Chemical Industry and Engineering Progress ›› 2023, Vol. 42 ›› Issue (7): 3489-3500.DOI: 10.16085/j.issn.1000-6613.2022-1590
• Energy processes and technology • Previous Articles Next Articles
HAN Hengwen(), HAN Wei(), LI Mingfeng
Received:
2022-08-29
Revised:
2022-11-05
Online:
2023-08-14
Published:
2023-07-15
Contact:
HAN Wei
通讯作者:
韩伟
作者简介:
韩恒文(1973—),男,硕士,高级工程师,主要从事石油加工和产品开发工作。E-mail:hanhw.ripp@sinopec.com。
CLC Number:
HAN Hengwen, HAN Wei, LI Mingfeng. Research progress in olefin hydration process and the catalysts[J]. Chemical Industry and Engineering Progress, 2023, 42(7): 3489-3500.
韩恒文, 韩伟, 李明丰. 烯烃水合反应工艺与催化剂研究进展[J]. 化工进展, 2023, 42(7): 3489-3500.
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烯烃水合方法 | 催化剂 | 反应机理 | 合成产物 | 优点/缺点 |
---|---|---|---|---|
强酸水解 | 硫酸 | 马氏规则亲电加成、直接路径 | 乙醇、异丙醇等,长链则为仲、叔醇 | 简单、廉价/腐蚀、易重排生成仲醇 |
过渡金属催化烯烃水合反应 | 过渡金属(钯)盐 | 反马氏规则、直接路径 | 苯乙醇 | 特定醇的合成/过程复杂、催化剂昂贵 |
酸酯化-水解 | 硫酸、三氯化铝、固体酸、合成树脂 | 马氏规则亲电加成、间接路径 | 异丙醇、环己醇等 | 过程较复杂、消耗蒸汽、腐蚀严重、副产物多 |
硼氢化-氧化水解 | 双氧水、碱 | 反马氏规则、间接路径(硼烷化、氧化水解) | 伯醇 | 原子利用率高,不宜重排/环境影响大 |
烯烃串联羟基化 | 乙腈、乙酸钾 | 自由基-极性反应 | 芳基醇 | 需加热、碱催化受限制 |
光催化烯烃水合 | 光,二苯二硫醚(Ph-S-S-Ph) | 反马氏规则、自由基(争议) | 伯醇、仲醇、叠氮醇 | 原料易得、方法简单/难控制、催化剂贵、需氢供体 |
酶催化烯烃水合 | 丙氨酸磷酸核糖醇连接酶 | 反马氏规则 | 芳香基取代醇 | 条件温和、转化率高,绿色无污染 |
烯烃水合方法 | 催化剂 | 反应机理 | 合成产物 | 优点/缺点 |
---|---|---|---|---|
强酸水解 | 硫酸 | 马氏规则亲电加成、直接路径 | 乙醇、异丙醇等,长链则为仲、叔醇 | 简单、廉价/腐蚀、易重排生成仲醇 |
过渡金属催化烯烃水合反应 | 过渡金属(钯)盐 | 反马氏规则、直接路径 | 苯乙醇 | 特定醇的合成/过程复杂、催化剂昂贵 |
酸酯化-水解 | 硫酸、三氯化铝、固体酸、合成树脂 | 马氏规则亲电加成、间接路径 | 异丙醇、环己醇等 | 过程较复杂、消耗蒸汽、腐蚀严重、副产物多 |
硼氢化-氧化水解 | 双氧水、碱 | 反马氏规则、间接路径(硼烷化、氧化水解) | 伯醇 | 原子利用率高,不宜重排/环境影响大 |
烯烃串联羟基化 | 乙腈、乙酸钾 | 自由基-极性反应 | 芳基醇 | 需加热、碱催化受限制 |
光催化烯烃水合 | 光,二苯二硫醚(Ph-S-S-Ph) | 反马氏规则、自由基(争议) | 伯醇、仲醇、叠氮醇 | 原料易得、方法简单/难控制、催化剂贵、需氢供体 |
酶催化烯烃水合 | 丙氨酸磷酸核糖醇连接酶 | 反马氏规则 | 芳香基取代醇 | 条件温和、转化率高,绿色无污染 |
工艺 | 公司 | 国家 | 年份 | 催化剂 |
---|---|---|---|---|
均相催化环己烯水合工艺 | 菲利普石油公司 | 美国 | 1974 | 硫酸、苯磺酸 |
非均相催化环己烯水合工艺 | 杜邦 | 美国 | 1980 | 全氟磺酸树脂 |
苯-环己烯-环己醇工艺 | 旭化成集团 | 日本 | 1990 | Ru/HZSM-5 |
引进旭化成工艺+改进工艺 | 神马集团 | 中国 | 1998 | Ru/HZSM-5 |
工艺 | 公司 | 国家 | 年份 | 催化剂 |
---|---|---|---|---|
均相催化环己烯水合工艺 | 菲利普石油公司 | 美国 | 1974 | 硫酸、苯磺酸 |
非均相催化环己烯水合工艺 | 杜邦 | 美国 | 1980 | 全氟磺酸树脂 |
苯-环己烯-环己醇工艺 | 旭化成集团 | 日本 | 1990 | Ru/HZSM-5 |
引进旭化成工艺+改进工艺 | 神马集团 | 中国 | 1998 | Ru/HZSM-5 |
项目 | 维巴工艺 | 德山曹达工艺 | 德士古工艺 |
---|---|---|---|
反应条件 | |||
反应物相态 | 气相 | 液相 | 气液混合相 |
催化剂种类 | 固体磷酸 | 钨、钼系杂多酸 | 阳离子交换树脂 |
反应压力/MPa | 2.0~2.5 | 20.5~25.0 | 6.0~8.0 |
反应温度/℃ | 180~260 | 240~280 | 130~160 |
丙烯纯度(φ)/% | ≥99 | 95 | 92 |
水/烯摩尔比 | 0.6~0.8 | 25.0~27.0 | 12.5~15.0 |
反应结果 | |||
丙烯单程转化率/% | 5~6 | 50~75 | 60~70 |
异丙醇选择性/% | 98~99 | 92~96 | 98~99 |
设备腐蚀程度 | 较严重 | 无 | 无 |
催化剂稳定性 | 磷酸流失 | 非常好 | 不耐高温 |
催化剂寿命 | >12个月 | 半永久性 | >8个月 |
项目 | 维巴工艺 | 德山曹达工艺 | 德士古工艺 |
---|---|---|---|
反应条件 | |||
反应物相态 | 气相 | 液相 | 气液混合相 |
催化剂种类 | 固体磷酸 | 钨、钼系杂多酸 | 阳离子交换树脂 |
反应压力/MPa | 2.0~2.5 | 20.5~25.0 | 6.0~8.0 |
反应温度/℃ | 180~260 | 240~280 | 130~160 |
丙烯纯度(φ)/% | ≥99 | 95 | 92 |
水/烯摩尔比 | 0.6~0.8 | 25.0~27.0 | 12.5~15.0 |
反应结果 | |||
丙烯单程转化率/% | 5~6 | 50~75 | 60~70 |
异丙醇选择性/% | 98~99 | 92~96 | 98~99 |
设备腐蚀程度 | 较严重 | 无 | 无 |
催化剂稳定性 | 磷酸流失 | 非常好 | 不耐高温 |
催化剂寿命 | >12个月 | 半永久性 | >8个月 |
催化剂类别 | 丙烯转化率/% | 异丙醇选择性/% |
---|---|---|
Y | 10 | 99 |
ZSM-5 | 12.8 | 100 |
Md | 10.6 | 99 |
MCM-41 | 5.6 | 100 |
β | 32.4 | 99.8 |
催化剂类别 | 丙烯转化率/% | 异丙醇选择性/% |
---|---|---|
Y | 10 | 99 |
ZSM-5 | 12.8 | 100 |
Md | 10.6 | 99 |
MCM-41 | 5.6 | 100 |
β | 32.4 | 99.8 |
1 | 李淑娟. 环己烯间接水合与直接水合法制备环己醇过程研究[D]. 湘潭: 湘潭大学, 2020. |
LI Shujuan. Study on the preparation of cyclohexanol by direct hydration and indirect hydration of cyclohexene[D]. Xiangtan: Xiangtan University, 2020. | |
2 | 孙梦垚. 丙烯水合制异丙醇催化剂的研究[D]. 大连: 大连理工大学, 2016. |
SUN Mengyao. Investigation on catalysts for hydration of propene to isopropanol[D]. Dalian: Dalian University of Technology, 2016. | |
3 | 乔凯, 吕连海, 翟庆铜, 等. 丙烯催化水合制异丙醇工艺研究[J]. 当代化工, 2006, 35(5): 303-306. |
QIAO Kai, Lianhai LYU, ZHAI Qingtong, et al. Study on catalytic hydration of propylene to isopropanol[J]. Contemporary Chemical Industry, 2006, 35(5): 303-306. | |
4 | DONG Guangbin, TEO P, WICKENS Z K, et al. Primary alcohols from terminal olefins: Formal anti-Markovnikov hydration via triple relay catalysis[J]. Science, 2011, 333(6049): 1609-1612. |
5 | SMITH M B. March's advanced organic chemistry: Reactions, mechanisms, and structure[M]. 7th ed. Wiley: New York, 2013. |
6 | KINDT S, WICHT K, HEINRICH M R. Thermally induced carbohydroxylation of styrenes with aryldiazonium salts[J]. Angewandte Chemie International Edition, 2016, 55(30): 8744-8747. |
7 | HU Xia, ZHANG Guoting, BU Faxiang, et al. Visible-light-mediated anti-Markovnikov hydration of olefins[J]. ACS Catalysis, 2017, 7(2): 1432-1437. |
8 | YANG Bo, LU Zhan. Visible-light-promoted metal-free aerobic hydroxyazidation of alkenes[J]. ACS Catalysis, 2017, 7(12): 8362-8365. |
9 | HAMMER S C, KUBIK G, WATKINS E, et al. Anti-Markovnikov alkene oxidation by metal-oxo-mediated enzyme catalysis[J]. Science, 2017, 358(6360): 215-218. |
10 | DEMMING R M, HAMMER S C, NESTL B M, et al. Asymmetric enzymatic hydration of unactivated, aliphatic alkenes[J]. Angewandte Chemie International Edition, 2019, 58(1): 173-177. |
11 | 林晖, 陈红歌, 唐燕红, 等. 一种烯烃水合酶在制备伯醇中的应用:CN201911214183.6[P]. 2020-02-21. |
LIN Hui, CHEN Hongge, TANG Yanhong, et al. Application of olefin hydratase in preparation of primary alcohol: CN201911214183.6 [P]. 2020-02-21. | |
12 | 王殿中, 舒兴田, 何鸣元. 环己烯水合制备环己醇的研究Ⅰ. 分子筛结构及晶粒大小的影响[J]. 催化学报, 2002, 23(6): 503-506. |
WANG Dianzhong, SHU Xingtian, HE Mingyuan. Studies on production of cyclohexanol by hydration of cyclohexeneⅠ. Effects of zeolite structure and crystal size[J]. Chinese Journal of Catalysis, 2002, 23(6): 503-506. | |
13 | 姚旭婷. 失活钛硅分子筛催化环己烯水合反应的研究[D]. 上海: 华东师范大学, 2018. |
YAO Xuting. Deactivated titanosilicate zeolite as an efficient catalyst for liquid-phase hydration of cyclohexene[D]. Shanghai: East China Normal University, 2018. | |
14 | YAO Xuting, HUANG Xin, LIN Yuxia, et al. Deactivated TS-1 as efficient catalyst for hydration of cyclohexene to cyclohexanol[J]. Acta Chimica Sinica, 2020, 78(10): 1111-1119. |
15 | SUN Wenchang, ZHANG Xu, HOU Yueming, et al. Polystyrene-based hierarchically macro-mesoporous solid acid: A robust and highly efficient catalyst for indirect hydration of cyclohexene to cyclohexanol by a one-pot method under mild conditions[J]. Industrial & Engineering Chemistry Research, 2020, 59(14): 6435-6444. |
16 | 吴克. 改性分子筛固载磷钨钼杂多酸催化剂的制备及性能研究[D]. 通辽: 内蒙古民族大学, 2020. |
WU Ke. Study on preparation and performance of H3PW12- n Mo n O34 heteropoly acid supported on modified zeolite[D]. Tongliao: Inner Mongolia University for the Nationalities, 2020. | |
17 | 刘昭宇, 朱浩天, 卢明达, 等. 有机阳离子修饰的Strandberg型钼磷酸盐的合成、催化性能[J]. 应用化学, 2015, 32(2): 214-220. |
LIU Zhaoyu, ZHU Haotian, LU Mingda, et al. Synthesis and catalytic activity of a strandberg-type molybdophosphate modified by organic cations[J]. Chinese Journal of Applied Chemistry, 2015, 32(2): 214-220. | |
18 | SALVADOR V T, SILVA E S, GONÇALVES P G C, et al. Biomass transformation: Hydration and isomerization reactions of turpentine oil using ion exchange resins as catalyst[J]. Sustainable Chemistry and Pharmacy, 2020, 15: 100214. |
19 | BIANCHINI E, PIETROBON L, RONCHIN L, et al. Trifluoroacetic acid promoted hydration of styrene catalyzed by sulfonic resins: Comparison of the reactivity of styrene, n-hexene and cyclohexene[J]. Applied Catalysis A: General, 2019, 570: 130-138. |
20 | 霍稳周, 魏晓霞, 田丹, 等. 一种低碳烯烃水合工艺: CN104591961A[P]. 2015-05-06. |
HUO Wenzhou, WEI Xiaoxia, TIAN Dan, et al. A low carbon olefin hydration process: CN104591961A[P]. 2015-05-06. | |
21 | 周峰, 马会霞,姜睿,等. 一种烯烃水合反应方法: CN114507116A[P]. 2022-05-17. |
ZHOU Feng, MA Huixia, JIANG Rui, et al. A method of olefin hydration reaction: CN114507116A[P]. 2022-05-17. | |
22 | 袁清,毛俊义,黄涛,等. 一种烯烃水合反应方法和系统: CN112723989A[P]. 2021-04-30. |
YUAN Qing, MAO Junyi, HUANG Tao, et al. An olefin hydration reaction method and system: CN112723989A[P]. 2021-04-30. | |
23 | 李星. 异丙醇的生产技术及市场分析[J]. 山东化工, 2021, 50(11): 79-81. |
LI Xing. Production technology and market analysis of isopropanol[J]. Shandong Chemical Industry, 2021, 50(11): 79-81. | |
24 | 单祥雷. 环己烯水合制备环己醇催化反应过程的研究[D]. 上海: 华东理工大学, 2011. |
SHAN Xianglei. Study on catalytic reaction process for synthesis of cyclohexanol from hydration of cyclohexene[D]. Shanghai: East China University of Science and Technology, 2011. | |
25 | LI Jing, YANG Lihong, LI Fang, et al. Hydration of cyclohexene to cyclohexanol over SO3H-functionalized imidazole ionic liquids[J]. Reaction Kinetics, Mechanisms and Catalysis, 2015, 114(1): 173-183. |
26 | 房承宣, 于泳, 王亚涛, 等. 环己烯水合催化剂及工艺研究进展[J]. 现代化工, 2012, 32(12): 16-19. |
FANG Chengxuan, YU Yong, WANG Yatao, et al. Research progress of catalyst and process in cyclohexene hydration[J]. Modern Chemical Industry, 2012, 32(12): 16-19. | |
27 | 李一鸣. 环己烯直接水合相关基础研究及工艺开发[D]. 福州:福州大学,2020. |
LI Yiming. Basic research and process development of cyclohexene direct hydration[D]. Fuzhou: Fuzhou University,2020. | |
28 | 谢小雨. 生物质碳基固体酸催化剂上环己烯水合制备环己醇工艺研究[D]. 杭州:浙江大学,2021. |
XIE Xiaoyu. Preparation of cyclohexanol by hydration of cyclohexene on biomass-carbon based solid catalysts[D]. Hangzhou: Zhejiang University, 2021. | |
29 | 朱林. (类)离子液体在催化环己烯水合反应中的应用[D]. 天津: 河北工业大学, 2020. |
ZHU Lin. Application of (pesudo) ionic liquid in catalyzing hydration of cycloexene[D]. Tianjin: Hebei University of Technology, 2020. | |
30 | FUKUHARA H, MATSUNAGA F, KOBAYASHI M. Preparation of cycloalkanols by catalytic hydration of cycloalkenes: JP1990040334A[P]. 1990-02-09. |
31 | 林清香. 环己烯催化水合制备环己醇研究[D]. 杭州: 浙江大学, 2008. |
LIN Qingxiang. Study on the preparation of cyclohexanol by catalysis hydration of cyclohexene[D]. Hangzhou: Zhejiang University, 2008. | |
32 | 申武, 林清香, 朱明乔. 环己烯水合制环己醇研究进展[J]. 合成纤维工业, 2009, 32(2): 45-47. |
SHEN Wu, LIN Qingxiang, ZHU Mingqiao. Research progress in cyclohexene hydration to cyclohexanol[J]. China Synthetic Fiber Industry, 2009, 32(2): 45-47. | |
33 | U·穆勒尔, T·希尔, J·恒克勒曼, 等. 由烯烃生产醇的方法: CN1399621[P]. 2003-02-26. |
ULRICH M, THOMAS H, JOCHEM H, et al. Method for producing an alcohol from an alkene: CN1399621[P]. 2003-02-26. | |
34 | 刘小熙. ZSM-5催化剂作用下环己烯水合制环己醇反应过程实验研究[D]. 石家庄: 河北科技大学, 2019. |
LIU Xiaoxi. Experimental study on hydration process of cyclohexene to cyclohexanol with ZSM-5 catalysts[D]. Shijiazhuang: Hebei University of Science and Technology, 2019. | |
35 | TIAN Hui, LIU Shuai, HAN Yaochi, et al. Acid treatment to adjust zeolite hydrophobicity for olefin hydration reaction[J]. Journal of Porous Materials, 2022, 29(3): 713-722. |
36 | 王明明, 姚志龙, 赵如松. 磷改性HZSM-5分子筛催化环己烯水合反应活性[J]. 工业催化, 2011, 19(2): 40-45. |
WANG Mingming, YAO Zhilong, ZHAO Rusong. Catalytic activity of phosphorus-modified-HZSM-5 zeolites on cyclohexene hydration[J]. Industrial Catalysis, 2011, 19(2): 40-45. | |
37 | JIN Yuzhen, ZONG Lukuan, WANG Xiangyu, et al. Catalytic enhancement of cyclohexene hydration by Ga-Doped ZSM-5 zeolites[J]. ACS Omega, 2022, 7(30):26289-26297. |
38 | MENG Fanjun, WANG Yaquan, WANG Shougui, et al. Hydration of cyclohexene over zeolite ZSM-5: Improved catalyst performance by alkali treatment[J]. Reaction Kinetics, Mechanisms and Catalysis, 2016, 119(2): 671-683. |
39 | 刘帅. HZSM-5分子筛改性及其催化环己烯水合反应过程研究[D]. 烟台:烟台大学, 2022. |
LIU Shuai. Study on HZSM-5 modification and catalytic cyclohexene of hydration process[D]. Yantai: Yantai University, 2022. | |
40 | LIU Shuai, SUN Dahai, TIAN Hui. Novel hydrophobic catalysts to promote hydration at the water-oil interface[J]. RSC Advances, 2021, 11(30): 18299-18307. |
41 | 宋守强, 李明罡, 李黎声, 等. 磷改性ZSM-5分子筛的水热稳定性[J]. 石油学报(石油加工), 2014, 30(2): 194-203. |
SONG Shouqiang, LI Minggang, LI Lisheng, et al. Hydrothermal stability of P-modified ZSM-5 molecular sieves[J]. Acta Petrolei Sinica (Petroleum Processing Section), 2014, 30(2): 194-203. | |
42 | SHAN Xianglei, CHENG Zhenmin, LI Ying. Solvent effects on hydration of cyclohexene over H-ZSM-5 catalyst[J]. Journal of Chemical & Engineering Data, 2011, 56(12): 4310-4316. |
43 | 刘媛. 苯选择加氢和环己烯水合催化反应过程研究[D]. 天津: 河北工业大学, 2007. |
LIU Yuan. Study on the selective hydrogenation of benzene and hydration of cyclohexene[D]. Tianjin: Hebei University of Technology, 2007. | |
44 | TAKAMATSU Y, KANESHIMA T. Process for the preparation of cyclohexanol: US6552235[P]. 2003-04-22. |
45 | 励娟, 魏珺芳, 王延吉, 等. 异佛尔酮对环己烯水合反应性能的影响[J]. 精细石油化工, 2011, 28(4): 55-59. |
LI Juan, WEI Junfang, WANG Yanji, et al. Effect of isophorone on hydration of cyclohexene[J]. Speciality Petrochemicals, 2011, 28(4): 55-59. | |
46 | PANNEMAN H J, BEENACKERS A A C M. Solvent effects on the hydration of cyclohexene catalyzed by a strong acid ion-exchange resin. 1. Solubility of cyclohexene in aqueous sulfolane mixtures[J]. Industrial & Engineering Chemistry Research, 1992, 31(4): 1227-1231. |
47 | Jan PANNEMAN H, BEENACKERS A A C M. Solvent effects in the liquid phase hydration of cyclohexene catalyzed by a macroporous strong acid ion-exchange resin[J]. Chemical Engineering Science, 1992, 47(9/10/11): 2635-2640. |
48 | JIA Bin, YANG Xiu, HUANG Meiyu, et al. Hydration of alkenes catalyzed by wool-palladium-iron complex[J]. Reactive & Functional Polymers, 2003, 57(2/3): 163-168. |
49 | YUAN Peiqing, LIU Ying, BAI Fan, et al. Hydration of cyclohexene in sub-critical water over WO x -ZrO2 catalysts[J]. Catalysis Communications, 2011, 12(8): 753-756. |
50 | KUMAR R, KATARIYA A, FREUND H, et al. Development of a novel catalytic distillation process for cyclohexanol production: Mini plant experiments and complementary process simulations[J]. Organic Process Research & Development, 2011, 15(3): 527-539. |
51 | 赵贺潘. 碳基固体酸催化环己烯与甲酸酯化反应及动力学研究[D]. 天津: 河北工业大学, 2016. |
ZHAO Hepan. Study on the esterification of cyclohexene with formic acid over carbon-based solid acid and its kinetics[D]. Tianjin:Hebei University of Technology, 2016. | |
52 | 马恒. 异丙醇生产工艺研究进展[J]. 云南化工, 2021, 48(7): 18-20. |
MA Heng. Research progress of isopropanol production technology[J]. Yunnan Chemical Technology, 2021, 48(7): 18-20. | |
53 | 胡翔, 李涛. 以丙烯为原料的产业链延伸加工及其新进展[J]. 石油化工技术与经济, 2013, 29(2): 17-20. |
HU Xiang, LI Tao. Industrial chain extension processing with propylene as raw material and its progress[J]. Technology & Economics in Petrochemicals, 2013, 29(2): 17-20. | |
54 | 史可心, 陶涛, 李龙燕, 等. 异丙醇生产工艺的分析比较[J]. 当代化工研究, 2022(8): 155-158. |
SHI Kexin, TAO Tao, LI Longyan, et al. Analysis and comparison of production technology for isopropanol[J]. Modern Chemical Research, 2022(8): 155-158. | |
55 | 李雪玲. 酸改性SPU-WL、ZSM-5分子筛对异丙醇的催化研究[D]. 上海: 上海第二工业大学, 2022. |
LI Xueling. Catalysis of isopropanol by acid-modified SPU-WL and ZSM-5 molecular sieves[D]. Shanghai:Shanghai Polytechnic University,2022. | |
56 | 唐国旗, 徐利红, 田保亮, 等. 异丙醇的生产工艺及应用[J]. 石油化工, 2021, 50(3): 285-288. |
TANG Guoqi, XU Lihong, TIAN Baoliang, et al. Manufacturing technology and its application prospect of isopropanol[J]. Petrochemical Technology, 2021, 50(3): 285-288. | |
57 | 刘中民, 朱书魁, 张世刚, 等. 丙烯直接水合法生产异丙醇技术[J]. 精细与专用化学品, 2005, 13(15): 1-4. |
LIU Zhongmin, ZHU Shukui, ZHANG Shigang, et al. Progress on production of isopropanol by direct hydration of propylene[J]. Fine and Specialty Chemicals, 2005, 13(15): 1-4. | |
58 | 郭琳. 高低温费托合成联产中烯烃齐聚催化剂的制备及性能研究[D]. 太原: 太原理工大学, 2013. |
GUO Lin. Olefin oligomerization catalyst preparation and performance in coproduction of high/low temperature Fischer-Tropsch synthesis[D]. Taiyuan: Taiyuan University of Technology, 2013. | |
59 | 袁梅卿, 姚亚平, 徐菁, 等. 新一代固体磷酸催化剂T-99研制[J]. 化学世界, 2002, 43(5): 239-242. |
YUAN Meiqing, YAO Yaping, XU Jing, et al. Study on new solid phosphoric acid catalyst T-99[J]. Chemical World, 2002, 43(5): 239-242. | |
60 | 王慧风, 刘靖, 喻瑞. ZSM-35分子筛的酸改性及其用于丙烯水合制异丙醇反应的性能[J]. 工业催化, 2018, 26(7): 48-53. |
WANG Huifeng, LIU Jing, YU Rui. Catalytic performance of acid modified ZSM-35 zeolite for propylene hydration to isopropanol[J]. Industrial Catalysis, 2018, 26(7): 48-53. | |
61 | 周庆伟. 丙烯直接水合制备异丙醇工艺的研究[D]. 大连: 大连理工大学, 2015. |
ZHOU Qingwei. Study on the process of direct hydration of propylene for preparation of isopropanol[D]. Dalian: Dalian University of Technology, 2015. | |
62 | POPOVA N M, DOSUMOV K. Hydration of olefins into alcohols[J]. Eurasian Chemico-Technological Journal, 2009, 12(1): 23. |
63 | BOURANE A, VOGEL S R, XU Wei. Hydrated niobium oxide nanoparticle containing catalysts for olefin hydration: US8629080[P]. 2014-01-14. |
64 | 王延吉, 唐靖, 李赫. 丙烯水合制备异丙醇/异丙醚沸石催化剂[J]. 石油化工,1995, 24(7): 507-511. |
WANG Yanji, TANG Jing, LI He. Preparation of isopropanol/isopropyl ether zeolite catalyst by hydration of propylene[J]. Petrochemical Technology, 1995, 24(7): 507-511. | |
65 | 李伟, 陶克毅, 李赫垣. 分子筛催化丙烯水合制异丙醇的研究进展[J]. 石油化工, 1996, 25(9): 656-662. |
LI Wei, TAO Keyi, LI Heyuan. Research progress in preparation of isopropanol from propylene hydration catalyzed by molecular sieves[J]. Petrochemical Technology, 1996, 25(9): 656-662. | |
66 | BELL W K, BROWN S H, TREWELLA J C. Multistage indirect propylene hydration process for the production of diisopropyl ether and isopropanol: US5569789[P]. 1996-10-29. |
67 | CAO Zhijun, ZHAO Xin, HE Feiqiang, et al. Highly efficient indirect hydration of olefins to alcohols using superacidic polyoxometalate-based ionic hybrids catalysts[J]. Industrial & Engineering Chemistry Research, 2018, 57(19): 6654-6663. |
68 | 谢小雨, 李竑樾, 朱明乔. C6~C8烯烃水合催化剂的研究进展[J]. 合成纤维工业, 2021, 44(1): 43-47. |
XIE Xiaoyu, LI Hongyue, ZHU Mingqiao. Research progress of C6—C8 olefin hydration catalysts[J]. China Synthetic Fiber Industry, 2021, 44(1): 43-47. | |
69 | KOSEOGLU O R, SAWAN A. Conversion of olefinic naphthas by hydration to produce middle distillate fuel blending components: WO2020146181A8 [S]. 2021-07-29. |
70 | XUE Lei, ZHOU Dejun, TANG Li, et al. The asymmetric hydration of 1-octene to (S)-(+)-2-octanol with a biopolymer-metal complex, silica-supported chitosan-cobalt complex[J]. Reactive & Functional Polymers, 2004, 58(2) : 117-121. |
71 | PRASETYOKO D, RAMLI Z, ENDUD S, et al. TS-1 loaded with sulfated zirconia as bifunctional oxidative and acidic catalyst for transformation of 1-octene to 1,2-octanediol[J]. Journal of Molecular Catalysis A: Chemical, 2005, 241(1/2): 118-125. |
72 | 黄乐. 合成气制高碳醇CuFe催化剂研究[D]. 上海: 华东理工大学, 2021. |
HUANG Le. Study on CuFe catalysts for higher alcohols synthesis from syngas[D]. Shanghai: East China University of Science and Technology, 2021. | |
73 | 钱菊敏. 合成气制多碳醇技术进展[J]. 化学反应工程与工艺, 2018, 34(2): 178-187. |
QIAN Jumin. Recent advances in higher alcohols synthesis from syngas[J]. Chemical Reaction Engineering and Technology, 2018, 34(2): 178-187. | |
74 | HARALD K, THOMAS U, DETLEF H, et al. Process for the production of lower alcohols by olefin hydration: US8809600[P]. 2014-08-19. |
75 | XU Wei. Dual phase catalysts system for mixed olefin hydrations: US8865951(B2)[P]. 2014-10-21. |
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