1,8-Diaminooctane Chemical Properties

Melting point:

50-52 °C(lit.)

Boiling point:

225-226 °C(lit.)

Density 

0.98 g/mL at 20 °C

vapor pressure 

<0.1 hPa (20 °C)

refractive index 

1.4618 (estimate)

Flash point:

329 °F

storage temp. 

Store below +30°C.

solubility 

575g/l

form 

Solidified Crystalline Mass

pka

11.00, 10.1(at 20℃)

color 

White to yellow

PH

11.7 (4g/l, H2O, 20℃)

explosive limit

1.1-6.8%(V)

Water Solubility 

575 g/L (20 ºC)

Sensitive 

Hygroscopic

BRN 

1735426

InChIKey

PWGJDPKCLMLPJW-UHFFFAOYSA-N

LogP

0.896 at 25℃

CAS DataBase Reference

373-44-4(CAS DataBase Reference)

NIST Chemistry Reference

1,8-Diaminooctane(373-44-4)

EPA Substance Registry System

1,8-Octanediamine (373-44-4)

Safety Information

Hazard Codes 

C,Xi

Risk Statements 

34-36/37/38

Safety Statements 

26-36/37/39-45-37/39

RIDADR 

UN 3259 8/PG 3

WGK Germany 

3

RTECS 

RG8841500

F 

3-9-23

Autoignition Temperature

280 °C DIN 51794

HazardClass 

8

PackingGroup 

III

HS Code 

29212900

Toxicity

LD50 orally in Rabbit: 500 mg/kg

MSDS

• Language:English Provider:1,8-Diaminooctane
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
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1,8-Diaminooctane Usage And Synthesis

Chemical Properties

white to yellowish solidified crystalline mass

Uses

1,8-Diaminooctane is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

Definition

ChEBI: 1,8-diaminooctane is an alkane-alpha,omega-diamine in which the two amino groups are separated by eight methylene groups. It derives from a hydride of an octane.

Flammability and Explosibility

Non flammable

Safety Profile

Moderately toxic by ingestion. Asevere skin and eye irritant. When heated todecomposition it emits toxic vapors of NOx.

Synthesis

The general procedure for the synthesis of 1,8-octanediamine from 1,6-dicyanohexane was as follows: a 500 mL autoclave was assembled with a thermocouple thermometer, a stirrer (two-piece tilting paddle), a pressure gauge, and a hydrogen purge line. To the autoclave were added 175 g of 1,6-dicyanohexane, 86.0 g of methanol, 2.0 g of 28% sodium methacrylate-methanol solution (0.64% w/w), and 10.5 g of nickel catalyst (based on nickel monomers, which accounted for 6.0 w/w% of 1,6-dicyanohexane). The water content of the solution was 920 ppm at this point, as measured by a Karl Fischer hydrometer (manufactured by Hiranuma Sangyo Co., Ltd.) Upon completion of the dosing, hydrogen substitution was performed, and then the pressure was increased to 5 MPa. The temperature was raised to an internal temperature of 90 °C, and the ramping process lasted for approximately 1 hour. Hydrogen consumption was observed from about 70°C. The reaction was started at 90°C and hydrogen consumption essentially stopped after about 6 hours. After continuing the reaction for 2 hours, the reaction was cooled to room temperature, depressurized, and the reaction solution was filtered to remove the catalyst and the filtrate was washed with 100 g of methanol. The total weight of the 1,8-diaminooctane methanol reaction solution obtained was 377.4 g. The area of 1,8-diaminooctane was analyzed by GC to be 94.3% and the reaction yield was 96.7%.

Purification Methods

Distil the diamine under vacuum in an inert atmosphere (N2 or Ar), cool and store the distillate in an inert atmosphere in the dark. The dihydrochloride has m 273-274o. [Nae & Le Helv Chim Acta 15 55 1955, Beilstein 4 III 612.]

References

[1] Patent: JP2017/31143, 2017, A. Location in patent: Paragraph 0082; 0083; 0086; 0087
[2] Chemische Berichte, 1913, vol. 46, p. 230
[3] Patent: US6376714, 2002, B1
[4] Patent: US6376714, 2002, B1
[5] Patent: US2011/313186, 2011, A1. Location in patent: Page/Page column 11

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