Allyl alcohol

Structural formula
General
Surname	Allyl alcohol
other names	Prop-2-en-1-ol ( IUPAC ); Acrylic alcohol; Acryloxide hydrate; 2-propen-1-ol; Vinyl carbinol;
Molecular formula	C 3 H 6 O
Brief description	colorless liquid with an irritating smell of mustard oil
External identifiers / databases
EC number	203-470-7
ECHA InfoCard	100.003.156
PubChem	7858
Wikidata	Q414553
properties
Molar mass	58.08 g mol −1
Physical state	liquid
density	0.85 g cm −3
Melting point	−129 ° C
boiling point	97 ° C
Vapor pressure	23.9 h Pa (20 ° C)
pK s value	15.5 (25 ° C)
solubility	miscible with water
Refractive index	1.4135 (20 ° C)
safety instructions
H and P phrases	H: 225-301-310-330-319-335-315-410
	P: 210-280-303 + 361 + 353-305 + 351 + 338-501
MAK	not specified because it is carcinogenic; Switzerland: 2 ml m −3 or 5 mg m −3 ;
Thermodynamic properties
ΔH f 0	−171.8 kJ mol −1
	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

Allyl alcohol , also known as 2-propen-1-ol , is a colorless, clear chemical compound that is liquid at room temperature . It forms violently irritating vapors with a dull, pungent odor. It consists of a chain of three carbon atoms with a double bond , as well as hydrogen atoms and a hydroxyl group (OH group). Allyl alcohol is therefore an unsaturated alcohol and one of the alkenols .

Extraction and presentation

The first preparation of allyl alcohol was in 1856 by Cahours and Hofmann starting from allyl iodide .

Industrial syntheses

The industrial production of allyl alcohol can be prepared by isomerization of propylene oxide at temperatures of 270-320 ° C and low pressures of 1-2 bar over supported lithium phosphate - catalysts take place.

A gas mixture of propylene oxide and an inert gas or pure propylene oxide is passed into a fixed bed reactor . The propylene oxide conversion is preferably adjusted to about 70-75%. The selectivity for allyl alcohol is then 95-97%. Small amounts of acetone and propionaldehyde are formed as essential by-products .

In addition, allyl alcohol can also be effected by alkaline hydrolysis of allyl chloride , by hydrolysis / methanolysis of allyl acetate or by selective hydrogenation of acrolein (e.g. over silver catalysts).

Laboratory scale

In the laboratory, allyl alcohol can be produced by reacting glycerine with formic acid .

In addition, allyl alcohol is accessible by a Meerwein-Ponndorf-Verley reduction of acrolein or as a by-product of a Tishchenko reaction .

Use (selection)

Allyl alcohol is an important intermediate in numerous organic chemical syntheses. Acrolein is obtained through targeted oxidation , from which> 400,000 t / year of the amino acid DL - methionine are produced; Evonik Industries is the world market leader for this . The drug dimercaprol is made from allyl alcohol in two stages.

safety instructions

Allyl alcohol is flammable and toxic by inhalation, ingestion and on contact with skin. It should be stored at a maximum of 15 ° C and therefore in a refrigerator for chemicals.

literature

Entry on allyl alcohol. In: Römpp Online . Georg Thieme Verlag, accessed on November 11, 2014.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on allyl alcohol in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Dissociation Constants of Organic Acids and Bases, pp. 8-43.
↑ 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. 3-12.
↑ Entry on Allyl alcohol 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 107-18-6 or allyl alcohol ), accessed on November 2, 2015.
↑ 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.
↑ ^a ^b Ullmann's Encyclopedia of Industrial Chemistry , Wiley-VCH, 2000 doi : 10.1002 / 14356007.a01_425 .
^ Stefan Marz: Gas phase conversion of dimethyl maleate to tetrahydrofuran: process intensification and kinetics. In: KIT Scientific Publishing. Karlsruhe Institute of Technology, February 20, 2014, p. 20, doi : 10.5445 / KSP / 1000036268
↑ Hans-Jürgen Arpe: Industrial organic chemistry - important preliminary and intermediate products . 6th edition. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 2007, ISBN 978-3-527-31540-6 , pp. 330 .
↑ J. Hohmeyer: Characterization of silver catalysts for selective hydrogenation using DRIFT spectroscopy, adsorption calorimetry and TAP reactor . Dissertation, Fritz Haber Institute Berlin / Technical University Darmstadt, 2009.
^ O. Kamm, ER Taylor: Allyl alcohol In: Organic Syntheses . 1, 1921, p. 15, doi : 10.15227 / orgsyn.001.0015 ; Coll. Vol. 1, 1941, p. 42 ( PDF ).
↑ H. Beyer, W. Walter Textbook of Organic Chemistry , 23rd edition, Hirzel Verlag, Stuttgart, 1998.
^ Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dieter Reichert: Pharmaceutical Substances , 4th edition (2000), 2 volumes published by Thieme-Verlag Stuttgart, pp. 662-663, ISBN 978-1-58890-031-9 ; online since 2003 with biannual additions and updates.

Web links

Commons : Allyl Alcohol - Collection of pictures, videos and audio files

Wiktionary: Allyl alcohol - explanations of meanings, word origins, synonyms, translations

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ Entry on allyl alcohol in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .

[CRC90_8_43-2] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Dissociation Constants of Organic Acids and Bases, pp. 8-43.

[CRC90_3_12-3] 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. 3-12.

[CLP_100.003.156-4] Entry on Allyl alcohol 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 107-18-6 or allyl alcohol ), accessed on November 2, 2015.

[CRC90_5_24-6] 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.

[Ullmann2000-7] Ullmann's Encyclopedia of Industrial Chemistry , Wiley-VCH, 2000 doi : 10.1002 / 14356007.a01_425 .

[KIT-8] Stefan Marz: Gas phase conversion of dimethyl maleate to tetrahydrofuran: process intensification and kinetics. In: KIT Scientific Publishing. Karlsruhe Institute of Technology, February 20, 2014, p. 20, doi : 10.5445 / KSP / 1000036268

[ARPE-9] Hans-Jürgen Arpe: Industrial organic chemistry - important preliminary and intermediate products . 6th edition. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 2007, ISBN 978-3-527-31540-6 , pp. 330 .

[PhDHohmeyer-10] J. Hohmeyer: Characterization of silver catalysts for selective hydrogenation using DRIFT spectroscopy, adsorption calorimetry and TAP reactor . Dissertation, Fritz Haber Institute Berlin / Technical University Darmstadt, 2009.

[OrgSyn-11] O. Kamm, ER Taylor: Allyl alcohol In: Organic Syntheses . 1, 1921, p. 15, doi : 10.15227 / orgsyn.001.0015 ; Coll. Vol. 1, 1941, p. 42 ( PDF ).

[BeyerWalter-12] H. Beyer, W. Walter Textbook of Organic Chemistry , 23rd edition, Hirzel Verlag, Stuttgart, 1998.

[Kleemann-13] Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dieter Reichert: Pharmaceutical Substances , 4th edition (2000), 2 volumes published by Thieme-Verlag Stuttgart, pp. 662-663, ISBN 978-1-58890-031-9 ; online since 2003 with biannual additions and updates.