JP4306192B2 - グリシン誘導体の製造方法 - Google Patents
グリシン誘導体の製造方法 Download PDFInfo
- Publication number
- JP4306192B2 JP4306192B2 JP2002190861A JP2002190861A JP4306192B2 JP 4306192 B2 JP4306192 B2 JP 4306192B2 JP 2002190861 A JP2002190861 A JP 2002190861A JP 2002190861 A JP2002190861 A JP 2002190861A JP 4306192 B2 JP4306192 B2 JP 4306192B2
- Authority
- JP
- Japan
- Prior art keywords
- glycine
- aqueous solution
- alkali metal
- glycine derivative
- solution
- 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 - Fee Related
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- 150000002332 glycine derivatives Chemical class 0.000 title claims description 73
- 238000004519 manufacturing process Methods 0.000 title claims description 40
- 239000007864 aqueous solution Substances 0.000 claims description 115
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 97
- 239000004471 Glycine Substances 0.000 claims description 61
- 238000006243 chemical reaction Methods 0.000 claims description 54
- 239000000243 solution Substances 0.000 claims description 48
- 229910052936 alkali metal sulfate Inorganic materials 0.000 claims description 33
- -1 N-hydroxymethylamino Chemical group 0.000 claims description 32
- 229910052783 alkali metal Inorganic materials 0.000 claims description 31
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 30
- DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 claims description 30
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 150000001412 amines Chemical class 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical group [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 23
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 23
- 235000011152 sodium sulphate Nutrition 0.000 claims description 23
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 19
- LTYRAPJYLUPLCI-UHFFFAOYSA-N glycolonitrile Chemical compound OCC#N LTYRAPJYLUPLCI-UHFFFAOYSA-N 0.000 claims description 19
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000002002 slurry Substances 0.000 claims description 11
- 238000000926 separation method Methods 0.000 claims description 10
- 229910021529 ammonia Inorganic materials 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 9
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 9
- FFDGPVCHZBVARC-UHFFFAOYSA-N N,N-dimethylglycine Chemical group CN(C)CC(O)=O FFDGPVCHZBVARC-UHFFFAOYSA-N 0.000 claims description 7
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 230000003472 neutralizing effect Effects 0.000 claims description 6
- LVPZSMIBSMMLPI-UHFFFAOYSA-N 2-(diethylamino)acetonitrile Chemical compound CCN(CC)CC#N LVPZSMIBSMMLPI-UHFFFAOYSA-N 0.000 claims description 5
- QFPYWIXREIQTOD-UHFFFAOYSA-N 2-amino-4-hydroxybutanenitrile Chemical compound N#CC(N)CCO QFPYWIXREIQTOD-UHFFFAOYSA-N 0.000 claims description 5
- CLVBVRODHJFTGF-UHFFFAOYSA-N 2-piperidin-1-ylacetonitrile Chemical compound N#CCN1CCCCC1 CLVBVRODHJFTGF-UHFFFAOYSA-N 0.000 claims description 5
- 108700003601 dimethylglycine Proteins 0.000 claims description 5
- FOUZISDNESEYLX-UHFFFAOYSA-N 2-(2-hydroxyethylazaniumyl)acetate Chemical compound OCCNCC(O)=O FOUZISDNESEYLX-UHFFFAOYSA-N 0.000 claims description 4
- RPMBPYXLPIWSFJ-UHFFFAOYSA-N 2-aminopentanenitrile Chemical compound CCCC(N)C#N RPMBPYXLPIWSFJ-UHFFFAOYSA-N 0.000 claims description 4
- SGXDXUYKISDCAZ-UHFFFAOYSA-N N,N-diethylglycine Chemical compound CCN(CC)CC(O)=O SGXDXUYKISDCAZ-UHFFFAOYSA-N 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 229940078490 n,n-dimethylglycine Drugs 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- WBTIFBJEYFLFFW-UHFFFAOYSA-N 2-(hydroxymethylazaniumyl)acetate Chemical compound OCNCC(O)=O WBTIFBJEYFLFFW-UHFFFAOYSA-N 0.000 claims description 2
- BOYRGCUYTXBPQH-UHFFFAOYSA-N 2-amino-3-hydroxypropanenitrile Chemical compound OCC(N)C#N BOYRGCUYTXBPQH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- IZYFKLAMVLELBP-UHFFFAOYSA-N 2-(2-methylpiperidin-1-ium-1-yl)acetate Chemical class CC1CCCCN1CC(O)=O IZYFKLAMVLELBP-UHFFFAOYSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 14
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 9
- 230000007423 decrease Effects 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- 235000011114 ammonium hydroxide Nutrition 0.000 description 6
- 239000012295 chemical reaction liquid Substances 0.000 description 6
- WUWHFEHKUQVYLF-UHFFFAOYSA-M sodium;2-aminoacetate Chemical compound [Na+].NCC([O-])=O WUWHFEHKUQVYLF-UHFFFAOYSA-M 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 4
- VRDBIJCCXDEZJN-UHFFFAOYSA-N 2-piperidin-1-ylacetic acid Chemical compound OC(=O)CN1CCCCC1 VRDBIJCCXDEZJN-UHFFFAOYSA-N 0.000 description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 3
- FSVCELGFZIQNCK-UHFFFAOYSA-N N,N-bis(2-hydroxyethyl)glycine Chemical compound OCCN(CCO)CC(O)=O FSVCELGFZIQNCK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000008361 aminoacetonitriles Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000012266 salt solution Substances 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- QGPBIYNLYDWLQE-UHFFFAOYSA-M sodium;2-(dimethylamino)acetate Chemical compound [Na+].CN(C)CC([O-])=O QGPBIYNLYDWLQE-UHFFFAOYSA-M 0.000 description 3
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000909 electrodialysis Methods 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XZQDOIKSUNQDGV-UHFFFAOYSA-N 2-(diethylamino)acetic acid;sodium Chemical compound [Na].CCN(CC)CC(O)=O XZQDOIKSUNQDGV-UHFFFAOYSA-N 0.000 description 1
- HXFCUMCLVYNZDM-UHFFFAOYSA-N 2-aminoacetic acid;sodium Chemical compound [Na].NCC(O)=O HXFCUMCLVYNZDM-UHFFFAOYSA-N 0.000 description 1
- QQSNSWURGHFCDV-UHFFFAOYSA-N 2-piperidin-1-ylacetic acid;sodium Chemical compound [Na].OC(=O)CN1CCCCC1 QQSNSWURGHFCDV-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003147 glycosyl group Chemical group 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- WXFLIROEULQDMT-UHFFFAOYSA-M sodium;2-(diethylamino)acetate Chemical compound [Na+].CCN(CC)CC([O-])=O WXFLIROEULQDMT-UHFFFAOYSA-M 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002190861A JP4306192B2 (ja) | 2001-10-05 | 2002-06-28 | グリシン誘導体の製造方法 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001-310473 | 2001-10-05 | ||
| JP2001310473 | 2001-10-05 | ||
| JP2002190861A JP4306192B2 (ja) | 2001-10-05 | 2002-06-28 | グリシン誘導体の製造方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003176261A JP2003176261A (ja) | 2003-06-24 |
| JP2003176261A5 JP2003176261A5 (https=) | 2005-08-25 |
| JP4306192B2 true JP4306192B2 (ja) | 2009-07-29 |
Family
ID=26623786
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002190861A Expired - Fee Related JP4306192B2 (ja) | 2001-10-05 | 2002-06-28 | グリシン誘導体の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP4306192B2 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104610078A (zh) * | 2014-10-27 | 2015-05-13 | 河北诚信有限责任公司 | 一种制备高纯度n,n-二甲基甘氨酸的方法 |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003031390A1 (en) * | 2001-10-05 | 2003-04-17 | Showa Denko K.K. | Highly concentrated aqueous solutions of n,n-dialkyl- glycines and process for preparation thereof |
| CN103342652B (zh) * | 2013-07-24 | 2015-02-25 | 重庆紫光化工股份有限公司 | N,n-二甲基氨基乙酸酯的制备方法 |
| CN103351306B (zh) * | 2013-07-24 | 2015-04-15 | 重庆紫光化工股份有限公司 | 一种一锅法制备n,n-二甲基甘氨酸酯的方法 |
| CN103387518B (zh) * | 2013-07-24 | 2016-06-08 | 重庆紫光化工股份有限公司 | 一种n,n-二甲基甘氨酸的制备方法 |
| CN103922952A (zh) * | 2014-05-07 | 2014-07-16 | 宁夏宝马药业有限公司 | 用羟基乙腈制取环丙基甘氨酸的方法 |
| CN107216256B (zh) * | 2017-05-19 | 2019-06-21 | 舞阳威森生物医药有限公司 | 一种n，n-二异丙基乙二胺的合成方法 |
| CN112986423B (zh) * | 2021-02-07 | 2022-09-23 | 山东京博生物科技有限公司 | 一种氨基乙腈盐酸盐的含量分析方法及其应用 |
-
2002
- 2002-06-28 JP JP2002190861A patent/JP4306192B2/ja not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104610078A (zh) * | 2014-10-27 | 2015-05-13 | 河北诚信有限责任公司 | 一种制备高纯度n,n-二甲基甘氨酸的方法 |
| CN104610078B (zh) * | 2014-10-27 | 2017-07-11 | 河北诚信有限责任公司 | 一种制备高纯度n,n‑二甲基甘氨酸的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2003176261A (ja) | 2003-06-24 |
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