CA1105489A - Production of nitroguanidine from guanidine nitrate through the action of aqueous sulfuric acid - Google Patents
Production of nitroguanidine from guanidine nitrate through the action of aqueous sulfuric acidInfo
- Publication number
- CA1105489A CA1105489A CA300,926A CA300926A CA1105489A CA 1105489 A CA1105489 A CA 1105489A CA 300926 A CA300926 A CA 300926A CA 1105489 A CA1105489 A CA 1105489A
- Authority
- CA
- Canada
- Prior art keywords
- sulfuric acid
- acid
- nitroguanidine
- carried out
- fact
- 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 title claims abstract description 86
- IDCPFAYURAQKDZ-UHFFFAOYSA-N 1-nitroguanidine Chemical compound NC(=N)N[N+]([O-])=O IDCPFAYURAQKDZ-UHFFFAOYSA-N 0.000 title claims abstract description 33
- NDEMNVPZDAFUKN-UHFFFAOYSA-N guanidine;nitric acid Chemical compound NC(N)=N.O[N+]([O-])=O.O[N+]([O-])=O NDEMNVPZDAFUKN-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 35
- 239000002253 acid Substances 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 5
- 238000000926 separation method Methods 0.000 claims abstract description 4
- 238000010924 continuous production Methods 0.000 claims abstract description 3
- 230000018044 dehydration Effects 0.000 claims 2
- 238000006297 dehydration reaction Methods 0.000 claims 2
- 208000005156 Dehydration Diseases 0.000 abstract description 4
- 230000035484 reaction time Effects 0.000 abstract description 2
- 229910002651 NO3 Inorganic materials 0.000 abstract 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract 1
- 239000012535 impurity Substances 0.000 description 6
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 5
- 229940044197 ammonium sulfate Drugs 0.000 description 5
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 5
- 235000011130 ammonium sulphate Nutrition 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- 230000004087 circulation Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2745783.6 | 1977-10-12 | ||
| DE19772745783 DE2745783C3 (de) | 1977-10-12 | 1977-10-12 | Herstellung von Nitroguanidin aus Guanidinnitrat unter Einwirkung von wässriger Schwefelsäure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1105489A true CA1105489A (en) | 1981-07-21 |
Family
ID=6021217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA300,926A Expired CA1105489A (en) | 1977-10-12 | 1978-04-11 | Production of nitroguanidine from guanidine nitrate through the action of aqueous sulfuric acid |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5849538B2 (de) |
| AT (1) | AT359081B (de) |
| BE (1) | BE867685A (de) |
| CA (1) | CA1105489A (de) |
| CH (1) | CH634827A5 (de) |
| DE (1) | DE2745783C3 (de) |
| FR (1) | FR2405929A1 (de) |
| GB (1) | GB1603247A (de) |
| IN (1) | IN148716B (de) |
| IT (1) | IT1096260B (de) |
| NL (1) | NL7803712A (de) |
| ZA (1) | ZA781967B (de) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105152984A (zh) * | 2015-09-02 | 2015-12-16 | 南通天泽化工有限公司 | 一种硝基胍连续合成方法 |
| CN111675634A (zh) * | 2020-07-17 | 2020-09-18 | 宁夏东吴农化股份有限公司 | 一种硝基胍的制备方法 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112194599A (zh) * | 2020-10-13 | 2021-01-08 | 西安万德能源化学股份有限公司 | 一种硝基胍生产工艺 |
| CN112920091A (zh) * | 2020-12-31 | 2021-06-08 | 宁夏天泽新材料科技有限公司 | 一种硝基胍制备工艺 |
| CN115160188B (zh) * | 2022-07-06 | 2024-01-16 | 贝利特化学股份有限公司 | 一种微通道中制备硝基胍的方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE964411C (de) * | 1939-03-23 | 1957-05-23 | Bayerische Stickstoff Werke Ge | Verfahren zur Herstellung von Nitroguanidin aus Guanidinnitrat |
| GB572931A (en) * | 1941-06-26 | 1945-10-30 | American Cyanamid Co | Improvements in or relating to the preparation of nitro-guanidine |
| DE1234204B (de) * | 1963-01-09 | 1967-02-16 | M Thoma | Verfahren zur Herstellung von Nitroguanidin aus Guanidinnitrat |
-
1977
- 1977-10-12 DE DE19772745783 patent/DE2745783C3/de not_active Expired
-
1978
- 1978-04-06 ZA ZA00781967A patent/ZA781967B/xx unknown
- 1978-04-07 NL NL7803712A patent/NL7803712A/xx not_active Application Discontinuation
- 1978-04-07 CH CH378878A patent/CH634827A5/de not_active IP Right Cessation
- 1978-04-11 CA CA300,926A patent/CA1105489A/en not_active Expired
- 1978-04-26 AT AT299978A patent/AT359081B/de active
- 1978-05-03 IT IT22979/78A patent/IT1096260B/it active
- 1978-05-04 IN IN488/CAL/78A patent/IN148716B/en unknown
- 1978-05-11 GB GB19059/78A patent/GB1603247A/en not_active Expired
- 1978-05-11 FR FR7814995A patent/FR2405929A1/fr active Granted
- 1978-05-31 BE BE188220A patent/BE867685A/xx not_active IP Right Cessation
- 1978-10-06 JP JP12406978A patent/JPS5849538B2/ja not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105152984A (zh) * | 2015-09-02 | 2015-12-16 | 南通天泽化工有限公司 | 一种硝基胍连续合成方法 |
| CN111675634A (zh) * | 2020-07-17 | 2020-09-18 | 宁夏东吴农化股份有限公司 | 一种硝基胍的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| IT7822979A0 (it) | 1978-05-03 |
| BE867685A (fr) | 1978-09-18 |
| AT359081B (de) | 1980-10-27 |
| FR2405929A1 (fr) | 1979-05-11 |
| CH634827A5 (en) | 1983-02-28 |
| IT1096260B (it) | 1985-08-26 |
| GB1603247A (en) | 1981-11-18 |
| ZA781967B (en) | 1979-06-27 |
| ATA299978A (de) | 1980-03-15 |
| NL7803712A (nl) | 1979-04-18 |
| DE2745783C3 (de) | 1987-09-10 |
| JPS5849538B2 (ja) | 1983-11-05 |
| IN148716B (de) | 1981-05-23 |
| DE2745783B2 (de) | 1981-01-22 |
| FR2405929B1 (de) | 1983-12-23 |
| JPS5461122A (en) | 1979-05-17 |
| DE2745783A1 (de) | 1979-04-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |