Biobased Aldehydes from Fatty Epoxides through Thermal Cleavage of β-Hydroxy Hydroperoxides*.
aldehydes
epoxides
flow chemistry
thermal cleavage
β-hydroxy hydroperoxides
Journal
ChemSusChem
ISSN: 1864-564X
Titre abrégé: ChemSusChem
Pays: Germany
ID NLM: 101319536
Informations de publication
Date de publication:
07 Jan 2021
07 Jan 2021
Historique:
received:
02
10
2020
revised:
29
10
2020
pubmed:
31
10
2020
medline:
16
6
2021
entrez:
30
10
2020
Statut:
ppublish
Résumé
The ring-opening of epoxidized methyl oleate by aqueous H
Identifiants
pubmed: 33125173
doi: 10.1002/cssc.202002364
doi:
Substances chimiques
Aldehydes
0
Epoxy Compounds
0
Oleic Acids
0
Oxides
0
molybdenum trioxide
22FQ3F03YS
nonanal
2L2WBY9K6T
methyl oleate
39736AJ06R
Molybdenum
81AH48963U
tungsten oxide
940E10M08M
Hydrogen Peroxide
BBX060AN9V
Tungsten
V9306CXO6G
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
379-386Subventions
Organisme : French Government
ID : ANR-001-01
Informations de copyright
© 2020 Wiley-VCH GmbH.
Références
B. A. Murray, “Reaction of aldehydes and ketones and their derivatives” in Org. React. Mech., 2016, pp. 1-70.
A. Corma, S. Iborra, A. Velty, Chem. Rev. 2007, 107, 2411-2502;
P. Gallezot, Chem. Soc. Rev. 2012, 41, 1538-1558;
M. Besson, P. Gallezot, C. Pinel, Chem. Rev. 2014, 114, 1827-1870;
R. A. Sheldon, Green Chem. 2014, 16,950-963.
R. Mariscal, P. Maireles-Torres, M. Ojeda, I. Sádaba, M. López Granados, Energy Environ. Sci. 2016, 1144-1189;
X. Li, P. Jia, T. Wang, ACS Catal. 2016, 6, 7621-7640;
Y. Luo, Z. Li, X. Li, X. Liu, J. Fan, J. H. Clark, C. Hu, Catal. Today 2019, 319, 14-24.
J. Lewkowski, Arkivoc, 2001, i 17-54;
R.-J. van Putten, J. C. van der Waal, E. de Jong, C. B. Rasrendra, H. J. Heeres, J. G. de Vries, Chem. Rev. 2013, 113, 1499-1597;
R. Karinen, K. Vilonen, M. Niemelä, ChemSusChem 2011, 4, 1002-1016;
A. A. Rosatella, S. P. Simeonov, R. F. M. Frade, C. A. M. Afonso, Green Chem. 2011, 13, 754-793;
X. Kong, Y. Zhu, Z. Fang, J. A. Kozinski, I. S. Butler, L. Xu, H. Song, X. Wei, Green Chem. 2018, 20, 3657-3682;
L. Hu, A. He, X. Liu, J. Xia, J. Xu, S. Zhou, J. Xu, ACS Sustainable Chem. Eng. 2018, 6, 15915-15935.
Z. Zhang, G. W. Huber, Chem. Soc. Rev. 2018, 47, 1351-1390;
P. Pal, S. Saravanamurugan, ChemSusChem 2019, 12, 145-163.
M. Fache, E. Darroman, V. Besse, R. Auvergne, S. Caillol, B. Boutevin, Green Chem. 2014, 16, 1987-1998;
M. Fache, B. Boutevin, S. Caillol, Eur. Polym. J. 2015, 68, 488-502;
M. Fache, B. Boutevin, S. Caillol, ACS Sustainable Chem. Eng. 2016, 4, 35-46.
U. Biermann, W. Friedt, S. Lang, W. Lìhs, G. Machmìller, J. O. Metzger, M. Rìsch gen. Klaas, H. J. Schäfer, M. P. Schneider, Angew. Chem. Int. Ed. 2000, 39, 2206-2224;
Angew. Chem. 2000, 112, 2292-2310;
U. Biermann, U. Bornscheuer, M. A. R. Meier, J. O. Metzger, H. J. Schäfer, Angew. Chem. Int. Ed. 2011, 50, 3854-3871;
Angew. Chem. 2011, 123, 3938-3956;
M. A. R. Meier, J. O. Metzger, U. S. Schubert, Chem. Soc. Rev. 2007, 36, 1788-1802;
Y. Xia, R. C. Larock, Green Chem. 2010, 12, 1893-1909;
J. M. Fraile, J. I. García, C. I. Herrerías, E. Pires, Synthesis 2017, 49, 1444-1460.
C. Kohlpaintner, M. Schulte, J. Falbe, P. Lappe, J. Weber, “Aldehydes, Aliphatic” in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2013.
For a review about hydroformylation of oleochemicals, see: T. Vanbésien, E. Monflier, F. Hapiot, Eur. J. Lipid Sci. Technol. 2016, 118, 26-35.
For our contribution on the reductive alkylation of polyols with aldehydes, see:
Y. Shi, W. Dayoub, A. Favre-Réguillon, G.-R. Chen, M. Lemaire, Tetrahedron Lett., 2009, 50, 6891-6893;
Y. Shi, W. Dayoub, G.-R. Chen, M. Lemaire, Green Chem. 2010, 12, 2189-2195;
C. Gozlan, R. Lafon, N. Duguet, A. Redl, M. Lemaire, RSC Adv. 2014, 4, 50653-50661;
M. Sutter, E. Da Silva, N. Duguet, Y. Raoul, E. Métay, M. Lemaire, Chem. Rev. 2015, 115, 8609-8651;
C. Gozlan, E. Deruer, M.-C. Duclos, V. Molinier, J.-M. Aubry, A. Redl, N. Duguet, M. Lemaire, Green Chem. 2016, 18, 1994-2004;
D. Belmessieri, C. Gozlan, M.-C. Duclos, V. Molinier, J.-M. Aubry, O. Dumitrescu, G. Lina, A. Redl, N. Duguet, M. Lemaire, Eur. J. Med. Chem. 2017, 128, 98-106;
D. Belmessieri, C. Gozlan, M.-C. Duclos, O. Dumitrescu, G. Lina, A. Redl, N. Duguet, M. Lemaire, Bioorg. Med. Chem. Lett. 2017, 27, 4660-4663.
B.-J. Kollbe Ahn, S. Kraft, X. S. Sun, J. Mater. Chem. 2011, 21, 9498;
M. Dierker, H. J. Schäfer, Eur. J. Lipid Sci. Technol. 2010, 112, 122-136.
D. L. Sparks, L. Antonio Estévez, R. Hernandez, Green Chem. 2009, 11, 986;
S. E. Dapurkar, H. Kawanami, T. Yokoyama, Y. Ikushima, Top. Catal. 2009, 52, 707-713;
B. R. Travis, R. S. Narayan, B. Borhan, J. Am. Chem. Soc. 2002, 124, 3824-3825.
G. Maerker, E. T. Haeberer, U. S. Patent, US 3405149, 1968;
S. Mithran, A. S. Subbaraman, Molecules 1999, 4, 159-164.
K. Louis, L. Vivier, J.-M. Clacens, M. Brandhorst, J.-L. Dubois, K. De Oliveira Vigier, Y. Pouilloux, Green Chem. 2014, 16, 96-101;
T. S. Omonov, E. Kharraz, P. Foleyb, J. M. Curtis, RSC Adv. 2014, 4, 53617-53627;
M. D. Lundin, A. M. Danby, G. R. Akien, T. P. Binder, D. H. Busch, B. Subramaniam, ACS Sustainable Chem. Eng. 2015, 3, 3307-3314.
N. D. Vu, B. Guicheret, N. Duguet, E. Metay, M. Lemaire, Green Chem. 2017, 19, 3390-3399.
E. Deruer, N. Duguet, M. Lemaire, ChemSusChem 2015, 8, 2481-2486;
N. D. Vu, S. Bah, E. Deruer, N. Duguet, M. Lemaire, Chem. Eur. J. 2018, 24, 8141-8150.
N. D. Spiccia, E. Border, J. Illesinghe, W. R. Jackson, A. J. Robinson, Synthesis 2013, 45, 1683-1688.
M. Lu, L. Peng, Q. Xie, N. Yang, H. Jin, Z. Wu, Y. Nie, X. Liu, X. Lu, J. Ji, Green Chem. 2019, 21, 560-566.
M. Lu, L. Peng, Q. Xie, Y. Nie, X. Liu, X. Lu, J. Ji, Eur. J. Lipid Sci. Technol. 2018, 120, 1700415.
L. Peng, Q. Xie, Y. Nie, X. Liu, M. Lu, J. Ji, RSC Adv. 2019, 9, 23061-23070.
Reporting GC yields is common practice in catalysis. However, in the specific case that is the cleavage of epoxides using H2O2, it may be not satisfactory. In the present study, we have clearly demonstrated that β-hydroxy hydroperoxides are formed as intermediates under mild conditions. If GC is only used to determine the yield of aldehydes without checking the full conversion of β-hydroxy hydroperoxide intermediates (e. g., by NMR spectroscopy or HPLC), it is misguiding because β-hydroxy hydroperoxides readily decomposed in the GC injector to form the desired aldehydes during the analysis. Consequently, the isolation of aldehydes is of prime importance.
N. D. Vu, Ph.D. thesis, Université Claude Bernard Lyon 1, defended 2018/11/19.
For early reports, see:
G. B. Payne, C. W. Smith, J. Org. Chem. 1957, 22, 1682-1685;
A. M. Mattucci, E. Perrotti, A. Santambrogio, Chem. Commun. 1970, 1198-1199.
The reaction was first reported uncatalyzed using 98 % H2O2, see: W. Adam, A. Rios, Chem. Commun. 1971, 822-823.
V. Subramanyam, C. L. Brizuela, A. H. Soloway, J. Chem. Soc. Chem. Commun. 1976, 508-509.
Y. Ogata, Y. Sawaki, H. Shimizu, J. Org. Chem. 1978, 43, 1760-1763.
X. Yan, C. Qiao, Z. Guo, Synlett 2013, 24, 502-506.
Y.-H. Liu, Z.-H Zhang, T.-S. Li, Synthesis 2008, 20, 3314-3318.
Y. Li, H.-D. Hao, Y. Wu, Org. Lett. 2009, 11, 2691-2694.
P.-H. Li, B.-L. Li, Z.-M. An, L.-P. Mo, Z.-S. Cui, Z.-H. Zhang, Adv. Synth. Catal. 2013, 355, 2952-2959.
Y.-H. Liu, H.-C. Hu, Z.-C. Ma, Y.-F. Dong, C. Wang, Y.-M. Pang, Monatsh. Chem. 2018, 149, 551-556.
I. Shinichiro, N. Sunao, N. Takuji, K. Hiroko, Jpn. Kokai Tokkyo Koho 2003342255.
V. Benessere, M. E. Cucciolito, A. D. Santis, M. D. Serio, R. Esposito, F. Ruffo, R. Turco, J. Am. Oil Chem. Soc. 2015, 92, 1701-1707.
Better results could probably be obtained using a more concentrated aqueous solution of H2O2 or ethereal H2O2, but no attempt was made for safety reasons.
Similar conditions were reported in a patent that was published during the finalization of the present article: C. Bordier, V. Escande, F. Caijot, C. Darcel, WO2020/169932. However, the deposit date of this patent occurred after the first communication of the present study, see reference 22.
G. Payne, C. W. Smith, J. Org. Chem. 1957, 22, 1682-1685;
W. Adam, A. J. Rios, Chem. Soc. Chem. Commun. 1971, 822;
V. Subramanyam, C. L. Brizuela, A. H. Soloway, J. Chem. Soc. Chem. Commun. 1976, 508-509.
W. Richardson, T. C. Heesen, J. Org. Chem. 1972, 37, 3416-3419;
Y. Ogata, Y. Sawaki, H. Shimizu, J. Org. Chem. 1978, 43, 1760-1763.
X. Gu, W. Zhang, R. G. Salomon, J. Org. Chem. 2012, 77, 1554-1559.
E. Antonelli, R. D'Aloisio, M. Gambaro, T. Fiorani, C. Venturello, J. Org. Chem. 1998, 63, 7190-7206.
F. Cataldo, Chem. Phys. Lipids 2013, 175-176, 41-49.
F. Cataldo, Tetrahedron Lett. 2015, 56, 994-998;
F. Cataldo, Ozone Sci. Eng. 2015, 37, 431-440.
S. Alazet, J. Preindl, R. Simonet-Davin, S. Nicolai, A. Nanchen, T. Meyer, J. Waser, J. Org. Chem. 2018, 19, 12334-12356.
The set-up for the cleavage of β-hydroxy hydroperoxide is described in the Supporting Information.
E. G. Sander, W. P. Jencks, J. Am. Chem. Soc. 1968, 90, 6154-6162.