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Naphthalene

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Name

Naphthalene

EINECS 202-049-5
CAS No. 91-20-3 Density 1.037 g/cm3
PSA 0.00000 LogP 2.83980
Solubility H2O: 30 mg/L (25 °C) Melting Point 80-82 °C(lit.)
Formula C10H8 Boiling Point 221.5 °C at 760 mmHg
Molecular Weight 128.18 Flash Point 78.9 °C
Transport Information UN 1334 4.1/PG 3 Appearance white to almost white crystals, crystalline flakes
Safety 36/37-46-60-61-62-45-16-7 Risk Codes 22-40-50-67-65-38-11-39/23/24/25-52/53
Molecular Structure Molecular Structure of 91-20-3 (Naphthalene) Hazard Symbols HarmfulXn, DangerousN, FlammableF, ToxicT
Synonyms

Albocarbon;Camphor tar;Dezodorator;Naftalen;

 

Naphthalene Synthetic route

119-64-2

tetralin

91-20-3

naphthalene

Conditions
ConditionsYield
With triisobutylaluminum; Co acetylacetonate In neat (no solvent) at 150 - 200℃; Product distribution; other solvent, catalyst and reagent; turnover time and inhibition of reaction and catalyst;100%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 1.33333h; Reflux;62%
With phenyl isocyanate; palladium on activated charcoal at 220℃; for 6h;57%
17743-32-7

5-(2-Naphthyloxy)-1-phenyl-1H-tetrazole

91-20-3

naphthalene

Conditions
ConditionsYield
With ethanol; water; tetrabutylammonium hypophosphite; benzene; palladium on activated charcoal for 3h; Product distribution; hydrogenation in a biphasic solvent system, other H-donor, other time, different amounts of substrate or catalyst, addition of 18-crown-6-ether;100%
1131-16-4

3,5-dimethyl-1-phenyl-1H-pyrazole

91-20-3

naphthalene

Conditions
ConditionsYield
at 920℃; under 0.7 Torr; for 1.66667E-05h; Mechanism; flash vacuum thermolysis;100%
75896-23-0

1-Methoxy-1.2-dihydronaphthalin

91-20-3

naphthalene

Conditions
ConditionsYield
With silica gel100%
62131-91-3

2,3,6,7-tetrakis(trimethylsilyl)naphthalene

91-20-3

naphthalene

Conditions
ConditionsYield
With trifluoroacetic acid In tetrachloromethane for 12h; Ambient temperature;100%
135447-30-2

3-benzotellurepine

91-20-3

naphthalene

Conditions
ConditionsYield
for 72h; Product distribution; Ambient temperature; other tellurepines;100%
In (2)H8-toluene at 40.3℃; Kinetics; Further Variations:; Temperatures;100%
75896-22-9

1-methoxy-1,4-dihydronaphthalene

91-20-3

naphthalene

Conditions
ConditionsYield
With silica gel100%
90-13-1

1-Chloronaphthalene

91-20-3

naphthalene

Conditions
ConditionsYield
With water; sodium iodide; nickel dichloride; zinc; sonication In N,N,N,N,N,N-hexamethylphosphoric triamide at 60℃; for 8h; Product distribution;100%
With water; sodium iodide; nickel dichloride; zinc; sonication In N,N,N,N,N,N-hexamethylphosphoric triamide at 60℃; for 8h;100%
With ammonium formate In water at 20℃; for 6h;99%
617-86-7

triethylsilane

(2RS,3RS,4RS,5RS,6RS,7RS)-3,6-dimesityl-3,6-bis<2,4,6-trisphenyl>-3,6-disilatetracyclo<6.4.02,4.05,7>dodeca-1(8),9,11-triene

A

91-20-3

naphthalene

B

2-<2,4,6-trisphenyl>-1,1,1-triethyl-2-mesityldisilane

Conditions
ConditionsYield
In (2)H8-toluene at 120℃; for 30h;A n/a
B 100%
264-14-2

Benzo[d]thiepine

91-20-3

naphthalene

Conditions
ConditionsYield
In (2)H8-toluene at 23℃; Kinetics; Further Variations:; Temperatures;100%

7-Selena-benzocycloheptene

91-20-3

naphthalene

Conditions
ConditionsYield
In (2)H8-toluene at 22.8℃; Kinetics; Further Variations:; Temperatures;100%

7-Phenyl-7H-7-arsa-benzocycloheptene

91-20-3

naphthalene

Conditions
ConditionsYield
In (2)H8-toluene at 22.3℃; Kinetics; Further Variations:; Temperatures;100%
75-21-8

oxirane

(naphthalene)Yb(THF)3

A

91-20-3

naphthalene

B

110-63-4

Butane-1,4-diol

C

ytterbium hydroxide

Conditions
ConditionsYield
With hydrogen cation In tetrahydrofuran shaken for 10 min at room temp.; centrifuged, decanted, soln. contains naphthalene, pptn. hydrolysed in THF: butanediol detd. by GLC in the organic layer and a pptn. (Yb(OH)3);A 83%
B 100%
C 75%
79909-37-8

1,2,3,4-tetrahydronaphthalene-1,4-diacetate

91-20-3

naphthalene

Conditions
ConditionsYield
at 80 - 180℃; under 40 Torr;99.8%
90-11-9

1-Bromonaphthalene

91-20-3

naphthalene

Conditions
ConditionsYield
With lithium aluminium tetrahydride In 1,2-dimethoxyethane at 35℃; for 6h; ultrasonic acceleration of reduction;99%
With 2,2'-azobis(isobutyronitrile); tert-butyl(2,6-dimethoxy-1-methylcyclohexa-2,5-dien-1-yl)dimethylsilane In hexane for 18h; Heating;99%
With 2,2'-azobis(isobutyronitrile); tert-butyl(2,6-dimethoxy-1-methylcyclohexa-2,5-dien-1-yl)dimethylsilane In hexane for 18h; Heating;99%
321-38-0

1-Fluoronaphthalene

91-20-3

naphthalene

Conditions
ConditionsYield
With palladium 10% on activated carbon In isopropyl alcohol at 100℃; for 12h; Inert atmosphere;99%
With C32H46N2Ru; sodium carbonate; isopropyl alcohol at 70℃; for 96h; Inert atmosphere; Schlenk technique; Glovebox;96%
With s-butylmagnesium chloride; bis(cyclopentadienyl)titanium dichloride In tetrahydrofuran at 50℃; for 12h; Product distribution / selectivity;88%
90-14-2

1-Iodonaphthalene

91-20-3

naphthalene

Conditions
ConditionsYield
With lithium aluminium tetrahydride In 1,2-dimethoxyethane at 35℃; for 6h; ultrasonic acceleration of reduction;99%
With formaldehyd; palladium diacetate; caesium carbonate In dimethyl sulfoxide at 80℃; for 12h; Kinetics; Reagent/catalyst;99%
With tri-n-butyl-tin hydride In acetonitrile at 20℃; for 24h; Irradiation; Inert atmosphere;97%
2216-69-5

1-Methoxynaphthalene

91-20-3

naphthalene

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel(0); (dimethoxy)methylsilane; tricyclohexylphosphine In toluene at 80℃; for 12h; Inert atmosphere;99%
With bis(1,5-cyclooctadiene)nickel(0); 1,1,3,3-Tetramethyldisiloxane; tricyclohexylphosphine In toluene at 110℃; for 14h; Inert atmosphere;77%
Multi-step reaction with 2 steps
1: NaBH4,m-dicyanobenzene / acetonitrile; H2O / 7 h / Irradiation
2: 100 percent / silica gel
View Scheme
33397-22-7

tri(naphthalen-1-yl)bismuth

A

91-20-3

naphthalene

B

642-29-5

1-benzoylnaphthalene

C

7787-60-2

bismuth(III) chloride

Conditions
ConditionsYield
With aluminium trichloride; benzoic acid In chloroform 5 h reflux, molar ratio Bi(1-C10H7)3:AlCl3:C6H5COOH = 1:1:1;A 34%
B 9.3%
C 99%
With iron(III) chloride; benzoic acid In chloroform 5 h reflux, molar ratio Bi(1-C10H7)3:FeCl3:C6H5COOH = 1:1:1;A 44%
B 10.2%
C 96%
93-04-9

2-Methoxynaphthalene

91-20-3

naphthalene

Conditions
ConditionsYield
With triethylsilane; bis(1,5-cyclooctadiene)nickel (0); tricyclohexylphosphine In toluene at 110℃; for 14h; Reagent/catalyst; Concentration; Solvent;99%
With isopropylmagnesium bromide; nickel diacetate; 1,3-dicyclohexyl-1H-imidazol-3-ium chloride In tetrahydrofuran at 100℃; for 18h; Inert atmosphere; Sealed tube;70%
With bis(1,5-cyclooctadiene)nickel (0); sodium formate; 1,3-dicyclohexyl-1H-imidazol-3-ium chloride; sodium t-butanolate In toluene at 140℃; for 24h; Reagent/catalyst; Inert atmosphere; Schlenk technique;63%
33397-22-7

tri(naphthalen-1-yl)bismuth

A

91-20-3

naphthalene

B

7787-60-2

bismuth(III) chloride

Conditions
ConditionsYield
With benzoic acid In chloroform molar ratio Bi(1-C10H7)3:C6H5COOH = 1:1;A 49.1%
B 98.4%
With AlCl3 or FeCl3 In chloroform reflux;A 36-46
B >97
99747-74-7

1-naphthyl triflate

91-20-3

naphthalene

Conditions
ConditionsYield
With formic acid; triethylamine; palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 65℃; for 12h;98%
With triethylammonium formate; palladium diacetate; 1,3-bis-(diphenylphosphino)propane In N,N-dimethyl-formamide at 18℃; for 0.8h; Product distribution; other catalysts, variation of temperature;92%
With lithium; nickel dichloride In tetrahydrofuran for 4h; Reduction; Heating;21%
Multi-step reaction with 3 steps
1.1: iron(II) acetate; N,N,N,N,-tetramethylethylenediamine; sodium t-butanolate; bis(pinacol)diborane / di-isopropyl ether / 120 °C
2.1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C
2.2: 20 °C
3.1: C66H60BFeO2P4; N,N,N,N,-tetramethylethylenediamine; sodium t-butanolate / di-isopropyl ether; hexane; tetrahydrofuran / 15 h / 120 °C / Schlenk technique; Glovebox
View Scheme
101916-87-4

trans-4-deuterio-1,4-dihydro-1-methoxynaphthalene

A

91-20-3

naphthalene

B

875-62-7

1-deuteronaphthalene

Conditions
ConditionsYield
With lithium diisopropyl amide In hexane for 0.5h; Product distribution; other solvents, bases;A 2%
B 98%
98-86-2

acetophenone

90-13-1

1-Chloronaphthalene

A

91-20-3

naphthalene

B

16216-08-3

2-(naphthalen-1-yl)-1-phenylethan-1-one

Conditions
ConditionsYield
With sodium amalgam; potassium tert-butylate; ammonia for 2h;A n/a
B 98%

(naphthalene)Yb2(THF)3(NaCl)3

A

ytterbium(III) oxide

B

91-20-3

naphthalene

C

7647-14-5

sodium chloride

Conditions
ConditionsYield
With air In tetrahydrofuran stirred for 18 h under dry air; centrifuged, washed with benzene and water (Yb2O3), naphthalene detd. by GLC in the organic layer, aq. soln. contains NaCl;A 98%
B 98%
C 96%

(naphthalene)Yb2(THF)3(NaCl)3

A

ytterbium(III) oxide

B

91-20-3

naphthalene

Conditions
ConditionsYield
With oxygen In tetrahydrofuran 18 h at room temp.;A 96%
B 98%

(1S,4S,5S,8S)-tetrabromo-1,2,3,4,5,6,7,8-octahydronaphthalene

91-20-3

naphthalene

Conditions
ConditionsYield
at 150℃; for 120h; Aromatisation;97%
86-55-5

1-naphthalenecarboxylic acid

91-20-3

naphthalene

Conditions
ConditionsYield
With triethylsilane; palladium diacetate; 2,2-dimethylpropanoic anhydride; 1,4-di(diphenylphosphino)-butane In toluene at 160℃; for 15h; chemoselective reaction;97%
With water; palladium on activated charcoal at 250℃; under 30002.4 - 37503 Torr; for 14h;74%
With methanol at 40℃; for 48h; Schlenk technique; Irradiation; Inert atmosphere;70%
66-99-9

β-naphthaldehyde

91-20-3

naphthalene

Conditions
ConditionsYield
With palladium nanoparticles supported on fibrous silica In cyclohexane at 130℃; for 20h; Molecular sieve;97%
With palladium diacetate In cyclohexane at 140℃; for 24h; Molecular sieve; air;82%
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; triphenylphosphine In 1,4-dioxane at 110℃; for 48h; Inert atmosphere;95 %Chromat.
1503-86-2

2-naphthyl pivalate

91-20-3

naphthalene

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); sodium formate; 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 140℃; for 24h; Temperature; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique;97%
With bis(1,5-cyclooctadiene)nickel(0); 1,1,3,3-Tetramethyldisiloxane; tricyclohexylphosphine In toluene at 110℃; for 10h; Inert atmosphere;81 %Chromat.
With bis(1,5-cyclooctadiene)nickel(0); (dimethoxy)methylsilane; tricyclohexylphosphine In toluene at 80℃; for 12h; Inert atmosphere;99 %Chromat.
Multi-step reaction with 2 steps
1: toluene / 90 °C / Inert atmosphere; Schlenk technique
2: sodium formate / toluene / 24 h / 120 °C / Inert atmosphere; Schlenk technique
View Scheme
91-20-3

naphthalene

85-44-9

phthalic anhydride

Conditions
ConditionsYield
With oxygen100%
With oxygen100%
With oxygen100%
91-20-3

naphthalene

A

85-44-9

phthalic anhydride

B

130-15-4

[1,4]naphthoquinone

Conditions
ConditionsYield
With oxygen at 340 - 360℃; Product distribution / selectivity;A 100%
B 0.05%
With oxygen at 340 - 360℃;A 100%
B 0.1%
With oxygen at 340 - 360℃;A 100%
B 0.02%
91-20-3

naphthalene

119-64-2

tetralin

Conditions
ConditionsYield
With sodium; tert-butyl alcohol In tetrahydrofuran for 15h; Heating;100%
With Raney nickel; isopropyl alcohol at 82℃; for 1h; Temperature; Inert atmosphere;99%
With cobalt(II) chloride hexahydrate; lithium In tetrahydrofuran at 25℃; for 3h; Birch reaction; Inert atmosphere;98%
91-20-3

naphthalene

91-17-8

decalin

Conditions
ConditionsYield
With Ti8O8(14+)*6C8H4O4(2-)*4O(2-)*3.3Li(1+)*0.7Co(2+)*0.7C4H8O*0.7H(1-); hydrogen In neat (no solvent) at 120℃; under 37503.8 Torr; for 18h;100%
With hydrogen In cyclohexane at 100℃; under 33603.4 Torr; for 1h; Catalytic behavior; Temperature; Autoclave;99%
With nickel(II) oxide; hydrogen; palladium In hexane at 150℃; under 37503.8 Torr; for 36h;93%
91-20-3

naphthalene

625-36-5

2-chloropropionyl chloride

22422-70-4

3-chloro-1-(naphthalen-2-yl)propan-1-one

Conditions
ConditionsYield
With aluminum (III) chloride In dichloromethane at 20℃; Cooling with ice;100%
With carbon disulfide; aluminium trichloride
With aluminium trichloride In nitrobenzene 1.) 5 h, room temp., 2.) 30 min, 40-45 deg C;
Stage #1: naphthalene; 2-chloropropionyl chloride With aluminum (III) chloride In nitrobenzene at 0℃;
Stage #2: With hydrogenchloride In nitrobenzene
91-20-3

naphthalene

509-14-8

tetranitromethane

146850-06-8

1-Nitro-4-trinitromethyl-1,4-dihydro-naphthalene

Conditions
ConditionsYield
In dichloromethane at 23℃; for 24h;100%
91-20-3

naphthalene

145628-18-8, 56078-31-0

ethyl 2-chloro-2-methylthio-acetate

75286-85-0

ethyl α-methylthio-1-naphthaleneacetate

Conditions
ConditionsYield
tin(IV) chloride In dichloromethane for 0.666667h; Ambient temperature;100%
tin(IV) chloride In dichloromethane for 0.666667h; Ambient temperature; Yield given;
91-20-3

naphthalene

51268-88-3

(1R,2S)-1,2-dihydronaphthalene-1,2-diol

Conditions
ConditionsYield
With toluene dioxygenase; oxygen Enzymatic reaction; regioselective reaction;100%
With toluene dioxygenase from Pseudomonas putida F1 variant A223V In ethanol at 30℃; for 0.5h; Enzymatic reaction; enantioselective reaction;62.7%
Pseudomonas putida UV4;
91-20-3

naphthalene

6972-27-6

1,3-Dimethyl-6-chlorouracil

4097-20-5

6-methoxy-1,3-dimethyluracil

Conditions
ConditionsYield
In methanol at 20℃; for 1h; UV-irradiation;100%
91-20-3

naphthalene

(Cp*Ru)2(μ-NHPh)(μ-hydride)(μ-η2:η2-C7H8)

[(Cp*Ru)2(μ-NHPh)(μ-H)(μ-η2:η2-naphthalene)]

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 1h; Schlenk technique; Inert atmosphere;100%
623-73-4

diazoacetic acid ethyl ester

91-20-3

naphthalene

exo-ethyl 2,3-benzo-2,4-norcaradiene-7-carboxylate

Conditions
ConditionsYield
With Ag3(μ2-(3,5-(CF3)2PyrPy))3 In dichloromethane at 20℃; Buchner Ring Enlargement;100%
623-73-4

diazoacetic acid ethyl ester

91-20-3

naphthalene

13612-37-8

ethyl 1a,7b-dihydro-1H-cyclopropa[a]naphthalene-1-carboxylate

Conditions
ConditionsYield
With chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I); sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 60℃; for 24h; Inert atmosphere;99%
With copper(II) sulfate at 150℃; for 4h;20%
at 140 - 145℃;
With rhodium (II) octanoate dimer In 1,2-dichloro-ethane at 25℃; for 0.333333h;55 %Spectr.
91-20-3

naphthalene

86-57-7

1-Nitronaphthalene

Conditions
ConditionsYield
With bismuth(III) nitrate; Montmorillonite KSF for 0.166667h; Nitration;99%
With benzyltriphenylphosphonium nitrate; Methanesulfonic anhydride at 20℃; for 0.333333h;99%
With In(OSO2CF3)3; nitric acid at 20 - 60℃; for 24h;98%
91-20-3

naphthalene

75-36-5

acetyl chloride

A

941-98-0

1'-naphthacetophenone

B

93-08-3

methyl 2-naphthyl ketone

Conditions
ConditionsYield
aluminium trichloride In 1,2-dichloro-ethane at 0℃; Rate constant; Kinetics; Mechanism; other temperature; other concentrations;A 99%
B 1%
aluminium trichloride In 1,2-dichloro-ethane at 0℃; Thermodynamic data; ΔH<*>(activation); Σ<*>(activation);A 99%
B 1%
With aluminium trichloride; 1-ethyl-3-methyl-1H-imidazol-3-ium chloride at 0℃; for 1h;A 89%
B 2%

Naphthalene Chemical Properties

Molecular Structure:

IUPAC Name: Naphthalene
Synonyms of Naphthalene (CAS NO.91-20-3): Albocarbon ; Camphor tar ; Dezodorator ; Naftalen ; Naphthalene ; Naphthaline ; Naphthalene, crude or refined ; Naphthalene, molten
CAS NO: 91-20-3
Molecular Formula: C10H8
Molecular Weight: 128.17
EINECS: 202-049-5
Index of Refraction: 1.632
Molar Refractivity: 44.09 cm3
Molar Volume: 123.5 cm3
Surface Tension: 40.2 dyne/cm
Density: 1.037 g/cm3
Flash Point: 78.9 °C
Enthalpy of Vaporization: 43.93 kJ/mol
Boiling Point: 221.5 °C at 760 mmHg
Vapour Pressure: 0.159 mmHg at 25°C
Melting Point: 80-82 °C(lit.)
Storage temp: APPROX 4°C
Water Solubility: 30 mg/L (25 °C)
Appearance: white to almost white crystals, crystalline flakes
Product Categories of Naphthalene (CAS NO.91-20-3): Intermediates of Dyes and Pigments;Naphthalene;Organoborons;Highly Purified Reagents;Other Categories;Zone Refined Products;Analytical Chemistry;Standard Solution of Volatile Organic Compounds for Water & Soil Analysis;Standard Solutions (VOC);Chemistry;Naphthalenes;Analytical Standards;AromaticsVolatiles/ Semivolatiles;Volatiles/ Semivolatiles;Arenes;Building Blocks;Organic Building Blocks;Alpha Sort;Chemical Class;FumigantsVolatiles/ Semivolatiles;Hydrocarbons;Insecticides;N;NA - NIAnalytical Standards;NaphthalenesChemical Class;Neats;N-OAlphabetic;Pesticides

Naphthalene History

In 1819-1820, at least two chemists reported a white solid with a pungent odor derived from the distillation of coal tar.
In 1821, John Kidd described many of this substance's properties and the means of its production, and proposed the name naphthaline, as it had been derived from a kind of naphtha (a broad term encompassing any volatile, flammable liquid hydrocarbon mixture, including coal tar).
In 1826, naphthaline's chemical formula was determined by Michael Faraday.
The structure of two fused benzene rings was proposed by Emil Erlenmeyer in 1866, and confirmed by Carl Gr?be three years later.

Naphthalene Uses

 Naphthalene (CAS NO.91-20-3) has widely uses:
1. It can be used as a chemical intermediate, mainly used as a precursor to other chemicals.The single largest use of naphthalene is the industrial production of phthalic anhydride, although more phthalic anhydride is made from o-xylene. Naphthalene is also used in the synthesis of 2-naphthol, a precursor for various dyestuffs, pigments, rubber processing chemicals and other miscellaneous chemicals and pharmaceuticals.
2. Used as a wetting Agent/Surfactant: Alkyl naphthalene sulfonates (ANS) are used in many industrial applications as detergent wetting agents that effectively disperse colloidal systems in aqueous media. The major commercial applications are in the agricultural chemical industry, which uses Alkyl naphthalene sulfonates (ANS) for wettable powder and wettable granular (dry-flowable) formulations, and the textile and fabric industry, which utilizes the wetting and defoaming properties of Naphthalene for bleaching and dyeing operations.
3. Naphthalene can be used as a fumigant,this is the most familiar use of Naphthalene,such as in mothballs although 1,4-dichlorobenzene (or p-dichlorobenzene) is now more widely used.
4. Niche applications:It is used in pyrotechnic special effects such as the generation of black smoke and simulated explosions.

Naphthalene Production

 Naphthalene (CAS NO.91-20-3) is produced from coal tar. In the coal tar process, coal tar is processed through a tar-distillation step where approximately the first 20 wt % of distillate (chemical oil) is removed. The chemical oil, which contains practically all the naphthalene present in the tar, is reserved for further processing, and the remainder of the tar is distilled further to remove additional creosote oil fractions until a coal-tar pitch of desirable consistency and properties is obtained. The chemical oil is processed to remove the tar acids by contacting with dilute sodium hydroxide and, in a few cases, is next treated to remove tar bases by washing with sulfuric acid.
 Crude naphthalene product is obtained by fractional distillation of the tar acid-free chemical oil, and the distillation may be accomplished in either a batch process or a continuous process. The tar acid-free chemi-cal oil is charged to the system, where most of the low boiling components such as benzene, xylene, and toluene, are removed in the light-solvent col-umn. The chemical oil next is fed to the solvent column, which is operated under vacuum, where a product containing the prenaphthalene components is taken overhead. This product, which is called coal-tar naphtha or crude heavy solvent, typically has a boiling range of approximately 130 to 200 °C and is used as a general solvent and as a feedstock for hydrocarbon-resin manufacture because of its high content of compounds such as indene and coumarone.
The naphthalene-rich bottoms from the solvent column then are fed to the naphthalene column where a naphthalene product (95% naphthalene) is produced. The naphthalene column is operated at near atmospheric pressure to avoid difficulties that are inherent to vacuum distillation of this product, for example, naphthalene-filled vacuum jets and lines. A side stream that is rich in methylnaphthalenes may be taken near the bottom of the naphthalene column.
 The main impurity in crude 78 °C coal-tar naphthalene is sulfur that is present in the form of thionaphthene (1 to 3%). Methyl- and dimethyl-naphthalenes also are present (1 to 2%) with lesser amounts of indene, methylindenes, tar acids, and tar bases.

Naphthalene Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo oral 1gm/kg (1000mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
child LDLo oral 100mg/kg (100mg/kg)   "Toxicology and Biochemistry of Aromatic Hydrocarbons," Gerarde, H., New York, Elsevier, 1960Vol. -, Pg. 228, 1960.
dog LDLo oral 400mg/kg (400mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
guinea pig LD50 oral 1200mg/kg (1200mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 47(11), Pg. 78, 1982.
human LDLo unreported 29mg/kg (29mg/kg)   Yakkyoku. Pharmacy. Vol. 31, Pg. 1499, 1980.
man LDLo unreported 74mg/kg (74mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse LD50 intraperitoneal 150mg/kg (150mg/kg)   National Technical Information Service. Vol. AD691-490,
mouse LD50 intravenous 100mg/kg (100mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#00203,
mouse LD50 oral 316mg/kg (316mg/kg)   Weisheng Dulixue Zazhi. Journal of Health Toxicology. Vol. 4, Pg. 243, 1990.
mouse LD50 subcutaneous 969mg/kg (969mg/kg) BEHAVIORAL: TREMOR Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 20, Pg. 772, 1973.
rabbit LD50 skin > 20gm/kg (20000mg/kg)   National Technical Information Service. Vol. AD-A062-138,
rabbit LDLo oral 3gm/kg (3000mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935.
rat LC50 inhalation > 340mg/m3/1H (340mg/m3) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets. Vol. 16-4/1970,
rat LD50 oral 490mg/kg (490mg/kg)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 89, 1982.
rat LD50 skin > 2500mg/kg (2500mg/kg)   Toxicology and Applied Pharmacology. Vol. 14, Pg. 515, 1969.

Naphthalene Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program. Community Right-To-Know List.

Naphthalene Safety Profile

Hazard Codes: HarmfulXn,DangerousN,FlammableF,ToxicT
Risk Statements: 22-40-50-67-65-38-11-39/23/24/25-52/53
R11: Highly flammable. 
R22: Harmful if swallowed. 
R38: Irritating to skin. 
R40: Limited evidence of a carcinogenic effect. 
R50: Very toxic to aquatic organisms. 
R65: Harmful: may cause lung damage if swallowed.
R67: Vapours may cause drowsiness and dizziness. 
R52/53: Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R39/23/24/25: Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed
Safety Statements: 36/37-46-60-61-62-45-16-7
S36/37: Wear suitable protective clothing and gloves. 
S46: If swallowed, seek medical advice immediately and show this container or label. 
S60: This material and its container must be disposed of as hazardous waste. 
S61: Avoid release to the environment. Refer to special instructions / safety data sheets. 
S62: If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label. 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S16: Keep away from sources of ignition. 
S7: Keep container tightly closed.
RIDADR: UN 1334 4.1/PG 3
WGK Germany: 3
RTECS: QJ0525000
HazardClass: 4.1
PackingGroup: III
HS Code: 29029010

Naphthalene Standards and Recommendations

OSHA PEL: TWA 10 ppm; STEL 15 ppm
ACGIH TLV: TWA 10 ppm; STEL 15 ppm; Not Classifiable as a Human Carcinogen
DFG MAK: Confirmed Animal Carcinogen with Unknown Relevance to Humans
DOT Classification:  4.1; Label: Flammable Solid

Naphthalene Analytical Methods

For occupational chemical analysis use OSHA: #35 or NIOSH: Hydrocarbons, Aromatic, 1501.

Naphthalene Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Dusts at sufficient concentrations can form explosive mixtures with air. Will burn if involved in a fire. Use water spray to keep fire-exposed containers cool. Combustible solid.
Extinguishing Media: Use carbon dioxide or dry chemical 
Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Use spark-proof tools and explosion proof equipment. Take precautionary measures against static discharges. Do not get on skin or in eyes. Do not ingest or inhale. Use only in a chemical fume hood.
Storage: Keep Naphthalene (CAS NO.91-20-3) away from sources of ignition. Store in a cool, dry, well-ventilated area away from incompatible substances.

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