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Azobisisobutyronitrile → Hydroxynaphthalene Methacrylate

HRID 350593
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HRID 350593 반응식
[C:1]([O:6][C:7]1[C:16]2[C:11](=[C:12](O)[CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3].C(OC(C(F)(F)F)C(F)(F)F)(=O)C(C)=C.C(C1CCOC1=O)(=O)C(C)=C.N(C(C)(C)C#N)=NC(C)(C)C#N>CCCCCC.C(OC(=O)C)C.O1CCCC1>[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].[OH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 6547AzobisisobutyronitrileHCID 764691,1,1,3,3,3-Hexafluoro-2-propyl methacrylateHCID 219037765-Hydroxy-1-naphthalenyl methacrylateHCID 224927382-Methacryloyl-gamma-butyrolactone

생성물 1

HCID 67312192Hydroxynaphthalene Methacrylate수율 90%

시약·촉매·용매 3

HCID 8028
Tetrahydrofuran
용매
HCID 8058Hexane용매
HCID 8857Ethyl Acetate용매

실험 절차

5-hydroxy-1-naphthalenyl methacrylate (a.k.a. hydroxynaphthalene methacrylate or NAMA) monomer (2.60 g, 0.0045 mole), hexafluoroisopropyl methacrylate (iPrHFAMA) monomer (23.20 g, 0.0800 mole), 2-methacryloyl-gamma-butyrolactone (a.k.a. gamma-butyrolactone methacrylate or GBLMA) monomer (3.88 g, 0.0051 mole), azobisisobutyronitrile (AlBN) (0.91 g, 10% the total mole of all monomers), 150 g of tetrahydrofuran (THF) and 72 g of ethylacetate were added to a 250 ml 3-neck round bottom flask equipped with condenser, thermometer, nitrogen inlet and magnetic stirrer bar. The reaction mixture was stirred at room temperature and bubbled with N2 flow for 45 minutes after which is was heated to 67–70° C. and stirred for 14 hours with a blanket N2 flow. After reaction, the solution was then cooled to room temperature and added dropwise to 1200 g of hexane. The resulting slurry was stirred for two hours before filtration. Solid was air dried on the Buckner filter for 1.5 hours, dissolved in acetone (15% wt-wt) and reprecipitated in 1200 g of hexane. The slurry was again stirred for two hours before filtration. The solid was collected and air dried for 2–3 hours before final drying in a vacuum oven at 60° C. overnight. Yield: 90%.

후처리

  1. customequipped with condenser
  2. custombubbled with N2 flow for 45 minutes after which
  3. temperatureis was heated to 67–70° C.
  4. stirringstirred for 14 hours with a blanket N2 flow
  5. customAfter reaction
  6. temperaturethe solution was then cooled to room temperature
  7. stirringThe resulting slurry was stirred for two hours before filtration
  8. customdried on the Buckner
  9. filtrationfilter for 1.5 hours
  10. dissolutiondissolved in acetone (15% wt-wt)
  11. customreprecipitated in 1200 g of hexane
  12. stirringThe slurry was again stirred for two hours before filtration
  13. customThe solid was collected
  14. customair dried for 2–3 hours
  15. custombefore final drying in a vacuum oven at 60° C. overnight

출처 및 근거

ORD 기록
ord-4b1a085b588e46ee9c9cb2242aa40b39
출처 데이터셋
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07183036B2

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