2-propanol

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Structural formula
Structure of 2-propanol
General
Surname 2-propanol
other names
  • Propan-2-ol ( IUPAC )
  • Propanol-2
  • Isopropanol
  • i-PrOH
  • i- propanol
  • iso- propanol
  • Isopropyl alcohol (IPA)
  • secondary propyl alcohol
  • sec -propanol
  • Persprit
  • Petrohol
  • Petrosol
  • Dimethyl carbinol
  • β-hydroxypropane
  • Propol
  • Alcohol isopropylicus
  • ISOPROPYL ALCOHOL ( INCI )
Molecular formula C 3 H 8 O
Brief description

colorless liquid with a characteristic, alcohol-like odor

External identifiers / databases
CAS number 67-63-0
EC number 200-661-7
ECHA InfoCard 100,000,601
PubChem 3776
ChemSpider 3644
DrugBank DB02325
Wikidata Q16392
properties
Molar mass 60.10 g mol −1
Physical state

liquid

density

0.78 g cm −3

Melting point

−88 ° C

boiling point

82 ° C

Vapor pressure

42.6 h Pa (20 ° C)

solubility

completely miscible with water, ethanol, acetone, chloroform, benzene

Refractive index

1.37927 (20 ° C)

safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
02 - Highly / extremely flammable 07 - Warning

danger

H and P phrases H: 225-319-336
P: 210-233-240-305 + 351 + 338-403 + 235
MAK
  • DFG : 200 ml m −3 or 500 mg m −3
  • Switzerland: 200 ml m −3 or 500 mg m −3
Toxicological data
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-propanol ( IUPAC -name propan-2-ol ), also known as isopropyl alcohol or isopropanol (abbreviated to IPA ), is the simplest non-cyclic, secondary alcohol and a monohydric alcohol.

Presentation and extraction

2-propanol is commercially produced by hydration of propene to acidic ion exchange resins as catalyst :

Synthesis of isopropanol by acid-catalyzed hydration of propene

Alternatively, 2-propanol can be obtained by catalytic hydrogenation of acetone :

2-propanol synthesis

By reversing the second reaction, acetone is produced on an industrial scale from isopropanol by oxydehydrogenation; H. Dehydrogenation with simultaneous oxidation of the resulting hydrogen with oxygen to form water.

properties

Physical Properties

Isopropanol is a colorless, volatile and flammable liquid that has a slightly sweet, pungent odor - this is characteristic and is reminiscent of hospitals and medical practices, as isopropanol is a component of many disinfectants. At −88 ° C the liquid solidifies to a colorless solid. The boiling point under normal pressure is 82 ° C. Isopropanol can be mixed homogeneously with water in any proportion and forms a constant boiling ( azeotropic ) mixture at 80.4 ° C and a water content of 12.1%. The compound forms azeotropically boiling mixtures with a number of other solvents. The azeotropic compositions and boiling points can be found in the following table. With methanol , ethanol , 1-propanol , n -butanol , iso -butanol , sec -butanol , cyclohexanol , ethanediol , ethylbenzene , acetone , diethyl ether , 1,4-dioxane , methyl acetate and dimethyl formamide not be azeotropes formed.

Azeotropes with various solvents
solvent n -pentane n -hexane n -heptane n- octane Cyclohexane benzene toluene
Isopropanol content in mass% 6th 23 51 84 32 33 69
boiling point in ° C 35 63 76 82 69 72 81
solvent Methyl ethyl ketone Diisopropyl ether Ethyl acetate Isopropyl acetate Acetonitrile chloroform Carbon tetrachloride
Isopropanol content in mass% 32 15th 25th 52 48 4th 18th
boiling point in ° C 78 66 75 80 75 61 69

Thermodynamic properties

According to Antoine, the vapor pressure curve is obtained according to log 10 (P) = A− (B / (T + C)) (P in bar, T in K) with A = 4.57795, B = 1221.423 and C = −87.474 in the temperature range from 359.0 to 508.24 K.

Compilation of the most important thermodynamic properties
property Type Value [unit] Remarks
Standard enthalpy of formation Δ f H 0 liquid
Δ f H 0 gas 		−318.2 kJ mol −1
−272.3 kJ mol −1
Standard entropy S 0 liquid 180.58 J mol −1 K −1 as a liquid
Enthalpy of combustion Δ c H 0 liquid −2005.8 kJ mol −1
Heat capacity c p 161.2 J mol −1 K −1 (25 ° C)
2.68 J g −1 K −1 (25 ° C)
89.32 J mol −1 K −1 (25 ° C )
1.49 J g −1 K −1 (25 ° C) 		as a liquid

as a gas
Critical temperature T c 508.3 K
Critical pressure p c 47.6 bar
Acentric factor ω c 0.66687
Enthalpy of fusion Δ f H 0 5.41 kJ mol −1 at the melting point
Enthalpy of evaporation Δ V H 0 39.85 kJ mol −1 at normal pressure boiling point

The temperature dependence of the enthalpy of vaporization can be calculated according to the equation Δ V H 0 = A e (−αT r ) (1 − T r ) β (Δ V H 0 in kJ / mol, T r = (T / T c ) reduced temperature ) with A = 53.38 kJ / mol, α = −0.708, β = 0.6538 and T c = 508.3 K in the temperature range between 298 K and 380 K.

Safety-related parameters

2-Propanol forms highly flammable vapor-air mixtures. The compound has a flash point of 12 ° C. The explosion range is between 2% by volume (50 g / m 3 ) as the lower explosion limit (LEL) and 13.4% by volume (335 g / m 3 ) as the upper explosion limit (UEL). A correlation of the explosion limits with the vapor pressure function results in a lower explosion point of 10 ° C and an upper explosion point of 39 ° C. The explosion limits are temperature and pressure dependent. Increased temperatures lead to an expansion of the explosion range. A reduction in pressure leads to a reduction in the explosion area. The lower explosion limit changes only slightly up to a pressure of 100 mbar and only increases at pressures below 100 mbar. The upper explosion limit decreases analogously with falling pressure. The maximum explosion pressure at 50 ° C is 8.6 bar. The maximum explosion pressure decreases with increasing temperature and decreasing outlet pressure.

Explosion limits at elevated temperature (measured at 1013 mbar)
temperature in ° C 20th 100 150
Lower explosion limit (LEL) in% by volume 2.2 1.9 1.6
in g m −3 54 47 39
Upper explosion limit (UEL) in% by volume 12.8 13.4
in g m −3 320 335
Explosion limits under reduced pressure (measured at 100 ° C)
pressure in mbar 1013 800 600 400 300 250 200 150 100 50 25th
Lower explosion limit (LEL) in% by volume 1.9 1.9 2.0 2.0 2.1 2.1 2.2 2.3 2.4 3.1 3.8
in g m −3 47 47 49 50 51 52 54 56 59 76 92
Upper explosion limit (UEL) in% by volume 13.4 12.8 12.3 11.8 11.6 11.6 11.7 11.7 11.3 9.5 6.0
in g m −3 335 320 397 295 287 290 292 292 282 237 150
Maximum explosion pressure and limit oxygen concentration under reduced pressure
pressure in mbar 1013 800 600 400 200 100
Maximum explosion pressure in cash at 50 ° C 8.6 6.8 5.1 3.4 1.7 0.8
at 100 ° C 7.5 6.0 4.5 3.0 1.5 0.8
Limit oxygen concentration in% by volume at 20 ° C 8.7 9.0
at 100 ° C 8.1 8.1 8.3 8.4

The limit oxygen concentration at 20 ° C is 8.7% by volume, at 100 ° C it is 8.1% by volume. It changes little under reduced pressure. The limit gap width was determined to be 0.99 mm. This results in an assignment to explosion group IIA. The ignition temperature is 425 ° C. The substance therefore falls into temperature class T2. The electrical conductivity is rather low at 5.8 · 10 −6  S · m −1 . In aqueous solutions, the flash point changes only slightly from <20 ° C up to a water content of 80 mol%.

Chemical properties (safety)

Like other secondary alcohols, 2-propanol can form explosive peroxides with atmospheric oxygen . For example, a peroxide content of 1% was found in containers in which isopropanol had been stored for ten years; Peroxide concentrations up to 4.2% have been reported. When 2-propanol was distilled off to dryness, accidents were sometimes serious. It is therefore advisable to check isopropanol for peroxides before distilling off.

toxicology

The fumes are numbing. Contact causes irritation to the eyes and mucous membranes. Adequate ventilation should be provided when handling. No evidence of sensitizing or mutagenic properties was found in animal experiments .

The lethal dose is 5,050 mg kg −1 in the rat ( LD 50 oral) and 12,800 mg kg −1 in the rabbit (LD 50 dermal).

use

2-propanol: colorless liquid

Regulations and approvals

According to EU Directive 98/8 / EC of February 16, 1998, biocidal products should only be permitted whose active substances have been included in the appendix (Appendix I, IA and IB) of the aforementioned directive (for the defined product type). According to the transitional regulation (Art. 16 (1) of Directive 98/8 / EC), the placing on the market of biocidal products that do not contain the active substances listed in the annex to Directive 98/8 / EC, provided that these active substances with the reference date May 14th 2000 were already on the market (also called "old active ingredients").

According to EU regulation 1896/2000 of September 7, 2000, manufacturers who wanted to apply for the inclusion of an "old active substance" in Annexes I, IA and IB had to report the relevant active substance for notification for the corresponding product type by March 28, 2002 to have. This period was extended by EU regulation 1687/2000 from September 25, 2002 to January 31, 2003. The “notified active substances” were allowed to remain on the market until the final decision on inclusion or non-inclusion in Annex I, IA and IB of EU Directive 98/8 / EC.

The active ingredient propan-2-ol was added to the list of notified active ingredients for product types 1 to 6, 9 to 12 and 18.

With resolution of August 14, 2007 for product type 18 (insecticides), with resolution of October 14, 2008 for product types 3 (hygiene in the veterinary sector), 5 (drinking water disinfectants) and 6 (pot preservatives) as well as with resolution of February 8 In 2010, decisions were made for product groups 9 to 12 (various protective agents) not to include the active ingredient propan-2-ol in the corresponding list (Annex I / IA of Directive 98/8 / EC) for the product types mentioned. The sale of biocidal products that contain the active ingredient propan-2-ol is therefore no longer permitted in the EU (Switzerland has adopted this provision) for the corresponding product types. The decision is still pending for product groups 1 (human hygiene), 2 (disinfectants for the private sector) and 4 (disinfectants for the food and feed sector).

As the spread of the SARS-CoV-2 coronavirus in Germany has increased the demand for disinfectants for hand disinfection, and the corresponding preparations are currently no longer available in pharmacies and drugstores (as of March 2020), the Federal Office for Chemicals, as the competent authority, has announced the general decree on the approval of 2-propanol-containing biocidal products for hygienic hand disinfection in accordance with Article 55 (1) of Regulation (EU) No. 528/2012 after consultation with the Federal Ministry for the Environment, Nature Conservation and Nuclear Safety . This general decree expires on August 31, 2020.

Web links

Commons : 2-Propanol  - Collection of pictures, videos, and audio files
Wiktionary: 2-Propanol  - explanations of meanings, word origins, synonyms, translations

Individual evidence

  1. ↑ Entry on ISOPROPYL ALCOHOL in the CosIng database of the EU Commission, accessed on February 16, 2020.
  2. ↑ a b c d e f g h i j k l m Entry on 2-propanol in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
  3. ↑ CRC Handbook of Tables for Organic Compound Identification , Third Edition, 1984, ISBN 0-8493-0303-6 .
  4. ↑ Entry on propan-2-ol 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 .
  5. ↑ Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values (search for 67-63-0 or 2-propanol ), accessed on September 14, 2019.
  6. ↑ a b Gigiena i Sanitariya. (HYSAAV) . Vol. 43 (1), p. 8, 1978.
  7. ↑ a b Raw Material Data Handbook. Vol. 1: Organic Solvents. Vol. 1, 1974, p. 100.
  8. ↑ a b I. M. Smallwood: Handbook of organic solvent properties. Arnold, London 1996, ISBN 0-340-64578-4 , pp. 73-75.
  9. ↑ D. Ambrose, R. Townsend: Thermodynamic Properties of Organic Oxygen Compounds. Part 9: The Critical Properties and Vapor Pressures, above Five Atmospheres, of Six Aliphatic Alcohols. In: J. Chem. Soc. 1963, pp. 3614-3625.
  10. ↑ a b c A. Snelson, HA Skinner: Heats of combustion: sec-propanol, 1,4-dioxane, 1,3-dioxane and tetrahydropyran. In: Trans. Faraday Soc. 57, 1961, pp. 2125-2131.
  11. ^ A b R. JL Andon, JF Counsel, JF Martin: Thermodynamic properties of organic oxygen compounds. Part II: The thermodynamic properties from 10 to 330 K of isopropyl alcohol. In: Trans. Faraday Soc. 59, 1963, pp. 1555-1558.
  12. ^ A b G. Roux, D. Roberts, G. Perron, JE Desnoyers: Microheterogeneity in aqueous-organic solutions: heat capacities, volumes and expansibilities of some alcohols, aminoalcohol and tertiary amines in water. In: J. Solution Chem. 9, 1980, pp. 629-647, doi: 10.1007 / BF00645894 .
  13. ^ A b Thermodynamics Research Center: Selected Values ​​of Properties of Chemical Compounds. Thermodynamics Research Center, Texas A&M University, College Station, Texas 1997.
  14. ^ A b M. Gude, AS Teja: Vapor-Liquid Critical Properties of Elements and Compounds. 4. Aliphatic Alkanols. In: J. Chem. Eng. Data . 40, 1995, pp. 1025-1036; doi: 10.1021 / je00021a001 .
  15. ↑ J. Schmidt: Design of safety valves for multi-purpose systems according to ISO 4126-10. In: Chem. Ing. Techn. 83, 2011, pp. 796-812, doi: 10.1002 / cite.201000202 .
  16. ^ A b V. Majer, V. Svoboda: Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation. Blackwell Scientific Publications, Oxford 1985, p. 300.
  17. ↑ 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.
  18. ↑ a b c d e f g D. Pawel, E. Brandes: Final report on the research project, the dependence of safety parameters on the pressure below atmospheric pressure. ( Memento of December 2, 2013 in the Internet Archive ) (PDF; 591 kB), Physikalisch-Technische Bundesanstalt (PTB), Braunschweig 1998.
  19. ↑ Technical rule for hazardous substances TRGS 727, BG RCI leaflet T033 Avoidance of ignition hazards due to electrostatic charges , status August 2016, Jedermann-Verlag Heidelberg, ISBN 978-3-86825-103-6 .
  20. ↑ H.-J. Liaw, YY Chiu: The prediction of the flash point for binary aqueous-organic solutions. In: J. Hazard. Mat. 101, 2003, pp. 83-106. doi: 10.1016 / S0304-3894 (03) 00168-7 .
  21. ↑ a b Accidents caused by peroxide-forming substances ( Memento of March 4, 2016 in the Internet Archive ). BG RCI (PDF; 88 kB).
  22. ↑ G. A. Mirafzal, HE Baumgarten: Control of peroxidizable compounds: An addendum (SAFETY). In: J. Chem. Ed. 65, 1988, p. A226, doi: 10.1021 / ed065pA226 .
  23. ↑ TW Sharples: Butanol safety hazard (LTE). In: J. Chem. Ed. 61, 1984, p. 476, doi: 10.1021 / ed061p476.1 .
  24. ↑ In Bathe: Chem Ber. 10/1974, p. 143.
  25. ↑ Michael Zölffel: The clean microscope. (PDF; 3.5 MB) Carl Zeiss .
  26. ↑ TU Munich : Brief description: Continuous cloud chamber. .
  27. ↑ Directive 98/8 / EC of February 16, 1998 on the placing of biocidal products on the market . In: Official Journal of the European Communities . L 123, April 24, 1998, pp. 1-63.
  28. ↑ Regulation (EC) No. 1896/2000 on the first phase of the program according to Article 16 paragraph 2 of Directive 98/8 / EC on biocidal products . In: Official Journal of the European Communities . L 228, September 8, 2000, p. 6.
  29. ↑ Regulation (EC) No. 1687/2000 on an additional period for the notification of certain active substances . In: Official Journal of the European Communities . L 258, September 26, 2000, pp. 15-16.
  30. ↑ Regulation (EC) No. 2032/2003 on the second phase of the ten-year work program on placing biocidal products on the market . In: Official Journal of the European Communities . L 307, November 24, 2003, p. 1.
  31. ↑ Decision on the non-inclusion of certain active substances in Annex I of Directive 98/8 / EC . In: Official Journal of the European Communities. L 216, August 21, 2007, pp. 17-21.
  32. ↑ Decision on the non-inclusion of certain active substances in Appendix I, IA or IB of Directive 98/8 / EC . In: Official Journal of the European Communities. L 251, October 24, 2008, pp. 16-29.
  33. ↑ Decision on the non-inclusion of certain active substances in Annex I of Directive 98/8 / EC . In: Official Journal of the European Communities. L 36, February 9, 2010, pp. 36-50.
  34. ↑ Federal Institute for Occupational Safety and Health : General decree on the approval of 2-propanol-containing biocidal products for hygienic hand disinfection due to a risk to public health (PDF; 874 kB)