Isothiocyanate production method, composition for transporting and storing n-substituted o-substituted thiocarbamate, and isothiocyanate composition

Patent metadata

Field	Value
Publication number	US-2016016901-A1
Application number	US-201414772943-A
Country	US
Kind code	A1
Filing date	Feb 28, 2014
Priority date	Mar 5, 2013
Publication date	Jan 21, 2016
Grant date	—

Abstract

The present invention relates to an isothiocyanate production method using an organic primary amine and thiourea as starting materials; to a composition for transporting and storing an N-substituted O-substituted thiocarbamate that includes an N-substituted O-substituted thiocarbamate and a hydroxy compound, the equivalent weight ratio of hydroxy groups of the hydroxy compound with respect to the carbamate groups of the N-substituted O-substituted thiocarbamate being in the range of 1 to 100; to a composition for transporting and storing a compound with a thioureido group that includes a compound with a thioureido group and a hydroxy compound, the equivalent weight ratio of hydroxy groups of the hydroxy compound with respect to the thioureido groups of the compound with a thioureido group being in the range of 1 to 100; and to an isothiocyanate composition containing an isothiocyanate and a compound with a specific functional group.

First claim

1 . A method for producing an isothiocyanate using an organic primary amine and thiourea as starting materials.

2 . The method according to claim 1 , comprising:
a step (1) of producing a compound with a thioureido group and ammonia by reacting the organic primary amine and the thiourea; and a step (2) of thermally decomposing the compound with a thioureido group and then separating an isothiocyanate and ammonia generated.

3 . The method according to claim 1 , comprising a step (I) of reacting the organic primary amine and the thiourea and then separating an isothiocyanate and ammonia generated.

4 . The method according to claim 1 , comprising:
a step (A) of producing a compound with a thioureido group and ammonia by reacting the organic primary amine and the thiourea; a step (B) of separating ammonia after producing an N-substituted O-substituted thiocarbamate and ammonia by reacting the compound with a thioureido group and a hydroxy compound; and a step (C) of producing an isothiocyanate by thermally decomposing the N-substituted O-substituted thiocarbamate.

5 . The method according to claim 1 , comprising:
a step (a) of separating ammonia after producing an N-substituted O-substituted thiocarbamate and ammonia by reacting the organic primary amine, the thiourea and a hydroxy compound; and a step (b) of producing an isothiocyanate by thermally decomposing the N-substituted O-substituted thiocarbamate.

6 . The method according to claim 2 , including a step (X) of separating the compound with a thioureido group and the ammonia, further performed simultaneously with the step (1) and/or after the step (1).

7 . The method according to claim 4 , including a step (X) of separating the compound with a thioureido group and the ammonia, further performed simultaneously with the step (A) and/or after the step (A).

8 . The method according to claim 4 , wherein a step (Y) is performed in the step (B), the step (Y) comprising:
separating as a gas phase component all or a portion of the hydroxy compound and all or a portion of the compound with a thiocarbonyl group excluding the N-substituted O-substituted thiocarbamate, along with the ammonia; and condensing the hydroxy compound and the compound with a thiocarbonyl group by introducing the gas phase component including the ammonia, the hydroxy compound and the compound with a thiocarbonyl group into a condenser, using the gas phase component.

9 . The method according to claim 5 , wherein a step (Y) is performed in the step (a), the step (Y) comprising:
separating as a gas phase component all or a portion of the hydroxy compound and all or a portion of the compound with a thiocarbonyl group excluding the N-substituted O-substituted thiocarbamate, along with the ammonia; and condensing the hydroxy compound and the compound with a thiocarbonyl group by introducing the gas phase component including the ammonia, the hydroxy compound and the compound with a thiocarbonyl group into a condenser, using the gas phase component.

10 . The method according to claim 8 , wherein a ratio (H/T) of an amount (H) of the hydroxy compound to be condensed with respect to an amount (T) of the compound with a thiocarbonyl group to be condensed in the step (Y), is 1 or greater.

11 . The method according to claim 10 , wherein a ratio of the number of thiocarbonyl groups with respect to the number of ammonia molecules in the gaseous mixture that has not been condensed in the step (Y) is 1 or smaller.

12 .- 15 . (canceled)

16 . A composition for transporting and storing a compound with a thioureido group, comprising:
a compound with a thioureido group and a hydroxy compound, wherein an equivalent weight ratio of hydroxy groups of the hydroxy compound with respect to thioureido groups of the compound with a thioureido group is in the range of 1 to 100.

17 . The composition according to claim 16 , further comprising at least one type of compound selected from the group consisting of thiourea, N-unsubstituted O-substituted thiocarbamates, thiocarbonic acid esters, dithiobiuret and dithiobiuret derivatives.

18 . An isothiocyanate composition containing an isothiocyanate and a compound having at least one type of functional group selected from the group consisting of groups represented by the following formula (1) and formula (2).

Assignees

• Asahi Kasei Chemicals Corp

Inventors

• Shinohata Masaaki
• Kosugi Yuji
• Miyake Nobuhisa

Classifications

• C07C335/16

  having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton · CPC title

• C07C333/06

  having nitrogen atoms of thiocarbamic groups bound to carbon atoms of rings other than six-membered aromatic rings · CPC title

• C07C333/04

  having nitrogen atoms of thiocarbamic groups bound to hydrogen atoms or to acyclic carbon atoms · CPC title

• C07C331/20

  of a saturated carbon skeleton · CPC title

• C07C335/08

  of a saturated carbon skeleton · CPC title