克酮酸的合成研究

化工論文編號:HG024  字數:8603,頁數:23

目 錄
引言…………………………………………………………………………………………1

第一章 克酮酸的合成綜述……………………………………………………………2
  1.1克酮酸的簡介………………………………………………………………………… 2
  1.2克酮酸的用途………………………………………………………………………2
  1.3克酮酸的合成方法……………………………………………………………………3
  1.3.1 乙二醛聚合、脫羧法………………………………………………………………3
  1.3.2四氯苯醌經甲基化、水解、氧化脫羧法………………………………………3
  1.4研究目的及其意義……………………………………………………………………4
第二章 實驗部分………………………………………………………………5
  2.1實驗原理………………………………………………………………………………5
  2.2 實驗儀器、試劑………………………………………………………………5
  2.2.1實驗儀器……………………………………………………………………………5
  2.2.2試劑…………………………………………………………………………………6
  2.3 實驗步驟………………………………………………………………………………7
  2.3.1四甲氧基苯醌的合成………………………………………………………………7
  2.3.2 四羥基苯醌的合成…………………………………………………………………8
  2.3.3克酮酸的合成………………………………………………………………………8
第三章 結果與討論 ……………………………………………………………………10
  3.1四氯苯醌甲氧基取代反應過程及影響因素…………………………………………10
  3.1.1反應中反應液中含水率對反應結果的影響………………………………10
 3.1.2 回流前反應冷卻溫度對結果的影響 ……………………………………………10
  3.2四甲氧基苯醌水解反應過程及其影響因素………………………………………11
  3.2.1氫溴酸和醋酸摩爾比對反應結果的影響…………………………………………11
  3.2.2 HCl濃度對實驗結果的影響………………………………………………………12
  3.3四羥基苯醌反應制克酮酸過程及其影響因素………………………………13
 3.4 最佳實驗條件的驗證 ………………………………………………………………14
結論……………………………………………………………………………16
致謝……………………………………………………………………………17
參考文獻………………………………………………………………………18

摘要：克酮酸是一種重要的化學中間體，用途十分廣泛。現今克酮酸被用于生物分析領域，是與生物分子共價結合的近紅外熒光染料。此外克酮酸染料是一類新型的近紅外吸收染料，由于具有良好的光熱穩定行和熒光發光性能，因而在光學記錄與存儲領域有著潛在的應用價值。研究了克酮酸的新合成路線,以四氯苯醌為原料,經甲氧基化,水解,氧化脫羧三步制得高純度的克酮酸。和從乙二醛出發的傳統制法相比,該路線原料易得,條件溫和,總收率可達35%,高于傳統法的收率約10%。反應以四氯苯醌為原料，合成高純度的克酮酸（4,5-二羥基-4-環戊烯-1，2，3，-三酮）。整個反應通過六個步驟的研究，并得到了反應的最佳條件，具體如下：
 1) 四甲氧基苯醌過程中所用甲醇溶液必須為無水甲醇，在回流反應前溶液冷卻后的溫度15℃，然后進一步回流反應；
 2) 甲氧基苯醌水解反應過程中，當氫溴酸與醋酸摩爾比為1:1時，四羥基苯醌與2mol/L的鹽酸溶液中重結晶產品收率最佳；
 3) 制備克酮酸的過程中加入濃硫酸的量為0.4ml時，產品收率最理想。
 經過優化的工藝條件比傳統路線反應條件溫和，收率高，為克酮酸的制備和工業化生產開辟了一條新的途徑。
關鍵詞：克酮酸；四氯苯醌；四甲氧基苯醌；四羥基苯醌；合成

Study on the New Synthetic Process of Croconic Acid
Abstract：The crocic acid is in the center a kind of important chemistry body, the use is very extensive.The crocic acid is used for living creature analysis realm, is the near red and outside fluorescence dyestuff that combines with the living creature member covalence at present.In addition the crocic acid dyestuff is a type of new near and red outside absorption dyestuff, in order to having, the good light heat stabilizes to go to give out light to go with fluorescence ability, as a result at optical record with saving the realm have latent of applied value.Studied a lately synthesizing of the crocic acid route, take tetrachlorobenzoquinone as raw material, Be turned by AN oxygen radicle, water solution, oxidize to take off Zui three step systems Gao Chun Du's crocic acid.The traditional method for making setting out with two Quans from B compares, the route's raw material easily get, the condition is moderate, always accepting a rate cans reach to 35%, is farer high than about 10% of traditional method.Respond to set out and synthesize Gao Chun Du's crocic acid from the tetrachlorobenzoquinone.((or4,5-dihydroxy-4-cyclopentene-1,2,3-trione)The whole reaction passes six researches of steps, and got the best condition of reaction, concretely as follows:
 1)The methyl alcohol aqua used in the etramethoxy process have to in order to have no water methyl alcohol, the aqua cools off the temperature of empress 15 ℃ before the reflux responds, then the further reflux responds;
 2)AN oxygen radicle benzene Mao water solution reaction process in, the hydrogen bromine is sour with acetic acid Mo Er compare for 1:be tetrahydroxy and 2 mols at 1:00|weigh to crystallize in the L hydrochloric acid aqua, the product accepts to lead superior turn;
 3)The product accepts to lead while making to join the measuring of oil of vitriol as 0.4 mls in the process of crocic acid the most ideal.
 After excellent craft condition for turning compare traditional route reaction the condition is moderate and accept to lead higher, developed a new path for a great deal of making and industrialization production of crocic acid.
Keywords：crocic acid；tetrachlorobenzoquinone； etramethoxy-1, 4-benzoquinone； tetrahydroxy-1, 4-benzoquinone；synthesis