Examining The Separation Of Naphthalene And Biphenyl Biology

Table of Content

Napthalene and biphenyl mixture is a binary mixture of substances where the substances are really similar to each other as can be observed from their constructions. Due to their similarities in physical belongingss their separation can non be accomplished by simple crystallization solvent extraction. Therefore, in such instance, there must be a chemically alteration of one of the constituents to render it significally different from the other components. Then separation of the derivative from the mixture ; and eventually the derived function is transformed back from the mixture.

It is noted that although the napthalene and biphenyl are two highly similar chemicals, the naphthalene is a Lewis base that reacts with picric acid to organize a picrate. However, biphenyl does non. It is besides noted that the separation is made possible because solid naphthalene picrate has different solubility belongingss from naphthalene and biphenyl.

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spatula, glass rod, electronic balance, ice-cold H2O, distilled H2O, Bunsen fire, capillary tubings, runing point setup, thermometre, Hirsch funnel and appropriately sized filter documents, Buchner flask, filter funnel, stemless funnel, little beaker, pipette, boiling tubings, 100 milliliter and 250 mL conelike flasks, fluted filter documents, ticker glass.

2.3 Procedure

Separate a ) Forming the naphthalene derivative ( naphthalene picrate ) and insulating it from biphenyl

A beaker was prepared, half-filled with H2O, and placed on a steam bath in the fume closet. This was done in order to fix a H2O bath.

A clean boiling tubing was placed in a little beaker, which were put on an electronic balance and the TARE was used to extinguish the weight of the glass ware.

1.001 g of naphthalene ( 50 % w/w ) and biphenyl mixture were weighed utilizing an electronic balance. These were placed the boiling tubing straight utilizing a spatula.

2 milliliter of methyl alcohol were added to the mixture in the boiling tubing. The tubing was so placed in the H2O bath and heated on the steam bath until the mixture was wholly dissolved. Once it dissolved the white coloring material of the solid mixture disappeared as it dissolved and the solution obtained was colourless.

In another boiling tubing 1.3 g of picric acid were weighed and 10 milliliters methyl alcohols were added to the boiling tubing. The volume was measured utilizing a measurement cylinder. The picric acid was xanthous in coloring material with the solid pulverization at the underside of the container.

Then the boiling tubing was warmed in the H2O bath until a xanthous solution was obtained.

A few beads of the picric acerb solution were put aside utilizing a pipette. The pipette was placed in a boiling tubing on the rack and left there to be used subsequently.

The picric acerb solution was added easy to the mixture of naphthalene and biphenyl solution. Then the boiling tubing was warmed for 1 minute on the steam bath. Once the xanthous solution became deeper and stronger and crytals were merely approximately to get down organizing the boiling tubing was removed and allowed to chill on the bench. Then after chilling it was placed in ice-cold H2O. This resulted in the formation of solid naphthalene picrate.

Vacuum filtration was carried out utilizing a Hirsch funnel, fitted with a filter paper of a suited size, and corked to a Buchner flask. The gum elastic tube was attached to the arm of the flask and the vacuity beginning was turned on.

The crystals formed were so collected in the Hirsch funnel. They were washed with methyl alcohol, of which the lower limit of volume was used.

The crystals collected were transferred onto a ticker glass utilizing a spatula, and left to dry on the bench. The mass of the naphthalene picrate crystals was so found by weighing it. This means that the mass found included the weight of the ticker glass excessively. Hence the mass of the ticker glass entirely was so taken after the experiment and a minus was done in order to obtain the mass of the crystals entirely.

Then the runing point was determined. This was done by puting the center of a capillary tubing into a Bunsen fire. This melted into two halves due to heat. A runing point tubing was so filled up to 2-4 millimeter by tapping gently the unfastened terminal into the naphthalene picrate on the ticker glass. Then the tubing was inverted and tapping was done once more so as to let the sample to travel downwards the closed terminal of the tubing. Once this was done the tubing was placed in the thaw point setup which was switched on some clip beforehand. The runing point temperature scope was so recorded, by entering the temperature at which the merchandise foremost started to run and the temperature at which the merchandise melted wholly.

The presence of naphthalene in the picrate was checked by the add-on of a few beads of fresh picric acerb solution ; ( the few beads that were kept aside antecedently, with a pipette ) It was noted that no picrate was formed. This means that the separation was complete.

Part B ) Re-extracting biphenyl, sublimating it and proving its pureness

1 milliliter concentrated ammonium hydroxide and 30 milliliters H2O were measured utilizing a meauring cylinder. These were placed in the filtrate. This resulted in the precipitation of the biphenyl.

The biphenyl was collected by filtration utilizing a filter funnel fitted with a fluted filter paper and a conelike flask beneath. The filtrate was added easy into the filter paper until filtration was complete.

The residue left on the filter paper was collected and transferred onto a ticker glass utilizing a spatula and left to dry a spot. Then it was dissolved in a minimal sum of hot H2O in a conelike flask.

Hot gravitation filtration was carried out utilizing a stemless funnel with a fluted filter paper, and a 100 milliliter conelike flask. Then the filtrate was allowed to chill.

After chilling it was placed in ice-cold H2O, and after some clip the sides of the conelike flask were scratched with a glass rod, to let the formation of the crystals. However, no crystals were observed. Therefore the solution was discarded and so the mass and the runing point of the recrystallised biphenyl were non found. Hence no consequences were obtained.

Part degree Celsius ) Re-converting the picrate to naphthalene, sublimating it and proving its pureness

The picrate crystals were placed in a 100 milliliter conelike flask, and were dissolved in a small hot methyl alcohol by warming on the steam bath.

Then 1 milliliters concentrated ammonium hydroxide and 30 milliliters H2O were added to the conelike flask. After warming for 1 minute the solution was allowed to chill to room temperature, and so placed in ice-cold H2O.

The naphthalene was filtered by hot gravitation filtration and recrystallised from methyl alcohol by vacuity filtration.


Hot Gravity Filtration Vacuum Filtration


It was ensured that all the setup was rinsed with distilled H2O so as to forestall taint.

It was ensured that it was the picric acid solution that was added to the mixture solution of naphthalene and biphenyl, and non vice-versa, and the add-on was does easy and gently so as to forestall spilling of some of the solution, and besides so as to let clip for the reaction to happen easy, for the formation of the solid naphthalene picrate.

It was ensured that the needed clip was allowed for complete filtration to happen. This filtration was completed until no more beads of filtrate appeared to fall.

It was ensured that the Buchner flask was pressed downwards with the custodies during the vacuity filtration procedure. This was done so as to guarantee that full suction was present and so vacuity was created, so that filtration was done wholly.

It was ensured that the gum elastic tube was disconnected foremost and so the H2O aspirator turned off, so as to forestall sucking back and so taint of the substance.

It was ensured that both the stemless funnel and the conelike flask were warmed merely a small before hot gravitation filtration was carried out, by puting them in an oven for a short clip. This was of import so as to forestall premature crystallization.

It was ensured that attention was taken when the capillary tubing was placed into the Bunsen fire in order to run it into half. This was of import so as to forestall and avoid hurts of the custodies or fingers even though baseball mitts were worn.

It was ensured that parallax mistakes were avoided every bit much as possible by looking usually to the graduated table of the thermometre when taking the reading of the runing point temperature scope. Besides, when mensurating volume of solutions utilizing a measurement cylinder.

3. Consequences and Calculations

3.1 Consequences

mass of napthalene ( 50 % w/w ) and biphenyl mixture used: 1.001 g

mass of naphthalene picrate crystals: 1.958 g

runing point temperature scope of solid naphthalene picrate: 129 – 136 ISC

mass of detached biphenyl: /

runing point temperature scope of biphenyl: /

mass of detached naphthalene: 0.347 g

runing point temperature scope of naphthalene: 81 – 92 ISC

3.2 Calculations

mass of napthalene picrate crystals watch glass: 30.391 g –

mass of ticker glass merely: 28.433 g

hence, mass of naphthalene picrate crystals: 1.958 g

Percentage Recovery for purified detached naphthalene:

% output = existent mass X 100 %

theoretical mass

= 0.3470 g X 100 %

0.5005 g

% output = 69.33 %

4. Discussion

When several benzine rings are fused together to give more drawn-out pi systems, the molecules are called polycyclic benzenoid or polycyclic aromatic hydrocarbons ( PAHa ) . In these constructions two or more benzene rings portion two or more C atoms.

The merger of one benzine ring to another consequences in a compound called naphthalene. Further merger can happen in a additive mode to give anthracene, tetracene, pentcacene, a series called the acenes. Angular merger ( annulation ) consequences in phenanthrene, which can be farther annulated to a assortment of benzenoid polycycles.

In contrast to benzene, which is a liquid, naphthalene is a colorless crystaline stuff. It is best known as a moth repellant and insect powder. The spectral belongingss of naphthalene strongly suggest that is portions benzine ‘s delocalised electronic construction and thermodynamic stableness. Basically when detecting spectra and extremums, it is concluded that the negatrons in napthalene are delocalised more extensively than in benzine. Therefore the added four pi negatrons enter into efficient convergence with those of the affiliated benzine ring. Hence, several resonance signifiers can be drawn:

Resonance Forms of Naphthalene

Naphthalene is an illustration of a polycyclic aromatic molecule where resonance signifiers are used to depict the responsiveness of these molecules. Resonance is a manner of depicting delocalized negatrons within certain molecules or polyatomic ions where the bonding can non be expressed by one individual Lewis expression. Is is noted that a molecule or ion with such delocalized negatrons is represented by several lending constructions, called resonance constructions or canonical signifiers.

Basically the aromatic character of naphthalene is proven in this responsiveness. Naphthalene undergoes electrophilic permutation instead than add-on. For illustration, intervention with Br, even in the absence of a accelerator, consequences in smooth transition into 1-bromonaphthalene. The mild conditions required for this procedure turn out that naphthalene is activated with regard to electrophilic aromatic permutation. It is noted that these reaction can happen in the absence of a accelerator. However if benzene alternatively of naphthalene, an aluminum chloride accelerator is required for the reaction to happen. Similarly, whereas both benzine and naphthalene can be alkylated utilizing Friedel-Crafts reactions, naphthalene can besides be alkylated by reaction with olefines or intoxicants, with phosphorous acid as the accelerator.

Sing electrophiles, it is noted that these onslaught substituted naphthalenes regioselectively. This fundamentally refers to the penchant of one way of chemical bond devising or breakage over all other possible waies. It is noted that an triping group normally directs the incoming electrophile to the same ring anda deactivating group directs it off. This pealing transporting the substituent is the most affected.

It is of import to besides advert the picric acerb apart from the naphthalene. This is because this acid was utile for the formation of the derivative, solid naphthalene picrate. Picric acid is really the chemical compound called 2,4,6-trinitrophenol ( TNP ) . This xanthous crystalline solid is one of the most acidic phenols. It is an explosive, like other extremely nitrated compounds such as TNT. Picric acid is called acid because of the remarkably high sourness of its hydroxyl group ( pKa 0.38 ) which is increased beyond that of acetic acid ( pKa 4.7 ) and even hydrogen fluoride ( pKa 3.2 ) by the electron-withdrawing consequence of the three nitro groups. It is noted that this belongings was in portion responsible for its replacing by TNT in military utilizations.

Traveling on to the derived function formed, one should first state that a picrate is really a salt or an ester of picric acid. However, it is of import to state that it could besides be an extra compound which picric acid signifiers with many aromatic hydrocarbons, as in this instance in this experiment, where the aromatic hydrocarbon is naphthalene. Hence, extra compounds are besides called picrates, even though they are non a salt of picric acid.

Naphthalene picrate

Discoursing the consequences obtained in this experiment it is noted that no information of the consequences obtained could be recorded for the biphenyl. This is because the biphenyl did non clear. For recrystallisation the solubility of the substance is required to be high in the hot dissolver but low when it is cooled, so that the coveted merchandise will clear whilst drosss remain dissolved. However, this did non go on for the biphenyl. After chilling in ice-cold H2O for several proceedingss, it did non clear. A ground for this could be due to the solubility of the biphenyl, which is found to be really soluble at room temperature and so most of the biphenyl remained dissolved. Hence hapless recovery is obtained such that the biphenyl was discarded. Hence no vacuity filtration was carried out since no crystals were formed.

One should state that in order to increase the output, a 2nd mixable dissolver could be added. This would change the solvent mutual opposition sufficiently to diminish the solubility of biphenyl. As the 2nd dissolver diffuses into the mixture, the biphenyl should clear out.

Beginnings of mistake:

The naphthalene crystals to be collected on the Hirsch funnel merely passed through the filter paper into the Buchner flask during vacuity filtration. This might occurred due to the crystals non being formed wholly or due to the crystals which might fade out a spot in the methnaol ( solvent ) during the procedure and so passed through, even though a minimal sum of dissolver was used. The procedure was so repeated so as to roll up as much merchandise as possible, and the output claculated was rather sensible.

The solid naphthalene picrate crystals formed and collected on a ticker glass were non wholly dry when they were weighed and the thaw point temperature scope was determined. This was due to miss of clip available. Hence the mass obtained might change a spot and was somewhat greater due to some dissolver still present. This was noted during the runing point finding procedure where the powdery sample was really hard to be tapped down to the underside of the thaw tubing. It merely kept being blocked in the center within the tubing, because it was non wholly dry.

5. Decision

It was concluded that the naphthalene ( 50 % w/w ) and biphenyl mixture was separated and the separation involved the formation of a derived function of naphthalene, a solid napthalene picrate, which was isolated from biphenyl. It was besides concluded that at the terminal of the twenty-four hours, it was the single constituents which were required to be obtained separately, i.e. the purified biphenyl and the purified naphthalene which was reconverted from picrate. Hence since this was achieved the experiment was rather successful since the aimwas reached.


McMaster University 1997/98: hypertext transfer protocol: //www.chemistry.mcmaster.ca/~chem2o6/labmanual/expt1/exp1b-i.html, retrieved 2010, 1st December.

Founder -Jimmy Wales: Wikipedia the free encyclopaedia 2010:

hypertext transfer protocol: //en.wikipedia.org/wiki/Naphthalene, retrieved 1st December 2010.

The organic compounds database maintanied by Colby College:

hypertext transfer protocol: //www.colby.edu/chemistry/cmp/cmp.html

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Examining The Separation Of Naphthalene And Biphenyl Biology. (2017, Jul 11). Retrieved from


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