GB1560377A - Method of producing 2,4 - dioxohixahydro - 1,3,5 - triazine - Google Patents
Method of producing 2,4 - dioxohixahydro - 1,3,5 - triazine Download PDFInfo
- Publication number
- GB1560377A GB1560377A GB16160/78A GB1616078A GB1560377A GB 1560377 A GB1560377 A GB 1560377A GB 16160/78 A GB16160/78 A GB 16160/78A GB 1616078 A GB1616078 A GB 1616078A GB 1560377 A GB1560377 A GB 1560377A
- Authority
- GB
- United Kingdom
- Prior art keywords
- urea
- triazine
- formaldehyde
- component
- dioxohexahydro
- 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
- 238000000034 method Methods 0.000 title claims description 49
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 71
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000004202 carbamide Substances 0.000 claims abstract description 36
- YTFXKURWTLWPKK-UHFFFAOYSA-N 1,3,5-triazinane-2,4-dione Chemical compound O=C1NCNC(=O)N1 YTFXKURWTLWPKK-UHFFFAOYSA-N 0.000 claims abstract description 29
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 239000011541 reaction mixture Substances 0.000 claims abstract description 6
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims description 14
- 239000007795 chemical reaction product Substances 0.000 claims description 13
- 229920001807 Urea-formaldehyde Polymers 0.000 claims description 12
- 239000007859 condensation product Substances 0.000 claims description 8
- 239000004312 hexamethylene tetramine Substances 0.000 claims description 8
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims description 8
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 claims description 8
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 7
- 229920002866 paraformaldehyde Polymers 0.000 claims description 7
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 claims description 6
- 229950005308 oxymethurea Drugs 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 239000006227 byproduct Substances 0.000 abstract description 5
- 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
- KQVLODRFGIKJHZ-UHFFFAOYSA-N methylenediurea Chemical compound NC(=O)NCNC(N)=O KQVLODRFGIKJHZ-UHFFFAOYSA-N 0.000 description 15
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000007669 thermal treatment Methods 0.000 description 2
- JUMKGYUEKMFOGQ-UHFFFAOYSA-N (carbamoylamino)methylideneurea Chemical compound NC(=O)NC=NC(N)=O JUMKGYUEKMFOGQ-UHFFFAOYSA-N 0.000 description 1
- CZGXSFUWZOKPNW-UHFFFAOYSA-N 1-carbamoyl-3-(hydroxymethyl)urea Chemical compound NC(=O)NC(=O)NCO CZGXSFUWZOKPNW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid 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
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000004992 fission Effects 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 239000012265 solid product 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)
Abstract
2,4-Dioxohexahydro-1,3,5-triazine is obtained, avoiding unwanted by-products, by reacting formaldehyde, or compounds which donate formaldehyde, with urea. The urea is used in an amount such that the molar ratio of formaldehyde to urea in the reaction mixture is from 1:2.1 to 1:4.5. Reaction is carried out from 100 to 300 DEG C. The compound is used, for example, for the preparation of compounds having bactericidal and fungicidal properties, and for the preparation of polymers having high thermal stability. It is also suitable as a slow-acting nitrogen fertilizer.
Description
(54) METHOD OF PRODUCING 2,4-DIOXOHEXAHYDRO-1,3,5-TRIAZINE
(71) We, VEB LEUNA-WERKE 'WAL- TER ULBRICHT", of 422 Leuna 3, German
Democratic Republic, a corporation organised and existing under the laws of the
German Democratic Republic, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement :
The present invention relates to a method of producing 2,4dioxohexahydro-l 3,5 triazine.
2,4-dioxohexahydro-l ,3,5-triazine is a compound which can be used, for example, for the production of compounds with bactericidal and fungicidal properties or of polymers with high thermal stability.
Furthermore, 2,4-dioxohexahydro-1,3,5- triazine is suitable as a slow acting nitrogen fertilizer.
The production of 2,4-dioxohexahydro-l , 3,5-triazine has often been described in the literature. The known methods of production have considerable disadvantages, however, particularly with regard to insufficient yield and insufficient purity.
It is known to produce 2,4-dioxohexahydro-1,3,5-triezine by treating methylenebisurea with 4.5 times the amount by weight of concentrated hydrochloric acid (German
Patent Specification 479349). A disadvantage of this prior German method, apart from the use of large amounts of acid which have to be evaporated, is the fact that the 2,4-dioxohexahydro-l ,3,5-triazine is ohtained in oily form and only changes over into the solid state after treatment with water. Information regarding yield and purity obtainable is not contained in the prior German Patent Specification.
Furthermore, it is known to produce 2,4 dioxohexahydro-l ,3,5-triazine by heating dry methylenebisurea to 150 to 230 C.
In German Patent Specification 694823, the production of 2,4-dioxohexabydro-1,3,5- triazine is described by heating methylene bisurea to 100 to 230"C under vacuum.
without any details regarding purity and yield obtainable.
According to United States Patent Specification 3470175, 2,4-dioxohexahydrcs- ],3,5- triazine is obtained from methylenebisurea or methylolbiuret by heating to 195"C for 4 to 6 hours, extraction of the reaction mixture with boiling water and concentration of the filtrate obtained, by evaporation.
This United States Specification likewise does not contain any information regarding yield and purity obtainable.
OSTROGOVICH and collaborators (Rev. Chim. (Bucharest) 20 606 (1967) obtained 2,4-dioxohexahydro- 1, 3,5,-triazine with a 35% yield by heating pure methylenebisurea to 203 to 220"C and recrystillization of the product thus obtained.
Furthermore it is known to cause the NHt splitting off from methylenebisurea in an inert organic liquid diluent, the boiling point of which is between 150 and 300"C, particularly between 185 and 265or by heating to 150 to 300"C for several hours (United States Patent Specification 3035055).
The crude product thus obtained, after separation of the diluent, is treated with a low-boiling organic solvent and then recrystallized from water in order to remove insoluble by-products. According to this
United States method, 2,4-dioxohexahydro1,3,5-triazine is obtained with a yield of 67 to 76%.
A disadvantage of this United States method is the expensive after-treatment of the crude 2,4-dioxohexahydro-l ,3,5-triazine to remove the diluent and the insoluble byproducts and the restoration of the organic solvent used which becomes necessary in a technical application.
A. general disadvantage of all known methods which use methylenebisurea as an initial product is the fact that insoluble polymethyleneureas are formed to a considerable extent during the thermal treatment.
The 2,4-dioxohexahydro- 1 ,3,5-triazine obtained from purified methylenebisura by the known methods contains, as a further important by-product, cyanuric acid, which is obviously formed from fissions products of the methylenebisurea. Separation of 2,4 dioxohexahydro-1,3,5-triazine and cyanuric avid by recrystallization from water is not easily possible because the two compounds have substantially the same solubility.
In the known methods starting from methylenebisurea, only a single recrystallization from water was used as a purifying method for the crude 2,4-dioxohexahydro1,3,5-triazine. Since such method is unsuitable for the far-reaching separation of the cyanuric acid, contaminated 2,4-dioxohexahydro-1,3,5-triazine is obtained by the known methods and as a result, too high a yield is simulated.
Finally, it is known to produce 2,4-dioxohexahydro-1,3,5-triazine by catalytic hydrogenation of 5-azaurazil (2,4-dioxotetrahydro-1,3,5-triazine) (A. PISKALA, J.
GUT Coll.Chech,Chem.Comm.26 2519 29 (1961)). 5-azaurazil can be obtained, for example, by condensation of biuret with the ethyl ester of formic acid or by cyclization of N,N'-dicarbamoylformamidine.
A disadvantage of this method is that the 5-azaurazil serving as the initial product can only be produced with difficulty with a relatively poor yield and is not available on a commercial scale.
It is the object of the invention to produce 2,4-dioxohexahydro-l ,3,5-triazine from substances which are readily available on an industrial scale, in a simple manner with high yields.
According to the present invention there is provided a method of producing 2,4 dioxohexahydro-1,3,5-triazine comprising reacting a component (A), comprising formaldehyde or a substance, capable of releasing formaldehyde during the reaction, with a component (B), comprising urea, intermittently or continuously at a temperature from 100 to 3000it in the presence of sufficient urea to provide in the reaction mixture mol ratios of formaldehyde to urea of 1:21 to 1:45 Preferably component (A) comprises methylenebisurea, hexamethylenetetramine, paraformaldehyde, aqueous formaldehyde a solid urea-formaldehyde condensation product or dimethylolurea. The reaction temperature may be from 100 to 250"C. Generally the reaction time extends from 1 to 40 hours.
Surprisingly, when methylenebisurea is heated in the presence of urea, the formation of insoluble polymethyleneureas taking place as a secondary reaction is prevented or largely suppressed in favour of the formation of 2,4-dioxohexahydro-1,3,5- triazine.
Similarly, it was found, that when mixtures of urea and paraformaldehyde or hexamethvlenetetramine are heated, in which case a number of reactions are theoretically possible, as a result of the presence of excess urea, the course of the reaction is steered preferentially in the direction of the formation of 2,4-dioxohexahydro-l ,3,5-triazine.
Furthermore, it was found, surprisingly, that polymethyleneureas and other ureaformaldehyde condensation products were suitable as initial products for the production of 2,4-dioxohexahydro-1,3,5-triazine by the method according to the invention.
When these products are heated in the presence of urea, a decomposition of the higher molecular compounds to lower molecular compounds occurs, which, under the reaction conditions, react further to form 2,4 dioxohexahydro-1 ,3,5-triazine. From this it is clear that the urea present in the reaction mixture in the method according to the invention does not simply act as a diluent and flux but, contrary to expectation, decisively influences the course of the chemical reactions.
Cyanuric acid is likewise formed as a byproduct during the production of 2,4-dioxohexahydro-1,3,5-triazine by the method according to the invention. Since it is known that considerable amounts of cyanuric aecid are formed when urea is heated to above 200 lC, it had to be assumed that as a result of the presence of excess urea in the method according to the invention, it would lead to an increased formation of cyanuric acid in comparison with the known methods. Surprisingly, however, this is not the case to the extent expected.
In the method according to the invention, the reaction times may in general amount to up to 40 hours depending on the reaction temperature selected.
The excess of urea is preferably selected so that the content of decomposition products of the urea in the reaction product remains within tolerable limits. If methylenebisurea, for example, is used as an initial product, sufficient urea should preferably be added to provide a mol ratio of formaldehyde to urea of 1:2 18 to 3 0.
When paraformaldehyde or hexamethylenetetramine or ordinary commercial ureaformaldehyde condensation products are used, it is advisable to measure out the amount of urea so that mol ratios of formaldehyde to urea of 1: 21 to 40 result.
The method can be carried out intermittently or continuously.
The method according to the invention has several advantages over the known methods.
Thus, for instance, during the thermal treatment of methylenebisurea in the presence of urea, the reaction is steered preferentially in the direction of the formation of 2,4-dioxohexahydro-l,3,5-triazine and the formation of insoluble hy-products, particularly polymethyleneureas, is suppressed.
As a result, an increase in the yield of 2,4dioxohexahydro-1,3,5-triazine is possible.
Furthermore, the method according to the invention renders it possible to ispellse with a separate production of methylenebisurea as an intermediate product and instead of this to use simple reactants which are readily available on a commercial scale, such as urea and paraformaldehyde or aqueous formaldehyde solutions or hexamethylenetetramine, or ordinary commercial urea-formaldehyde condensation products such as size, slow acting nitrogen fertilizers or dimethylolurea, and to produce 2,4dioxohexahydro-1,3,5-triazine therefrom in a singlestage process.
Finally, the reaction of solids is facilitated by the presence of urea.
The invention is ilustrated by the following examples wherein parts and percentages are by weight:
Example I
A mixture of 7 parts of purified methylenebisurea and 3 parts of urea are heated to 200 to 2100C for 4 hours in a drying oven. The 2,4-dioxohexahydro-1,3,5-triazine obtained thereby contains 2 3 % of polymethyleneureas which are insoluble in water and 108% of cyanuric acid. The yield of 2,4dioxohexahydro-1 ,3,5-triazine, based on formaldehyde, amounts to 95%.
If purified methylenebisures is heated alone, however, 2,4-dioxohexahydro-1,3,5- triazine is only formed with a yield of 21 %.
The reaction product contains 562% of polymethyleneureas which are insoluble in water and 136% of cyanuric acid.
Example 2
A mixture of 8-2 parts of hexamethylenetetramine and 60 parts of urea are thermally treated under the same conditions as in Example 1. The reaction product contains 05% of polymethyleneureas which are insoluble in water and 93% of cyanuric acid. The yield of 2,4-dioxohexahydro1,3,5-triazine, based on the formaldehyde used in the form of hexamethylenetetramine, amounts to 753%.
Example 3
A mixture of 10 5 parts of paraformaldehyde tnd 60 parts of urea is heated to 220 to 2300C for 80 minutes. The reaction product contains 8% of polymethyleneureas which are insoluble in water and 13.8% of cyanuric acid. The yield of 2,4-dioxohexahydro-1,3,5-triazine, based on formaldehyde, amounts to 715%.
Example 4
A solution of 60 parts of urea in 203 parts of aqueous 37% solution of formaldehyde is evaporated until dry and the remaining residue is heated to 180 to 1900C for 8 hours. The reaction product obtained is substantially free of polymethyleneureas which are insoluble in water and contains 17-5% of cyanuric acid. The yield of 2,4 dioxohexahydro-1 ,3,5-triazine, based on the formaldehyde used, amounts to 86-3%.
Example 5
An ordinary commercial powdery ureaformaldehyde resin size is mixed with sufficient urea so as to provide a mol ratio of formaldehyde to urea of 1:4 in the mixture.
When this mixture is heated to 200 to 210 C for 4 hours, a reaction product is obtained which is substantially free of polymethyleneureas which are insoluble in water and contains 21% of cyanuric acid. The yield of 2,4-dioxohexahydro-l,3,5-triazine, based on the formaldehyde used in the form of urea-formaldehyde resin, amounts to 747%.
Example 6
During the conversion of a urea-formaldehyde condensation product (of the kind which is suitable as a slow acting nitrogen fertilizer) under the conditions indicated in Example 5, a reaction product is obtainable which contains 2'4 % of polymethyleneureas which are insoluble in water and 23% of cyanuric acid. The yield of 2,4-dioxohexahydro-l,3,5-triazine, based on the formaldehyde used in the form of the urea-formaldehyde condensation products amounts to 71.8%.
Example 7
A mixture of 60 parts of dimethylolurea and 120 parts of urea is heated to 170 to 1800C for 32 hours. The reaction product contains 21 % of polymethyleneureas which are insoluble in water and 9-3 /O of cyanuric acid. The yield of 2,4-dioxohexahydro1,3,5-triazine, based on the formaldehyde used in the form of dimethylolurea, amounts to 832%.
Example 8 8 2 parts of hexamethylenetetramine and 60 parts of urea are introduced hourly into a cylindrical, horizontally disposed heatable reactor which is provided with devices for mixing and conveying solid products and for drawing off gaseous reaction products.
The temperature in the reactor is selected so that a temperature of 100 to 1300C prevails at the inlet to the reactor and a temperature of 220 to 2300;C at the outlet from the reactor. The conveying speed is adjusted so that an average treatment time of 25 hours results. 47.7 parts of reaction product are discharged hourly from the reactor through a discharge device. The reaction product is substantially free of polymethyleneureas which are insoluble in water; it contains 75% of cyanuric acid.
The yield of 2,Sdioxohexahydro-1,3,5- triazine, based on the formaldehyde used in the form of hexanethylenetetraminc.
amounts to 778%.
WHAT WE CLAIM IS: 1. A method of producing 2,4-dioxohexahydro-1,3,5-triazine comprising reacting a component (A), comprising formaldehyde or a substance capable of releasing formaldehyde during the reaction, with a component (B), comprising urea, intermittently or continuously at a temperature from 100 to 300 C in the presence of sufficient urea to provide in the reaction mixture mol ratios of-formaldehyde to urea of 1:21 to 1:45.
2. A method according to Claim l.
wherein component (A) comprises methy lenebisurca.
3. A method according to Claim 1, wherein component (A) comprises hexamethylenetetramine.
4. A method according to Claim 1, wherein component (A) comprises paraformaldehyde.
5. A method according to Claim 1, wherein component (A) comprises aqueous formaldehyde.
6. A method according to Claim 1, wherein component (A) comprises a solid urea-formaldehyde condensation product.
7. A method according to Claim 1, wherein component (A) comprises dimethylolurea.
8. A method according to any preceding claim, wherein the temperature is from 100 to 250"C.
9. A method according to any preceding claim, wherein the reaction time extends from 1 to 40 hours.
10. A method according to Claim 1 substantially as herein described and exem purified.
11. 2,4-dioxohexahydro-1,3,5-triazine which has been prepared by the method claimed in any preceding claim.
**WARNING** end of DESC field may overlap start of CLMS **.
Claims (11)
1. A method of producing 2,4-dioxohexahydro-1,3,5-triazine comprising reacting a component (A), comprising formaldehyde or a substance capable of releasing formaldehyde during the reaction, with a component (B), comprising urea, intermittently or continuously at a temperature from 100 to 300 C in the presence of sufficient urea to provide in the reaction mixture mol ratios of-formaldehyde to urea of 1:21 to 1:45.
2. A method according to Claim l.
wherein component (A) comprises methy lenebisurca.
3. A method according to Claim 1, wherein component (A) comprises hexamethylenetetramine.
4. A method according to Claim 1, wherein component (A) comprises paraformaldehyde.
5. A method according to Claim 1, wherein component (A) comprises aqueous formaldehyde.
6. A method according to Claim 1, wherein component (A) comprises a solid urea-formaldehyde condensation product.
7. A method according to Claim 1, wherein component (A) comprises dimethylolurea.
8. A method according to any preceding claim, wherein the temperature is from 100 to 250"C.
9. A method according to any preceding claim, wherein the reaction time extends from 1 to 40 hours.
10. A method according to Claim 1 substantially as herein described and exem purified.
11. 2,4-dioxohexahydro-1,3,5-triazine which has been prepared by the method claimed in any preceding claim.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD19861677A DD130479B1 (en) | 1977-04-27 | 1977-04-27 | PROCESS FOR THE PREPARATION OF 2.4-DIOXOHEXAHYDRO-1.3.5-TRIAZINE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1560377A true GB1560377A (en) | 1980-02-06 |
Family
ID=5508154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16160/78A Expired GB1560377A (en) | 1977-04-27 | 1978-04-24 | Method of producing 2,4 - dioxohixahydro - 1,3,5 - triazine |
Country Status (12)
| Country | Link |
|---|---|
| BG (1) | BG30530A1 (en) |
| CH (1) | CH636864A5 (en) |
| CS (1) | CS200805B1 (en) |
| DD (1) | DD130479B1 (en) |
| DE (1) | DE2807218A1 (en) |
| FR (1) | FR2388801A1 (en) |
| GB (1) | GB1560377A (en) |
| HU (1) | HU176818B (en) |
| IT (1) | IT1105405B (en) |
| NL (1) | NL7804453A (en) |
| PL (1) | PL206390A1 (en) |
| SU (1) | SU920054A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD229694A1 (en) * | 1984-12-17 | 1985-11-13 | Leuna Werke Veb | PROCESS FOR PREPARING 1,5-DIACETYL-2,4-DIOXO-HEXAHYDRO-1,3,5-TRIAZINE |
| DD237437A3 (en) * | 1984-12-17 | 1986-07-16 | Leuna Werke Veb | PROCESS FOR THE PREPARATION OF 2,4-DIOXOHEXOHYDRO-1.3.5-TRIAZINE |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3035055A (en) * | 1962-05-15 | Methylene diurea | ||
| DE694823C (en) * | 1938-07-15 | 1940-08-09 | I G Farbenindustrie Akt Ges | Method for making a triazine capsule |
-
1977
- 1977-04-27 DD DD19861677A patent/DD130479B1/en unknown
-
1978
- 1978-02-20 DE DE19782807218 patent/DE2807218A1/en not_active Withdrawn
- 1978-03-24 BG BG7839151A patent/BG30530A1/en unknown
- 1978-03-24 SU SU787770141A patent/SU920054A1/en active
- 1978-04-06 CH CH372578A patent/CH636864A5/en not_active IP Right Cessation
- 1978-04-24 CS CS782638A patent/CS200805B1/en unknown
- 1978-04-24 FR FR7812074A patent/FR2388801A1/en active Granted
- 1978-04-24 GB GB16160/78A patent/GB1560377A/en not_active Expired
- 1978-04-26 IT IT49076/78A patent/IT1105405B/en active
- 1978-04-26 NL NL7804453A patent/NL7804453A/en not_active Application Discontinuation
- 1978-04-26 PL PL20639078A patent/PL206390A1/en unknown
- 1978-04-27 HU HU78LE829A patent/HU176818B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS200805B1 (en) | 1980-09-15 |
| BG30530A1 (en) | 1981-07-15 |
| HU176818B (en) | 1981-05-28 |
| DD130479A1 (en) | 1978-04-05 |
| IT7849076A0 (en) | 1978-04-26 |
| FR2388801B1 (en) | 1983-05-20 |
| PL206390A1 (en) | 1979-03-12 |
| FR2388801A1 (en) | 1978-11-24 |
| CH636864A5 (en) | 1983-06-30 |
| SU920054A1 (en) | 1982-04-15 |
| IT1105405B (en) | 1985-11-04 |
| DD130479B1 (en) | 1980-03-12 |
| DE2807218A1 (en) | 1978-11-02 |
| NL7804453A (en) | 1978-10-31 |
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| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |