Ethyl 2-naphthyl ether

Structural formula
General
Surname	Ethyl 2-naphthyl ether
other names	2-ethoxynaphthalene; Bromelia; New nerolin; Nerolin II;
Molecular formula	C 12 H 12 O
Brief description	colorless, crystalline solid
External identifiers / databases
EC number	202-226-7
ECHA InfoCard	100.002.025
PubChem	7129
ChemSpider	6862
Wikidata	Q1371468
properties
Molar mass	172.23 g mol −1
Physical state	firmly
density	1.0640 g cm −3 (20 ° C )
Melting point	37.5 ° C
boiling point	282 ° C
solubility	almost insoluble in water; slightly soluble in propylene glycol ; soluble in organic solvents, ethanol, diethyl ether, toluene, ligroin and carbon disulfide;
Refractive index	1.5975 (36 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315
	P: no P-phrases
Toxicological data	3110 mg kg −1 ( LD 50 , rat , oral )
	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

Ethyl-2-naphthylether is a chemical compound that is derived from 2-naphthol . The phenol ether is used as a fragrance in the perfume industry .

properties

The colorless crystals of ethyl 2-naphthyl ether are not soluble in water, slightly in propylene glycol , but readily soluble in many in organic solvents such as ethanol and carbon disulfide . The enthalpy of formation is −134 kJ mol ⁻¹ , the enthalpy of combustion is −6303 kJ mol ⁻¹

Manufacturing

The preparation may be by means of the Williamson's ether synthesis from Natriumnaphtholat with bromoethane or diethyl sulfate with ethanol, and as well as the reaction of 2-naphthol sulfuric acid carried.

use

Ethyl-2-naphthylether has an odor of orange blossom and - when strongly diluted - a taste of strawberries. Therefore the ether is widely used in perfumery and cosmetics . In foods such as baked goods, chewing gum, beverages, puddings and sweets, the flavor is used in concentrations between 0.1 and a maximum of 16.4 ppm . The permitted daily dose ( "ADI" , in the USA "FEMA PADI" ) is 2.56 mg / day. Total consumption in the USA in 2001 was around 5 tons, mainly as an odorous substance in soaps and detergents, cosmetic products and perfumes; In 2004, only 3 kg were used as a flavoring in foods.

Individual evidence

↑ ^a ^b Data sheet Ethyl-2-naphthylether from AlfaAesar, accessed on December 15, 2010 ( PDF )(JavaScript required) .
↑ ^a ^b ^c ^d ^e ^f George A. Burdock: Fenaroli's handbook of flavor ingredients . 5th edition. CRC Press, 2005, ISBN 978-0-8493-3034-6 , pp. 1353-1354 .
↑ ^a ^b ^c ^d ^e ^f 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. 3-236.
↑ ^a ^b ^c RÖMPP . 9th edition. 1995, ISBN 3-13-102759-2 , pp. 1261 .
↑ ^a ^b Datasheet Nerolin bromelia from Sigma-Aldrich , accessed on March 31, 2011 ( PDF ).
↑ Ignatius Valerius Stanley Stanislaus: American Soap Maker's Guide. HC Baird & Company, Incorporated, 1928, p. 593 ( limited preview in Google book search).
↑ Colomina, M .; Roux, MV; Turrion, C .: Thermochemical properties of naphthalene compounds. IV. Enthalpies of combustion and formation of 2-methoxynaphthalene, 2-ethoxynaphthalene, and 2,3- and 2,7-dihydroxynaphthalenes in J. Chem. Thermodyn. 8 (1976) pp. 869-872.
↑ Irving S. Rossoff: Encyclopedia of clinical toxicology: a comprehensive guide and reference to the toxicology of prescription and OTC drugs, chemicals, herbals, plants, fungi, marine life, reptiles and insect venoms, food ingredients, clothing, and environmental toxins. Informa Health Care, 2002, ISBN 978-1-84214-101-4 , p. 432.

[alfa-1] Data sheet Ethyl-2-naphthylether from AlfaAesar, accessed on December 15, 2010 ( PDF )(JavaScript required) .

[fenaroli-2] ↑ ^a ^b ^c ^d ^e ^f George A. Burdock: Fenaroli's handbook of flavor ingredients . 5th edition. CRC Press, 2005, ISBN 978-0-8493-3034-6 , pp. 1353-1354 .

[CRC90_3_236-3] ↑ ^a ^b ^c ^d ^e ^f 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. 3-236.

[RÖMPP-4] RÖMPP . 9th edition. 1995, ISBN 3-13-102759-2 , pp. 1261 .

[Sigma-5] Datasheet Nerolin bromelia from Sigma-Aldrich , accessed on March 31, 2011 ( PDF ).

[6] Ignatius Valerius Stanley Stanislaus: American Soap Maker's Guide. HC Baird & Company, Incorporated, 1928, p. 593 ( limited preview in Google book search).

[7] Colomina, M .; Roux, MV; Turrion, C .: Thermochemical properties of naphthalene compounds. IV. Enthalpies of combustion and formation of 2-methoxynaphthalene, 2-ethoxynaphthalene, and 2,3- and 2,7-dihydroxynaphthalenes in J. Chem. Thermodyn. 8 (1976) pp. 869-872.

[8] Irving S. Rossoff: Encyclopedia of clinical toxicology: a comprehensive guide and reference to the toxicology of prescription and OTC drugs, chemicals, herbals, plants, fungi, marine life, reptiles and insect venoms, food ingredients, clothing, and environmental toxins. Informa Health Care, 2002, ISBN 978-1-84214-101-4 , p. 432.