Adipic Acid → Styrene

HRID 2166962Notes

Reaction equation

HRID 2166962 reaction equation
[CH2:1](O)[CH:2]([OH:4])[CH3:3].[C:6](O)(=O)[CH2:7][CH2:8][CH2:9][CH2:10]C(O)=O.C1(C=CC(O)=CC=1)O.CC1C(N=C=O)=CC([N:31]=[C:32]=[O:33])=CC=1.C(OCCO)(=O)C=C.C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC>C=CC1C=CC=CC=1>[CH2:3]=[CH:2][C:1]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[NH2:31][C:32]([O:4][CH2:2][CH3:3])=[O:33]

Participants

9

Reactant 6

HCID 196Adipic AcidHCID 785HydroquinoneHCID 1030Propylene GlycolHCID 11443Toluene 2,4-DiisocyanateHCID 131652-Hydroxyethyl acrylateHCID 9809426Di-n-butyldilauryltin

Product 2

HCID 5641Carbamic acid, ethyl esterHCID 7501StyreneYield 50%

Reagents, catalysts & solvents 1

HCID 7501StyreneSolvent

Procedure

300 ppm of hydroquinone were added to an unsaturated polyester having an acid number of 35 and prepared from 665 g (4 moles) of isophthalic acid, 588 g (6 moles) of maleic anhydride and 798 g (10.5 moles) of propylene glycol in the conventional two-stage reaction. The resulting product was then dissolved in styrene to obtain an unsaturated polyester resin having an unvolatile content of 60% (hereinafter referred to as Polyester A). Apart from this resin, a hydroxyl polyester having an acid number of 0.2 and a hydroxyl number of 54 (hereinafter termed Polyester B) was prepared from 874 g (11.5 moles) of propylene glycol and 1460 g (10 moles) of adipic acid. 2080 g (hydroxyl equivalent: 2) of Polyester B were dissolved in 2457 g of styrene and 0.74 g of hydroquinone with the application of heat. To the obtained solution were added dropwise at a controlled temperature not exceeding 60° C. over one hour 261 g (isocyanate equivalent: 3) of tolylene diisocyanate (manufactured by Nippon Polyurethane Kogyo Kabushiki Kaisha under the name of DESMODULE T-80). Subsequently, the reaction was allowed to continue for one further hour. To the reaction product were then added dropwise for 30 minutes a mixture of 116 g (1 mole) of hydroxyethyl acrylate and 0.49 g of dibutyltin dilaurate. Subsequently, the reaction was allowed to continue at 70° C. for 2.5 hours, and terminated after no absorption of infrared rays by NCO was observed in the vicinity of 2270 cm-1 with an infrared spectrometer, thereby to obtain a 50% styrene solution of an unsaturated acrylic urethane having a weight-average extension of molecular chain of 550 A (hereinafter called Acrylic Urethane C).

Workup

  1. additionTo the obtained solution were added dropwise at a controlled temperature not
  2. additionTo the reaction product were then added dropwise for 30 minutes
  3. waitto continue at 70° C. for 2.5 hours
  4. customterminated
  5. customafter no absorption of infrared rays by NCO

Sources & evidence

ORD record
ord-4fb2d1a541c74f3395713507b9c77811
Source dataset
uspto-grants-1983_06
Patent number
US04390662

Reaction notes

Loading…