1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A urethane/urea prepolymer was prepared by reacting 70 percent by weight of a poly(propylene oxide) polyol VORANOL™ 2120 polyol (a trademark of The Dow Chemical Company) with 30 percent by weight of ISONATE™ 50 MDI (a trademark of The Dow Chemical Company; a 50:50 mixture of 4,4'-diisocyanatodiphenylmethane and 2,4'-diisocyanatodiphenylmethane). The following processes were carried out at 10° C. The prepolymer was fed continuously at a rate of 31.4 g/minute through a 1/2-inch (1.25 cm) stainless-steel tube fitted to one arm of a T. A 20-percent aqueous solution of a sodium dodecylbenzene sulfonate (RHODACAL™ DS-10, a trademark of Rhone Poulenc) was fed continuously at a rate of 4.7 g/minute through a 1/8-inch (0.31 cm) stainless-steel tubing fitted to the other arm of the T. The two streams were combined and passed through a static mixer to form a non-emulsified blend. The blend was then fed into a 1/2-inch (1.25 cm) stainless-steel tube fitted to one arm of a T attached to the input of a 70-mL centrifugal pump. Concurrently, water was pumped through a 1/8-inch (0.31 cm) tetrafluoroethylene tubing fitted to the other arm of the T, at the rate of 3.0 g/minute. The two streams were merged and mixed together under shear in the centrifugal pump operating at 650 rpm to form an HIPR emulsion. were carried out at 10° C fitted to one arm of a T fitted to the other arm of the T to form a non-emulsified blend fitted to one arm of a T fitted to the other arm of the T, at the rate of 3.0 g/minute mixed together under shear in the centrifugal pump operating at 650 rpm to form an HIPR emulsion

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.3 g. of an ethyl ester of 2-[(ethoxycarbonyl)-phenylaminomethyl]phenylcarbamic acid (N-benzyl compound), prepared as in Example 1, along with 1.0 g. of 96.4 weight percent concentrated sulfuric acid was charged to a 300 ml reaction flask. The mixture was heated to 100° C. on a constant temperature bath for 60 minutes. High speed liquid chromatographic analysis showed conversion of the ethyl ester of 2-[(ethoxycarbonyl)phenylaminomethyl]phenylcarbamic acid to the diethyl ester of 2,4'-methylenebis(phenylcarbamic) acid and higher homologs to be 99+ percent with minor amounts of ethylphenylcarbamate. After acid extraction with water, the resulting 2,4'-methylenebis(phenylcarbamic) acid, diethyl ester (diurethane) was subjected to thermal decomposition by the method described in U.S. Pat. No. 3,962,302 to produce the diphenylmethane-2,4'-diisocyanate in good yield. After acid extraction with water

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.3 g. of an ethyl ester of 2-[(ethoxycarbonyl)-phenylaminomethyl]phenylcarbamic acid (N-benzyl compound), prepared as in Example 1, along with 1.0 g. of 96.4 weight percent concentrated sulfuric acid was charged to a 300 ml reaction flask. The mixture was heated to 100° C. on a constant temperature bath for 60 minutes. High speed liquid chromatographic analysis showed conversion of the ethyl ester of 2-[(ethoxycarbonyl)phenylaminomethyl]phenylcarbamic acid to the diethyl ester of 2,4'-methylenebis(phenylcarbamic) acid and higher homologs to be 99+ percent with minor amounts of ethylphenylcarbamate. After acid extraction with water, the resulting 2,4'-methylenebis(phenylcarbamic) acid, diethyl ester (diurethane) was subjected to thermal decomposition by the method described in U.S. Pat. No. 3,962,302 to produce the diphenylmethane-2,4'-diisocyanate in good yield. After acid extraction with water

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A urethane/urea prepolymer was prepared by reacting 70 percent by weight of a poly(propylene oxide) polyol VORANOL™ 2120 polyol (a trademark of The Dow Chemical Company) with 30 percent by weight of ISONATE™ 50 MDI (a trademark of The Dow Chemical Company; a 50:50 mixture of 4,4'-diisocyanatodiphenylmethane and 2,4'-diisocyanatodiphenylmethane). The following processes were carried out at 10° C. The prepolymer was fed continuously at a rate of 31.4 g/minute through a 1/2-inch (1.25 cm) stainless-steel tube fitted to one arm of a T. A 20-percent aqueous solution of a sodium dodecylbenzene sulfonate (RHODACAL™ DS-10, a trademark of Rhone Poulenc) was fed continuously at a rate of 4.7 g/minute through a 1/8-inch (0.31 cm) stainless-steel tubing fitted to the other arm of the T. The two streams were combined and passed through a static mixer to form a non-emulsified blend. The blend was then fed into a 1/2-inch (1.25 cm) stainless-steel tube fitted to one arm of a T attached to the input of a 70-mL centrifugal pump. Concurrently, water was pumped through a 1/8-inch (0.31 cm) tetrafluoroethylene tubing fitted to the other arm of the T, at the rate of 3.0 g/minute. The two streams were merged and mixed together under shear in the centrifugal pump operating at 650 rpm to form an HIPR emulsion. were carried out at 10° C fitted to one arm of a T fitted to the other arm of the T to form a non-emulsified blend fitted to one arm of a T fitted to the other arm of the T, at the rate of 3.0 g/minute mixed together under shear in the centrifugal pump operating at 650 rpm to form an HIPR emulsion

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.3 g. of an ethyl ester of 2-[(ethoxycarbonyl)-phenylaminomethyl]phenylcarbamic acid (N-benzyl compound), prepared as in Example 1, along with 1.0 g. of 96.4 weight percent concentrated sulfuric acid was charged to a 300 ml reaction flask. The mixture was heated to 100° C. on a constant temperature bath for 60 minutes. High speed liquid chromatographic analysis showed conversion of the ethyl ester of 2-[(ethoxycarbonyl)phenylaminomethyl]phenylcarbamic acid to the diethyl ester of 2,4'-methylenebis(phenylcarbamic) acid and higher homologs to be 99+ percent with minor amounts of ethylphenylcarbamate. After acid extraction with water, the resulting 2,4'-methylenebis(phenylcarbamic) acid, diethyl ester (diurethane) was subjected to thermal decomposition by the method described in U.S. Pat. No. 3,962,302 to produce the diphenylmethane-2,4'-diisocyanate in good yield. After acid extraction with water