Production of acrolein and acrylic acid through dehydration and oxydehydration of glycerol with mixed oxide catalysts

Deleplanque, J.; Dubois, Jean‐Luc; Devaux, Jean-François; Ueda, Wataru

doi:10.1016/j.cattod.2010.04.012

Cited by 184 publications

(137 citation statements)

References 17 publications

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“…32 The industrial catalyst has a complex structure formed by V-Mo-W oxides. 33 Deleplanque et al 34 studied the glycerol oxydehydration to acrylic acid over mixed oxide catalysts in the presence of oxygen. They were able to find up to 28% selectivity to acrylic acid over Mo-V-Te-Nb mixed oxides.…”

Section: Introductionmentioning

confidence: 99%

Oxidative dehydration of glycerol to acrylic acid over vanadium-impregnated zeolite beta

Pestana¹,

Guerra²,

Ferreira³

et al. 2013

J. Braz. Chem. Soc.

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A desidratação oxidativa do glicerol a ácido acrílico foi estudada com o uso de zeólita Beta impregnada com vanádio. Os catalisadores foram preparados por impregnação úmida do metavanadato de amônio sobre a zeólita Beta na forma amoniacal, seguida de calcinação em ar a 823 K. A impregnação reduziu a área superficial específica, mas não afetou significativamente a acidez (Brønsted e Lewis) da zeólita. A avaliação dos catalisadores foi realizada num reator de leito fixo usando ar como gás de arraste e injetando o glicerol por meio de uma bomba seringa. Acroleína foi o principal produto formado, tendo também sido observados acetaldeído e hidróxi-acetona (acetol). O ácido acrílico foi formado em aproximadamente 25% de seletividade a 548 K sobre as zeólitas impregnadas. O resultado pode ser explicado por análises de XPS (espectroscopia fotoeletrônica de raios X), que mostraram uma boa dispersão de vanádio nos poros da zeólita.The oxidative dehydration of glycerol to acrylic acid was studied over vanadium-impregnated zeolite Beta. Catalysts were prepared by wet impregnation of ammonium metavanadate over ammonium-exchanged zeolite Beta, followed by air calcination at 823 K. Impregnation reduced the specific surface area, but did not significantly affected the acidity (Brønsted and Lewis) of the zeolites. The catalytic evaluation was carried out in a fixed bed flow reactor using air as the carrier and injecting glycerol by means of a syringe pump. Acrolein was the main product, with acetaldehyde and hydroxy-acetone (acetol) being also formed. Acrylic acid was formed with approximately 25% selectivity at 548 K over the impregnated zeolites. The result can be explained by XPS (X-ray photoelectron spectroscopy) measurements, which indicated a good dispersion of the vanadium inside the pores.Keywords: glycerol, acrylic acid, zeolite, dehydration, oxidation IntroductionGlycerol is usually found in combination with fatty acids of natural occurrence forming the triglycerides. Today, the major source of glycerol is the transesterification of oils and fats to produce biodiesel. 1 In this reaction, a molecule of triglyceride reacts with three molecules of methanol, under base catalysis conditions, to afford three molecules of fatty acid methyl esters (the biodiesel) and a molecule of glycerol (Scheme 1). In recent years, the growing concern about global warming has motivated the use of biofuels. Biodiesel, together with bioethanol, is one of the most important biofuels used nowadays.For each 90 m 3 of biodiesel produced by transesterification, about 10 m 3 of glycerol are obtained. The worldwide glycerol production will reached 2 approximately 1.2 million tons in 2012 and most of this production will come from the biodiesel industry. In Brazil, for instance, there is a mandatory blend of 5% of biodiesel in the petrodiesel, which represents an annual glycerol production of approximately 300,000 tons. The traditional markets for glycerol are cosmetics, soaps, pharmaceuticals and personal care products. However, with the increasing ...

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Section: Introductionmentioning

confidence: 99%

Oxidative dehydration of glycerol to acrylic acid over vanadium-impregnated zeolite beta

Pestana¹,

Guerra²,

Ferreira³

et al. 2013

J. Braz. Chem. Soc.

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“…These catalysts are known to be active in esterication [43][44][45][46][47] and hydrolysis reactions, 48,49 as well as in the production of acrylic acid from glycerol and acrolein. 50 Accordingly, we screened zeolites, commercial ion-exchange resins, (mixed) metal-oxides, and sulfonated carbonaceous and siliceous catalysts. All catalysts were tested using an initial LA : AcOH molar ratio of 1 : 3.3, at 100 C under atmospheric pressure.…”

Section: Catalyst Testing and Structure-activity Considerationsmentioning

confidence: 99%

Catalytic acetoxylation of lactic acid to 2-acetoxypropionic acid, en route to acrylic acid

et al. 2015

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Catalytic acetoxylation of lactic acid to 2-acetoxypropionic acid, en route to acrylic acid Beerthuis, R.; Granollers, M.; Brown, D.R.; Salavagione, H.J.; Rothenberg, G.; Shiju, N.R. Published in: RSC Advances DOI:10.1039/c4ra12695eLink to publication Citation for published version (APA):Beerthuis, R., Granollers, M., Brown, D. R., Salavagione, H. J., Rothenberg, G., & Shiju, N. R. (2015). Catalytic acetoxylation of lactic acid to 2-acetoxypropionic acid, en route to acrylic acid. RSC Advances, 5(6), 4103-4108. DOI: 10.1039/c4ra12695e General rightsIt is not permitted to download or to forward/distribute the text or part of it without the consent of the author(s) and/or copyright holder(s), other than for strictly personal, individual use, unless the work is under an open content license (like Creative Commons). Disclaimer/Complaints regulationsIf you believe that digital publication of certain material infringes any of your rights or (privacy) interests, please let the Library know, stating your reasons. In case of a legitimate complaint, the Library will make the material inaccessible and/or remove it from the website. Please Ask the Library: http://uba.uva.nl/en/contact, or a letter to: Library of the University of Amsterdam, Secretariat, Singel 425, 1012 WP Amsterdam, The Netherlands. You will be contacted as soon as possible. We present an alternative synthetic route to acrylic acid, starting from the platform chemical lactic acid and using heterogeneous catalysis. To improve selectivity, we designed an indirect dehydration reaction that proceeds via acetoxylation of lactic acid to 2-acetoxypropionic acid. This intermediate can then be pyrolized to acrylic acid. Acetic acid is used both as a reagent and a solvent in the first step, and may be recovered in the subsequent pyrolysis step. We tested a range of solid acid catalysts for the acetoxylation step (Y zeolites, sulfated zirconia, ion-exchange resins, sulfonated graphene, and various sulfonated silica gels and mixed oxides). Recycling studies were carried out for the most active catalysts. To enable quantitative analysis using gas chromatography we also developed a reliable silylation derivatization method, which is also reported. These results open opportunities for improving the biorenewable production of acrylic acid.

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“…In a previous paper by the authors [4] as well as a few available reviews [5][6][7] gives a good overview of the subject; the classes of catalysts used include: heteropoly acids and other supported inorganic acids [8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26], zeolites [21,[27][28][29][30][31][32][33], mixed oxides [34][35][36][37][38][39][40][41], and sulphated zirconia [42,43], all of which are solid acid materials. The acids usually contain or are promoted with P, W, S, Mo, and B, Abstract Pore condensation has been suggested as an initiator of deactivation in the dehydration of glycerol to acrolein.…”

Section: Introductionmentioning

confidence: 99%

“…The carbon formation is suggested to depend on oligomer formation with hydroxyacetone as a precursor [31,35]; indeed recycling of hydroxyacetone very much favours carbon formation [4]. Deleplanque et al [35] imply that formation of olefins (yielding subsequent aromatics, oligomers and coke) is a possible parallel deactivation mechanism and in a separate paper Suprun et al derived the deactivation to Brønstead acid sites [15]. The same researchers also found that the higher the temperature the lower the hydrogen-tocarbon quote was in the resulting deposits.…”

Section: Introductionmentioning

confidence: 99%

Pore Condensation in Glycerol Dehydration: Modification of a Mixed Oxide Catalyst

Hulteberg

Leveau²,

Brandin

2017

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Production of acrolein and acrylic acid through dehydration and oxydehydration of glycerol with mixed oxide catalysts

Cited by 184 publications

References 17 publications

Oxidative dehydration of glycerol to acrylic acid over vanadium-impregnated zeolite beta

Oxidative dehydration of glycerol to acrylic acid over vanadium-impregnated zeolite beta

Catalytic acetoxylation of lactic acid to 2-acetoxypropionic acid, en route to acrylic acid

Pore Condensation in Glycerol Dehydration: Modification of a Mixed Oxide Catalyst

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