CN109096074B - 一种2-乙基丙烯醛的合成方法 - Google Patents
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- 238000001308 synthesis method Methods 0.000 title description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 48
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims abstract description 44
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims abstract description 44
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 13
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- 238000006555 catalytic reaction Methods 0.000 claims abstract description 4
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- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 35
- 239000000203 mixture Substances 0.000 claims description 11
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 6
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- 238000004321 preservation Methods 0.000 claims description 3
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- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 claims 1
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- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 238000004821 distillation Methods 0.000 description 11
- 239000007788 liquid Substances 0.000 description 8
- XIKVGYYSAJEFFR-UHFFFAOYSA-N 2-(hydroxymethyl)butanal Chemical compound CCC(CO)C=O XIKVGYYSAJEFFR-UHFFFAOYSA-N 0.000 description 6
- HYFFNAVAMIJUIP-UHFFFAOYSA-N 2-ethylpropane-1,3-diol Chemical compound CCC(CO)CO HYFFNAVAMIJUIP-UHFFFAOYSA-N 0.000 description 6
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- XVOKUMIPKHGGTN-UHFFFAOYSA-N Imazethapyr Chemical compound OC(=O)C1=CC(CC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 XVOKUMIPKHGGTN-UHFFFAOYSA-N 0.000 description 1
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- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
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- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
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Abstract
本发明公开了一种2‑乙基丙烯醛的合成方法，属于有机合成技术领域。将正丁醛与甲醛在二正丁胺和B(C6F5)3混合体系催化下40‑60℃反应2‑4h，反应液静置分层，取有机层加入0.1%‑0.5%的阻聚剂，常压蒸馏得到无色透明产品2‑乙基丙烯醛，加入0.1%‑0.5%阻聚剂保存。本发明路线操作简单，反应副产物少，产品纯度高，不易聚合，产品具有竞争优势。
Description
技术领域
本说明涉及一种2-乙基丙烯醛的合成方法，属于有机合成技术领域。
背景技术
2-乙基丙烯醛，无色透明液体，沸点：92-93℃，CAS的编号为922-63-4，分子式为C5H8O，为除草剂咪唑乙烟酸的中间体。
现有技术方法，其制备方法是在反应釜中加入甲醛和正丁醛，在碳酸钠、碳酸钠/四丁基溴化磷、四氢吡咯/丙酸、碳酸钠/十二烷基硫酸钠、三乙胺、氢氧化钠、二乙胺盐酸盐或二乙胺/乙酸等体系存在下反应，升温回流反应，冷却分层，有机层水洗而得到成品。
以上方法反应副产物多，产品含量不高，色泽差，收率偏低。主要副产物为2,2-羟甲基丁醛和2,2-羟甲基丁醇，该副产物与产品共沸，蒸馏时提纯困难，在升高温度精馏时产品为浅黄色液体。
发明内容
为了克服现有技术的不足，本发明提供了由正丁醛与甲醛在仲胺-强路易斯酸组合下共同催化脱水，反应结束蒸馏和产品阶段通过加入阻聚剂的方式实现。
为了实现上述目的，本发明采用如下技术方案，包括如下操作：正丁醛与甲醛在二正丁胺和B(C6F5)3混合体系催化下，控制在40-60℃反应，反应液静置分层，取有机层0.1%-0.5%的阻聚剂，常压蒸馏得到无色透明液体2-乙基丙烯醛加入0.1%-0.5%阻聚剂保存。
进一步地，在上述技术方案中，所述正丁醛与甲醛摩尔比例为1:1.05-1.2，甲醛选自35-40%甲醛溶液或多聚甲醛。
进一步地，在上述技术方案中，所述二正丁胺是滴加方式进料。二正丁胺与B(C6F5)3质量比为2-3: 1。
进一步地，在上述技术方案中，所述二正丁胺用量为正丁醛质量5-20%。
进一步地，在上述技术方案中，所述蒸馏首选阻聚剂选自对苯二酚、对羟基苯甲醚或2,6-二叔丁基苯酚。
进一步地，在上述技术方案中，所述2-乙基丙烯醛合格指标：无色透明液体，含量大于99%，加入0.1%-0.5%阻聚剂保存。
发明的有益效果
本发明采用正丁醛与甲醛在二正丁胺和B(C6F5)3共同催化下反应，副产物2,2-羟甲基丁醛和2,2-羟甲基丁醇可以有效控制在2%以下，反应结束蒸馏和保存阶段通过加入阻聚剂，得到无色透明产品，产品纯度高达99.5%以上。本发明路线操作简单，反应副产物少，产品纯度高，不易聚合，产品具有竞争优势。
具体实施方式
实例一：反应需正丁醛144g、35%甲醛溶液188.6g、二正丁胺14.4g和4.8g B(C6F5)3，正丁醛与甲醛摩尔比例为1:1.1，控制40-60℃下滴加二正丁胺和B(C6F5)3，维持40-60℃保温反应2h后静置分层。有机层加入对苯二酚0.2%当量，蒸馏得到2-乙基丙烯醛加入对苯二酚0.2%当量保存。
合成方法如下：
(1)向500mL反应瓶加入正丁醛和35%甲醛溶液（2）滴加二正丁胺和B(C6F5)3混合物，控温在40-60℃（3）滴加完毕后保温在40-60℃搅拌2小时后，取样分析2-乙基丙烯醛、2,2-羟甲基丁醛和2,2-羟甲基丁醇三者比例为：98.3%、0.9%和0.8%，静置分层（4）有机层加入对苯二酚0.2%当量蒸馏得到无色液体2-乙基丙烯醛158g加入对苯二酚0.2%当量，GC含量99.8%，收率94%。
实例二：反应需正丁醛144g、35%甲醛溶液171g、二正丁胺14.4g和7.2g B(C6F5)3，正丁醛与甲醛摩尔比例为1:1，控制40-60℃下滴加二正丁胺和B(C6F5)3混合物，维持40-60℃保温反应2h后静置分层。有机层加入对苯二酚0.5%当量，蒸馏得到2-乙基丙烯醛加入对苯二酚0.5%当量保存。
合成方法如下：
(1)向500mL反应瓶加入正丁醛和35%甲醛溶液（2）滴加二正丁胺和B(C6F5)3混合物，控温在40-60℃（3）滴加完毕后保温在40-60℃搅拌2小时后，取样分析2-乙基丙烯醛、2,2-羟甲基丁醛和2,2-羟甲基丁醇三者比例为：96.4%、1.7%和1.9%，静置分层（4）有机层加入对苯二酚0.2%当量蒸馏得到无色液体2-乙基丙烯醛144.5g加入对苯二酚0.2%当量，GC含量99.7%，收率86%。
实例三：反应需正丁醛144g、多聚甲醛63g、二正丁胺14.4g和4.8g B(C6F5)3，正丁醛与甲醛摩尔比例为1:1.05，控制40-60℃下滴加二正丁胺和B(C6F5)3混合物，维持40-60℃保温反应1h后静置分层。有机层加入对苯二酚0.1%当量，蒸馏得到2-乙基丙烯醛加入对苯二酚0.1%当量保存。
合成方法如下：
(1)向500mL反应瓶加入正丁醛和多聚甲醛（2）滴加二正丁胺和B(C6F5)3混合物，控温在40-60℃（3）滴加完毕后保温在40-60℃搅拌1小时后，取样分析2-乙基丙烯醛、2,2-羟甲基丁醛和2,2-羟甲基丁醇三者比例为：97.9%、1.3%和0.8%，静置分层（4）有机层加入对苯二酚0.1%当量蒸馏得到无色液体2-乙基丙烯醛156g加入对苯二酚0.1%当量，GC含量99.5%，收率93%。
实例四：反应需正丁醛144g、多聚甲醛72g、二正丁胺28.8g和14.4g B(C6F5)3，正丁醛与甲醛摩尔比例为1:1.2，控制40-60℃下，滴加二正丁胺和B(C6F5)3混合物，维持40-60℃保温反应2h后静置分层。有机层加入对苯二酚0.2%当量，蒸馏得到2-乙基丙烯醛加入对苯二酚0.2%当量保存。
合成方法如下：
(1)向500mL反应瓶加入正丁醛和多聚甲醛（2）滴加二正丁胺和和B(C6F5)3混合物，控温在40-60℃（3）滴加完毕后保温在40-60℃搅拌2小时后，取样分析2-乙基丙烯醛、2,2-羟甲基丁醛和2,2-羟甲基丁醇三者比例为：97.4%、1.6%和1.0%，静置分层（4）有机层加入对苯二酚0.2%当量蒸馏得到无色液体2-乙基丙烯醛158.7g加入对苯二酚0.2%当量，GC含量99.8%，收率94.5%。
以上仅为本发明较佳的具体实施方式，但本发明的保护范围并不局限于此，任何熟悉本技术领域的技术人员在本发明披露的技术范围内，根据本发明的技术方案及其发明构思加以等同替换或改变，都应涵盖在本发明的保护范围之内。
Claims (4)
1.一种2-乙基丙烯醛的合成方法，其特征在于，包括如下操作：将正丁醛与甲醛在二正丁胺和B(C6F5)3混合体系催化下40-60℃反应，反应液静置分层，取有机层0.1%-0.5%的阻聚剂，常压蒸馏得到2-乙基丙烯醛，加入0.1%-0.5%阻聚剂保存；所述二正丁胺B(C6F5)3混合物采用滴加方式加入，二正丁胺与B(C6F5)3质量比为2-3: 1；所述二正丁胺加入量为正丁醛质量5-20%。
2.根据权利要求1所述2-乙基丙烯醛的合成方法，其特征在于：甲醛选自35-40% 甲醛溶液或多聚甲醛。
3.根据权利要求1所述2-乙基丙烯醛的合成方法，其特征在于：正丁醛与甲醛摩尔比例为1: 1.05-1.2。
4.根据权利要求1所述2-乙基丙烯醛的合成方法，其特征在于：阻聚剂选自对苯二酚、对羟基苯甲醚或2,6-二叔丁基苯酚。
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| US7820616B1 (en) * | 2009-06-09 | 2010-10-26 | International Flavors & Fragrances, Inc. | Cyclic acetal compounds and their use in perfume compositions |
| CN106687437A (zh) * | 2014-09-18 | 2017-05-17 | 赢创罗姆有限公司 | 制备甲基丙烯醛的优化方法 |
| CN109096074A (zh) * | 2018-09-08 | 2018-12-28 | 湖北荆洪生物科技股份有限公司 | 一种2-乙基丙烯醛的合成方法 |
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| 以甲醛和丙醛为原料制备甲基烯丙醇的催化反应过程研究;戴海荣;《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》;20180415(第04期);第19-21页、第24-25页 * |
| 甲醛和丙醛缩合制备甲基丙烯醛反应动力学;李玉超等;《过程工程学报》;20120815(第04期);第603页第2段、第606页结论部分 * |
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