CN108530272A - 一种4,7,10,13,16-五氧杂-1,18-十九烷二炔化合物 - Google Patents

一种4,7,10,13,16-五氧杂-1,18-十九烷二炔化合物 Download PDF

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CN108530272A
CN108530272A CN201810239277.8A CN201810239277A CN108530272A CN 108530272 A CN108530272 A CN 108530272A CN 201810239277 A CN201810239277 A CN 201810239277A CN 108530272 A CN108530272 A CN 108530272A
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nonadecane
oxa
diines
dialkynes
reaction
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闫峥峰
汪营磊
丁峰
高福磊
潘永飞
陈斌
陆婷婷
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Xian Modern Chemistry Research Institute
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Xian Modern Chemistry Research Institute
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B45/00—Compositions or products which are defined by structure or arrangement of component of product
    • C06B45/04—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive
    • C06B45/06—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive the solid solution or matrix containing an organic component
    • C06B45/10—Compositions or products which are defined by structure or arrangement of component of product comprising solid particles dispersed in solid solution or matrix not used for explosives where the matrix consists essentially of nitrated carbohydrates or a low molecular organic explosive the solid solution or matrix containing an organic component the organic component containing a resin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers

Abstract

本发明公开了一种4,7,10,13,16‑五氧杂‑1,18‑十九烷二炔化合物，其结构如下：

Description

一种4,7,10,13,16-五氧杂-1,18-十九烷二炔化合物
技术领域
本发明涉及一种4,7,10,13,16-五氧杂-1,18-十九烷二炔化合物，作为双炔基固化剂，属于推进剂应用技术领域。
背景技术
丁二酸二丙炔醇酯是一种良好的固化剂，用之取代异氰酸酯类固化剂固化聚叠氮缩水甘油醚、聚3,3-二叠氮甲基氧杂环丁烷等叠氮类粘合剂，避免了异氰酸酯对环境敏感，难以实现宽环境条件下的产品制造和与绿色高能材料二硝酰胺铵、CL-20不相容的缺陷。2014年，甘宁等人(甘宁、李娜、莫宏昌等，ATP/BPS交联体合成及性能研究，固体火箭技术[J]，2014 37(5):658-661.)报道合成出的丁二酸二丙炔醇酯是一凝固点略高于室温的白色晶体(凝固点34℃～35℃)，直接使用时分散性不佳，在配方中难以均匀分散，故使用前需加热融化，取用不便。
发明内容
本发明要解决的技术问题是针对现有技术的不足，提供一种室温下为液体的4,7,10,13,16-五氧杂-1,18-十九烷二炔，可作为含叠氮基粘合剂的固化剂。
本发明采用的技术方案是提供一种4,7,10,13,16-五氧杂-1,18-十九烷二炔，它具有如下结构：
该4,7,10,13,16-五氧杂-1,18-十九烷二炔制备方法包括如下步骤：
(1)按质量比将1份聚乙二醇200、0.5份氢氧化钠搅拌溶解于3.8份乙腈中，加热至回流；
(2)缓慢将1.5份溴丙炔滴加于反应液中，回流反应9h；
(3)过滤除去反应液中的固体，浓缩除去溶剂及低沸点的原料；
(4)在浓缩液中加入4份四氢呋喃，使用饱和氯化钠溶液2份*3次洗涤后浓缩，柱层析(石油醚：乙酸乙酯＝2:1)，得黄色液体为4,7,10,13,16-五氧杂-1,18-十九烷二炔。
本发明适用于含有叠氮基的粘合剂的固化。
本发明与现有技术相比的优点：
本发明制备的一种4,7,10,13,16-五氧杂-1,18-十九烷二炔，-5℃至室温下为液体，取用方便，在推进剂配方中分散均匀，而现有技术的丁二酸二丙炔醇酯凝固点34℃～35℃，分散性不佳。
具体实施方式
实施例1 4,7,10,13,16-五氧杂-1,18-十九烷二炔的制备
三口烧瓶中加入磁子，装回流冷凝管、温度计和加料漏斗。先加入聚乙二醇20019.4g，氢氧化钠9.6g，乙腈50mL，搅拌加热至回流后，缓慢滴加28.5g溴丙炔，继续反应9h。停止反应后，过滤除去反应残渣，悬蒸除去溶剂和低沸点杂质，再加入40mL四氢呋喃，使用饱和氯化钠溶液20份*3次洗涤后浓缩，柱层析(石油醚：乙酸乙酯＝2:1)，得黄色液体为4,7,10,13,16-五氧杂-1,18-十九烷二炔。
产物的核磁氢谱(d6-丙酮，500MHz)：4.05(d,4H)3.49(m,8H)3.67(s,4H)2.80(t,2H)。其中σ＝4.05、2.80分别为炔丙基的特征峰，3.49是主链的各个氢的特征峰，各峰归属与化合物吻合，证明所得的化合物为4,7,10,13,16-五氧杂-1,18-十九烷二炔。将4,7-二氧杂-1,9-癸烷二炔置于-5℃冰箱中冷藏24h，产物仍为液体。
实施例2 4,7,10,13,16-五氧杂-1,18-十九烷二炔
三口烧瓶中加入磁子，装回流冷凝管、温度计和加料漏斗。先加入聚乙二醇20019.4g，氢氧化钠8.8g，乙腈50mL，搅拌加热至回流后，缓慢滴加26.2g溴丙炔，继续反应9h。停止反应后，过滤除去反应残渣，悬蒸除去溶剂和低沸点杂质，再加入40mL四氢呋喃，使用饱和氯化钠溶液20份*3次洗涤后浓缩，柱层析(石油醚：乙酸乙酯＝2:1)，得黄色液体为4,7,10,13,16-五氧杂-1,18-十九烷二炔。将4,7-二氧杂-1,9-癸烷二炔置于-5℃冰箱中冷藏24h，产物仍为液体。

Claims (1)

1.一种4,7,10,13,16-五氧杂-1,18-十九烷二炔化合物，其结构式如式(Ⅰ)所示：
CN201810239277.8A 2018-03-22 2018-03-22 一种4,7,10,13,16-五氧杂-1,18-十九烷二炔化合物 Pending CN108530272A (zh)

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Citations (3)

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Patent Citations (3)

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Publication number Priority date Publication date Assignee Title
US20020155443A1 (en) * 2000-01-25 2002-10-24 Kerwin Sean M. Metal binding DNA interactive compounds
CN101306354A (zh) * 2007-05-17 2008-11-19 华东理工大学 一种环糊精手性色谱固定相及其制备方法
CN102256989A (zh) * 2008-10-03 2011-11-23 聚糖生物科学私人有限公司 糖基化细菌代谢物的阴离子轭合物

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