saccharin (cyclic amide of o-sulpho-benzoic acid)-artificial sweetening agent- 1,1-dioxo-1,2-benzothiozol-3-one, synthesis,uses, discovery,physical properties , chemical properties, - study everything.

Saccharin

 

Discovery :

 

Saccharin is firstly discovered by russian chemist constantin fahlberg (22 dec. 1850 -15 aug. 1910 ) in 1789.

They have accidently  discovered saccharin .

When constantin fahlberg had worked a long time on the compounds products of coal-tar. One evening he was worked in laboratory till late ,then he was went for dinner without hand wash , he was surprised when they broke a piece of bread and put into mouth , it is undoubtedly sweet in taste .

They was surprised but not exactly understand why it is happening . they went for wash mouth and dried with napkin after wash , surprisingly the napkin is also become sweet, then they put fingers into mouth cause of fingers had touched before their work in laboratory , surprisingly fingers are sweet in taste ,

Then he was understand something but not clearly , immediately they dropped dinner and went in laboratory they check the taste of all  solutions they had worked on.

One of them solutions they found sweet taste ,after that they worked on that particular saccharin solution and make best way of synthesis for saccharin scientifically and commercially.

 After that their work for many months results into discovery of saccharin .

Generally the sucrose , glucose , fructose type natural saccharides are used for sweet test , but the saccharin is a artificial sweetening agent.

 

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.

 

Saccharin is a non-nutritive sweetening agent

It is a crystalline solid compound .

Saccharine  is  500 times sweeter than our regular sugar.

Practically it is insoluble in water but , sodium salt of saccharin is soluble in water .

Dilute solution of saccharine is sweet in taste but , highly concentrate (0.8%) solution of saccharin is bitter in taste.

Saccharine is synthesized from toluene and anthranilic acid .

 

Chemical properties :

 

IUPAC name :  1,1-dioxo-1,2-benzothiozol-3-one.

 

CAS number ; 81-07-2.

 

Structure formula :

 

Physical properties :

 

Molecular formula : C₇H₅NO₃S.

 

Molecular weight : 183.18 gm/mole.

 

Melting point : 228.8 ⁰C .

 

Boiling point : 226-229 ⁰C .

 

Solubility :  sodium salt of saccharin soluble in water ( 100 gm/liter at 20⁰C )

                        Slightly soluble in chloroform and benzene.

                       Also soluble in ethanol and acetone .

 

Color :  colorless or white .

 

State : crystalline solid.

 

Odor :  sweet aromatic odor or odorless.

Synthesis of saccharin

 

Two methods for synthesis of saccharine is given bellow,

 

Method-1 : synthesis of saccharin from toluene .

 

Statement :

 the condensation reaction of toluene with chloro sulphonic acid at 0-5 ⁰c  temperature gives two isomers  ortho and pera- toluene-sulphonyl-chloride. Then reaction of ortho isomer with ammonia forms o-toluene-sulphonamide , oxidation of o-toluene-sulphonamide in the presence of alkaline KMnO₄ gives o-amino-sulpho-benzoic acid. Heating of o-amino-sulpho-benzoic acid yields saccharin.

 

Chemical reaction :

 

Method-2 : synthesis of saccharin from anthranilic acid .

 

Statement :

Diazotization of anthranilic acid with NaNo₂ at 0-5 ⁰c , in the presence of H₂So₄ gives diazo-salt. Then  Diazo-salt reacted with liquid SO₂ , in the presence of copper catalyst forms 2-carboxy-benzene-sulphonic acid . after that reaction of 2-carboxy-benzene-sulphonic acid with Cl₂ and NaOH gives 2-carboxy-benzene-sulphonyl chloride, then reaction of 2-carboxy-benzene-sulphonyl chloride with ammonia yields saccharin.

 

Chemical reaction :

 

 uses of saccharin :

(1)    Saccharine is used by diabetic and fat person in the place of sugar , because of no nutrient value of saccharin.

 

Saccharin is also used in following given bellow ,

 

(2)    Jams

 

(3)    In Production of jellies.

 

 

(4)    Cookies .

 

(5)    Candies .

 

 

(6)    Medicines.

 

(7)    Toothpaste.

 

 

(8)    Cheap cold drinks.

 

(9)    Tinned fruit.

 

 

 

 

 

 

 

 

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