tert-Butyl hydroperoxide → N-(3-(Dimethylamino)propyl)methacrylamide

HRID 1844285

反応式

HRID 1844285 の反応式
CC(C1C=C[CH:7]=[C:6]([C:10]([N:13]=[C:14]=[O:15])(C)C)C=1)=C.[C:16](=O)([O-])[NH2:17].[C:20](=S)([O-])N.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].[C:33](OO)(C)([CH3:35])[CH3:34]>C(N1CCCC1=O)=C.CN(CCCC=C(C)C(N)=O)C.O.[NH4+].[NH4+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[Fe+2].CC(O)C>[CH3:35][C:33]([C:14]([NH:13][CH2:10][CH2:6][CH2:7][N:17]([CH3:16])[CH3:20])=[O:15])=[CH2:34]

参加物

10

反応物 4

HCID 6410tert-Butyl hydroperoxideHCID 6041521-(1-Isocyanato-1-methylethyl)-3-(1-methylethenyl)benzene2 回HCID 656671Sodium PyrosulfiteHCID 178514126Carbamate thiocarbamate2 回

生成物 1

HCID 78882N-(3-(Dimethylamino)propyl)methacrylamide

試薬・触媒・溶媒 5

HCID 24863Ferrous ammonium sulfate触媒HCID 962Water溶媒3 回HCID 3776Isopropanol溶媒HCID 6917N-vinyl-2-pyrrolidone溶媒2 回HCID 20976834HCID 20976834、化合物溶媒2 回

反応条件

温度
65 °C

実験手順

The polymerization of N-vinyl-2-pyrrolidone (VP), dimethylaminopropyl methacrylamide (DMAPMA), and m-TMI-ME carbamate-thiocarbamate (produced in Example 1) in 82:17:1 molar ratio involved the following steps: A 0.5-L, four-neck reaction kettle was equipped with a nitrogen purge, a condenser, a mechanical stirrer, and an oil bath. A monomer solution was prepared by dissolving 5.0 g of m-TMI-ME carbamate-thiocarbamate (from Example 1) in 76.0 g of N-vinyl-2-pyrrolidone and 19.0 g of DMAPMA. Then, 160.0 g of 2-propanol (IPA) was added to the reaction vessel, stirring was started, the vessel was purged with nitrogen and heated to 65° C. over the course of 1 hour. At t=0, 0.2 g of the initiator tert-butylperoxypivalate (Trigonox® 25-C75, Akzo Nobel) dissolved in 10.0 g of IPA were charged into the reaction kettle. Simultaneously, the monomer solution was fed to the kettle, and was completed in the course of 1 hour. At t=1 hour, 0.2 g of the initiator was dissolved in 10.0 g of IPA and added to the reaction kettle, which was held for 1 hour. At t=2 hours, 0.2 g of the initiator was dissolved in 10.0 g of IPA and added to the reaction kettle, which was held for 2 hours. At t=4 hours, 0.4 g of the initiator was dissolved in 10.0 g of IPA and added to the reaction kettle, which was held for 2 hours. Then, starting at t=6 hours, 0.1 g of the intiator dissolved in 1.0 g of IPA was added to the reactor and held for 1 hour. This step was repeated 6 times. Afterward, at t=12 hours, the solvent was exchanged with 200.0 g of deionized water, completed over 1 hour. Simultaneously, three redox system initiator solutions were prepared. Solution A contained 0.01 g of ferrous ammonium sulfate dissolved in 99.99 g of deionized water. Solution B contained 2.52 g of sodium metabisulfite dissolved in 36 g of deionized water. Solution C contained 3.78 g of tert-butyl hydroperoxide 70 (Brand name, manufacturer) dissolved in 18.0 g of deionized water. From t=13 to 24 hours, a charge of 12.0 g of Solution A was added over 10 seconds and then reaction conditions held for 10 minutes. Then, 6.42 g of Solution B were added over 10 seconds, and held for 10 minutes. Finally, 3.63 g of Solution C were added over 10 seconds. At t=24 hours the reaction was stopped and the contents of the kettle were discharged.

後処理

  1. customwas equipped with a nitrogen
  2. custompurge
  3. customA monomer solution was prepared
  4. customthe vessel was purged with nitrogen
  5. dissolutionAt t=0, 0.2 g of the initiator tert-butylperoxypivalate (Trigonox® 25-C75, Akzo Nobel) dissolved in 10.0 g of IPA
  6. additionwere charged into the reaction kettle
  7. customwas completed in the course of 1 hour
  8. dissolutionAt t=1 hour, 0.2 g of the initiator was dissolved in 10.0 g of IPA
  9. additionadded to the reaction kettle, which
  10. dissolutionAt t=2 hours, 0.2 g of the initiator was dissolved in 10.0 g of IPA
  11. additionadded to the reaction kettle, which
  12. waitwas held for 2 hours
  13. dissolutionAt t=4 hours, 0.4 g of the initiator was dissolved in 10.0 g of IPA
  14. additionadded to the reaction kettle, which
  15. waitwas held for 2 hours
  16. customstarting at t=6 hours, 0.1 g of the intiator
  17. dissolutiondissolved in 1.0 g of IPA
  18. additionwas added to the reactor
  19. waitheld for 1 hour
  20. customat t=12 hours
  21. waitcompleted over 1 hour
  22. customSimultaneously, three redox system initiator solutions were prepared
  23. additionwas added over 10 seconds
  24. customreaction conditions
  25. waitheld for 10 minutes
  26. waitheld for 10 minutes
  27. customAt t=24 hours

出典と根拠

ORDレコード
ord-317db86859104f3581b5d7c1a24481d0
出典データセット
uspto-grants-2015_02
特許番号
US08946367B2

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