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Thon Bunheng HCM UT university of technology

CHAPTER 3:Crystallization(1)
1. Crystallization is the most important method for the purification (tinh chế)of solid(rắn) organic compounds. 2 crystalline (kết tinh)organic substance(bản chất) is made up of a three-dimensional array(chuỗi) of molecules Held (liên lết)together(giữ chặt) primarily(chủ yếu) by vander Waals forces(lực). Crystals (tinh thể)can be grown from the molten(nóng chảy) state just as water is frozen(đóng băng,đông lạnh) into ice, but it is not easy to remove(loại bỏ,di chuyển)impurities(tạp chất) from crystals(tinh thể) made in this way(phương pháp). As the solvent(dung môi) cools(mát mát) , the solution(dung dịch) become saturate with respect to the substance , which then crystallize. As the perfectly regular array of a crystal is formed, foreign molecular are excluded and thus the crystal is one pure substance. Soluble impurities stay in solution because they are not concentrated enough to saturate the solution. The crystal are collected by filtration, the surface of the crystals is washed with cold solvent to remove the adhering impurities and then the crystals are dried. The process of crystallization can be broken into seven discrete steps: choosing the solvent, dissolving the solute , decolorizing the solution, removing suspended solids, crystallizing the solute, collecting and washing the crystal, and drying the product. Choosing the solvent and solvent pairs 1. Hydrocarbon solvents such as hexane will dissolve hydrocarbons and other nonpolar compounds, and hydroxylic solvents such as water and ethanol will dissolve polar compounds. 2. The best crystallization solvent (and none is ideal ) will dissolve the solute when the solution is hot but not when the solution is cold; it will either not dissolve the impurities at all or it will dissolve them very well ( so they won’t crystallize out along with the solute);it will not react with the solute; and it will be nonflammable, nontoxin , inexpensive, and very volatile ( so it can be removed from the crystals). 3. To used a mixed solvent dissolve the crystals in the better solvent and add the poorer solvent to the hot solution until it becomes cloudy and the solution is saturated with the solute. Dissolving the solute 1. It is not difficult to superheat the solution,i.e., heat is above the boiling point with no boiling taking place.once the solution does boil it does so with explosive violence. 2. A glass rod with a flattened end can sometimes be of use in crushing large particles of solute to speed up the dissolving prosess. 3. Note how rapidly most of the material dissolves and then stop adding solvent when you

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The filter paper should fit entirely inside the rim of the funnel. the crystals must be separated from the icecold mother liquor ( the filtrate). in the past . the charcoal function like hundred of boiling chips and will cause the solution to boil over/ Filtering suspended solids 1. The funnel is stemless so that the saturated solution being filtered will not have a chance to cool and clog the stem with crystals. 8. The solid remaining in the flask and the inside of the flask should be rinsed with a few milliliters of the solvent in order to recover as much of the product as possible. The filtering process can be speeded up somewhat by blowing a slow current of air into the flask in the hood or using an aspirator tube to pull vapors into the aspirator. 7. 5. Vacuum filtration is not use because the hot solvent will cool during the process and the product will crystallize in the filter. Since the filtrate has been diluted in order to prevent it from crystal-lizing during the filtration process the excess solvent must now be removed by boiling the solution. laboratory manuals have advocated the use of finely powdered activated charcoal for removal of colored impurities. Once crystallization is complete . 6. 4. The filtration of hot . 2. 5. . undissolved material noted at this point could be an insoluble impurity that never will dissolve. it will absorbed some of the product in addition to the impurities. Suspect that almost all of the desired material has dissolved. The most common way to produce a vacuum in the organic laboratory for filtration purposes is by employing a water aspirator. 6. . It can be added in small portion until the solution is decolorized and the size of the pieces make it easy to remove from solution.Thon Bunheng HCM UT university of technology 1. decantation. Be careful not to add the charcoal pieces to a superheated solution . 2. or removal of the solvent using a Pasteur pipette. It is often possible to pour off (decant) the hot solution leaving the insoluble material behind . 3. Collecting and washing the crystals 1. 2. and dried. Activated charcoal has an extremely large surface area per gram ( several hundred square meters) and can bind a large number of molecular to this surface. 4. washed with ice-cold solvent. 3. If too little charcoal is added the solution will still be colored after filtration. this is especially easy if the solid is granular like sodium sulfate. saturated solution to remove solid impurities or charcoal can be done in a number of ways. it is fluted to allow rapid filtration.making repetition necessary : if too much is added . Declorizing the solution The impurities can be adsorbed onto the surface of activated charcoal by simply boiling the solution with charcoal. Process include gravity filtration . pressure filtration.

CHAPTER 5:Distilation(2) 1. The system can be opened to the atmosphere by removing the hose from the small filter flask or by opening the screw clamp on the trap. In the laboratory the successive condensation an distillations that occur in the bubble cap column take place in a distillation column. Once the crystals have been washed on the Hirsch funnel or Buchner funnel. Each theoretical plate corresponding to one distillation and condensation. the filtrate and washings can be combined and evaporated to the point of saturation to obtain a second crop of crystals-hence the necessity for having a clean receptacle for the filtrate. Air is efficient entranced in the water rushing through the aspirator so that it will produce a vacuum roughly equal to the vapor pressure of the water going through it. 5.Thon Bunheng HCM UT university of technology 3. The ability of different column packing’s to separate two materials of differing boiling points is evaluated by calculating the number of theoretical plates. Regardless of the method used to collect the crystals on either a macroscale or microscale . Drying the produce 1. The crystals can then be turned out of the funnel and squeezed between sheets of filter paper to remove the last bit of solvent before final drying on a watch glass. 2. 6. 4. 2. 5. Press them with a clean cork or other flat object and allow air to pass through them until they are substantially dry. The more volatile substances travel through the bubble cap to the next higher plate where some of the less volatile components condense. The origins of distillation are lost in antiquity as man is his thirst for more potent beverages found that dilute solution of alcohol from fermentation could be separated into alcohol-rich and water-rich portions by heating the solution to boiling and condensing the vapors above the boiling liquid-the process of distillations . . Perhaps the easiest to understand is the bubble cap column used to fractionally distill crude oil. 3. As high boiling liquid material accumulates on a plate it descends through the overflow pipe to the next lower plate and vapor rises through the bubble cap to the next higher plate. 4.

Thon Bunheng HCM UT university of technology 7. 2. Distillation can also be done at the lower pressure that can be achieved by an or an aspirator with substantial reduction of boiling point. O2 . followed by a comparison between some of the well-khnow types of oil. and other some metals. A series of simple distillations take place within a fractionating column and it is important that complete equilibrium be attained between the ascending vapors and the descending liquid. known as hydrocarbon with very amount of nonhydrocarbon containing S . When a distillation is carried out in a system open to the air and the boiling point is thus dependent on existing air pressure . 10. the vapor pressure at a given temperature decreases and a higher temperature is required for boiling. 4. Chemical composition describes and identifies the individual chemical compounds isolated from crude oils over the years. 9. and even impossible on a small scale. The number of theoretical plates is proportional to the height of the column. 13. The major constituent of most crude oil and its products are hydrocarbon compound . 14. Although not obvious.the more plates the column will have and the more efficient it will be. so various packings are evaluated according to the equivalent to theoretical plate (HETP). . 11. A mixture of liquids of a certain definite composition that distills at a constant temperature without change in compositions is called an azeoprope . Nearly all petroleum deposits are made up of a mixture of chemical compounds that consist of hydro and carbon .N2 . Characteristics and classification of crude oils based on correlation indexes and crude assays are presented . 8. 5. Carrying out a fractional distillation on the truly micro scale is impossible. and hence with increasing concentration of nonvolatile suger molecules and decreases concentration of water . 95% ethanol is such an azeotrope/ 12. which are made up of hydrogen and carbon only. The vapor pressure of the solution is dependent upon the number of water molecules present is a given volume. CHAPTER 2:Composition and characteristics of crude petroleum (4) Unit 4 composition and characteristics of crude petroleum 1. composition of crude oil may be studies by two methods: chemical approach and physical method. Azeotropes have constant boiling points that can be either above or below the boiling points of the individual components. the most important variable contributing to a good fractional distillation is rate at which distillation is carried out. 15. 3. the prevailing barometric pressure should be noted and allowance made for appreciable deviations from the accepted boiling point temperature. In general .

Density is defined as the mass of a unit volume of material at a specified temperature. many sulfur compounds have been found in the liquid phase in the form of organosulfur. thus producting hydrogen sulfide during crude processing. It has the dimensions of grams per cubic centimeters. Cycloalkanes and bicycloalkanes are normally present in crude oils and its fractions in variable proportions. 2. Naphtha cuts with high percentage of naphthenes would make an excellent feedstock for aromatization. As may be seen . 16.Thon Bunheng HCM UT university of technology 6. 11. 13. 6. . Hydrotreatment may also be used to reduce the metal content in heavy feeds to catalytic cracking. hence inidicating the “ pumpabiliy” of oil. crude oils from different locations may vary in appearance and viscosity and also vary in their usefulness as producers for final products. The crude sample is usually burned in an atmosphere of air and the ash is the material left unburned. 4. 3. 5. Carbon residue is percentage of carbon by weight for coke . 10. 8.and heavy fuels found by evaporating oil to dryness under standard laboratory conditions. in some case depositing elemental sulfur. The occurrence of metallic constituents in crude oils is of considerably greater interest to the petroleum industry than might be expected from the very small amounts present. Nitrogen in petroleum is in the from of heterocyclic compound and may be classified as basic and nonbasic. However. It has been confirmed by mass spectroscopic techniques that condensed-ring aromatic hydrocarbons and heterocyclic compounds are the major compound of asphaltenes. 12. 14. 9. Physical methods 1. asphat . In addition to the gaseous sulfur compound in crude oil . the derived relationships between the density and its fractional composition were only valid if they were applied to a certain type of petroleum. 7. Polysulfide are more complicated sulfur component and they may decompose . Dinuclear and polynuclear aromatic compounds are present in heavier petroleum fraction and residues. Many of the organic sulfur compound are not thermally stable . Basic nitrogen compound are mainly composed of pyridine homologs and have the tendency to exist in the high-boiling fractions and residues. 15. The viscosity is the measure of the resistance of a liquid to flow .

8. Chemical ………….. Numerous attempt have been made to devise a system to classify crude oils into type based on the predominate hydrocarbon series present in the crude..and………. For completeness. Dinuclear and polynuclear aromatic compounds are present in heavier petroleum fractions and………….O2.asphaltic. Nitrogen in petroleum is in the form of …………. Nearly all petroleum deposit are made up of a mixture of chemical compounds that consist of …….Thon Bunheng HCM UT university of technology 7. followed by a comparison between some of the well. 4. Most important are the following: Sulfur. the latter are more valuable than the former. Basic nitrogen compounds are mainly composed of pyridine ………… and have the tendency to exist in the high-boiling fractions and residue. 9.of most crude oils and its products are hydrocarbon………. 1.compounds. Nitrogen. There are several correlations between yield and type of crude in terms of aromaticity and parafinicity.. . known as hydrocarbons.streams. compounds and may be classified as basic and nonbasic. The following sulfur compounds are typical: Mercaptans...of crude oils based on …………indexes and crude ………are presented.. operated at high efficiency . Salts in crude oil and in heavier products may create serious corrosion problem .. The major …………. which are made up of hydrogen and carbon only. we should mention that other types of nonhydrocarbon compound occur in crude oils and ………. naphthenic . 10.know type of oil. Hydrogen sulfide is a toxic gas that can envole during storage or in the processing of hydrocarbon. They may either be straight – chain or…………. Characterization and ………….describes and …………the individual chemical compounds isolated from crude oil over the years. 7.. 9. Oxygen and ………. composition of crude oil may be studied by two methods: chemical ………and physical methods. and other some metals. especially in the top-tower zone and the overhead condenser in distillation columns.. N2 . Alkanes are relatively nonreactive compounds in comparison to other series. because they are useful for the production of high – octane gasoline. 11. In united states crude oil are classified into three types: paraffinic . 2. ……… and Polysulfides. 10. with varying amounts of nonhydrocarbons containing S . 12. 8.. 5.. 6. The basic of the assay is the distillation of a crude oil under specified conditions in a batch laboratory distillation column . In general. 3.

under standard laboratory conditions.was the principal specification for petroleum products.. of a liquid to flow. hence indicating the “pump ability: of oil. 19. it is necessary to produce ………….. 25. The ………… is the measure of the ………. 23 A comparison of the …………..left unburned. Having discussed the various chemicals found in crude oils and realizing not only the complexity of the mixture but the difficulty of specifying a crude oil as a particular ……….. 12.. we can understand why the early petroleum producers adopted the ………methods generally used for classification. The crude sample is usually ………. The …………. One can summarize the two ………… of examining crude oils as follows: chemical ……………. CHAPTER 7:Solutions(5) 7. data in the form of what is known as an “ assay ’’. nickel. corrosion problems.. There are several correlations between . define what products can be obtained from a crude oil and contribute effectively to safety and environmental aspects. Earlier. 22 The basis of the assay is the ……….. In order to establish a basis for the comparison between different types of crude oil. 24. especially in the top tower zone and the ………. arsenic.condensers in distillation columns.Thon Bunheng HCM UT university of technology 11. The occurrence of metallic constituents in crude oils is of considerably greater interest to the petroleum industry than might be expected from the very small amounts present.. In addition. these ……….. Correlation indexes or characterization …………are used in the petroleum industry to indicate the crude type or class.. 21 .. 14. the derived relationships between the density and its …………composition were only valid if they were applied to a certain type of ……….. and Asphaltic. and vanadium are ………… poisons for process catalysts.and type of crude in terms of aromaticity and parafinicity. ………. 18. and physical properties.1 What are solutions? Why are they important? . in an atmosphere of air and the ash is the …………. of chemicals. operated at high efficiency. lead. of different types of crude oil over the distillation rage could be made via a ………. 15. ………. compounds are usually concentrated in the heavier ………… and in crude oil residues. 13. of a crude oil under specified conditions in a bath …………distillation column.. 17.. and heavy fuels found by evaporating oil to ……….that relates the following: the density of distillate fractions and their mid-boiling points. In United States crude oils are classified into three types: Paraffinic. 20.. However. 16. ………. In particular. Salt in crude oil and in heavier products may create …………. Carbon residue is the percentage of carbon by weight for coke. Metal contents are reported in parts per million (ppm).

. ……… food molecules to simple. it now …. one important example is the use of organic solvents to dissolve ………. which are eliminated from the body. 16.. separation. if each is dissolved in ………. to come into close contact. a precipitation …………. Digestion is largely a process of ……… down complex.. in geochemical processes.Thon Bunheng HCM UT university of technology 1. the chemist can tell how much of a particular kind of chemical is in a solution.. such as carbon dioxide. 20.. for example. Dissolution in rainwater is the most common process by which ………… pollutants are removed from air. 6. detergents and dyes. occurs. at lower temperature than pure water. Some of its other properties have changed. 14. in which calcium chloride and sodium fluoride in aqueous solutions (aq) react to produce calcium fluoride solid (s) and a solution of sodium chloride. soluble molecules that may be carried be the blood to the body cells. 13.. In water. Solutions transport environmental chemical ………… in the aquatic environment and are crucial …………. 4. For living things the most important ……… of solutions is to carry molecules and ions to and from cells. The solution freezes at a much lower temperature than pure water. fertilizer. In chemical industry. On the return trip the blood carries ………. 19.. and physical processing. The sugar is still there. 15. so that they can react. A solution ……….to allow chemical …….products. thus ………… the liquid from freezing and cracking the engine block. the simple sugar glucose and some other substances may be …. Body-fluids consist of ………. By measuring how much of solution is ……….at a higher temperature and ………. solutions enable chemical reactions to occur that …….. solvents are employed for ……………. 7. to complete a reaction in a procedure called …………. 11. in materials being ………. ………. The dissolved sugar is called solute. 5. The calcium fluoride product does not stay in solution but forms a …………. 12. 2. it is insoluble... 17. Industrial use of solutions: natural brines. However. Many important environmental chemical processes occur in solution and at the ………… of solutions with solids and gases. 10. directly into the veins of an ill or injured person who cannot take food through the mouth. 8. and oil from metal parts after they have been fabricated.. which is called the ……….. the ……… break away from the crystals and spread throughout the liquid. Solvents are also used for cleaners. too. Chemists use many different ……… of solution that undergo chemical reactions with other kinds of ………. 9. One of the most important properties of solutions is their ……. In other cases. Some of these reactions are important in geology. solutions which are then mixed. Pollutant pesticides and …………. 18.. which need them for energy and production of more cell material.. 3. solutions. waste chemicals are transported in solution as surface water or groundwater. Acid rain is a solution of strong ………acids in water. but it is dissolved in the water.

some of the …………are driven out of solution. one that ………… quickly to form a vapor. in water. 23.. 34. They ………. 38. of moles of solute dissolved in a liter of solution. are dissolved in solvents.with the water molecules and occupy spaces that open up between water molecules to accommodate the N2 and O2 molecules. in organic solvents instead.. 24. this process is called ………. In describing a solution it is necessary to do …………. it leaves the coating behind as a thin layer.. 35. .. Both benzene and carbon tetrachloride are toxic and can damage the body in cases of excess exposure. to the atmosphere. The molar concentration of a solution is the ……. printing inks. or by a particular amount of solvent. its concentration. The terms part per million and milligrams per liter are both frequently used in reference to levels of …………. 32. Sugars and many other biologically important compounds are also ………. 33. 27. when it evaporates. 36. material dissolved in a particular amount of solution. 28.... It is necessary to have …………. 31. The chemical makeup s……… fibers. In the past. 29.. Concentration of ……… dissolved in water is frequently measured by atomic ………… spectroscopy. Some organic solvents. 26. through small holes in a special die to make individual filaments of the fiber. One of the most important uses for solvents is in ………. Hydrogen ………. 37. that appear in heated water just before it boils.... However. such as benzene.through the skin and inhalation through the lungs. The toxicity hazard of solvents arises from ……….. though less so now solvents used for parts cleaning were allowed to ………….in water. pollutants. are even more of a fire ……. The hydrogen chloride molecule ………. 30. and antirust formulation. 25. to specify what that solvent is and what the solutes are. such as rayon. of a hydrogen atom bonded to a chlorine atom with a ………. that is. than gasoline.Thon Bunheng HCM UT university of technology 21. lacquers. If the water is heated. The concentration of a solution is the amount of ………. which include paint. information about a solution.. The volatile liquid. bond. a major source of atmospheric ………. greases and oils generally are not soluble in water but ……….. 22. is one of the main reasons that some proteins can be put in water solution or held suspended in water as extremely small particles called colloidal particles. Often it is necessary to make a less concentrated solution from a more concentrated solution. This may be observed as the small ………. and then forced under very high ……….

. with regard to that solute. A solution that has dissolved as much of a solute as possible is said to be ……….Thon Bunheng HCM UT university of technology 39. The concentration of the substance in the saturated solution is the ……………….