超临界反应及超临界流体参与的反应研究与应用进展

doi:10.11949/0438-1157.20240601

化工学报 ›› 2024, Vol. 75 ›› Issue (11): 3973-3986.DOI: 10.11949/0438-1157.20240601

超临界反应及超临界流体参与的反应研究与应用进展

王永涛¹^,²(), 毛建拥³, 胡柏剡⁴, 王欣雨¹, 刘佳欣¹, 姚加¹^,², 李浩然¹^,²()

^1.浙江大学化学系，浙江杭州 310058
^2.浙江大学化学前瞻技术研究中心，浙江杭州 310058
^3.山东新和成维生素有限公司，山东潍坊 261108
^4.浙江新和成股份有限公司，浙江绍兴 312500

收稿日期:2024-06-03 修回日期:2024-08-25 出版日期:2024-11-25 发布日期:2024-12-26
通讯作者: 李浩然
作者简介:王永涛（1990—），男，博士，副研究员，wyongtao@zju.edu.cn
基金资助:
国家重点研发计划项目(2022YFA1503200);国家自然科学基金项目(22303079);浙江省自然科学基金项目(LQ22B030011)

Progress in supercritical reactions and supercritical fluid participated reactions and their applications

Yongtao WANG¹^,²(), Jianyong MAO³, Baishan HU⁴, Xinyu WANG¹, Jiaxin LIU¹, Jia YAO¹^,², Haoran LI¹^,²()

^1.Department of Chemistry, Zhejiang University, Hangzhou 310058, Zhejiang, China
^2.Center of Chemistry for Frontier Technologies, Zhejiang University, Hangzhou 310058, Zhejiang, China
^3.Shandong NHU Vitamin Ltd. , Weifang 261108, Shandong, China
^4.Zhejiang NHU Company Ltd. , Shaoxing 312500, Zhejiang, China

Received:2024-06-03 Revised:2024-08-25 Online:2024-11-25 Published:2024-12-26
Contact: Haoran LI

摘要/Abstract

摘要：

物质在超临界条件下有独特的性质与反应活性，常被用作为超临界反应介质，但作为反应物被实际应用于化工反应的例子并不多见。聚焦于至少一种反应物处于超临界条件的反应，总结其在一些具有化工实践价值反应中的应用，特别关注所有反应物均处于超临界状态时超临界反应的基础研究及工业应用，并展望了该技术未来的研究方向与发展前景。

关键词: 超临界流体, 超临界反应, 绿色化工技术

Abstract:

Substances have unique properties and reactivity under supercritical reactions and are often used as supercritical reaction media, but there are few examples of them being actually used as reactants in chemical reactions.This paper focuses on reactions where at least one reactant is a supercritical fluid, summarizing their applications in some industrially valuable reactions. This review particularly emphasizes the fundamental research and industrial applications of supercritical reactions where all reactants are in a supercritical state, while also looking ahead to future research directions and prospects for this technology.

Key words: supercritical fluid, supercritical reaction, green chemical technology

中图分类号:

TQ 02

王永涛, 毛建拥, 胡柏剡, 王欣雨, 刘佳欣, 姚加, 李浩然. 超临界反应及超临界流体参与的反应研究与应用进展[J]. 化工学报, 2024, 75(11): 3973-3986.

Yongtao WANG, Jianyong MAO, Baishan HU, Xinyu WANG, Jiaxin LIU, Jia YAO, Haoran LI. Progress in supercritical reactions and supercritical fluid participated reactions and their applications[J]. CIESC Journal, 2024, 75(11): 3973-3986.

图/表 15

图1 超临界醇等物质在生物柴油制备中的应用

Fig. 1 Application of supercritical substrates in biodiesel production

图2 超临界醇参与的不饱和烃转移氢化反应

Fig.2 Transfer hydrogenations of unsaturated hydrocarbon compounds by supercritical alcohols

图3 超临界醇参与的硝基转移氢化反应

Fig.3 Transfer hydrogenations of nitrocompounds by supercritical isopropyl alcohol

图4 超临界二氧化碳的异相催化还原反应

Fig.4 Heterogeneous catalytic reduction of supercritical CO2

图5 超临界二氧化碳与不饱和烃的反应

Fig.5 Reaction of supercritical CO2 with unsaturated hydrocarbon compounds

图6 超临界二氧化碳参与的聚合反应

Fig.6 Polymerization in appearance of supercritical CO2

图7 超临界正丁烷异构化的实验装置示意图（其中P1为正丁烷泵，V5为压力控制阀，R为反应器，GC为气相色谱仪）[75]

Fig.7 The schematic diagram of the experimental setup for isomerization of supercritical n-butane (P1: n-butane pump; V5: pressure control valve; R: reactor; GC: gas chromatograph) [75]

图8 超临界甲醇的析氢反应

Fig.8 Dehydrogenation of supercritical methanol

图9 丙酮通过自缩合反应生成异佛尔酮

Fig.9 Production of isophorone from acetone via aldol reaction

图10 超临界丙酮自缩合的实验装置示意图[91]

Fig.10 Schematic diagram of the experimental setup for self-condensation of supercritical acetone[91]

图11 超临界丙酮与甲醛的缩合反应

Fig. 11 Reactions between supercritical acetone and formaldehyde

图12 超临界异丁烯与甲醛的Prins反应

Fig. 12 Prins reaction between supercritical isobutylene and formaldehyde

图13 超临界条件提高涉及连串副反应体系选择性的机理

Fig.13 Mechanism for improving the selectivity under supercritical conditions

图14 超临界反应在新和成的工业化应用

Fig. 14 Industrialization of supercritical reactions in NHU

图15 维生素E生产中涉及的超临界反应

Fig.15 Supercritical reactions involved in manufacturing of vitamin E

参考文献 118

1	Dias A L B, Hatami T, Martínez J, et al. Biocatalytic production of isoamyl acetate from fusel oil in supercritical CO₂ [J]. The Journal of Supercritical Fluids, 2020, 164: 104917.
2	Savage P E, Gopalan S, Mizan T I, et al. Reactions at supercritical conditions: applications and fundamentals[J]. AIChE Journal, 1995, 41(7): 1723-1778.
3	Brunner G. Applications of supercritical fluids[J]. Annual Review of Chemical and Biomolecular Engineering, 2010, 1: 321-342.
4	Kusdiana D, Saka S. Kinetics of transesterification in rapeseed oil to biodiesel fuel as treated in supercritical methanol[J]. Fuel, 2001, 80(5): 693-698.
5	Glišić S B, Skala D U. Phase transition at subcritical and supercritical conditions of triglycerides methanolysis[J]. The Journal of Supercritical Fluids, 2010, 54(1): 71-80.
6	Saka S, Kusdiana D. Biodiesel fuel from rapeseed oil as prepared in supercritical methanol[J]. Fuel, 2001, 80(2): 225-231.
7	Demirbaş A. Biodiesel from vegetable oils via transesterification in supercritical methanol[J]. Energy Conversion and Management, 2002, 43(17): 2349-2356.
8	Song E S, Lim J W, Lee H S, et al. Transesterification of RBD palm oil using supercritical methanol[J]. The Journal of Supercritical Fluids, 2008, 44(3): 356-363.
9	Tan K T, Lee K T, Mohamed A R. Production of FAME by palm oil transesterification via supercritical methanol technology[J]. Biomass and Bioenergy, 2009, 33(8): 1096-1099.
10	Demir V, Akgün M. Investigation of Jatropha oil transesterification into methyl esters under supercritical methanol environment using advanced heterogeneous catalysts[J]. ChemistrySelect, 2024, 9(7): e202304678.
11	Kusdiana D, Saka S. Effects of water on biodiesel fuel production by supercritical methanol treatment[J]. Bioresource Technology, 2004, 91(3): 289-295.
12	Kusdiana D, Saka S. Methyl esterification of free fatty acids of rapeseed oil as treated in supercritical methanol[J]. Journal of Chemical Engineering of Japan, 2001, 34(3): 383-387.
13	Anikeev V I, Yakovleva E Y. Biodiesel synthesis from vegetable oils with supercritical methanol[J]. The Journal of Supercritical Fluids, 2013, 77: 100-102.
14	He H Y, Wang T, Zhu S L. Continuous production of biodiesel fuel from vegetable oil using supercritical methanol process[J]. Fuel, 2007, 86(3): 442-447.
15	Zhou C, Wang C W, Wang W G, et al. Continuous production of biodiesel from soybean oil using supercritical methanol in a vertical tubular reactor: I. Phase holdup and distribution of intermediate product along the axial direction[J]. Chinese Journal of Chemical Engineering, 2010, 18(4): 626-629.
16	Silva C, Weschenfelder T A, Rovani S, et al. Continuous production of fatty acid ethyl esters from soybean oil in compressed ethanol[J]. Industrial & Engineering Chemistry Research, 2007, 46(16): 5304-5309.
17	Vieitez I, da Silva C, Borges G R, et al. Continuous production of soybean biodiesel in supercritical ethanol-water mixtures[J]. Energy & Fuels, 2008, 22(4): 2805-2809.
18	Gui M M, Lee K T, Bhatia S. Supercritical ethanol technology for the production of biodiesel: process optimization studies[J]. The Journal of Supercritical Fluids, 2009, 49(2): 286-292.
19	Saka S, Isayama Y. A new process for catalyst-free production of biodiesel using supercritical methyl acetate[J]. Fuel, 2009, 88(7): 1307-1313.
20	Goembira F, Matsuura K, Saka S. Biodiesel production from rapeseed oil by various supercritical carboxylate esters[J]. Fuel, 2012, 97: 373-378.
21	Tan K T, Lee K T, Mohamed A R. A glycerol-free process to produce biodiesel by supercritical methyl acetate technology: an optimization study via response surface methodology[J]. Bioresource Technology, 2010, 101(3): 965-969.
22	Tan K T, Lee K T, Mohamed A R. Prospects of non-catalytic supercritical methyl acetate process in biodiesel production[J]. Fuel Processing Technology, 2011, 92(10): 1905-1909.
23	Ilham Z, Saka S. Two-step supercritical dimethyl carbonate method for biodiesel production from Jatropha curcas oil[J]. Bioresource Technology, 2010, 101(8): 2735-2740.
24	Ilham Z, Saka S. Dimethyl carbonate as potential reactant in non-catalytic biodiesel production by supercritical method[J]. Bioresource Technology, 2009, 100(5): 1793-1796.
25	Tan K T, Lee K T, Mohamed A R. Optimization of supercritical dimethyl carbonate (SCDMC) technology for the production of biodiesel and value-added glycerol carbonate[J]. Fuel, 2010, 89(12): 3833-3839.
26	Farobie O, Yanagida T, Matsumura Y. New approach of catalyst-free biodiesel production from canola oil in supercritical tert-butyl methyl ether (MTBE)[J]. Fuel, 2014, 135: 172-181.
27	Klepáčová K, Mravec D, Kaszonyi A, et al. Etherification of glycerol and ethylene glycol by isobutylene[J]. Applied Catalysis A: General, 2007, 328(1): 1-13.
28	Frusteri F, Arena F, Bonura G, et al. Catalytic etherification of glycerol by tert-butyl alcohol to produce oxygenated additives for diesel fuel[J]. Applied Catalysis A: General, 2009, 367(1/2): 77-83.
29	Farobie O, Matsumura Y. Effectiveness of spiral reactor for biodiesel production using supercritical t-butyl methyl ether (MTBE)[J]. Journal of the Japan Petroleum Institute, 2015, 58(2): 110-117.
30	Gubin S P, Men’shov V I, Kirilets V M, et al. Hydrogenation of multiple bonds using isopropyl alcohol without a catalyst[J]. Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science, 1983, 32(12): 2547.
31	Nakagawa T, Ozaki H, Kamitanaka T, et al. Reactions of supercritical alcohols with unsaturated hydrocarbons[J]. The Journal of Supercritical Fluids, 2003, 27(3): 255-261.
32	Kamitanaka T, Yamamoto K, Matsuda T, et al. Transformation of benzonitrile into benzyl alcohol and benzoate esters in supercritical alcohols[J]. Tetrahedron, 2008, 64(24): 5699-5702.
33	Formenti D, Ferretti F, Scharnagl F K, et al. Reduction of nitro compounds using 3d-non-noble metal catalysts[J]. Chemical Reviews, 2019, 119(4): 2611-2680.
34	Matsunami A, Kayaki Y. Upgrading and expanding the scope of homogeneous transfer hydrogenation[J]. Tetrahedron Letters, 2018, 59(6): 504-513.
35	Sivcev V P, Volcho K P, Salakhutdinov N F, et al. Unusual transformations of aliphatic nitro compounds in a flow reactor in high-pressure isopropanol on alumina (Part 2): Formation of esters[J]. The Journal of Supercritical Fluids, 2016, 107: 179-181.
36	Sivcev V P, Volcho K P, Salakhutdinov N F, et al. Unique shortening of carbon chain during reduction of aliphatic nitro compounds to amines in the presence of supercritical isopropanol on alumina[J]. The Journal of Supercritical Fluids, 2015, 103: 101-104.
37	Anikeev V I, Sivcev V P, Valeev K R, et al. Highly selective reduction of nitroarenes by sc-isopropanol in the presence of zirconia in a flow reactor[J]. The Journal of Supercritical Fluids, 2018, 140: 233-237.
38	Sun Z H, Bottari G, Barta K. Supercritical methanol as solvent and carbon source in the catalytic conversion of 1, 2-diaminobenzenes and 2-nitroanilines to benzimidazoles[J]. Green Chemistry, 2015, 17(12): 5172-5181.
39	Barta K, Ford P C. Catalytic conversion of nonfood woody biomass solids to organic liquids[J]. Accounts of Chemical Research, 2014, 47(5): 1503-1512.
40	McClelland D J, Galebach P H, Motagamwala A H, et al. Supercritical methanol depolymerization and hydrodeoxygenation of lignin and biomass over reduced copper porous metal oxides[J]. Green Chemistry, 2019, 21(11): 2988-3005.
41	Li R D, Li B S, Kai X P, et al. Hydro-liquefaction of rice stalk in supercritical ethanol with in situ generated hydrogen[J]. Fuel Processing Technology, 2017, 167: 363-370.
42	Limarta S O, Ha J M, Park Y K, et al. Efficient depolymerization of lignin in supercritical ethanol by a combination of metal and base catalysts[J]. Journal of Industrial and Engineering Chemistry, 2018, 57: 45-54.
43	Ai L H, Su J F, Wang M, et al. Bamboo-structured nitrogen-doped carbon nanotube coencapsulating cobalt and molybdenum carbide nanoparticles: an efficient bifunctional electrocatalyst for overall water splitting[J]. ACS Sustainable Chemistry & Engineering, 2018, 6(8): 9912-9920.
44	Regmi Y N, Mann J K, McBride J R, et al. Catalytic transfer hydrogenolysis of organosolv lignin using B-containing FeNi alloyed catalysts[J]. Catalysis Today, 2018, 302: 190-195.
45	Galebach P H, Thompson S, Wittrig A M, et al. Investigation of the reaction pathways of biomass-derived oxygenate conversion into monoalcohols in supercritical methanol with CuMgAl-mixed-metal oxide[J]. ChemSusChem, 2018, 11(23): 4007-4017.
46	Galebach P, McClelland D J, Eagan N M, et al. Production of alcohols from cellulose by supercritical methanol depolymerization and hydrodeoxygenation[J]. ACS Sustainable Chemistry & Engineering, 2018, 6(3): 4330-4344.
47	Chibiryaev A M, Kozhevnikov I V, Shalygin A S, et al. Transformation of petroleum asphaltenes in supercritical alcohols studied via FTIR and NMR techniques[J]. Energy & Fuels, 2018, 32(2): 2117-2127.
48	Sarkar B, Kwek W, Verma D, et al. Effective vacuum residue upgrading using sacrificial nickel(Ⅱ) dimethylglyoxime complex in supercritical methanol[J]. Applied Catalysis A: General, 2017, 545: 148-158.
49	Riaz A, Verma D, Zeb H, et al. Solvothermal liquefaction of alkali lignin to obtain a high yield of aromatic monomers while suppressing solvent consumption[J]. Green Chemistry, 2018, 20(21): 4957-4974.
50	Kim J Y, Park J, Kim U J, et al. Conversion of lignin to phenol-rich oil fraction under supercritical alcohols in the presence of metal catalysts[J]. Energy & Fuels, 2015, 29(8): 5154-5163.
51	Kim J Y, Oh S, Hwang H, et al. Effects of various reaction parameters on solvolytical depolymerization of lignin in sub- and supercritical ethanol[J]. Chemosphere, 2013, 93(9): 1755-1764.
52	Xu X M, Zhang C S, Zhai Y P, et al. Upgrading of bio-oil using supercritical 1-butanol over a Ru/C heterogeneous catalyst: role of the solvent[J]. Energy & Fuels, 2014, 28(7): 4611-4621.
53	Jessop P G, Ikariya T, Noyori R. Homogeneous catalytic hydrogenation of supercritical carbon dioxide[J]. Nature, 1994, 368: 231-233.
54	Jessop P G, Hsiao Y, Ikariya T, et al. Homogeneous catalysis in supercritical fluids: hydrogenation of supercritical carbon dioxide to formic acid, alkyl formates, and formamides[J]. Journal of the American Chemical Society, 1996, 118(2): 344-355.
55	Bogdan V I, Koklin A E, Nikolaev S A, et al. Carbon dioxide hydrogenation on Au nanoparticles supported on TiO₂, ZrO₂ and sulfated ZrO₂ under supercritical conditions[J]. Topics in Catalysis, 2016, 59(13): 1104-1109.
56	Pokusaeva Y A, Koklin A E, Lunin V V, et al. CO₂ hydrogenation on Fe-based catalysts doped with potassium in gas phase and under supercritical conditions[J]. Mendeleev Communications, 2019, 29(4): 382-384.
57	Pokusaeva Y A, Koklin A E, Eliseev O L, et al. Hydrogenation of carbon oxides over the Fe-based catalysts on the carbon support[J]. Russian Chemical Bulletin, 2020, 69(2): 237-240.
58	Iijima T, Yamaguchi T. Efficient regioselective carboxylation of phenol to salicylic acid with supercritical CO₂ in the presence of aluminium bromide[J]. Journal of Molecular Catalysis A: Chemical, 2008, 295(1/2): 52-56.
59	Iijima T, Yamaguchi T. K₂CO₃-catalyzed direct synthesis of salicylic acid from phenol and supercritical CO₂ [J]. Applied Catalysis A: General, 2008, 345(1): 12-17.
60	Isaacs N S, O’Sullivan B, Verhaelen C. High pressure routes to dimethyl carbonate from supercritical carbon dioxide[J]. Tetrahedron, 1999, 55(40): 11949-11956.
61	Li F W, Suo Q L, Hong H L, et al. DBU and copper(Ⅰ) mediated carboxylation of terminal alkynes using supercritical CO₂ as a reactant and solvent[J]. Tetrahedron Letters, 2014, 55(29): 3878-3880.
62	Kayaki Y, Yamamoto M, Suzuki T, et al. Carboxylative cyclization of propargylamines with supercritical carbon dioxide[J]. Green Chemistry, 2006, 8(12): 1019-1021.
63	Yuan D D, Bao J X, Ren Y, et al. Synthesis of nylon 1 in supercritical carbon dioxide and its crystallization behavior effect on nylon 11[J]. CrystEngComm, 2018, 20(32): 4676-4684.
64	Zhang Z Y, Huang K J, Liu Z H. Synthesis of high molecular weight nylon 46 in supercritical carbon dioxide[J]. Macromolecules, 2011, 44(4): 820-825.
65	Ihata O, Kayaki Y, Ikariya T. Synthesis of thermoresponsive polyurethane from 2-methylaziridine and supercritical carbon dioxide[J]. Angewandte Chemie International Edition, 2004, 43(6): 717-719.
66	Bogdan V I, Kustov A L, Glukhov L M, et al. Catalytic oxidative coupling of dimethyl ether under supercritical conditions[J]. Russian Journal of Physical Chemistry B, 2013, 7(7): 810-813.
67	Yakaboylu O, Harinck J, Smit K, et al. Supercritical water gasification of biomass: a literature and technology overview[J]. Energies, 2015, 8(2): 859-894.
68	Resende F L P, Savage P E. Kinetic model for noncatalytic supercritical water gasification of cellulose and lignin[J]. AIChE Journal, 2010, 56(9): 2412-2420.
69	Man X, Okuda K, Ohara S, et al. Disassembly of organosolv lignin in supercritieal fluid-phenol as a suppressor for repolymerization [J]. Journal of the Japan Institute of Energy, 2005, 84(6): 486-490.
70	DiLeo G J, Neff M E, Savage P E. Gasification of guaiacol and phenol in supercritical water[J]. Energy & Fuels, 2007, 21(4): 2340-2345.
71	Huelsman C M, Savage P E. Reaction pathways and kinetic modeling for phenol gasification in supercritical water[J]. The Journal of Supercritical Fluids, 2013, 81: 200-209.
72	Bogdan V I, Kondratyuk A V, Koklin A E, et al. Interaction of phenol and cyclohexanol with supercritical water[J]. Russian Journal of Physical Chemistry B, 2017, 11(7): 1207-1213.
73	Saim S, Subramaniam B. Isomerization of 1-hexene over Pt/γ-Al₂O₃ catalyst: reaction mixture density and temperature effects on catalyst effectiveness factor, coke laydown, and catalyst micromeritics[J]. Journal of Catalysis, 1991, 131(2): 445-456.
74	Saim S, Subramaniam B. Isomerization of 1-hexene on Pt/γ-Al₂O₃ catalyst at subcritical and supercritical reaction conditions: pressure and temperature effects on catalyst activity[J]. The Journal of Supercritical Fluids, 1990, 3(4): 214-221.
75	Sander B, Thelen M, Kraushaar-Czarnetzki B. Non-corrosive and chlorine-free isomerisation process under supercritical conditions[J]. Catalysis Today, 2002, 75(1/2/3/4): 119-124.
76	Bogdan V I, Koklin A E, Kazanskii V B. Gas-phase and supercritical n-pentane isomerization on H-mordenite[J]. Kinetics and Catalysis, 2007, 48(6): 785-788.
77	Bogdan V I, Koklin A E, Kazanskii V B. Catalytic activity of H-forms of zeolites in the isomerization of supercritical n-pentane and their physicochemical properties[J]. Kinetics and Catalysis, 2010, 51(5): 736-742.
78	Bogdan V I, Koklin A E, Pokusaeva Y A, et al. The transformation of n-alkanes on H-forms of zeolites under supercritical conditions[J]. Russian Journal of Physical Chemistry B, 2010, 4(7): 1085-1091.
79	Wu L B, Li B L, Zhao C. Direct synthesis of hydrogen and dimethoxylmethane from methanol on copper/silica catalysts with optimal Cu⁺/Cu⁰ sites[J]. ChemCatChem, 2018, 10(5): 1140-1147.
80	Park J Y, Jeon W, Lee J H, et al. Effects of supercritical fluids in catalytic upgrading of biomass pyrolysis oil[J]. Chemical Engineering Journal, 2019, 377: 120312.
81	Teplý J, Janovský I, Habersbergerová A, et al. The radiolysis of alcohols at low temperatures (Ⅱ): The precursors of hydrogen in glassy alcohols up to n-hexanol including allyl alcohol. The hydrogen formation in irradiated glassy alcohols at 77 K[J]. International Journal for Radiation Physics and Chemistry, 1970, 2(1): 21-30.
82	Mishanin I I, Bogdan V I. Advantages of ethane oxidative dehydrogenation on the MoVNbTeO _x catalyst under elevated pressure[J]. Mendeleev Communications, 2019, 29(4): 455-457.
83	Mestres R. A green look at the aldol reaction[J]. Green Chemistry, 2004, 6(12): 583-603.
84	Liu L, Liu Z T, Liu Z W, et al. L-proline catalyzed aldol reactions between acetone and aldehydes in supercritical fluids: an environmentally friendly reaction procedure[J]. Science China Chemistry, 2010, 53(7): 1586-1591.
85	Hagiwara H, Hamaya J, Hoshi T, et al. Self-aldol condensation of unmodified aldehyde in supercritical carbon dioxide catalyzed by amine grafted on silica[J]. Tetrahedron Letters, 2005, 46(3): 393-395.
86	Stevens J G, Bourne R A, Poliakoff M. The continuous self aldol condensation of propionaldehyde in supercritical carbon dioxide: a highly selective catalytic route to 2-methylpentenal[J]. Green Chemistry, 2009, 11(3): 409-416.
87	Darda P J, Ranade V V. Isophorone reactor: modelling and performance enhancement[J]. Chemical Engineering Journal, 2012, 207: 349-367.
88	Krivtsov I, Faba L, Díaz E, et al. A new peroxo-route for the synthesis of Mg-Zr mixed oxides catalysts: application in the gas phase acetone self-condensation[J]. Applied Catalysis A: General, 2014, 477: 26-33.
89	Di Cosimo J I, Apesteguı́a C R. Study of the catalyst deactivation in the base-catalyzed oligomerization of acetone[J]. Journal of Molecular Catalysis A: Chemical, 1998, 130(1/2): 177-185.
90	Koklin A E, Hasyanova G M, Glukhov L M, et al. Acetone condensation over CaO-SnO₂ catalyst[J]. Russian Chemical Bulletin, 2017, 66(3): 488-490.
91	Mei J, Chen Z R, Yuan S F, et al. Kinetics of isophorone synthesis via self-condensation of supercritical acetone[J]. Chemical Engineering & Technology, 2016, 39(10): 1867-1874.
92	黄国东, 吕国锋, 刘祥洪. 超临界非催化合成4-羟基-2-丁酮[J]. 广州化工, 2013, 41(16):91-92.
	Huang G D, Lv G F, Liu X H. Non-catalytic synthesis of 4-hydroxy-2-butanone in supercritical conditions[J]. Guangzhou Chemical Industry, 2013, 41(16):91-92.
93	Mei J, Mao J Y, Chen Z R, et al. Mechanism and kinetics of 4-hydroxy-2-butanone formation from formaldehyde and acetone under supercritical conditions and in high-temperature liquid-phase[J]. Chemical Engineering Science, 2015, 131: 213-218.
94	Mikeska L A, Erving A. Unsaturated alcohols and process for the manufacture thereof: US2308192A[P]. 1939-10-31.
95	Standard Oil Dev. Co. An improved manufacture of unsaturated alcohols: GB545191A[P]. 1942-05-14.
96	李鹏, 张永振, 刘英俊, 等. 一种 3-甲基-3-丁烯-1-醇的制备方法: 103804145A[P]. 2014-01-23.
	Li P, Zhang Y Z, Liu Y J, et al. A method for the preparation of 3-methyl-3-buten-1-ol: 103804145A[P]. 2014-01-23.
97	Ji M, Li X F, Wang J H, et al. Grafting SnCl₄ catalyst as a novel solid acid for the synthesis of 3-methylbut-3-en-1-ol[J]. Catalysis Today, 2011, 173(1): 28-31.
98	Herbert M, Hermann O, Horst P. Production of alk-3-en-1-ols: CA850151A[P]. 1970-08-25.
99	Nagareda K, Yoshimura N. Production of gamma,delta-unsaturated alcohol: JPH07285899A[P]. 1994-04-18.
100	毛建拥, 陈志荣, 李浩然, 等. 一种由甲醛半缩醛合成 3-甲基-3-丁烯-1-醇的制备方法: 104130107A[P]. 2014-11-05.
	Mao J Y, Chen Z R, Li H R, et al. A method for the preparation of 3-methyl-3-buten-1-ol from formaldehyde hemiacetal: 104130107A[P]. 2014-11-05.
101	陈志荣, 万晓峰, 尹红, 等. 超临界异丁烯中无催化合成3-甲基-3-丁烯-1-醇的动力学研究[J]. 高校化学工程学报, 2018, 32(6): 1332-1337.
	Chen Z R, Wan X F, Yin H, et al. Reaction kinetics of 3-methyl-3-butene-1-ol synthesis in supercritical isobutylene without catalysts[J]. Journal of Chemical Engineering of Chinese Universities, 2018, 32(6): 1332-1337.
102	Chen Z, Yao Y, Yin H, et al. Reactivity of formaldehyde during 4-hydroxy-2-butanone synthesis in supercritical state[J]. ACS Omega, 2022, 7(48): 43450-43461.
103	Cockrell C, Brazhkin V V, Trachenko K. Transition in the supercritical state of matter: review of experimental evidence[J]. Physics Reports, 2021, 941: 1-27.
104	Mao S, Zhou T, Wei D, et al. Heat transfer characteristics of supercritical water in channels: a systematic literature review of 20 years of research[J]. Applied Thermal Engineering, 2021, 197: 117403.
105	Kalikin N N, Oparin R D, Kolesnikov A L, et al. A crossover of the solid substances solubility in supercritical fluids: what is it in fact?[J]. Journal of Molecular Liquids, 2021, 334: 115997.
106	Huber M L, Lemmon E W, Bell I H, et al. The NIST REFPROP database for highly accurate properties of industrially important fluids[J]. Industrial & Engineering Chemistry Research, 2022, 61(42): 15449-15472.
107	William B, Noémie P, Brigitte E, et al. Supercritical fluid methods: an alternative to conventional methods to prepare liposomes[J]. Chemical Engineering Journal, 2020, 383: 123106.
108	Park Y K, Ha J M, Oh S, et al. Bio-oil upgrading through hydrogen transfer reactions in supercritical solvents[J]. Chemical Engineering Journal, 2021, 404: 126527.
109	Sun J, Du M, Rong S, et al. Experimental study on optimizing reaction path for promoting the gasification of coal in supercritical water[J]. Fuel, 2023, 342: 127827.
110	Valizadeh S, Khani Y, Kang B S, et al. Catalytic conversion of guaiacol to phenol and alkylphenols over Mo-promoted Ni/CeO₂ catalyst in supercritical ethanol[J]. Applied Catalysis B: Environment and Energy, 2024, 348: 123823.
111	Lu B, Ge Z, Chen Y, et al. Study on supercritical water gasification reaction and kinetic of coal model compounds[J]. Fuel Processing Technology, 2022, 230: 107210.
112	Wang Y, Jiang P X, Zhu Y. A novel global reaction modeling approach considering the effects of pressure on pyrolysis of n-decane at supercritical pressures[J]. Fuel 2021, 287: 119416.
113	Guo W, Li B, Chi H, et al. On-line SFC-UV/Vis-MS using flow selection interfaces to monitor continuous flow single and sequential stage organic reactions in supercritical carbon dioxide[J]. The Journal of Supercritical Fluids, 2023, 199: 105957.
114	Guo W, Li B, Chi H, et al. Reactions of two primary aromatic amines in modified supercritical carbon dioxide to synthesize sulfonamides: on-line SFC to perform solubility measurements and method to monitor reaction progress[J]. The Journal of Supercritical Fluids, 2022, 179: 105419.
115	Kant R, Kumar A. Review on essential oil extraction from aromatic and medicinal plants: techniques, performance and economic analysis[J]. Sustainable Chemistry and Pharmacy, 2022, 30: 100829.
116	Chañi-Paucar L O, Johner J C F, Zabot G L, et al. Technical and economic evaluation of supercritical CO₂ extraction of oil from sucupira branca seeds[J]. The Journal of Supercritical Fluids, 2022, 181: 105494.
117	陈志荣,李浩然,尹红,等.一种α-异佛尔酮的制备方法:101633610 A[P]. 2010-01-27.
	Chen Z R, Li H R, Yin H, et al. A method for preparing α-isophorone: 101633610 A[P]. 2010-01-27.
118	李浩然,马啸,胡柏剡,等.一种丁酮醇的合成方法:118791371A[P].2024-10-18.
	Lin H R, Ma X, Hu B Y, et al. A synthesis method of butanone alcohol:118791371 A[P]. 2024-10-18.

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超临界反应及超临界流体参与的反应研究与应用进展

Progress in supercritical reactions and supercritical fluid participated reactions and their applications

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