JPS641464B2 - - Google Patents
Info
- Publication number
- JPS641464B2 JPS641464B2 JP1476684A JP1476684A JPS641464B2 JP S641464 B2 JPS641464 B2 JP S641464B2 JP 1476684 A JP1476684 A JP 1476684A JP 1476684 A JP1476684 A JP 1476684A JP S641464 B2 JPS641464 B2 JP S641464B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- salt
- thiuronium
- parts
- general formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 62
- 238000006243 chemical reaction Methods 0.000 claims description 53
- 150000003839 salts Chemical class 0.000 claims description 14
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 238000000354 decomposition reaction Methods 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 9
- 239000011707 mineral Substances 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000000243 solution Substances 0.000 description 27
- 238000000034 method Methods 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 239000012456 homogeneous solution Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- KIUYINLYNRFJLM-UHFFFAOYSA-N chlorothiourea Chemical compound NC(=S)NCl KIUYINLYNRFJLM-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- QEBJRRFIWCWPMA-UHFFFAOYSA-N diethyl-bis(sulfanyl)-$l^{4}-sulfane Chemical compound CCS(S)(S)CC QEBJRRFIWCWPMA-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- MXTOXODEXBYZFX-UHFFFAOYSA-N 2-[2-(2-sulfanylethylsulfanyl)ethylsulfanyl]ethanethiol Chemical compound SCCSCCSCCS MXTOXODEXBYZFX-UHFFFAOYSA-N 0.000 description 2
- YMUJPXAYTKVZGR-UHFFFAOYSA-N 2-[2-(2-sulfanylethylsulfanyl)ethylsulfanyl]ethanol Chemical compound OCCSCCSCCS YMUJPXAYTKVZGR-UHFFFAOYSA-N 0.000 description 2
- VZYIKHZFVOUXKE-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyethylsulfanyl)ethylsulfanyl]ethylsulfanyl]ethanol Chemical compound OCCSCCSCCSCCO VZYIKHZFVOUXKE-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- -1 alkali metal salts Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- YGKHJWTVMIMEPQ-UHFFFAOYSA-N 1,2-propanedithiol Chemical compound CC(S)CS YGKHJWTVMIMEPQ-UHFFFAOYSA-N 0.000 description 1
- BTEAFSPWXRCITQ-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)ethanol Chemical compound OCCSCCS BTEAFSPWXRCITQ-UHFFFAOYSA-N 0.000 description 1
- PDHFSBXFZGYBIP-UHFFFAOYSA-N 2-[2-(2-hydroxyethylsulfanyl)ethylsulfanyl]ethanol Chemical compound OCCSCCSCCO PDHFSBXFZGYBIP-UHFFFAOYSA-N 0.000 description 1
- HKBRNTXNZMVSFI-UHFFFAOYSA-N 2-[2-[2-(2-sulfanylethylsulfanyl)ethylsulfanyl]ethylsulfanyl]ethanol Chemical compound OCCSCCSCCSCCS HKBRNTXNZMVSFI-UHFFFAOYSA-N 0.000 description 1
- OMNOPAUWOXOADS-UHFFFAOYSA-N 2-[2-[2-[2-(2-hydroxyethylsulfanyl)ethylsulfanyl]ethylsulfanyl]ethylsulfanyl]ethanol Chemical compound OCCSCCSCCSCCSCCO OMNOPAUWOXOADS-UHFFFAOYSA-N 0.000 description 1
- QNNVICQPXUUBSN-UHFFFAOYSA-N 2-sulfanylpropan-1-ol Chemical compound CC(S)CO QNNVICQPXUUBSN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001361 allenes Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000009975 flexible effect Effects 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000007867 post-reaction treatment Methods 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- HMPSOEYFMTWOFC-UHFFFAOYSA-N propane-2,2-dithiol Chemical compound CC(C)(S)S HMPSOEYFMTWOFC-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1476684A JPS60158163A (ja) | 1984-01-30 | 1984-01-30 | ポリチオアルキレンジメルカプタン類の製造方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1476684A JPS60158163A (ja) | 1984-01-30 | 1984-01-30 | ポリチオアルキレンジメルカプタン類の製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS60158163A JPS60158163A (ja) | 1985-08-19 |
JPS641464B2 true JPS641464B2 (ko) | 1989-01-11 |
Family
ID=11870193
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP1476684A Granted JPS60158163A (ja) | 1984-01-30 | 1984-01-30 | ポリチオアルキレンジメルカプタン類の製造方法 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS60158163A (ko) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5087758A (en) * | 1988-12-22 | 1992-02-11 | Mitsui Toatsu Chemicals, Inc. | Mercapto compound, a high refractive index resin and lens and a process for preparing them |
JP5358182B2 (ja) * | 2006-04-19 | 2013-12-04 | 三井化学株式会社 | 光学材料用(ポリ)チオール化合物の製造方法およびそれを含む重合性組成物 |
JP6760598B2 (ja) * | 2016-09-30 | 2020-09-23 | ホヤ レンズ タイランド リミテッドHOYA Lens Thailand Ltd | 光学材料用ポリチオール化合物の製造方法 |
-
1984
- 1984-01-30 JP JP1476684A patent/JPS60158163A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS60158163A (ja) | 1985-08-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JPH0321023B2 (ko) | ||
JPS5934181B2 (ja) | メルカプトプロピオン酸エステル及びポリチオジプロピオン酸エステルの製造方法 | |
JPS641464B2 (ko) | ||
JPS641465B2 (ko) | ||
KR950008205B1 (ko) | 3'-아미노프로필 2-설페이토에틸 설폰의 제조방법 | |
JPS5910559A (ja) | ジアルキルトリスルフイド類の製造法 | |
US3397244A (en) | Process for production of diaryl and di (alkaryl) sulfides | |
US4185053A (en) | Process for manufacturing substantially pure dialkyl phosphorochloridothionate | |
JPH0366300B2 (ko) | ||
JP3910232B2 (ja) | メルカプト化合物、トリオール化合物、およびそれらの製造方法 | |
EP1044965B1 (en) | Process for the preparation of aromatic sulfur compounds | |
US4943660A (en) | Process for the production of thiocarbohydrazide | |
JPS6354712B2 (ko) | ||
JPH02172969A (ja) | ジチオールジ(メタ)アクリレートの製造法 | |
US3775484A (en) | Process for preparing metal salts of dithiolbutanediols | |
US2806065A (en) | Manufacture of bis-(b-hydroxyalkyl-) polysulfides | |
US4621139A (en) | Process for the preparation of N-tetrathiodimorpholine | |
JP3794858B2 (ja) | 芳香族硫黄化合物の製造方法 | |
JPS636545B2 (ko) | ||
JPH02145561A (ja) | ポリチオアルキレンジメルカプタン類の製造方法 | |
JP2510089B2 (ja) | メルカプト化エ−テル化合物の製造方法 | |
JPH027950B2 (ko) | ||
JPH01268673A (ja) | メルカプタン化合物の製造方法 | |
JPH11209341A (ja) | メルカプトカルボン酸類の製造方法 | |
SU1286523A1 (ru) | Способ получени коллоидных растворов дисульфида молибдена |