Method for producing 1,5-pentanediisocyanate in the gas phase

Patent metadata

Field	Value
Publication number	US-2019112259-A1
Application number	US-201816212994-A
Country	US
Kind code	A1
Filing date	Dec 7, 2018
Priority date	Sep 19, 2014
Publication date	Apr 18, 2019
Grant date	—

Abstract

The invention relates to a method for producing 1,5-pentanediisocyanate (PDI) by reacting 1,5-pentanediamine (PDA) with phosgene in the gas phase.

First claim

1 . A process for preparing pentane 1,5-diisocyanate (PDI) by reacting a stream of pentane-1,5-diamine (PDA) with a stream of phosgene in the gas phase, characterized in that
a) increasing the temperatures both of the phosgene stream and of the pentane-1,5-diamine (PDA) stream prior to entry into the reactor are in the range of 230-320° C. and b) supplying the pentane-1,5-diamine (PDA) stream and the phosgene stream, and an inert gas stream to the reactor by an annular gap nozzle, with the inert gas stream being supplied through the annular gap, c) mixing the pentane-1,5-diamine (PDA) stream, the phosgene stream, and the inert gas stream after entry into the reactor and d) reacting the amine and the phosgene, wherein the sum total of N-carbamoylpiperidine (C6-Im) and N-carbamoyltetrahydropyridines (C6-Az) is <400 ppm based on the weight of the PDI, excluding solvent.

2 . The process for preparing pentane 1,5-diisocyanate (PDI) according to claim 1 , wherein technical grade PDA having a purity of >99% and a water content of <500 ppm is used.

3 . The process for preparing pentane 1,5-diisocyanate (PDI) according to claim 2 , wherein the PDA originates from biobased production.

4 . The process for preparing pentane 1,5-diisocyanate (PDI) according to claim 1 , wherein the temperature of the PDA in a) is in the range from 270° C. to 310° C.

5 . The process for preparing pentane 1,5-diisocyanate (PDI) according to claim 1 , wherein the temperature of the phosgene in a) is in the range from 270° C. to 310° C.

6 . The process for preparing pentane 1,5-diisocyanate (PDI) according to claim 1 , wherein the flow rates of gaseous PGA and phosgene are such that the molar phosgene excess based on one amino group is 30% to 300%.

7 . The process for preparing pentane 1,5-diisocyanate (PDI) according to claim 1 , wherein the annular gap nozzle is formed by a tubular reactor having a twin-wall guide tube arranged centrally in the direction of its axis of rotation, and wherein a concentric annular gap is formed between the inner and outer walls.

8 . The process for preparing pentane 1,5-diisocyanate (PDI) according to claim 1 , wherein the inert gas stream in c) is selected from the group consisting of nitrogen, a noble gas, vapors of an inert solvent or mixtures of these inert gases.

9 . The process for preparing pentane 1,5-diisocyanate (PDI) according to claim 1 , wherein the pressure in an inlet to the reaction space is 200-3000 mbar abs.

10 . The process for preparing pentane 1,5-diisocyanate (PDI) according to claim 1 , wherein the pressure at an outlet from the reaction space is 150-2000 mbar abs.

11 . The process for preparing pentane 1,5-diisocyanate (PDI) according to claim 1 , wherein dwell time in the reactor is 0.1 to 1 seconds.

Assignees

• Covestro Deutschland Ag

Inventors

• Sanders Josef
• Ehrig Martin
• Halpaap Reinhard
• Keller-Killewald Manfred
• Schymura Armin
• Wastian Dietmar

Classifications

• C07C263/10 Primary

  by reaction of amines with carbonyl halides, e.g. with phosgene · CPC title

• C07C265/14

  containing at least two isocyanate groups bound to the same carbon skeleton · CPC title

• B01J2219/00051

  Controlling the temperature · CPC title

• B01J19/1812

  Tubular reactors · CPC title

• B01J2219/00166

  controlling the residence time inside the reactor vessel · CPC title