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Friday, 19 May 2017

Revisiting the deoxydehydration of glycerol towards allyl alcohol under continuous-flow conditions

Green Chem., 2017, Advance Article
DOI: 10.1039/C7GC00657H, Paper
Nelly Ntumba Tshibalonza, Jean-Christophe M. Monbaliu
Highly selective flash deoxydehydration of glycerol towards allyl alcohol under continuous-flow conditions.

Revisiting the deoxydehydration of glycerol towards allyl alcohol under continuous-flow conditions



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Ms. Nelly Tshibalonza Ntumba

Nelly Tshibalonza
Nelly Tshibalonza was born in 1983 in Kinshasa, Congo. She received her diploma degree in Chemistry in 2006 from the University of Kinshasa. She is currently a fellow of the Belgian Technical Cooperation and is preparing a Ph.D. thesis on the development of catalytic methods to enhance the value of renewable raw materials.
E-mail: nel.tshibalonza@student.ulg.ac.be
Telephone: +32 (0)4 366-3493




http://pubs.rsc.org/en/Content/ArticleLanding/2017/GC/C7GC00657H?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract


Revisiting the deoxydehydration of glycerol towards allyl alcohol under continuous-flow conditions

 Author affiliations

Abstract

The deoxydehydration (DODH) of glycerol towards allyl alcohol was revisited under continuous-flow conditions combining a microfluidic reactor setup and a unique reactive dynamic feed solution approach. Short reaction times, high yield and excellent selectivity were achieved at high temperature and moderate pressure in the presence of formic acid, triethyl orthoformate, or a combination of both. Triethyl orthoformate appeared as a superior reagent for the DODH of glycerol, with shorter reaction times, lower reaction temperatures and more robust conditions. In-line IR spectroscopy and computations provided different perspectives on the unique reactivity of glycerol O,O,O-orthoesters.
Graphical abstract: Revisiting the deoxydehydration of glycerol towards allyl alcohol under continuous-flow conditions

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photo_JC_Monbaliu
JC M. Monbaliu, PhD.
Lecturer
Department of Chemistryjc.monbaliu@ulg.ac.be
t +32 (0) 4 366 35 10

Jean-Christophe M. Monbaliu

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Saturday, 25 February 2017

2-Methoxy-4-propylphenol

 
2-Methoxy-4-propylphenol
2-Methoxy-4-propylphenol
1H NMR (400 Mhz, CDCl3) δ (ppm): 6.83 (1H,d, J = 7.8 Hz), 6.68 (2H, d, J = 7.4 Hz), 5.47 (1H, s), 3.79 (3H, s), 2.52 (2H, t, J =7.6 Hz), 1.61 (2H, sext, J = 7.5 Hz) 0.94 (3H, t, J = 7.3 Hz).
13C NMR (100 MHz, CDCl3) δ (ppm) 146.4, 143.6,134.7, 121.0, 114.2, 111.1, 55.9, 37.8, 24.9, 13.8.
HRMS (ESI-TOF) m/z: [M + H]+ calculated for C10H15O2:167.1067; found: 167.1064.
DOI: 10.1021/acs.oprd.6b00441
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Saturday, 21 January 2017

Metal-free radical C-H methylation of pyrimidinones and pyridinones with dicumyl peroxide






Metal-free radical C-H methylation of pyrimidinones and pyridinones with dicumyl peroxide


Green Chem., 2017, Advance Article
DOI: 10.1039/C6GC03355E, Communication
Pei-Zhi Zhang, Jian-An Li, Ling Zhang, Adedamola Shoberu, Jian-Ping Zou, Wei Zhang
A method for free radical methylation of pyrimidinones and pyridinones with dicumyl peroxide under metal-free conditions is introduced. A 50 g-scale reaction could be performed safely. The product was separated by crystallization and the byproducts were recovery by distillation

http://pubs.rsc.org/en/Content/ArticleLanding/2017/GC/C6GC03355E?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

Metal-free radical C–H methylation of pyrimidinones and pyridinones with dicumyl peroxide

Pei-Zhi Zhang,a   Jian-An Li,a   Ling Zhang,a  Adedamola Shoberu,a   Jian-Ping Zou*a and  Wei Zhang*b  
*
Corresponding authors
a
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Soochow University, 199 Renai Street, Suzhou, China
 E-mail: jpzou@suda.edu.cn
b
Centre for Green Chemistry and Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Boulevard, Boston, USA
 E-mail: wei2.zhang@umb.edu
Green Chem., 2017, Advance Article

DOI: 10.1039/C6GC03355E


























A new method for free radical methylation of pyrimidinones and pyridinones with dicumyl peroxide (DCP) under metal-free conditions is introduced. A 50 g-scale reaction could be performed safely at the desired concentration. The reaction solvent and DCP derivative were readily recovered by distillation. The product was purified by crystallization to minimize the amount of waste.


2,6-diphenyl-5-methylpyrimidinone







Colorless solid, mp 258−260 °C, 73% yield (191 mg).

1H NMR (400 MHz, DMSO-d6): δ 12.85 (s, 1H), 8.17 (d, J = 7.1 Hz, 2H), 7.68 (d, J = 6.6 Hz, 2H), 7.53 (dd, J = 14.3, 6.8 Hz, 6H), 2.10 (s, 3H).

13C NMR (101 MHz, CDCl3): δ 161.15, 152.97, 138.68, 132.26, 131.62, 129.11, 129.02, 128.86, 128.15, 127.45, 119.09, 12.65.

 HRMS (ESI-TOF) m/z: (M+H)+ Calcd for C17H15N2O 263.1184, found 263.1194.





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Wednesday, 7 December 2016

Organic Chemistry International Blog selected by Feedspot as one of the Top 50 Chemistry Blogs on the web.





My blog Organic Chemistry International was selected by Feedspot as one of the Top 50 Chemistry Blogs on the web. 
link is..........http://organicchemistrysite.blogspot.in/ 

FEEDSPOThttp://blog.feedspot.com/chemistry_websites/





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Sunday, 27 November 2016

Improving the efficiency of the Diels-Alder process by using flow chemistry and zeolite catalysis




  • Green Chem., 2017, Advance Article
    DOI: 10.1039/C6GC02334G, Paper
    S. Seghers, L. Protasova, S. Mullens, J. W. Thybaut, C. V. Stevens
    The industrial application of the Diels-Alder reaction for the synthesis of (hetero)cyclic compounds constitutes an important challenge. To tackle the reagent instability problems and corresponding safety issues, the use of a high-pressure and zeolite catalysed microreactor process is presented.
The industrial application of the Diels–Alder reaction for the atom-efficient synthesis of (hetero)cyclic compounds constitutes an important challenge. Safety and purity concerns, related to the instability of the polymerization prone diene and/or dienophile, limit the scalability of the production capacity of Diels–Alder products in a batch mode. To tackle these problems, the use of a high-pressure continuous microreactor process was considered. In order to increase the yields and the selectivity towards the endo-isomer, commercially available zeolites were used as a heterogeneous catalyst in a microscale packed bed reactor. As a result, a high conversion (≥95%) and endo-selectivity (89 : 11) were reached for the reaction of cyclopentadiene and methyl acrylate, using a 1 : 1 stoichiometry. A throughput of 0.87 g h−1during at least 7 h was reached, corresponding to a 3.5 times higher catalytic productivity and a 14 times higher production of Diels–Alder adducts in comparison to the heterogeneous lab-scale batch process. Catalyst deactivation was hardly observed within this time frame. Moreover, complete regeneration of the zeolite was demonstrated using a straightforward calcination procedure


Improving the efficiency of the Diels–Alder process by using flow chemistry and zeolite catalysis

S. Seghers,a   L. Protasova,b   S. Mullens,b  J. W. Thybautc and   C. V. Stevens*a  
*
Corresponding authors
a
SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium
E-mail: chris.stevens@ugent.be
b
VITO, Vlaamse Instelling voor Technologisch Onderzoek, Boeretang 200, 2400 Mol, Belgium
c
Laboratory for Chemical Technology, Department of Chemical Engineering and Technical Chemistry, Faculty of Engineering and Architecture, Ghent University, Technologiepark 914, 9052 Ghent, Belgium
Green Chem., 2017, Advance Article

DOI: 10.1039/C6GC02334G
http://pubs.rsc.org/en/Content/ArticleLanding/2017/GC/C6GC02334G?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract






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Friday, 28 October 2016

Solvent- and halide-free synthesis of pyridine-2-yl substituted ureas through facile C-H functionalization of pyridine N-oxides



Solvent- and halide-free synthesis of pyridine-2-yl substituted ureas through facile C-H functionalization of pyridine N-oxides

Green Chem., 2016, Advance Article
DOI: 10.1039/C6GC02556K, Paper
Valentin A. Rassadin, Dmitry P. Zimin, Gulnara Z. Raskil'dina, Alexander Yu. Ivanov, Vadim P. Boyarskiy, Semen S. Zlotskii, Vadim Yu. Kukushkin
A solvent- and halide-free atom-economical synthesis of practically useful pyridine-2-yl substituted ureas utilizes pyridine N-oxides and dialkylcyanamides.


Solvent- and halide-free synthesis of pyridine-2-yl substituted ureas through facile C–H functionalization of pyridine N-oxides


*
Corresponding authors
a
Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab. 7/9, 199034 Saint Petersburg, Russia
E-mail: v.rassadin@spbu.ruv.kukushkin@spbu.ru
b
Ufa State Petroleum Technological University, Kosmonavtov 1, Ufa, Bashkortostan, Russia
c
Research Park SPbSU, Center for Magnetic Resonance, Saint Petersburg State University, Universitetskaya Nab. 7/9, 199034 Saint Petersburg, Russia
Green Chem., 2016, Advance Article

DOI: 10.1039/C6GC02556K






























A novel solvent- and halide-free atom-economical synthesis of practically useful pyridine-2-yl substituted ureas utilizes easily accessible or commercially available pyridine N-oxides (PyO) and dialkylcyanamides. The observed C–H functionalization of PyO is suitable for the good-to-high yielding synthesis of a wide range of pyridine-2-yl substituted ureas featuring electron donating and electron withdrawing, sensitive, or even fugitive functional groups at any position of the pyridine ring (63–92%; 19 examples). In the cases of 3-substituted PyO, the C–H functionalization occurs regioselectively providing a route for facile generation of ureas bearing a 5-substituted pyridine-2-yl moiety.



1,1-Dimethyl-3-(pyridin-2-yl)urea







1,1-Dimethyl-3-(pyridin-2-yl)urea (4a)3 : From pyridine 1-oxide (1a) (95.0 mg, 1.00 mmol) and dimethylcyanamide (2a) (105 mg, 1.50 mmol), compound 4a (147 mg, 89%) was obtained according to GP1 as a yellow oil, which was then crystalized in the freezer to give pale yellow solid, m.p. = 42.6–43.5 °C, lit.4 m.p. = 44–47 °C (EtOAc/hexane), Rf = 0.25 (EtOAc). 1H NMR (400 MHz, CDCl3): δ = 3.00 (s, 6 H, NCH3), 6.88 (ddd, J = 7.3, 5.0, 0.9 Hz, 1 H), 7.30 (br. s, 1 H), 7.60 (ddd, J = 8.5, 7.3, 1.9 Hz, 1 H), 8.02 (dt, J = 8.5, 0.9 Hz, 1 H), 8.14 (ddd, J = 5.0, 1.9, 0.9 Hz, 1 H) ppm. 13C NMR (101 MHz, CDCl3): δ = 36.3 (2 С, CH3), 113.0 (CH), 118.1 (CH), 138.0 (CH), 147.3 (CH), 152.8 (C), 154.8 (C) ppm. NMR data are consistent with previously reported.3 HRMS (ESI), m/z: [M + H]+ calcd. for C8H12N3O+ : 166.0975; found: 166.0977.


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Sunday, 9 October 2016

ENZYMES AS GREEN CATALYSTS FOR PHARMACEUTICAL INDUSTRY


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ENZYMES AS GREEN CATALYSTS FOR PHARMACEUTICAL INDUSTRY
  'Green' Catalysts for 'greener' reactions - Dr. Dinesh Nair, Regional Business Manager at Novozymes South Asia Pvt. Ltd







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