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1-Nitronaphthalene

Presented By –
Krishna Deora (204)
Manan Gupta (206)
Inderdeep Minhas (207)
Madhurya Jagarlapudi (208)
Contents
 Introduction
 Physical Properties
 Chemical Structure
 Chemical Formula & Names
 Molecular Properties
 Solid Properties
 3D Structure
 Thermodynamic Properties
 Safety Properties
 Toxicity
 Synthesis via Naphthalene
 Preparation
 Precautions
 Flow Diagram
 Oxidation
 Application
 Synthesis of 1-Naphthylamine
 Uses
 Safety Profile
 Handling & Storage
 Bibliography
Introduction
 Direct nitration of Naphthalene results in
formation of 1-nitronaphthalene.

 It appears in form of yellow crystalline


solid which melts at 61°C
Physical Properties
 It is combustible.

 It is incompatible with oxidizing agents.

 It is a strong reducing agent.

 Mixtures with sulfuric or nitric acid are


dangerous.
Chemical Structure
Chemical Formula & Names
Chemical Formula C10H7NO2

Name 1-nitronaphthalene

Alternate Names alpha-nitronaphthalene,


naphthalene, 1-nitro- , nitrol,
nitrol (pesticide)
Mass Fractions C (carbon) 69.4%,
H (hydrogen) 4.07%,
N (nitrogen) 8.09%,
O (oxygen) 18.5%
Molecular Properties
Molecular Weight 173.168 g/mol

Phase Solid (at STP)

Melting Point 55°C

Boiling Point 304°C

Density 1.223 g/cm3


Solid Properties
Index of Refraction 1.671
Molar Refractivity 50.64 cm3
Molar Volume 135.3 cm3/mol
Polarizability 20.07*10-24 cm3
Surface Tension 53.7 dyne/cm
Vapour Pressure (At STP) 0.00162 mmHg
Enthalpy of Vaporization 52.26 kJ/mol
3D Structure
Thermodynamic Properties
Latent heat of Gas=0.6422 kJ/g
formation ∆f H°
Solid=0.246 kJ/g

Latent heat of 0.384 kJ/g


vaporization

Latent heat of 28.78 kJ/g


combustion
Safety Properties

Flash Point 164°C

Auto ignition 450°C


Point
Toxicity

ORL-RAT LD50 120 mg/kg

IPR-RAT LD50 86 mg/kg


Synthesis via Naphthalene
Preparation
581 kg of naphthalene is suspended in 2041 kg of
dilute sulfuric acid or spent acid containing about
65% H2SO4. The whole mixture is thoroughly
stirred and 1066 kg of mixed acid is slowly
added. During the addition of the acid, the
temperature is kept at 35-50°C; but after the
whole of the acid has been run in, the
temperature is raised slowly to 65-70°C and
maintained at that point for 1 hr. The agitation is
then stopped, and the nitronaphthalene which
floats on the surface is decanted with part of the
spent acid and delivered to a separator, a “heel”
of acid being left for next nitration.
After settling for 3 hr, the spent acid is
removed and the crude nitronaphthalene is
delivered to the washing and granulation kettle.
Here it is made free of acid by repeated
washings with boiling water and alkali. Any free
naphthalene that may be present is removed by
steam during washing process. The crystallizing
point must be between 52 and 52.5°C. The
purification of the crude product is
accomplished also by recrystallizing it from 10%
of its weight of ligroin or solvent naphtha.
Precautions
The reaction takes place vigorously; and
unless precautions are taken, polynitro
compounds are formed. If impure
naphthalene is used, the nitration product
will be unsatisfactory; and in as much as it
is difficult to isolate 1-nitronaphthalene in a
pure state, it is advisable to prevent further
complications and to use a pure raw
material.
Flow Diagram
Oxidation

Oxidation of 1-nitronaphthalene results in the


formation of 3-nitrophthalic Acid in a
temperature range of 363-373K
Application
 1-nitronaphthalene is used as for the
preparation of dye intermediate such as
1-naphthylamine (by catalytic reduction)

 1-nitronaphthalene is also used as a


component in the formulation of nitrate
explosives to decrease the burning rate.
Synthesis of 1-Naphthylamine
Uses
1-nitronaphthalene can be used as
intermediates for :

 Fuel
 Pesticides
 Rubber Chemicals
 Organic Synthesis
Safety Profile
 Poison by intraperitoneal route.
 Flammable solid and combustible liquid
when exposed to heat or flame.
 Explosive reaction with nitric acid +
sulfuric acid above 60°C
 Forms a sensitive explosive mixture with
tetranitromethane.
 When heated to decomposition it emits
toxic fumes of NOx
Handling & Storage
 Wash hands thoroughly after handling.

 Remove contaminated clothing and wash


before reuse.

 Avoid contact with eyes, skin, and


clothing.

 Avoid ingestion and inhalation.


 Keep away from water and storage at 2-
8°C

 Wear safety glasses and chemical goggles


if splashing is possible.

 Wear appropriate protective clothing to


minimize contact with skin.
Bibliography
 http://www.google.co.in/imghp?hl=en&ta
b=wi

 http://www.lookchem.com/1-
Nitronaphthalene/

 http://ochemisty.blogspot.com/2009/03/n
itration-of-naphthalene.html
 http://www.wolframalpha.com/input/?i=1
-
nitronaphthalene&lk=1&a=ClashPrefs_*
Chemical.1Nitronaphthalene-

 http://www.chemspider.com/Chemical-
Structure.6588.html

 Unit Processes In Organic Synthesis –


Groggins