Page 214 - 《精细化工》2022年第7期
P. 214

·1500·                            精细化工   FINE CHEMICALS                                 第 39 卷

                                                                   green oxidation system of catalytic oxidation synthesis of phenylacetone
                                                                   by ethylene benzene[J]. Gansu Science and Technology (甘肃科技),
                                                                   2011, 27(22): 51-54.
                                                               [4]   LI J Q (李家其), GUO J (郭军),YIN D L (尹笃林). Progress on
                                                                   ethylbenzene catalytic oxidation to synthesize acetophenone[J]. Fine
                                                                   Chemical Intermediates (精细化工中间体), 2005, 35(4): 1-3.
                                                               [5]   LI G X (李贵贤), LI  Y Z (李亚珍),  XU Y D  (徐彦铎), et al.
                                                                   Advances in development of catalysts for liquid-phase oxidation of
                                                                   ethylbenzene to acetophenone[J]. Applied Chemical Industry (应用
                                                                   化工), 2012, 41(8): 1412-1416.
                                                               [6]   XU  Y, HU  X B,  SHAO J,  et al. Hydration  of alkynes at room
                                                                   temperature catalyzed by gold (Ⅰ) isocyanide compounds[J]. Green
                                                                   Chemistry, 2015, 17(1): 532-537.
                                                               [7]   LIU W L (刘文杰), LI J H (李金恒). Cerium(Ⅳ) sulfate-catalyzed
                                                                   hydration[J]. Chinese Journal of Organic Chemistry (有机化学), 2006,
                                                                   26(8): 1073-1078.
                                                               [8]   HINTERMANN  L, LABONNE  A. Catalytic hydration  of alkynes
                                                                   and its application in synthesis[J]. Synthesis, 2007, (8): 1121-1150.
                             图 6   反应机理                        [9]   BUDDE W L, DESSY R E. The homogeneously catalyzed hydration
                        Fig. 6  Reaction mechanism                 of acetylenes by mercuric perchlorate-perchloric acid: Evidence for a
                                                                   bis-(acetylene)-mercuric ion complex as an intermediate[J]. Journal
                 由图 6 可见,炔烃首先扩散到 HBeta 的外表面,                       of the American Chemical Society, 1963, 85(24): 3964-3970.
                                                               [10]  GOODWIN J A, APONICK A. Regioselectivity in the Au-catalyzed
            随后吸附到布朗斯特酸性位点(BAS,弱酸和中强                                hydration and hydroalkoxylation of alkynes[J]. Chemical Communications,
            酸位点)上,形成 ArC≡≡C-BAS 加合物Ⅰ(1)。                           2015, 51(42): 8730-8741.
                                                               [11]  XU C X, DU W Y, ZENG Y,  et al. Reactivity switch enabled by
            水分子和被 BAS 活化后的三键通过加成反应生成
                                                                   counterion: Highly chemoselective dimerization and  hydration  of
            不稳定的烯醇中间体Ⅱ(2)。随后,烯醇在 BAS                               terminal alkynes [J]. Organic Letters, 2014, 16(3): 948-951.
            上经过两个平行的单电子转移过程,形成稳定的水                             [12]  HIRONOBU K, KEIJI U, SHUNICHI F, et al. Isolation and crystal
                                                                   structures of both enol and keto tautomer intermediates in a hydration
            合产物芳香酮Ⅲ(3)。最后,芳香酮从催化剂的                                 of an alkyne-carboxylic acid ester catalyzed by iridium complexes in
            BAS 脱附,形成最终产物芳香酮,同时催化剂得到                               water[J]. Journal of American Chemical Society, 2008, 130(50):
            循环使用(4)。                                               17141-17147.
                                                               [13]  FRANCESCO T, ANDREW M C, ALESSANDRO S, et al. Platinum
                                                                   (Ⅱ) diphosphinamine complexes for the efficient hydration of alkynes
            3   结论                                                 in micellar media[J]. Advanced Synthesis and Catalysis, 2012, 354(16):
                                                                   1095-1104.
                 本文以廉价易得的酸性沸石 HBeta 为催化剂,                      [14]  JIN X J, OISHI T, YAMAGUCHI K, et al. Heterogeneously catalyzed
                                                                   efficient hydration of alkynes to ketones by tin-tungsten mixed oxides[J].
            在温和的条件下,实现了多种芳基酮的绿色合成。
                                                                   Chemistry A European Journal, 2011, 17(4): 1261-1267.
            该体系避免了有机配体、高毒性催化剂和贵金属盐                             [15]  ÖTVÖS S  B, SZÉCSÉNYI  Z, FÜLӦP F, et  al. Bismuth(Ⅲ)-
            催化剂的使用,因此,该催化体系更加清洁,产物                                 catalyzed hydration of terminal alkynes: Sustainable synthesis  of
                                                                   methyl ketones in  batch and flow[J]. American Chemical Society
            提纯更加简便,大大降低了该工艺的能源消耗。同                                 Sustainable Chemistry and Engineering, 2019, 7(15): 13286-13293.
            时 HBeta 催化剂在催化芳基炔烃水合体系中循环使                         [16]  PARK J, YEON J, LEE P H, et al. Iron-catalyzed indirect hydration
                                                                   of alkynes in presence of methanesulfonic acid[J]. Tetrahedron Letters,
            用 4 次依然有较好的活性(第 5 次使用后产率仍可
                                                                   2013, 54(33): 4414-4417.
            达 99%),表现出了优异的可重复使用性能。经过                           [17]  HASSAM M, LI W S. Copper-catalyzed markovnikov hydration of
            对反应条件的优化和底物适用范围的考察发现:该                                 alkynes[J]. Tetrahedron, 2015, 71(18): 2719-2723.
                                                               [18]  GAO L F, ZHUGE W Y, FENG X, et al. Co/rGO synthesized via the
            催化体系在相对温和的条件下(120  ℃,6 h)对大                            Alcohol-thermal method as a  heterogeneous catalyst for  the highly
            量的芳基炔烃表现出了良好的兼容性,产物的产率                                 efficient oxidation of ethylbenzene with oxygen[J]. New Journal of
            均高于 90%。                                               Chemistry, 2019, 43(21): 8189-8194.
                                                               [19]  YU X Y (于心玉), GAO S (高珊),  LIU C H  (刘彩华), et al.
                                                                   Preparation of 2-t-butyl-p-cresol catalyzed by Hβ zeolite[J].  Fine
            参考文献:
                                                                   Chemicals (精细化工), 2006, 23(6): 598-600.
            [1]   YANG X (杨晰), LONG H T (龙海涛). Research progress  on   [20]  TAO T Y (陶庭雨), FU W Q (傅雯倩). Preparation of a Ni 2P/HZSM-5
                 catalytic oxidation of ethylbenzene to acetophenone by  oxygen[J].   catalyst  and its catalytic performance  for phenylacetylene selective
                 Industrial Catalysts (工业催化), 2021, 29(8): 19-25.   hydrogenation[J]. Fine Chemicals (精细化工), 2019, 34(5): 929-934.
            [2]   SUN Y (孙宇), SHI W W (石薇薇), SHEN J (沈健). Synthesis of   [21]  MU M M (穆曼曼), CHEN L G (陈立功). Progress of Friedel-Crafts
                 acetophenone by catalytic oxidation of ethylbenzene over V-SBA-15[J].   acylation of arenes over solid acid catalysts[J]. Fine Chemicals (精细
                 Gas Chemical Industry (天然气化工), 2016, 41(6): 44-48.   化工), 2017, 34(4): 361-367.
            [3]   MA J J (马建军), LI L (李莉), MAO Z H (毛志红), et al. Progress in                 (下转第 1512 页)
   209   210   211   212   213   214   215   216   217   218   219