Ammonia → HCID 21966223, compound

Temperature

110 °C

Subsequently, 150.0 parts by weight of a 17.3% aqueous solution of sodium sulfide was added dropwise over 5.5 hours at 7° C. to 37° C., and the mixture was stirred for 120 minutes. Production of a tetraol compound of formula (4) was confirmed from NMR data. 279.0 parts by weight of 35.5% hydrochloric acid was introduced, and then 125.8 parts by weight of thiourea having a purity of 99.90% was introduced. The mixture was stirred for 3 hours under reflux at 110° C., and thereby a reaction which forms thiuronium salt was carried out. The reaction mixture was cooled to 45° C., and then 214.0 parts by weight of toluene was added thereto, and the mixture was cooled to 26° C. 206.2 parts by weight of a 25 wt % aqueous ammonia solution was introduced over 30 minutes at 26° C. to 50° C., and a hydrolytic reaction was carried out by stirring the mixture for 1 hour at 50° C. to 65° C. Thus, a toluene solution of a polythiol compound containing 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, and 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane as main components was obtained. 59.4 parts by weight of 36% hydrochloric acid was added to the toluene solution, and acid washing for 30 minutes at 34° C. to 39° C. was performed two times. 118.7 parts by weight of degassed water (dissolved oxygen concentration: 2 ppm) was added, and washing for 30 minutes at 35° C. to 45° C. was performed five times. Toluene and a trace amount of water were removed under heating at reduced pressure, and then the residue was filtered under reduced pressure using a 1.2 μm PTFE type membrane filter, and thus 115.9 parts by weight of a polythiol compound containing 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane (hereinafter, compound A), 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane (hereinafter, compound B), and 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane (hereinafter, compound C) as main components was obtained (isomeric mixture of compounds A/B/C=85/5/10 (molar ratio)). The properties of the polythiol compound thus obtained are shown in Table-1.

1. additionwas introduced
2. stirringThe mixture was stirred for 3 hours
3. customa reaction which
4. temperatureThe reaction mixture was cooled to 45° C.
5. temperaturethe mixture was cooled to 26° C
6. customa hydrolytic reaction
7. stirringby stirring the mixture for 1 hour at 50° C. to 65° C
8. customwas obtained
9. washwashing for 30 minutes at 34° C. to 39° C.
10. addition118.7 parts by weight of degassed water (dissolved oxygen concentration: 2 ppm) was added
11. washwashing for 30 minutes at 35° C. to 45° C.
12. customToluene and a trace amount of water were removed
13. temperatureunder heating at reduced pressure
14. filtrationthe residue was filtered under reduced pressure
15. filtrationfilter
16. additionthus 115.9 parts by weight of a polythiol compound containing 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane (hereinafter, compound A), 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane (hereinafter, compound B), and 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane (hereinafter, compound C) as main components
17. customwas obtained (
18. additionisomeric mixture of compounds A/B/C=85/5/10 (molar ratio))
19. customThe properties of the polythiol compound thus obtained

ORD record

ord-b6004dcb40b5449593eb02710556900c

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181180B2