CN113620907A - 一种吗啉季铵盐及其制备方法和应用 - Google Patents
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- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 title claims abstract description 40
- -1 Morpholine quaternary ammonium salt Chemical class 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 239000002781 deodorant agent Substances 0.000 claims abstract description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 5
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001450 anions Chemical class 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- 239000000047 product Substances 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 claims description 7
- 229940008406 diethyl sulfate Drugs 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- 239000013067 intermediate product Substances 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 4
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000003899 bactericide agent Substances 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 3
- 238000005956 quaternization reaction Methods 0.000 abstract description 3
- 229960000686 benzalkonium chloride Drugs 0.000 abstract description 2
- XIWFQDBQMCDYJT-UHFFFAOYSA-M benzyl-dimethyl-tridecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 XIWFQDBQMCDYJT-UHFFFAOYSA-M 0.000 abstract description 2
- 230000001877 deodorizing effect Effects 0.000 abstract description 2
- 230000001988 toxicity Effects 0.000 abstract description 2
- 231100000419 toxicity Toxicity 0.000 abstract description 2
- 230000001954 sterilising effect Effects 0.000 description 11
- 238000004659 sterilization and disinfection Methods 0.000 description 10
- 238000004332 deodorization Methods 0.000 description 5
- 241000282326 Felis catus Species 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 3
- 230000007794 irritation Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000001953 sensory effect Effects 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 1
- KOFZTCSTGIWCQG-UHFFFAOYSA-N 1-bromotetradecane Chemical compound CCCCCCCCCCCCCCBr KOFZTCSTGIWCQG-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000001149 cognitive effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 239000010842 industrial wastewater Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L9/00—Disinfection, sterilisation or deodorisation of air
- A61L9/01—Deodorant compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2101/00—Chemical composition of materials used in disinfecting, sterilising or deodorising
- A61L2101/32—Organic compounds
- A61L2101/44—Heterocyclic compounds
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- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
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- Plant Pathology (AREA)
- Epidemiology (AREA)
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Abstract
本发明提供一种吗啉季铵盐及其制备方法和应用，分子结构通式为：
通式中X为以下阴离子中的一种：Cl、Br、I、C2H5SO4；通式中R为10‑14个碳原子的饱和碳链。本发明所述的吗啉季铵盐是基于吗啉用于除臭应用的基础上对其结构的改性，使其季铵化，保留了其除臭的作用同时使其具有类似苯扎氯铵的杀菌作用达到两个功能相结合的作用。同时季铵化后改善了吗啉作为除臭剂的生理毒性，使其不具有挥发性。
Description
技术领域
本发明涉及一种新型季铵盐的合成，具体为一种吗啉季铵盐及其制备方法和应用。
技术背景
传统的兼顾杀菌和除臭的化学物质通常为强氧化剂，如次氯酸，双氧水等。但由于其对人体皮肤拥有较强的刺激性，通常用于工业废水、垃圾等处理，对于家庭使用并不是很好的解决方案。然而市面上兼顾杀菌除臭现有的产品通常为复合制剂，通常为对人体刺激性较小的单双链季铵盐以及香精复配，达到杀菌以及改善气味的作用，然而并没有真正的将异味分子捕捉。
因此需要一款真正意义上能够捕捉异味分子且兼顾杀菌性能，且对人体刺激性小的杀菌除味剂。
发明内容
为了克服现有技术缺陷，本发明所要解决的技术问题是，提供一种吗啉季铵盐及其制备方法。该吗啉季铵盐具有工艺简单，不挥发，热稳定性好，使用浓度低，具有良好的杀菌和除臭功能等特点。
具体的技术方案为：
一种吗啉季铵盐，分子结构通式为：
通式中X为以下阴离子中的一种：Cl、Br、I、C2H5SO4；
通式中R为10-14个碳原子的饱和碳链。
一种吗啉季铵盐的制备方法为：
S1.在纯水中加入吗啉、溴代十二烷、TBAOH、NaOH，100℃搅拌回流过夜；
待反应结束后加入适量盐酸中和至中性，加入乙酸乙酯萃取2-3次，保留水相，旋干后得到中间产物；
S2.将上述中间产物和硫酸二乙酯加入四氢呋喃中，100℃搅拌回流过夜；
待反应结束后旋干溶剂即得目标产物。
各个步骤中物质的用量按照以下比例配比：
S1中，10mL纯水、吗啉3-4g、长链卤代烃10-15g、TBAOH 50uL、NaOH 2-3g；
S2.中，中间产物1-2g、硫酸二乙酯1-2g、四氢呋喃5mL。
本发明获得的吗啉季铵盐的应用，作为除臭剂和/或杀菌剂。
本发明的有益效果是：
本发明所述的吗啉季铵盐是基于吗啉用于除臭应用的基础上对其结构的改性，使其季铵化。保留了其除臭的作用同时使其具有类似苯扎氯铵的杀菌作用达到两个功能相结合的作用。同时季铵化后改善了吗啉作为除臭剂的生理毒性，使其不具有挥发性。
具体实施方式
结合实施例说明本发明的具体技术方案。
实施例一：
1.在10mL纯水中加入吗啉：3.5g、溴代癸烷：10.0g、TBAOH：50uL、NaOH：2.4g，100℃搅拌回流过夜。待反应结束后加入适量盐酸中和至中性，加入乙酸乙酯萃取2-3次，保留水相，旋干后即的目标产物。
2.将上述产物0.98g和硫酸二乙酯0.71g加入5mL四氢呋喃中100℃搅拌回流过夜。待反应结束后旋干溶剂即得目标产物。
实施例二：
1.在10mL纯水中加入吗啉：3.5g、溴代十二烷：11.2g、TBAOH：50uL、NaOH：2.2g，100℃搅拌回流过夜。待反应结束后加入适量盐酸中和至中性，加入乙酸乙酯萃取2-3次，保留水相，旋干后即的目标产物。
2.将上述产物0.98g和硫酸二乙酯0.71g加入5mL四氢呋喃中100℃搅拌回流过夜。待反应结束后旋干溶剂即得目标产物。
实施例三：
1.在10mL纯水中加入吗啉：3.5g、溴代十四烷：12.5g、TBAOH：50uL、NaOH：2.3g，100℃搅拌回流过夜。待反应结束后加入适量盐酸中和至中性，加入乙酸乙酯萃取2-3次，保留水相，旋干后即的目标产物。
2.将上述产物0.98g和硫酸二乙酯0.71g加入5mL四氢呋喃中100℃搅拌回流过夜。待反应结束后旋干溶剂即得目标产物。
杀菌实验：参考《消毒技术规范》2002年版2.1.8抗(抑)菌试验对上述三个实施例进行杀菌实验，作用浓度0.1％，作用时间1min。结果见表1.
表1杀菌实验结果
| 实施例一 | 实施例二 | 实施例三 |
| >99.999％ | >99.999％ | >99.999％ |
除臭实验：
取猫粪猫尿作为臭源，按下表2进行感官评估.
表2感官评估标准
| 恶臭强烈级别 | 嗅觉对臭气的反应 |
| 0 | 无臭味 |
| 1 | 勉强可以感觉到臭味(检测阈值) |
| 2 | 容易感到轻微臭味(认知阈值) |
| 3 | 明显感到臭味 |
| 4 | 强烈臭味 |
| 5 | 无法忍受的极强臭味 |
取上述三个实施例最终产物兑水稀释成0.2％浓度水溶液，将猫粪猫尿取适量涂于10cm培养皿中，各喷涂2次，取喷涂后不同时间评估打分，结果如下表3。
表3感官评估结果
以上所述实施例仅表达了本发明的几种实施方式，其描述较为具体和详细，但并不能因此而理解为对发明专利范围的限制。应当指出的是，对于本领域的普通技术人员来说，在不脱离本发明构思的前提下，还可以做出若干变形和改进，这些都属于本发明的保护范围。因此，本发明专利的保护范围应以所附权利要求为准。
Claims (4)
1.一种吗啉季铵盐，其特征在于，分子结构通式为：
通式中X为以下阴离子中的一种：Cl、Br、I、C2H5SO4；
通式中R为10-14个碳原子的饱和碳链。
2.根据权利要求1所述的一种吗啉季铵盐的制备方法，其特征在于，包括以下步骤：
S1.在纯水中加入吗啉、溴代十二烷、TBAOH、NaOH，100℃搅拌回流过夜；
待反应结束后加入适量盐酸中和至中性，加入乙酸乙酯萃取2-3次，保留水相，旋干后得到中间产物；
S2.将上述中间产物和硫酸二乙酯加入四氢呋喃中，100℃搅拌回流过夜；
待反应结束后旋干溶剂即得目标产物。
3.根据权利要求2所述的一种吗啉季铵盐的制备方法，其特征在于，
各个步骤中物质的用量按照以下比例配比：
S1中，10mL纯水、吗啉3-4g、长链卤代烃10-15g、TBAOH 50uL、NaOH 2-3g；
S2.中，中间产物1-2g、硫酸二乙酯1-2g、四氢呋喃5mL。
4.根据权利要求1所述的一种吗啉季铵盐的应用，其特征在于，作为除臭剂或杀菌剂。
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