Propyleneimine

Propyleneimine
Names
	IUPAC name 2-Methylaziridine
	Other names 1,2-Propylenimine
Identifiers
CAS Number	75-55-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	6137;
ECHA InfoCard	100.000.799
EC Number	613-033-00-6;
KEGG	C19496;
PubChem CID	6377;
RTECS number	CM8050000;
UNII	ULC972Q7TZ ;
UN number	1921 (inhibited)
CompTox Dashboard (EPA)	DTXSID8024286 ;
	InChI InChI=1S/C3H7N/c1-3-2-4-3/h3-4H,2H2,1H3 Key: OZDGMOYKSFPLSE-UHFFFAOYSA-N; InChI=1/C3H7N/c1-3-2-4-3/h3-4H,2H2,1H3 Key: OZDGMOYKSFPLSE-UHFFFAOYAW;
	SMILES N1C(C)C1;
Properties
Chemical formula	C3H7N
Molar mass	57.096 g·mol−1
Appearance	Colorless, oily liquid
Odor	ammonia-like
Density	0.9 g/mL
Melting point	−63 °C (−81 °F; 210 K)
Boiling point	67 °C (153 °F; 340 K)
Solubility in water	Miscible
Vapor pressure	112 mmHg (20°C)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H300, H310, H318, H330, H350, H411
Precautionary statements	P201, P202, P210, P233, P240, P241, P242, P243, P260, P262, P264, P270, P271, P273, P280, P281, P284, P301+P310, P302+P350, P303+P361+P353, P304+P340, P305+P351+P338, P308+P313, P310, P320, P321, P322, P330, P361, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
Flash point	−4 °C (25 °F; 269 K)
	Lethal dose or concentration (LD, LC):
LCLo (lowest published)	500 ppm (rat, 4 hr)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 2 ppm (5 mg/m3) [skin]
REL (Recommended)	Ca TWA 2 ppm (5 mg/m3) [skin]
IDLH (Immediate danger)	Ca [100 ppm]
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Propyleneimine (or propylene imine) is the organic compound with the formula CH₃CH(NH)CH₂. It is a secondary amine and the smallest chiral aziridine (ring containing C₂N). It is a flammable colorless liquid. Its derivatives, copolymers and oligomers, are of commercial interest.^[4]

Uses

This chemical is used in the paper, textile, rubber and pharmaceutical industries. Propyleneimine is also used in making paint.

The top global producers of this specialty chemical include DuPont, Mitsubishi Chemical Holdings Corporation, Sigma-Aldrich, Dixie Chemical Company, J and K Scientific, Apollo Scientific, Mitsui Chemicals.^[5]

The compound is also of interest for the synthesis of dendrimers, a process that exploits the tendency of aziridines to undergo ring-opening reactions.^[6] ^[2]

Health Effects

NIOSH considers propyleneimine a potential occupational carcinogen.

According to a report prepared for the United Church of Christ, propyleneimine emissions from the Dixie Chemical Company facility in Bayport, Pasadena, Texas, are one of the top ten toxicity-weighted air pollutions in the United States.^[7]

References

^ ^a ^b ^c ^d ^e ^f NIOSH Pocket Guide to Chemical Hazards. "#0537". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b ^c ^d ^e ^f Propyleneimine International Chemical Safety Card at actrav.itcilo.org
^ "Propylene imine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ Steuerle, Ulrich; Feuerhake, Robert (2006). "Aziridines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_239.pub2. ISBN 3527306730.
^ Global QYResearch. "Propyleneimine Market Analysis, Size, Share, Trends, Growth and Forecasts Report 2019-2026". MarketWatch, Inc. Retrieved 14 March 2020.
^ Malik, N.; Wiwattanapatapee, R.; Klopsch, R.; Lorenz, K.; Frey, H.; Weener, J. W.; Meijer, E. W.; Paulus, W.; Duncan, R. (2000). "Dendrimers: Relationship between structure and biocompatibility in vitro, and preliminary studies on the biodistribution of 125I-labeled polyamidoamine dendrimers in vivo". Journal of Controlled Release. 65 (1–2): 133–148. doi:10.1016/S0168-3659(99)00246-1. PMID 10699277.
^ "Breath to the People: Sacred Air and Toxic Pollution" (PDF). United Church of Christ. pp. 12, 21. Retrieved 14 March 2020.

[PGCH-1] ^ ^a ^b ^c ^d ^e ^f NIOSH Pocket Guide to Chemical Hazards. "#0537". National Institute for Occupational Safety and Health (NIOSH).

[ICSC-2] ^ ^a ^b ^c ^d ^e ^f Propyleneimine International Chemical Safety Card at actrav.itcilo.org

[3] "Propylene imine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[Ullmann-4] Steuerle, Ulrich; Feuerhake, Robert (2006). "Aziridines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_239.pub2. ISBN 3527306730.

[5] Global QYResearch. "Propyleneimine Market Analysis, Size, Share, Trends, Growth and Forecasts Report 2019-2026". MarketWatch, Inc. Retrieved 14 March 2020.

[6] Malik, N.; Wiwattanapatapee, R.; Klopsch, R.; Lorenz, K.; Frey, H.; Weener, J. W.; Meijer, E. W.; Paulus, W.; Duncan, R. (2000). "Dendrimers: Relationship between structure and biocompatibility in vitro, and preliminary studies on the biodistribution of 125I-labeled polyamidoamine dendrimers in vivo". Journal of Controlled Release. 65 (1–2): 133–148. doi:10.1016/S0168-3659(99)00246-1. PMID 10699277.

[7] "Breath to the People: Sacred Air and Toxic Pollution" (PDF). United Church of Christ. pp. 12, 21. Retrieved 14 March 2020.

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