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Title: High-Yield Production of Fatty Nitriles by One-Step Vapor-Phase Thermocatalysis of Triglycerides

Abstract

Fatty nitriles are widely used as intermediate molecules in the pharmaceutical and polymer industries. In addition, hydrogenation of fatty nitriles produces fatty amines that are common surfactants. In the conventional fatty nitrile process, triglycerides are first hydrolyzed and the resulting fatty acids are catalytically reacted with NH3 in a liquid-phase reaction. In this study, we report a simpler one-step fatty nitrile production method that involves a direct vapor-phase reaction of triglycerides with NH3 in the presence of heterogeneous solid acid catalysts. The reactions were performed in a tubular reactor maintained at 400 °C into which triglycerides were injected through an atomizer to allow rapid volatilization and reaction; NH3 was fed as a gas. Several metal oxide catalysts were tested, and reactions in the presence of V2O5 resulted in near-theoretical fatty nitrile yields (84 wt % relative to the feed mass). In general, catalysts with higher acidity such as V2O5, Fe2O3, and ZnO showed higher fatty nitrile yields compared to low acidity catalysts such as ZrO, Al2O3, and CuO. Furthermore, energy balance calculations indicate that the one-step reaction described here would require significantly lower energy than the conventional process primarily because of the elimination of the energy-intense triglyceride hydrolysis.

Authors:
;  [1]; ORCiD logo;  [2]; ORCiD logo; ORCiD logo
  1. Department of Chemistry, University of California Riverside, Riverside, California 92521, United States
  2. Department of Chemical Engineering, Manhattan College, 3825 Corlear Avenue-Leo 422, Riverdale, New York 10463, United States
Publication Date:
Research Org.:
Univ. of Toledo, OH (United States)
Sponsoring Org.:
USDOE Office of Energy Efficiency and Renewable Energy (EERE), Bioenergy Technologies Office (EE-3B)
OSTI Identifier:
1413552
Alternate Identifier(s):
OSTI ID: 1498774
Grant/Contract Number:  
EE0005993
Resource Type:
Published Article
Journal Name:
ACS Omega
Additional Journal Information:
Journal Name: ACS Omega Journal Volume: 2 Journal Issue: 12; Journal ID: ISSN 2470-1343
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Shirazi, Yaser, Tafazolian, Hosein, Viamajala, Sridhar, Varanasi, Sasidhar, Song, Zhaoning, and Heben, Michael J. High-Yield Production of Fatty Nitriles by One-Step Vapor-Phase Thermocatalysis of Triglycerides. United States: N. p., 2017. Web. doi:10.1021/acsomega.7b01502.
Shirazi, Yaser, Tafazolian, Hosein, Viamajala, Sridhar, Varanasi, Sasidhar, Song, Zhaoning, & Heben, Michael J. High-Yield Production of Fatty Nitriles by One-Step Vapor-Phase Thermocatalysis of Triglycerides. United States. doi:10.1021/acsomega.7b01502.
Shirazi, Yaser, Tafazolian, Hosein, Viamajala, Sridhar, Varanasi, Sasidhar, Song, Zhaoning, and Heben, Michael J. Fri . "High-Yield Production of Fatty Nitriles by One-Step Vapor-Phase Thermocatalysis of Triglycerides". United States. doi:10.1021/acsomega.7b01502.
@article{osti_1413552,
title = {High-Yield Production of Fatty Nitriles by One-Step Vapor-Phase Thermocatalysis of Triglycerides},
author = {Shirazi, Yaser and Tafazolian, Hosein and Viamajala, Sridhar and Varanasi, Sasidhar and Song, Zhaoning and Heben, Michael J.},
abstractNote = {Fatty nitriles are widely used as intermediate molecules in the pharmaceutical and polymer industries. In addition, hydrogenation of fatty nitriles produces fatty amines that are common surfactants. In the conventional fatty nitrile process, triglycerides are first hydrolyzed and the resulting fatty acids are catalytically reacted with NH3 in a liquid-phase reaction. In this study, we report a simpler one-step fatty nitrile production method that involves a direct vapor-phase reaction of triglycerides with NH3 in the presence of heterogeneous solid acid catalysts. The reactions were performed in a tubular reactor maintained at 400 °C into which triglycerides were injected through an atomizer to allow rapid volatilization and reaction; NH3 was fed as a gas. Several metal oxide catalysts were tested, and reactions in the presence of V2O5 resulted in near-theoretical fatty nitrile yields (84 wt % relative to the feed mass). In general, catalysts with higher acidity such as V2O5, Fe2O3, and ZnO showed higher fatty nitrile yields compared to low acidity catalysts such as ZrO, Al2O3, and CuO. Furthermore, energy balance calculations indicate that the one-step reaction described here would require significantly lower energy than the conventional process primarily because of the elimination of the energy-intense triglyceride hydrolysis.},
doi = {10.1021/acsomega.7b01502},
journal = {ACS Omega},
number = 12,
volume = 2,
place = {United States},
year = {2017},
month = {12}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: 10.1021/acsomega.7b01502

Citation Metrics:
Cited by: 4 works
Citation information provided by
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Figures / Tables:

Figure-1 Figure-1: Pathways to produce fatty amines.

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Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.