1-butanol

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Structural formula
Structural formula of 1-butanol
General
Surname 1-butanol
other names
  • n -butanol
  • Butan-1-ol
  • Propyl carbinol
  • Propyl methanol
  • Butyl alcohol
  • Butyl hydroxide
  • N-BUTYL ALCOHOL ( INCI )
Molecular formula C 4 H 10 O
Brief description

colorless liquid with an ethanol-like odor

External identifiers / databases
CAS number 71-36-3
EC number 200-751-6
ECHA InfoCard 100,000,683
PubChem 263
DrugBank DB02145
Wikidata Q16391
properties
Molar mass 74.12 g · mol -1
Physical state

liquid

density

0.81 g cm −3 (20 ° C)

Melting point

−89 ° C

boiling point

118 ° C

Vapor pressure
  • 6.67 h Pa (20 ° C)
  • 13.3 hPa (30 ° C)
  • 25.1 hPa (40 ° C)
  • 45.4 hPa (50 ° C)
solubility

freely miscible with organic solvents, moderately soluble in water (77 g · l –1 at 20 ° C)

Refractive index

1.3988 (20 ° C)

safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
02 - Highly / extremely flammable 05 - Corrosive 07 - Warning

danger

H and P phrases H: 226-302-318-315-335-336
P: 210-280-302 + 352-304 + 340-305 + 351 + 338-313
MAK
  • DFG : 100 ml m −3 or 310 mg m −3
  • Switzerland: 50 ml m −3 or 150 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

1-Butanol (also n -butanol or butan-1-ol according to IUPAC ) is a chemical compound from the group of alkanols . The primary alcohol is derived from the aliphatic hydrocarbon n -butane .

Occurrence

1-Butanol occurs naturally in many foods and is produced during the microbiological breakdown of carbohydrates . It is also produced in the course of the breakdown of carbohydrates in the production of alcoholic beverages. This alcohol has also been found in fruits such as melons and apples as well as various foods such as cheese, heated milk and boiled rice, as well as in popcorn preparation , but also in breast milk. Older quantitative information from the 1960s on the maximum content of 1-butanol in food is 12 mg / l in beverages, 7 mg / kg in ice cream and 32 mg / kg in baked goods.

Extraction and presentation

1-Butanol can be produced in several ways. The hydroformylation of propene with subsequent hydrogenation of a resulting reaction product (butanal) is of industrial importance :

Butanol synthesis1

Propene reacts with carbon monoxide and hydrogen to form butanal and 2-methylpropanal .

Butanol synthesis2

The butanal produced reacts further with hydrogen to form 1-butanol.

Another production option based on renewable raw materials is the acetone-butanol-ethanol fermentation of sugar and starch with the help of Clostridium acetobutylicum . Such biologically produced 1-butanol is also known as biobutanol .

properties

Physical Properties

1-Butanol is a colorless liquid with a characteristic odor, which is described as "wine-like", but also as "bitter fusel-like with a banana aroma" and as "sweetish rancid". 1-Butanol can be mixed as desired with all common solvents such as ethers, glycol, alcohols, ketones and aldehydes. However, 1-butanol has only limited solubility in water. Water dissolves somewhat better in 1-butanol (approx. 20% by weight).

Chemical properties

Possible reactions of 1-butanol are esterification to an ester , dehydrogenation to an aldehyde or condensation to an ether :

Esterification to an ester:

Butanol reaction3

1-Butanol and propanoic acid react with acid catalysis ( e.g. with sulfuric acid ) to form n-butyl propionate and water .

Dehydration to an aldehyde:

Butanol reaction3

1-Butanol reacts to butanal with elimination of hydrogen.

Condensation to an ether:

Butanol reaction3

1-Butanol reacts with acid catalysis ( e.g. with hydrochloric acid ) to form di- n- butyl ether and water.

Safety-related parameters

1-Butanol is considered a flammable liquid. Flammable vapor-air mixtures can form above the flash point . The compound has a flash point of 35 ° C. The explosion range is between 1.4% by volume (43 g / m 3 ) as the lower explosion limit (LEL) and 11.3% by volume (350 g / m 3 ) as the upper explosion limit (UEL). The lower explosion point is 34 ° C. The maximum explosion pressure is 8.4 bar. The limit gap width was determined to be 0.91 mm. This results in an assignment to explosion group IIB. The ignition temperature is 325 ° C. The substance therefore falls into temperature class T2.

use

1-Butanol is used as a solvent in the manufacture of paints . It prevents whitening when the paint dries in a damp environment. 1-Butanol is also used as a starting material in the production of ethers and esters (such as butyl acetate and glycol butyl ethers and esters as well as phthalates and acrylates), which in turn serve as solvents or plasticizers . 1-Butanol can also be used as a solvent for dyes, as an additive in polishes and cleaning agents , as a component in fuels , as a solvent for thin-layer and paper chromatography , as an extraction agent in the production of pharmaceuticals or as a starting material for the production of flotation chemicals . In addition, 1-butanol, along with the other butanols, is considered a third-generation biofuel . 1-Butanol is also used as a reference material in olfactometry : 123 µg 1-butanol, if this is evaporated in 1 m 3 of neutral air under normal conditions, corresponds to a European odor unit . In addition, 1-butanol itself is used as a solvent, especially in paints, varnishes, resins and paint removers as well as some cosmetics and is used in the surface finishing of clothing.

Medical use

In the 1960s, 1-butanol was used as the main component of the drug, which became known under the trade name “Haemostypiticum Revici”, in particular in dentistry , to shorten bleeding times , for example in the case of secondary bleeding after tooth removal . Other additives were citric acid and disaccharides . According to Kuschinsky, the preparation sometimes contained trillium , a chemically undefined substance (trillium is a genus of lily plants) that is also said to have hemostatic activity. Emanuel Revici (1896–1997) was best known for his ineffective chemotherapy for cancer . In the absence of scientific evidence and the risk that further and useful measures would be neglected in reliance on the stated effectiveness of the “Haemostypiticums Revici”, the agent disappeared from the range of therapies in Europe in the 1980s after it had been used for years. In the USA it is still available as Revici Injection and Revici-e .

safety instructions

1-Butanol can be harmful if inhaled and swallowed: kidney and liver damage, dizziness, headaches, drowsiness up to unconsciousness and brain dysfunction can occur. It can also irritate the respiratory tract, digestive tract, eyes and skin. 1-Butanol should therefore not get into the hands of children.

According to animal experiments and in vitro data, 1-butanol is metabolized primarily by oxidation by means of alcohol dehydrogenase (ADH) via butanal and butanoic acid in the liver, and to a lesser extent by hepatic cytochrome P450 monoxygenases, the activity of which can be induced by ethanol is. Glucuronidation or sulfation of 1-butanol only takes place to a minor extent.

1-Butanol was included by the EU in 2017 in accordance with Regulation (EC) No. 1907/2006 (REACH) as part of substance evaluation in the Community's ongoing action plan ( CoRAP ). 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 1-butanol were concerns about consumer use , exposure of workers , high (aggregated) tonnage and widespread use, as well as the possible risk of reproductive toxicity . The re-evaluation took place from 2017 and was carried out by Hungary . A final report was then published.

Web links

Commons : 1-Butanol  - Collection of pictures, videos, and audio files
Wiktionary: 1-butanol  - explanations of meanings, word origins, synonyms, translations

Individual evidence

  1. Entry on N-BUTYL ALCOHOL in the CosIng database of the EU Commission, accessed on December 28, 2019.
  2. a b c d e f g h i j k l m n o p q r s t u Entry on 1-butanol in the GESTIS substance database of the IFA , accessed on December 19, 2019(JavaScript required) .
  3. 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. 3-74.
  4. Entry on butan-1-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 , accessed on August 28, 2019.
  6. a b c d e f Umweltbundesamt: Guide values ​​for 1-butanol in indoor air. In: Federal Health Gazette - Health Research - Health Protection. 57, 2014, p. 733, doi: 10.1007 / s00103-014-1972-x .
  7. BASF data sheet
  8. ^ William Andrew: OSHA regulated hazardous substances: health, toxicity, economic, and technological data. P. 273 ( limited preview in Google Book search).
  9. 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.
  10. ^ E. Brandes, M. Mitu, D. Pawel: The lower explosion point - A good measure for explosion prevention: Experiment and calculation for pure compounds and some mixtures. In: J. Loss Prev. Proc. Ind. 20, 2007, pp. 536-540, doi: 10.1016 / j.jlp.2007.04.028 .
  11. Entry on butanols. In: Römpp Online . Georg Thieme Verlag, accessed on November 12, 2014.
  12. Jens Lubbadeh: Fuel made from straw: Brewing fuel with super yeast. In: Spiegel Online. August 18, 2008.
  13. A. Ph. Van Harreveld, Paul Heeres: Quality control and optimization of dynamic olfactometry using n-butanol as a standard reference odorant. Dust - clean air , Volume 55, 2, 1995, pp. 45-50.
  14. DIN EN 13725: 2003-07 air quality; Determination of the odor concentration with dynamic olfactometry; German version EN 13725: 2003. Beuth Verlag, Berlin, p. 7.
  15. G. Kuschinsky, M. Lang, U. Wollert: Studies on the effect of butanol as a hemostyptic. In: DMW - German Medical Weekly. 93, 1968, p. 1443, doi: 10.1055 / s-0028-1110762 .
  16. Verstraete M. Report on a preparation of butyl alcohol: Haemostypticum Revici® . In: Haemostatic Drugs. Springer, Dordrecht, 1977, Retrieved August 27, 2019.
  17. European Chemicals Agency (ECHA): Substance Evaluation Conclusion and Evaluation Report
  18. Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): Butan-1-ol , accessed on March 26, 2019.