An Improved One-Pot Procedure for Preparation Of N,N -Diethyl-m-Toluamide from m-Toluic Acid
Introduction: Recent statistics have shown that there are hundreds of diseases caused by insects that have a significant impact on human health and they are often fatal. Mosquitoes cause about 10 diseases, most notably malaria, dengue fever and zika fever. N,N-diethyl-m-toluamide (1, DEET) or N,N-di...
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| Format: | Article |
| Language: | Spanish |
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ECIMED
2022-11-01
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| Series: | Revista Cubana de Medicina Militar |
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| Online Access: | https://revmedmilitar.sld.cu/index.php/mil/article/view/2154 |
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| author | Thinh Pham Duc Thu Nguyen Van Phuong Bui Thu Chau Phan Dinh Duc Viet Le Duong Vu Binh |
| author_facet | Thinh Pham Duc Thu Nguyen Van Phuong Bui Thu Chau Phan Dinh Duc Viet Le Duong Vu Binh |
| author_sort | Thinh Pham Duc |
| collection | DOAJ |
| description | Introduction: Recent statistics have shown that there are hundreds of diseases caused by insects that have a significant impact on human health and they are often fatal. Mosquitoes cause about 10 diseases, most notably malaria, dengue fever and zika fever. N,N-diethyl-m-toluamide (1, DEET) or N,N-diethyl-m-methylbenzamide was globally approved under brand names m-Dephene, Detamide, Flypel as one of the most prominent agents for preparation of insect repellants.
Objectives: To present an enhanced method for synthesis of N,N'-diethyl- m-toluamide which can be introduced to industrial scale.
Method: The input materials: m-toluic acid has been activated with thionyl chloride to create the intermediate product, m-toluoyl chloride. This product then was reacted with diethylamine in order to produce DEET. This method has been improved the factors affecting the synthesis of DEET.
Results: DEET was successfully synthesized using well known materials with high efficiency and purity. During research all the by-products and waste materials in the reaction are highly water-soluble, therefore the final product was obtained at pharmaceutical requirement without further purification. The analytical data has shown that DEET was collected at a very high yield in the range of 96-98%, purity (HPLC): 95.5-97.6%. The structure of DEET was determined by model spectroscopies MS, and NMR.
Conclusions: An improved procedure for the synthesis of N,N-diethyl-m -toluamide (DEET) or N,N-diethyl-m-methylbenzamide is established where the use of all reagents was optimized in suitable amount to apply in industrial production. |
| format | Article |
| id | doaj-art-d42ba7b6530d479ea66963dea6cc407c |
| institution | Kabale University |
| issn | 1561-3046 |
| language | Spanish |
| publishDate | 2022-11-01 |
| publisher | ECIMED |
| record_format | Article |
| series | Revista Cubana de Medicina Militar |
| spelling | doaj-art-d42ba7b6530d479ea66963dea6cc407c2025-01-10T19:04:24ZspaECIMEDRevista Cubana de Medicina Militar1561-30462022-11-01514644An Improved One-Pot Procedure for Preparation Of N,N -Diethyl-m-Toluamide from m-Toluic AcidThinh Pham Duc0https://orcid.org/0000-0002-5853-764XThu Nguyen Van1https://orcid.org/0000-0002-4836-3359Phuong Bui Thu2https://orcid.org/0000-0003-2706-3952Chau Phan Dinh3https://orcid.org/0000-0002-4232-7023Duc Viet Le4https://orcid.org/0000-0002-6517-4218Duong Vu Binh5https://orcid.org/0000-0002-1055-3181Vietnam Military Medical UniversityVietnam Military Medical UniversityVietnam Military Medical UniversitySchool of Chemical Engineering, Hanoi University of Science and TechnologyMilitary institute of drug, medical equipment quality control and researchVietnam Military Medical UniversityIntroduction: Recent statistics have shown that there are hundreds of diseases caused by insects that have a significant impact on human health and they are often fatal. Mosquitoes cause about 10 diseases, most notably malaria, dengue fever and zika fever. N,N-diethyl-m-toluamide (1, DEET) or N,N-diethyl-m-methylbenzamide was globally approved under brand names m-Dephene, Detamide, Flypel as one of the most prominent agents for preparation of insect repellants. Objectives: To present an enhanced method for synthesis of N,N'-diethyl- m-toluamide which can be introduced to industrial scale. Method: The input materials: m-toluic acid has been activated with thionyl chloride to create the intermediate product, m-toluoyl chloride. This product then was reacted with diethylamine in order to produce DEET. This method has been improved the factors affecting the synthesis of DEET. Results: DEET was successfully synthesized using well known materials with high efficiency and purity. During research all the by-products and waste materials in the reaction are highly water-soluble, therefore the final product was obtained at pharmaceutical requirement without further purification. The analytical data has shown that DEET was collected at a very high yield in the range of 96-98%, purity (HPLC): 95.5-97.6%. The structure of DEET was determined by model spectroscopies MS, and NMR. Conclusions: An improved procedure for the synthesis of N,N-diethyl-m -toluamide (DEET) or N,N-diethyl-m-methylbenzamide is established where the use of all reagents was optimized in suitable amount to apply in industrial production.https://revmedmilitar.sld.cu/index.php/mil/article/view/2154m-toluic acidNN-diethyl-m-toluamideingredientinsects repellent. |
| spellingShingle | Thinh Pham Duc Thu Nguyen Van Phuong Bui Thu Chau Phan Dinh Duc Viet Le Duong Vu Binh An Improved One-Pot Procedure for Preparation Of N,N -Diethyl-m-Toluamide from m-Toluic Acid Revista Cubana de Medicina Militar m-toluic acid N N-diethyl-m-toluamide ingredient insects repellent. |
| title | An Improved One-Pot Procedure for Preparation Of N,N -Diethyl-m-Toluamide from m-Toluic Acid |
| title_full | An Improved One-Pot Procedure for Preparation Of N,N -Diethyl-m-Toluamide from m-Toluic Acid |
| title_fullStr | An Improved One-Pot Procedure for Preparation Of N,N -Diethyl-m-Toluamide from m-Toluic Acid |
| title_full_unstemmed | An Improved One-Pot Procedure for Preparation Of N,N -Diethyl-m-Toluamide from m-Toluic Acid |
| title_short | An Improved One-Pot Procedure for Preparation Of N,N -Diethyl-m-Toluamide from m-Toluic Acid |
| title_sort | improved one pot procedure for preparation of n n diethyl m toluamide from m toluic acid |
| topic | m-toluic acid N N-diethyl-m-toluamide ingredient insects repellent. |
| url | https://revmedmilitar.sld.cu/index.php/mil/article/view/2154 |
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