2-chloropropane

Structural formula
General
Surname	2-chloropropane
other names	2-propyl chloride Isopropyl chloride
Molecular formula	C 3 H 7 Cl
Brief description	colorless liquid with a chloroform-like odor
External identifiers / databases
CAS number 75-29-6 26446-76-4 (mixture with 1-chloropropane) EC number 200-858-8 ECHA InfoCard 100,000,781 PubChem 6361 Wikidata Q209360
properties
Molar mass	78.54 g mol −1
Physical state	liquid
density	0.86 g cm −3
Melting point	−117 ° C
boiling point	35 ° C
Vapor pressure	567 h Pa (20 ° C) 820 hPa (30 ° C)
solubility	heavy in water (3.1 g l −1 at 20 ° C)
Refractive index	1.378
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 225-332-312-302-290 P: 210-233-301 + 312-303 + 361 + 353-304 + 340-403 + 235
Thermodynamic properties
ΔH f 0	−172.3 kJ / mol
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

2-chloropropane is an organic-chemical compound from the group of chlorinated hydrocarbons (CHC).

Extraction and presentation

2-Chloropropane can be obtained by chlorination of propane , whereby 1-chloropropane is also formed to a large extent depending on the temperature (see also Markovnikov's rule ).

properties

2-chloropropane is a very volatile, colorless liquid with a chloroform-like odor. In contrast to many haloalkanes, it has a lower density than water.

Thermodynamic properties

According to Antoine, the vapor pressure function results from log ₁₀ (P) = A− (B / (T + C)) (P in bar, T in K) with A = 3.81944, B = 1022.222 and C = −41.619 in the temperature range from 194.3 to 309.7 K.

Compilation of the most important thermodynamic properties

property	Type	Value [unit]	Remarks
Enthalpy of combustion	Δ f H 0 liquid Δ f H 0 gas	−2028.4 kJ mol −1 −2059.6 kJ mol −1
Standard enthalpy of formation	Δ c H 0 liquid	−145.0 kJ mol −1
Critical temperature	T c	489 K
Critical pressure	p c	45.4 bar
Critical volume	V c	0.247 l mol −1
Critical density	ρ c	0.318 g ml −1
Acentric factor	ω c	0.199
Enthalpy of fusion	Δ fus H	7.39 J · mol -1 ·	at the melting point
Enthalpy of evaporation	Δ V H	27.2 kJ mol −1	at normal pressure boiling point

The temperature dependence of the enthalpy of vaporization can be calculated according to the simplified Watson equation Δ _V H = A · (1 − T _r ) ⁿ (Δ _V H in kJ / mol, T _r = (T / T _c ) reduced temperature) with A = 40.56 Describe kJ / mol, n = 0.419 and T _c = 489.0 K in the temperature range between 156 K and 489 K.

Safety-related parameters

2-chloropropane forms highly flammable vapor-air mixtures. The compound has a flash point below -36 ° C. The explosion range is between 2.8% by volume (90 g / m ³ ) as the lower explosion limit (LEL) and 10.7% by volume (350 g / m ³ ) as the upper explosion limit (UEL). The limit gap width was determined to be 1.32 mm (50 ° C). This results in an assignment to explosion group IIA. The ignition temperature is 590 ° C. The substance therefore falls into temperature class T1.

Individual evidence

1. ↑ ^{a b c d e f g h i j k l} Entry on 2-chloropropane in the GESTIS substance database of the IFA , accessed on February 19, 2018(JavaScript required) .
2. ↑ Data sheet 2-chloropropane from Sigma-Aldrich , accessed on April 2, 2010 ( PDF ).
3. ↑ Entry on 2-chloropropane 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 .
4. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Standard Thermodynamic Properties of Chemical Substances, pp. 5-24.
5. ↑ J. Clayden , N. Greeves , S. Warren , P. Wothers : Organic Chemistry. 1st edition. Oxford University Press, 2000, ISBN 0-19-850346-6 , p. 1036.
6. ↑ Chemgapedia: Chlorination of higher alkanes
7. ^ DR Stull: Vapor Pressure of Pure Substances Organic Compounds. In: Ind. Eng. Chem. 39, 1947, pp. 517-540, doi: 10.1021 / ie50448a022 .
8. ↑ L. Smith, L. Bjellerup, S. Krook, H. Westermark: Heats of combustion of organic chloro compounds determined by the "quartz wool" method. In: Acta Chem. Scand. 7, 1953, pp. 65–86, doi: 10.3891 / acta.chem.scand.07-0065 , (pdf)
9. ↑ ^{a b} R. A. Fletcher, G. Pilcher: Measurements of heats of combustion by flame calorimetry. Part 7.-Chloromethane, chloroethane, 1-chloropropane, 2-chloropropane. In: Trans. Faraday Soc. 67, 1971, pp. 3191-3201, doi: 10.1039 / TF9716703191 .
10. ^ ^{A b c d e} Carl L. Yaws, Prasad K. Narasimhan: Thermophysical Properties of Chemicals and Hydrocarbons - Chapter 1: Critical Properties and Acentric Factor, Organic Compounds. 1st edition. Elsevier 2008, ISBN 978-0-8155-1596-8 , p. 8, doi: 10.1016 / B978-081551596-8.50006-7 .
11. ↑ WE Acree: Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation. In: Thermochim. Acta . 189, 1991, pp. 37-56, doi: 10.1016 / 0040-6031 (91) 87098-H .
12. ↑ JH Mathews, PR Fehlandt: The heats of vaporization of some organic compounds. In: J. Am. Chem. Soc. 53, 1931, pp. 3212-3217, doi: 10.1021 / ja01360a002 .
13. ↑ JB Pedley, RD Naylor, SP Kirby: Thermochemical Data of Organic Compounds. Chapman and Hall, New York 1986.
14. ^ Carl L. Yaws, Marco A. Satyro: Thermophysical Properties of Chemicals and Hydrocarbons - Chapter 7: Enthalpy of Vaporation, Organic Compounds. 1st edition. Elsevier 2008, ISBN 978-0-8155-1596-8 , p. 315, doi: 10.1016 / B978-081551596-8.50012-2 .
15. ↑ ^{a b c d} E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.