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摘要：本文概述了新铃兰醛的香气特征和在调香领域的应用价值。综述了自IFF开发新铃兰醛以来的相关重要的文献报导。文献主要围绕对碳-碳双键或对碳-氧双键的保护以减少异构化发生。但工业上对于“保护-脱保护”过程带来环保和成本的压力也很头痛。而“不加保护”的文献报导产物选择性低，鲜有工业价值的结果。在比较前人工作的基础上提出在合适的催化体系中、温和条件下进行水合反应以保证产物的选择性，最终结合“反应-蒸馏”的化学工程手段合成新铃兰醛。从而有效避开水合反应进入转化率平台区后选择性急剧下降的问题。本文以柑青醛为原料，对醛基未加保护直接水合合成新铃兰醛。以阳离子交换树脂D72为水合反应主催化剂，配合助催剂A，使反应达到较佳的转化率/选择性综合结果。本文筛选出以柑青醛：水：助催剂A是7：3：14（质量比）为较佳物料配比，在此配比下在80℃水合反应2小时，色谱得率15.3%，摩尔选择性85.7%。产物经GCMS检测确认为新铃兰醛结构。该结果符合进行原料蒸馏回收的基本要求。为完成该课题的“反应-蒸馏”的思路打下有价值的基础。24748
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毕业论文关键词：柑青醛；直接水合反应；新铃兰醛；阳离子交换树脂
Study on Green Synthesis of Lyral
Abstract: The article outlines the olfactive note and the perfumery applications of Lyral, reviews the related publications since Lyral being developed by IFF. The common topic for these publications is to protect carbon-carbon double bond or carbon-oxygen double bond to minimize isomerization. For those “non-protection” reports, they far to meet industrial value due to low yield. Based on the previous studies, we propose the route of direct hydration of myrac aldehyde without protecting aldehyde group to synthesize Lyral under an appropriate catalyst system and mild conditions in order to ensure the selectivity of Lyral, and furthermore follows by the chemical engineering method of “reaction-distillation”, which aims to avoid the substantial selectivity drop against post reaction speed peak. The effects of various parameters were investigated in detail using D72 cation exchange resin as main catalyst and polar reagent A as sub-catalyst in a stirred reactor。and achieved a good conversion/selectivity balance. With the feedstock ratio by weight as: Myrac aldehyde 7, water 3 and sub-catalyst A 14, under 80℃ for 2 hours, we get Lyral yield 15.3% (by GC) and 85.7% mole selectivity，a result with
good conversion/selectivity balance. The product structure is proven by GCMS. The results look promising for next step of feedstock recovery by distillation. We believe this paper offer useful approach for implementation of “reaction-distillation” concept in Lyral synthesis.
Key Words: Myrac aldehyde, direct hydration reaction, Lyral, cation exchange resin
目录
1 前言 1
1.1 由月桂烯合成月桂烯醇再与丙烯醛反应制备新铃兰醛 1
1.1.1 月桂烯合成月桂烯醇 2
1.1.2 月桂烯醇合成新铃兰醛 2
1.2 由月桂烯合成柑青醛后制备新铃兰醛 3
1.2.1 月桂烯合成柑青醛 3
1.2.2 柑青醛合成新铃兰醛 4
2 实验内容和实验方法 7
2.1 实验原料、药品与设备 7
2.2 化学反应 8
2.3 实验装置与步骤 8
2.4 分析方法 9
2.4.1 气相色谱定量分析 9
2.4.2 反应物转化率、产物选择性和收率的计算分析 9
3 结果与讨论 11
3.1 催化体系的确立 11
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