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Large Scale Utilization of Carbon Dioxide: From Its Reaction with Energy Rich Chemicals to (Co)-processing with Water to Afford Energy Rich Products. Opportunities and Barriers

  • Michele ArestaEmail author
  • Francesco Nocito
Chapter

Abstract

This chapter makes the analysis of the possible routes for large scale CO2 utilization (CCU). Processes that convert CO2 into chemicals, materials and fuels are discussed, as they are part of the strategy for reducing the CO2 emission into the atmosphere. Technical uses of CO2, which do not imply its chemical conversion, are discussed in Chap.  3, while mineralization and carbonation reactions for the production of inorganic materials are treated in Chap.  4. Here, the catalytic synthesis of organic products with a market close to, or higher than, 1 Mt/year is discussed, presenting the state of the art and barriers to full exploitation. Minor applications are summarized, without a detailed analysis as their contribution to CO2 reduction is low, even if they can favour the development of a sustainable chemical industry with reduction of the environmental impact. Energy products (C1 and Cn molecules) are discussed for some peculiar aspects in this chapter, as their catalytic production will be extensively presented in following chapters where the potential of using CO2 and water as source of fuels is analysed for its many possible applications setting actual limits and future perspectives. A comparison of Carbon Capture and Storage-CCS and CCU is made, highlighting the pros and cons of each technology.

References

  1. 1.
  2. 2.
    Aresta M (2010) Carbon dioxide as chemical feedstock. Wiley-WCHGoogle Scholar
  3. 3.
    Aresta M, Quaranta E, Tommasi I, Giannoccaro P, Ciccarese A (1995) Enzymatic versus chemical carbon dioxide utilization. Part I. The role of metal centres in carboxylation reactions. Gazz Chim Ital 125(11):509–538Google Scholar
  4. 4.
    (a) Baran T, Wojtyla S, Dibenedetto A, Aresta M, Macyk W (2015) Zinc sulfide functionalized with ruthenium nanoparticles for photocatalytic reduction of CO2. Appl Catal B Env 178:170–176. (b) Aresta M, Dibenedetto A, Baran T, Wojtyla S, Macyk W (2015) Solar energy utilization in the direct photocarboxylation of 2,3-dihydrofuran using CO2. Faraday Discuss 183:413–427. (c) Dibenedetto A, Zhang J, Trochowski M, Angelini A, Macyk W, Aresta M (2017) Photocatalytic carboxylation of CH bonds promoted by popped graphene oxide (PGO) either bare or loaded with CuO. J CO2 Utilz 20:97–104Google Scholar
  5. 5.
    Liang Y-F, Steinbock R, Yang L, Ackermann L (2018) Continuous visible light-photo-flow approach for manganese-catalyzed (het)arene C–H arylation. Angew Chem Int 57:10625–10629CrossRefGoogle Scholar
  6. 6.
    Helmenstine AM (2018) Heat of formation or standard enthalpy of formation table. Thought Co. https://www.thoughtco.com/common-compound-heat-of-formation-table-609253
  7. 7.
  8. 8.
    Abas N, Kalair A, Khan H (2015) Review of fossil fuels and future energy technologies. Futures 69:31–49CrossRefGoogle Scholar
  9. 9.
  10. 10.
    (a) Goto Y, Wang Q (2018) A particulate photocatalyst water-splitting panel for large-scale solar hydrogen generation. Joule. Accepted  https://doi.org/10.1016/j.joule.2017.12.009. (b) Pinaud BA, Benck JD, Seitz LC, Forman AJ, Chen Z, Deutsch TG, James BD, Baum KN, Baum GN, Ardo S (2013) Technical and economic feasibility of centralized facilities for solar hydrogen production via photocatalysis and photoelectrochemistry. Energy Env Sci 6(7):1983–2002CrossRefGoogle Scholar
  11. 11.
  12. 12.
    (a) Aresta M, Galatola M (2001) Life cycle analysis applied to the assessment of the environmental impact of alternative synthetic processes. J Cleaner Prod 7:181–193. (b) Aresta M, Caroppo A, Dibenedetto A, Narracci M (2002) Life cycle assessment (LCA) applied to the synthesis of methanol. Comparison of the use of syngas with the use of CO2 and dihydrogen produced from renewables. In: Maroto-Valer M (ed) Envrironmental challenges and greenhouse gas control for fossil fuel utilization in the 21st century. Kluwer Academic, Plenum Publishers, New York. (c) Artz J, Müller TE, Thenert K, Kleinekorte J, Meys R, Sternberg A, Bardow A, Leitner W (2018) Sustainable conversion of carbon dioxide: an integrated review of catalysis and life cycle assessment. Chem Rev 118(2):434–504Google Scholar
  13. 13.
    Aresta M, Quaranta E (1997) Carbon dioxide: a substitute for phosgene. Chem Tech 27(3):32–40Google Scholar
  14. 14.
  15. 15.
    Rupesh S, Muraleedharan C, Arun P (2016) Exergy and energy analyses of Syngas production from different biomasses through air-steaming gasification. Front Energy, pp 1–13Google Scholar
  16. 16.
  17. 17.
    Aresta M, Dibenedetto A, LN He (2012) Analysis of demand for captured CO2 and products from CO2 conversion. A report exclusively for members of the carbon dioxide capture and conversion CO2–CC programme of the catalyst group resources (TCGR)Google Scholar
  18. 18.
    (a) Aresta M, Dibenedetto A, Quaranta E (2016) Reaction mechanisms in carbon dioxide conversion. Springer. (b) Aresta M, Nobile CF, Albano VG, Forni E, Manassero M (1975) New nickel-carbon dioxide complex: synthesis, properties, and crystallographic characterization of (carbon dioxide)-bis(tricyclohexylphosphine)nickel. J Chem Soc Chem Comm 15:636–637Google Scholar
  19. 19.
    Aresta M, Nocito F, Dibenedetto A (2018) What catalysis can do for boosting carbon dioxide utilization. Adv Catal 62:49–110Google Scholar
  20. 20.
  21. 21.
    Tanaka R, Yamashita M, Nozaki K (2009) Catalytic hydrogenation of carbon dioxide using Ir(III)–Pincer complexes. J Am Chem Soc 131(40):14168–14169PubMedCrossRefGoogle Scholar
  22. 22.
    Wesselbaum S, Hintermaier U, Leitner W (2012) Continuous-flow hydrogenation of carbon dioxide to pure formic acid using an integrated scCO2 process with immobilized catalyst and base. Angew Chem Int Ed 51:8585–8588CrossRefGoogle Scholar
  23. 23.
    Moret S, Dyson P, Laurenczy G (2014) Direct synthesis of formic acid from carbon dioxide by hydrogenation in acidic media. Nat Commun 5:1–7CrossRefGoogle Scholar
  24. 24.
  25. 25.
  26. 26.
    Alvarez R, Carmona E, Galindo A, Gutierrez E, Marin JM, Monge A, Poveda ML, Ruiz C, Savariault JM (1989) Formation of carboxylate complexes from the reactions of CO2 with ethylene complexes of molybdenum and tungsten. X-ray and neutron diffraction studies. Organomet 8(10):2430–2439CrossRefGoogle Scholar
  27. 27.
    Aresta M, Pastore C, Giannoccaro P, Kovacs G, Dibenedetto A, Papai I (2007) Evidence for spontaneous release of acrylates from a transition-metal complex upon coupling ethene or propene with a carboxylic moiety or CO2. Chem Eur J 13(32):9028–9034PubMedCrossRefGoogle Scholar
  28. 28.
    Lejkowski ML, Lindner R, Kageyama T, Bodizs GE, Plessow PN, Mueller IM, Schaefer A, Rominger F, Hofmann P, Futter C, Schunck SA, Limbach M (2012) The first catalytic synthesis of an acrylate from CO2 and an alkene—a rational approach. Chem Eur J 18(44):14017–14025PubMedCrossRefGoogle Scholar
  29. 29.
    (a) Wang X, Wang H, Sun Y (2017) Synthesis of acrylic acid derivatives from CO2 and ethylene. Chem 3:211–228. (b) Li Y, Liu Z, Cheng R, Liu B (2018) Mechanistic aspects of acrylic acid formation from CO2–ethylene coupling over palladium- and Nickel-based catalysts. ChemCatChem 10(6):1420–1430Google Scholar
  30. 30.
    See for example Chapter 6 in Aresta M, Dibenedetto A, Quaranta E (2016) Reaction mechanisms for carbon dioxide conversion. SpringerGoogle Scholar
  31. 31.
    Aresta M, Dibenedetto A, Dutta A (2017) Energy issues in the utilization of CO2 in the synthesis of chemicals: the case of the direct carboxylation of alcohols to dialkyl-carbonates. Cat Today 281:345–351CrossRefGoogle Scholar
  32. 32.
    Aresta M, Dibenedetto A, Angelini A, Papai I (2015) Reaction mechanisms in the direct carboxylation of alcohols for the synthesis of acyclic carbonates. Top Catal 58(1):2–14CrossRefGoogle Scholar
  33. 33.
    Dibenedetto A, Aresta M, Angelini A, Etiraj J, Aresta BM (2012) Synthesis characterization and use of NbV/CeIV-mixed oxides in the direct carboxylation of ethanol by using pervaporation membranes for water removal. Chem A Eur J 18(33):10524–10534CrossRefGoogle Scholar
  34. 34.
    (a) See Ref. [30]. (b) Della Monica F, Buonerba A, Capacchione C (2018) Adv Synth Catal  https://doi.org/10.1002/adsc.201801281CrossRefGoogle Scholar
  35. 35.
    Aresta M, Dibenedetto A, Nocito F, Pastore C (2006) A study on the carboxylation of glycerol to glycerol carbonate with carbon dioxide: the role of the catalyst, solvent and reaction conditions. J Mol Cat 257(1–2):149–153CrossRefGoogle Scholar
  36. 36.
    (a) Aresta M, Quaranta E, Ciccarese A, (1987) Direct synthesis of 1,3-benzodioxol-2-one from styrene, dioxygen and carbon dioxide promoted by Rh(I). J Mol Cat 41:355–359. (b) Dibenedetto A, Aresta M, Distaso M, Pastore C, Venezia AM, Liu C-J, Zhang M (2008) High throughput experiment approach to the oxidation of propene to propene oxide with transition metal oxides as O-donors. Catal Today 137:44–51Google Scholar
  37. 37.
    Angelini A, Dibenedetto A, Curulla-Ferre D, Aresta M (2015) Synthesis of diethylcarbonate by ethanolysis of urea catalysed by heterogeneous mixed oxides. RSC Adv 5(107):88401–88408CrossRefGoogle Scholar
  38. 38.
    Wang M, Wang H, Zhao N, Sun Y (2007) High-yield synthesis of dimethyl carbonate from urea and methanol using a catalytic distillation process. Ind Eng Chem Res 46(9):2683–2687CrossRefGoogle Scholar
  39. 39.
    Aresta M, Ballivet-Tkatchenko D, Belli-Dell’Amico D, Bonnet MC, Boschi D, Calderazzo F, Faure R, Labella L, Marchetti F (2000) Isolation and structural determination of two derivatives of the elusive carbamic acid. RSC Chem Commun 13:1099–1100CrossRefGoogle Scholar
  40. 40.
    Aresta M, Dibenedetto A, Quaranta E (1998) Reaction of aromatic diamines with diphenylcarbonate catalyzed by phosphorous acids: a new clean synthetic route to mono- and dicarbamates. Tetrahedron 54(46):14145–14156CrossRefGoogle Scholar
  41. 41.
    Aresta M, Bosetti A, Quaranta E (1996) Procedimento per la produzione di carbammati aromatici. Ital Pat, Appl, p 002202Google Scholar
  42. 42.
    Aresta M, Dibenedetto A, Quaranta E (1999) Selective carbomethoxylation of aromatic diamines: with mixed carbonic acid diesters in the presence of phosphorous acids. Green Chem 1(5):237–242CrossRefGoogle Scholar
  43. 43.
    (a) Aresta M, Dibenedetto A (2002) Mixed anhydrides: key intermediates in carbamates forming processes of industrial interest. Chem A Eur J 8(3):685–690. (b) Aresta M, Dibenedetto A (2002) Development of environmentally friendly synthese: use of enzymes and biomimetic systems for the direct carboxylation of organic substrates. Rev Mol Biotechnol 90:113–128 Google Scholar
  44. 44.
  45. 45.
  46. 46.
  47. 47.
  48. 48.
  49. 49.
    Inui T, Phatanasri S, Matsuda H (1990) Highly selective synthesis of ethene from methanol on a novel nickel-silicoaluminophosphate catalyst. JCS Chem Comm 3:205–206CrossRefGoogle Scholar
  50. 50.
    Peng Y, Wu T, Sun L, Nsanzimana JMV, Fisher AC, Wang X (2017) Selective electrochemical reduction of CO2 to ethylene on nanopores-modified copper electrodes in aqueous solution. ACS Appl Mater Interfaces 9(38):32782–32789PubMedCrossRefGoogle Scholar
  51. 51.
    Tamura J, Ono A, Sugano Y, Huang C, Nishizawa H, Mikoshiba S (2015) Electrochemical reduction of CO2 to ethylene glycol on imidazolium ion-terminated self-assembly monolayer-modified Au electrodes in an aqueous solution. Phys Chem Chem Phys 17(39):26072–26078PubMedCrossRefGoogle Scholar
  52. 52.
  53. 53.
    Aresta M, Dibenedetto A (2019) Beyond fractionation in microalgae utilization. In: Pires J, Goncalves AL (eds) Bioenergy with carbon capture and storage. Elsevier, ISBN 9780128162293Google Scholar
  54. 54.
    Rabaey K, Rozendal RA (2010) Microbial electrosynthesis—revisiting the electrical route for microbial production. Nat Rev Microbiol 8(10):706–716PubMedCrossRefGoogle Scholar
  55. 55.
    Sugnaux M, Happe M, Cachelin CP, Gasperini A, Blatter M, Fischer F (2017) Cathode deposits favor methane generation in microbial electrolysis cell. Chem Eng J 324:228–236CrossRefGoogle Scholar
  56. 56.
    (a) Potter MC (1911) Electrical effects accompanying the decomposition of organic compounds. Proc R Soc B 84(571):260–276. (b) Santoro C, Arbizzani C, Erable B, Ieropoulos IJ (2017) Microbial fuel cells: from fundamentals to applications. A review. Power Sources 356:225–244Google Scholar
  57. 57.
    Tremblay PL, Zhang T (2015) Electrifying microbes for the production of chemicals. Front. Microbiol 6:201–205PubMedPubMedCentralGoogle Scholar
  58. 58.
    Xafenias N, Mapelli V (2014) Performance and bacterial enrichment of bioelectrochemical systems during methane and acetate production. Int J Hydrogen Energy 39(36):21864–21875CrossRefGoogle Scholar
  59. 59.
    El Mekawy A, Hegab HM, Mohanakrishna G, Bulut M, Pant D (2016) Technological advances in CO2 conversion electro-biorefinery: a step toward commercialization. Biores Technol 215:357–370CrossRefGoogle Scholar
  60. 60.
    de Bok FAM, Hagedoorn PL, Silva PJ, Hagen WR, Schiltz E, Fritsche K, Stams AJM (2003) Two W-containing formate dehydrogenase (CO2 reductases) involved in syntrophic propionate oxidation by Syntrophobacter fumaroxidans. Eur J Biochem 270:2476–2485PubMedCrossRefGoogle Scholar
  61. 61.
    Reda T, Plugge CM, Abram NJ, Hirst J (2008) Reversible interconversion of carbon dioxide and formate by an electroactive enzyme. Proc Natl Acad Sci USA 105(31):10654–10658PubMedCrossRefGoogle Scholar
  62. 62.
    Aresta M, Dibenedetto A, Baran T, Angelini A, Labuz P, Macyk W (2014) An integrated photocatalytic/enzymatic system for the reduction of CO2 to methanol in bioglycerol–water. Beilst J Org Chem 10:2556–2565CrossRefGoogle Scholar
  63. 63.
    Schlager S, Dibenedetto A, Aresta M, Apaydin DH, Dumitru LM, Neugebauer H, Sariciftci NS (2017) Biocatalytic and bioelectrocatalytic approaches for the reduction of carbon dioxide using enzymes. Energy Technol 5(6):812–821CrossRefGoogle Scholar
  64. 64.
    Aresta M, Dibenedetto A, Macyk W (2015) Hybrid (enzymatic and photocatalytic) systems for CO2—water coprocessing to afford energy-rich molecules. In: Rozhkova E, Katsuhiko A (eds) From molecules to materials, pathways to artificial photosynthesis. Springer, pp 149–169Google Scholar
  65. 65.
    Angelini A, Aresta M, Dibenedetto A, Baran T, Macyk W (2015) IP 0001419035, fotocatalizzatori per la riduzione nel visibile di NAD+ a NADH in un processo ibrido chemi-enzimatico di riduzione di CO2 a metanoloGoogle Scholar
  66. 66.
    Aresta M, Dibenedetto A, Quaranta E (2016) State of the art and perspectives in catalytic processes for CO2 conversion into chemicals and fuels: the distinctive contribution of chemical catalysis and biotechnology. J Catal 343:2–45CrossRefGoogle Scholar
  67. 67.
    Marxer D, Furler P, Tacacs M, Steinfeld A (2017) Solar thermochemical splitting of CO2 into separate streams of CO and O2 with high selectivity, stability, conversion, and efficiency. Energy Environ Sci 10(5):1142–1149CrossRefGoogle Scholar
  68. 68.
    (a) Bork A H, Kubicek M, Struzik M, Rupp J LM (2015) Perovskite La0.6Sr0.4Cr1−xCoxO3−δ solid solutions for solar-thermochemical fuel production: strategies to lower the operation temperature. J Mater Chem 3(30):15546–15557. (b) Rao CNR, Dey S (2015) Generation of H2 and CO by solar thermochemical splitting of H2O and CO2 by employing metal oxides. J Solid State Chem 242(2):107–115Google Scholar
  69. 69.
    Mostrou S, Buchel R, Pratsinis SE, van Bokhoven JA (2017) Improving the ceria-mediated water and carbon dioxide splitting through the addition of chromium. Appl Catal A Gen 537:40–49CrossRefGoogle Scholar
  70. 70.
    Amatore C, Savéant JM (1981) Mechanism and kinetic characteristics of the electrochemical reduction of carbon dioxide in media of low proton availability. J Am Chem Soc 103(17):5021–5023CrossRefGoogle Scholar
  71. 71.
    Hawecker J, Lehn JM, Ziessel R (1983) Efficient photochemical reduction of CO2 to CO by visible light irradiation of systems containing Re(bipy)(CO)3 X or Ru(bipy)32+–Co2+ combinations as homogeneous catalysts. J Chem Soc Chem Commun 9:536–538CrossRefGoogle Scholar
  72. 72.
    (a) Hori Y, Wakebe H, Tsukamoto T, Koga O (1994) Electrocatalytic process of CO selectivity in electrochemical reduction of CO2 at metal electrodes in aqueous media. Electrochim Acta 39(11–12):1833–1839. (b) Hori Y (2008) Electrochemical CO2 reduction on metal electrodes. In: Vayenas (ed) Modern aspects of electrochemistry, vol 42, 3rd edn., pp 89–189Google Scholar
  73. 73.
    Li Q, Fu J, Zhu W, Chen Z, Shen B, Wu L, Xi Z, Wang T, Lu G, Zhu JJ, Sun S (2017) Tuning Sn-catalysis for electrochemical reduction of CO2 to CO via the core/shell Cu/SnO2 structure. J Amer Chem Soc 139(12):4290–4293CrossRefGoogle Scholar
  74. 74.
    Schreier M, Héroguel F, Steier L, Ahmad S, Luterbacher JS, Mayer MT, Luo J, Graetzel M (2017) Solar conversion of CO2 to CO using earth-abundant electrocatalysts prepared by atomic layer modification of CuO. Nat Energy 2(7):17087–17096CrossRefGoogle Scholar
  75. 75.
    Zhang W, Hu Y, Ma L, Zhu G, Wang Y, Xue X, Chen R, Yang S, Jin Z (2017) Progress and perspective of electrocatalytic CO2 reduction for renewable carbonaceous fuels and chemicals. Adv Sci 5(1):1700275–1700279CrossRefGoogle Scholar
  76. 76.
  77. 77.
    Olah GA (2013) Towards oil independence through renewable methanol chemistry. Angew Chem Int Ed 52(1):104–107CrossRefGoogle Scholar
  78. 78.
    Tian P, Wei Y, Ye M, Liu Z (2015) Methanol to olefins (MTO): from fundamentals to commercialization. ACS Catal 5(3):1922–1938CrossRefGoogle Scholar
  79. 79.
    (a) Raudaskoski R, Turpeinen E, Lenkkeri R, Pongrácz E, Keiski RL (2009) Catalytic activation of CO2: use of secondary CO2 for the production of synthesis gas and for methanol synthesis over copper-based zirconia-containing catalysts. Catal Today 144(3–4):318-323. (b) Yang C, Ma Z, Zhao N, Wei W, Hu T, Sun Y (2006) Methanol synthesis from CO2-rich syngas over a ZrO2 doped CuZnO catalyst. Catal Today 115(1–4):222–227Google Scholar
  80. 80.
  81. 81.
    Ma J, Sun NN, Zhang XL, Zhao N, Mao FK, Wei W, Sun YH (2009) A short review of catalysis for CO2 conversion. Catal Today 148:221–223CrossRefGoogle Scholar
  82. 82.
  83. 83.
    Frusteri F, Cordaro M, Cannilla C, Bonura G (2015) Multifunctionality of Cu–ZnO–ZrO2/H-ZSM5 catalysts for the one-step CO2-to-DME hydrogenation reaction. Appl Catal B: Env 162:57–65CrossRefGoogle Scholar
  84. 84.
    Sabatier P, Senderens JB (1902) New synthesis of methane. J Chem Soc 82:333Google Scholar
  85. 85.
    Jürgensen L, Ehimen EA, Born J, Holm-Nielsen JB (2015) Dynamic biogas upgrading based on the Sabatier process: thermodynamic and dynamic process simulation. Bioresour Technol 178:323–329PubMedCrossRefGoogle Scholar
  86. 86.
    (a) Stangeland K, Kalai D, Li H, Yu Z (2017) CO2 methanation: the effect of catalysts and reaction conditions. Energy Proc 105:2022–2027. (b) Brooks KP, Hu J, Zhu H, Kee RJ (2007) Methanation of carbon dioxide by hydrogen reduction using the sabatier process in microchannel reactors. Chem Eng Sci 62:1161–1170. (c) Kirchner J, Katharina J, Henry A, Kureti LS (2018) Methanation of CO2 on iron based catalysts. Appl Catal B: Env 223:47-59. (d) Visconti, CG (2010) Reactor for exothermic or endothermic catalytic reaction WO2010/130399 & Visconti, CG (2014) Multi-structured reactor made of monolithic adjacent thermoconductive bodies for chemical processes with a high heat exchange WO2014/102350Google Scholar
  87. 87.
    Mattia D, Jones M D, O’Byrne J P, Griffiths OG, Owen RE, Sackville E, McManus M, Plucinski P (2015) Towards Carbon-Neutral CO2 Conversion to Hydrocarbons ChemSusChem 8(23):4064–4072Google Scholar
  88. 88.
    Gao P, Li S, Bu X, Sun Y (2017) Direct conversion of CO2 into liquid fuels with high selectivity over a bifunctional catalyst. Nat Chem 9(10):1019–1024PubMedCrossRefGoogle Scholar
  89. 89.
    (a) Satthawong R, Koizumi N, Song C, Prasassarakich P (2013) Bimetallic Fe–Co catalysts for CO2 hydrogenation to higher hydrocarbons. JCOU 3–4:102–106. (b) Visconti CG, Martinelli M, Falbo L, Infantes-Molina A, Lietti L, Forzatti P, Iaquaniello G, Palo E, Picutti B, Brignoli F (2017) CO2 hydrogenation to lower olefins on a high surface area K-promoted bulk Fe-catalyst. Appl Catal B 200:530–542Google Scholar
  90. 90.
    Emam EA (2015) Gas Flaring in industry: an overview. Pet Coal 57(5):532–555Google Scholar
  91. 91.
    Aresta M, Dibenedetto A, Quaranta E (2016) Reaction mechanisms in carbon dioxide conversion. Springer (Chapter 5)Google Scholar
  92. 92.
    (a) Pitter S, Dinjus E (1997) Phosphinoalkyl nitriles as hemilabile ligands: new aspects in the homogeneous catalytic coupling of CO2 and 1,3-butadiene. J Mol Catal A Chem 125:39–45. (b) Behr A, Henze H (2011) Use of carbon dioxide in chemical syntheses via a lactone intermediate. Green Chem 13:25–39Google Scholar
  93. 93.
    (a) Doring A, Jolly PM (1980) The palladium catalysed reaction of carbon dioxide with allene, Tetrahedron Lett, 21:3021–3024. (b) Aresta M, Ciccarese A, Quaranta E (1985) Head to head and head to tail coupling of allene and co-condensation with carbon dioxide promoted by 1,2-bis(diphenylphosphimo)ethane(η6-tetraphenylborate) rhodium. C1 Mol Chem 1:283-295. (c) North M (2011) Synthesis of b,g-unsaturated acids from allenes and carbon dioxide. Angew Chem Int Ed 48:4104–4105. (d) Aresta M, Dibenedetto A, Papai I, Schubert G (2002) Unprecedented formal [2 + 2] addition of allene to CO2 promoted by [RhCl(C2H4)(PiPr3)]2: direct synthesis of four membered lactone α-methylene-β-oxiethanone. The intermediacy of [RhH2Cl (PiPr3)]2: theoretical aspects and experiments. Inorg Chim Acta 334:294–300Google Scholar
  94. 94.
    (a) Hoberg H, Schaefer D, Buchart G (1982) Oxalanickelacyclopenten-drivate, ein neur typ vielseitig verwendbarer synthone. J Organomet Chem 228:C21–C24. (b) Albano P, Aresta M (1980) Some catalytic properties of Rh(diphos)(h6-BPh4). J Organomet Chem 190:243–246Google Scholar

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© Springer Nature Switzerland AG 2019

Authors and Affiliations

  1. 1.IC2R srl, Lab H124, TecnopolisValenzanoItaly
  2. 2.Department of Chemistry and CIRCCUniversity of BariBariItaly

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