JPH0238586B2 - - Google Patents
Info
- Publication number
- JPH0238586B2 JPH0238586B2 JP56109214A JP10921481A JPH0238586B2 JP H0238586 B2 JPH0238586 B2 JP H0238586B2 JP 56109214 A JP56109214 A JP 56109214A JP 10921481 A JP10921481 A JP 10921481A JP H0238586 B2 JPH0238586 B2 JP H0238586B2
- Authority
- JP
- Japan
- Prior art keywords
- bis
- disulfide
- aminoethanethiol
- hydrohalides
- aminoethyl
- 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 - Lifetime
Links
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 claims description 31
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- APQPRKLAWCIJEK-UHFFFAOYSA-N cystamine Chemical compound NCCSSCCN APQPRKLAWCIJEK-UHFFFAOYSA-N 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical class O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000012046 mixed solvent Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000013078 crystal Substances 0.000 description 48
- 239000002904 solvent Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- -1 alkylene imines Chemical class 0.000 description 17
- 239000012452 mother liquor Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- YUFRRMZSSPQMOS-UHFFFAOYSA-N 2-(2-aminoethyldisulfanyl)ethanamine;hydron;dichloride Chemical compound Cl.Cl.NCCSSCCN YUFRRMZSSPQMOS-UHFFFAOYSA-N 0.000 description 8
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 8
- 239000012535 impurity Substances 0.000 description 6
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- NHPZYACMJUGKNI-UHFFFAOYSA-N 2-(2-aminoethyldisulfanyl)ethanamine;dihydrobromide Chemical compound Br.Br.NCCSSCCN NHPZYACMJUGKNI-UHFFFAOYSA-N 0.000 description 4
- HPFRRTFGBNMTDH-UHFFFAOYSA-N 2-aminoethanethiol;hydrobromide Chemical compound Br.NCCS HPFRRTFGBNMTDH-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- HCZBCEYVAPRCDV-UHFFFAOYSA-N 2-sulfanylpropylazanium;chloride Chemical compound Cl.CC(S)CN HCZBCEYVAPRCDV-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FVMYCGRNEHXKCC-UHFFFAOYSA-N 1-(2-aminopropyldisulfanyl)propan-2-amine Chemical compound CC(N)CSSCC(C)N FVMYCGRNEHXKCC-UHFFFAOYSA-N 0.000 description 1
- PENUHZFHDGZEAP-UHFFFAOYSA-N 1-aminobutane-2-thiol Chemical compound CCC(S)CN PENUHZFHDGZEAP-UHFFFAOYSA-N 0.000 description 1
- ZQXIMYREBUZLPM-UHFFFAOYSA-N 1-aminoethanethiol Chemical compound CC(N)S ZQXIMYREBUZLPM-UHFFFAOYSA-N 0.000 description 1
- GNETVHIDZPYGGD-UHFFFAOYSA-N 1-aminoethanethiol;hydrochloride Chemical group Cl.CC(N)S GNETVHIDZPYGGD-UHFFFAOYSA-N 0.000 description 1
- MHJPNBAEWSRKBK-UHFFFAOYSA-N 1-aminopropane-2-thiol Chemical compound CC(S)CN MHJPNBAEWSRKBK-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- DRJXRYDPRUIAQD-UHFFFAOYSA-N 2-(1-aminopropan-2-yldisulfanyl)propan-1-amine Chemical compound NCC(C)SSC(C)CN DRJXRYDPRUIAQD-UHFFFAOYSA-N 0.000 description 1
- INIBQWPBYCXUQZ-UHFFFAOYSA-N 2-amino-2-ethylbutane-1-thiol Chemical compound CCC(N)(CC)CS INIBQWPBYCXUQZ-UHFFFAOYSA-N 0.000 description 1
- WHFJUXYUXQYZSH-UHFFFAOYSA-N 2-amino-2-methylpropane-1-thiol Chemical compound CC(C)(N)CS WHFJUXYUXQYZSH-UHFFFAOYSA-N 0.000 description 1
- SBFLJHLQNAYTIS-UHFFFAOYSA-N 2-aminobutane-1-thiol Chemical compound CCC(N)CS SBFLJHLQNAYTIS-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- DJJIBYYAHJOUMY-UHFFFAOYSA-N 2-aminopropane-1-thiol Chemical compound CC(N)CS DJJIBYYAHJOUMY-UHFFFAOYSA-N 0.000 description 1
- GHGJMMAWDARQSF-UHFFFAOYSA-N 3-(aminomethyl)pentane-3-thiol Chemical compound CCC(S)(CC)CN GHGJMMAWDARQSF-UHFFFAOYSA-N 0.000 description 1
- XNBYJQNYVIYRRV-UHFFFAOYSA-N 3-amino-2-methylbutane-2-thiol Chemical compound CC(N)C(C)(C)S XNBYJQNYVIYRRV-UHFFFAOYSA-N 0.000 description 1
- XNMFUOBRLLJWJV-UHFFFAOYSA-N 3-aminobutane-2-thiol Chemical compound CC(N)C(C)S XNMFUOBRLLJWJV-UHFFFAOYSA-N 0.000 description 1
- AJWVDGABWLKIGT-UHFFFAOYSA-N 3-methylpentane-3-thiol Chemical compound CCC(C)(S)CC AJWVDGABWLKIGT-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UCPGYYKRVOOSMT-UHFFFAOYSA-N NCC(C)(C)SSC(C)(C)CN Chemical compound NCC(C)(C)SSC(C)(C)CN UCPGYYKRVOOSMT-UHFFFAOYSA-N 0.000 description 1
- GJPCTAKRQZKVCR-UHFFFAOYSA-N [Cl-].C(C)(C)[SH2+] Chemical compound [Cl-].C(C)(C)[SH2+] GJPCTAKRQZKVCR-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003549 thiazolines Chemical class 0.000 description 1
- 238000004448 titration Methods 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 |
|---|---|---|---|
| JP10921481A JPS5813563A (ja) | 1981-07-15 | 1981-07-15 | ２−アミノエタンチオ−ルハロゲン化水素酸塩類の精製分離方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10921481A JPS5813563A (ja) | 1981-07-15 | 1981-07-15 | ２−アミノエタンチオ−ルハロゲン化水素酸塩類の精製分離方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5813563A JPS5813563A (ja) | 1983-01-26 |
| JPH0238586B2 true JPH0238586B2 (pl) | 1990-08-31 |
Family
ID=14504483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10921481A Granted JPS5813563A (ja) | 1981-07-15 | 1981-07-15 | ２−アミノエタンチオ−ルハロゲン化水素酸塩類の精製分離方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5813563A (pl) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5661350A (en) * | 1979-10-25 | 1981-05-26 | Seitetsu Kagaku Co Ltd | Preparation of cysteamine hydrochloride |
-
1981
- 1981-07-15 JP JP10921481A patent/JPS5813563A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5661350A (en) * | 1979-10-25 | 1981-05-26 | Seitetsu Kagaku Co Ltd | Preparation of cysteamine hydrochloride |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5813563A (ja) | 1983-01-26 |
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