Synthesis, characterization and evaluation of some pyranopyrazoles and pyranopyrimidines derivatives as antioxidants for lubricating oils
Other Title(s)
تحضير و تشخيص و تقييم بعض مشتقات البايرنوبايرزل و البايرنوبيرميدين كمضادات أكسدة في زيوت التزييت
Joint Authors
al-Misri, Zaynab Abd al-Zahrah Khudayr
Muhammad, Abd al-Halim Abd al-Karim
Khalil, Muhammad Rifat Ahmad
Ali, Yusuf
Source
Issue
Vol. 55, Issue 1 (31 Mar. 2014), pp.1-11, 11 p.
Publisher
University of Baghdad College of Science
Publication Date
2014-03-31
Country of Publication
Iraq
No. of Pages
11
Main Subjects
Topics
Abstract AR
حضر المركب (2) 6-Amino -4- (4-hydroxyphenyl)-5-cyano-3-methyl-1-phenyl-1,4- dihydropyrano [2,3-c] pyrazole من تكاثف 3-methyl-1-phenyl-2-pyrazolin-5-one مع المركب (1) [2-(4-hydroxy-benzylidine) malononitrile] المحضر بواسطة تكاثف Knoevenagel لمشتق 4-hydroxy benzaldehyde مع malononitrile [.
تم مفاعلة المركب (2) مع كل من حامض الفورميك و الفورمامايد و ثايوسيانات الامونيوم باستخدام المايكروويف لتحضير 4-(4-hydroxyphenyl)- 3-methyl-1-phenyl-4,6-dihydro- pyrazolo[3', 4':5,6]pyrano[2,3-d]pyrimidine-5-one (compound 3), 4-(4-hydroxyphenyl)- 3-methyl-1-phenyl-4,6-dihydro- pyrazolo[3', 4':5,6]pyrano[2,3-d]pyrimidine-5-imine (compound 4) and N-[4-(4-hydroxyphenyl)- 3-methyl-1-phenyl-7-thioxo-7,8- dihydropyrazolo [3', 4':5,6] pyrano [2,3-d] pyrimidine-5-yl] thiourea (compound 5) على التوالي.
كما حضرت قواعد شيف 6 (a-f) من تفاعل المركب (2) مع الديهايدات مختلفة. شخصت المركبات المحضرة بوساطة مطيافية الأشعة تحت الحمراء و قسم منها بمطيافية الرنين النووي المغناطيسي للبروتون و الكربون كما تم تقييمها كمضادات للأكسدة بخلط 1% من كل مركب مع زيت الأساس من نوع 60 stock المجهز من شركة مصافي الوسط.
أظهر خليط الزيت مع المركب 6a ثباتية عالية تجاه الأكسدة مقارنة مع زيت الأساس بينما مزيج الزيت مع المركب المحضر 5 أظهر ثباتية تجاه الأكسدة أعلى من مزيج الزيت مع المادة المضادة للأكسدة المستخدمة في شركة مصافي الوسط.
Abstract EN
6-Amino-4-(4-hydroxyphenyl)-5-cyano-3-methyl-1-phenyl-1, 4-dihydropyrano [2, 3-c] pyrazole (compound 2) was prepared by condensation of 2-(4-hydroxylbenzylidine) malononitrile (compound 1) [which was prepared by Knoevenagel condensation of malononitrile with 4-hydroxy benzaldehyde ] with 3-methyl-1-phenyl-2-pyrazolin-5-one.
Reactions of compound 2 with different reagents formic acid, formamide, and ammonium thiocyanate under microwave irradiation leads to the synthesis of 4-(4-hydroxyphenyl)- 3-methyl-1-phenyl-4,6-dihydro- pyrazolo [3', 4':5,6] pyrano [2,3-d] pyrimidine-5-one (compound 3), 4-(4-hydroxyphenyl)- 3-methyl-1-phenyl-4, 6-dihydro- pyrazolo [3', 4':5,6]pyrano[2,3-d]pyrimidine-5-imine (compound 4) and N-[4-(4-hydroxyphenyl)- 3-methyl-1-phenyl-7-thioxo-7,8- dihydropyrazolo [3', 4':5,6] pyrano [2,3-d] pyrimidine-5-yl] thiourea (compound 5) respectively.
Moreover a series of Schiff bases 6(a-f) were prepared by reaction of compound 2 with different aromatic aldehydes.
The prepared compounds were characterized by FTIR, and most 1HNMR, 13CNMR and evaluated as antioxidant additives by blending 1 % of each compound with base lubricating oil 60 stock supplied by Midland Refineries Company, Baghdad, Iraq.
The formulated blend of compound 6a showed better oxidation stability compared with the base oil (blank), while the oil blend of compound 5 gave higher oxidation stability than the blend with standard antioxidant supplied by Midland Refineries Company.
American Psychological Association (APA)
Khalil, Muhammad Rifat Ahmad& Muhammad, Abd al-Halim Abd al-Karim& Ali, Yusuf& al-Misri, Zaynab Abd al-Zahrah Khudayr. 2014. Synthesis, characterization and evaluation of some pyranopyrazoles and pyranopyrimidines derivatives as antioxidants for lubricating oils. Iraqi Journal of Science،Vol. 55, no. 1, pp.1-11.
https://search.emarefa.net/detail/BIM-373210
Modern Language Association (MLA)
Khalil, Muhammad Rifat Ahmad…[et al.]. Synthesis, characterization and evaluation of some pyranopyrazoles and pyranopyrimidines derivatives as antioxidants for lubricating oils. Iraqi Journal of Science Vol. 55, no. 1 (2014), pp.1-11.
https://search.emarefa.net/detail/BIM-373210
American Medical Association (AMA)
Khalil, Muhammad Rifat Ahmad& Muhammad, Abd al-Halim Abd al-Karim& Ali, Yusuf& al-Misri, Zaynab Abd al-Zahrah Khudayr. Synthesis, characterization and evaluation of some pyranopyrazoles and pyranopyrimidines derivatives as antioxidants for lubricating oils. Iraqi Journal of Science. 2014. Vol. 55, no. 1, pp.1-11.
https://search.emarefa.net/detail/BIM-373210
Data Type
Journal Articles
Language
English
Notes
Includes bibliographical references : p. 11
Record ID
BIM-373210