WO2018095359A1 - 一种三官能度化合物及其制备方法和应用 - Google Patents

一种三官能度化合物及其制备方法和应用 Download PDF

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WO2018095359A1
WO2018095359A1 PCT/CN2017/112581 CN2017112581W WO2018095359A1 WO 2018095359 A1 WO2018095359 A1 WO 2018095359A1 CN 2017112581 W CN2017112581 W CN 2017112581W WO 2018095359 A1 WO2018095359 A1 WO 2018095359A1
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dichloromethane
benzene
trifunctional compound
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solid
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戴李宗
吴俣哲
袁丛辉
毛杰
李云同
常迎
吴海洋
许一婷
曾碧榕
罗伟昂
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Xiamen University
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    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/42—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/44—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a carbon atom of an unsaturated carbon skeleton
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    • C—CHEMISTRY; METALLURGY
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/36—Amides or imides
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    • C30B29/00—Single crystals or homogeneous polycrystalline material with defined structure characterised by the material or by their shape
    • C30B29/60—Single crystals or homogeneous polycrystalline material with defined structure characterised by the material or by their shape characterised by shape
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    • C—CHEMISTRY; METALLURGY
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    • C30B29/00—Single crystals or homogeneous polycrystalline material with defined structure characterised by the material or by their shape
    • C30B29/60—Single crystals or homogeneous polycrystalline material with defined structure characterised by the material or by their shape characterised by shape
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  • the invention belongs to the technical field of organic synthesis, and in particular relates to a trifunctional compound and a preparation method and application thereof.
  • Materials are indispensable material guarantees for social production and operation. At the same time as the progress of productivity and the development of science and technology, various new requirements have been put forward on the types and functions of materials. Because of its regular chemical space structure and versatility, crystal materials have been widely used in materials processing, mechanics, optics, and electrical fields, thus meeting a large number of people's demand for materials.
  • Another object of the present invention is to provide a process for the preparation of the above trifunctional compound.
  • a further object of the present invention is to provide the use of the above trifunctional compounds in crystal culture.
  • the preparation method of the above trifunctional compound comprises the following steps:
  • the ratio of the above 1,3,5-tris(4-aminophenyl)benzene, lithium chloride solid, triethylamine, dichloromethane and methacryloyl chloride is 2 to 17 g: 5 to 15 g: 10 to 45 mL: 45 ⁇ 65mL: 15 ⁇ 55mL.
  • the ratio of the 1,3,5-tris(4-aminophenyl)benzene, lithium chloride solid, triethylamine, dichloromethane and methacryloyl chloride is 3 to 15 g: 5 to 14 g: 10 to 40 mL: 50 to 60 mL: 20 to 50 mL.
  • a method of culturing crystals using the above trifunctional compound comprising the steps of:
  • the material obtained in the step (1) is placed in a constant temperature incubator with a strict temperature control of 16 ° C, the culture vessel is kept open, and the door of the incubator is closed to ensure that the independent environment in the incubator is not disturbed by external conditions. After standing for at least 72h, a large number of needle-like and long strips of crystals can be grown;
  • the ratio of the above trifunctional compound, dichloromethane and ethyl acetate is 2 to 6 g: 25 to 65 mL: 80 to 250 mL.
  • the ratio of the trifunctional compound, dichloromethane and ethyl acetate is 2 to 5 g: 30 to 60 mL: 100 to 200 mL.
  • the trifunctional compound of the present invention 1,3,5-tris(4-methacryloylaminophenyl)benzene, has a well-designed chemical structure with three double bonds and has versatility.
  • the preparation method of the invention has simple synthesis route, mature process, high product purity and low cost.
  • the method for cultivating crystals of the present invention has the advantages of simple and convenient operability, simple device, good repeatability, and large-scale cultivation of crystals.
  • the method of culturing crystals of the present invention is capable of cultivating a crystalline material having a good crystal form, and has special optical and mechanical properties.
  • the crystals cultivated by the present invention also have the characteristics of having three unsaturated double bonds in the same monomer, which can be copolymerized with various monomers having double bonds to form various multifunctional copolymers.
  • Figure 1 is a nuclear magnetic resonance spectrum of a trifunctional compound prepared by the present invention, and its nuclear magnetic spectroscopy is: 9.93 (3H, s), 7.90 to 7.81 (15H, m), 5.87 (3H, s), 5.53 (3H, s ), 2.1 (9H, s),.

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Abstract

本发明公开了一种三官能度化合物及其制备方法和应用，其名称为1,3,5-三(4-甲基丙烯酰氨苯基)苯，其结构式为：本发明的三官能度化合物1,3,5-三(4-甲基丙烯酰氨苯基)苯的化学结构设计巧妙，带有三个双键，具有有多功能性；本发明的制备方法的合成路线简单，工艺成熟，产物纯度高，成本低廉。

Description

一种三官能度化合物及其制备方法和应用 技术领域
本发明属于有机合成技术领域，具体涉及一种三官能度化合物及其制备方法和应用。
背景技术
材料是社会生产和运行所不可或缺的物质保障。在生产力进步和科技水平发展的同时，对材料的种类和功能也提出了各种新的要求。晶体材料因为具有规整的化学空间结构和多功能性等特点，在材料加工，力学，光学，电学等领域都得到了广泛的应用，因而满足了人们对材料方面的大量需求。
然而晶体材料的合成过程困难，工艺复杂而且耗时长，价格昂贵，不可控因素多，通常难以大量生产。这些都限制了晶体材料更进一步的研究和应用。
发明内容
本发明目的在于提供一种三官能度化合物。
本发明的另一目的在于提供上述三官能度化合物的制备方法。
本发明的再一目的在于提供上述三官能度化合物在晶体培养中的应用。
本发明的技术方案如下：
一种三官能度化合物，其名称为1,3,5-三(4-甲基丙烯酰氨苯基)苯，其结构
式为：
Figure PCTCN2017112581-appb-000001
上述三官能度化合物的制备方法，包括如下步骤：
(1)将2～4g的1,3,5-三(4-氨苯基)苯，3～6g的氯化锂固体和5～12mL三乙胺溶解于14～16mL二氯甲烷当中，接着放置于冰浴条件于搅拌25～35min；
(2)在步骤(1)所得的物料中缓慢滴加入8～22mL甲基丙烯酰氯，并且在室温条件下搅拌过夜反应；
(3)先后用蒸馏水和饱和氯化钠溶液充分洗涤步骤(2)所得的物料，再用无水硫酸钠固体干燥过夜；
(4)通过柱层析对步骤(3)所得的物料进行纯化和洗脱，即可得到无色的固体粗产物；上述洗脱剂为石油醚和乙酸乙酯的混合溶液，
(5)将步骤(4)所得的固体粗产物用无水乙醇进行重结晶，即得到所述三官能度化合物1,3,5-三(4-甲基丙烯酰氨苯基)苯；
上述1,3,5-三(4-氨苯基)苯、氯化锂固体、三乙胺、二氯甲烷和甲基丙烯酰氯的比例为2～17g:5～15g:10～45mL:45～65mL:15～55mL。
在本发明的一个优选实施方案中，所述1,3,5-三(4-氨苯基)苯、氯化锂固体、三乙胺、二氯甲烷和甲基丙烯酰氯的比例为3～15g:5～14g:10～40mL:50～60mL:20～50mL。
一种用上述三官能度化合物培养晶体的方法，包括如下步骤：
(1)将所述三官能度化合物溶解于二氯甲烷中，再稀释到装有乙酸乙酯培养容器中；
(2)将步骤(1)所得的物料放置于严格控温为16℃的恒温培养箱内，保持培养容器敞开，关闭培养箱的门以保证培养箱内的独立环境不受外界条件的干扰，静置至少72h之后，即可长出大量针状和长条状的晶体；
上述三官能度化合物、二氯甲烷和乙酸乙酯的比例为2～6g:25～65mL:80～250mL。
在本发明的一个优选实施方案中，所述三官能度化合物、二氯甲烷和乙酸乙酯的比例为2～5g:30～60mL:100～200mL。
本发明的有益效果是：
1、本发明的三官能度化合物1,3,5-三(4-甲基丙烯酰氨苯基)苯的化学结构设计巧妙，带有三个双键，具有有多功能性
2、本发明的制备方法的合成路线简单，工艺成熟，产物纯度高，成本低廉。
3、本发明的培养晶体的方法具有简便，可操作性强，装置简单，可重复性好，可以实现晶体的大量培养。
4、本发明的培养晶体的方法能够培养出具有良好晶型的晶体材料，具有特殊的光学和力学性质。
5、本发明所培养出的晶体还具有在同一个单体中同时带有三个不饱和双键,可以与各种带双键的单体进行共聚合进而生成各种多功能共聚物的特点。
附图说明
图1为本发明制备的三官能度化合物的核磁氢谱，其核磁解谱为:9.93(3H,s),7.90～7.81(15H,m),5.87(3H,s),5.53(3H,s),2.1(9H,s),。
图2为本发明制备的三官能度化合物所培养的晶体的偏光显微镜图片。
具体实施方式
以下通过具体实施方式结合附图对本发明的技术方案进行进一步的说明和描述
实施例1
(1)将4～6g的1,3,5-三(4-氨苯基)苯，8～12g的氯化锂固体和10～30mL三乙胺溶解于50mL二氯甲烷当中，放置于冰浴条件于搅拌30min。缓慢滴加进入20～30mL甲基丙烯酰氯，并且在室温条件下搅拌过夜。反应结束后，先后用蒸馏水，饱和氯化钠溶液洗涤三次，无水硫酸钠干燥过夜。通过柱层析进行纯化，洗脱剂为石油醚和乙酸乙酯，即可得到无色的固体粗产物。所得到的固体用无水乙醇进行重结晶，即得所述三官能度化合物1,3,5-三(4-甲基丙烯酰氨苯基)苯(如图1所示)。
(2)将2g上述产物溶解于30mL的二氯甲烷当中，再稀释到装有100mL的乙酸乙酯的血清瓶当中。将血清瓶放置于严格控温为16℃的恒温培养箱内。保持瓶口敞开,关闭培养箱的门以保证培养箱内的独立环境不受外界条件的干扰。静置72h之后，即可长出大量针状和长条状的晶体(如图2所示)。
实施例2
(2)将5～8g的1,3,5-三(4-氨苯基)苯，7～14g的氯化锂固体和15～40mL 三乙胺溶解于60mL二氯甲烷当中，放置于冰浴条件于搅拌30～50min。缓慢滴加进入30～40mL甲基丙烯酰氯，并且在室温条件下搅拌过夜。反应结束后，先后用100mL蒸馏水，100mL饱和氯化钠溶液洗涤三次，加入5g无水硫酸钠固体干燥过夜。通过柱层析进行纯化，洗脱剂为石油醚和乙酸乙酯的混合溶液，即可得到无色的固体粗产物。所得到的固体用100mL无水乙醇进行重结晶，即得所述三官能度化合物1,3,5-三(4-甲基丙烯酰氨苯基)苯(如图1所示)。
(2)将3g上述产物溶解于40mL的二氯甲烷当中，再稀释到装有150mL的乙酸乙酯的血清瓶当中。将血清瓶放置于严格控温为16℃的恒温培养箱内。保持瓶口敞开,关闭培养箱的门以保证培养箱内的独立环境不受外界条件的干扰。静置72h之后，即可长出大量针状和长条状的晶体(如图2所示)。
实施例3
(1)将10～15g的1,3,5-三(4-氨苯基)苯，5～10g的氯化锂固体和20～30mL三乙胺溶解于50mL二氯甲烷当中，放置于冰浴条件于搅拌30～60min。缓慢滴加入30～50mL甲基丙烯酰氯。滴加完后,让反应逐渐升温到室温,并且在室温条件下搅拌过夜。反应结束后，先后用150mL蒸馏水，150mL饱和氯化钠溶液分别洗涤三次，再加入10g无水硫酸钠固体干燥过夜。通过柱层析进行纯化，洗脱剂为石油醚和乙酸乙酯的混合溶液，即可得到无色的固体粗产物。所得到的固体用150mL无水乙醇进行重结晶，即得所述三官能度化合物1,3,5-三(4-甲基丙烯酰氨苯基)苯(如图1所示)。
(2)将5g上述产物溶解于60mL的二氯甲烷当中，再稀释到装有200mL的乙酸乙酯的血清瓶当中。将血清瓶放置于严格控温为16℃的恒温培养箱内。保持瓶口敞开,关闭培养箱的门以保证培养箱内的独立环境不受外界条件的干扰。静置72h之后，即可长出大量针状和长条状的晶体(如图2所示)。
以上所述，仅为本发明的较佳实施例而已，故不能依此限定本发明实施的范围，即依本发明专利范围及说明书内容所作的等效变化与修饰，皆应仍属本发明涵盖的范围内。

Claims (5)

  1. 一种三官能度化合物，其特征在于：其名称为1,3,5-三(4-甲基丙烯酰氨苯基)苯，其结构式为：
    Figure PCTCN2017112581-appb-100001
  2. 一种权利要求1所述的三官能度化合物的制备方法，其特征在于：包括如下步骤：
    (1)将1,3,5-三(4-氨苯基)苯，氯化锂固体和三乙胺溶解于1二氯甲烷当中，接着放置于冰浴条件于搅拌25～35min；
    (2)在步骤(1)所得的物料中缓慢滴加入甲基丙烯酰氯，并且在室温条件下搅拌过夜反应；
    (3)先后用蒸馏水和饱和氯化钠溶液充分洗涤步骤(2)所得的物料，再用无水硫酸钠固体干燥过夜；
    (4)通过柱层析对步骤(3)所得的物料进行纯化和洗脱，即可得到无色的固体粗产物；上述洗脱剂为石油醚和乙酸乙酯的混合溶液，
    (5)将步骤(4)所得的固体粗产物用无水乙醇进行重结晶，即得到所述三官能度化合物1,3,5-三(4-甲基丙烯酰氨苯基)苯；
    上述1,3,5-三(4-氨苯基)苯、氯化锂固体、三乙胺、二氯甲烷和甲基丙烯酰氯的比例为2～17重量份:5～15重量份:10～45体积份:45～65体积份:15～55体积份。
  3. 如权利要求2所述的制备方法，其特征在于：所述1,3,5-三(4-氨苯基)苯、氯化锂固体、三乙胺、二氯甲烷和甲基丙烯酰氯的比例为3～15g:5～14g:10～40mL:50～60mL:20～50mL。
  4. 一种用权利要求1所述的三官能度化合物培养晶体的方法，其特征在于：包括如下步骤：
    (1)将所述三官能度化合物溶解于二氯甲烷中，再稀释到装有乙酸乙酯培养容器中；
    (2)将步骤(1)所得的物料放置于严格控温为16℃的恒温培养箱内，保持培养容器敞开，关闭培养箱的门以保证培养箱内的独立环境不受外界条件的干扰，静置至少72h之后，即可长出大量针状和长条状的晶体；
    上述三官能度化合物、二氯甲烷和乙酸乙酯的比例为2～6g:25～65mL:80～250mL。
  5. 如权利要求4所述的方法，其特征在于：所述三官能度化合物、二氯甲烷和乙酸乙酯的比例为2～5g:30～60mL:100～200mL
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