Adipic dihydrazide Chemical Properties

Melting point:

180-182 °C (lit.)

Boiling point:

305.18°C (rough estimate)

Density 

1.2297 (rough estimate)

vapor pressure 

0Pa at 25℃

refractive index 

1.6700 (estimate)

Flash point:

150 °C

storage temp. 

-20°C

solubility 

H₂O: 100 mg/mL

form 

Crystalline Powder

pka

12.93±0.35(Predicted)

color 

White to slightly yellow

Water Solubility 

soluble

BRN 

973863

InChIKey

IBVAQQYNSHJXBV-UHFFFAOYSA-N

LogP

-2.7 at 20℃

CAS DataBase Reference

1071-93-8(CAS DataBase Reference)

NIST Chemistry Reference

Adipic dihydrazide(1071-93-8)

EPA Substance Registry System

Hexanedioic acid, dihydrazide (1071-93-8)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

AV1400000

Autoignition Temperature

360 °C

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29280090

MSDS

• Language:English Provider:Hexanedioic acid dihydrazide
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Adipic dihydrazide Usage And Synthesis

Description

Adipic dihydrazide (ADH) is the most suitable hydrazide cross-linking agent, and ADH has been widely used in water-based paint emulsions in combination with diacetone acrylamide. ADH is weakly alkaline, and there is a possibility of agglomeration when solid ADH is added directly to the emulsion, so usually ADH should be dissolved in hot water before use.

Chemical Properties

white to slightly yellow crystalline powder

Uses

Adipic dihydrazide is used as a formaldehyde scavenger and reacts with formaldehyde, thereby preventing the volatilizing of formaldehyde in the air. It is also employed as a paint additive and coating additive. It is also used as an intermediate. Further, it is used for cross-linking water-based emulsions and as a hardener for certain epoxy resins, which finds application in powder coating.

Uses

Adipic acid dihydrazide is a homobifunctional cross-linking reagent specific for aldehydes resulting in relatively stable hydrazone linkages. Adipic acid dihydrazide is typically, used in the linking of glycoproteins, such as antibodies, in a site specific fashion following periodate oxidation. Oxidation and coupling may conveniently be performed at pH 5.0 due to the low pKa of the hydrazide which avoids competition by primary amines.

Flammability and Explosibility

Non flammable

reaction suitability

reagent type: cross-linking reagent

Synthesis

General method: 7.6 g (100.0 mmol) of solid hydrazine (H3N + NHCO2-) was mixed with adipic acid (7.3 g, 50.0 mmol) in a mortar and pestle under solvent-free conditions for 10 min, followed by a stirring reaction for 5 h at 100 °C. The structure and composition of the reaction products were confirmed by 400 MHz NMR (nuclear magnetic resonance) and elemental analysis. The analysis showed that the product was hexanedihydrazide (C6H14N4O2) with ≥96% conversion and ≥95% yield (8.27 g). Alternative method: 10 g of decane was used as solvent and the reaction conditions were adjusted to stirring at 110 °C for 12 h, followed by filtration and separation operations. The rest of the steps were the same as in the generalized method. The product was analyzed as hexanedihydrazide (C6H14N4O2) with 97% conversion and 93% yield. Substitution: 5.0 g (100.0 mmol) of hydrazine hydrate was used in place of the solid hydrazine and 10.12 g (100.0 mmol) of diethyl adipate was used in place of adipic acid. The reaction was stirred at 75 °C for 5 h under the condition of 10 g ethanol as solvent. The product was analyzed as hexanedihydrazide (C6H14N4O2) with 89% conversion and 83% yield.

References

[1] Patent: KR2015/88523, 2015, A. Location in patent: Paragraph 0128; 0137; 0148-0149
[2] Organic Syntheses, 1956, vol. 36, p. 72,Note 7
[3] Justus Liebigs Annalen der Chemie, 1929, vol. 475, p. 122
[4] Journal fuer Praktische Chemie (Leipzig), 1915, vol. <2> 91, p. 23
[5] Journal fuer Praktische Chemie (Leipzig), 1981, vol. 323, # 3, p. 360 - 366

Adipic dihydrazide(1071-93-8)Related Product Information

• Adipic acid
• Folic acid
• Butanedihydrazide
• METHOXYFENOZIDE
• Maleic hydrazide
• Tebufenozide
• Hyaluronic acid
• Oxalyl dihydrazide
• Ethyl 2-(Chlorosulfonyl)acetate
• DIPHENYLCARBAZONE
• Decanedihydrazide
• 1,5-Diphenylcarbazide
• Carbohydrazide
• Dimethyl adipate
• antioxidant 1024
• Citric acid
• Ascoric Acid
• Adipic dihydrazide
• Adipic Acid Dihydrazide