JP4758584B2 - １−メチル−３−ニトログアニジンの製造方法 - Google Patents
１−メチル−３−ニトログアニジンの製造方法 Download PDFInfo
- Publication number
- JP4758584B2 JP4758584B2 JP2001555041A JP2001555041A JP4758584B2 JP 4758584 B2 JP4758584 B2 JP 4758584B2 JP 2001555041 A JP2001555041 A JP 2001555041A JP 2001555041 A JP2001555041 A JP 2001555041A JP 4758584 B2 JP4758584 B2 JP 4758584B2
- Authority
- JP
- Japan
- Prior art keywords
- nitroguanidine
- methyl
- value
- methylamine
- methylammonium
- 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
Links
- XCXKNNGWSDYMMS-UHFFFAOYSA-N 2-methyl-1-nitroguanidine Chemical compound CNC(N)=N[N+]([O-])=O XCXKNNGWSDYMMS-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title abstract description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 18
- IDCPFAYURAQKDZ-UHFFFAOYSA-N 1-nitroguanidine Chemical compound NC(=N)N[N+]([O-])=O IDCPFAYURAQKDZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000007864 aqueous solution Substances 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 description 5
- YPHRUNNJDBFKHK-UHFFFAOYSA-N 2-methylguanidine;nitric acid Chemical compound O[N+]([O-])=O.CN=C(N)N YPHRUNNJDBFKHK-UHFFFAOYSA-N 0.000 description 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N methylguanidine Chemical compound CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000012467 final product Substances 0.000 description 3
- PTIUDKQYXMFYAI-UHFFFAOYSA-N methylammonium nitrate Chemical compound NC.O[N+]([O-])=O PTIUDKQYXMFYAI-UHFFFAOYSA-N 0.000 description 3
- 239000002351 wastewater Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- NQNOMXXYKHWVKR-UHFFFAOYSA-N methylazanium;sulfate Chemical compound NC.NC.OS(O)(=O)=O NQNOMXXYKHWVKR-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- MXGMWOVBYAQMPV-UHFFFAOYSA-N 1,2-dimethyl-3-nitroguanidine Chemical class CNC(=NC)N[N+]([O-])=O MXGMWOVBYAQMPV-UHFFFAOYSA-N 0.000 description 1
- WTYJBGQERCCGAD-UHFFFAOYSA-N 1-Methylguanidine sulfate (2:1) Chemical compound CN=C(N)N.CN=C(N)N.OS(O)(=O)=O WTYJBGQERCCGAD-UHFFFAOYSA-N 0.000 description 1
- MVXMNHYVCLMLDD-UHFFFAOYSA-N 4-methoxynaphthalene-1-carbaldehyde Chemical compound C1=CC=C2C(OC)=CC=C(C=O)C2=C1 MVXMNHYVCLMLDD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- -1 methyl mercapto group Chemical group 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C277/08—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of substituted guanidines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10003834A DE10003834A1 (de) | 2000-01-28 | 2000-01-28 | Verfahren zur Herstellung von 1-Methyl-3-nitroguanidin |
| DE10003834.4 | 2000-01-28 | ||
| PCT/EP2001/000351 WO2001055099A1 (de) | 2000-01-28 | 2001-01-12 | Verfahren zur herstellung von 1-methyl-3-nitroguanidin |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003523969A JP2003523969A (ja) | 2003-08-12 |
| JP2003523969A5 JP2003523969A5 (enExample) | 2005-07-07 |
| JP4758584B2 true JP4758584B2 (ja) | 2011-08-31 |
Family
ID=7629122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001555041A Expired - Fee Related JP4758584B2 (ja) | 2000-01-28 | 2001-01-12 | １−メチル−３−ニトログアニジンの製造方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6486348B1 (enExample) |
| EP (1) | EP1261581B1 (enExample) |
| JP (1) | JP4758584B2 (enExample) |
| AT (1) | ATE327218T1 (enExample) |
| DE (2) | DE10003834A1 (enExample) |
| ES (1) | ES2261374T3 (enExample) |
| WO (1) | WO2001055099A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10000891A1 (de) * | 2000-01-12 | 2001-07-19 | Bayer Ag | Verfahren zur Herstellung von N-Methyl-N'-nitroguanidin |
| CN101565392A (zh) * | 2008-04-21 | 2009-10-28 | 南通天泽化工有限公司 | 一种甲基硝基胍及其制备方法 |
| CN106986790A (zh) * | 2017-05-25 | 2017-07-28 | 宁夏贝利特生物科技有限公司 | 用生产硝基胍后的稀硫酸生产n‑甲基‑n′‑硝基胍的方法 |
| CN107698466A (zh) * | 2017-11-09 | 2018-02-16 | 宁夏贝利特生物科技有限公司 | 一种n‑甲基‑n′‑硝基胍的制备方法 |
| CN109053498A (zh) * | 2018-09-27 | 2018-12-21 | 南通天泽化工有限公司 | 一种1-甲基-1,2-二硝基胍的制备方法 |
| CN117986160A (zh) * | 2023-12-11 | 2024-05-07 | 福诺(宁夏)化工科技有限公司 | 一种甲基硝基胍的制备方法 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09255651A (ja) * | 1996-03-25 | 1997-09-30 | Bayer Ag | Ｎ−メチル−ｎ′−ニトログアニジンの製造法 |
| JPH107645A (ja) * | 1996-06-19 | 1998-01-13 | Mitsui Petrochem Ind Ltd | アルキルニトログアニジン誘導体の製造方法 |
| JP2001516362A (ja) * | 1997-03-27 | 2001-09-25 | バイエル・アクチエンゲゼルシヤフト | Ｎ−アルキル−ｎ′−ニトログアニジン類の製造方法 |
| JP2002530367A (ja) * | 1998-11-25 | 2002-09-17 | デイナミート ノーベル ゲゼルシャフト ミット ベシュレンクテル ハフツング エクスプロジーフシュトッフ− ウント ジステームテヒニク | Ｎ−アルキル−ｎ′−ニトログアニジンの製造法 |
| JP2003519677A (ja) * | 2000-01-12 | 2003-06-24 | バイエル アクチェンゲゼルシャフト | Ｎ−メチル−ｎ’−ニトログアニジンの製造方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW198724B (enExample) * | 1990-10-24 | 1993-01-21 | Ciba Geigy Ag |
-
2000
- 2000-01-28 DE DE10003834A patent/DE10003834A1/de not_active Withdrawn
-
2001
- 2001-01-12 AT AT01901150T patent/ATE327218T1/de active
- 2001-01-12 JP JP2001555041A patent/JP4758584B2/ja not_active Expired - Fee Related
- 2001-01-12 DE DE50109873T patent/DE50109873D1/de not_active Expired - Lifetime
- 2001-01-12 WO PCT/EP2001/000351 patent/WO2001055099A1/de not_active Ceased
- 2001-01-12 ES ES01901150T patent/ES2261374T3/es not_active Expired - Lifetime
- 2001-01-12 EP EP01901150A patent/EP1261581B1/de not_active Expired - Lifetime
-
2002
- 2002-06-05 US US10/161,619 patent/US6486348B1/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09255651A (ja) * | 1996-03-25 | 1997-09-30 | Bayer Ag | Ｎ−メチル−ｎ′−ニトログアニジンの製造法 |
| JPH107645A (ja) * | 1996-06-19 | 1998-01-13 | Mitsui Petrochem Ind Ltd | アルキルニトログアニジン誘導体の製造方法 |
| JP2001516362A (ja) * | 1997-03-27 | 2001-09-25 | バイエル・アクチエンゲゼルシヤフト | Ｎ−アルキル−ｎ′−ニトログアニジン類の製造方法 |
| JP2002530367A (ja) * | 1998-11-25 | 2002-09-17 | デイナミート ノーベル ゲゼルシャフト ミット ベシュレンクテル ハフツング エクスプロジーフシュトッフ− ウント ジステームテヒニク | Ｎ−アルキル−ｎ′−ニトログアニジンの製造法 |
| JP2003519677A (ja) * | 2000-01-12 | 2003-06-24 | バイエル アクチェンゲゼルシャフト | Ｎ−メチル−ｎ’−ニトログアニジンの製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2261374T3 (es) | 2006-11-16 |
| DE50109873D1 (de) | 2006-06-29 |
| JP2003523969A (ja) | 2003-08-12 |
| US20020173675A1 (en) | 2002-11-21 |
| DE10003834A1 (de) | 2001-08-02 |
| EP1261581A1 (de) | 2002-12-04 |
| WO2001055099A1 (de) | 2001-08-02 |
| ATE327218T1 (de) | 2006-06-15 |
| EP1261581B1 (de) | 2006-05-24 |
| US6486348B1 (en) | 2002-11-26 |
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