Oxidative C-C bond cleavage of lignin model compound with O<sub>2</sub> in presence of N-hydroxyl phthalimide

LIU Changjun; CHEN Ning; LIU Yingying; LU Houfang; LIANG Bin; TANG Siyang; YUE Hairong; TAN Pinghua

doi:10.11949/j.issn.0438-1157.20170533

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Oxidative C-C bond cleavage of lignin model compound with O₂ in presence of N-hydroxyl phthalimide

更新时间：2025-12-10

- Oxidative C-C bond cleavage of lignin model compound with O₂ in presence of N-hydroxyl phthalimide
- CIESC Journal Issue 10, Pages: 3788-3794(2017)
- 作者机构：
  
  1. 四川大学化学工程学院,四川,成都,610207
  2. 四川大学 CCUS与CO
  3. 西南化工研究设计院有限公司,四川,成都,610225
- 作者简介：
- 基金信息：
- DOI：10.11949/j.issn.0438-1157.20170533
  CLC： 643.32O625
- Online First：05 October 2017，
  
  Published：05 October 2017
- 稿件说明：
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LIU Changjun, CHEN Ning, LIU Yingying, et al. Oxidative C-C bond cleavage of lignin model compound with O₂ in presence of N-hydroxyl phthalimide[J]. CIESC Journal, 2017, (10): 3788-3794. DOI: 10.11949/j.issn.0438-1157.20170533.
DOI：

LIU Changjun, CHEN Ning, LIU Yingying, et al. Oxidative C-C bond cleavage of lignin model compound with O₂ in presence of N-hydroxyl phthalimide[J]. CIESC Journal, 2017, (10): 3788-3794. DOI: 10.11949/j.issn.0438-1157.20170533. DOI：

摘要

以1，2-二苯乙烷为模型分子，考察了N-羟基邻苯二甲酰亚胺（NHPI）对分子氧氧化断裂木质素分子中C-C键的催化作用，比较了Cu、Co和Mn的多种可溶性盐对NHPI催化活性的促进作用，探究了工艺条件对1，2-二苯乙烷氧化的影响规律。结果表明：NHPI能够在温和条件下催化分子氧氧化1，2-二苯乙烷中的C-C键断裂生成苯甲醛和苯甲酸。可溶性的Cu、Co和Mn盐都具有助催化作用，其中乙酸锰的助催化作用最强。确定了二苯基乙酮为氧化的初级反应产物。发现提高反应温度、增加乙酸锰用量以及延长反应时间，有利于C-C键的氧化断裂和提高小分子产物的选择性。优化的反应条件为NHPI为底物物质的量的10%，乙酸锰和NHPI之比为1：10，反应温度90℃，氧气分压1.0 MPa，反应时间8 h，C-C键的氧化断裂产物苯甲醛和苯甲酸的总选择性可达76.5%。

Abstract

The catalytic effects of N-hydroxyl phthalimide combined with various transition metal salts on the oxidative breakage of C-C bond of lignin by O2 under mild conditions were studied.1

2-diphenylethane was adopted as the model compound of lignin C-C bond.It was found that Mn (OAc)2 showed the highest promotion effect on the catalytic activity of NHPI among the soluble cobaltous

manganous and cupric salts.The oxidative breakage of C-C bonds led to the production of benzyl aldehyde and benzoic acid with high selectivity.1

2-Diphenyl ethanone was found to be the primary product.Either increase the reaction temperature

Mn (OAc)2 amount as well as the reaction time favored the C-C bond cleavage.Total selectivity of benzyl aldehyde and benzoic acid up to 76.5% was achieved in acetic acid under the conditions of 90℃ and 1.0 MPa O2 for 8 h by using 10% NHPI and 1% Mn (OAc)2 with respect to the amount of benzyl phenyl ether as the catalyst.

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Oxidative C-C bond cleavage of lignin model compound with O2 in presence of N-hydroxyl phthalimide

DOI：10.11949/j.issn.0438-1157.20170533

摘要

Abstract

关键词

Keywords

references

Oxidative C-C bond cleavage of lignin model compound with O₂ in presence of N-hydroxyl phthalimide