Study of some official compounds

Topic no. 16. Study of some official compounds

1. Chlorbutol

IUPAC name- 1,1,1-trichloro-2-methylpropran-2- ol

Molecular formula- C4H6Cl3OH

Molecular weight- 175.5 g/mol

Structure-

Other names – Chloretone

Physical properties-

It is white crystalline powder found in two forms: anhydrous and hydrated, also it has characteristic
camphor-like odor and taste. The melting point is 95-99 ºC and boiling point is 167 ºC. It is freely soluble
in alcohol (1:1) slightly soluble in cold water (1:125) and more soluble in boiling water but such high
temperature may lead to hydrolysis of chlorobutanol.

So it must be recrystallized from water/alcohol mixture. Water is not good solvent for recrystallization
and often hydroalcoholic mixtures are used for this purpose.

Preparation- It is prepared by direct combination of acetone with chloroform in presence of solid KOH.

Chlorbutanol is formed by the simple nucleophilic addition of chloroform and acetone, this reaction is
base driven by potassium or sodium hydroxide. Alcoholic KOH is used in order to accelerate the reaction
towards formation of chlorobutanol

Procedure of synthesis-

1. In a dry conical flask put 5 mL of acetone with 2 mL of chloroform.

2. Cool the mixture.

3. Alcoholic solution is prepared from dissolving 0.35 g of KOH in the minimum amount of ethanol
(rectified spirit about 5mL).

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4. Add alcoholic solution in step 3 to the mixture of step 2.

5. Filter the precipitated KCl and wash it twice with small portions of acetone.

6. Evaporate in water bath.

7. Recrysallised from the mixture of water and ethanol.

Assay - A weighed quantity of substance is dissolved in alcohol and hydrolysed by being boiled under
reflux with aq NaOH. The chlorides ions are determined by Volhard’s method with N/10 AgNO 3 an N/10
NH4SCN. Before the thiocynate titration the mixture is shaken in presence of small quantity of nitro
benzene in order to coagulate the AgCl precipitate.The result is expressed in terms of the hemi hydrate, so
that 1000 ml of N/10 AgNO 3 are equivalent to 1/30 Of C4 H7Cl3O. 1/2 H2 O.

Use- It can be used for many therapeutic indications.

1. Bacteriostatic use as preservatives in many injectable, ophthalmic and intranasal preparations.

2. Sedative, hypnotic and in motion sickness.

3. Local anesthetic in many painful IM injections and dental preparations.

2. Dimercaprol

Molecular formula- C3H8OS 2.

Molecular weight- 124.227 g/mol

Other names- British Anti-Lewisite, BAL, 2,3 dimercapto‐1‐propanol

Properties- It is an oily, pungent smelling, viscous liquid.

Preparation- Dimercaprol is prepared by the bromination of allyl alcohol to glycerol di-bromine-hydrine

followed by reaction with sodium hydrosulfide under pressure.

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Assay- Dissolve about 0.12 gm, accurately weighed in 20 ml of HCl (0.1 mol/l) and titrate rapily with
iodine using starch is an indicator. Report the experiment test without the test liquid being examined, and
make any necessary corrections. Each 1ml of iodine Vs is equivalent to 6.211mg of C3H8OS2.

Use-

1. Antidote for arsenic, gold and mercurypoisoning.

2. As a chelating agent.

3. Glyceryl Trinitrate

Molecular formula- C3H5O3(NO2)

Molecular weight- C3H5N3O9

Other names- nitroglycerine

Preparation- It is prepared by slowly adding glycerol to an ice cooled mixture of

conc.H2SO4 and conc.HNO3. The solution is cautiously run into ice cold water, the
nitroglycerine then separates as a heavy oil which is purified by repeated washing with cold
water.

Assay- Nitrate is determined calorimetrically in a weighed quantity of the powdered

tablets by interaction with phenol‐2,4‐disulphonic acid and subsequent classification with
ammonia. The yellow color is matched against that of solution containing known
quantities of potassium nitrate which have been treated similarly. The assay depends on
the formation of colored nitro compounds by the interaction of the glycerol trinitrate with
the phenol‐2,4‐ disulphonic acid, and the sub sequent conversion of these into intensely
ammonium salts.

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The method suffers from certain disadvantages, the most important of which is the
difficulty of correctly matching the yellow color.

Use-

1. It is used to treat angina (chest pain). It can help stop chest pain if an angina attack
has already started. It can also help to prevent them from starting.

2. GTN ointment can also be used to treat tears in the skin around your bottom (anal
fissures).

3. It comes as tablets or as a spray that you put under your tongue. It also comes as
patches and ointment that you put on your skin.

4. Sometimes GTN patches are used in hospital to make your veins easier to see if you
need to have a drip (infusion).

5. Manufacture of dynamite and blasting gelatin which are comparatively safe explosives.

6. In tablets it is given in certain diseases of heart

4. Urea

Molecular formula- NH2CONH2.

Molecular weight- 60.06 g/mol

Properties- It is a colorless, crystalline substance that melts at 132.7° C (271° F) and decomposes before
boiling.

Urea is the chief nitrogenous end product of the metabolic breakdown of proteins in all mammals and
some fishes. The material occurs not only in the urine of all mammals but also in their blood, bile, milk,
and perspiration.

Preparation-

1. A laboratory method is to evaporate solution of ammonium cynate to dryness (wohler) about 95%
NH4CN becomes converted into urea by reversible isomeric change.
2. It is also synthesized by interaction of ammonia with carbonylchloride.
3. It is also synthesized by following reaction.

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Assay- The official process is based on the method of Richmond and hill. This hydrolysis the saccharin to
the sodium salt of O‐sulphonyl benzoic acid, without loss of ammonia.

Uses-

1. Urea is used to treat dry/rough skin conditions (e.g., eczema, psoriasis, corns, callus) and
some nail problems (e.g., ingrown nails). It may also be used to help remove dead tissue in some
wounds to help wound healing. Urea is known as a keratolytic.
2. In Agriculture, resins, automobile systems and in Laboratory

3. An ingredient in some skin cream, moisturizers, hair conditioners, and shampoos

5.Ethylene Diamine dihydrate

Molecular Formula- C2H4(NH2)2.2H2O

Preparation- Ethylenediamine is produced industrially by treating 1,2-

dichloroethane with ammonia under pressure at 180 °C in an aqueous medium:[6][7]

In this reaction hydrogen chloride is generated, which forms a salt with the amine. The amine is
liberated by addition of sodium hydroxide and can then be recovered
by rectification [de]. Diethylenetriamine (DETA) and triethylenetetramine (TETA) are formed as by-
products.
Another industrial route to ethylenediamine involves the reaction of ethanolamine and ammonia:

This process involves passing the gaseous reactants over a bed of nickel heterogeneous catalysts.

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It can be produced in the lab by the reaction of ethylene glycol and urea.
Ethylenediamine can be purified by treatment with sodium hydroxide to remove water followed by
distillation.
Assay- By titration with N/1 HCl to the bromophenol blue indicator, this indicates the formation of
the dihydrochloric acid.

Uses-

1. Ethylenediamine is an organic compound that is used as a building block for the production of
many other chemical products.

2. It is also used as an excipient in many pharmacological preparations such as creams. Notably,

ethylenediamine is a contact sensitizer capable of producing local and generalized reactions.

3. as a solvent, it is miscible with polar solvents and is used to solubilize proteins such
as albumins and casein. It is also used in certain electroplating baths.

4. as a corrosion inhibitor in paints and coolants.

5. ethylenediamine dihydroiodide (EDDI) is added to animal feeds as a source of iodide.

6. chemicals for color photography developing, binders, adhesives, fabric softeners, curing agents
for epoxies, and dyes.

7. as a compound to sensitize nitromethane into an explosive. This mixture was used at Picatinny
Arsenal during World War II, giving the nitromethane and ethylenediamine mixture the
nickname PLX, or Picatinny Liquid Explosive.

6.Vanillin

Molecular formula- C8H8O3

Preparation- It is the flavouring agent of the vanilla pods can be made synthetically from guaicol by
remier – tiemann reaction. It is also prepared by eugenol. This compound is first isomerised bythe
alkali to isoeugenol and the later is then subjected to controlled oxidation.

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Assay- Weigh accurately about 0.12gm dissolve 20ml of ethanol add 60ml of CO2 free H2O and
titrate with 0.1mNaOH determining the end point ,potentiometrically each 1ml of 0.1m NaOH is
equivalent to 0.01521g of C8H8O3..

Uses-

1. As a flavouring agent particularly in chocolate ice cream and confectionary.

2. It is used in flavorings, foods, perfumes, and pharmaceuticals.

3. Vanillin is used as a chemical intermediate in the manufacture of several important drugs and
other products.

4. Human exposure to vanillin is through dermal contact with perfumes and ingestion of food
products that include vanillin as a flavor additive.
7. Paraldehyde

Molecular formula- (C2H4O)3

IUPAC Name- 2,4,6-Trimethyl-1,3,5-trioxane

Preparation- When acetaldehyde is treated with a smallamount of con. H2SO4 of room temperature a
cyclic trimer paraldehyde is formed.

Uses-

1. sedative and hypnotic

2. obstetric analgesic
3. Paraldehyde is used in resin manufacture, as a preservative, MEP and in other processes as
a solvent.
4. It has been used in the generation of aldehyde fuchsin.
8.Ethylene chloride

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Molecular formula- C2H4Cl2

Preparation- Ethylene chloride is produced by thereaction of ethylene and chlorine.

Assay- Stock, standard gas was created by static dilution form 100% analyte, mixed volumetrically
with input ofO2, sample is verified by chromatography.

Uses- Used as degreasing agent and paint remover.

9.Lactic acid

Molecular formula- CH3.CH(OH).CO2H

Preparation- Lactic acid has been prepared by brominating propionic acid and hydrolysing the resultant
2‐bromopropionicacid to sodium lactate by heating with dil.alkali.
Assay- A weighted quantity is diluted with H2O and boiled with N/1 sodium hydroxide and excess of
alkali is then determined by titration with N/1 HCl by using phenolphthalein as indicator. The boiling
alkali hydrolyses the condensation products.
Uses-

1. Used in dairy products

2. For determining of tides

3. Ethyl and butyl lactates are used as plasticers.
10. Tartaric acid

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Molecular formula- CO2H.CH(OH).CH(OH).CO2H

Preparation- From malic acid‐ malic acid produced industrially by oxidation of cyclohexone is treated
with alkalineKMNO4 to get m‐tartaric acid.
Assay- : Titration with N/1 NaOH using phenolphthaleinas indicator.

2NaOH+C4H6O6 → Na2C4H4O6+2H2O

1,000ml of N/1 alkali are equivalent to ½ C4H6O6

Uses-

1. In carbonated beverages and effervescent tablets

2. In baking powder
3. In silvering of mixtures
11. Citric acid

Molecular formula- C6H8O7.H20

Preparation- From molasses‐ it containing sucrose is diluted to water and subjected to fermenting
with a micro organism Aspergillus niger.

Assay- The fermentation process is carried out for 7‐10days at 26‐280C.The resulting solution of
citric acid is neutralized with Ca(OH)2 to form insoluble calcium citrate.This is washed with H2O and
decomposed with dilute H2SO4.The calcium sulphate is filtered of and the solution concentration
under vaccum to get crystals of citric acid.
Uses-

1. Used as a mordant
2. As a esters that are good plasticizers for lacquers and vanishers.

12. Salicylic acid

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Molecular formula- C6H4(OH).CO2H

Preparation- This involves the treatment of sodium phenoxide with CO2 at 1250C under 6atm of
pressure followedby acid hydrolyses therefore acid is formed.

Assay- Titration with N/2 NaOH in alcoholic solution using phenol as red indicator. The end point
marks the completion of sodium salt. The presence of hydroxyl group makes the acid stonger than
benzoic. The constant is 1×10‐3 andthe pH of sodium salicylate is therefore close to 7.

NaOH+C6H6(OH).CO2H→C6H4.CO2Na+H2O

1,000ml of N/2 alkali are equivalent to ½ C6H4(OH)CO2H

USE- Used as antiseptic and disinfectant.

13. Aspirin

Molecular formula- C6H4(O.CO.CH3)CO2H

Preparation- It is prepared by heating salicylic acid with acetyl chlorine in the presence of
phosphoric acid. Notice thatonly OH group isinvolved in the reaction.

Assay- Hydrolysis with a measured volume of N/2 NaOH and titration of excess of alkali with N/2
acid. The final neutralized solution contains sodium acetate and monosodiumsalicylate.

1,000ml of N/2 alkali are equivalent to ¼ C6H4(OCOCH3)CO2H

Uses-

1. Used as a painkiller

2. It is sold under the trade name aspirin.

14. Methyl salicylate

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Molecular formula- C8H9O3

Preparation- It is prepared by esterfying salicylic acid withmethanol in presence of H2SO4.

Assay- By a modification of the method for the determination of the esters. Instead of being first
neutralized to phenolphthalein, on alcoholic solution is saponified by directly with alc.KOH. No
correction is made for any free acid present, but permiscible amount of this is controlled by the above
mention test. To ensure complete hydrolysis longer boiling is necessary than in the official process for
the determination of the esters.

Uses- It is used in hair tonics and ointments for treatingaches, sproins and bruises.

15. Ethyl benzoate

Molecular formula- C9H10O3

Preparation- Ethyl alcohol is treated with benzyl chloride.

C2H5OH+C6H5CO2H →C6H5COOC2H5+H2O

Assay- : Place about 0.08g accurately weighted in a round glass stopped flask, add 2.5ml of
NaOH and boil gently under reflex condenser for 3mins.

USE- Used as artificial fruit flavouring agent.

16. Benzyl Benzoate

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Molecular formula- C14H12O2

Preparation-

1. Prepared by esterification of benzyl alcohol with benzoicacid of catalyst.

2. By heating benzyl chloride with potassium benzoate in thepresence of diethyl amine.

3. Condensation of sodium benzyl oxide in non aqueoussolution.
Assay- Add about 2.0g accurately weighted 240ml of KOH/C2H5OH Vs and boil under reflex for
1hr. Cool and titratewith HCl Vs using phenolphthalein or ethanol as indicator.
Repeat the operation without the test liquid being examined and make any necessary correction.
Each 1ml of KOH/C2H5OHVs equivalent to 106.1mg of C14H12O2.
Use- Used as a antiparasitic(scabicide‐topical use).
17. Dimethyl phthalate

Molecular formula- C10H10O4

Preparation- It is prepared by oxidation of p‐xylene andsubsequent, esterification with methyl

alcohol.

CH3C6H4CH3 + (O) → HOOC.C6H4COOH

HOOC. C6H4COOH + 2CH3OH → CH3COO.C6H4COOH

Assay- Weigh accurately about 2g of dimethyl phthalate into a 250ml flask attached to reflex
condenser and add 50cc of 0.5NaOH and add 10cc of H2O and reflex for 1 hr. wash down the
sides of the container and glass connection with about 2.5cc of water, cool and add 0.2cc of

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thymol blue and titrate excess alkalie with 0.5N HCl to the production of yellow colour
performance.

Uses-

1. Used as ectoparasiticide

2. Solid rocket propallents

18. Sodium lauryl sulphate

Molecular Formula- NaC12H25SO4

Preparation- It is prepared by sulphating long chain fatty alcohols and neutralizing with
alkali to form the sodium salts. The alcohols are prepared by reduction of coconut oil by high
pressure hydrogenation using the catalyst copper‐chromium oxide.

Assay- Weigh accurately about 1.15g, dissolve in sufficient water to produce 1,000ml warming if
necessary to 20.01ml add 15ml of CHCl3 10ml of dil.H2SO4 and dimethyl oracet blue solution and titrate
with 0.004M benzethonium chloride, until the CHCl 3 layer acquires a permanent clear green colour. Each
1ml of 0.004M benzethonium chloride is equivalent to 0.00115g of sodium alkali sulphates, calculated as
C12H25NaO4S.

Uses- : Pharmaceutical aid, acts as surfactant, as an emulsifier.

19. Sodium sacharrin

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Molecular formula- C7H4NNaO3S

Preparation- When saccharin is treated with aqueous NaOH to form saccharin sodium.

Assay- Weigh accurately about 0.15g, dissolve in 50ml of anhydrous glacial acetic acid. With slight
heating if necessary and carry out method A for non aqueous titration, determining the end
potentiometrically perform a blank determination and make any necessary correction.

Each ml of 0.1M perchloric acid is equivalent to 0.02052g ofC 7H4NNaO3S.

Uses- Pharmaceutical aid, preparation of toothpaste.

20. Mephensin

Molecular formula- (C11H17N)2H2SO4

Preparation- It is synthesized from o‐cresol. It is treated with aq.NaOH to convert sodium salt which
undergoes nucleophillic substitute with 3‐chloro‐1,2 propanediol to give mephensin.

Assay- Test for mephensin, injection equivalent is measured accurately 1g of mephensin in position.

Uses- Used as analgesic, axiolytic, anti‐fungalsometimes, muscular relaxant.

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