HEXAMINE PRODUCTION PLANT

COMPREHENSIVE PROJECT

Submitted by

VAGHELA VISHWADEEPSINH

17BCH054

Under the guidance of

Dr. Sweta Balchandani

Department of Chemical Engineering

School of Technology

Pandit Deendayal Energy University

Gandhinagar – 382007

Gujarat – INDIA
 STUDENT DECLARATION

I Vishwadeepsinh Vaghela hereby declare that this written submission represents my ideas

in my own words and where others’ idea or words have been included, I have adequately

cited and referenced the original sources. I also declare that I have adhered to all principles

of academic honestly and integrity and have not misrepresented or fabricated or falsified

any idea / data / fact / source in my submission. I understand that any violation of the above

will be cause for disciplinary action by the PANDIT DEENDAYAL PETROLEUM

UNIVERSITY and can also evoke penal action from the sources which have thus not been

properly cited or from whim proper permission has not been taken when needed.

VISHWADEEPSINH VAGHELA

17BCH054

DATE - 13 MARCH 2021

 APPROVAL SHEET

This report entitled (HEXAMINE PRODUCTION PLANT ) by (Vishwadeepsinh

Vaghela) is recommended for Mid comprehensive project review presentation.

Dr. Sweta Balchandani

Supervisor
 TABLE OF CONTENT Pg. No.

1. ITRODUCTION 5

2. PROPERTIES 6

3. HISTORY 7

4. PREPARATION 8

5. APPLICATIONS 10

6. REFERENCES 12
1.1 INTRODUCTION

Hexamethylenetetramine or methenamine is a heterocyclic organic compound with the formula

C6H12N4. This white crystalline compound is highly soluble in water and polar organic

solvents. It has a cage-like structure similar to adamantane. It is useful in the synthesis of other

chemical compounds, e.g., plastics, pharmaceuticals, rubber additives. It sublimes in vacuum at

280 °C.

Hexamethylenetetramine is prepared industrially by reacting formaldehyde and ammonia. The

reaction can be conducted in gas phase and in solution.

It acts as an anti-infective agent which is most commonly used to treat urinary tract infections.

Its anti-infective action is derived from the slow release of formaldehyde (CH 2O) by hydrolysis

at acidic pH of 0.2 molars. Methenamine is an odourless colourless lustrous crystal or white

crystalline powder which is hygroscopic.

Structure of Hexamine
1.2 PROPERTIES

Chemical formula C6H12N4

Molar Mass 140.186 g/mol

Appearance White crystalline solid

Odor Fishy, ammonia like

Density 1.33 g/cm3 (at 20 °C)

Melting point 280 °C (536 °F; 553 K)

Solubility in water 85.3 g/100 mL

Acidity 4.89

Flash Point 250 °C (482 °F; 523 K)

1.3 HISTORY
Invented in Murrhardt, Germany, in 1936, the main component is hexamine, which was

discovered by Aleksandr Butlerov in 1859.

Hexamethylenetetramine was first introduced into the medical setting in 1899 as a urinary

antiseptic. However, it was only used in cases of acidic urine, whereas boric acid was used to

treat urinary tract infections with alkaline urine. Scientist De Eds found that there was a direct

correlation between the acidity of hexamethylenetetramine's environment and the rate of its

decomposition. Therefore, its effectiveness as a drug depended greatly on the acidity of the urine

rather than the amount of the drug administered. In an alkaline environment,

hexamethylenetetramine was found to be almost completely inactive.

Hexamethylenetetramine was also used as a method of treatment for soldiers exposed to

phosgene\ in World War I. Subsequent studies have shown that large doses of

hexamethylenetetramine provide some protection if taken before phosgene exposure but none if

taken afterwards.

1.4 PREPARATION OF HEXAMINE

Combinations of ammonia and formaldehyde create very pure hexamine, and the solution can

be boiled to expel excess ammonia or formaldehyde and to crystallize out the soluble

hexamine. Hexamine can be further purified by sublimating it at high heat and depositing it on

a cool surface. This can be accomplished with a bucket, a lid, and a heating source.

473 g of a 38 % formaldehyde solution, is treated with 700 g of 20% ammonia hydroxide

solution, until the solution is slightly alkaline. The mixture is allowed to stand, for several

hours and if necessary more ammonia being added. The solution is filtered and then

evaporated in vacuum to a thick paste. The hexamine crystals are filtered off washed with

ethyl alcohol, and dried. To obtain pure hexamine it is recrystallized from water or alcohol.

Hexamine forms colorless, odorless crystals, which are soluble in water, and 90 % alcohol. It

does not melt on heating, but sublimes at a temperature of about 260° C.

EXPERIMENTAL (REAGENTS )
Redistilled glacial acetic acid (m.p. 16.60°C.) was used as solvent. Formaldehyde solutions

were prepared by depolyrnerization of paraformaldehyde in hot (70°C.) glacial acetic acid,

and standardized volumetrically by determining the extent of reduction in a Nessler solution

(2). Ammonium nitrate, ammonium acetate, and sodium acetate solutions in glacial acetic acid

were prepared by weight, using anhydrous reagent grade salts. Nitric acid of 99.6% purity was

prepared by distilling the commercial product (68%) with twice its volume; of concentrated

sulphuric acid, after which the oxides of nitrogen were removed from the distillate with a

stream of dry nitrogen. The acid was stored at - 68°C. Analytical Methods The hexamine

content of a partially reacted formaldehyde -ammonium salt solution in glacial acetic acid was

determined by adding a cool slurry of mercuric chloride in aqueous sodium hydroxide. The

sodium hydroxide content was adjusted so that the pH of the mixture was brought to 4.0

during precipitation of the hexamine -mercuric chloride complex from an appropriate aliquot

of the reaction mixture. Under these conditions, estimation of hexamine from the dry weight

of the precipitate was found to be quantitative within 0.2% of the theoretical, for solutions

containing in excess of 50 mgm. per litre of hexamine. The composition of the complex was

constant, with a gravimetric factor of 0.0768.

1.5 APPLICATIONS
 One of the major uses of Hexamine is in the manufacture of dinitrosopentamethylene-

tetramine, a blowing agent for rubber.

 It is used as a catalyst in the manufacture of Bakelite phenol formaldehyde molding

powders.

 It is used as a basic raw material in slurry explosives.

 It has many other applications in the manufacture of plastics, paints, foundry resins,

textiles, plywood, laminated sheets, cement, fertilizers, pesticides, solid fuel tablets etc.

 Unstabilized Hexamine is used in adhesives, coatings and sealing compounds, in the

preservation of hides, as cross-linking agent for hardening phenol-formaldehyde resins

and vulcanizing rubber, as corrosion inhibitor for steel, as dye fixative, as fuel tablets for

camping stoves, as stabilizer for lubricating and insulating oils, for manufacture of

explosives, chemical detection of metals and as an urinary antiseptic.

 Stabilized Hexamine is used in process industry, as per the requirements of specific

customers.

Industry Uses

Hexamethylenetetramine is dominantly used in the production of powdery or liquid preparations

of phenolic resins and phenolic resin molding compounds where it is added as a hardening

component. These products are used as binders in the manufacture of brake and clutch linings,

abrasive products, non-woven textiles, formed parts produced by molding processes, and
fireproof materials. It is also used in the medical profession for the treatment of urinary tract

infections.

Because it is smokeless when burned, has a high energy density of 30.0 megajoules per kilogram

(MJ/kg), does not liquify while burning, and leaves no ashes, hexamethylenetetramine is a

component of hexamine fuel tablets used by campers, hobbyists, the military and relief

organizations for heating camping food as well as military rations.

The crystalline compound is also used as a reagent in organic chemistry, a food additive as a

preservative, and as the base component in the manufacture of certain explosives.

Consumer Uses

1. Adhesives and Sealants

2. Agricultural Products (non-pesticidal)

3. Automotive Care Products

4. Building/Construction Materials not covered elsewhere

5. CBI

6. Plastic and Rubber Products not covered elsewhere

References

1. Cooney, A. P.; Crampton, M. R.; Golding, P. (1986). "The acid-base behaviour of

hexamine and its N-acetyl derivatives

2. Eller, K.; Henkes, E.; Rossbacher, R.; Höke, H. (2000). "Amines, Aliphatic".

Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH Verlag GmbH

3. Blažzević, N.; Kolbah, D.; Belin, B.; Šunjić, V.; Kajfež, F. (1979).

"Hexamethylenetetramine, A Versatile Reagent in Organic Synthesis