Cyclohexylamine

Structural formula
General
Surname	Cyclohexylamine
other names	Aminocyclohexane; Hexahydroaniline; CHA;
Molecular formula	C 6 H 13 N
Brief description	colorless liquid with an amine-like odor
External identifiers / databases
EC number	203-629-0
ECHA InfoCard	100.003.300
PubChem	7965
Wikidata	Q1147539
properties
Molar mass	99.17 g mol −1
Physical state	liquid
density	0.86 g cm −3
Melting point	−18 ° C
boiling point	134 ° C
Vapor pressure	13 h Pa (20 ° C); 20 hPa (30 ° C); 60 hPa (50 ° C);
pK s value	10.64
solubility	soluble in water and trichloromethane; miscible with ethanol and diethyl ether;
Refractive index	1.4625 (15 ° C)
safety instructions
H and P phrases	H: 226-301-311-314-361f
	P: 210-280-302 + 352-305 + 351 + 338-308 + 313
MAK	DFG / Switzerland: 2 ml m −3 or 8.2 mg m −3
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Cyclohexylamine (also aminocyclohexane) is the name of a chemical compound , a primary amine derived from cyclohexane . It is a colorless to yellowish, fish-smelling, harmful liquid that is miscible with water. Cyclohexylamine is flammable and forms explosive mixtures with air. Even breathing in cyclohexylamine is dangerous. It is also quickly absorbed through the skin, damaging it in the process.

Presentation and extraction

Cyclohexylamine is the industrial scale by hydrogenation of aniline produced. It can also be prepared from cyclohexanol and ammonia or by simultaneous hydrogenation and amination of phenol with hydrogen and ammonia.

properties

Cyclohexylamine forms highly flammable vapor-air mixtures. The compound has a flash point of 27 ° C. The explosion range is between 1.14% by volume (47 g / m ³ ) as the lower explosion limit (LEL) and 9.4% by volume (387 g / m ³ as the upper explosion limit (UEL). It became a lower explosion point of 23 ° C. The ignition temperature is 275 ° C. The substance therefore falls into temperature class T3.

use

Cyclohexylamine is used as an intermediate in the synthesis of various herbicides , antioxidants , vulcanization accelerators, medicinal substances , corrosion protection agents and sweeteners ( cyclamate ).

Biological importance

Cyclohexylamine is a possible breakdown product of cyclohexylsulfamine, the sweetener cyclamate . In clinical studies, cyclamate consumed by around 5 percent of the people examined was partially broken down into cyclohexylamine, although the amount of cyclohexylamine produced was very different and also changed significantly during the study period.

Risk assessment

Cyclohexylamine was included in the EU's ongoing action plan ( CoRAP ) in 2014 in accordance with Regulation (EC) No. 1907/2006 (REACH) as part of substance evaluation . The effects of the substance on human health and the environment are re-evaluated and, if necessary, follow-up measures are initiated. The reasons for the uptake of cyclohexylamine were concerns about environmental exposure and high (aggregated) tonnage as well as the suspected dangers from reproductive properties. The re-evaluation took place from 2016 and was carried out by Belgium . A final report was then published.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o Entry on cyclohexylamine in the GESTIS substance database of the IFA , accessed on April 25, 2018(JavaScript required) .
↑ HK Hall Jr .: Correlation of the Base Strengths of Amines in J. Am. Chem. Soc. 79 (1957) 5441-5444, doi : 10.1021 / ja01577a030 .
↑ ^a ^b ^c ^d Entry on 1-hexane amine. In: Römpp Online . Georg Thieme Verlag, accessed on April 25, 2018.
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-128.
↑ Entry on Cyclohexylamine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 108-91-8 or cyclohexylamine ), accessed on November 2, 2015.
↑ US Patent 3196179
↑ US Patent 3346636
↑ US Patent 3551487
↑ US Patent 3364261
^ NE Buss et al .: The metabolism of cyclamate to cyclohexylamine and its cardiovascular consequences in human volunteers. Toxicol Appl Pharmacol . 115/2/ 1992 . Pp. 199-210. PMID 1379387
^ AG Renwick et al .: The metabolism of cyclamate to cyclohexylamine in humans during long-term administration. Toxicol Appl Pharmacol. 196/3/ 2004 . Pp. 367-80. PMID 15094307
↑ European Chemicals Agency (ECHA): Substance Evaluation Conclusion and Evaluation Report .
↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): Cyclohexylamine , accessed on March 26, 2019.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o Entry on cyclohexylamine in the GESTIS substance database of the IFA , accessed on April 25, 2018(JavaScript required) .

[2] HK Hall Jr .: Correlation of the Base Strengths of Amines in J. Am. Chem. Soc. 79 (1957) 5441-5444, doi : 10.1021 / ja01577a030 .

[Roempp-3] Entry on 1-hexane amine. In: Römpp Online . Georg Thieme Verlag, accessed on April 25, 2018.

[CRC90_3_128-4] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-128.

[CLP_100.003.300-5] Entry on Cyclohexylamine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[6] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 108-91-8 or cyclohexylamine ), accessed on November 2, 2015.

[7] US Patent 3196179

[8] US Patent 3346636

[9] US Patent 3551487

[10] US Patent 3364261

[11] NE Buss et al .: The metabolism of cyclamate to cyclohexylamine and its cardiovascular consequences in human volunteers. Toxicol Appl Pharmacol . 115/2/ 1992 . Pp. 199-210. PMID 1379387

[12] AG Renwick et al .: The metabolism of cyclamate to cyclohexylamine in humans during long-term administration. Toxicol Appl Pharmacol. 196/3/ 2004 . Pp. 367-80. PMID 15094307

[13] European Chemicals Agency (ECHA): Substance Evaluation Conclusion and Evaluation Report .

[14] Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): Cyclohexylamine , accessed on March 26, 2019.