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化学进展 2022, Vol. 34 Issue (5): 1026-1041 DOI: 10.7536/PC210501 前一篇   后一篇

• 综述 •

以双氧水或氧气为氧化剂的苯羟基化制苯酚的催化反应机理

张明珏1,*(), 凡长坡1, 王龙1, 吴雪静1, 周瑜2, 王军2,*()   

  1. 1.东南大学成贤学院制药与化学化工学院 南京 210088
    2.南京工业大学化工学院 南京 210009
  • 收稿日期:2021-05-03 修回日期:2021-09-06 出版日期:2022-05-24 发布日期:2021-12-02
  • 通讯作者: 张明珏, 王军
  • 基金资助:
    国家自然科学基金项目(22072065); 国家自然科学基金项目(U1662107); 国家自然科学基金项目(21476109); 东南大学成贤学院青年教师科研发展基金(z0003)
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Catalytic Reaction Mechanism for Hydroxylation of Benzene to Phenol with H2O2/O2 as Oxidants

Mingjue Zhang1(), Changpo Fan1, Long Wang1, Xuejing Wu1, Yu Zhou2, Jun Wang2()   

  1. 1. Department of Chemical and Pharmaceutical Engineering, Southeast University ChengXian College,Nanjing 210088, China
    2. College of Chemical Engineering, Nanjing Tech University,Nanjing 210009, China
  • Received:2021-05-03 Revised:2021-09-06 Online:2022-05-24 Published:2021-12-02
  • Contact: Mingjue Zhang, Jun Wang
  • Supported by:
    National Natural Science Foundation of China(22072065); National Natural Science Foundation of China(U1662107); National Natural Science Foundation of China(21476109); Youth Foundation of Southeast University ChengXian College(z0003)

C—H键的活化是有机合成中最重要的科学问题之一。以环境友好的双氧水或者氧气为氧化剂的苯羟基化制备苯酚的反应,不仅涉及苯环的$\text C_{\text s \text p^{2}}— \text H $活化这一基础问题,还涉及双氧水或氧气的活化,以及双氧水的分解、苯酚的深度氧化等副反应,几十年来一直是有机合成领域的一大挑战。更重要的是,在大力倡导绿色化工的背景之下,该反应愈加受到工业界的青睐,期望它能够取代异丙苯法成为苯酚生产的绿色新工艺。本文以苯羟基化制备苯酚的催化反应机理为线索,综述近年来金属基催化剂以及处于起步阶段的非金属催化剂的最新研究进展,着重从自由基机理和非自由基机理两个方面详细归纳分析催化剂的组成结构与其反应的活性和选择性之间的构效关系,并就该领域未来的发展动向及需要关注的问题给出了展望和建议,期望有助于深化对催化机理的认识,并为进一步研发更高活性和稳定性的苯羟基化催化剂提供有益借鉴。
关键词： 苯, 苯酚, 羟基化反应, 金属基催化剂, 非金属催化剂, 反应机理

Activation of C—H bond is one of the most important scientific topics in organic synthesis area. Hydroxylation of benzene to phenol with environmentally friendly oxidants like H2O2 and O2 is a challenge in this filed for tens of years, since it involves not only the fundamental issue of the $\text C_{\text s \text p^{2}}— \text H $ bond activation for benzene, but also other issues such as the activation of H2O2/O2, decomposition of H2O2, and deep oxidation of phenol product. More importantly, in the context of green chemical industry, this green process becomes more attractive due to the promising alternative to replace the current cumene route. In this review, recent researches on metal-based catalysts and newly emerging non-metal catalysts are summarized, clued by the catalytic reaction mechanism of hydroxylation of benzene to phenol. The structure-activity relationship between catalysts’ composition and structure with their reactive activity and selectivity is analyzed in detail based on radical and non-radical mechanisms. Outlook and suggestions on the further development of rational design of catalysts and deeper insights into reaction mechanism in this field are proposed. This review is hopefully to benefit the exploring of novel catalysts with higher activity and better stability for hydroxylation of benzene to phenol.

Contents

1 Introduction

2 Metal-based catalysts for hydroxylation of benzene

2.1 H2O2-mediated radical mechanism

2.2 H2O2-mediated non-radical mechanism

2.3 O2-mediated radical mechanism

2.4 O2-mediated non-radical mechanism

2.5 O2-mediated synergistic catalytic mechanism

3 Non-metal materials for catalyzing hydroxylation of benzene

3.1 Radical mechanism over carbon materials catalysts

3.2 Radical mechanism over polymers catalysts

4 Conclusion and outlook

Key words: benzene, phenol, hydroxylation reaction, metal-based catalysts, non-metal catalysts, reaction mechanism
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表1 不同反应机理的苯羟基化反应金属基催化剂的活性对比
Table 1 Comparison of activities of metal-based catalysts for hydroxylation of benzene via different reaction mechanism
Mechanism Catalyst Reaction condition Activitya ref
H2O2-mediated
radical		 NaVO3 C6H6 11.3 mmol, H2O2 19.4 mmol, catalyst 0.2 mmol, 25 ℃, 13 h Y 13.5%, S 94.0% 38
[Cu2(μ-OH)(6-hpa)](ClO4)3 C6H6 60 mmol, H2O2 120 mmol, catalyst 1 μmol,50 ℃, 40 h X 22.0%, S 95.2% 12
Fe(DS)3 C6H6 11.3 mmol, H2O2 11.3 mmol, catalyst 0.05 mmol,
50 ℃, 6 h		 Y 54.0%, S 100% 40
[Dmim]2.5PMoV C6H6 10 mmol, H2O2 30 mmol, catalyst 100 mg, 70 ℃, 4 h Y 26.5%, S 100% 25
[C3CNpy]4HPMoV2 C6H6 10 mmol, H2O2 30 mmol, catalyst 100 mg, 60 ℃, 2 h Y 31.4%, S 95.8% 27
P-[DVB-VBIM]5PMoV2 C6H6 10 mmol, H2O2 30 mmol, catalyst 100 mg, 55 ℃, 6 h Y 23.7%, S 100% 41
[VO(acac)2]-
grafted PMO		 C6H6 4 mmol, H2O2 12 mmol, catalyst 300 mg, 50 ℃, 8 h X 27.4%, S 100% 19
POM@OMP C6H6 6 mmol, H2O2 18 mmol, catalyst 50 mg, 80 ℃, 10 h Y 33.0%, S 100% 42
Cu2O-rGO C6H6 1 mmol, H2O2 2 mmol, catalyst 1 mg, 40 ℃, 12 h Y 21.2%, S 85.5% 22
FeOCl C6H6 10 mmol, H2O2 10 mmol, catalyst 100 mg, 60 ℃, 4 h Y 43.5%, S 100% 23
H2O2-mediated non-radical [NiⅡ(tepa)]2+ C6H6 5 μmol, H2O2 2.5 mmol, catalyst 0.5 μmol, 60 ℃, 5 h Y 21.0%, S 91.3% 43
[CoⅡ(L3)Cl]Ph4B C6H6 5 mmol, H2O2 25 mmol, catalyst 5 μmol, 60 ℃, 5 h Y 29.0%, S 97.0% 44
Fe-N4 C6H6 4.5 mmol, H2O2 55 mmol, catalyst 50 mg, 30 ℃, 24 h Y 78.4%, S 100% 45
V-Si-ZSM-22 C6H6 5 mmol, H2O2 5 mmol, catalyst 100 mg, 80 ℃, 30 s Y 30.8%, S> 99% 13
O2-mediated
radical		 VxOy@C-S C6H6 11.3 mmol, O2 3.0 MPa, catalyst 50 mg, ascorbic acid
0.8 g, 80 ℃, 4 h		 Y 9.3%, S 96.0% 9
V/UiO-66-NH2 C6H6 11.3 mmol, O2 3.0 MPa, catalyst 50 mg, ascorbic acid
0.7 g, 60 ℃, 21 h		 Y 22.0%, S 98.1% 46
VOC2O4-N-5 C6H6 11.3 mmol, O2 1.0 MPa, catalyst 100 mg, 150 ℃, 10 h X 4.2%, S 96.3% 47
O2-mediated non-radical H7PMo8V4O40 C6H6 2 mmol, Air 1.5 MPa, catalyst 55 mg, CO 0.5 MPa,
90 ℃, 15 h		 Y 28.1%, S 59.3% 28
POM@MOF@SBA-15 C6H6 10 mmol, O2 2.0 MPa, catalyst 200 mg,ascorbic acid
0.9 g, 80 ℃, 20 min		 Y 6.0%, S> 99% 48
PMoV@PCIF-1 C6H6 22.5 mmol, O2 2.0 MPa, catalyst 300 mg, ascorbic acid 0.8 g, 100 ℃, 10 h Y 12.0%, S 100% 49
PdII(bpym) C6H6 5.6 mmol, O2 2.0 MPa, catalyst 0.02 mmol,Al(OTf)3 0.04 mmol, 100 ℃, 16 h Y 3.7%, S 79.7% 31
H5PV2Mo10O40 C6H6 0.5 mmol, O2 1.0 MPa, catalyst 800 mg, 50% H2SO4
5 mL, 170 ℃, 6 h		 X 65.0%, S 95.0% 50
O2-mediated synergistic catalysis HMS-HPA(V2)+
Pd(OAc)2		 C6H6 22.5 mmol, O2 2.0 MPa, catalyst 500 mg+10 mg, LiOAc 0.2 g, 120 ℃, 10 h X 12.2%, S 75.6% 29
C3N4(580)+PMoV2 C6H6 45 mmol, O2 2.0 MPa, catalyst 100 mg+400 mg, LiOAc 0.6 g, 130 ℃, 4.5 h Y 13.6%, S 100% 26
g-C3N4+Ch5PMoV2 C6H6 5 mmol, O2 2.0 MPa, catalyst 12 mg+30 mg,LiOAc
0.06 g, 120 ℃, 4.5 h		 Y 10.7%, S> 99% 51
SFNC(800)+Ch5PMoV2 C6H6 5 mmol, O2 2.0 MPa, catalyst 10 mg+30 mg,LiOAc
0.06 g, 120 ℃, 3 h		 Y 11.2%, S> 99% 52
[DiBimCN]2HPMoV2
@NC580		 C6H6 45 mmol, O2 2.2 MPa, catalyst 550 mg, LiOAc
0.6 g,140 ℃, 17 h		 Y 10.5%, S 100% 53
FeC(5) C6H6 45 mmol, O2 2.2 MPa, catalyst 200 mg,LiOAc 0.6 g,
150 ℃, 30 h		 Y 14.2%, S 100% 54
图1 H2O2为氧化剂的金属基催化剂催化苯羟基化反应的自由基反应机理
Fig. 1 Radical reaction mechanism catalyzed by metal-based catalysts for the hydroxylation of benzene to phenol with H2O2
图2 双核铜配合物活化H2O2和催化苯羟基化反应的自由基机理[12]
Fig. 2 Radical mechanism of H2O2 activation and benzene hydroxylation catalyzed by dicopper core[12]
图3 Cu2O-rGO催化的苯羟基化反应的自由基机理[22]
Fig. 3 Radical mechanism of benzene hydroxylation over the Cu2O-rGO catalyst[22]
图4 非均相FeOCl催化的苯羟基化的自由基机理[23]
Fig. 4 Illustration of benzene hydroxylation of radical mechanism using heterogeneous FeOCl[23]
图5 H2O2在过渡金属活化下产生羟基自由基的一般过程
Fig. 5 The general process for generation of hydroxyl radical from H2O2 activated by transition metal catalysts
图6 一种典型的双氧水为氧化剂的苯羟基化非自由基反应机理
Fig. 6 A typical non-radical reaction mechanism for hydroxylation of benzene with H2O2
图7 [NiⅡ(tepa)]2+引导的亲电取代氧化反应机理[43]
Fig. 7 Proposed catalytic mechanism of electrophilic substitution catalyzed by [NiⅡ(tepa)]2+[43]
图8 V-Si-ZSM-22催化剂的结构及其催化苯羟基化的反应路径[13]:(a)结构和反应机理;(b)物种D异裂后亲核氧化芳烃生成苯酚
Fig. 8 Structure and reaction path of V-Si-ZSM-22 in the hydroxylation of arenes[13]: (a) Structure and proposed reaction mechanism; (b) Heterolysis of species D and nucleophilic interaction with arene to produce phenol
图9 O2为氧化剂的苯羟基化反应的自由基反应机理: (a)过程中生成H2O2[1];(b)过程中未生成H2O2
Fig. 9 Radical mechanism for the hydroxylation of benzene with O2: (a) H2O2 is formed during the reaction[1]; (b) No H2O2 is formed during the reaction
图10 氧气为氧化剂的苯羟基化的超氧自由基机理[47]
Fig. 10 Superoxide radical mechanism for the hydroxylation of benzene with O2[47]
图11 牺牲性还原剂条件下的O2为氧化剂苯羟基化反应的反应机理
Fig. 11 Reaction mechanism for the hydroxylation of benzene with O2 under sacrificial reducing agent
图12 H5PV2Mo10O40在无牺牲性还原剂条件下氧化苯环生成苯酚的可能途径[50]
Fig. 12 Possible pathway for hydroxylation of benzene to phenol by H5PV2Mo10O40 in the absence of sacrificial reducing agent[50]
图13 C3N4-PMoV2催化液相氧气氧化苯制苯酚的双活性中心催化机理[26]
Fig. 13 Dual-catalysis mechanism for C3N4-PMoV2 catalyzed aerobic oxidation of benzene to phenol[26]
表2 非金属材料催化的苯羟基化反应活性对比
Table 2 Comparison of activities of non-metal catalysts for hydroxylation of benzene
Catalyst Reaction condition Activitya ref
CCG C6H6 1.67 mmol, H2O2 22.5 mmol, catalyst 20 mg,60 ℃, 16 h X 18.5%, S 99% 11
MWCNTs C6H6 11.3 mmol, H2O2 13.5 mmol, catalyst 50 mg,60 ℃, 2.5 h X 7.0%, S 97% 83
CNT7000 C6H6 11.3 mmol, H2O2 22.5 mmol, catalyst 100 mg, 60 ℃, 36 h Y 13.7% 84
HPC-400 C6H6 130 g, H2O2 22.5 mmol, catalyst 20 mg, 60 ℃, 16 h X 4.1%, S 99% 85
WAC-0.5N-8H C6H6 22.5 mmol, H2O2 58.8 mmol, catalyst 600 mg, 70 ℃, 6 h Y 13.5%, S 86.3% 86
NOC-0.15 C6H6 45 mmol, O2 2.2 MPa, catalyst 200 mg,LiOAc 0.6 g, 150 ℃, 48 h Y 12.5%, S>99% 72
AC-70 C6H6 45 mmol, O2 2.2 MPa, catalyst 200 mg, LiOAc 0.6 g, 155 ℃, 36 h Y 10.1%, S 100% 87
QAP C6H6 5.7 mmol, O2 2.0 MPa, catalyst 100 mg, LiOAc 0.4 g, 120 ℃, 12 h Y 15.9%, S>99% 88
图14 双氧水为氧化剂的CCG上的苯羟基化反应机理[11]
Fig. 14 The proposed mechanism of the oxidation of benzene with H2O2 on CCG[11]
图15 双氧水为氧化剂的活性炭催化苯羟基化反应路径[86]
Fig. 15 Reaction pathway for the hydroxylation of benzene over activated carbon with H2O2[86]
图16 氧气为氧化剂的NOCs碳材料催化苯羟基化的路径[72]
Fig. 16 Reaction pathway for NOCs carbon-catalyzed hydroxylation of benzene to phenol with O2[72]
附表 催化剂缩写的英文全称说明
Supplementary Table Abbreviation for catalyst and corresponding English full name
Abbreviation for catalysta English full name
AC activated carbon
bpym 2,2'-bipyrimidine
C3CNpy N-butyronitrile pyridine
CCG chemically converted graphene
CNT carbon nanotube
Dmim 1,1-(butane-1,4-diyl)-bis(3-
methylimidazolium)
DiBimCN 4,4'-butyl-bis(3-cyanopropyl-imidazole)
Fe(DS)3 Ferric tri(dodecane sulfonate)
6-hpa 1,2-bis[2-[bis(2-pyridylmethyl)aminomethyl] -6-pyridyl]ethane
HMS hexagaonal mesoporous silica
HPA heteropolyacid
HPC honeycomb-like porous carbon
L3 N1,N1-bis((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-N3,N3-dimethylpropane-1,
3-diamine
MOF metal organic framework
MWCNTs multi-walled carbon nanotubes
NOC N-doped and surface
O-enriched mesoporous carbons
OMP ordered mesoporous polymer
P-DVB-VBIM poly divinylbenzene- 3-n-butyl-
1-vinylimidazolium
PMoV H3+xPMo12-xVxO40
PMO periodic mesoporous organosilica
POM polyoxometalate
PCIF porous cationic framework
QAP quinone-amine polymer
rGO reduced graphene oxide
SNFC soybean flour prepared nitrogen-doped carbon
tepa tris[2-(pyridin-2-yl)ethyl]amine
V-Si-ZSM V-containing all-silica zeolite
WAC wood-based activated carbon
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