SE519778C2 - Methods of preparing nitroform - Google Patents
Methods of preparing nitroformInfo
- Publication number
- SE519778C2 SE519778C2 SE0102908A SE0102908A SE519778C2 SE 519778 C2 SE519778 C2 SE 519778C2 SE 0102908 A SE0102908 A SE 0102908A SE 0102908 A SE0102908 A SE 0102908A SE 519778 C2 SE519778 C2 SE 519778C2
- Authority
- SE
- Sweden
- Prior art keywords
- nitroform
- gem
- nitration
- process according
- group
- Prior art date
Links
- LZGVDNRJCGPNDS-UHFFFAOYSA-N trinitromethane Chemical compound [O-][N+](=O)C([N+]([O-])=O)[N+]([O-])=O LZGVDNRJCGPNDS-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims abstract description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000006396 nitration reaction Methods 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 7
- 239000007858 starting material Substances 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 6
- 230000000802 nitrating effect Effects 0.000 claims abstract description 6
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000002823 nitrates Chemical class 0.000 claims abstract description 3
- 239000000725 suspension Substances 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 125000003277 amino group Chemical group 0.000 claims abstract 2
- -1 and c) 4 Chemical compound 0.000 claims abstract 2
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentaoxide Chemical compound [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 3
- XKVYZLLWKHGKMT-BEJOYRPXSA-N Gemin D Natural products O([C@@H]([C@@H](O)C=O)[C@@H]1[C@@H](O)COC(=O)c2c(c(O)c(O)c(O)c2)-c2c(O)c(O)c(O)cc2C(=O)O1)C(=O)c1cc(O)c(O)c(O)c1 XKVYZLLWKHGKMT-BEJOYRPXSA-N 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 229930192479 gemin Natural products 0.000 claims description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 abstract description 3
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 abstract 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 abstract 1
- BNWWVDSJQIMCTH-UHFFFAOYSA-N trinitromethane Chemical compound [O-][N+](=O)C([N+]([O-])=O)[N+]([O-])=O.[O-][N+](=O)C([N+]([O-])=O)[N+]([O-])=O BNWWVDSJQIMCTH-UHFFFAOYSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- NZEJYBQBDZDVIW-UHFFFAOYSA-N n-carbamoyl-2,2-dinitroacetamide Chemical compound NC(=O)NC(=O)C([N+]([O-])=O)[N+]([O-])=O NZEJYBQBDZDVIW-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- 238000005121 nitriding Methods 0.000 description 2
- ARBJJQGHSYOQCI-UHFFFAOYSA-N potassium;trinitromethane Chemical compound [K+].[O-][N+](=O)[C-]([N+]([O-])=O)[N+]([O-])=O ARBJJQGHSYOQCI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- AUFJTVGCSJNQIF-UHFFFAOYSA-N 2-Amino-4,6-dihydroxypyrimidine Chemical compound NC1=NC(O)=CC(=O)N1 AUFJTVGCSJNQIF-UHFFFAOYSA-N 0.000 description 1
- DUFGYCAXVIUXIP-UHFFFAOYSA-N 4,6-dihydroxypyrimidine Chemical compound OC1=CC(O)=NC=N1 DUFGYCAXVIUXIP-UHFFFAOYSA-N 0.000 description 1
- FFHNABRYKXBJEF-UHFFFAOYSA-N 5,5-dinitro-1,3-diazinane-2,4,6-trione Chemical compound [O-][N+](=O)C1([N+]([O-])=O)C(=O)NC(=O)NC1=O FFHNABRYKXBJEF-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FEWWJLXOPDPPHU-UHFFFAOYSA-N n-carbamoyl-2,2-dinitroacetamide;potassium Chemical compound [K].NC(=O)NC(=O)C([N+]([O-])=O)[N+]([O-])=O FEWWJLXOPDPPHU-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
25 30 35 519 778 3) 4,6-hydroxypyrimidin. 5 30 35 519 778 3) 4,6-hydroxypyrimidine.
Vid nitreringen sätts ett nitrermedel bestående av salpetersyra, nitratsalter eller kvävepentoxid till svavelsyralösningen/suspensionen. Nitreringen blir på detta sätt lätt att styra. Startmaterialet tillförs vid nitreringen ytterligare nitrogrupper och bildar en gem-trinitroförening, som genom hydrolys avspjälkar nitrofonn. Nitreringen genomförs vid en temperatur av från -10°C till +80°C, företrädesvis från +10°C till +60°C. Svavelsyran kan ha en koncentration av 70-100 %, företrädesvis ca 95% Salpetersyran, som är det föredragna nitrermedlet, tillsätts som koncentrerad syra, särskilt med en koncentration av 85-100%. Det molära förhållandet mellan nitrer- medel och substrat kan vara 2,0-6,0:1, och är företrädesvis 3,0-4,0:1. Goda utbyten har erhållits med ett så lågt molärl förhållande som 3,0:1, vilket i kombination med en återanvändning av svavelsyran, som nämns nedan, gör metoden ekonomiskt attraktiv. Nitreringen kan utföras i en vanlig rostfri reaktor utan speciella arrange- mang.During the nitration, a nitrating agent consisting of nitric acid, nitrate salts or nitric oxide is added to the sulfuric acid solution / suspension. In this way, the nitriding becomes easy to control. During the nitration, additional nitro groups are added to the nitration and form a gemin trinitro compound, which cleaves nitrophone by hydrolysis. The nitration is carried out at a temperature of from -10 ° C to + 80 ° C, preferably from + 10 ° C to + 60 ° C. The sulfuric acid may have a concentration of 70-100%, preferably about 95% The nitric acid, which is the preferred nitrating agent, is added as concentrated acid, especially with a concentration of 85-100%. The molar ratio of nitrating agent to substrate may be 2.0-6.0: 1, and is preferably 3.0-4.0: 1. Good yields have been obtained with a molar ratio as low as 3.0: 1, which in combination with a reuse of the sulfuric acid, mentioned below, makes the method economically attractive. The nitriding can be carried out in an ordinary stainless steel reactor without special arrangements.
Efter slutförd nitrering hydrolyseras produkten (gem-trinitroföreningen) för avspjäl- kande av nitroform genom att reaktionsblandningen blandas med ett vattenhaltigt medium, t.ex. slås på krossad is, späds med vatten eller dyl. Bildad nitroform kan extraheras från reaktionsblandningen med ett polärt extraktionsmedel som är stabilt i den aktuella miljön, t.ex. metylenklorid eller dietyleter. Ett neutraliseringsmedel kan därefter tillsättas för att fälla ut motsvarande salt av nitroform. Det är även möjligt att direkt från nitreringsblandningen extrahera den primärt bildade gem-trinitroföre- ningen och därefter hydrolysera denna för avspjälkande av nitroform, t.ex. genom tillsats av en bas. Svavelsyran kan då användas flera gånger Startmaterialet enligt a) ovan kan framställas genom nitrering av barbitursyra till gem-5,5-dinitrobarbitursyra, som därefter hydrolyseras med vatten för att ge gem- dinitroacetylurea eller behandlas med en ringöppnande nukleofil, t.ex. ammoniak, metanol, etanol, isopropanol eller en amin, för att ge substituerad gem-dinitro- acetylurea. Detta beskrivs i Langlet et al.: Synthesis and reactions of 5,5-dinitro- barbituric acid, Conference Proceedings, XlX:th European Colloquium on Hetero- cyclic Chemistry, Aveiro Portugal, July 19-22, 2000, p. A-70. Startmaterialet enligt b) ovan kan på motsvarande sätt framställas genom nitrering av 2-amino-4,6-di- hydroxypyrimidin följt av hydrolys med vatten, såsom beskrivs i Latypov et al.: A new convenient route to gem-dinitroalifatic compounds, Conference Proceedings, 10 15 20 25 30 519 778 3 31st International Conference of ICT: 2000. Startmaterialet enligt c) är en kommersiellt tillgänglig produkt.After completion of nitration, the product (gem-trinitro compound) is hydrolyzed to decompose nitroform by mixing the reaction mixture with an aqueous medium, e.g. beaten on crushed ice, diluted with water or the like. The nitroform formed can be extracted from the reaction mixture with a polar extractant which is stable in the actual environment, e.g. methylene chloride or diethyl ether. A neutralizing agent may then be added to precipitate the corresponding nitroform salt. It is also possible to extract directly from the nitration mixture the primarily formed gemtrinitro compound and then hydrolyze it to cleave nitroform, e.g. by adding a base. The sulfuric acid can then be used fl times The starting material according to a) above can be prepared by nitration of barbituric acid to gem-5,5-dinitrobarbituric acid, which is then hydrolyzed with water to give gem-dinitroacetylurea or treated with a ring-opening nucleophile, e.g. ammonia, methanol, ethanol, isopropanol or an amine, to give substituted gem-dinitroacetylurea. This is described in Langlet et al .: Synthesis and reactions of 5,5-dinitro-barbituric acid, Conference Proceedings, XlX: th European Colloquium on Heterocyclic Chemistry, Aveiro Portugal, July 19-22, 2000, p. A-70 . The starting material according to b) above can be similarly prepared by nitration of 2-amino-4,6-dihydroxypyrimidine followed by hydrolysis with water, as described in Latypov et al .: A new convenient route to gem-dinitroaliphatic compounds, Conference Proceedings , 10 15 20 25 30 519 778 3 31st International Conference of ICT: 2000. The starting material according to c) is a commercially available product.
Uppfinningen skall i det följande belysas med exempel.The invention will be illustrated by examples below.
Exempel 1 Kaliumdinitroacetylurea (6,8 g) löstes i svavelsyra (20 ml, 95% koncentration). Kon- centrerad salpetersyra (1,4 ml) tillsattes droppvis. Temperaturen höjdes till ca. 40°C under en timme. Reaktionsblandningen hälldes på 60g krossad is och extraherades därefter med 2x50 ml dietyleter. Eterfasen torkades med natriumsulfat. Kaliumhyd- roxid löst i etanol tillsattes. En gul fällning av kaliumnitroform (4,6 g; 68% utbyte) erhölls.Example 1 Potassium dinitroacetylurea (6.8 g) was dissolved in sulfuric acid (20 ml, 95% concentration). Concentrated nitric acid (1.4 ml) was added dropwise. The temperature was raised to approx. 40 ° C for one hour. The reaction mixture was poured onto 60g of crushed ice and then extracted with 2x50 ml of diethyl ether. The ether phase was dried over sodium sulfate. Potassium hydroxide dissolved in ethanol was added. A yellow precipitate of potassium nitroform (4.6 g; 68% yield) was obtained.
Exempel 2. 4,6-dihydroxypyrimidin (4g) löstes i svavelsyra (20ml, 95% konc.). Rykande salpetersyra tillsattes (6ml) under kylning med is och hölls därefter vid rumstempe- ratur under 12 timmar. Reaktionsblandningen hälldes på krossad is och extrahera- des med metylenklorid. Utbyte av nítroform 60%, mätt med UV-spektroskopi i metylenklorid.Example 2. 4,6-Dihydroxypyrimidine (4g) was dissolved in sulfuric acid (20ml, 95% conc.). Fuming nitric acid was added (6ml) while cooling with ice and then kept at room temperature for 12 hours. The reaction mixture was poured onto crushed ice and extracted with methylene chloride. Yield of nitroform 60%, measured by UV spectroscopy in methylene chloride.
Exempel 3.Example 3.
Dinitroacetylurea (Bg) löstes i svavelsyra (20ml, 95% konc.). Koncentrerad salpeter- syra (0,57ml) tillsattes. Reaktionsblandningen stod under omröming i en timme vid 20°C. Därefter hälldes den på 74 g krossad is, värmdes till 50°C i 10 minuter och extraherades med 2x125 ml metylenklorid. Utbyte av nítroform 62%.Dinitroacetylurea (Bg) was dissolved in sulfuric acid (20ml, 95% conc.). Concentrated nitric acid (0.57 ml) was added. The reaction mixture was stirred for one hour at 20 ° C. It was then poured onto 74 g of crushed ice, heated to 50 ° C for 10 minutes and extracted with 2x125 ml of methylene chloride. Yield of nitroform 62%.
Exempel 4.Example 4.
Dinitroacetylurea (3 g) löstes i svavelsyra (20ml, 95% konc.). Koncentrerad salpe- tersyra (0,57 ml) tillsattes. Reaktionsblandningen stod under omrörning i en timme vid 20°C med ett lock (täckande skikt) bestående av 30 ml metylenklorid. Metylen- kloriden avskiljdes från reaktionsblandningen och blandades med 30 ml n-heptan.Dinitroacetylurea (3 g) was dissolved in sulfuric acid (20ml, 95% conc.). Concentrated nitric acid (0.57 ml) was added. The reaction mixture was stirred for one hour at 20 ° C with a lid (covering layer) consisting of 30 ml of methylene chloride. The methylene chloride was separated from the reaction mixture and mixed with 30 ml of n-heptane.
Blandningen indunstades till 20 ml då trinitroacetylurea föll ut. Trinitroacetylurean kunde nu lätt 'nydroiyseras med kaiiumhydroxid för avspjäikande av kaliumnitroform.The mixture was evaporated to 20 ml when trinitroacetylurea precipitated. The trinitroacetylurea could now be easily redoxylated with potassium hydroxide to remove potassium nitroform.
Claims (6)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0102908A SE519778C2 (en) | 2001-08-31 | 2001-08-31 | Methods of preparing nitroform |
| PCT/SE2002/001551 WO2003018514A1 (en) | 2001-08-31 | 2002-08-30 | Method of preparing nitroform |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0102908A SE519778C2 (en) | 2001-08-31 | 2001-08-31 | Methods of preparing nitroform |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE0102908D0 SE0102908D0 (en) | 2001-08-31 |
| SE0102908L SE0102908L (en) | 2003-03-01 |
| SE519778C2 true SE519778C2 (en) | 2003-04-08 |
Family
ID=20285198
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE0102908A SE519778C2 (en) | 2001-08-31 | 2001-08-31 | Methods of preparing nitroform |
Country Status (2)
| Country | Link |
|---|---|
| SE (1) | SE519778C2 (en) |
| WO (1) | WO2003018514A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105111087B (en) * | 2015-08-19 | 2017-05-17 | 南京理工大学 | Trinitroethanol preparation method with improved process safety |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3125606A (en) * | 1964-03-17 | Process for the manufacture of | ||
| US3007960A (en) * | 1958-11-10 | 1961-11-07 | Purdue Research Foundation | N-trinitroalkyl-n-nitroaminoalkyl acids and derivatives thereof |
| US3491160A (en) * | 1968-02-05 | 1970-01-20 | Escambia Chem Corp | Process for producing nitroform |
| US4122124A (en) * | 1977-12-05 | 1978-10-24 | Rockwell International Corporation | Production of trinitromethane |
| AU2724197A (en) * | 1996-04-16 | 1997-11-07 | Arco Chemical Technology L.P. | Reducing tetranitromethane in compositions containing nitroaromatic compounds |
-
2001
- 2001-08-31 SE SE0102908A patent/SE519778C2/en not_active IP Right Cessation
-
2002
- 2002-08-30 WO PCT/SE2002/001551 patent/WO2003018514A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003018514A9 (en) | 2004-04-22 |
| SE0102908D0 (en) | 2001-08-31 |
| SE0102908L (en) | 2003-03-01 |
| WO2003018514A1 (en) | 2003-03-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |