Method for manufacturing diisocyanate and optical lens
Provided is a method for manufacturing diisocyanate and an optical lens in which, during the manufacture of diisocyanate from diamine via diamine hydrochloride, use is made of an aqueous hydrochloric acid solution and an organic solvent instead of hydrogen chloride gas and solid-phase triphosgen instead of phosgen gas while reaction conditions are controlled, whereby the diisocyanate of high quality can be manufactured at excellent yield, with the causation of less environmental problems.
1. A process for preparing metaxylylene diisocyanate, which comprises:
reacting metaxylylenediamine with an aqueous hydrochloric acid solution in a first organic solvent to obtain metaxylylenediamine hydrochloride through a filtration, wherein the first organic solvent is a hydrophilic solvent; and
reacting the metaxylylenediamine hydrochloride with triphosgene in a second organic solvent to obtain metaxylylene diisocyanate,
wherein the reacting metaxylylenediamine with the aqueous hydrochloric acid solution sequentially comprises:
(1a) introducing the aqueous hydrochloric acid solution to a first reactor;
(1b) further introducing the metaxylylenediamine to the first reactor and stirring; and
(1c) further introducing the first organic solvent to the first reactor and stirring,
wherein the yield of the metaxylylene diisocyanate is 80% or more and the purity of the metaxylylene diisocyanate is 95% or more.
2. The process for preparing metaxylylene diisocyanate of claim 1 , wherein the concentration of the aqueous hydrochloric acid solution is 20% by weight to 45% by weight.
3. The process for preparing metaxylylene diisocyanate of claim 1 , wherein the metaxylylenediamine diamine and the aqueous hydrochloric acid solution are introduced to the reaction at an equivalent ratio of 1:2 to 5 at a temperature of 20° C. to 40° C.
4. The process for preparing metaxylylene diisocyanate of claim 1 , wherein the metaxylylenediamine hydrochloride and triphosgene are introduced to the reaction at an equivalent ratio of 1:1 to 5, and the reaction of the metaxylylenediamine hydrochloride with triphosgene is carried out at a temperature of 130° C. to 160° C. for 5 hours to 100 hours.
5. The process for preparing metaxylylene diisocyanate of claim 1 , wherein the first organic solvent is introduced to the reaction in an amount of 1 to 2 times the weight of the metaxylylenediamine, and the second organic solvent is introduced to the reaction in an amount of 3 to 5 times the weight of the metaxylylenediamine hydrochloride.
6. The process for preparing metaxylylene diisocyanate of claim 1 , which further comprises removing the impurities generated in the step of obtaining the metaxylylenediamine hydrochloride together with the first organic solvent.
7. The process for preparing metaxylylene diisocyanate of claim 1 , wherein the reaction of the metaxylylenediamine hydrochloride and triphosgene may sequentially comprise:
(2a) introducing the second organic solvent to a second reactor;
(2b) further introducing the metaxylylenediamine hydrochloride to the second reactor and stirring them; and
(2c) further introducing triphosgene to the second reactor and stirring them.
8. The process for preparing metaxylylene diisocyanate of claim 1 , wherein the metaxylylene diisocyanate is obtained as a result of subjecting the resultant of the reaction of the metaxylylenediamine hydrochloride and the triphosgene to first distillation at 40° C. to 60° C. for 2 to 8 hours and second distillation at 100° C. to 120° C. for 2 to 10 hours.
9. The process for preparing metaxylylene diisocyanate of claim 1 , wherein the step of obtaining metaxylylene diisocyanate from the metaxylylenediamine hydrochloride and triphosgene comprise:
(i) reacting the metaxylylenediamine hydrochloride with triphosgene in a second organic solvent to obtain a reaction solution;
(ii) measuring the color and transparency of the reaction solution; and
(iii) obtaining metaxylylene diisocyanate from the reaction solution.
10. The process for preparing metaxylylene diisocyanate of claim 9 , wherein step (i) and step (ii) are simultaneously carried out, in which the timing for terminating the reaction of the metaxylylenediamine hydrochloride and triphosgene in step (i) is determined according to the color and transparency of the reaction solution measured in step (ii).
11. The process for preparing metaxylylene diisocyanate of claim 10 , wherein the timing for terminating the reaction comes after when the reaction solution turns a transparent light brown color.
12. A process for preparing a diisocyanate, which comprises:
preparing at least one diamine selected from the group consisting of orthoxylylenediamine, metaxylylenediamine, paraxylylenediamine, norbornenediamine, hydrogenated xylylenediamine, and isophoronediamine;
reacting the diamine with an aqueous hydrochloric acid solution in a first organic solvent to obtain a diamine hydrochloride through a filtration, wherein the first organic solvent is a hydrophilic solvent; and
reacting the diamine hydrochloride with triphosgene in a second organic solvent to obtain a diisocyanate,
wherein the reacting the diamine with the aqueous hydrochloric acid solution sequentially comprises:
(1a) introducing the aqueous hydrochloric acid solution to a first reactor;
(1b) further introducing the diamine to the first reactor and stirring; and
(1c) further introducing the first organic solvent to the first reactor and stirring,
wherein the yield of the metaxylylene diisocyanate is 80% or more and the purity of the metaxylylene diisocyanate is 95% or more.
13. The process for preparing a diisocyanate of claim 12 , wherein the diisocyanate is at least one selected from the group consisting of orthoxylylene diisocyanate, metaxylylene diisocyanate, paraxylylene diisocyanate, norbornene diisocyanate, hydrogenated xylylene diisocyanate, and isophorone diisocyanate, and has a purity of 99.5% or more.
14. A process for preparing an optical lens, which comprises:
preparing at least one diamine selected from the group consisting of orthoxylylenediamine, metaxylylenediamine, paraxylylenediamine, norbornenediamine, hydrogenated xylylenediamine, and isophoronediamine;
reacting the diamine with an aqueous hydrochloric acid solution in a first organic solvent to obtain a diamine hydrochloride through a filtration, wherein the first organic solvent is a hydrophilic solvent;
reacting the diamine hydrochloride with triphosgene in a second organic solvent to obtain a diisocyanate; and
mixing the diisocyanate with a thiol or an episulfide and polymerizing and curing the resultant in a mold,
wherein the reacting the diamine with the aqueous hydrochloric acid solution sequentially comprises:
(1a) introducing the aqueous hydrochloric acid solution to a first reactor;
(1b) further introducing the diamine to the first reactor and stirring; and
(1c) further introducing the first organic solvent to the first reactor and stirring,
wherein the yield of the metaxylylene diisocyanate is 80% or more and the purity of the metaxylylene diisocyanate is 95% or more.