“Carbohydrazide”的意思、由来-开放百科全书

词条

Carbohydrazide

释义

Production
Structure
Industrial uses
Hazards
References

{{chembox
| Watchedfields = changed
| verifiedrevid = 443499391
| ImageFile = Carbohydrazide.png
| ImageSize = 150px
| ImageAlt = Structural formula
| ImageFile1 = OC(N2H3)2.png
| ImageSize1 = 260
| ImageAlt1 = Ball-and-stick model
| IUPACName=1,3-Diaminourea
| OtherNames=
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 66578
| InChI = 1/CH6N4O/c2-4-1(6)5-3/h2-3H2,(H2,4,5,6)
| InChIKey = XEVRDFDBXJMZFG-UHFFFAOYAS
| SMILES1 = O=C(NN)NN
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/CH6N4O/c2-4-1(6)5-3/h2-3H2,(H2,4,5,6)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XEVRDFDBXJMZFG-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=497-18-7
| PubChem=73948
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 61308
| SMILES=C(=O)(NN)NN
|Section2={{Chembox Properties
| Formula=CH₆N₄O
| MolarMass=90.09 g/mol
| Appearance=
| Density=1.341 g/cm³
| MeltingPtC=153 to 154
| BoilingPt=
| Solubility=
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
}}

Carbohydrazide is the chemical compound with the formula OC(N₂H₃)₂. It is a white, water-soluble solid.^[1]^[2] It decomposes upon melting.^[2] 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.

Production

Industrially the compound is produced by treatment of urea with hydrazine:^[1]

OC(NH₂)₂ + 2 N₂H₄ → OC(N₂H₃)₂ + 2 NH₃

It can also be prepared by reactions of other C1-precursors with hydrazine, such as carbonate esters.^[2]

It can be prepared from phosgene, but this route cogenerates the hydrazinium salt [N₂H₅]Cl and results in some diformylation. Carbazic acid 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.^[2]

Industrial uses

Oxygen scrubber: carbohydrazide is used to remove oxygen in boiler systems. Oxygen scrubbers prevent corrosion.^[7]^[8]
Precursor to polymers: carbohydrazide can be used as a curing agent for epoxide-type resins.^[2]
Photography: carbohyrazide is used in the silver halide diffusion process as one of the toners. Carbohydrazide is used to stabilize color developers that produce images of the azo-methine and azine classes.^[2]
Carbohydrazide has been used to develop ammunition propellants,^[11] stabilize soaps,^[2] and used a reagent in organic synthesis.

Hazards

Heating carbohydrazide may result in an explosion. Carbohydrazide is harmful if swallowed, irritating to eyes, respiratory system, and skin. Carbohydrazide is toxic to aquatic organisms.^[13]

References

^[3]^[4]^[5]^[6]^[7]^[8]{{Hydrazines}}

2 : Cleaning product components|Hydrazides

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