• 综述 •
张明珏, 凡长坡, 王龙, 吴雪静, 周瑜, 王军. 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[J]. 化学进展, 2022, 34(5): 1026-1041.
Mingjue Zhang, Changpo Fan, Long Wang, Xuejing Wu, Yu Zhou, Jun Wang. Catalytic Reaction Mechanism for Hydroxylation of Benzene to Phenol with H2O2/O2 as Oxidants[J]. Progress in Chemistry, 2022, 34(5): 1026-1041.
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。
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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% | |
[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% | ||
Fe(DS)3 | C6H6 11.3 mmol, H2O2 11.3 mmol, catalyst 0.05 mmol, 50 ℃, 6 h | Y 54.0%, S 100% | ||
[Dmim]2.5PMoV | C6H6 10 mmol, H2O2 30 mmol, catalyst 100 mg, 70 ℃, 4 h | Y 26.5%, S 100% | ||
[C3CNpy]4HPMoV2 | C6H6 10 mmol, H2O2 30 mmol, catalyst 100 mg, 60 ℃, 2 h | Y 31.4%, S 95.8% | ||
P-[DVB-VBIM]5PMoV2 | C6H6 10 mmol, H2O2 30 mmol, catalyst 100 mg, 55 ℃, 6 h | Y 23.7%, S 100% | ||
[VO(acac)2]- grafted PMO | C6H6 4 mmol, H2O2 12 mmol, catalyst 300 mg, 50 ℃, 8 h | X 27.4%, S 100% | ||
POM@OMP | C6H6 6 mmol, H2O2 18 mmol, catalyst 50 mg, 80 ℃, 10 h | Y 33.0%, S 100% | ||
Cu2O-rGO | C6H6 1 mmol, H2O2 2 mmol, catalyst 1 mg, 40 ℃, 12 h | Y 21.2%, S 85.5% | ||
FeOCl | C6H6 10 mmol, H2O2 10 mmol, catalyst 100 mg, 60 ℃, 4 h | Y 43.5%, S 100% | ||
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% | |
[CoⅡ(L3)Cl]Ph4B | C6H6 5 mmol, H2O2 25 mmol, catalyst 5 μmol, 60 ℃, 5 h | Y 29.0%, S 97.0% | ||
Fe-N4 | C6H6 4.5 mmol, H2O2 55 mmol, catalyst 50 mg, 30 ℃, 24 h | Y 78.4%, S 100% | ||
V-Si-ZSM-22 | C6H6 5 mmol, H2O2 5 mmol, catalyst 100 mg, 80 ℃, 30 s | Y 30.8%, S> 99% | ||
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% | |
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% | ||
VOC2O4-N-5 | C6H6 11.3 mmol, O2 1.0 MPa, catalyst 100 mg, 150 ℃, 10 h | X 4.2%, S 96.3% | ||
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% | |
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% | ||
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% | ||
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% | ||
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% | ||
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% | |
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% | ||
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% | ||
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% | ||
[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% | ||
FeC(5) | C6H6 45 mmol, O2 2.2 MPa, catalyst 200 mg,LiOAc 0.6 g, 150 ℃, 30 h | Y 14.2%, S 100% |
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% | |
MWCNTs | C6H6 11.3 mmol, H2O2 13.5 mmol, catalyst 50 mg,60 ℃, 2.5 h | X 7.0%, S 97% | |
CNT7000 | C6H6 11.3 mmol, H2O2 22.5 mmol, catalyst 100 mg, 60 ℃, 36 h | Y 13.7% | |
HPC-400 | C6H6 130 g, H2O2 22.5 mmol, catalyst 20 mg, 60 ℃, 16 h | X 4.1%, S 99% | |
WAC-0.5N-8H | C6H6 22.5 mmol, H2O2 58.8 mmol, catalyst 600 mg, 70 ℃, 6 h | Y 13.5%, S 86.3% | |
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% | |
AC-70 | C6H6 45 mmol, O2 2.2 MPa, catalyst 200 mg, LiOAc 0.6 g, 155 ℃, 36 h | Y 10.1%, S 100% | |
QAP | C6H6 5.7 mmol, O2 2.0 MPa, catalyst 100 mg, LiOAc 0.4 g, 120 ℃, 12 h | Y 15.9%, S>99% |
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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