CS235587B1 - Method of polyvinyl chloride plastificing - Google Patents
Method of polyvinyl chloride plastificing Download PDFInfo
- Publication number
- CS235587B1 CS235587B1 CS736083A CS736083A CS235587B1 CS 235587 B1 CS235587 B1 CS 235587B1 CS 736083 A CS736083 A CS 736083A CS 736083 A CS736083 A CS 736083A CS 235587 B1 CS235587 B1 CS 235587B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- dione
- nitration
- imidazol
- tetrahydroimidazo
- nitric acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract description 9
- 229920000915 polyvinyl chloride Polymers 0.000 title 1
- 239000004800 polyvinyl chloride Substances 0.000 title 1
- 238000006396 nitration reaction Methods 0.000 claims abstract description 11
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- QHDUJTCUPWHNPK-UHFFFAOYSA-N methyl 7-methoxy-2h-indazole-3-carboxylate Chemical compound COC1=CC=CC2=C(C(=O)OC)NN=C21 QHDUJTCUPWHNPK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 8
- CDWCUONHXXVAHD-UHFFFAOYSA-N 3a,6a-dinitro-1,3,4,6-tetrahydroimidazo[4,5-d]imidazole-2,5-dione Chemical compound [N+](=O)([O-])C12NC(NC1(NC(N2)=O)[N+](=O)[O-])=O CDWCUONHXXVAHD-UHFFFAOYSA-N 0.000 claims abstract description 4
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 claims description 5
- 238000005303 weighing Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 abstract description 5
- YZTLXSKKFIMAKY-UHFFFAOYSA-N 3,6-dinitro-1,3a,4,6a-tetrahydroimidazo[4,5-d]imidazole-2,5-dione Chemical compound N1C(=O)N([N+]([O-])=O)C2NC(=O)N([N+](=O)[O-])C21 YZTLXSKKFIMAKY-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000654 additive Substances 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000007630 basic procedure Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VKGQPUZNCZPZKI-UHFFFAOYSA-N (diaminomethylideneamino)azanium;sulfate Chemical compound NN=C(N)N.NN=C(N)N.OS(O)(=O)=O VKGQPUZNCZPZKI-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011988 third-generation catalyst Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Vynález pojednává o výrobě dinitrotetrahydroimidazo[ 4,5-d ] imidazól-2,5 (1H,3H) - -diónu, známého pod kódovým označením DINGU, nitráciou tetrahydroimídazo[4,5-djimidazól-2,5(lH,3H]-diónu kyselinou dusičnou, pričom je do; reakčného systému v procese výroby přidaný postupné alebo naraz dusičnan močoviny v množstve 0,01 až 25 % hmot. na hmotnost navážku nitrovanej substancie. Postup podl’a vynálezu zvyšuje ekonomiku a kvalitu produkcie DINGU.The invention relates to the production of dinitrotetrahydroimidazo [ 4,5-d] imidazole-2,5 (1H, 3H) - -dione, known under code designation DINGU, by nitration of tetrahydroimidazo [4,5-dimidazole-2,5 (1H, 3H] -dione nitric acid while being to; reaction system in the process production added incrementally or at once urea nitrate 0.01 to 25% wt. the weight of the nitrated substance. The process of the invention increases the economy and production quality of DING.
Description
* Vynález sa týká sposobu výroby dinitrotetrahydroimidazo [4,5-d ] imidazól-2,5 (1H 3H)-diónu nitráciou tetrahydroimidazo [4,5-d] imidazól-2,5 (1H,3H)-diónu kyselinou dusičnou za přítomnosti dusičnanu močoviny v reakčnom systéme.The invention relates to a process for the preparation of dinitrotetrahydroimidazo [4,5-d] imidazol-2,5 (1H, 3H) -dione by nitration of tetrahydroimidazo [4,5-d] imidazol-2,5 (1H, 3H) -dione with nitric acid in the presence of urea nitrate in the reaction system.
Pódia najnovších poznatkov je výťažnosť a bezpečnosť procesu nitrolýzy a/alebo nitrácie amínov, resp. amidov, na cyklické nitramíny priaznivo ovplyvnená prítomnosťou močoviny, močovinoformaldehydových kondenzátov, amínoguanidínsulfátu a pod. v příslušnéj reakčnej zmesi (viď na pr. čs. autorské osvedčenía číslo 206 382, 213 509, 214 311 a ďalšie). Pravděpodobný mechanizmus působenia niektorých z uvedených aditív bol diskutovaný v niekoikých prácach, napr. v čs. autorskom svedčeniu č. 206 382; jedná sa v podstatě o katalyzátory tretej generácie.The state of the art is the yield and safety of the nitrolysis and / or amine nitration process, respectively. amides, to cyclic nitramines favorably affected by the presence of urea, urea-formaldehyde condensates, aminoguanidine sulfate and the like. in the respective reaction mixture (see, e.g., the author's certificate and number 206 382, 213 509, 214 311 and others). The probable mechanism of action of some of these additives has been discussed in some publications, e.g. in MS. author's certificate no. 206 382; they are basically third generation catalysts.
Pódia tohto vynálezu spočívá spůsob výroby dinitrotetrahydr oimidazo[ 4,5-d] imidazól-2,5 (lH,3H)-diónu v nitrácii tetrahydroimidazo [ 4,5-d ] imidazól-2,5 (1H,3H) -diónu dýmavou kyselinou dusičnou za přítomnosti 0,01 až 25 % hmot. dusičnanu močoviny, s výhodou za přítomnosti 0,3 až 20 % hmot. dusičnanu močoviny v reakčnej zmesi, počítané na návažok nitrovanej substancie, pričom dusičnan močoviny je do reakčného systému přidávaný postupné alebo naraz.According to the present invention, a method for producing dinitrotetrahydr oimidazo [4,5-d] imidazol-2,5 (1H, 3H) -dione by nitration of tetrahydroimidazo [4,5-d] imidazol-2,5 (1H, 3H) -dione is fuming % nitric acid in the presence of 0.01 to 25 wt. % urea nitrate, preferably in the presence of 0.3 to 20 wt. urea nitrate in the reaction mixture, calculated on the weight of the nitrated substance, wherein urea nitrate is added to the reaction system gradually or simultaneously.
Výhodou tohto vynálezu je zvýšenie výťažnosti procesu technicky dostupným aditívom, ktorého přítomnost v reakčnom systéme obecne zvyšuje i bezpečnosť procesu. Ďalšou výhodou je zvýšenie stability produktu nitrácie v přítomnosti aditíva.An advantage of the present invention is to increase the process yield by a technically available additive whose presence in the reaction system generally also increases process safety. Another advantage is to increase the stability of the nitration product in the presence of an additive.
Postup podlá tohto vynálezu nebol doposial' publikovaný a je dokumentovaný nasledujúcim príkládom, ktorý však v žiadnom případe nevylučuje možnú variabilitu postupu.The process according to the invention has not been published so far and is documented by the following example, which in no way excludes the possible variability of the process.
PříkladExample
Do předložených 200 objem, dielov kyseliny dusičnéj 96,1 %-nej s obsahom 0,3 % hmot. analytickej kyseliny dusitej, ochladenej na 18 až 20 °C, je za miešania a chladenia vnášaných 20 hmot. dielov nitrovanej substancie, t. j. tetrahydroimidazo[4,5-djimidazól-2,5(lH,3H)-diónu, tak, aby teplota reakčnej zmesi bola 23 až 25 °C. Potom je reakčná zmes za miešania vyhriatá na teplotu 63 až 66 °C a na nej je udržiavaná 35 minút. Nitrácia je ukončená naliatím reakčnej zmesi do 1000 objem, dielov 65 až 70 °C teplej vody, rezultujúca suspenzia je 30 minút miešaná a po ochladení na teplotu 24 až 20 °C filtrovaná.Up to the present 200 volumes of 96.1% nitric acid containing 0.3 wt. of analytical nitric acid, cooled to 18-20 ° C, is added with stirring and cooling, 20 wt. parts of the nitrated substance, i. j. tetrahydroimidazo [4,5-djimidazol-2,5 (1H, 3H) -dione, so that the temperature of the reaction mixture was 23-25 ° C. The reaction mixture is then heated to 63-66 ° C with stirring for 35 minutes. The nitration is terminated by pouring the reaction mixture into 1000 volumes, parts 65-70 ° C warm water, the resulting suspension is stirred for 30 minutes and filtered after cooling to 24-20 ° C.
Filtračný koláč je po páťnásobnom premytí á 20 objem, dielami vody sušený 2 hod, pri 90 °C. Z tohto základného postupu rezultuje 24,5 hmot. dielov 1,4-dinitrotetrahydroimidazo [4,5-d]imidazól-2,5-(1H,3H)-diónu, kódovo označovaného DINGU, čo je 75 %-ný výťažok oproti teorii.The filter cake is dried at 90 ° C for 2 hours after washing five times with 20 volumes of part water. This basic procedure results in 24.5 wt. parts of 1,4-dinitrotetrahydroimidazo [4,5-d] imidazol-2,5- (1H, 3H) -dione, code-named DINGU, is a 75% yield over theory.
Uvedený základný postup je opakovaný s aplikáciou východiskovej substancie s obsahom 0,299 °/o hmot. dusičnanu močoviny (to je 0,3 % hmot. na návažok nitrovanej substancie) a potom je opakovaný s tým, že před započatím vnášania východiskové) substancie do reakčného systému je v predloženej kyselme dusičnej rozpuštěných 4 hmot. dielov dusičnanu močoviny (to je 20 % hmot. na návažok nitrovanej substancie). V prvom případe rezultuje 25,7 hmot. dielov DINGU (t. j. 78,7 % oproti teorii), v druhom 27,0 hmot. dielov DINGU (t. j. 82,65 percent oproti teorii).Said basic procedure is repeated with the application of a starting substance containing 0.299% w / w. urea nitrate (i.e. 0.3 wt.% per weight of nitrated substance) and then repeated, with 4 wt.% dissolved in the present nitric acid prior to introduction of the starting substance into the reaction system. parts of urea nitrate (i.e., 20% by weight of the nitrated substance). In the first case, 25.7 wt. parts of DING (i.e. 78.7% vs. theory), in the second 27.0 wt. parts of DING (i.e., 82.65 percent versus theory).
Pomocou neizotermickej diferenčnej termickej analýzy, pracujúcej s rýchlosťou lineárneho vzostupu teploty 5 °C . min-1·, meriacím rozsahom 1 mV na škálu stupnice a navážkami 80 až 90 mg vzorky boli nájdené počiatky exotermického rozkladu u DINGU z nitrácie bez aditíva pri 149,9 °C, u DINGU z nitrácie s aditívom 0,3 % hmot. pri 151,1 stupňoch C a u DINGU z nitrácie s 20 % hmot. additíva pri 154,9 °C.Using a non-isothermal differential thermal analysis operating at a linear temperature rise rate of 5 ° C. min -1 ·, with a measuring range of 1 mV per scale and weighing 80-90 mg of the sample, the foundations of exothermic decomposition were found in DING from nitration without additive at 149.9 ° C, in DING from nitration with additive 0.3 wt. at 151.1 degrees C and DING from nitration with 20 wt. additive at 154.9 ° C.
PREDMETSUBJECT
Sposob výroby dinitrotetrahydroimidazo[ 4,5-d ] imidazól-2,5 (1H,3H)-diónu nitráciou tetrahydroimidazo [ 4,5-d ] imidazól-2,5 {1H3Hj-diónu kyselinou dusičnou, vyznačujúci sa tým, že ,sa v procese výroby přidá do re-A method for producing dinitrotetrahydroimidazo [4,5-d] imidazol-2,5 (1H, 3H) -dione by nitration of tetrahydroimidazo [4,5-d] imidazol-2,5 (1H, 3H) -dione by nitric acid, characterized in that in the production process
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS736083A CS235587B1 (en) | 1983-10-07 | 1983-10-07 | Method of polyvinyl chloride plastificing |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS736083A CS235587B1 (en) | 1983-10-07 | 1983-10-07 | Method of polyvinyl chloride plastificing |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS235587B1 true CS235587B1 (en) | 1985-05-15 |
Family
ID=5422605
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS736083A CS235587B1 (en) | 1983-10-07 | 1983-10-07 | Method of polyvinyl chloride plastificing |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS235587B1 (en) |
-
1983
- 1983-10-07 CS CS736083A patent/CS235587B1/en unknown
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