CS200805B1 - Method of producing 2,4-dioxohexahydro-1,3,5-triazine - Google Patents
Method of producing 2,4-dioxohexahydro-1,3,5-triazine Download PDFInfo
- Publication number
- CS200805B1 CS200805B1 CS782638A CS263878A CS200805B1 CS 200805 B1 CS200805 B1 CS 200805B1 CS 782638 A CS782638 A CS 782638A CS 263878 A CS263878 A CS 263878A CS 200805 B1 CS200805 B1 CS 200805B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- urea
- formaldehyde
- triazine
- dioxohexahydro
- yield
- Prior art date
Links
- YTFXKURWTLWPKK-UHFFFAOYSA-N 1,3,5-triazinane-2,4-dione Chemical compound O=C1NCNC(=O)N1 YTFXKURWTLWPKK-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims description 22
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 39
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 33
- 239000004202 carbamide Substances 0.000 claims abstract description 31
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 239000011541 reaction mixture Substances 0.000 claims abstract description 4
- 229920001807 Urea-formaldehyde Polymers 0.000 claims description 8
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 5
- 239000007859 condensation product Substances 0.000 claims description 5
- 229920002866 paraformaldehyde Polymers 0.000 claims description 5
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 claims description 5
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 4
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 4
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 claims description 4
- 229950005308 oxymethurea Drugs 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- 239000006227 byproduct Substances 0.000 abstract description 7
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract description 4
- 239000000618 nitrogen fertilizer Substances 0.000 abstract description 3
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 2
- 230000000855 fungicidal effect Effects 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 abstract description 2
- 235000013877 carbamide Nutrition 0.000 description 27
- 239000007795 chemical reaction product Substances 0.000 description 10
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- -1 polymethylene Polymers 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- KQVLODRFGIKJHZ-UHFFFAOYSA-N methylenediurea Chemical compound NC(=O)NCNC(N)=O KQVLODRFGIKJHZ-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- GEWRKGDRYZIFNP-UHFFFAOYSA-N 1h-1,3,5-triazine-2,4-dione Chemical compound OC1=NC=NC(O)=N1 GEWRKGDRYZIFNP-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
- YXTCDKLERLUNSA-UHFFFAOYSA-N O=C1NCNC(N1)=O.N1C(=O)NC(=O)N=C1 Chemical compound O=C1NCNC(N1)=O.N1C(=O)NC(=O)N=C1 YXTCDKLERLUNSA-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/10—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fertilizers (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD19861677A DD130479B1 (de) | 1977-04-27 | 1977-04-27 | Verfahren zur herstellung von 2.4-dioxohexahydro-1.3.5-triazin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS200805B1 true CS200805B1 (en) | 1980-09-15 |
Family
ID=5508154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS782638A CS200805B1 (en) | 1977-04-27 | 1978-04-24 | Method of producing 2,4-dioxohexahydro-1,3,5-triazine |
Country Status (12)
| Country | Link |
|---|---|
| BG (1) | BG30530A1 (xx) |
| CH (1) | CH636864A5 (xx) |
| CS (1) | CS200805B1 (xx) |
| DD (1) | DD130479B1 (xx) |
| DE (1) | DE2807218A1 (xx) |
| FR (1) | FR2388801A1 (xx) |
| GB (1) | GB1560377A (xx) |
| HU (1) | HU176818B (xx) |
| IT (1) | IT1105405B (xx) |
| NL (1) | NL7804453A (xx) |
| PL (1) | PL206390A1 (xx) |
| SU (1) | SU920054A1 (xx) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD229694A1 (de) * | 1984-12-17 | 1985-11-13 | Leuna Werke Veb | Verfahren zur herstellung von 1,5-diacetyl-2,4-dioxo-hexahydro-1,3,5-triazin |
| DD237437A3 (de) * | 1984-12-17 | 1986-07-16 | Leuna Werke Veb | Verfahren zur herstellung von 2,4-dioxohexohydro-1.3.5-triazin |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3035055A (en) * | 1962-05-15 | Methylene diurea | ||
| DE694823C (de) * | 1938-07-15 | 1940-08-09 | I G Farbenindustrie Akt Ges | Verfahren zur Herstellung eines Triazinabkoemmlings |
-
1977
- 1977-04-27 DD DD19861677A patent/DD130479B1/de unknown
-
1978
- 1978-02-20 DE DE19782807218 patent/DE2807218A1/de not_active Withdrawn
- 1978-03-24 BG BG7839151A patent/BG30530A1/xx unknown
- 1978-03-24 SU SU787770141A patent/SU920054A1/ru active
- 1978-04-06 CH CH372578A patent/CH636864A5/de not_active IP Right Cessation
- 1978-04-24 CS CS782638A patent/CS200805B1/cs unknown
- 1978-04-24 FR FR7812074A patent/FR2388801A1/fr active Granted
- 1978-04-24 GB GB16160/78A patent/GB1560377A/en not_active Expired
- 1978-04-26 PL PL20639078A patent/PL206390A1/xx unknown
- 1978-04-26 IT IT49076/78A patent/IT1105405B/it active
- 1978-04-26 NL NL7804453A patent/NL7804453A/xx not_active Application Discontinuation
- 1978-04-27 HU HU78LE829A patent/HU176818B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH636864A5 (en) | 1983-06-30 |
| FR2388801B1 (xx) | 1983-05-20 |
| DD130479B1 (de) | 1980-03-12 |
| DE2807218A1 (de) | 1978-11-02 |
| IT1105405B (it) | 1985-11-04 |
| DD130479A1 (de) | 1978-04-05 |
| FR2388801A1 (fr) | 1978-11-24 |
| BG30530A1 (en) | 1981-07-15 |
| NL7804453A (nl) | 1978-10-31 |
| GB1560377A (en) | 1980-02-06 |
| HU176818B (en) | 1981-05-28 |
| SU920054A1 (ru) | 1982-04-15 |
| IT7849076A0 (it) | 1978-04-26 |
| PL206390A1 (pl) | 1979-03-12 |
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