Synthetic Transformations for the Valorization of Fatty Acid Derivatives

Abstract

Oleochemistry is a growing field from an industrial point of view, and it is fundamental to more sustainable chemical production that is less dependent on fossil sources. From this point of view, the development of selective and efficient synthetic transformations of triglycerides and fatty acids and esters is an active research field. This short review describes an overview of the most recent advances in the synthetic transformations of fatty acid derivatives into valuable chemicals.

1 Introduction

2 Reactions On the Ester Group of Fatty Acids and Esters

2.1 Synthesis of Free Carboxylic Acids

2.2 Synthesis of Carboxylic Esters

2.3 Reduction to Alcohols, Ethers, and Aldehydes

2.4 Synthesis of Nitrogenated Derivatives

3 Oxidation of Unsaturated Fatty Acids and Esters

3.1 Epoxidation and Reactions of Epoxides

3.2 Allylic Oxidation and Wacker Oxidation

3.3 Oxidative Cleavage

4 Addition Reactions of Unsaturated Fatty Acids and Esters

4.1 Hydrogenation and Hydroformylation

4.2 Cycloadditions and Related Reactions

4.3 Addition of Carboxylic Acids

4.4 Hydroalkylation

4.5 Thiol Radical Additions

5 Other Reactions of Unsaturated Fatty Acids and Esters

5.1 Cross-Metathesis

5.2 Isomerization

6 Conclusion and Outlook

Key words

triglycerides - vegetable oils - fatty acids - oleochemistry - catalysis - selectivity - monomers - chemicals from biomass

• References

• 1 Eissen M, Metzger JO, Schmidt E, Schneidewind U. Angew. Chem. Int. Ed. 2002; 41: 414
• 2 Anastas PT, Warner JC. Green Chemistry: Theory and Practice . Oxford University Press; Oxford: 1998
• 3 Besson M, Gallezot P, Pinel C. Chem. Rev. 2014; 114: 1827
• 4 OECD-FAO Agricultural Outlook 2016–2025. OECD Publishing; Paris: 2016. http://dx.doi.org/10.1787/agr_outlook-2016-en
• 5 Hara M, Nakajima K, Kamata K. Sci. Technol. Adv. Mater. 2015; 16: 34903
• 6 Gallezot P. Chem. Soc. Rev. 2012; 41: 1538
• 7 Corma A, Iborra S, Velty A. Chem. Rev. 2007; 107: 2411
• 8 Biermann U, Friedt W, Lang S, Lühs W, Machmüller G, Metzger JO, Klass MR. G, Schäfer HJ, Schneider MP. Angew. Chem. Int. Ed. 2000; 39: 2206
• 9 Baumann H, Bühler M, Fochem H, Hirsinger F, Zoebelein H, Falbe J. Angew. Chem. Int. Ed. 1988; 27: 41
• 10 Zhou C.-HC, Beltramini JN, Fan Y.-X, Lu GQ. M. Chem. Soc. Rev. 2008; 37: 527
• 11 Katryniok B, Kimura H, Skrzyńska E, Girardon J.-S, Fongarland P, Capron M, Ducoulombier R, Mimura N, Paul S, Dumeignil F. Green Chem. 2011; 13: 1960
• 12 García JI, García-Marín H, Pires E. Green Chem. 2014; 16: 1007
• 13 Behr A, Eilting J, Irawadi K, Leschinski J, Lindner F. Green Chem. 2008; 10: 13
• 14 Metzger JO. Eur. J. Lipid Sci. Technol. 2009; 111: 865
• 15 Biermann U, Bornscheuer U, Meier MA. R, Metzger JO, Schäfer HJ. Angew. Chem. Int. Ed. 2011; 50: 3854
• 16 Furst MR. L, Le Goff R, Quinzler D, Mecking S, Botting CH, Cole-Hamilton DJ. Green Chem. 2012; 14: 472
• 17 Koshikari Y, Sakakura A, Ishihara K. Org. Lett. 2012; 14: 3194
• 18 Haulotte E, Laurent P, Braekman J.-C. Eur. J. Org. Chem. 2012; 1907
• 19 Leggio A, De Marco R, Perri F, Spinella M, Liguori A. Eur. J. Org. Chem. 2012; 114
• 20a Pawar BV, Lokhande PD. Synth. Commun. 2009; 39: 2445
• 20b Lipshutz BH, Ghorai S, Leong WW. Y. J. Org. Chem. 2009; 74: 2854
• 21 Stevens C, Verhé R. Renewable Bioresources: Scope and Modification for Non-Food Applications. John Wiley & Sons; Chichester: 2004
• 22 Pacheco BS, Nunes CF. P, Rockembach CT, Bertelli P, Mesko MF, Roesch-Ely M, Moura S, Pereira CM. P. Green Chem. Lett. Rev. 2014; 7: 265
• 23 Sakakura A, Koshikari Y, Ishihara K. Tetrahedron Lett. 2008; 49: 5017
• 24 Jabbari H, Khalafy J, Najafi Moghadam P. Iran. Chem. Commun. 2015; 3: 244
• 25 Chakraborti AK, Singh B, Chankeshwara SV, Patel AR. J. Org. Chem. 2009; 74: 5967
• 26 Fabian L, Gómez M, Caturelli Kuran JA, Moltrasio G, Moglioni A. Synth. Commun. 2014; 44: 2386
• 27 Ferreira AB, Cardoso AL, da Silva MJ. Catal. Lett. 2013; 143: 1240
• 28 Sunitha S, Kanjilal S, Reddy PS, Prasad RB. N. Tetrahedron Lett. 2007; 48: 6962
• 29 Socha AM, Sello JK. Org. Biomol. Chem. 2010; 8: 4753
• 30 Mamidi N, Manna D. J. Org. Chem. 2013; 78: 2386
• 31 Reddy YS, Kaki SS, Rao BB, Jain N, Vijayalakshmi P. J. Oleo Sci. 2016; 65: 81
• 32 Zheng Y, Zheng M, Ma Z, Xin B, Guo R, Xu X In Polar Lipids . Elsevier; Amsterdam: 2015: 215-243
• 33 Nitbani FO, Jumina, Siswanta D, Solikhah EN. Int. J. Pharm. Sci. Rev. Res. 2015; 35: 126
• 34 Quinzler D, Mecking S. Angew. Chem. Int. Ed. 2010; 49: 4306
• 35 Zhang J, Gao X, Zhang C, Ma J, Zhao D. Synth. Commun. 2009; 39: 1640
• 36 Pulle JS, Sagar AD, Reddy SM, Yadav MV. Chem. Sin. 2015; 6: 104; http://pelagiaresearchlibrary.com/der-chemica-sinica/index.html
• 37 Xu Y, Wei Y. Synth. Commun. 2010; 40: 3423
• 38 Pischl MC, Weise CF, Haseloff S, Müller M.-A, Pfaltz A, Schneider C. Chem. Eur. J. 2014; 20: 17360
• 39 Sakai N, Kawana K, Ikeda R, Nakaike Y, Konakahara T. Eur. J. Org. Chem. 2011; 3178
• 40 Pehlivan L, Métay E, Laval S, Dayoub W, Delbrayelle D, Mignani G, Lemaire M. Eur. J. Org. Chem. 2011; 7400
• 41 Zhang Y.-J, Dayoub W, Chen G.-R, Lemaire M. Tetrahedron 2012; 68: 7400
• 42 Tan X, Wang Y, Liu Y, Wang F, Shi L, Lee K.-H, Lin Z, Lv H, Zhang X. Org. Lett. 2015; 17: 454
• 43 Cui X, Li Y, Topf C, Junge K, Beller M. Angew. Chem. Int. Ed. 2015; 54: 10596
• 44 Korstanje TJ, van der Vlugt JI, Elsevier CJ, de Bruin B. Science (Washington, D. C.) 2015; 350: 298
• 45 Werkmeister S, Junge K, Wendt B, Alberico E, Jiao H, Baumann W, Junge H, Gallou F, Beller M. Angew. Chem. Int. Ed. 2014; 53: 8722
• 46 Spasyuk D, Vicent C, Gusev DG. J. Am. Chem. Soc. 2015; 137: 3743
• 47 Li W, Xie J.-H, Yuan M.-L, Zhou Q.-L. Green Chem. 2014; 16: 4081
• 48 Spasyuk D, Smith S, Gusev DG. Angew. Chem. Int. Ed. 2012; 51: 2772
• 49 Ishmuratov GY, Vydrina VA, Yakovleva MP, Nasibullina GV, Nazarov IS, Muslukhov RR, Tolstikov AG. Russ. J. Org. Chem. 2012; 48: 1509
• 50 Walther G, Deutsch J, Martin A, Baumann F.-E, Fridag D, Franke R, Köckritz A. ChemSusChem 2011; 4: 1052
• 51 Sutter M, Dayoub W, Métay E, Raoul Y, Lemaire M. Green Chem. 2013; 15: 786
• 52 Biermann U, Metzger JO. ChemSusChem 2014; 7: 644
• 53 Fujihara T, Cong C, Iwai T, Terao J, Tsuji Y. Synlett 2012; 23: 2389
• 54 Fujihara T, Cong C, Terao J, Tsuji Y. Adv. Synth. Catal. 2013; 355: 3420
• 55 Cheng C, Brookhart M. Angew. Chem. Int. Ed. 2012; 51: 9422
• 56 Zheng J, Chevance S, Darcel C, Sortais J.-B. Chem. Commun. 2013; 49: 10010
• 57 Biswas A, Sharma BK, Willett JL, Erhan SZ, Cheng HN. Energy Environ. Sci. 2008; 1: 639
• 58 Theodorou V, Karkatsoulis A, Kinigopoupou M, Ragoussis V, Skobridis K. ARKIVOC 2009; (xi): 277
• 59 Mallia VA, George M, Blair DL, Weiss RG. Langmuir 2009; 25: 8615
• 60 Awasthi NP, Singh RP. Eur. J. Lipid Sci. Technol. 2009; 111: 202
• 61 Awasthi NP, Singh RP. J. Oleo Sci. 2007; 56: 507
• 62 Terada Y, Ieda N, Komura K, Sugi Y. Synthesis 2008; 2318
• 63 Komura K, Nakano Y, Koketsu M. Green Chem. 2011; 13: 828
• 64 Yildirim A. Monatsh. Chem. 2015; 146: 947
• 65 Calcio Gaudino E, Carnaroglio D, Nunes MA. G, Schmidt L, Flores EM. M, Deiana C, Sakhno Y, Martra G, Cravotto G. Catal. Sci. Technol. 2014; 4: 1395
• 66 Bundesmann MW, Coffey SB, Wright SW. Tetrahedron Lett. 2010; 51: 3879
• 67 Tinsley JF, Jahnke JP, Adamson DH, Guo X, Amin D, Kriegel R, Saini R, Dettman HD, Prud’home RK. Energy Fuels 2009; 23: 2065
• 68 Li B, Sortais J.-B, Darcel C. Chem. Commun. 2013; 49: 3691
• 69 Laval S, Dayoub W, Pehlivan L, Métay E, Favre-Réguillon A, Delbrayelle D, Mignani G, Lemaire M. Tetrahedron Lett. 2011; 52: 4072
• 70 Xiao K.-J, Wang A.-E, Huang P.-Q. Angew. Chem. Int. Ed. 2012; 51: 8314
• 71 Zhang W, Haskins CW, Yang Y, Dai M. Org. Biomol. Chem. 2014; 12: 9109
• 72 Kangani CO, Day BW, Kelley DE. Tetrahedron Lett. 2007; 48: 5933
• 73 Suzuki Y, Moriyama K, Togo H. Tetrahedron 2011; 67: 7956
• 74 Miyagi K, Moriyama K, Togo H. Eur. J. Org. Chem. 2013; 5886
• 75 Wojtkielewicz A, Łotowski Z, Morzycki J. Synlett 2015; 26: 2288
• 76 Köckritz A, Martin A. Eur. J. Lipid Sci. Technol. 2008; 110: 812
• 77 Yang D, Hou M, Ning H, Zhang J, Ma J, Yang G, Han B. Green Chem. 2013; 15: 2261
• 78 Guidotti M, Psaro R, Ravasio N, Sgobba M, Gianotti E, Grinberg S. Catal. Lett. 2007; 122: 53
• 79 Sankaranarayanan S, Sharma A, Srinivasan K. Catal. Sci. Technol. 2015; 5: 1187
• 80 Khatri PK, Aila M, Porwal J, Kaul S, Jain SL. New J. Chem. 2015; 39: 5960
• 81 Neves P, Amarante TR, Valente AA, Pillinger M, Gonçalves IS. Catal. Lett. 2016; 146: 841
• 82 Davletbakova AM, Baibulatova NZ, Dokichev VA, Muslukhov RR, Yunusova SG, Yunusov MS. Russ. J. Org. Chem. 2001; 37: 1220
• 83 Du G, Tekin A, Hammond EG, Wood LK. J. Am. Oil Chem. Soc. 2016; 81: 477
• 84 Poli E, Clacens J.-M, Barrault J, Pouilloux Y. Catal. Today 2009; 140: 19
• 85 De Torres M, Arends IW. C. E, Mayoral JA, Pires E, Jimenez-Oses G. Appl. Catal. A 2012; 425: 91
• 86 Guidotti M, Gavrilova E, Galarneau A, Coq B, Psaro R, Ravasio N. Green Chem. 2011; 13: 1806
• 87 Sepulveda J, Teixeira S, Schuchardt U. Appl. Catal. A 2007; 318: 213
• 88 Poli E, Bion N, Barrault J, Casciato S, Dubois V, Pouilloux Y, Clacens J.-M. Catal. Today 2010; 157: 371
• 89 Poli E, De Sousa R, Jérome F, Pouilloux Y, Clacens J.-M. Catal. Sci. Technol. 2012; 2: 910
• 90 Leng Y, Zhao J, Jiang P, Wang J. ACS Appl. Mater. Interfaces 2014; 6: 5947
• 91 Milchert E, Malarczyk K, Kłos M. Molecules 2015; 20: 21481
• 92 Rubinstein A, Carmeli R, Neumann R. Chem. Commun. 2014; 50: 13247
• 93 Scotti N, Ravasio N, Psaro R, Evangelisti C, Dworakowska S, Bogdal D, Zaccheria F. Catal. Commun. 2015; 64: 80
• 94 Narine SS, Yue J, Kong X. J. Am. Oil Chem. Soc. 2007; 84: 173
• 95 Palaskar DV, Boyer A, Cloutet E, Le Meins J.-F, Gadenne B, Alfos C, Farcet C, Cramail H. J. Polym. Sci., Part A: Polym. Chem. 2012; 50: 1766
• 96 Fatiadi AJ. Synthesis 1987; 85
• 97 Schroeder M. Chem. Rev. 1980; 80: 187
• 98 Akashi K, Palermo RE, Sharpless KB. J. Org. Chem. 1978; 43: 2063
• 99 van den Broek BA. M. W, Becker R, Kössl F, Delville MM. E, Nieuwland PJ, Koch K, Rutjes FP. J. T. ChemSusChem 2012; 5: 289
• 100 Piazza GJ, Nuñez A, Foglia TA. J. Am. Oil Chem. Soc. 2003; 80: 901
• 101 Usui Y, Sato K, Tanaka M. Angew. Chem. Int. Ed. 2003; 42: 5623
• 102 Dailey OD, Prevost NT, Strahan GD. J. Am. Oil Chem. Soc. 2009; 86: 1101
• 103 Moser BR, Erhan SZ. Eur. J. Lipid Sci. Technol. 2007; 109: 206
• 104 Campanella A, Rustoy E, Baldessari A, Baltanás MA. Bioresour. Technol. 2010; 101: 245
• 105 Ahn B.-JK, Kraft S, Sun XS. J. Agric. Food Chem. 2012; 60: 2179
• 106 Somidi AK. R, Sharma RV, Dalai AK. J. Am. Oil Chem. Soc. 2015; 92: 1365
• 107 Sharma RV, Dalai AK. Appl. Catal. B 2013; 142–143: 604
• 108 Somidi AK. R, Das U, Dalai AK. Chem. Eng. J. 2016; 293: 259
• 109 Sammaiah A, Padmaja KV, Prasad RB. N. J. Agric. Food Chem. 2014; 62: 4652
• 110 Harry-O’kuru RE. Lipids 2005; 40: 1179
• 111 Harry-O’kuru RE, Tisserat B, Gordon SH, Gravett A. J. Agric. Food Chem. 2015; 63: 6588
• 112 Bailosky LC, Bender LM, Bode D, Choudhery RA, Craun GP, Gardner KJ, Michalski CR, Rademacher JT, Stella GJ, Telford DJ. Prog. Org. Coat. 2013; 76: 1712
• 113 Gandini A, Lacerda TM, Carvalho AJ. F. Green Chem. 2013; 15: 1514
• 114 Zhang L, Luo Y, Hou Z, He Z, Eli W. J. Am. Oil Chem. Soc. 2013; 91: 143
• 115 Singh S, Kamboj R. Ind. Eng. Chem. Res. 2010; 49: 3106
• 116 De Torres M, Jiménez-Osés G, Mayoral JA, Pires E. Bioresour. Technol. 2011; 102: 2590
• 117 Gallo JM. R, Teixeira S, Schuchardt U. Appl. Catal. A 2006; 311: 199
• 118 Schäffner B, Blug M, Kruse D, Polyakov M, Köckritz A, Martin A, Rajagopalan P, Bentrup U, Brückner A, Jung S, Agar D, Rüngeler B, Pfennig A, Müller K, Arlt W, Woldt B, Graß M, Buchholz S. ChemSusChem 2014; 7: 1133
• 119 Langanke J, Greiner L, Leitner W. Green Chem. 2013; 15: 1173
• 120 Tenhumberg N, Büttner H, Schäffner B, Kruse D, Blumenstein M, Werner T. Green Chem. 2016; 18: 3775
• 121 Narra N, Rachapudi BN. P, Vemulapalli SP. B, Korlipara PV. RSC Adv. 2016; 6: 25703
• 122 Zobel M, Schäfer HJ. Eur. J. Lipid Sci. Technol. 2016; 118: 80
• 123 Morandi B, Wickens ZK, Grubbs RH. Angew. Chem. Int. Ed. 2013; 52: 2944
• 124 Winkler M, Meier MA. R. Green Chem. 2014; 16: 1784
• 125 Hermans I, Janssen K, Moens B, Philippaerts A, Van Berlo B, Peeters J, Jacobs PA, Sels BF. Adv. Synth. Catal. 2007; 349: 1604
• 126 Ishmuratov GY, Legostaeva YV, Botsman LP, Nasibullina GV, Garifullina LR, Muslukhov RR, Tolstikov GA. Russ. J. Org. Chem. 2012; 48: 1272
• 127 Ishmuratov GY, Legostaeva YV, Garifullina LR, Botsman LP, Idrisova ZI, Muslukhov RR, Ishmuratova NM, Tolstikov GA. Russ. J. Org. Chem. 2013; 49: 1409
• 128 Dapurkar SE, Kawanami H, Yokoyama T, Ikushima Y. Top. Catal. 2009; 52: 707
• 129 Spannring P, Bruijnincx PC. A, Weckhuysen BM, Klein Gebbink RJ. M. Catal. Sci. Technol. 2014; 4: 2182
• 130 Kadyrov R, Hackenberger D. Top. Catal. 2014; 57: 1366
• 131 Deruer E, Duguet N, Lemaire M. ChemSusChem 2015; 8: 2481
• 132 Philippaerts A, Jacobs PA, Sels BF. Angew. Chem. Int. Ed. 2013; 52: 5220
• 133 Zaccheria F, Psaro R, Ravasio N. Green Chem. 2009; 11: 462
• 134 Zaccheria F, Psaro R, Ravasio N, Bondioli P. Eur. J. Lipid Sci. Technol. 2012; 114: 24
• 135 Pecchia P, Galasso I, Mapelli S, Bondioli P, Zaccheria F, Ravasio N. Ind. Crops Prod. 2013; 51: 306
• 136 Studentschnig AF. H, Schober S, Mittelbach M. Energy Fuels 2015; 29: 3776
• 137 Bouriazos A, Vasiliou C, Tsichla A. Catal. Today 2015; 247: 20
• 138 Vanbésien T, Monflier E, Hapiot F. Eur. J. Lipid Sci. Technol. 2016; 118: 26
• 139 Boulanger J, Ponchel A, Bricout H, Hapiot F, Monflier E. Eur. J. Lipid Sci. Technol. 2012; 114: 1439
• 140 Benetskiy E, Lühr S, Vilches-Herrera M, Selent D, Jiao H, Domke L, Dyballa K, Franke R, Börner A. ACS Catal. 2014; 4: 2130
• 141 Behr A, Seidensticker T, Vorholt AJ. Eur. J. Lipid Sci. Technol. 2014; 116: 477
• 142 Biermann U, Butte W, Eren T, Haase D, Metzger JO. Eur. J. Org. Chem. 2007; 3859
• 143 Candy L, Vaca-Garcia C, Borredon E. J. Am. Oil Chem. Soc. 2005; 82: 271
• 144 Loutelier-Bourhis C, Zovi O, Lecamp L, Bunel C, Hubert-Roux M, Lange CM. Rapid Commun. Mass Spectrom. 2012; 26: 1265
• 145 Resch V, Hanefeld U. Catal. Sci. Technol. 2015; 5: 1385
• 146 Cermak SC, Isbell TA. Ind. Crops Prod. 2009; 29: 205
• 147 Biermann U, Metzger JO. J. Am. Chem. Soc. 2004; 126: 10319
• 148 Erb B, Dierker M, Ohlmann DM, Gooßen LJ. Eur. J. Lipid Sci. Technol. 2016; 118: 111
• 149 Türünç O, Meier MA. R. Eur. J. Lipid Sci. Technol. 2013; 115: 41
• 150 Desroches M, Caillol S, Lapinte V, Auvergne R, Boutevin B. Macromolecules 2011; 44: 2489
• 151 Rybak A, Fokou PA, Meier MA. R. Eur. J. Lipid Sci. Technol. 2008; 110: 797
• 152 Kajetanowicz A, Sytniczuk A, Grela K. Green Chem. 2014; 16: 1579
• 153 Miao X, Malacea R, Fischmeister C, Bruneau C, Dixneuf PH. Green Chem. 2011; 13: 2911
• 154 Vilela C, Silvestre AJ. D, Meier MA. R. Macromol. Chem. Phys. 2012; 213: 2205
• 155 Mutlu H, Hofsäß R, Montenegro RE, Meier MA. R. RSC Adv. 2013; 3: 4927
• 156 Peng Y, Totsingan F, Meier MA. R, Steinmann M, Wurm F, Koh A, Gross RA. Eur. J. Lipid Sci. Technol. 2015; 117: 217
• 157 Ameh Abel G, Oliver Nguyen K, Viamajala S, Varanasi S, Yamamoto K. RSC Adv. 2014; 4: 55622
• 158 Yapa Mudiyanselage A, Viamajala S, Varanasi S, Yamamoto K. ACS Sustainable Chem. Eng. 2014; 2: 2831
• 159 Patel J, Elaridi J, Jackson WR, Robinson AJ, Serelis AK, Such C. Chem. Commun. 2005; 5546
• 160 Patel J, Mujcinovic S, Jackson WR, Robinson AJ, Serelis AK, Such C. Green Chem. 2006; 8: 450
• 161 Philippaerts A, Goossens S, Jacobs PA, Sels BF. ChemSusChem 2011; 4: 684
• 162 Salamon R, Vargáné-Visi É, András CD, Kiss ZC, Csapó J. Acta Aliment. 2015; 229
• 163 Berdeaux O, Voinot L, Angioni E, Juanéda P, Sébédio JL. J. Am. Oil Chem. Soc. 1998; 75: 1749
• 164 Consorti CS, Aydos GL. P, Ebeling G, Dupont J. Appl. Catal. A 2009; 371: 114
• 165 Chen J, Chen X, Zheng Y, Li Q. RSC Adv. 2015; 5: 20248
• 166 Yan J, Yang J, Yang R, He H, Liu Q, Lin H. J. Serb. Chem. Soc. 2016; 81: 141
• 167 Goldbach V, Roesle P, Mecking S. ACS Catal. 2015; 5: 5951
• 168 Zhu Y, Jang SH. A, Tham YH, Algin OB, Maguire JA, Hosmane NS. Organometallics 2012; 31: 2589
• 169 Pandey S, Chikkali SH. ChemCatChem 2015; 7: 3468
• 170 Christl JT, Roesle P, Stempfle F, Wucher P, Göttker-Schnetmann I, Müller G, Mecking S. Chem. Eur. J. 2013; 19: 17131