Lourdes Patricia L.

Carreon Zaborah Eunice Bobadilla, Nerissa Unielle Quenga, Bernadette Toledo

February 21, 2012

Synthesis of 1-Phenylazo-2-naphthol
I. Objective
to synthesize 1-phenylazo-2-naphtol through diazotization and coupling reactions

II. Schematic Diagram of Procedure

0.2 mL aniline + 0.35 mL water + 0.5 mL conc HCl in 50 mL Erlenmeyer flask

A. Preparation of phenyldiazonium chloride solution cool to 4C + approx 1 mL ice-cold distilled water +0.3 g NaNO2 crystal and keep temp of mixture below 5C

B. Preparation of -naphtol solution

dissolve 0.35 g -naphtol in 4.5 mL 5% aq NaOH in 50 mL beaker

cool to 4C

C. Ingrain Dyeing
2 x 3 cm fabric in cold -naphtol solution (immersed in ice bath) soak fiber for 2-3 mins remove fabric and then dry using filter papers

note the result

remove fabric from solution and rinse in running water

immerse fabric in phenyldiazonium chloride solution

D. Synthesis of Sudan-1
remaining phenyldiazonium chloide solution + naphthol solution allow mixture to stand at 4C for 1-5 mins filter product and wash thoroughly with small portions of cold water

dry and determine the melting point of recrystallized product

recrystallize crude product with minimal amount of hot ethanol in a steam bath

III. Table of Reagents and Products

Reagent/Produ ct Structure Physical Properties Hazards Eye: May cause lacrimation (tearing), blurred vision, and photophobia. Skin: Causes moderate skin irritation. Ingestion: May cause central nervous system depression, convulsions, coma, and possible death due to respiratory paralysis. Inhalation: May cause methemoglobinemia , cyanosis (bluish discoloration of skin), convulsions, tachycardia, dyspnea (labored breathing), and death. Severe overexposure can result in death. Inflammation of the

Aniline

-naphthol

NaNO2 crystals

NaOH

eye is characterized by redness, watering, and itching. Skin inflammation is characterized by itching, scaling, reddening, or, occasionally, blistering. Eye: May cause conjunctivitis. May cause permanent corneal opacification. Skin: Causes skin irritation. Ingestion: Harmful if swallowed. May cause cyanosis, convulsions, and death. Causes digestive tract irritation. Inhalation: May be fatal if inhaled. Inhalation: Causes damage of the upper respiratory tract. Symptoms may include sneezing, sore throat or runny nose. Ingestion: Swallowing may cause severe burns of mouth, throat, and stomach. Severe scarring of tissue and death may result. Skin Contact: Contact with skin can cause irritation or severe burns and scarring with greater exposures. Eye Contact: Causes irritation of

HCl

Ethanol

eyes, and with greater exposures it can cause burns that may result in permanent impairment of vision, even blindness. Inhalation: Inhalation of vapors can cause coughing, choking, inflammation of the nose, throat, and upper respiratory tract. Ingestion: Swallowi ng hydrochloric acid can cause immediate pain and burns of the mouth, throat, esophagus and gastrointestinal tract. Skin Contact: Can cause redness, pain, and severe skin burns. Eye Contact: Contact may cause severe burns and permanent eye damage. Eye: Produces irritation, characterized by a burning sensation, redness, tearing, inflammation, and possible corneal injury. Skin: May cause skin irritation. Prolonged and/or repeated contact may cause defatting of the skin and dermatitis Ingestion: May cause liver and

NaCl

kidney damage. May cause central nervous system depression, characterized by excitement, followed by headache, dizziness, drowsiness, and nausea. Inhalation: Inhalati on of high concentrations may cause central nervous system effects. Eye: May cause eye irritation. Skin: May cause skin irritation. Ingestion: Ingestion of large amounts may cause gastrointestinal irritation. Ingestion of large amounts may cause nausea and vomiting, rigidity or convulsions. Continued exposure can produce coma, dehydration, and internal organ congestion. Inhalation: May cause respiratory tract irritation.

IV. Waste Disposal Organic waste organic waste jar