Direct transformation of terminal alkenes with H 2 O into primary alcohols over metal oxide-supported Pd catalysts

Zhenzhong Zhang, Tetsuya Mamba, Eiji Yamamoto, Haruno Murayama, Tamao Ishida, Tetsuo Honma, Tadahiro Fujitani, Makoto Tokunaga

研究成果: ジャーナルへの寄稿記事

2 引用 (Scopus)

抄録

The anti-Markovnikov addition of H 2 O to alkenes to directly bring in primary alcohols has been considered one of the “10 challenges in catalysis” in the 1990s, but the challenging issue has still remained unsolved over the past few decades, particularly in terms of developing an atom-efficient synthetic strategy. In this context, we introduce a novel access for the transformation of terminal alkenes with H 2 O into the corresponding primary alcohols over metal oxide-supported Pd catalysts, employing O 2 as the sole oxidant. Direct and efficient synthesis of cinnamyl alcohol from allylbenzene and H 2 O was initially achieved as a fine chemical example over Pd(NO 3 ) 2 /CeO 2 -ZrO 2 , and the target saturated alcohol (3-phenylpropan-1-ol) was obtained as the anti-Markovnikov selective product from a “one-pot” process using H 2 as the reductant. The Pd(NO 3 ) 2 /CeO 2 -ZrO 2 was characterized by HAADF-STEM, XRD and X-ray absorption fine structure (XAFS) analyses, indicating that the molecular Pd(NO 3 ) 2 is probably deposited as it is on the support, which likely plays an important role to promote this reaction. In the second part, Pd(NO 3 ) 2 /CeO 2 -ZrO 2 and other supported Pd catalysts were applied for the transformation of 1,3-butadiene into 2-butene-1,4-diol in a batch reactor. Besides, butane-1,4-diol, which is an important industrial material, was efficiently produced by the simple hydrogenation of 2-butene-1,4-diol in a “one-pot” manner. Significantly, the development of the reaction catalyzed by supported Pd in a gas flow reactor bestows great potential to further industrial applications. Additionally, the adsorption structure of 1,3-butadiene on Pd(111) was confirmed as the s-trans form by infrared reflection absorption spectroscopy (IRAS) measurements. The change in the electronic states of surface Pd atoms upon oxygen adsorption was observed by X-ray photoelectron spectroscopy (XPS).

元の言語英語
ページ(範囲)100-110
ページ数11
ジャーナルApplied Catalysis B: Environmental
DOI
出版物ステータス出版済み - 6 5 2019

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alkene
Alkenes
Catalyst supports
Oxides
Olefins
alcohol
Alcohols
Metals
catalyst
Butadiene
Butenes
Adsorption
Atoms
Reducing Agents
X ray absorption
Batch reactors
Electronic states
adsorption
Absorption spectroscopy
Oxidants

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Environmental Science(all)
  • Process Chemistry and Technology

これを引用

Direct transformation of terminal alkenes with H 2 O into primary alcohols over metal oxide-supported Pd catalysts . / Zhang, Zhenzhong; Mamba, Tetsuya; Yamamoto, Eiji; Murayama, Haruno; Ishida, Tamao; Honma, Tetsuo; Fujitani, Tadahiro; Tokunaga, Makoto.

:: Applied Catalysis B: Environmental, 05.06.2019, p. 100-110.

研究成果: ジャーナルへの寄稿記事

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abstract = "The anti-Markovnikov addition of H 2 O to alkenes to directly bring in primary alcohols has been considered one of the “10 challenges in catalysis” in the 1990s, but the challenging issue has still remained unsolved over the past few decades, particularly in terms of developing an atom-efficient synthetic strategy. In this context, we introduce a novel access for the transformation of terminal alkenes with H 2 O into the corresponding primary alcohols over metal oxide-supported Pd catalysts, employing O 2 as the sole oxidant. Direct and efficient synthesis of cinnamyl alcohol from allylbenzene and H 2 O was initially achieved as a fine chemical example over Pd(NO 3 ) 2 /CeO 2 -ZrO 2 , and the target saturated alcohol (3-phenylpropan-1-ol) was obtained as the anti-Markovnikov selective product from a “one-pot” process using H 2 as the reductant. The Pd(NO 3 ) 2 /CeO 2 -ZrO 2 was characterized by HAADF-STEM, XRD and X-ray absorption fine structure (XAFS) analyses, indicating that the molecular Pd(NO 3 ) 2 is probably deposited as it is on the support, which likely plays an important role to promote this reaction. In the second part, Pd(NO 3 ) 2 /CeO 2 -ZrO 2 and other supported Pd catalysts were applied for the transformation of 1,3-butadiene into 2-butene-1,4-diol in a batch reactor. Besides, butane-1,4-diol, which is an important industrial material, was efficiently produced by the simple hydrogenation of 2-butene-1,4-diol in a “one-pot” manner. Significantly, the development of the reaction catalyzed by supported Pd in a gas flow reactor bestows great potential to further industrial applications. Additionally, the adsorption structure of 1,3-butadiene on Pd(111) was confirmed as the s-trans form by infrared reflection absorption spectroscopy (IRAS) measurements. The change in the electronic states of surface Pd atoms upon oxygen adsorption was observed by X-ray photoelectron spectroscopy (XPS).",
author = "Zhenzhong Zhang and Tetsuya Mamba and Eiji Yamamoto and Haruno Murayama and Tamao Ishida and Tetsuo Honma and Tadahiro Fujitani and Makoto Tokunaga",
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T1 - Direct transformation of terminal alkenes with H 2 O into primary alcohols over metal oxide-supported Pd catalysts

AU - Zhang, Zhenzhong

AU - Mamba, Tetsuya

AU - Yamamoto, Eiji

AU - Murayama, Haruno

AU - Ishida, Tamao

AU - Honma, Tetsuo

AU - Fujitani, Tadahiro

AU - Tokunaga, Makoto

PY - 2019/6/5

Y1 - 2019/6/5

N2 - The anti-Markovnikov addition of H 2 O to alkenes to directly bring in primary alcohols has been considered one of the “10 challenges in catalysis” in the 1990s, but the challenging issue has still remained unsolved over the past few decades, particularly in terms of developing an atom-efficient synthetic strategy. In this context, we introduce a novel access for the transformation of terminal alkenes with H 2 O into the corresponding primary alcohols over metal oxide-supported Pd catalysts, employing O 2 as the sole oxidant. Direct and efficient synthesis of cinnamyl alcohol from allylbenzene and H 2 O was initially achieved as a fine chemical example over Pd(NO 3 ) 2 /CeO 2 -ZrO 2 , and the target saturated alcohol (3-phenylpropan-1-ol) was obtained as the anti-Markovnikov selective product from a “one-pot” process using H 2 as the reductant. The Pd(NO 3 ) 2 /CeO 2 -ZrO 2 was characterized by HAADF-STEM, XRD and X-ray absorption fine structure (XAFS) analyses, indicating that the molecular Pd(NO 3 ) 2 is probably deposited as it is on the support, which likely plays an important role to promote this reaction. In the second part, Pd(NO 3 ) 2 /CeO 2 -ZrO 2 and other supported Pd catalysts were applied for the transformation of 1,3-butadiene into 2-butene-1,4-diol in a batch reactor. Besides, butane-1,4-diol, which is an important industrial material, was efficiently produced by the simple hydrogenation of 2-butene-1,4-diol in a “one-pot” manner. Significantly, the development of the reaction catalyzed by supported Pd in a gas flow reactor bestows great potential to further industrial applications. Additionally, the adsorption structure of 1,3-butadiene on Pd(111) was confirmed as the s-trans form by infrared reflection absorption spectroscopy (IRAS) measurements. The change in the electronic states of surface Pd atoms upon oxygen adsorption was observed by X-ray photoelectron spectroscopy (XPS).

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