JPS63425B2 - - Google Patents
Info
- Publication number
- JPS63425B2 JPS63425B2 JP56063486A JP6348681A JPS63425B2 JP S63425 B2 JPS63425 B2 JP S63425B2 JP 56063486 A JP56063486 A JP 56063486A JP 6348681 A JP6348681 A JP 6348681A JP S63425 B2 JPS63425 B2 JP S63425B2
- Authority
- JP
- Japan
- Prior art keywords
- chloroalkylamine
- reaction
- hydrochloride
- hydrochlorides
- purity
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 90
- 238000006243 chemical reaction Methods 0.000 claims description 45
- 150000003840 hydrochlorides Chemical class 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- 238000005660 chlorination reaction Methods 0.000 claims description 19
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 19
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 19
- 238000001953 recrystallisation Methods 0.000 claims description 13
- 239000012043 crude product Substances 0.000 claims description 11
- 239000007789 gas Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000012452 mother liquor Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000004064 recycling Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 12
- 239000013078 crystal Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- ONRREFWJTRBDRA-UHFFFAOYSA-N 2-chloroethanamine;hydron;chloride Chemical compound [Cl-].[NH3+]CCCl ONRREFWJTRBDRA-UHFFFAOYSA-N 0.000 description 4
- 239000012320 chlorinating reagent Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 2
- VSBDRUDRPGMLHR-UHFFFAOYSA-N 2-chloropropylazanium;chloride Chemical compound Cl.CC(Cl)CN VSBDRUDRPGMLHR-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000003317 industrial substance Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- FJIWMIJOXISTKW-UHFFFAOYSA-N 1-chloro-N-ethylpropan-2-amine hydrochloride Chemical compound Cl.C(C)NC(CCl)C FJIWMIJOXISTKW-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- SGBGCXQCQVUHNE-UHFFFAOYSA-N 2-(ethylamino)propan-1-ol Chemical compound CCNC(C)CO SGBGCXQCQVUHNE-UHFFFAOYSA-N 0.000 description 1
- JPGZDACJIPHKML-UHFFFAOYSA-N 2-aminopentan-3-ol Chemical compound CCC(O)C(C)N JPGZDACJIPHKML-UHFFFAOYSA-N 0.000 description 1
- LQLJZSJKRYTKTP-UHFFFAOYSA-N 2-dimethylaminoethyl chloride hydrochloride Chemical compound Cl.CN(C)CCCl LQLJZSJKRYTKTP-UHFFFAOYSA-N 0.000 description 1
- PMUNIMVZCACZBB-UHFFFAOYSA-N 2-hydroxyethylazanium;chloride Chemical compound Cl.NCCO PMUNIMVZCACZBB-UHFFFAOYSA-N 0.000 description 1
- XIQMOJPBTZCSDM-UHFFFAOYSA-N 3-(dimethylamino)-2,3-dimethylbutan-2-ol Chemical compound CN(C)C(C)(C)C(C)(C)O XIQMOJPBTZCSDM-UHFFFAOYSA-N 0.000 description 1
- PYSGFFTXMUWEOT-UHFFFAOYSA-N 3-(dimethylamino)propan-1-ol Chemical compound CN(C)CCCO PYSGFFTXMUWEOT-UHFFFAOYSA-N 0.000 description 1
- OVKDLPZRDQTOJW-UHFFFAOYSA-N 3-amino-2-methylbutan-2-ol Chemical compound CC(N)C(C)(C)O OVKDLPZRDQTOJW-UHFFFAOYSA-N 0.000 description 1
- FERWBXLFSBWTDE-UHFFFAOYSA-N 3-aminobutan-2-ol Chemical compound CC(N)C(C)O FERWBXLFSBWTDE-UHFFFAOYSA-N 0.000 description 1
- LJQNMDZRCXJETK-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine;hydron;chloride Chemical compound Cl.CN(C)CCCCl LJQNMDZRCXJETK-UHFFFAOYSA-N 0.000 description 1
- IHPRVZKJZGXTBQ-UHFFFAOYSA-N 3-chloropropan-1-amine;hydron;chloride Chemical compound Cl.NCCCCl IHPRVZKJZGXTBQ-UHFFFAOYSA-N 0.000 description 1
- NTZBBKXYBTYXIC-UHFFFAOYSA-N 4-(dimethylamino)pentan-2-ol Chemical compound CC(O)CC(C)N(C)C NTZBBKXYBTYXIC-UHFFFAOYSA-N 0.000 description 1
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 description 1
- NSDWMQZDGGQRLM-UHFFFAOYSA-N 4-chlorobutan-1-amine;hydrochloride Chemical compound Cl.NCCCCCl NSDWMQZDGGQRLM-UHFFFAOYSA-N 0.000 description 1
- ZCLGFUXQCWNAMT-UHFFFAOYSA-N CC(C)(C(C)(C)Cl)N(C)C.Cl Chemical compound CC(C)(C(C)(C)Cl)N(C)C.Cl ZCLGFUXQCWNAMT-UHFFFAOYSA-N 0.000 description 1
- QTPSYGSRXIMHAH-UHFFFAOYSA-N CC(CC(C)Cl)N(C)C.Cl Chemical compound CC(CC(C)Cl)N(C)C.Cl QTPSYGSRXIMHAH-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- PNYHVDJFKBRIFJ-UHFFFAOYSA-N Cl.C(C)C(C(N)C)Cl Chemical compound Cl.C(C)C(C(N)C)Cl PNYHVDJFKBRIFJ-UHFFFAOYSA-N 0.000 description 1
- ODQDMDWUUUTGCU-UHFFFAOYSA-N Cl.CC(C(N)C)(C)Cl Chemical compound Cl.CC(C(N)C)(C)Cl ODQDMDWUUUTGCU-UHFFFAOYSA-N 0.000 description 1
- UBILXJUTXBOMHE-UHFFFAOYSA-N Cl.CN(CC(C(C)(C)Cl)(C)C)C Chemical compound Cl.CN(CC(C(C)(C)Cl)(C)C)C UBILXJUTXBOMHE-UHFFFAOYSA-N 0.000 description 1
- JSOHZEFFRHOGLB-UHFFFAOYSA-N Cl.NC(C(C)Cl)C Chemical compound Cl.NC(C(C)Cl)C JSOHZEFFRHOGLB-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- -1 amine hydrochloride Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000013077 target material Substances 0.000 description 1
- 238000001291 vacuum drying 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 |
|---|---|---|---|
| JP6348681A JPS57179135A (en) | 1981-04-28 | 1981-04-28 | Preparation of chloroalkylamine hydrochlorides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6348681A JPS57179135A (en) | 1981-04-28 | 1981-04-28 | Preparation of chloroalkylamine hydrochlorides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57179135A JPS57179135A (en) | 1982-11-04 |
| JPS63425B2 true JPS63425B2 (pl) | 1988-01-07 |
Family
ID=13230617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6348681A Granted JPS57179135A (en) | 1981-04-28 | 1981-04-28 | Preparation of chloroalkylamine hydrochlorides |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57179135A (pl) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5841842A (ja) * | 1981-09-07 | 1983-03-11 | Daicel Chem Ind Ltd | Ｎ―置換クロロアルキルアミンの製造法 |
| JPS6245566A (ja) * | 1985-08-21 | 1987-02-27 | Daicel Chem Ind Ltd | Ｎ−アルキル置換クロルアルキルアミン塩酸塩の精製法 |
| CN108164428B (zh) * | 2017-12-29 | 2021-06-18 | 山东泰和水处理科技股份有限公司 | 一种三(2-氯乙基)胺盐酸盐的制备方法 |
| CN108003036B (zh) * | 2017-12-29 | 2020-11-13 | 山东泰和水处理科技股份有限公司 | 一种2-氯乙胺盐酸盐的制备方法 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2136171A (en) * | 1935-01-09 | 1938-11-08 | Ig Farbenindustrie Ag | Manufacture of halogen alkylamines |
| US2212146A (en) * | 1939-03-10 | 1940-08-20 | Du Pont | Preparation of alpha-alkylenimines, e. g., ethylenimine |
| US2617825A (en) * | 1948-06-04 | 1952-11-11 | Givaudan Corp | Process for preparation of salts of 1-amino-2-haloethanes |
| GB693325A (en) * | 1951-05-09 | 1953-06-24 | Saint Gobain | Process for the preparation of hydrochlorides of -a-chlorinated ethylamines |
| JPS50129505A (pl) * | 1974-03-27 | 1975-10-13 |
-
1981
- 1981-04-28 JP JP6348681A patent/JPS57179135A/ja active Granted
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2136171A (en) * | 1935-01-09 | 1938-11-08 | Ig Farbenindustrie Ag | Manufacture of halogen alkylamines |
| US2212146A (en) * | 1939-03-10 | 1940-08-20 | Du Pont | Preparation of alpha-alkylenimines, e. g., ethylenimine |
| US2617825A (en) * | 1948-06-04 | 1952-11-11 | Givaudan Corp | Process for preparation of salts of 1-amino-2-haloethanes |
| GB693325A (en) * | 1951-05-09 | 1953-06-24 | Saint Gobain | Process for the preparation of hydrochlorides of -a-chlorinated ethylamines |
| JPS50129505A (pl) * | 1974-03-27 | 1975-10-13 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57179135A (en) | 1982-11-04 |
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