| Identification | More | [Name]
Adipic dihydrazide | [CAS]
1071-93-8 | [Synonyms]
ADH
ADIPIC ACID DIHYDRAZIDE
ADIPIC ACID DIHYDRIZIDE
ADIPIC DIHYDRAZIDE
ADIPINIC DIHYDRAZIDE
ADIPODIHYDRAZIDE
Adipohydrazide
adipoyl hydrazide
ADIPYL HYDRAZIDE
AKOS BBS-00001039
HEXANEDIHYDRAZIDE
HEXANEDIOHYDRAZIDE
HEXANEDIOIC ACID, DIHYDRAZIDE
ZERENEX ZX005030
403
Adipic acid dihyrazide
AdipicDihydrazide(Adh)
Adipic dihydrazide (Adipic acid dihydrazide), 98%
1,4-butanedicarboxylic dihydrazide
hexanedioic dihydrazide | [EINECS(EC#)]
213-999-5 | [Molecular Formula]
C6H14N4O2 | [MDL Number]
MFCD00007614 | [Molecular Weight]
174.2 | [MOL File]
1071-93-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white to slightly yellow crystalline powder | [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) | [Fp ]
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]
1071-93-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [RTECS ]
AV1400000 | [Autoignition Temperature]
360 °C | [Hazard Note ]
Irritant | [TSCA ]
Yes | [HazardClass ]
IRRITANT | [HS Code ]
29280090 |
| Hazard Information | Back Directory | [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. | [Application]
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]
Nonflammable | [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 |
|
|