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Synthesis of propylene glycol methyl ether over amine modifiedporous silica by ultrasonic techniqueXuehong Zhang a,b, Wenyu Zhang a,b, Junping Li a, Ning Zhao a, Wei Wei a, Yuhan Sun a,*a State Key Laboratory of Coal Conversion, Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan 030001, Chinab Graduate School of the Chinese Academy of Sciences, Beijing 100039, ChinaReceived 16 May 2006; received in revised form 10 July 2006; accepted 12 July 2006Available online 21 July 2006AbstractAmine modified porous silica were synthesized by ultrasonic technique under mild The samples, which were characterizedby BET, 29Si NMR spectra, element analysis and indicator dye adsorption, exhibited promising catalytic properties towards the synthesisof propylene glycol methyl ether from methanol and propylene They had both high yields and reusability in the reaction, indicatingthat ultrasonic technique was effective for the preparation of organically modified silica Furthermore, the possible reactionmechanism was proposed for the synthesis of propylene glycol methyl ether over such type of 2006 Elsevier BV All rights Keywords: Modified porous silica; Ultrasonic technique; Propylene oxide; Methanol; Propylene glycol methyl IntroductionThe attempt to heterogenize homogeneous catalyst asalternatives to more traditional reagents and catalysts hasbeen one area of research that has seen increasing Much recent work was focused on the preparation oforganically modified solid bases to heterogenize homogeneousamine The modification process was generallyoperated by stirring, heating, refluxing, [1–3]Recently, the interest in synthetic sonochemistry reactionshas grown [4] The ultrasonic technique has been widelyapplied in two-phase systems due to its advantages, suchas high accuracy and Most of these reactions haveinvolved a heterogeneous chemical interaction [5] In thearea of porous materials functionalized by organic groups,however, only limited applications of ultrasound have beenexplored [6,7] In the present work, an alternative syntheticroute for the formation of amine modified silica was developedby using ultrasonic energy, which can produce chemicalmodifications on solids by cavitation phenomenon [8]The amines modified silica with ‘‘single site’’ base strengthwere promising catalysts for a variety of reactions [9]The synthesis of glycol ether over base catalysts is animportant kind of reaction in organic There areseveral methods for the synthesis of propylene glycol ether[10,11] Among them the propylene oxide method is mostlyconvenient and industrial Generally, propyleneoxide reacts with fatty alcohol via acid or base The catalysts used in this process include earlier homogenousbase or acid (NaOH, alcoholic sodium and BF3), latersolid acid and However, few studies have reported theuse of amine modified silica as catalysts for the synthesis ofpropylene glycol methyl ether, though inorganic solid basiccatalysts have performed good activity in the Theimmobilization of the amino functions on a mesoporoussupport, which were with ‘‘single site’’ base strength, couldafford an achieving this kind of In the present work, amine functionalized silica catalysts,including NH2/SiO2, NH(CH2)2NH2/SiO2, TAPM/SiO2 (2,4,6-triaminopyrimidine/SiO2) and TBD/SiO2(1,5,7-triazabicyclo[4,4,0]dec-5-ene/SiO2), were preparedwith 3-aminopropyltrimethoxysilane (APTMS), N-[3-(tri-methoxysilyl)propyl]ethylenediamine (EDPTMS) and 3-chloropropyltrimethoxysilane (CPTMS) as the couplingagents by ultrasonic technique under mild At the same time, in order to confirm the meritsof ultrasonic technique, NH2/SiO2 was also prepared bythe conventional method in order to understand the effectivebehaviour of ultrasonic technique in the preparationof functionalized porous In addition, the catalyticactivity of the organic solid base catalysts was evaluatedby the synthesis of propylene glycol methyl ether frommethanol and propylene Furthermore, the possiblereaction mechanism was proposed for the synthesis of propyleneglycol methyl ether over such type of E Synthesis of catalytic materialsThe amine functionalized silica catalysts could beachieved in two ways under similar conditions as reportedearlier [7]Aminopropylsilyl-functionalized SiO2 was prepared asfollows: 0 g SiO2 was preheated for 12 h at 473 K invacuum to remove all adsorbed moisture but surfaceOH-groups, and than cooled down to room temperaturein vacuum and transferred into a 250 mL conical After mixed with 0 mL cyclohexane and 0 mLAPTMS, the mixture in conical flask was put into the ultrasonicbath for 2 h (Sheshin, Japan, operating power 60 W)at ambient The catalyst was then obtained byextracting with toluene in a soxhlet extractor over a periodof 24 h and drying at 333 K in The same methodwas used for the preparation of NH(CH2)2NH2/SiOTBD/SiO2 was prepared by two steps: silica was firstlymodified by 3-chloropropyltrimethoxysilane via the samemethod as that of aminopropylsilyl-functionalized SiO2,and chloropropylsilyl-functionalized SiO2 was then reactedwith TBD (0 g) in cyclohexane (0 mL) The resultantwas treated by ultrasonic vibration for 1 Afterwards,the catalyst was obtained by extracting with toluene in aSoxhlet extractor over a period of 24 h and drying at333 K in The same method was used for the preparationof TAPM/SiO CharacterizationThe content of carbon, nitrogen, and hydrogen in all thesamples was determined using a Vario EL Thespecific surface area, total pore volume and average porediameter were measured by N2 adsorption–desorptionmethod on a Micromeritics ASAP-2000 instrument (Norcross,GA) The surface areas were calculated by BETmethod, and the pore size distribution was obtained byapplying the BJH pore analysis to the nitrogen adsorption–desorption 29Si NMR spectra were recordedon a Bruker MSL-400 The base strength ofsamples was detected by hammett Catalytic testThe catalytic properties were measured in a 75 ml batchreactor with mol ratio of methanol and propylene oxidebeing 5: After running at 403 K for 10 h under magneticstirring, the reactor was cooled down to room The product was then filtered and analyzed by a gas chromatographwith a flame ionization detector after centrifugalseparation from the The catalysts werewashed with solvent and used for recycling Results and Modification of porous silica with amine groupsThe content of carbon, nitrogen, and hydrogen inamine-free porous silica and all the modified samples werecarried out by elemental W and N% wereobtained from N%, C% and H% (see Table 1) The resultsshowed that there were no carbon and nitrogen in theamine-free porous As a result, carbon and nitrogenin modified samples ought to be from the The element analysis showed that N% of the graftedorganic groups achieved by conventional methods knownfrom the literature [12] was 13 mmol/g, which was farlower than that of the sample prepared by ultrasonic technique(00 mmol/g) (see Table 1) This should be due tothe application of ultrasonic energy to solids and liquids,which could provide the changes including cavitation(bubble formation in a liquid) and chemical reaction (accelerationof chemical reaction), [13] As a result, processesincluding particle size modification, cleaning ofsurfaces or the formation of fresh ones [14,15] could beobtained in heterogeneous media at a solid liquid As to the organic modification of porous silica, cavitationphenomena brought by ultrasound could speed up theliquid transferring velocity in the hole of porous materialsand the liquid–solid As a result, the liquidorganosilanes could be well contacted with silanol groupson the inner wall of the porous silica to react with themin a short time, while stiring could not reach such Therefore, the modification process finished simply andspeedily by The 29Si NMR spectra in solid state indicated that thecovalent bond formed between silylant agents and silanolgroups on the silica surface (see F 1) Two resonancesat 109 and 99 ppm could be attributed to 29Si nucleihaving four Si–O–Si linkages (Q4) and 29Si nuclei havingthree Si–O–Si linkages and one OH (Q3) [16], The resonances at 58 and 67 ppm were assignedto RSi(OSi)(OH)2 and RSi(OSi)3, respectively [17], whichillustrated the successful organo functionalization of poroussilica by the organic groups via covalent C/Nvalue (molar ratio) could also reflect the degree of graftingreaction between silanol groups and organosilanes [18]NH2/SiO2, NH(CH2)2NH2/SiO2 and TBD/SiO2 showedthe C/N = 3–5, 5–0 and 3–6, Theresults also suggested the anchorage of amine groups bySi–O–Si This agreed with the result of the 29SiNMR Structure and basicity of samplesF 2 displays N2 adsorption isotherms for the The functionalized samples displayed type IV isothermswith clear hysteresis loops associated with This indicated that the materials remainedmesoporous before and after functionalization and themodification by various organosilanes hardly changed theisotherm The BET surface area and pore volumeshowed a gradual reduction as the N% of graftedorganic groups increased (see Table 2) This could beattributed to the presence of functional A part ofamino groups grafted onto the microporous also led to adecrease in the BET surface The effect of the organicgroups on the pore diameter of the samples was slight forthe samples NH2/SiO2 and NH(CH2)2NH2/SiO But asfor the sample TBD/SiO2 and TAPM/ SiO2, perhaps dueto the big framework of (CH2)3/TAPM and (CH2)3/TBD groups, the average pore diameters of the samplesdecreased to 90 and 82 However, the average porediameter was not decreased seriously due to the low N%values of the The base strength H of a solid surface is defined as theability of the surface to convert an adsorbed electricallyneutral acid into its conjugate When an electricallyneutral acid indicator is adsorbed on a solid base from anonpolar solution, the color of the acid indicator is changedto that of its conjugate base, provided that the solidhas the necessary base strength to impart electron pairsto the acid [19] A solid with a large positive HH hasstrong basic Grafting with different functional groupscould result in different base As shown in Table3, TBD/SiO2 had the highest base strength of H 0,while NH2/SiO2 and NH(CH2)2NH2/SiO2 only had thebasicity of H 3 and 3 < H < 0, Compared to the other modified samples, TAPM/SiO2had weakest basicity of H < Thus, the basic strengthof the samples was in the order of TBD/SiO2 > NH(CH2)2NH2/SiO2 > NH2/SiO2 > TAPM/SiO Catalytic performanceThe catalytic activity was tested in the synthesis of propyleneglycol methyl ether from methanol and propyleneoxide (see Table 3) As shown in Table 3, PO conversionand isomer selectivity (the ratio of 1-methoxy-2-propanol/total propylene glycol methyl ether) reached 3 3% without the presented catalysts, Amongthe catalysts, the amine-free porous silica showed the lowcatalytic activity due to the weak acid strength of the surfacesilanol For anchored amino groupsNH(CH2)2NH2/SiO2 and NH2/SiO2 catalysts were foundto be more active and selective than other catalysts to 1-methoxy-2-propanol after 10 h of TAPM/SiO2catalyst had low propylene oxide conversion (0%) withthe isomer selectivity of 6% TBD/SiO2,NH(CH2)2NH2/SiO2 and NH2/SiO2 catalysts all showedhigh propylene oxide conversion (>94%), but different NH(CH2)2NH2/SiO2 and NH2/SiO2 withweaker base strength had higher isomer selectivity(>82%), while TBD/SiO2 with moderate base strengthshowed lower isomer selectivity (7%) As for solid basecatalysts, catalysts with moderate base strength shouldhave good isomer selectivity [20] The lower isomer selectivityof TBD/SiO2 could be due to the big framework ofTBDThe catalysts were easily recovered by filtration, andsubjected to utilization for seven cycles with constant conversionof propylene oxide >89% and the utilization formany recycles hardly changed the isomer selectivity under403 K (see Table 4), indicating that amine groups graftedonto silica surface were stable under the experimental The reusability of other samples was similar to thatof NH2/SiO Possible mechanismInorganic solid base catalysts have been extensively usedfor the synthesis of propylene glycol methyl ether frommethanol and propylene oxide [31], in which, the methoxideion and proton was absorbed on acidic and basic siteson the catalyst surface, respectively, and then the methoxideion attacked the C(1) In the present case, however,the samples used for the reaction were characteristicof single site, , the catalyst with unique basic site similarto the homogeneous Because there was no Lewisacidic site on the catalysts, the mechanism should be differentfrom those involving bifunctional The plausiblemechanism of 1-methoxy-2-propanol formation onNH2/SiO2 is illustrated in Scheme There was H-bondsformation between methanol and amine groups in path In path 2, because of the sterically hindered CH3 of PO, theO atom in methanol attacked the C(1) position and protonwas absorbed on the basic sites of the catalysts, and thenC(1)–O band cracked, followed by pick up the proton toform 1-methoxy-2-It seems reasonable to consider that the higher activityof NH(CH2)2NH2/SiO2, NH2/SiO2 and TBD/SiO2 wasdue to the appropriate base strength, which could not onlyform H-bond but also crack it TAPM/SiO2 withvery weak base strength could only form more unstableH- Thus, the activity of TAPM/SiO2 was lower thanthe other On condition that such mechanism isreasonable, the big framework of the organic groups probablycould affect the attacking position of the O atom As a result, TBD of the big framework led tolower isomer Thus, both appropriate basestrength and simple framework of the organic groups wereimportant for the high conversion and good selectivity to1-methoxy-2- ConclusionsThe results presented above led to the following conclusions:(1) the efficient ultrasonic technique could successfullyprepare the amine functionalized porous silicacatalysts, (2) the characterization indicated that the aminegroups were grafted onto the silica surface by covalentbond, (3) appropriate base strength and simple frameworkof the organic groups were important for the high conversionand good selectivity to 1-methoxy-2-propanol, (4) thecatalysts could be recovered by filtration and were subjectedto utilization for many cycles with constant

翻译后:合成丙二醇甲醚超过胺改性多孔二氧化硅超声技术学张甲，乙，温榆河张甲，乙，平利，赵宁，魏伟，孙予罕， * 一个国家重点实验室，煤转化研究所，煤化学，中国科学院，太原030001 ，中国b研究生院，中国科学院，北京100039 ，中国收到2006年5月16日接见了在修订的表格2006年7月10日;接受， 2006年7月12日网上提供2006年7月21日摘要胺改性多孔二氧化硅合成了超声波技术温和条件下。样本中，其中的特点由打赌， 29 Si核磁共振光谱，元素分析和指标吸附染料，展示了光明的催化性能，对合成丙二醇甲醚由甲醇和环氧丙烷。他们都高良品率和可重用性反应，这表明超声波技术是有效的为编写有机改性二氧化硅催化剂。此外，可能的反应机制提出了合成丙二醇甲醚对这种类型的催化剂。 2006年Elsevier公司乙诉，保留所有权利。 关键词：改性多孔硅;超声波技术;环氧丙烷;甲醇;丙二醇甲醚1 。导言试图把heterogenize均相催化剂替代更传统的试剂和催化剂得到的一个领域的研究，看到了越来越大的兴趣。 许多近期的工作重点是编制有机固体基地，以heterogenize均相胺类催化剂。改造过程中普遍经营搅拌，加热，回流等[ 1-3 ] 。 最近，有兴趣的合成声化学反应成长[ 4 ] 。超声波技术已被广泛适用于两相系统由于其自身的优势，如由于精度高，速度快。大多数的这些反应都涉及非均相化学相互作用[ 5 ] 。在面积多孔材料官能化有机群体， 然而，只有有限的应用超声已探索[ 6,7 ] 。在目前的工作，另一种合成航线，形成胺改性炭黑开发用超声波能量，能产生化学修改对固体汽蚀现象[ 8 ] 。 该胺改性二氧化硅''单网站''基地实力分别有前途的催化剂为各种各样的反应[ 9 ] 。 合成乙二醇醚超过基准催化剂是一个重要的一种反应，在有机合成中。有几种方法合成丙二醇甲醚[ 10,11 ] 。其中环氧丙烷的方法大多是方便和工业可行的。一般来说，丙烯氧化反应脂肪醇经酸或基地的催化作用。 用催化剂，在这个过程中，包括先前同质基地或酸（氢氧化钠，酒类钠和三氟化硼） ，后来固体酸和基地。然而，很少有研究报道使用胺改性氧化硅为催化剂合成丙二醇甲醚，虽然无机坚实基础催化剂表现良好的活性，在反应。该固定氨基酸职能上孔支持，而这是与''单网站''基地实力，可负担不起实现这种反应。 在当前的工作中，胺官能二氧化硅催化剂包括nh2/sio2 ，中NH （ Ⅱ ） 2nh2/sio2 ， tapm / 二氧化硅（ 2,4,6 - triaminopyrimidine /二氧化硅）和tbd/sio2 （ 1,5,7 - triazabicyclo [ 4,4,0 ] dec-5-ene/sio2 ） ，准备3 -氨丙基三甲氧基硅烷（ aptms ） ， N -二[ 3 -（三methoxysilyl ）丙基]乙二胺（ edptms ）和3个- chloropropyltrimethoxysilane （ cptms ）作为耦合代理商，由超声波技术在温和的实验条件。在同一时间，以证实优点超声波技术， nh2/sio2还编写了传统的方法，以了解有效行为超声波技术在编写功能化多孔二氧化硅。此外，催化活性有机固体碱催化剂的评价由合成丙二醇甲醚从甲醇和环氧丙烷。此外，尽可能反应机理，提出了为合成丙烯乙二醇甲醚对这种类型的催化剂。 2 。实验1 。合成催化材料该胺官能二氧化硅催化剂，可取得了两方面的类似条件下，作为报早些时候[ 7 ] 。 aminopropylsilyl官能二氧化硅编写如下： 0克二氧化硅预热为12小时，在473 K的真空，以消除所有吸附水分，但地表哦小组，并比冷却下来，以室温在真空和转入250毫升三角烧瓶。 混合后，与0毫升环己烷和0毫升aptms ，混合在三角烧瓶投入超声波浴2小时（ sheshin ，日本，经营权60瓦特） 在常温下。该催化剂，然后得到了提取与甲苯在索氏提取器近一个时期以来24 h和干燥，在333 K的真空。同样的方法已用于编制中NH （ Ⅱ ） 2nh2/sio2 。 tbd/sio2编写了两个步骤：二氧化硅是第一改性3 - chloropropyltrimethoxysilane途经同一法，因为这对aminopropylsilyl官能二氧化硅和chloropropylsilyl官能二氧化硅当时反应与tbd （ 0 g ）在环己烷（ 0毫升） 。由此治理后，由超声波振动1每小时随后， 催化剂，获得了提取与甲苯在索氏提取器近一个时期以来， 24小时和干燥333 K的真空。同样的方法已用于编制对tapm/sio2 。 2 。表征内容的碳，氮和氢在所有样品的测定用vario下午分析器。该比表面积，总孔容和平均孔隙直径测量N2吸附-解吸方法一micromeritics ASAP的2000文书（的Norcross 加文） 。表面地区进行了计算打赌方法，以及孔径分布得到运用bjh孔隙分析，以氮气吸附- 脱附等温线。 29 Si核磁共振谱录就bruker平均海面- 400分光计。该基地的实力样品检测哈米特指标。 3 。催化试验催化性能测试在75毫升一批反应堆与摩尔比的甲醇和环氧丙烷正在5:1 。运行后，在403 K的10小时下磁悲壮，反应堆冷却下来到室温。 该产品，然后再过滤和分析，由气相色谱仪与火焰离子化检测后，离心脱离催化剂。催化剂洗涤溶剂，并用于回收试验。 3 。结果与讨论1 。改性多孔二氧化硅与胺群体内容的碳，氮和氢无胺多孔硅和所有改性样品进行了元素分析。 wtorg 。和Norg 。 ％ 获得由n ％ ， c ％和H ％ （见表1 ） 。结果这有没有碳和氮在无胺多孔二氧化硅。因此，碳和氮在改性样品中，必须从有机硅烷。 元素分析表明， Norg的。 ％的嫁接有机群体达到常规方法称为从文献[ 12 ] 13 mmol / g上升，这是迄今为止低于该样本编制的超声波技术（ 00 mmol / g上升） （见表1 ） 。这应该是由于应用超声波能量，以固体和液体， 可提供变化，包括汽蚀（气泡形成，在一个流动性）和化学反应（加速度化学反应） ，等等[ 13 ] 。作为一个结果，过程包括颗粒大小修饰，清洗表面或形成新鲜[ 14,15 ] ，可获得了在非均匀介质中，在固液界面。 至于把有机改性的多孔硅，汽蚀现象所带来的超声波能加快液体转移速度在孔多孔材料与液固界面。因此，采用液体有机硅烷可以很好地接触silanol群体对内壁的多孔二氧化硅反应与他们在很短的时间，搅拌，而不能达到这种效果。 因此，改造过程中完成了简单迅速超声。 在29 Si核磁共振光谱在固体状态表示共价键之间形成silylant代理人和silanol 集团对二氧化硅表面（见图1 ） 。两个共振在109和99 ppm的原因可能是29 Si原子核四泗O型硅联系（第四季）和29 Si原子核经三泗O型硅的联系和一个哦（第三季） [ 16 ] ，分别为。 该共振，在58和67 ppm的被分配以RSI公司（ OSI ）以（ OH ） 2和的RSI （ OSI ）以3 ，分别为[ 17 ] ，其中说明成功的有机官能团的多孔二氧化硅有机群体通过共价键。的C / N 值（摩尔比） ，也可以在一定程度上反映嫁接反应silanol群体和有机硅烷[ 18 ] 。 nh2/sio2 ，中NH （ Ⅱ ） 2nh2/sio2和tbd/sio2显示的C / N = 3-5 ， 5-0和3月3日至3月6日，分别。该结果，同时也表明锚碇胺群体四O型硅债券。这个同意的结果，该29sinmr谱。 2 。结构和碱度的样本图。二显示器N2吸附等温线为样本研究。该官能样品展示IV型等温线具有明确的滞后环与毛细管冷凝水气。这表明，在材料仍孔之前和之后官能和改性各种有机硅烷难以改变等温式。比表面积和孔容表明逐渐减少为易。 ％嫁接有机群体的增加（见表2 ） 。这可能是归功于在场的功能群。一部分氨基接枝微孔，也引发了一场跌幅在比表面积。效果有机集团对孔径的样品为轻度样本nh2/sio2和NH （ Ⅱ ） 2nh2/sio2 。但正如为样本tbd/sio2和tapm /二氧化硅，也许是因为以大框架内（ Ⅱ ） 3/tapm和（ Ⅱ ） 3 / tbd群体，其平均孔径的样本下降到90和82 nm左右。然而，平均孔隙直径为没有减少，严重由于低Norg的。 ％ 值的样本。 该基地强度H类固体表面定义为有能力的表面转换成一种吸附电中性酸纳入其共轭基地。当一个电中性酸指标是吸附了坚实的基础，从非极性溶液，色条酸指标是改变现在说的，其共轭基地，只要扎实拥有必要的基础力量，传授电子对向酸[ 19 ] 。了坚实的一大正面有个HH 强大的基本地盘。嫁接不同功能组别可能会导致不同的基本优势。如表3 ， tbd/sio2有最高碱强度的H 0 ， 而nh2/sio2和NH （ Ⅱ ） 2nh2/sio2不仅有碱度的H 3和3 < h < 0 ，分别。 其它城市相比，改性样品， tapm/sio2 曾最弱碱度的H < 2 。因此，基本实力该样本是在常规的tbd / 二氧化硅>中NH （ Ⅱ ） 2nh2/sio2 > nh2/sio2 > tapm/sio2 。 3 。催化性能催化活性测试，在合成丙烯乙二醇甲醚由甲醇和丙烯氧化氮（见表3 ） 。如表3所示，宝转换和同分异构体的选择性（比例为1 -甲氧基-2 -丙醇/ 总丙二醇甲醚）达到3和3 ％ ，但无提交催化剂，分别。其中催化剂，无胺多孔二氧化硅显示低催化活性由于弱酸强度的表面silanol群体。为锚定氨基酸组中NH （ Ⅱ ） 2nh2/sio2和nh2/sio2催化剂被发现以更积极和选择性比其他催化剂，以1 - 甲氧基-2 -丙醇后， 10小时的反应。 tapm/sio2 催化剂低环氧丙烷转化率（ 0 ％ ） 该异构体的选择性为6 ％ 。 tbd/sio2 ， 中NH （ Ⅱ ） 2nh2/sio2和nh2/sio2催化剂都显示高环氧丙烷转化率（ " > 94 ％ ） ，但不同的异构体异构体选择性。中NH （ Ⅱ ） 2nh2/sio2和nh2/sio2与弱基强度较高，同分异构体的选择性（ " > 82 ％ ） ，而tbd/sio2中度基地实力表明较低的异构体选择性（ 7 ％ ） 。至于奠定了坚实的基础催化剂，催化剂与温和的基地实力应具有良好的异构体选择性[ 20 ] 。较低的异构体的选择性对tbd/sio2可能是由于大范围内tbd 。 该催化剂易于回收过滤，并受到利用7个周期不断转换环氧丙烷> 89 ％和综合利用许多回收难以改变异构体选择性下403的K （见表4 ） ，说明胺集团嫁接到二氧化硅的表面稳定，在实验条件下。 可重用的其他样品类似这对nh2/sio2 。 4 。可能的机制无机固体碱催化剂已广泛使用为合成丙二醇甲醚从甲醇和环氧丙烷[ 31 ] ，其中，甲醇离子和质子吸收，对酸和基本地盘对催化剂的表面，分别，然后甲醇离子攻击的C （ 1 ）的位置。在本案件中，但是， 该样本用于该反应的特点单一网站，即该催化剂具有独特的场址基本相似向同质基地。因为没有刘易斯酸性网站上的催化剂，该机制应有所不同从那些涉及双功能催化剂。收益机理1 -甲氧基-2 -丙醇形成nh2/sio2体现在计划1 。还有的H -债券形成以甲醇及胺组在道路in路径2 ，因为该阻甲基蒲， 氧原子在甲醇攻击的C （ 1 ）的位置和质子被吸收就基本地盘的催化剂，然后（ 1 ）邻带侦破，然后拿起质子以表1 -甲氧基-2 -丙醇。 似乎可以合理地认为，较高的活性中NH （ Ⅱ ） 2nh2/sio2 ， nh2/sio2和tbd/sio2是由于合适的基地实力，而不能只形成氢键，而且裂缝的，它很容易。 tapm/sio2与十分薄弱，基础实力，只能形成更多的不稳定氢键。因此，活性tapm/sio2低于其他样本。条件是这种机制合理的，大框架内的有机群体，大概可能会影响攻击的立场与氧原子在甲醇。因此， tbd的大框架内，导致较低的异构体的选择性。因此，既恰当基地实力和简单的框架的有机群体对于高转化率和选择性好，以1 -甲氧基-2 -丙醇。 4 。结论结果提交以上可以得出以下结论： （ 1 ）高效率的超声波技术可以成功准备胺官能多孔二氧化硅催化剂， （ 2 ）表征表示胺团体接枝二氧化硅表面共价债券， （ 3 ）适当的基础实力和简单框架的有机群体重要的是转化率高选择性好，以1 -甲氧基-2 -丙醇， （ 4 ） 催化剂可以回收过滤和遭受以综合利用为许多个周期不断的活动。