THE EFFECTIVE PARAMETERS IN THE SYNTHESIS OF N-(1, 3-DIMETHYLBUTYL)-N'-PHENYL-P-PHENYLENEDIAMINE AS ANTIOZONANT AND ANTIOXIDANT FOR NATURAL AND SYNTHETIC ELASTOMERS

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KHALILI ALI ASGHAR; SHEKARRIZ MARZIEH; TAGHIPOOR SOHRAB; HAJIALIAKBARI FROZAN

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Journal: Nashrieh Shimi va Mohandesi Shimi Iran Year:2012 | Volume:31 | Issue:2 (65) Page(s): 1-12

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Title

THE EFFECTIVE PARAMETERS IN THE SYNTHESIS OF N-(1, 3-DIMETHYLBUTYL)-N'-PHENYL-P-PHENYLENEDIAMINE AS ANTIOZONANT AND ANTIOXIDANT FOR NATURAL AND SYNTHETIC ELASTOMERS

Author(s)

KHALILI ALI ASGHAR | SHEKARRIZ MARZIEH | TAGHIPOOR SOHRAB | HAJIALIAKBARI FROZAN | Issue Writer Certificate

Keywords

4-AMINODIPHENYLAMINE (4-ADPA)Q2

SANTOFLEX 6PPDQ2

RUBBER ANTIOXIDANTSQ2

RUBBER ANTIOZONANTSQ2

Abstract

N-(1, 3-Dimethylbutyl)-N'-phenyl-1, 4-phenylenediamine (Santoflex 6PPD) functions as a powerful antioxidant and antiozonant for natural and synthetic elastomeric compounds and as synthetic polymer stabilizer. Santo flex 6PPD provides protection against different forms of aging and fatigue degradation of flexible rubber components in both static and dynamic operation conditions at high temperature during storage and service operation is essential. In this research synthesis of this compound from 4-AminoDiPhenylAmine (4-ADPA) and Methyl Isobutyl Ketone (MIBK) in the presence of 5%Pt/C as catalyst with thermodynamic variables (temperature, pressure) and kinetic parameters (stirring speed, reaction time, and molar ratio) were examined with an oxidizer. At first, (4-nitrodiphenyl amine and -4-nitrosodiphenyi amine) were prepared by direct coupling of aniline and nitrobenzene under optimized molar ratio of hydrogen peroxide to moles nitrobenzene in the presence of a strong base. Then 4-ADPA was synthesized under hydrogen pressure about 200-220 psig at 80oC in the presence of 5%Pt/C as catalyst with efficiency increase about 10% and by product reduce compared to conventional methods. In the second step, 4-ADPA was reacted with Methyl Isobutyl Ketone (MIBK) under hydrogen pressure of about 800 psig and temperature of 170-175oC in the presence of 5% Pt/C catalyst Santo flex 6PPD was synthesized in 99% purity and the yield of reaction was 95% with efficiency increase about 3% in comparison with conventional methods. All of the synthesized compounds were characterized by FT-IR, 1HNMR, C.H.N and G. C. analysis.

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APA: Copy

KHALILI, ALI ASGHAR, SHEKARRIZ, MARZIEH, TAGHIPOOR, SOHRAB, & HAJIALIAKBARI, FROZAN. (2012). THE EFFECTIVE PARAMETERS IN THE SYNTHESIS OF N-(1, 3-DIMETHYLBUTYL)-N'-PHENYL-P-PHENYLENEDIAMINE AS ANTIOZONANT AND ANTIOXIDANT FOR NATURAL AND SYNTHETIC ELASTOMERS. NASHRIEH SHIMI VA MOHANDESI SHIMI IRAN (PERSIAN), 31(2 (65)), 1-12. SID. https://sid.ir/paper/26063/en

Vancouver: Copy

KHALILI ALI ASGHAR, SHEKARRIZ MARZIEH, TAGHIPOOR SOHRAB, HAJIALIAKBARI FROZAN. THE EFFECTIVE PARAMETERS IN THE SYNTHESIS OF N-(1, 3-DIMETHYLBUTYL)-N'-PHENYL-P-PHENYLENEDIAMINE AS ANTIOZONANT AND ANTIOXIDANT FOR NATURAL AND SYNTHETIC ELASTOMERS. NASHRIEH SHIMI VA MOHANDESI SHIMI IRAN (PERSIAN)[Internet]. 2012;31(2 (65)):1-12. Available from: https://sid.ir/paper/26063/en

IEEE: Copy

ALI ASGHAR KHALILI, MARZIEH SHEKARRIZ, SOHRAB TAGHIPOOR, and FROZAN HAJIALIAKBARI, “THE EFFECTIVE PARAMETERS IN THE SYNTHESIS OF N-(1, 3-DIMETHYLBUTYL)-N'-PHENYL-P-PHENYLENEDIAMINE AS ANTIOZONANT AND ANTIOXIDANT FOR NATURAL AND SYNTHETIC ELASTOMERS,” NASHRIEH SHIMI VA MOHANDESI SHIMI IRAN (PERSIAN), vol. 31, no. 2 (65), pp. 1–12, 2012, [Online]. Available: https://sid.ir/paper/26063/en

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