1,9-nonanediol

Structural formula
General
Surname	1,9-nonanediol
other names	Nonamethylene glycol
Molecular formula	C 9 H 20 O 2
Brief description	colorless solid
External identifiers / databases
EC number	223-517-5
ECHA InfoCard	100.021.380
PubChem	19835
Wikidata	Q20054536
properties
Molar mass	160.25 g mol −1
Physical state	firmly
density	0.950 g cm −3
Melting point	45-47 ° C
boiling point	288 ° C; 177 ° C (at 15 mmHg);
solubility	poorly soluble in water; easily soluble in ethanol;
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1,9-Nonanediol is a chemical compound from the group of alkanediols .

Extraction and presentation

1,9-nonanediol, by isomerization of allyl alcohol to aldehyde , hydroformylation are produced and reduction.

The compound can also be obtained by reacting oleic acid methyl ester with triethylsilyl hydrotrioxide and lithium aluminum hydride .

Also possible is the representation by hydrodimerization of 1,3-butadiene with water or from 7-octenal by hydroformylation to 1,9-Nonadial and desser hydrogenation to 1,9-nonanediol.

properties

1,9-Nonanediol is a colorless solid that dissolves little in water but dissolves well in ethanol .

use

1,9-Nonanediol is used in the manufacture of polymers. It is also used as an intermediate in the manufacture of aroma chemicals and in the pharmaceutical industry. It is also suitable as a starting material for the production of azelaic acid . By reacting 1,9-nonanediol with thionyl chloride can 1,9-dichlorononane be won. 1,9-Dibromononane can be obtained by bromination .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g data sheet 1,9-Nonanediol, 98% from Sigma-Aldrich , accessed on April 30, 2015 ( PDF ).
↑ ^a ^b Data sheet 1,9-Nonanediol, 97% from AlfaAesar, accessed on April 30, 2015 ( PDF )(JavaScript required) .
↑ ^a ^b ^c William M. Haynes: CRC Handbook of Chemistry and Physics, 93rd Edition: . CRC Press, 2012, ISBN 978-1-4398-8049-4 , pp. 420 ( limited preview in Google Book search).
↑ Jiro Tsuji: Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis . John Wiley & Sons, 2002, ISBN 978-0-471-56027-2 , pp. 183 ( limited preview in Google Book search).
↑ Philip L. Fuchs: Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis: . John Wiley & Sons, 2011, ISBN 978-0-470-71023-4 , pp. 514 ( limited preview in Google Book search).
↑ Fabrizio Cavani, Gabriele Centi, Siglinda Perathoner, Ferruccio Trifirò: Sustainable Industrial Chemistry: Principles, Tools and Industrial Examples . John Wiley & Sons, 2009, ISBN 3-527-62912-2 , pp. 83 ( limited preview in Google Book search).
^ T. Inui: Successful Design of Catalysts: Future Requirements and Development . Elsevier, 1988, ISBN 978-0-08-096077-7 , pp. 314 ( limited preview in Google Book search).
↑ kuraray: 1,9-nonanediol
^ Douglas C. Neckers, Michael P. Doyle: Organic chemistry . Wiley, 1977, ISBN 0-471-02875-4 , pp. 307 ( limited preview in Google Book search).
↑ WLF Armarego: Purification of Laboratory Chemicals . Butterworth-Heinemann, 2017, ISBN 978-0-12-805456-7 , pp. 225 ( limited preview in Google Book Search).

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f ^g data sheet 1,9-Nonanediol, 98% from Sigma-Aldrich , accessed on April 30, 2015 ( PDF ).

[Alfa-2] Data sheet 1,9-Nonanediol, 97% from AlfaAesar, accessed on April 30, 2015 ( PDF )(JavaScript required) .

[William_M._Haynes-3] William M. Haynes: CRC Handbook of Chemistry and Physics, 93rd Edition: . CRC Press, 2012, ISBN 978-1-4398-8049-4 , pp. 420 ( limited preview in Google Book search).

[Jiro_Tsuji-4] Jiro Tsuji: Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis . John Wiley & Sons, 2002, ISBN 978-0-471-56027-2 , pp. 183 ( limited preview in Google Book search).

[Philip_L._Fuchs-5] Philip L. Fuchs: Handbook of Reagents for Organic Synthesis, Reagents for Silicon-Mediated Organic Synthesis: . John Wiley & Sons, 2011, ISBN 978-0-470-71023-4 , pp. 514 ( limited preview in Google Book search).

[Fabrizio_Cavani,_Gabriele_Centi,_Siglinda_Perathoner,_Ferruccio_Trifirò-6] Fabrizio Cavani, Gabriele Centi, Siglinda Perathoner, Ferruccio Trifirò: Sustainable Industrial Chemistry: Principles, Tools and Industrial Examples . John Wiley & Sons, 2009, ISBN 3-527-62912-2 , pp. 83 ( limited preview in Google Book search).

[T._Inui-7] T. Inui: Successful Design of Catalysts: Future Requirements and Development . Elsevier, 1988, ISBN 978-0-08-096077-7 , pp. 314 ( limited preview in Google Book search).

[kuraray-8] uraray: 1,9-nonanediol

[Douglas_C._Neckers,_Michael_P._Doyle-9] Douglas C. Neckers, Michael P. Doyle: Organic chemistry . Wiley, 1977, ISBN 0-471-02875-4 , pp. 307 ( limited preview in Google Book search).

[W.L.F._Armarego-10] WLF Armarego: Purification of Laboratory Chemicals . Butterworth-Heinemann, 2017, ISBN 978-0-12-805456-7 , pp. 225 ( limited preview in Google Book Search).