10.1002/cssc.202001052
ChemSusChem
COMMUNICATION
[1]
a) R. W. Johnson, C. M. Pollock, R. R. Cantrell, Dicarboxylic Acids, in
T. Peng, Catal. Sci. Technol. 2017, 7, 2506-2511; k) Z. Shao, Y. Wang,
Y. Liu, Q. Wang, X. Fu, Q. Liu, Org. Chem. Front. 2018, 5, 1248-1256.
[16] With catalytic systems reported in references 15a, 15d, and 15i, the
yields of dicarboxylic acids from diols were moderate to low, which was
because of the formation of lactones as by-products.
Kirk-Othmer Encyclopedia of Chemical Technology, Wiley-VCH,
Weinheim,
2010.
DOI:
10.1002/0471238961.0409030110150814.a01.pub2; b) B. Cornils, P.
Lappe, Dicarboxylic Acids, Aliphatic, in Ullmann's Encyclopedia of
Industrial
Chemistry,
Wiley-VCH,
Weinheim,
2014.
DOI:
[17] Catalytic systems for the transformation of diols to lactones have been
also reported: a) J. Zhao, J. F. Hartwig, Organometallics 2005, 24,
2441-2446; b) S. Musa, I. Shaposhnikov, S. Cohen, D. Gelman, Angew.
Chem. 2011, 123, 3595-3599; Angew. Chem. Int. Ed. 2011, 50, 3533-
3537; c) J. Zhang, E. Balaraman, G. Leitus, D. Milstein,
Organometallics 2011, 30, 5716–5724; d) K. Fujita, W. Ito, R.
Yamaguchi, ChemCatChem 2014, 6, 109-112; e) A. Bhatia, M. Kannan,
S. Muthaiah, Synlett 2019, 30, 721-725.
10.1002/14356007.a08_523.pub3
[2]
a) K. Osowska-Pacewicka, H. Alper, J. Org. Chem. 1988, 53, 808-810;
b) Y. Usui, K. Sato, Green Chemistry 2003, 5, 373-375; c) C.-M. Che,
W.-P. Yip, W.-Y. Yu, Chem. Asian J. 2006, 1, 453-458; d) L. Rokhum,
G. Bez, Synth. Commun. 2011, 41, 548-552; e) K. C. Hwang, A.
Sagadevan, Science 2014, 346, 1495-1498; f) D. Lisicki, B. Orlieńska,
Pol. J. Chem. Tech. 2018, 20, 102-107.
[3]
[4]
BCC Research. (US), “Global Markets for Adipic Acid”, can be found in
acid.html, 2019.
[18] K. Fujita, Bull. Chem. Soc. Jpn. 2019, 92, 344-351.
[19] See also, K. Fujita, R. Tamura, Y. Tanaka, M. Yoshida, M. Onoda, R.
Yamaguchi, ACS Catal. 2017, 7, 7226-7230.
a) M. T. Musser, Adipic Acid, in Ullmann's Encyclopedia of Industrial
[20] M. Kuwahara, M. Nishioka, M. Yoshida, K. Fujita, ChemCatChem 2018,
10, 3636-3640.
Chemistry,
Wiley-VCH,
Weinheim,
2000.
DOI:
Leshkov, Catal. Sci. Technol. 2013, 3, 1465-1479.
[21] This reaction gave a mixture of 2,4-diethylglutaric acid with dl and meso
form in the ratio of 50:50, although the ratio of dl and meso form of
starting diol was 44:56.
[5]
a) S. Dunn, Int. J. Hydrogen Energy 2002, 27, 235-264; b) L. Barreto, A.
Makihira, K. Riahi, Int. J. Hydrogen Energy 2003, 28, 267-284; c) G.
Marbán, T. Valdés-Solís, Int. J. Hydrogen Energy 2007, 32, 1625-1637;
d) A. Sartbaeva, V. L. Kuznetsov, S. A. Wells, P. P. Edwards, Energy
Environ. Sci. 2008, 1, 79-85.
[22] a) A. F. Sousa, C. Vilela, A. C. Fonseca, M. Matos, C. S. R. Freire, G.-J.
M. Gruter, J. F. J. Coelho, A. J. D. Silvestre, Polym. Chem. 2015, 6,
5961-5983; b) S. Hameed, L. Lin, A. Wang, W. Luo, Catalysts. 2020, 10,
120.
[6]
[7]
a) D.-Y. Lee, A. Elgowainy, Q. Dai, Appl. Energy 2018, 217, 467-479;
b) H. Khasawneh, M. N. Saidan, M. Al-Addous, Energy Explor. Exploit.
2019, 37, 1053-1072.
[23] a) M. Schrꢀder, Chem. Rev. 1980, 80, 187-213; b) H. C. Kolb, M. S.
VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483-2547; c)
C. J. R. Bataille, T. J. Donohoe, Chem. Soc. Rev. 2011, 40, 114-128.
[24] a) S. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunaga, K. B.
Hansen, A. E. Gould, M. E. Furrow, E. N. Jacobsen, J. Am. Chem. Soc.
2002, 124, 1307-1315; b) S. Dey, D. R. Powell, C. Hu, D. B. Berkowitz,
Angew. Chem. 2007, 119, 7140-7144; Angew. Chem. Int. Ed. 2007, 46,
7010-7014; c) Z. Wang, Y.-T. Cui, Z.-B. Xu, J. Qu, J. Org. Chem. 2008,
73, 2270-2274.
a) W.-H. Chen, M.-R. Lin, T.-S. Leu, S.-W. Du, Int. J. Hydrogen Energy
2011, 36, 11727-11737; b) R. Razzaq, C. Li, S. Zhang, Fuel 2013, 113,
287-299.
[8]
[9]
D.-Y. Lee, A. Elgowainy, Int. J. Hydrogen Energy 2018, 43, 20143-
20160.
a) M. Besson, P. Gallezot, C. Pinel, Chem. Rev. 2014, 114, 1827-1870;
b) S. H. Krishna, K. Huang, K. J. Barnett, J. He, C. T. Maravelias, J. A.
Dumesic, G. W. Huber, M. De bruyn, B. M. Weckhuysen, AIChE J.
2018, 64, 1910-1922; c) S. Gupta, M. I. Alam, T. S. Khan, M. A. Haider,
ACS Sustainable Chem. Eng. 2019, 7, 10165-10181.
[25] R. K. Saxena, P. Anand, S. Saran, J. Isar, L. Agarwal, Indian J.
Microbiol. 2010, 50, 2-11.
[26] a) H. Grꢀger, Adv. Synth. Catal. 2001, 343, 547-558; b) S. V. Ley, T. D.
Sheppard, R. M. Myers, M. S. Chorghade, Bull. Chem. Soc. Jpn. 2007,
80, 1451-1472; c) L. Vieweg, S. Reichau, R. Schobert, P. F. Leadlay, R.
D. Süssmuth. Nat. Prod. Rep. 2014, 31, 1554-1584.
[10] J. He, K. Huang, K. J. Barnett, S. H. Krishna, D. M. Alonso, Z. J.
Brentzel, S. P. Burt, T. Walker, W. F. Banholzer, C. T. Maravelias, I.
Hermans, J. A. Dumesic, G. W. Huber, Faraday Discuss. 2017, 202,
247-267.
[27] Optimization of the reaction conditions for the dehydrogenative
oxidation of 1,2-propanediol is shown in Table S2. The best result in
terms of the yield of sodium lactate was obtained by using 0.6
equivalents of Na2CO3 as a base. See the Supporting Imformation for
details.
[11] M. M. Ahsan, S. Sung, H. Jeon, M. D. Patil, T. Chung, H. Yun,
Catalysts 2018, 8, 4.
[12] a) W. Sabra, C. Groeger, A.-P. Zeng, Adv. Biochem. Eng. Biotechnol.
2016, 155, 165-197; b) Y. Zhang, D. Liu, Z. Chen, Biotechnol. Biofuels
2017, 10, 299.
[28] J. J. Mills, K. R. Robinson, T. E. Zehnder, J. G. Pierce, Angew. Chem.
2018, 130, 8818-8822; Angew. Chem. Int. Ed. 2018, 57, 8682-8686.
[29] N. S. Barta, G. W. Endres, A. M. Kornilov, K. M. Maxey, A. Uzieblo
(Cayman Chemical Company), US 20090124695A1, 2009.
[13] a) T. Fujii, T. Narikawa, F. Sumisa, A. Arisawa, K. Takeda, J. Kato,
Biosci. Biotechnol. Biochem. 2006, 70, 1379-1385; b) N. Fujita, F.
Sumisa, K. Shindo, H. Kabumoto, A. Arisawa, H. Ikenaga, N. Misawa,
Biosci. Biotechnol. Biochem. 2009, 73, 1825-1830.
[30] K. Abrahamsson, P. Andersson, J. Bergman, U. Bredberg, J. Brꢁnalt,
A.-C. Egnell, U. Eriksson, D. Gustafsson, K.-J. Hoffman, S. Nielsen, I.
Nilsson, S. Pehrsson, M. O. Polla, T. Skjaeret, M. Strimfors, C. Wern,
M. ꢂlwegꢁrd-Halvarsson, Y. ꢂrtengren, Med. Chem. Commun. 2016, 7,
272-281.
[14] a) Z.-L. Xiu, A.-P. Zeng, Appl. Microbiol. Biotechnol. 2008, 78, 917-926;
b) A. Burgard, M. J. Burk, R. Osterhout, S. V. Dien, H. Yim, Curr. Opin.
Biotechnol. 2016, 42, 118-125; c) A. Forte, A. Zucaro, R. Basosi, A.
Fierro, Materials 2016, 9, 563.
[31] a) D. B. Dess, J. C. Martin, J. Am. Chem. Soc. 1991, 113, 7277-7287;
b) K. C. Nicolaou, V. A. Adsool, C. R. H. Hale, Org. Lett. 2010, 12,
1552-1555; c) M. Shibuya, R. Doi, T. Shibuta, S.-i. Uesugi, Y. Iwabuchi,
Org. Lett. 2012, 14, 5006-5009; d) M. Shibuya, T. Shibuta, H. Fukuda,
Y. Iwabuchi, Org. Lett. 2012, 14, 5010-5013.
[15] a) E. Balaraman, E. Khaskin, G. Leitus, D. Milstein, Nat. Chem. 2013, 5,
122-125; b) Y. Sawama, K. Morita, T. Yamada, S. Nagata, Y. Yabe, Y.
Monguchi, H. Sajiki, Green Chem. 2014, 16, 3439-3443; c) J.-H. Choi,
L. E. Heim, M. Ahrens, M. H. G. Prechtl, Dalton Trans. 2014, 43,
17248-17254; d) J. Malineni, H. Keul, M. Mꢀller, Dalton Trans. 2015, 44,
17409-17414; e) Y. Sawama, K. Morita, S. Asai, M. Kozawa, S.
Tadokoro, J. Nakajima, Y. Monguchi, H. Sajiki, Adv. Synth. Catal. 2015,
357, 1205-1210; f) L. Zhang, D. H. Nguyen, G. Raffa, X. Trivelli, F.
Capet, S. Desset, S. Paul, F. Dumeignil, R. M. Gauvin, ChemSusChem
2016, 9, 1413-1423; g) X. Wang, C. Wang, Y. Liu, J. Xiao, Green Chem.
2016, 18, 4605-4610; h) Z. Dai, Q. Luo, X. Meng, R. Li, J. Zhang, T.
Peng, J. Organomet. Chem. 2017, 830, 11-18; i) A. Sarbajna, I. Dutta,
P. Daw, S. Dinda, S. M. W. Rahaman, A. Sarkar, J. K. Bera, ACS Catal.
2017, 7, 2786-2790; j) Z. Dai, Q. Luo, H.Jiang, Q. Luo, H. Li, J. Zhang,
[32] a) R. M. Painter, D. M. Pearson, R. M. Waymouth, Angew. Chem. 2010,
49, 9456-9459; Angew. Chem. Int. Ed. 2010, 122, 9646-9649; b) Y.
Ryabenkova, P. J. Miedziak, D. W. Knight, S. H. Taylor, G. J. Hutchings,
Tetrahedron 2014, 70, 6055-6058.
[33] a) M. L. Testa, R. Ciriminna, C. Hajji, E. Z. Garcia, M. Ciclosi, J. S.
Arques, M. Pagliaro, Adv. Synth. Catal. 2004, 346, 655-660; b) P.
Gancitano, R. Ciriminna, M. L. Testa, A. Fidalgo, L. M. Ilharco, M.
Pagliaro, Org. Biomol. Chem. 2005, 3, 2389-2392; c) K. Chinthapally, S.
Baskaran, Org. Biomol. Chem. 2014, 12, 4305-4309; d) K. Furukawa,
M. Shibuya, Y. Yamamoto, Org. Lett. 2015, 17, 2282-2285.
4
This article is protected by copyright. All rights reserved.