Ring opening of decalin and tetralin on HY and Pt/HY zeolite catalysts

Santikunaporn, Malee; Herrera, José E.; Jongpatiwut, Siriporn; Resasco, Daniel E.; Alvarez, Walter E.; Sughrue, Ed L

doi:10.1016/j.jcat.2004.08.030

Cited by 173 publications

(113 citation statements)

References 20 publications

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“…An example of the product distributions obtained with the different catalysts at 723 K is shown in Table 2. These products are consistent with the proposed mechanisms for decalin reaction on acidic catalysts 14,17,19,20 and could be arbitrarily grouped as representative of the main reactions.…”

Section: Resultssupporting

confidence: 76%

“…All these variations can be explained based on a relatively more important occurrence of cracking of side chains, ring opening and alkylation reactions, and support the view that they are favored against hydrogen transfer reactions when temperature is increased. 22 Then, with basis in these results and previous reports, 14,17,[19][20][21] it is possible to postulate a new set of overall reaction paths, which is shown in Figure 7. As shown by the yield curves in Figure 4, direct and subsequent hydrogen transfer would constitute an important set of reactions from the beginning of the reaction system.…”

Section: Resultsmentioning

confidence: 58%

“…Santikunaporn et al 17 used a mixture of both isomers and reported a fast conversion of the cis-isomer with a minor formation of the trans-isomer at 533 K and short space times over Y zeolite, the other products being mostly C 10 molecules after isomerization and ring opening and contraction reactions. Sousa-Aguiar et al, 18 who used a mixture of the isomers over deuterated zeolites, also identified cis-decalin as the most reactive, and suggested that the reaction is initiated by means of a nucleophilic attack by the zeolite protons on the tertiary carbons in decalin, which are more exposed in the cis-isomer (see Figure 2).…”

Section: Resultsmentioning

confidence: 99%

“…23 In coincidence, aromatic selectivities of 35% 19 and initial molar selectivities of 0.791 20 were reported among products in the conversion of decalin over zeolitic catalysts at high reaction temperatures from 723 to 823 K. Other authors found very low yields, possibly due to the low reaction temperatures, below 623 K, or to the co-feeding of hydrogen in the reaction medium that might saturate intermediate olefins. 14,17 Hydrogen transfer was suggested a major reaction at temperatures higher than 623 K, leading to up to 40% of aromatics in the conversion of decalin over acidic catalysts loaded with metals such as Pt or Ir. 24 The impact of hydrogen transfer on aromatic yields was underlined by Sousa-Aguiar et al, 18 who associated the low concentration of olefins in the reaction medium to their consumption through these reactions, where naphthenes may play a donor role and convert themselves into aromatics.…”

Section: Resultsmentioning

confidence: 99%

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Yield of aromatics from naphthenics upon catalytic cracking

Pujro¹,

Falco²,

Pedrosa³

et al. 2012

J. Braz. Chem. Soc.

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Cis-e trans decalina foram submetidas à reação com catalisadores de craqueamento, para estudar a formação de aromáticos numa fração particular de produtos líquidos do processo de craqueamento catalítico fluido (FCC). Um reator batelada em leito fluidizado, CREC, foi usado a 673 e 723 K com tempos de contato entre 3 e 15 s. Cis-decalina foi muito mais reativa. Apesar de diferenças induzidas e medidas na acessibilidade dos catalisadores, seus perfis de atividade foram similares, sugerindo que restrições difusionais não prevalecem. Os produtos foram hidrocarbonetos C 1 -C 12 , enquanto o coque foi muito baixo. Reações de isomerização, craqueamento, transferência de hidrogênio, abertura/contração de anel e alquilação ocorreram, e produtos das várias reações foram observados em tempos de reação muito baixos. Naftênicos bicíclicos C 10 e aromáticos alquilsubstituídos C 7 -C 11 ou nafteno-aromáticos foram os produtos mais importantes. Um mecanismo de reação com três rotas iniciais (isomerização, abertura de anel e reações de transferência de hidrogênio) foi proposto.Cis-and trans-decalin were reacted over cracking catalysts to study the formation of aromatics in a particular fraction of the liquid products obtained in the fluid catalytic cracking process (FCC). A batch, fluidized bed CREC riser simulator reactor was used at 673 and 723 K and contact times varied from 3 to 15 s. Cis-decalin was much more reactive. Despite differences induced and measured in their accessibility indices, the catalysts led to similar activity profiles, suggesting that diffusion restrictions do not prevail. Products were C 1 -C 12 hydrocarbons while coke was very low. Isomerization, cracking, hydrogen transfer, ring opening, ring contraction and alkylation reactions occurred and products from the various reactions were observed at very short reaction times. Bicyclic C 10 naphthenics and alkyl-substituted C 7 -C 11 aromatics or naphtheno-aromatics were the most important products. A reaction mechanism with three initial routes (isomerization, ring opening and direct hydrogen transfer reactions) was proposed.

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Section: Resultssupporting

confidence: 76%

Section: Resultsmentioning

confidence: 58%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

Yield of aromatics from naphthenics upon catalytic cracking

Pujro¹,

Falco²,

Pedrosa³

et al. 2012

J. Braz. Chem. Soc.

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show abstract

“…However, both of them have some limitations [5]. An interesting and alternative technology for improving the cetane number of diesels and maintaining meanwhile high diesel yields is achieved by combining a complete hydrogenation process with a selective ring opening (SRO) reaction of the naphthenic rings [7]. The SRO is defined as follows: naphthene rings are opened to form compounds with high cetane number, but without any carbon losses [5,8].…”

Section: Introductionmentioning

confidence: 99%

Coupled hydrogenation and ring opening of tetralin on potassium modified Pt/USY catalysts

Yang

Wen

et al. 2007

Catal Lett

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Coupled hydrogenation and ring opening of tetralin (THN) on Pt/USY catalyst were performed on a high-pressure fixed-bed reactor. The effect of reaction temperature in range of 100-300°C and the nature of the catalyst (metal and acid sites) on the catalytic performance were studied. The results indicated that the extent of hydrocracking, a sequential reaction of ring opening, should be reduced in order to maintain high yields of the ring opening products (ROP). Introduction of the Pt component accelerated the hydrogenation and ring opening of the THN significantly. It was also found to be an effective way to optimize the acid properties of the catalysts by introducing an appropriate amount of potassium to the catalyst, such that the strong acid sites of the catalysts were diminished, and a higher ROP yield could be obtained as a result of the inhibiting of the hydrocracking activity of the catalyst. When the yield of the C10 fractions could be maintained at 90 wt.%, then a maximal ROP yield of 35.6 wt.% could be obtained on a 0.5 wt.% Pt/USY catalyst loaded with 2.0 wt.% of K.

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Thermochemical Characterization

Cardona-Martı́nez¹,

Dumesic²

2008

Handbook of Heterogeneous Catalysis

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The sections in this article are Introduction Principles of Temperature‐Programmed Desorption Applications of Temperature‐Programmed Desorption Principles of Adsorption Microcalorimetry Applications of Adsorption Microcalorimetry Conclusions

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Ring opening of decalin and tetralin on HY and Pt/HY zeolite catalysts

Cited by 173 publications

References 20 publications

Yield of aromatics from naphthenics upon catalytic cracking

Yield of aromatics from naphthenics upon catalytic cracking

Coupled hydrogenation and ring opening of tetralin on potassium modified Pt/USY catalysts

Thermochemical Characterization

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