Synthesis, Characterization, and Performance Evaluation of Sulfur-Containing Diphenylamines Based on Intramolecular Synergism
To obtain novel structural antioxidants that have different antioxidant mechanisms, four 2-(alkylthio)-N-(4-(phenylamino)phenyl)acetamides 2a–d as dual functional antioxidants are designed, synthesized, and confirmed by 1H-NMR, FTIR, MS, and elemental analysis. The antioxidant behavior of compounds...
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2018-02-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | http://www.mdpi.com/1420-3049/23/2/401 |
| _version_ | 1819267461217779712 |
|---|---|
| author | Jun-Bo He Hao Shi Yue Wang Xin-Lei Gao |
| author_facet | Jun-Bo He Hao Shi Yue Wang Xin-Lei Gao |
| author_sort | Jun-Bo He |
| collection | DOAJ |
| description | To obtain novel structural antioxidants that have different antioxidant mechanisms, four 2-(alkylthio)-N-(4-(phenylamino)phenyl)acetamides 2a–d as dual functional antioxidants are designed, synthesized, and confirmed by 1H-NMR, FTIR, MS, and elemental analysis. The antioxidant behavior of compounds 2a–d as additives of base oil triisodecyl trimellitate (TIDTM) is evaluated by non-isothermal and isothermal DSC analyses. The results showed all compounds can greatly increase the incipient oxidation temperature (IOT) and oxidation induction time (OIT) of TIDTM, especially, compound 2c exhibited an OIT value of 72.5 min at 230 °C, which is almost 28 times the length of TIDTM. Moreover, compounds 2a–d do not affect the tribological performance of TIDTM. The mechanism of antioxidants involved an intramolecular synergism are proposed. This work demonstrates compound 2c can be used as a novel potential antioxidant additive of TIDTM; in addition, it would inspire the emergence of highly potent antioxidants with different antioxidant mechanisms. |
| first_indexed | 2024-12-23T21:17:32Z |
| format | Article |
| id | doaj.art-38112f50f72c4c6d93cb8fe10dbc0eaf |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-23T21:17:32Z |
| publishDate | 2018-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-38112f50f72c4c6d93cb8fe10dbc0eaf2022-12-21T17:30:51ZengMDPI AGMolecules1420-30492018-02-0123240110.3390/molecules23020401molecules23020401Synthesis, Characterization, and Performance Evaluation of Sulfur-Containing Diphenylamines Based on Intramolecular SynergismJun-Bo He0Hao Shi1Yue Wang2Xin-Lei Gao3Key Laboratory for Deep Processing of Major Grain and Oil, Ministry of Education, College of Food Science & Engineering, Wuhan Polytechnic University, Wuhan 430023, ChinaKey Laboratory for Deep Processing of Major Grain and Oil, Ministry of Education, College of Food Science & Engineering, Wuhan Polytechnic University, Wuhan 430023, ChinaDepartment of Chemical and Environmental Engineering, Wuhan Polytechnic University, Wuhan 430023, ChinaDepartment of Chemical and Environmental Engineering, Wuhan Polytechnic University, Wuhan 430023, ChinaTo obtain novel structural antioxidants that have different antioxidant mechanisms, four 2-(alkylthio)-N-(4-(phenylamino)phenyl)acetamides 2a–d as dual functional antioxidants are designed, synthesized, and confirmed by 1H-NMR, FTIR, MS, and elemental analysis. The antioxidant behavior of compounds 2a–d as additives of base oil triisodecyl trimellitate (TIDTM) is evaluated by non-isothermal and isothermal DSC analyses. The results showed all compounds can greatly increase the incipient oxidation temperature (IOT) and oxidation induction time (OIT) of TIDTM, especially, compound 2c exhibited an OIT value of 72.5 min at 230 °C, which is almost 28 times the length of TIDTM. Moreover, compounds 2a–d do not affect the tribological performance of TIDTM. The mechanism of antioxidants involved an intramolecular synergism are proposed. This work demonstrates compound 2c can be used as a novel potential antioxidant additive of TIDTM; in addition, it would inspire the emergence of highly potent antioxidants with different antioxidant mechanisms.http://www.mdpi.com/1420-3049/23/2/401sulfur-containing 4-aminodiphenylaminedual functional antioxidantsantioxidant mechanismintramolecular synergism |
| spellingShingle | Jun-Bo He Hao Shi Yue Wang Xin-Lei Gao Synthesis, Characterization, and Performance Evaluation of Sulfur-Containing Diphenylamines Based on Intramolecular Synergism Molecules sulfur-containing 4-aminodiphenylamine dual functional antioxidants antioxidant mechanism intramolecular synergism |
| title | Synthesis, Characterization, and Performance Evaluation of Sulfur-Containing Diphenylamines Based on Intramolecular Synergism |
| title_full | Synthesis, Characterization, and Performance Evaluation of Sulfur-Containing Diphenylamines Based on Intramolecular Synergism |
| title_fullStr | Synthesis, Characterization, and Performance Evaluation of Sulfur-Containing Diphenylamines Based on Intramolecular Synergism |
| title_full_unstemmed | Synthesis, Characterization, and Performance Evaluation of Sulfur-Containing Diphenylamines Based on Intramolecular Synergism |
| title_short | Synthesis, Characterization, and Performance Evaluation of Sulfur-Containing Diphenylamines Based on Intramolecular Synergism |
| title_sort | synthesis characterization and performance evaluation of sulfur containing diphenylamines based on intramolecular synergism |
| topic | sulfur-containing 4-aminodiphenylamine dual functional antioxidants antioxidant mechanism intramolecular synergism |
| url | http://www.mdpi.com/1420-3049/23/2/401 |
| work_keys_str_mv | AT junbohe synthesischaracterizationandperformanceevaluationofsulfurcontainingdiphenylaminesbasedonintramolecularsynergism AT haoshi synthesischaracterizationandperformanceevaluationofsulfurcontainingdiphenylaminesbasedonintramolecularsynergism AT yuewang synthesischaracterizationandperformanceevaluationofsulfurcontainingdiphenylaminesbasedonintramolecularsynergism AT xinleigao synthesischaracterizationandperformanceevaluationofsulfurcontainingdiphenylaminesbasedonintramolecularsynergism |