Enhancement of Catalytic Activity on Pd/C and Te–Pd/C During the Oxidative Dehydrogenation of Sodium Lactate to Pyruvate in an Aqueous Phase Under Pressurized Oxygen

Sugiyama, Shigeru; Kikumoto, Tetsuo; Tanaka, Haruki; Nakagawa, Keizo; Sotowa, Ken‐Ichiro; Maehara, Keiko; Himeno, Yoshiyuki; Ninomiya, Wataru

doi:10.1007/s10562-009-9920-3

Cited by 36 publications

(52 citation statements)

References 22 publications

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“…Loading with these heavy metals (M = Pd or Te) was quantified as an atomic ratio relative to palladium (M/Pd). Catalytic activity was tested as previously reported (Sugiyama et al, 2009). Into a stainless steel autoclave (85 mL), 50 or 25 mL of an aqueous reaction solution containing sodium lactate (25 or 12.5 mmol) was added.…”

Section: Methodsmentioning

confidence: 99%

Application of Heavy-Metal-Free Pd/C Catalyst for the Oxidative Dehydrogenation of Sodium Lactate to Pyruvate in an Aqueous Phase under Pressurized Oxygen

Sugiyama

Tanaka

Kikumoto

et al. 2010

J. Chem. Eng. Japan

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According to previous reports, the oxidative dehydrogenation of lactic acid to pyruvic acid in an aqueous phase does not proceed with Pd/C, while Pd/C doped with Te or Pb has catalytic activity at atmospheric pressure and 363 K in an aqueous NaOH solution at a pH of 8. Since use of heavy metals, such as Te or Pb, is inconsistent with green chemistry, a heavy-metal-free Pd/C catalyst is employed in the present study. The oxidative dehydrogenation of sodium lactate to sodium pyruvate in an aqueous phase at 358 K under pressurized oxygen at 1 MPa proceeded favorably using Pd/C with no adjustment of solution pH. Under pressurized oxygen, the catalytic activity of Pd/C was similar to that of Pd/C doped with either Te or Pb. This result suggests that a heavy-metal-free Pd/C catalytst might also be applied to other catalytic reactions. As an alternative to doping Pd/C with Te or Pb, the dissolution of gaseous oxygen into the reaction solution significantly enhanced the catalytic activity of Pd/C. To show the contribution of the dissolution of gaseous oxygen, the effects of the volume of oxygen in the reactor (stainless autoclave) on the reaction rate and the activity were examined. The activation parameters thus obtained reveal that the volume of oxygen in the reactor is a more important determinant of catalytic activity than the activation of the reaction itself.

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Section: Methodsmentioning

confidence: 99%

Application of Heavy-Metal-Free Pd/C Catalyst for the Oxidative Dehydrogenation of Sodium Lactate to Pyruvate in an Aqueous Phase under Pressurized Oxygen

Sugiyama

Tanaka

Kikumoto

et al. 2010

J. Chem. Eng. Japan

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“…Lactates can be converted into various commodity chemicals, including acrylic acid, pyruvic acid and pyruvates, lactide, acetaldehyde and propanediol . In particular, pyruvate esters are important chemicals used in many sectors, including agrochemicals, foodstuffs, cosmetics, and pharmaceuticals . Pyruvate is a key metabolite, and is biologically produced from sugars by microorganisms .…”

Section: Methodsmentioning

confidence: 99%

Selective Aerobic Oxidation of Lactate to Pyruvate Catalyzed by Vanadium‐Nitrogen‐Doped Carbon Nanosheets

et al. 2019

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The catalytic oxidative dehydrogenation of lactates with molecular oxygen is a promising yet challenging route for producing high‐value pyruvates from biomass. Here we report a simple synthetic strategy for preparing nitrogen‐doped carbon nanosheets (NCNs) starting from two abundant precursors, cheap melamine and glucose, and using a simple thermal‐annealing process. The resulting NCNs feature numerous edges and holes for anchoring vanadium oxides (V‐NCNs). This creates cooperative catalytic sites that boost the catalytic oxidation of ethyl lactate to ethyl pyruvate. Additionally, we systematically studied the surface nitrogen species of NCNs by varying the pyrolysis temperature, and found that the active pyridinic N‐oxide species formed in a high thermal‐annealing treatment, acting synergistically with vanadium active sites in converting ethyl lactate with oxygen into ethyl pyruvate under mild conditions.

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“…Due to the inherent steric hindrance and electronic effect, complete conversion of α-hydroxy esters is usually difficult, while oxidative C-C bond cleavage could easily occur between two adjacent carbonyl carbon atoms under harsh oxidative reaction conditions [7,8]. Recently, several efficient aerobic catalytic systems have been developed under mild liquid reaction conditions [9,10,11,12,13], such as Pd-, Au-, and Ru-based catalysts, AZADO-NaNO 2 and TEMPO-NaNO 2 . We are encouraged by all these methods, although some drawbacks still exist, such as side reactions, and use of expensive organic or metal catalysts.…”

Section: Introductionmentioning

confidence: 99%

Novel Effect of Zinc Nitrate/Vanadyl Oxalate for Selective Catalytic Oxidation of α-Hydroxy Esters to α-Keto Esters with Molecular Oxygen: An In Situ ATR-IR Study

Xiao

et al. 2019

Molecules

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Selective oxidation of α-hydroxy esters is one of the most important methods to prepare high value-added α-keto esters. An efficient catalytic system consisting of Zn(NO3)2/VOC2O4 is reported for catalytic oxidation of α-hydroxy esters with molecular oxygen. Up to 99% conversion of methyl DL-mandelate or methyl lactate could be facilely obtained with high selectivity for its corresponding α-keto ester under mild reaction conditions. Zn(NO3)2 exhibited higher catalytic activity in combination with VOC2O4 compared with Fe(NO3)3 and different nitric oxidative gases were detected by situ attenuated total reflection infrared (ATR-IR) spectroscopy. UV-vis and ATR-IR results indicated that coordination complex formed in Zn(NO3)2 in CH3CN solution was quite different from Fe(NO3)3; it is proposed that the charge-transfer from Zn2+ to coordinated nitrate groups might account for the generation of different nitric oxidative gases. The XPS result indicate that nitric oxidative gas derived from the interaction of Zn(NO3)2 with VOC2O4 could be in favor of oxidizing VOC2O4 to generate active vanadium (V) species. It might account for different catalytic activity of Zn(NO3)2 or Fe(NO3)3 combined with VOC2O4. This work contributes to further development of efficient aerobic oxidation under mild reaction conditions.

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Enhancement of Catalytic Activity on Pd/C and Te–Pd/C During the Oxidative Dehydrogenation of Sodium Lactate to Pyruvate in an Aqueous Phase Under Pressurized Oxygen

Cited by 36 publications

References 22 publications

Application of Heavy-Metal-Free Pd/C Catalyst for the Oxidative Dehydrogenation of Sodium Lactate to Pyruvate in an Aqueous Phase under Pressurized Oxygen

Application of Heavy-Metal-Free Pd/C Catalyst for the Oxidative Dehydrogenation of Sodium Lactate to Pyruvate in an Aqueous Phase under Pressurized Oxygen

Selective Aerobic Oxidation of Lactate to Pyruvate Catalyzed by Vanadium‐Nitrogen‐Doped Carbon Nanosheets

Novel Effect of Zinc Nitrate/Vanadyl Oxalate for Selective Catalytic Oxidation of α-Hydroxy Esters to α-Keto Esters with Molecular Oxygen: An In Situ ATR-IR Study

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