CN112142966A - 一种聚6-羟基己酸酯的合成方法 - Google Patents
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- IWHLYPDWHHPVAA-UHFFFAOYSA-M 6-hydroxyhexanoate Chemical compound OCCCCCC([O-])=O IWHLYPDWHHPVAA-UHFFFAOYSA-M 0.000 title 1
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- SIJLYRDVTMMSIP-UHFFFAOYSA-N 4-Bromo-1-butanol Chemical compound OCCCCBr SIJLYRDVTMMSIP-UHFFFAOYSA-N 0.000 claims description 2
- HXHGULXINZUGJX-UHFFFAOYSA-N 4-chlorobutanol Chemical compound OCCCCCl HXHGULXINZUGJX-UHFFFAOYSA-N 0.000 claims description 2
- WJVQJXVMLRGNGA-UHFFFAOYSA-N 5-bromopentan-1-ol Chemical compound OCCCCCBr WJVQJXVMLRGNGA-UHFFFAOYSA-N 0.000 claims description 2
- DCBJCKDOZLTTDW-UHFFFAOYSA-N 5-chloropentan-1-ol Chemical compound OCCCCCCl DCBJCKDOZLTTDW-UHFFFAOYSA-N 0.000 claims description 2
- FCMCSZXRVWDVAW-UHFFFAOYSA-N 6-bromo-1-hexanol Chemical compound OCCCCCCBr FCMCSZXRVWDVAW-UHFFFAOYSA-N 0.000 claims description 2
- JNTPTNNCGDAGEJ-UHFFFAOYSA-N 6-chlorohexan-1-ol Chemical compound OCCCCCCCl JNTPTNNCGDAGEJ-UHFFFAOYSA-N 0.000 claims description 2
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- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- BTMVHUNTONAYDX-UHFFFAOYSA-N butyl propionate Chemical compound CCCCOC(=O)CC BTMVHUNTONAYDX-UHFFFAOYSA-N 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 claims description 2
- HKVLOZLUWWLDFP-UHFFFAOYSA-M hydron;tetrabutylazanium;carbonate Chemical compound OC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC HKVLOZLUWWLDFP-UHFFFAOYSA-M 0.000 claims description 2
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 2
- 229960005323 phenoxyethanol Drugs 0.000 claims description 2
- 239000011736 potassium bicarbonate Substances 0.000 claims description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 235000011181 potassium carbonates Nutrition 0.000 claims description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 235000017550 sodium carbonate Nutrition 0.000 claims description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 2
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 claims description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 2
- CEYYIKYYFSTQRU-UHFFFAOYSA-M trimethyl(tetradecyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)C CEYYIKYYFSTQRU-UHFFFAOYSA-M 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract description 4
- 239000000047 product Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 3
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- 238000007086 side reaction Methods 0.000 abstract description 2
- 239000011780 sodium chloride Substances 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 4
- 238000006136 alcoholysis reaction Methods 0.000 description 3
- HYXRUZUPCFVWAH-UHFFFAOYSA-N ethyl 6-hydroxyhexanoate Chemical compound CCOC(=O)CCCCCO HYXRUZUPCFVWAH-UHFFFAOYSA-N 0.000 description 2
- JFKBJGUWDFAOHK-UHFFFAOYSA-N OCCCCCC(=O)O.C=C Chemical compound OCCCCCC(=O)O.C=C JFKBJGUWDFAOHK-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- YDJZXHZRXDLCEH-UHFFFAOYSA-N methyl 6-hydroxyhexanoate Chemical compound COC(=O)CCCCCO YDJZXHZRXDLCEH-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- GFTVKOOSBKTATA-UHFFFAOYSA-N propyl 6-hydroxyhexanoate Chemical compound CCCOC(=O)CCCCCO GFTVKOOSBKTATA-UHFFFAOYSA-N 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
本发明提供了一种聚6‑羟基己酸酯的合成方法，首先将聚6‑羟基己酸用碱中和至中性，然后加入醇、催化剂和一定量的溶剂混合置于反应器中，在50‑150℃温度下带压进行1‑5h的反应，反应结束后，加入带水剂，运用旋转蒸发仪脱去水，得到聚6‑羟基己酸酯。本发明的有益效果是：（1）本技术步骤简单，方法简洁，反应进度快。（2）本技术中无副反应产物生成，且其他产物盐NaCl、KBr、水等易分离且对环境影响小，工艺安全系数高。（3）聚6‑羟基己酸酯的产率在95%以上，生产效果好。
Description
技术领域
本发明属于化工行业，具体涉及一种聚6-羟基己酸酯的合成方法。
背景技术
聚6-羟基己酸酯是一种直链聚酯，非常柔软，具有极大的伸展性，并且有着很好的生物降解性和生物相容性，可作为药物载体和可降解手术缝合线的生产原料，还能和聚乙烯、聚丙烯、聚碳酸酯、聚氯乙烯等高分子互容，共聚制备多种性能优良的共聚物或共混物，是一种非常好用的有机材料。但是目前，关于聚6-羟基己酸酯的合成生产技术资料和文献较少，本课题组之前探究了聚6-羟基己酸醇解反应的工艺条件时，在不同条件下解聚分别得到了6-羟基己酸甲酯、6-羟基己酸乙酯、6-羟基己酸丙酯、6-羟基己酸乙二醇酯、ε-己内酯和低聚物，其中6-羟基己酸乙酯的收率最高，达到87.006％，其他6-羟基己酸酯的产率都不理想，因为聚6-羟基己酸醇解的目标产物是己内酯，6-羟基己酸酯是醇解反应的副产物，这作为一种6-羟基己酸酯的生产工艺是不稳定的，而本工艺聚6-羟基己酸酯的收率均在95％以上，产物成分简单易分离，大大提高了产量和产率。
发明内容
为解决上述问题，本发明提供一项具体实验方案：首先将聚6-羟基己酸用碱中和至中性，然后加入醇、催化剂和一定量的溶剂混合置于反应器中，在50-150℃温度下带压(相应温度水的饱和蒸汽压)进行1-5h的反应，反应结束后，加入带水剂，运用旋转蒸发仪脱去水，得到聚6-羟基己酸酯。
优选的是，醇选自2-溴乙醇、2-氯乙醇、3-氯-1-丙醇、3-溴-1-丙醇、4-溴-1-丁醇、4-氯-1-丁醇、5-氯-1-戊醇、5-溴-1-戊醇、6-溴-1-己醇、6-氯-1-己醇中的一种或几种。
优选的是，醇用量为聚6-羟基己酸的50％-500％。
优选的是，碱选自氢氧化钠、氢氧化钾、氢氧化锂、碳酸氢钠、碳酸氢钾、碳酸钠、碳酸钾中的一种或几种。
优选的是，碱用量为聚6-羟基己酸的50％-200％。
优选的是，碱的浓度均为0.1mol/L。
优选的是，催化剂选自四乙基溴化铵、四丁基溴化铵、四乙基氯化铵、四丁基氯化铵、苄基三乙基氯化铵、四丁基碳酸氢铵、三辛基甲基氯化铵、三丁胺、十二烷基三甲基氯化铵、十四烷基三甲基氯化铵、15-冠醚-5、18-冠醚-6中的一种或几种。
优选的是，催化剂用量的为聚6-羟基己酸质量的0％-8％。
优选的是，溶剂选自DMF、THF、乙二醇单苯醚、甘油、DMSO、乙腈、NMP、甲醇、环己烷、二氯甲烷、丙酮、异丙醇、庚烷、氯仿中的一种或几种，使用量为聚6-羟基己酸的50％-500％。
优选的是，带水剂选自环己烷、二氯甲烷、乙酸乙酯、丙酸乙酯、丙酸正丁酯、甲苯、乙醇、乙醚、苯、正丙醇、异丁醇中的一种或几种。
本发明的有益效果是：
(1)本技术步骤简单，方法简洁，反应进度快。
(2)本技术中无副反应产物生成，且其他产物盐NaCl、KBr、水等易分离且对环境影响小，工艺安全系数高。
(3)聚6-羟基己酸酯的产率在95％以上，生产效果好。
具体实施方式
下面结合实例对本发明进一步描述。但本发明的保护范围不仅限于此。
实施例1
将30g聚6-羟基己酸用0.1mol/L的氢氧化钠溶液中和至中性，然后加入2-氯乙醇30g，在加DMF30g混合置于250ml圆底烧瓶中，在50℃条件下加入四乙基溴化铵0.3g置于集热式恒温加热磁力搅拌仪中通过1h的酯化反应得聚6-羟基己酸酯，然后在得到的聚6-羟基己酸酯中加入20ml环己烷，脱去水得到聚6-羟基己酸酯32.5g，聚6-羟基己酸酯产率98.5％。
实施例2-5
聚6-羟基己酸质量同实施例1，其他与实施例1不同，详见表1。
实施例6-10
聚6-羟基己酸质量为40g，其他与实施例1不同，详见表1。
实施例11-15
聚6-羟基己酸质量为50g，其他与实施例1不同，详见表1。
实施例1-15的实验数据详见表1。
表1实施例实验数据汇总
由表中可以看出，本发明聚6-羟基己酸酯的产率在95％以上，生产效果好。
Claims (10)
1.一种聚6-羟基己酸酯的合成方法，其特征在于，首先将聚6-羟基己酸用碱中和至中性，然后加入醇、催化剂和一定量的溶剂混合，在50-150℃温度下带压进行1-5h的反应，反应结束后，加入带水剂，脱去水，得到聚6-羟基己酸酯。
2.如权利要求1所述一种聚6-羟基己酸酯的合成方法，其特征在于，醇选自2-溴乙醇、2-氯乙醇、3-氯-1-丙醇、3-溴-1-丙醇、4-溴-1-丁醇、4-氯-1-丁醇、5-氯-1-戊醇、5-溴-1-戊醇、6-溴-1-己醇、6-氯-1-己醇中的一种或几种。
3.如权利要求1所述一种聚6-羟基己酸酯的合成方法，其特征在于，醇用量为聚6-羟基己酸的50％-500％。
4.如权利要求1所述一种聚6-羟基己酸酯的合成方法，其特征在于，碱选自氢氧化钠、氢氧化钾、氢氧化锂、碳酸氢钠、碳酸氢钾、碳酸钠、碳酸钾中的一种或几种。
5.如权利要求1所述一种聚6-羟基己酸酯的合成方法，其特征在于，碱用量为聚6-羟基己酸的50％-200％。
6.如权利要求1所述一种聚6-羟基己酸酯的合成方法，其特征在于，碱的浓度均为0.1mol/L。
7.如权利要求1所述一种聚6-羟基己酸酯的合成方法，其特征在于，催化剂选自四乙基溴化铵、四丁基溴化铵、四乙基氯化铵、四丁基氯化铵、苄基三乙基氯化铵、四丁基碳酸氢铵、三辛基甲基氯化铵、三丁胺、十二烷基三甲基氯化铵、十四烷基三甲基氯化铵、15-冠醚-5、18-冠醚-6中的一种或几种。
8.如权利要求1所述一种聚6-羟基己酸酯的合成方法，其特征在于，催化剂用量的为聚6-羟基己酸质量的0％-8％。
9.如权利要求1所述一种聚6-羟基己酸酯的合成方法，其特征在于，溶剂选自DMF、THF、乙二醇单苯醚、甘油、DMSO、乙腈、NMP、甲醇、环己烷、二氯甲烷、丙酮、异丙醇、庚烷、氯仿中的一种或几种，使用量为聚6-羟基己酸的50％-500％。
10.如权利要求1所述一种聚6-羟基己酸酯的合成方法，其特征在于，带水剂选自环己烷、二氯甲烷、乙酸乙酯、丙酸乙酯、丙酸正丁酯、甲苯、乙醇、乙醚、苯、正丙醇、异丁醇中的一种或几种。
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Citations (1)
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| CN1397577A (zh) * | 2002-08-23 | 2003-02-19 | 清华大学 | 一种含有聚－β－羟基丁酸酯嵌段的聚氨酯弹性体的合成 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1397577A (zh) * | 2002-08-23 | 2003-02-19 | 清华大学 | 一种含有聚－β－羟基丁酸酯嵌段的聚氨酯弹性体的合成 |
Non-Patent Citations (1)
| Title |
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| 刘艳等: ""聚6－羟基己酸碱性条件下的水解反应研究"", 《高分子通报》 * |
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