Naphthalene-1,5-disulfonic acid

Structural formula
General
Surname	Naphthalene-1,5-disulfonic acid
other names	Armstrong Acid; 1,5-naphthalenedisulfonic acid; 1.5 NDSA;
Molecular formula	C 1 0 H 8 O 6 S 2
Brief description	white odorless solid (tetrahydrate)
External identifiers / databases
ECHA InfoCard	100.001.199
PubChem	6666
ChemSpider	6414
Wikidata	Q3306063
properties
Molar mass	288.3 g mol −1
Physical state	firmly
density	0.9 g cm −3 (bulk density of tetrahydrate); 1.493 g cm −3 ;
Melting point	110 ° C (decomposition of tetrahydrate); 242 ° C;
Vapor pressure	51 hPa (50 ° C)
solubility	soluble in water (1030 g l −1 at 20 ° C, tetrahydrate) easily soluble in water; soluble in ethanol; practically insoluble in diethyl ether;
safety instructions
GHS labeling of hazardous substances Tetrahydrate danger
H and P phrases	H: 314
	P: 280-305 + 351 + 338-310
Toxicological data	2420 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 .

Naphthalene-1,5-disulfonic acid is a chemical compound from the group of sulfonic acids . The compound is also known as Armstrong's acid after the British chemist Henry Edward Armstrong .

Extraction and presentation

Naphthalene-1,5-disulfonic acid can be obtained by reacting naphthalene or naphthalene-1-monosulfonic acid with fuming sulfuric acid at below 25 ° C. The reaction also produces naphthalene-1,6-disulfonic acid, naphthalene-1,3,6-trisulfonic acid and naphthalene-1,3,7-trisulfonic acid. It can also be obtained by reacting naphthalene with sulfur trioxide in sulfuric acid at low temperatures.

properties

As a tetrahydrate, naphthalene-1,5-disulfonic acid is a white, odorless solid that is soluble in water.

use

Naphthalene-1,5-disulfonic acid is used as an intermediate in the manufacture of dyes. In this process, diazonium salts are stabilized with naphthalene-1,5-disulfonate as the counteranion, so that they can be isolated, dried and stored. The stabilized diazonium salts are used as so-called true salts in developing dyes . Example: Real Red Salt TR (CI Azoic Diazo Component 11)

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Data sheet naphthalene-1,5-disulfonic acid (PDF) from Merck , accessed on November 5, 2018.
↑ ^a ^b ^c ^d ^e David R. Lide: CRC Handbook of Chemistry and Physics A Ready-reference Book of Chemical and Physical Data . CRC Press, 1995, ISBN 978-0-8493-0595-5 , pp. 418 ( limited preview in Google Book search).
↑ ^a ^b Data sheet 1,5-Naphthalenedisulfonic acid tetrahydrate, 97% from Sigma-Aldrich , accessed on November 5, 2018 ( PDF ).
↑ Alexander Senning: Elsevier's Dictionary of Chemoetymology The Whys and Whences of Chemical Nomenclature and Terminology . Elsevier, 2006, ISBN 978-0-08-048881-3 , pp. 30 ( limited preview in Google Book search).
^ Houben-Weyl Methods of Organic Chemistry Vol. IX, 4th Edition Sulfur, Selenium, Tellurium Compounds . Georg Thieme Verlag, 2014, ISBN 3-13-180544-7 , p. 477 ( limited preview in Google Book search).
↑ Hans Theodor Bucherer: Textbook of color chemistry - including the extraction and processing of the tar as well as the methods for the representation of the preliminary and intermediate products . Springer-Verlag, 2013, ISBN 978-3-662-33911-4 , pp. 107 ( limited preview in Google Book search).
↑ Google Patents: EP0000155A1 - Continuous production of naphthalene-1-sulfonic acid and 1,5-disulfonic acid - Google Patents , accessed November 5, 2018.
^ SVS Rana: Biotechniques Theory & Practice . Rastogi Publications, 2008, ISBN 978-81-7133-886-3 , pp. 57 ( limited preview in Google Book search).
↑ Data sheet Fast Red TR Salt 1,5-naphthalenedisulfonate salt from Sigma-Aldrich , accessed on January 29, 2019 ( PDF ).

[Merck-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Data sheet naphthalene-1,5-disulfonic acid (PDF) from Merck , accessed on November 5, 2018.

[David_R._Lide-2] David R. Lide: CRC Handbook of Chemistry and Physics A Ready-reference Book of Chemical and Physical Data . CRC Press, 1995, ISBN 978-0-8493-0595-5 , pp. 418 ( limited preview in Google Book search).

[Sigma-3] Data sheet 1,5-Naphthalenedisulfonic acid tetrahydrate, 97% from Sigma-Aldrich , accessed on November 5, 2018 ( PDF ).

[Alexander_Senning-4] Alexander Senning: Elsevier's Dictionary of Chemoetymology The Whys and Whences of Chemical Nomenclature and Terminology . Elsevier, 2006, ISBN 978-0-08-048881-3 , pp. 30 ( limited preview in Google Book search).

[5] Houben-Weyl Methods of Organic Chemistry Vol. IX, 4th Edition Sulfur, Selenium, Tellurium Compounds . Georg Thieme Verlag, 2014, ISBN 3-13-180544-7 , p. 477 ( limited preview in Google Book search).

[Hans_Theodor_Bucherer-6] Hans Theodor Bucherer: Textbook of color chemistry - including the extraction and processing of the tar as well as the methods for the representation of the preliminary and intermediate products . Springer-Verlag, 2013, ISBN 978-3-662-33911-4 , pp. 107 ( limited preview in Google Book search).

[google.com-7] Google Patents: EP0000155A1 - Continuous production of naphthalene-1-sulfonic acid and 1,5-disulfonic acid - Google Patents , accessed November 5, 2018.

[S._V._S._Rana-8] SVS Rana: Biotechniques Theory & Practice . Rastogi Publications, 2008, ISBN 978-81-7133-886-3 , pp. 57 ( limited preview in Google Book search).

[9] Data sheet Fast Red TR Salt 1,5-naphthalenedisulfonate salt from Sigma-Aldrich , accessed on January 29, 2019 ( PDF ).