JPS6354345A - （ｓ）−２，３−ジヒドロキシプロピルトリメチルアンモニウムハライドの製造方法 - Google Patents
（ｓ）−２，３−ジヒドロキシプロピルトリメチルアンモニウムハライドの製造方法Info
- Publication number
- JPS6354345A JPS6354345A JP19951286A JP19951286A JPS6354345A JP S6354345 A JPS6354345 A JP S6354345A JP 19951286 A JP19951286 A JP 19951286A JP 19951286 A JP19951286 A JP 19951286A JP S6354345 A JPS6354345 A JP S6354345A
- Authority
- JP
- Japan
- Prior art keywords
- propanediol
- halogeno
- dihydroxypropyltrimethylammonium
- trimethylamine
- halide
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- -1 (s)-2,3-dihydroxypropyl trimethyl ammonium halide Chemical class 0.000 title abstract description 21
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims abstract description 24
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 9
- 230000015572 biosynthetic process Effects 0.000 abstract description 8
- SSZWWUDQMAHNAQ-VKHMYHEASA-N (R)-3-chloro-1,2-propanediol Chemical compound OC[C@@H](O)CCl SSZWWUDQMAHNAQ-VKHMYHEASA-N 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 2
- 244000005700 microbiome Species 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract 2
- SSZWWUDQMAHNAQ-GSVOUGTGSA-N (2s)-3-chloropropane-1,2-diol Chemical compound OC[C@H](O)CCl SSZWWUDQMAHNAQ-GSVOUGTGSA-N 0.000 abstract 1
- 235000014683 Hansenula anomala Nutrition 0.000 abstract 1
- 241000235063 Wickerhamomyces anomalus Species 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YSRQRFIVCMIJJE-RGMNGODLSA-M [(2s)-2,3-dihydroxypropyl]-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)C[C@H](O)CO YSRQRFIVCMIJJE-RGMNGODLSA-M 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- SIBFQOUHOCRXDL-GSVOUGTGSA-N (2s)-3-bromopropane-1,2-diol Chemical compound OC[C@H](O)CBr SIBFQOUHOCRXDL-GSVOUGTGSA-N 0.000 description 1
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000252203 Clupea harengus Species 0.000 description 1
- 241000238557 Decapoda Species 0.000 description 1
- 101100136092 Drosophila melanogaster peng gene Proteins 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000235648 Pichia Species 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 229930003451 Vitamin B1 Natural products 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- 235000019514 herring Nutrition 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
- 239000011691 vitamin B1 Substances 0.000 description 1
- 235000010374 vitamin B1 Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19951286A JPS6354345A (ja) | 1986-08-26 | 1986-08-26 | （ｓ）−２，３−ジヒドロキシプロピルトリメチルアンモニウムハライドの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19951286A JPS6354345A (ja) | 1986-08-26 | 1986-08-26 | （ｓ）−２，３−ジヒドロキシプロピルトリメチルアンモニウムハライドの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6354345A true JPS6354345A (ja) | 1988-03-08 |
| JPH0580465B2 JPH0580465B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-11-09 |
Family
ID=16409051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19951286A Granted JPS6354345A (ja) | 1986-08-26 | 1986-08-26 | （ｓ）−２，３−ジヒドロキシプロピルトリメチルアンモニウムハライドの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6354345A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009526842A (ja) * | 2006-02-15 | 2009-07-23 | ダウ グローバル テクノロジーズ インコーポレイティド | ジヒドロキシトリアルキルアンモニウムハライドを調製するためのプロセス及びその生成物 |
| US8257720B2 (en) | 2009-04-20 | 2012-09-04 | Conopco, Inc. | Stabilized cationic ammonium compounds and compositions comprising the same |
| US8324255B2 (en) | 2009-09-15 | 2012-12-04 | Conopco, Inc. | Chelator stabilized cationic ammonium compounds and compositions comprising the same |
-
1986
- 1986-08-26 JP JP19951286A patent/JPS6354345A/ja active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009526842A (ja) * | 2006-02-15 | 2009-07-23 | ダウ グローバル テクノロジーズ インコーポレイティド | ジヒドロキシトリアルキルアンモニウムハライドを調製するためのプロセス及びその生成物 |
| US8257720B2 (en) | 2009-04-20 | 2012-09-04 | Conopco, Inc. | Stabilized cationic ammonium compounds and compositions comprising the same |
| US8324255B2 (en) | 2009-09-15 | 2012-12-04 | Conopco, Inc. | Chelator stabilized cationic ammonium compounds and compositions comprising the same |
| US8765793B2 (en) | 2009-09-15 | 2014-07-01 | Conopco, Inc. | Compositions with skin benefit compounds and chelator stabilized cationic ammonium compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0580465B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-11-09 |
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