Methacrylic Acid → 4-[(2-Methylacryloyl)amino]benzoic acid

HRID 657458Notes

Reaction equation

HRID 657458 reaction equation
CO[CH2:3][NH:4][C:5](=[O:9])[C:6]([CH3:8])=[CH2:7].C([O:15][CH2:16][C:17]1[CH:22]=[CH:21]C=[CH:19][CH:18]=1)(=O)C(C)=C.C(O)(=[O:27])C(C)=C.C(S)CCCCCCCCCCC.CC(N=NC(C#N)(C)C)(C#N)C.COCNC(=O)C(C)=C.C(OCC1C=CC=CC=1)(=O)C(C)=C.C(O)(=O)C(C)=C>COCCO>[C:16]([C:17]1[CH:22]=[CH:21][C:3]([NH:4][C:5](=[O:9])[C:6]([CH3:8])=[CH2:7])=[CH:19][CH:18]=1)([OH:15])=[O:27]

Participants

8

Reactant 6

HCID 4093Methacrylic Acid2×HCID 6547Azobisisobutyronitrile3×HCID 81951-Dodecanethiol2×HCID 17236Benzyl methacrylate2×HCID 772042-Propenamide, N-(methoxymethyl)-2-methyl-2×HCID 131729318HCID 131729318, compound

Product 1

HCID 98590994-[(2-Methylacryloyl)amino]benzoic acid

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
80 °C

Procedure

Methyl cellosolve (199.8 g), N-methoxymethyl methacrylamide (18 g), benzyl methacrylate (11.4 g), methacrylic acid (3 g), dodecyl mercaptan (0.075 g), and Vazo-64 (0.6 g) were added to 500 ml 4-neck ground glass flask, equipped with a heating mantle, temperature controller, mechanical stirrer, condenser, pressure equalized addition funnel and nitrogen inlet. The reaction mixture was heated to 80° C. under nitrogen atmosphere. Then, a pre-mixture of N-methoxymethyl methacrylamide (55 g), benzyl methacrylate (34 g), methacrylic acid (9 g), dodecyl mercaptan (0.225 g), and Vazo-64 (1.2 g) were added over two hours at 80° C. The reaction was continued another eight hours and Vazo 64 (0.35 g) was added two more times. The polymer conversion was >99% based on determination of percent of non-volatiles. The weight ratio of N-methoxymethyl methacrylamide/benzyl methacrylate/methacrylic acid in the polymer was 56/34.8/9.2. The resin solution was precipitated in powder form using DI water/Ice (3:1) and a Lab Dispersator (4000 RPM) and then filtered. The resulting powder was dried at room temperature for 24 hours. The next day, a tray containing the polymer was placed in oven at 110° F. (43° C.) for two additional days. The yield was 95% and polymer acid number was 58 (actual) versus 58.8 (theoretical).

Workup

  1. customequipped with a heating mantle, temperature controller, mechanical stirrer, condenser, pressure
  2. additionaddition funnel and nitrogen inlet
  3. additionwere added over two hours at 80° C
  4. customThe resin solution was precipitated in powder form
  5. filtrationa Lab Dispersator (4000 RPM) and then filtered
  6. customThe resulting powder was dried at room temperature for 24 hours
  7. additionThe next day, a tray containing the polymer
  8. customwas placed in oven at 110° F.
  9. custom(43° C.)

Sources & evidence

ORD record
ord-c14bdaeb89a147918a763d81c3c07300
Source dataset
uspto-grants-2011_12
Patent number
US08076052B2

Reaction notes

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