Adipic Acid → Methacrylic Acid

HRID 1826241Notes

Reaction equation

HRID 1826241 reaction equation
N[CH2:2]CNCCN.[C:8](O)(=O)[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].[OH2:18]>>[CH3:2][O:18][C:10]1[CH:9]=[CH:8][C:13]([OH:15])=[CH:12][CH:11]=1.[C:13]([OH:15])(=[O:14])[C:12]([CH3:2])=[CH2:11]

Participants

5

Reactant 3

HCID 196Adipic AcidHCID 962Water10×HCID 8111Diethylenetriamine

Product 2

HCID 4093Methacrylic AcidHCID 90154-Methoxyphenol

Conditions

Temperature
150 °C

Procedure

A cylindrical reaction vessel equipped with a thermometer, stirrer, water separator and cooling pipe (condenser) was charged with 6,000 parts of diethylenetriamine, 7,309 parts of adipic acid, and the mixture was stirred and blended in a nitrogen atmosphere. The cock portion of the water separator was charged with 2 parts of methoquinone as an antigelling agent. The reaction vessel had an outside diameter of 30 cm (heated on an oil bath), a height of 50 cm and a capacity (A) of 0.03 m3 and had a structure such that a connecting pipe having an inside diameter of about 2 cm could be connected thereto at a site 10 cm distant from the central axis of the reaction vessel. The condenser used was a commercially available glass-made Dimroth condenser (condenser pipe length 40 cm; product of Shibata Kagaku Kikai Kogyo). The byproduct water separator and connecting pipe used was a commercially available volumetric water receptacle (capacity 25 ml, equipped with a cock; product of Shibata Kagaku Kikai Kogyo). With this water separator, when the cock is closed, the amount of the byproduct water can be read from marked lines provided on the side glass face, so that it functions also as a level gauge. Thus, the amount of the byproduct water can be checked by reading the marked line indicating the liquid level and, upon arrival of the level at the maximum value-indicating marked line, the byproduct water can be discharged out of the system by turning on the bottom cock; thereafter, the amount of the byproduct water newly formed can be read. The reaction mixture was heated to 150° C. and the reaction was conducted for 20 hours while removing the byproduct water formed by the polycondensation, to give 11,332 parts of a polycondensate (the byproduct water amounting to 1,977 parts) Then, 17 parts of hydroquinone methyl ether and 701 parts of methacrylic acid were charged into the vessel and the amidation reaction was carried out at a reaction temperature of 150° C. As a result of 10 hours of amidation reaction, 160 parts of byproduct water was separated in the byproduct water separator to give 11,890 parts of an amidation product (M9), namely a polyamide polyamine. During the reaction, methacrylic acid contained in the byproduct water would not gelate but the cock could be turned on from time to time to discharge the water; the amount of the byproduct water thus could be monitored.

Workup

  1. temperaturecooling pipe (condenser)
  2. temperaturean outside diameter of 30 cm (heated on an oil bath)
  3. customequipped with a cock
  4. customprovided on the side glass face, so that it
  5. customwhile removing the byproduct water
  6. customformed by the polycondensation

Sources & evidence

ORD record
ord-1f5de04404e24eb3975df1a68eff7f7d
Source dataset
uspto-grants-2006_05
Patent number
US07049462B2

Reaction notes

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