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Carbohydrazide (1,3-Diaminourea) is the chemical compound with the formula OC(N2H3)2.
Carbohydrazide (1,3-Diaminourea) appears as a white solid that is soluble in water, but not in many organic solvents, such as ethanol, ether or benzene.
Carbohydrazide (1,3-Diaminourea) decomposes upon melting.
CAS: 497-18-7
MF: CH6N4O
MW: 90.08
EINECS: 207-837-2
Synonyms
1,3-Diaminomocovina;1,3-diamino-ure;4-amino-semicarbazid;Cabazide;1,3;DIAMINOUREA;Carbohydrazide58%;CHZ Oxygen Scavenger;4;Aminoisosemicarbazide;Carbohydrazide;497-18-7;Carbonic dihydrazide;1,3-Diaminourea;Carbonohydrazide;Carbazide;Carbodihydrazide;Hydrazine, carbonyldi-;Hydrazine, carbonylbis-;Carbazic acid, hydrazide;carbonyl dihydrazine;Semicarbazide, 4-amino-;Carbonic acid, dihydrazide;Cabazide;Karbazid;Hydrazinecarboxamide, N-amino-;Urea, 1,3-diamino-;Urea, N,N'-diamino-;Hydrazinecarboxylic acid, hydrazide;1,3-Diaminomocovina;Carbonohydrazid;carbonodihydrazide;NSC 1934;N,N'-diaminourea;4-aminosemicarbazide;carbonylbis-hydrazine;hydrazinecarbohydrazide;N-aminohydrazinecarboxamide;W8V7FYY4WH;N-aminohydrazine carboxamide;hydrazide hydrazinecarboxylic acid;NSC-1934;Karbazid [Czech];CH6N4O;1,3-Diaminomocovina [Czech];EINECS 207-837-2;UNII-W8V7FYY4WH;BRN 1747069;AI3-52397;carbonyldihydrazide;Urea,3-diamino-;Urea,N'-diamino-;MFCD00007591;Carbohydrazide, 98%;1,3-bis(azanyl)urea;CARBOHYDRAZIDE [MI);EC 207-837-2;4-03-00-00240 (Beilstein Handbook Reference);DTXSID5038757;CHEBI:61308;NSC1934;O C (N H N H2)2;AKOS003193931;DB-029568;CS-0149890;NS00001612;EN300-20051;E77171;A827826;Q5037885;W-106011
A number of carbazides are known where one or more N-H groups are replaced by other substituents.
They occur widely in the drugs, herbicides, plant growth regulators, and dyestuffs.
Carbohydrazide (1,3-Diaminourea) is a white crystalline thin and short columnar crystal or white powder at room temperature.
Carbohydrazide (1,3-Diaminourea) is insoluble in alcohol, easily soluble in water with dissolution absorbing heat.
Carbohydrazide (1,3-Diaminourea) is insoluble in alcohol, ether, and benzene.
Owing to that, Carbohydrazide (1,3-Diaminourea) is a kind of derivative of hydrazine and thus having strong reduction ability.
Carbohydrazide (1,3-Diaminourea) is non-toxic, and can replace hydrazine and oximes.
Carbohydrazide (1,3-Diaminourea) has a broad range of application in industry.
For example, Carbohydrazide (1,3-Diaminourea) can be used as the oxygen scavenging agent of boiler water in the field of water treatment and is regarded as most advanced materials for oxygen scavenging of boiler water.
Carbohydrazide (1,3-Diaminourea) has a low toxicity and high melting point with its deoxidizing efficiency being far greater than the current materials used and is a idea product for both safety and environmental protection; Carbohydrazide (1,3-Diaminourea) can also be used as a rocket propellant components; moreover, owing to that its hydrogen atoms attached to the nitrogen atom is easily substituted by other groups, Carbohydrazide (1,3-Diaminourea) can be used as the cross-linking agents of elastic fibers in the textile field, the formaldehyde scavenger, as well as the antioxidant of carotene pigment.
In addition, adding an appropriate amount of Carbohydrazide (1,3-Diaminourea) to the phenol fungicides containing can play a role on preventing discoloration and rancidity.
As a chemical raw material and chemical industry intermediates, Carbohydrazide (1,3-Diaminourea) is widely used in medicine, herbicides, plant growth regulators, dyes and other industries.
When acting as the oxygen scavenger of boiler water, Carbohydrazide (1,3-Diaminourea) may be directly added into the water while its aqueous solution can also be used.
The usage amount of Carbohydrazide (1,3-Diaminourea) for scavenging 1mol O2 is 0.5mol, and should be appropriately in excess.
The proper temperature range is 87.8-176.7 ℃.
The optimal time for applying Carbohydrazide (1,3-Diaminourea) is after the thermal scavenging of oxygen.
The reaction of oxygen and Carbohydrazide (1,3-Diaminourea) is as follows: CON4H6 + 2O2 = 2N2 + 3H2O + CO2
A Carbohydrazide (1,3-Diaminourea) obtained by formal condensation between hydrazinecarboxylic acid and hydrazine.
Carbohydrazide (1,3-Diaminourea) is white crystal powder. Carbohydrazide is very soluble in water and soluble in alcohol.
Carbohydrazide (1,3-Diaminourea) on heating or exposure to uv to form ammonia, hydrogen, and nitrogen, which may be explosive with a blue flame when catalyzed by metal oxides and some metals such as platinum or raney nickel.
Carbohydrazide (1,3-Diaminourea) has dibasic and very reactive properties. Carbohydrazide is used as a component in jet fuels because it produce a large amount of heat when burned.
Carbohydrazide (1,3-Diaminourea) is used as rocket fuel.
Carbohydrazide (1,3-Diaminourea) is used as an oxygen scavenger for water boiler feed and heating systems to prevent corrosion damage.
Carbohydrazide (1,3-Diaminourea) is used as a reducing agent for the recovery of precious metals.
Carbohydrazide (1,3-Diaminourea) is used as a polymerization catalyst and a chain extender in urethane coatings.
Carbohydrazide (1,3-Diaminourea) is used as an auxiliary in photographic industry to prevent discolouration.
Carbohydrazide (1,3-Diaminourea) is used as an intermediate for pharmaceuticals, stabilizers and water treatment chemicals.
Carbohydrazide (1,3-Diaminourea) and its derivatives are versatile intermediates.
They have active applications in organic synthesis for agrochemicals, pharmaceuticals, photographic, heat stabilizers, polymerization catalysts, flame- retardants, blowing agents for plastics, explosives, and dyes.
Recently, hydrazine is applied to lcd (liquid crystal displays) as the fuel to make faster thin-film transistors.
Carbohydrazide (1,3-Diaminourea) Chemical Properties
Melting point: 150-153 °C (lit.)
Boiling point: 167.26°C (rough estimate)
Density: 1.02
Vapor pressure: 0Pa at 25℃
Refractive index: 1.4164 (estimate)
Storage temp.: Keep in dark place,Inert atmosphere,2-8°C
Solubility: DMSO (Slightly), Water (Slightly)
pka: 11.81±0.20(Predicted)
Form: Crystalline Powder
Color: White
Water Solubility: Soluble in water.
Merck: 14,1804
BRN: 1747069
Stability: Stable, but may explode if heated.
Incompatible with strong acids, strong oxidizing agents.
InChIKey: XEVRDFDBXJMZFG-UHFFFAOYSA-N
LogP: -2.94 at 21.6℃
CAS DataBase Reference: 497-18-7(CAS DataBase Reference)
NIST Chemistry Reference: Carbohydrazide (1,3-Diaminourea)(497-18-7)
EPA Substance Registry System: Carbohydrazide (497-18-7)
Carbohydrazide (1,3-Diaminourea) is also known as carbazide, 1,3-disemicarbazide, Carbohydrazide (1,3-Diaminourea), white fine short columnar crystals or white crystalline powder at room temperature, insoluble in ethanol, easily soluble in water, soluble in endotherm, insoluble in alcohol, ether, benzene, because Carbohydrazide (1,3-Diaminourea) is a derivative of hydrazine, it has strong reducibility, non-toxic, and can replace hydrazine hydrate and oxime.
Carbohydrazide (1,3-Diaminourea) has a wide range of uses in industry.
Carbohydrazide (1,3-Diaminourea) can be used as a deoxidizer for boiler water in the field of water treatment.
Carbohydrazide (1,3-Diaminourea) is the most advanced material used for deoxidizing boiler water in the world today.
Carbohydrazide (1,3-Diaminourea) has low toxicity, high melting point, and far greater deoxidizing efficiency.
The material used is an ideal safe and environmentally friendly product; Carbohydrazide (1,3-Diaminourea) can also be used as a component of rocket propellant; and because the hydrogen atom connected to the nitrogen atom is easily replaced by other groups, in the textile industry, Carbohydrazide (1,3-Diaminourea) can also be used as a crosslinking agent for elastic fibers, a trap for formaldehyde, and an antioxidant for pigments such as carotene.
In addition, adding an appropriate amount of Carbohydrazide (1,3-Diaminourea) to the soap containing phenol fungicides can prevent discoloration and rancidity.
As chemical raw materials and chemical intermediates, Carbohydrazide (1,3-Diaminourea) is widely used in medicine, herbicides, plant growth regulators, dyes and other industries.
Uses
Carbohydrazide (1,3-Diaminourea) is widely used in the production of pharmaceuticals, herbicides, plant growth regulators, dyes, etc.
(1) carbohydrazide is a derivative of hydrazine with a strong reduction.
Carbohydrazide (1,3-Diaminourea) can be not only used as the intermediates for producing energy-containing materials, but also can be used directly as the components of explosives and propellants.
(2) Carbohydrazide (1,3-Diaminourea) can be used as the preservative of refinery equipment and can also be used as the oxygen scavenger of boiler water treatment agent.
(3) Carbohydrazide (1,3-Diaminourea) can be used as the cross-linking agent of the elastic fiber in the field of chemical fiber industry.
(4) Carbohydrazide (1,3-Diaminourea) can be used as the chemical raw materials and chemical industrial intermediates and is widely used in medicine, herbicides, plant growth regulators, dyes and other industries.
Carbohydrazide (1,3-Diaminourea) can be used as the component of the rocket propellant, the stabilizer of color development and soap quality, the antioxidants of rubber, the oxygen scavenger of boiler water, and the passivation agent of metal.
Carbohydrazide (1,3-Diaminourea) is a derivative of hydrazine with a strong reduction.
Carbohydrazide (1,3-Diaminourea) can be used as the intermediate of producing energy-containing materials and also be used directly for the components of explosives and rocket propellant.
Carbohydrazide (1,3-Diaminourea) can also be used as the oxygen scavenger of boiler water and is the most advanced materials for scavenging oxygen of boiler water in the world today.
Carbohydrazide (1,3-Diaminourea) has low toxicity, high melting point and a deoxidation efficiency being far greater than the materials currently used.
Carbohydrazide (1,3-Diaminourea) is an ideal product for both safety and environmental protection.
In addition, Carbohydrazide (1,3-Diaminourea) can be used as the cross-linking agent of the elastic fiber in the field of chemical fiber industry.
Carbohydrazide (1,3-Diaminourea) can also be used as the chemical raw materials and chemical industrial intermediates and is widely used in medicine, herbicides, plant growth regulators, dyes and other industries.
Carbohydrazide (1,3-Diaminourea) is widely utilized as a curing agent for epoxide-type resins and as an oxygen scrubber in boiler systems.
Carbohydrazide (1,3-Diaminourea) is applied in photography to stabilize color developers that produce images of the azo-methine and azine classes.
Carbohydrazide (1,3-Diaminourea) is used to develop ammunition propellants and stabilize soaps.
Carbohydrazide (1,3-Diaminourea) is also a useful reagent in organic synthesis.
Widely used in the production of drugs, herbicides, plant growth regulators, dyes, etc.
(1) Carbohydrazide (1,3-Diaminourea) is a derivative of hydrazine, which has strong reducibility and can be used as an intermediate in the manufacture of energetic materials, and can also be directly used as a component of explosives and propellants.
(2) refinery equipment preservatives, can be used as boiler water treatment agent oxygen scavenger.
(3) the chemical fiber industry as a cross-linking agent for elastic fibers.
(4) as chemical raw materials and chemical intermediates, Carbohydrazide (1,3-Diaminourea) is widely used in medicine, herbicides, plant growth regulators, dyes and other industries.
Industrial uses
Oxygen scrubber: Carbohydrazide (1,3-Diaminourea) is used to remove oxygen in boiler systems.
Oxygen scrubbers prevent corrosion.
Precursor to polymers: Carbohydrazide (1,3-Diaminourea) can be used as a curing agent for epoxide-type resins.
Photography: carbohydrazide is used in the silver halide diffusion process as one of the toners.
Carbohydrazide (1,3-Diaminourea) is used to stabilize color developers that produce images of the azo-methine and azine classes.
Jet fuel: Carbohydrazide (1,3-Diaminourea) can be used as a component in jet fuels, as a large amount of heat is being produced when the material is burned.
Carbohydrazide (1,3-Diaminourea) has been used to develop ammunition propellants, stabilize soaps, and is used as a reagent in organic synthesis.
Salts of Carbohydrazide (1,3-Diaminourea), such as nitrate, dinitrate and perchlorate, can be used as secondary explosives.
Complex salts of Carbohydrazide (1,3-Diaminourea), like bis(carbohydrazide)diperchloratocopper(II) and tris(carbohydrazide)nickel(II) perchlorate, can be used as primary explosives in laser detonators.
Production
Industrially Carbohydrazide (1,3-Diaminourea) is produced by treatment of urea with hydrazine:
OC(NH2)2 + 2 N2H4 → OC(N2H3)2 + 2 NH3
Carbohydrazide (1,3-Diaminourea) can also be prepared by reactions of other C1-precursors with hydrazine, such as carbonate esters.
Carbohydrazide (1,3-Diaminourea) can be prepared from phosgene, but this route cogenerates the hydrazinium salt [N2H5]Cl and results in some diformylation.
Carbohydrazide (1,3-Diaminourea) is also a suitable precursor:
N2NH3CO2H + N2H4 → OC(N2H3)2 + H2O
Structure
The molecule is nonplanar.
All nitrogen centers are at least somewhat pyramidal, indicative of weaker C-N pi-bonding.
The C-N and C-O distances are about 1.36 and 1.25 Å, respectively.
Production Method
1.354g of diethyl carbonate (3.0mol) and 388g of 85% hydrazine hydrate (6.6mol) are mixed in one step and placed in a 1L round bottom flask (with thermometer).
At the beginning, there is only partial mutual dissolution, shaking the flask until the contents become a single phase.
The reaction in the bottle is as follows: heat is released during the reaction, which makes the temperature rise to about 55 ℃.
Then connect the flask to the fractionation column with a standard sleeve joint.
The fractionation column is filled with Raschig ring.
The thickness of the filler layer is 22cm.
A thermometer is inserted into the column with a water-cooled condenser.
A heating electric furnace with a pressure regulator was used to heat the reaction mixture.
Within 30min after the start of the reaction, the generated ethanol and water are rapidly evaporated, and the subsequent distillate rate slows down.
Continuous heating for 4 hours, distillate 325~350ml of distillate (temperature 85~96 ℃).
The temperature in the bottle rose from 96 ℃ to 119 ℃.
Cool the liquid in the bottle to 20 ℃ and let it stand for at least 1h.
The precipitated carbonyl hydrazide crystals are filtered and separated, and the wet separation is drained as much as possible.
The prepared crude product is about 165g with 60% yield.
If refining is required, Carbohydrazide (1,3-Diaminourea) can be processed by recrystallization and the refined product can be washed with ether.
2. Semi-continuous method This method is an improvement of one-step method.
The mother liquor after crystallization is recycled and some new raw materials are added, thus significantly improving the yield.
The reaction and the separation of volatile products are still carried out with the device in the one-step process.
The method is briefly described as follows: 856g diethyl carbonate 7.25mol) and 938g 85% hydrated 15.95mol) are shaken and mixed into a single phase liquid to prepare a raw material liquid.
In the initial stage of synthesis, 700g of raw material liquid is taken, fractionation is carried out under the above conditions, alcohol and water mixture (liquid) is distilled, and heating is continued to 119 ℃.
The reaction mixture is cooled and filtered to recover the resulting crude Carbohydrazide (1,3-Diaminourea) product.
Weigh the separated mother liquor, add fresh raw liquid to 700g, and recycle.
The cumulative yield reached 87%.
3. Other preparation methods from urea and excess hydrazine reaction.
Hydrazine reacts with carbonyl chloride (phosgene).
The mixture of isocyanuric acid and hydrazine hydrate was heated and refluxed for 17h to obtain carbonyl hydrazide, and the yield reached 7 1%.
