dulcin or sucrol or valzin(p-phen-ethyl-urea)-or(4-ethoxy phenyl)urea-synthesis,physical-chemical properties-by study everything

 

Dulcin (p-phen-ethyl-urea) or sucrol ,or valzin

Dulcin is a artificial sweetening agent.

Dulcin is 250 times sweeter then our regular sugars.

Dulcin is also known as sucrol and valzin.

It is synthesized from different methods , here we have three well known method for preparation of dulcin .

Discovery

It is discovered in 1883 , by a polish chemist joseph berlinerblau or jozef berlinerblau(1859-1935.)

Dulcin is discovered after five years of saccharine.

 

Sweetening agent :

 

Definition :  synthetic organic compound  which have a sweet test called sweetening agent .

Or

Artificial Non-saccharide compound which have a sweet test ,  known as sweetening agent.

Or

Some organic synthetic compounds are not saccharides but they have sweet test, these are called sweetening agents.

 

Natural sweetening agent   Some natural organic compounds have naturally sweet test,  contains calories and nutrients these are known as natural sweetening agent .   Eg. Glucose , sucrose , fructose , honey etc.

Artificial sweetening agent   Some artificial organic compound (but not saccharide) have a sweet test , not have any nutrient value , known as artificial sweetening agents.   Eg. Sachharin , aspartame, sucrolose , alitame ,   p-anisyl-urea , dulsin etc.

Dulcin is 250 times sweeter then our regular sugars.

Dulcin is also known as sucrol and valzin.

It is synthesized from different methods , here we have three well known method for preparation of dulcin .

 

Chemical properties

IUPAC name : (4-ethoxy phenyl) urea .

 

CAS number : 150-69-6

 

Structure formula :

 

Physical properties :

Molecular formula : C₉H₁₂O₂N₂ .

 

Molecular weight : 180.20 gm/mole.

 

Melting point : 173.5^oC . OR 446.6 k.

 

Boiling point : decomposes at normal temperature & pressure or (173^oC).

 

Solubility : water soluble (solubility in water is about 1.25 gm/liter at 25^oC).

                      It is also soluble in alcohol .

 

Color : white or colorless.

 

State : solid , white needles or white needle shape crystals  powder.

 

Odor : not specific odor or odorless.

 

Synthesis of dulcin or sucrol , or valzin.

Method-1 :

Synthesis of dulcin from p-ethoxy-nitrobenzene .

Statement :

The reduction of p-ethoxy-nitrobenzene in the presence of metal [Sn} and HCl , gives p-ethoxy-aniline then the reaction of p-ethoxy-aniline with urea(NH₂-CO-NH₂) Yields our final product dulcin.

Chemical reaction :

 

Method-2

Synthesis of dulcin from phenacetin .

Statement :

In the reaction the hydrolysis(HCl/H₂O) of phenacetin gives 1-(4-ethoxy-phenyl) amine carboxylic acid after that the reaction of 1-(4-ethoxy-phenyl) amine carboxylic acid with SOCl₂ and ammonia (NH₃) yields dulcin. 

Chemical reaction :

 

Method-3

Synthesis of dulcin from (4-amino phenol).

Statement :

the reaction of 4-amino-phenol with acetic anhydrate(ac₂o) and tri-ethyl-ammonia gives 4-ethoxy-amino-phenol then ; the reaction of 4-ethoxy-amino-phenol with (CH₃-CH₂-Br) in the presence of NaOH gives p-phen-ethyl-amino-methyl-ketone, after that the hydrolysis(H₂O/HCl) of p-phen-ethyl-amino-methyl-ketone gives p-phen-ethyl-ammonia , it’s react with urea(NH₂-CO-NH₂) in the presence of solid Na₂CO₃ , and acetic acid (CH₃-COOH) yields our final product dulcin.

 

Chemical reaction :    

Uses of dulcin :

dulcin is used as a sweeteners , in the place of sugars.

It used in human food .

 

 

 

Note : dulcin is contains some toxic effects on body .

Small  amount of dulcin(30-40 gm) causes hypotension , nausea, dizziness.

In a children it is more harmful sometimes it’s deadly poisonous for child.

Side effects of more amount of dulcin

(i)                  Headache

 

(ii)                Dizziness

 

(iii)               Nausea

 

(iv)              Skin irritation .

 

 

 

 

 

 

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