3-O-β-D-glucopyranosyl-D-mannitol | 33904-37-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-O-β-D-glucopyranosyl-D-mannitol
• 英文别名: 3-β-D-glucopyranosyl-D-glucitol；3-O-β-D-Glucopyranosyl-L-mannit；O-β-D-Gp(1->3)D-Man-ol；3-O-beta-glucopyranosyl-d-mannitol；(2R,3R,4R,5R)-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexane-1,2,3,5,6-pentol
• CAS: 33904-37-9
• 化学式: C₁₂H₂₄O₁₁
• 分子量: 344.316
• InChiKey: VQHSOMBJVWLPSR-VOXHDCLVSA-N

物化性质

• 熔点：
  97-100 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• 沸点：
  788.5±60.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.2
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  201
• 氢给体数：
  9
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  纤维素二糖 在 氢气 作用下， 以 水 为溶剂， 159.84 ℃ 、5.0 MPa 条件下， 生成 3-O-β-D-glucopyranosyl-D-mannitol 、 山梨醇
  参考文献：
  名称：

  Selective conversion of microcrystalline cellulose into hexitols over a Ru/[Bmim]3PW12O40 catalyst under mild conditions

  摘要：

  A catalyst consisting of dispersed Ru on an ionic liquid (BmimPF(6))-heteropolyacid (H3PW12O40 center dot nH(2)O) hybrid as a support, i.e. Ru/[Bmim](3)PW12O40, has been successfully synthesized. The catalyst, which combines the Ru sites for hydrogenation and both Lewis and Bronsted acidic sites for hydrolysis, exhibits a superior catalytic performance for selective conversion of the microcrystalline cellulose to hexitols over the catalyst of mixing [Bmim](3)PW12O40 and Ru/C. On the Ru/[Bmim](3)PW12O40 catalyst, a sorbitol selectivity of 70.3% with a microcrystalline cellulose conversion of 63.7% was achieved in 24 h at 433 K and 5 MPa H-2. The superior catalytic performance of Ru/[Bmim](3)PW12O40 has been characterized using the hydrogenolysis of cellobiose as a probe reaction and was attributed to the Bronsted acid sites generated from hydrogen spillover from the Ru sites to the O sites of the support. In situ generation of the Bronsted acidic sites through hydrogen spillover has been confirmed by FT-IR characterization of pyridine adsorption. Furthermore, pH changes after treating the catalyst in H-2 demonstrated that dissolution of the protons generated on the oxygen sites as a result of hydrogen spillover acidifies the liquid product. These Bronsted acids work synergistically with the supported Ru and contribute to the enhanced hydrogenolysis activity. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cattod.2013.09.061

文献信息

• Verfahren zur Herstellung von epimerenfreien Zuckeralkoholen aus der Gruppe von Xylitol, Sorbitol (D-Glucitol), 4-O-beta-D-Galactopyranosyl-D-glucitol und 4-O-alpha-D-Glucopyranosyl-D-sorbitol
  申请人：BAYER AG

  公开号：EP0423525B1

  公开（公告）日：1993-06-23
• US5162517A
  申请人：——

  公开号：US5162517A

  公开（公告）日：1992-11-10
• US5641872A
  申请人：——

  公开号：US5641872A

  公开（公告）日：1997-06-24
• Selective conversion of microcrystalline cellulose into hexitols over a Ru/[Bmim]3PW12O40 catalyst under mild conditions
  作者：Xianna Xie、Jinyu Han、Hua Wang、Xinli Zhu、Xiao Liu、Yufei Niu、Zhiqiang Song、Qingfeng Ge

  DOI：10.1016/j.cattod.2013.09.061

  日期：2014.9

  A catalyst consisting of dispersed Ru on an ionic liquid (BmimPF(6))-heteropolyacid (H3PW12O40 center dot nH(2)O) hybrid as a support, i.e. Ru/[Bmim](3)PW12O40, has been successfully synthesized. The catalyst, which combines the Ru sites for hydrogenation and both Lewis and Bronsted acidic sites for hydrolysis, exhibits a superior catalytic performance for selective conversion of the microcrystalline cellulose to hexitols over the catalyst of mixing [Bmim](3)PW12O40 and Ru/C. On the Ru/[Bmim](3)PW12O40 catalyst, a sorbitol selectivity of 70.3% with a microcrystalline cellulose conversion of 63.7% was achieved in 24 h at 433 K and 5 MPa H-2. The superior catalytic performance of Ru/[Bmim](3)PW12O40 has been characterized using the hydrogenolysis of cellobiose as a probe reaction and was attributed to the Bronsted acid sites generated from hydrogen spillover from the Ru sites to the O sites of the support. In situ generation of the Bronsted acidic sites through hydrogen spillover has been confirmed by FT-IR characterization of pyridine adsorption. Furthermore, pH changes after treating the catalyst in H-2 demonstrated that dissolution of the protons generated on the oxygen sites as a result of hydrogen spillover acidifies the liquid product. These Bronsted acids work synergistically with the supported Ru and contribute to the enhanced hydrogenolysis activity. (C) 2013 Elsevier B.V. All rights reserved.