. 245-248.[15] D. E. Brown, K. Ramachandran, K. R. Carter C. W. Allen, “Poly[(vinyloxy)cyclophosphazenes],” Macromolecules, 2001, 34, pp. 2870–2875.[16] M. Gümüşderelioğlu, A. Gür, “Synthesis, characterization, in vitro degradation and cytotoxicity of poly[bis(ethyl 4-aminobutyro) phosphazene]”Reactive & Functional Polymers, 2002, 52, pp. 71–80.[17] Y. Zhu, J. Fu, L. Zhu, X. Tang, X. Huang, “Preparation of novel hybrid inorganic–organic hollow microspheres via a self-template approach” Polymers International, 57, pp. 449–453, 2008.[18] B. Baroli, G. Delogu, A.M. Fadda, G. Podda C. Sinico, “Vesicle formation from hexasubstituted cyclophosphazenic derivatives,” International Journal of Pharmcy, 183, pp. 101–107, 1999.[19] A. Uslu, Ş. Güvenaltın, “The Investigation of Structural and Thermosensitive Poperties of New Phosphazene Derivatives Bearing Glycol and Amino Acid,” Dalton Trans. 2010, 39, pp.10685-10691.[20] A. Uslu, C. M. Balcı, F. Yuksel, E. Ozcan, S. Dural, S. Besli, “The investigation of thermosensitive properties of phosphazenederivatives bearing amino acid ester groups,” Journal of Molecular Structure, 2017, 1136, pp. 90-99.
Toplam 1 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Bölüm Makaleler
Yazarlar

Sultan Göktaş 0000-0002-8415-2073

Fatih Aslan

Yayımlanma Tarihi 25 Aralık 2019
Gönderilme Tarihi 18 Ocak 2019
Kabul Tarihi 22 Ocak 2019
Yayımlandığı Sayı Yıl 2019 Cilt: 4 Sayı: 3

Kaynak Göster

APA Göktaş, S., & Aslan, F. (2019). Kimyasal Çöktürme Yöntemiyle Belirli Karboksilik Asitlerden Organosiklotrifosfazen Üretimi ve Kimyasal Özellikleri. Harran Üniversitesi Mühendislik Dergisi, 4(3), 19-28.