Gas phase dehydration of 3-hydroxybutanone on orthophosphate catalysts for bio-based production of butenone for a sustainable industrial route to vitamin A

M. Huchede; C. Lorentz; L. Cardenas; D. Morvan; V. Bellière-Baca; J.M.M. Millet

Journal of Industrial and Engineering Chemistry, Vol.88, 178-185, August, 2020

DOI10.1016/j.jiec.2020.04.011 Export Citation

Gas phase dehydration of 3-hydroxybutanone on orthophosphate catalysts for bio-based production of butenone for a sustainable industrial route to vitamin A

M. Huchede, C. Lorentz, L. Cardenas, D. Morvan¹, V. Bellière-Baca¹, and J.M.M. Millet^†

Univ Lyon, Université Claude Bernard Lyon 1, CNRS, IRCELYON - UMR 5256, 2 Av. Albert Einstein, 69626 Villeurbanne, France
¹Adisseo, Antony Parc 2, 10 Place Général de Gaulle, 92160 Antony, France

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We report on the catalytic dehydration of 3-hydroxybutanone to butenone (but-3-en-2-one or methyl vinyl ketone), which could become a key step in a new bio-based process for the production of vitamin A. The gas-phase dehydration reaction has been studied with various trivalent orthophosphates under atmospheric pressure, at temperatures ranging between 250 and 350 °C. Although FePO4, CePO4, YPO4 and BPO4 are found to be either poorly active, or poorly selective to butanone, the other rare-earth phosphates tested in this study allowed higher butanone yields to be obtained than has been previously reported. We show that the catalytic properties of these compounds depend on the nature of the rare-earth element. The most promising results are obtained with LaPO4, which is characterized by a 93% selectivity to butenone at 92% conversion. The catalytic activity and selectivity of the most efficient catalysts are discussed in terms of their surface acidity and basicity.

Keywords:Acetoin;3-hydroxybutanone;Dehydration;Metal oxides catalyst;Orthophosphates;Rare-earth;Butenone;3-buten-2-one;Methyl vinyl ketone;Platform molecule

[References]

Siegel H, Eggersdorfer M, “Ketones”, Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
Cymerman J, Heilbron IM, Johnson AW, Jones ERH, J. Chem. Soc., 141 (1944).
Trosta BM, Weiss AH, Adv. Synth. Catal., 351, 963 (2009)
Ai M, J. Catal., 106, 73 (1987)
Carreno NLV, Fajardo HV, Maciel AP, Valentini A, Pontes FM, Probst LFD, Leite ER, Longo E, J. Mol. Catal. A-Chem., 207(2), 91 (2004)
Ember G, (Hoffmann-La Roche Inc), US3890392, 1975.
Blicke FF, Burckhalter JH, J. Am. Chem. Soc., 64, 451 (1942)
Marliere P, Anissimova M, Allard M(Scientist of Fortune), WO2015000981, 2015.
Dumesic JA, West RM(Wisconsin Alumni Research Foundation), US 7960592, 2011.
Zhu C, Shen T, Liu D, Wu J, Chen Y, Wang L, Guo K, Ying H, Ouyanga P, Green Chem., 18, 2165 (2016)
Hays T, Hager GF, Engelmann HM, Spurlin HM, J. Am. Chem. Soc., 73, 5369 (1951)
Long L, Ying Z, Shujun Z, Han X, Huabin L, (Nankai University), CN 102633611A, 2014.
Hale WJ, Midland M, Leland A(National Agrol Company) US2371577, 1945.
Wang R, Jiang H, Gong H, Zhang J, Mater. Res. Bull., 47(8), 2108 (2012)
Deleplanque J, Dubois JL, Devaux JF, Ueda W, Catal. Today, 157(1-4), 351 (2010)
Ramesh K, Goh YLE, Gwie CG, Jie C, White TJ, Borgna A, J. Porous Mat., 19, 423 (2012)
Ramesh K, Zheng JE, Ling EGY, Han YF, Borgna A, J. Phys. Chem. C, 113, 16530 (2009)
Nguyen TTN, Ruaux V, Massin L, Lorenzt C, Afanasiev P, Mauge F, Belliere-Baca V, Rey P, Millet JMM, Appl. Catal. B: Environ., 166-167, 432 (2015)
Nguyen TTN, Ruaux V, Mauge F, Belliere-Baca V, Rey P, Millet JMM, Appl. Catal. A: Gen., 504, 4 (2015)
Blanco E, Delichere P, Millet JMM, Loridant S, Catal. Today, 226, 185 (2014)
Millet JMM, Virely C, Forissier M, Bussiere P, Vedrine JC, Hyperfine Interact., 46, 619 (1989)
Lauriol-Garbay P, Millet JMM, Loridant S, Belliere-Baca V, Rey P, J. Catal., 280(1), 68 (2011)
Nguyen NTT, Matei-Rutkovska F, Huchede M, Jaillardon K, Qingyi G, Michel C, Millet JMM, Catal. Today, 323, 62 (2019)
Settle E, Berstis L, Rorrer NA, Roman-Leshkov Y, Beckham GT, Richards RM, Vardon DR, Green Chem., 19, 3468 (2017)
Glorieux B, Matecki M, Fayon F, Coutures JP, Palau S, Douy A, Peraudeau G, J. Nucl. Mater., 326, 156 (2004)
Terra O, Clavier N, Dacheux N, Podor R, New J. Chem., 27, 957 (2003)
Stranz M, Gut W, Fiedorow R, Ryszard Prace Naukowe Akademii Ekonomicznej, 338, 199 (1986).
Calzolari L, Cavani F, Monti T, C. R. Acad. Sci. Paris, Serie IIc, Chimie/Chemistry, 3, 533 (2000).
Clearfield A, Inorganic Ion Exchange Materials, CRC Press, Boca Raton, FL,1982.
Tanabe K, Misono M, Ono Y, Hattori H, Stud. Surf. Sci. Catal., 51, 260 (1990)
Galtayries A, Sporken R, Riga J, Blanchard G, Caudano R, J. Electron Spectrosc. Relat. Phenom., 88-91, 951 (1998)
Lopez JM, Gilbank AL, Garcia T, Solsona B, Agouram S, Torrente-Murciano L, Appl. Catal. B: Environ., 174-175, 403 (2015)
Sato S, Takahashi R, Sodesawa T, Honda NT, J. Mol. Catal. A-Chem., 221(1-2), 177 (2004)

[1] Siegel H, Eggersdorfer M, “Ketones”, Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.

[2] Cymerman J, Heilbron IM, Johnson AW, Jones ERH, J. Chem. Soc., 141 (1944).

[3] Trosta BM, Weiss AH, Adv. Synth. Catal., 351, 963 (2009)

[4] Ai M, J. Catal., 106, 73 (1987)

[5] Carreno NLV, Fajardo HV, Maciel AP, Valentini A, Pontes FM, Probst LFD, Leite ER, Longo E, J. Mol. Catal. A-Chem., 207(2), 91 (2004)

[6] Ember G, (Hoffmann-La Roche Inc), US3890392, 1975.

[7] Blicke FF, Burckhalter JH, J. Am. Chem. Soc., 64, 451 (1942)

[8] Marliere P, Anissimova M, Allard M(Scientist of Fortune), WO2015000981, 2015.

[9] Dumesic JA, West RM(Wisconsin Alumni Research Foundation), US 7960592, 2011.

[10] Zhu C, Shen T, Liu D, Wu J, Chen Y, Wang L, Guo K, Ying H, Ouyanga P, Green Chem., 18, 2165 (2016)

[11] Hays T, Hager GF, Engelmann HM, Spurlin HM, J. Am. Chem. Soc., 73, 5369 (1951)

[12] Long L, Ying Z, Shujun Z, Han X, Huabin L, (Nankai University), CN 102633611A, 2014.

[13] Hale WJ, Midland M, Leland A(National Agrol Company) US2371577, 1945.

[14] Wang R, Jiang H, Gong H, Zhang J, Mater. Res. Bull., 47(8), 2108 (2012)

[15] Deleplanque J, Dubois JL, Devaux JF, Ueda W, Catal. Today, 157(1-4), 351 (2010)

[16] Ramesh K, Goh YLE, Gwie CG, Jie C, White TJ, Borgna A, J. Porous Mat., 19, 423 (2012)

[17] Ramesh K, Zheng JE, Ling EGY, Han YF, Borgna A, J. Phys. Chem. C, 113, 16530 (2009)

[18] Nguyen TTN, Ruaux V, Massin L, Lorenzt C, Afanasiev P, Mauge F, Belliere-Baca V, Rey P, Millet JMM, Appl. Catal. B: Environ., 166-167, 432 (2015)

[19] Nguyen TTN, Ruaux V, Mauge F, Belliere-Baca V, Rey P, Millet JMM, Appl. Catal. A: Gen., 504, 4 (2015)

[20] Blanco E, Delichere P, Millet JMM, Loridant S, Catal. Today, 226, 185 (2014)

[21] Millet JMM, Virely C, Forissier M, Bussiere P, Vedrine JC, Hyperfine Interact., 46, 619 (1989)

[22] Lauriol-Garbay P, Millet JMM, Loridant S, Belliere-Baca V, Rey P, J. Catal., 280(1), 68 (2011)

[23] Nguyen NTT, Matei-Rutkovska F, Huchede M, Jaillardon K, Qingyi G, Michel C, Millet JMM, Catal. Today, 323, 62 (2019)

[24] Settle E, Berstis L, Rorrer NA, Roman-Leshkov Y, Beckham GT, Richards RM, Vardon DR, Green Chem., 19, 3468 (2017)

[25] Glorieux B, Matecki M, Fayon F, Coutures JP, Palau S, Douy A, Peraudeau G, J. Nucl. Mater., 326, 156 (2004)

[26] Terra O, Clavier N, Dacheux N, Podor R, New J. Chem., 27, 957 (2003)

[27] Stranz M, Gut W, Fiedorow R, Ryszard Prace Naukowe Akademii Ekonomicznej, 338, 199 (1986).

[28] Calzolari L, Cavani F, Monti T, C. R. Acad. Sci. Paris, Serie IIc, Chimie/Chemistry, 3, 533 (2000).

[29] Clearfield A, Inorganic Ion Exchange Materials, CRC Press, Boca Raton, FL,1982.

[30] Tanabe K, Misono M, Ono Y, Hattori H, Stud. Surf. Sci. Catal., 51, 260 (1990)

[31] Galtayries A, Sporken R, Riga J, Blanchard G, Caudano R, J. Electron Spectrosc. Relat. Phenom., 88-91, 951 (1998)

[32] Lopez JM, Gilbank AL, Garcia T, Solsona B, Agouram S, Torrente-Murciano L, Appl. Catal. B: Environ., 174-175, 403 (2015)

[33] Sato S, Takahashi R, Sodesawa T, Honda NT, J. Mol. Catal. A-Chem., 221(1-2), 177 (2004)