Isothiocyanate production method, composition for transporting and storing N-substituted O-substituted thiocarbamate, and isothiocyanate composition
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.
1. An isothiocyanate composition containing an isothiocyanate at 97 wt % or more based on a total mass of the isothiocyanate composition 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)
2. The isothiocyanate composition according to claim 1 , wherein a total amount of the group represented by formula (1) and formula (2) is at least 0.1 mol ppm and no greater than 1.0×10 4 mol ppm.
3. The isothiocyanate composition according to claim 1 , wherein a total amount of the group represented by formula (1) and formula (2) is at least 0.3 mol ppm and no greater than 5.0×10 3 mol ppm.
4. The isothiocyanate composition according to claim 1 , wherein a total amount of the group represented by formula (1) and formula (2) is at least 0.5 mol ppm and no greater than 3.0×10 3 mol ppm.
5. The isothiocyanate composition according to claim 1 , wherein, when a compound with a thiocarbamate group is present in the isothiocyanate composition, an amount of thiocarbamate group is at least 0.1 mol ppm and no greater than 1.0×10 4 mol ppm with respect to the total amount of isothiocyanate groups in the composition.
6. The isothiocyanate composition according to claim 1 , wherein the isothiocyanate is a compound having none of the groups represented by formulae (1) and (2).
7. The isothiocyanate composition according to claim 1 , wherein the isothiocyanate is a compound represented by the following formula (9):
R 1 NCS) n (9)
wherein R 1 is selected from the group consisting of straight-chain hydrocarbon groups, unsubstituted alicyclic hydrocarbon-derived groups, alkyl-substituted cyclohexane-derived groups, dialkyl-substituted cyclohexane-derived, trialkyl-substituted cyclohexane-derived groups, monoalkyl-substituted benzenes, dialkyl-substituted benzenes, and aromatic hydrocarbon-derived groups, and
n is an integer of 1 to 10.
8. The isothiocyanate composition according to claim 7 , wherein in formula (9), the straight-chain hydrocarbon group is selected from the group consisting of methylene, dimethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene and octamethylene.
9. The isothiocyanate composition according to claim 7 , wherein in formula (9), the unsubstituted alicyclic hydrocarbon-derived group is selected from the group consisting of cyclopentane, cyclohexane, cycloheptane, cyclooctane and bis(cyclohexyl)alkanes.
10. The isothiocyanate composition according to claim 7 , wherein the alkyl-substituted cyclohexane-derived group is selected from the group consisting of methylcyclopentane, ethylcyclopentane, methylcyclohexane and its isomers, ethylcyclohexane and its isomers, propylcyclohexane and its isomers, butylcyclohexane and its isomers, pentylcyclohexane and its isomers and hexylcyclohexane and its isomers.
11. The isothiocyanate composition according to claim 7 , wherein the dialkyl-substituted cyclohexane-derived group is selected from the group consisting of dimethylcyclohexane and its isomers, diethylcyclohexane and its isomers, and dibutylcyclohexane and its isomers.
12. The isothiocyanate composition according to claim 7 , wherein the trialkyl-substituted cyclohexane-derived group is selected from the group consisting of 1,5,5-trimethylcyclohexane, 1,5,5-triethylcyclohexane, 1,5,5-tripropylcyclohexane and its isomers, and 1,5,5-tributylcyclohexane and its isomers.
13. The isothiocyanate composition according to claim 7 , wherein the monoalkyl-substituted benzene is selected from the group consisting of toluene, ethylbenzene and propylbenzene.
14. The isothiocyanate composition according to claim 7 , wherein the dialkyl-substituted benzene is selected from the group consisting of xylene, diethylbenzene and dipropylbenzene.
15. The isothiocyanate composition according to claim 7 , wherein the aromatic hydrocarbon-derived group is selected from the group consisting of diphenylalkanes and benzene.
16. The isothiocyanate composition according to claim 1 , wherein the compound is a compound represented by following formula (18):
wherein R 1 is selected from the group consisting of straight-chain hydrocarbon groups, unsubstituted alicyclic hydrocarbon-derived groups, alkyl-substituted cyclohexane-derived groups, dialkyl-substituted cyclohexane-derived, trialkyl-substituted cyclohexane-derived groups, monoalkyl-substituted benzenes, dialkyl-substituted benzenes, and aromatic hydrocarbon-derived groups,
n is an integer of 1 to 10,
x, y, and z each independently represent an integer of 0 to n, and
n-z-y and n-x-y are both an integer of 0 or greater.
17. The isothiocyanate composition according to claim 16 , wherein the compound represented by formula (18) is a compound represented by the following formula (19):
18. The isothiocyanate composition according to claim 1 , wherein the compound is selected from the group consisting of: