Thon Bunheng HCM UT university of technology

CHAPTER 3:Crystallization(1)
1. Crystallization is the most important method for the purification (tinh ch)of solid(rn) organic compounds. 2 crystalline (kt tinh)organic substance(bn cht) is made up of a three-dimensional array(chui) of molecules Held (lin lt)together(gi cht) primarily(ch yu) by vander Waals forces(lc). Crystals (tinh th)can be grown from the molten(nng chy) state just as water is frozen(ng bng,ng lnh) into ice, but it is not easy to remove(loi b,di chuyn)impurities(tp cht) from crystals(tinh th) made in this way(phng php). As the solvent(dung mi) cools(mt mt) , the solution(dung dch) 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 wont 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

2. 3. 4. 5. 6.

Thon Bunheng HCM UT university of technology

1. 2. 3. 4.

5. 6.

Suspect that almost all of the desired material has dissolved. undissolved material noted at this point could be an insoluble impurity that never will dissolve. Declorizing the solution The impurities can be adsorbed onto the surface of activated charcoal by simply boiling the solution with charcoal. 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. in the past , laboratory manuals have advocated the use of finely powdered activated charcoal for removal of colored impurities. If too little charcoal is added the solution will still be colored after filtration, ,making repetition necessary : if too much is added , it will absorbed some of the product in addition to the impurities. 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. Be careful not to add the charcoal pieces to a superheated solution ; the charcoal function like hundred of boiling chips and will cause the solution to boil over/ Filtering suspended solids 1. The filtration of hot , saturated solution to remove solid impurities or charcoal can be done in a number of ways. Process include gravity filtration , pressure filtration, decantation, or removal of the solvent using a Pasteur pipette. 2. Vacuum filtration is not use because the hot solvent will cool during the process and the product will crystallize in the filter. 3. It is often possible to pour off (decant) the hot solution leaving the insoluble material behind . this is especially easy if the solid is granular like sodium sulfate. 4. 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. 5. The funnel is stemless so that the saturated solution being filtered will not have a chance to cool and clog the stem with crystals. 6. The filter paper should fit entirely inside the rim of the funnel; it is fluted to allow rapid filtration. 7. 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. 8. 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. Collecting and washing the crystals 1. Once crystallization is complete , the crystals must be separated from the icecold mother liquor ( the filtrate), washed with ice-cold solvent, and dried. 2. The most common way to produce a vacuum in the organic laboratory for filtration purposes is by employing a water aspirator.

Thon Bunheng HCM UT university of technology

3. 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. 4. 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. 5. Regardless of the method used to collect the crystals on either a macroscale or microscale , 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. Drying the produce 1. Once the crystals have been washed on the Hirsch funnel or Buchner funnel. Press them with a clean cork or other flat object and allow air to pass through them until they are substantially dry. 2. 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.

CHAPTER 5:Distilation(2)
1. 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 . 2. Perhaps the easiest to understand is the bubble cap column used to fractionally distill crude oil. 3. The more volatile substances travel through the bubble cap to the next higher plate where some of the less volatile components condense. 4. 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. 5. In the laboratory the successive condensation an distillations that occur in the bubble cap column take place in a distillation column. 6. The ability of different column packings to separate two materials of differing boiling points is evaluated by calculating the number of theoretical plates. Each theoretical plate corresponding to one distillation and condensation.

Thon Bunheng HCM UT university of technology

7. The number of theoretical plates is proportional to the height of the column, so various packings are evaluated according to the equivalent to theoretical plate (HETP);the more plates the column will have and the more efficient it will be. 8. Although not obvious, the most important variable contributing to a good fractional distillation is rate at which distillation is carried out. 9. 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. 10. Carrying out a fractional distillation on the truly micro scale is impossible, and even impossible on a small scale. 11. A mixture of liquids of a certain definite composition that distills at a constant temperature without change in compositions is called an azeoprope ; 95% ethanol is such an azeotrope/ 12. Azeotropes have constant boiling points that can be either above or below the boiling points of the individual components. 13. The vapor pressure of the solution is dependent upon the number of water molecules present is a given volume; and hence with increasing concentration of nonvolatile suger molecules and decreases concentration of water , the vapor pressure at a given temperature decreases and a higher temperature is required for boiling. 14. When a distillation is carried out in a system open to the air and the boiling point is thus dependent on existing air pressure , the prevailing barometric pressure should be noted and allowance made for appreciable deviations from the accepted boiling point temperature. 15. Distillation can also be done at the lower pressure that can be achieved by an or an aspirator with substantial reduction of boiling point.

CHAPTER 2:Composition and characteristics of crude petroleum (4)

Unit 4 composition and characteristics of crude petroleum 1. Characteristics and classification of crude oils based on correlation indexes and crude assays are presented , followed by a comparison between some of the well-khnow types of oil. 2. Chemical composition describes and identifies the individual chemical compounds isolated from crude oils over the years. 3. In general , composition of crude oil may be studies by two methods: chemical approach and physical method. 4. Nearly all petroleum deposits are made up of a mixture of chemical compounds that consist of hydro and carbon , known as hydrocarbon with very amount of nonhydrocarbon containing S ,N2 , O2 , and other some metals. 5. The major constituent of most crude oil and its products are hydrocarbon compound , which are made up of hydrogen and carbon only.

Thon Bunheng HCM UT university of technology

6. Cycloalkanes and bicycloalkanes are normally present in crude oils and its fractions in variable proportions. 7. Naphtha cuts with high percentage of naphthenes would make an excellent feedstock for aromatization. 8. Dinuclear and polynuclear aromatic compounds are present in heavier petroleum fraction and residues. 9. It has been confirmed by mass spectroscopic techniques that condensed-ring aromatic hydrocarbons and heterocyclic compounds are the major compound of asphaltenes. 10. In addition to the gaseous sulfur compound in crude oil , many sulfur compounds have been found in the liquid phase in the form of organosulfur. 11. Many of the organic sulfur compound are not thermally stable , thus producting hydrogen sulfide during crude processing. 12. Polysulfide are more complicated sulfur component and they may decompose , in some case depositing elemental sulfur. 13. Nitrogen in petroleum is in the from of heterocyclic compound and may be classified as basic and nonbasic. 14. Basic nitrogen compound are mainly composed of pyridine homologs and have the tendency to exist in the high-boiling fractions and residues. 15. 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. 16. Hydrotreatment may also be used to reduce the metal content in heavy feeds to catalytic cracking. Physical methods

1. As may be seen , crude oils from different locations may vary in appearance and viscosity and also vary in their usefulness as producers for final products. 2. However, the derived relationships between the density and its fractional composition were only valid if they were applied to a certain type of petroleum. 3. Density is defined as the mass of a unit volume of material at a specified temperature. It has the dimensions of grams per cubic centimeters. 4. Carbon residue is percentage of carbon by weight for coke , asphat ,and heavy fuels found by evaporating oil to dryness under standard laboratory conditions. 5. The viscosity is the measure of the resistance of a liquid to flow , hence inidicating the pumpabiliy of oil. 6. The crude sample is usually burned in an atmosphere of air and the ash is the material left unburned.

Thon Bunheng HCM UT university of technology

7. Salts in crude oil and in heavier products may create serious corrosion problem , especially in the top-tower zone and the overhead condenser in distillation columns. 8. Hydrogen sulfide is a toxic gas that can envole during storage or in the processing of hydrocarbon. 9. The basic of the assay is the distillation of a crude oil under specified conditions in a batch laboratory distillation column , operated at high efficiency . 10. 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. 11. In united states crude oil are classified into three types: paraffinic , naphthenic ,asphaltic. 12. There are several correlations between yield and type of crude in terms of aromaticity and parafinicity.

1. Characterization and ..of crude oils based on indexes and crude are presented, followed by a comparison between some of the well- know type of oil. 2. In general, composition of crude oil may be studied by two methods: chemical and physical methods. 3. Chemical ..describes and the individual chemical compounds isolated from crude oil over the years. 4. Nearly all petroleum deposit are made up of a mixture of chemical compounds that consist of ..and, known as hydrocarbons, with varying amounts of nonhydrocarbons containing S , N2 ,O2, and other some metals. 5. The major ..of most crude oils and its products are hydrocarbon., which are made up of hydrogen and carbon only. 6. Alkanes are relatively nonreactive compounds in comparison to other series. They may either be straight chain or..., the latter are more valuable than the former, because they are useful for the production of high octane gasoline. 7. Dinuclear and polynuclear aromatic compounds are present in heavier petroleum fractions and.. 8. For completeness, we should mention that other types of nonhydrocarbon compound occur in crude oils and ..streams. Most important are the following: Sulfur, Nitrogen, Oxygen and ..compounds. 9. The following sulfur compounds are typical: Mercaptans, and Polysulfides. 10. Nitrogen in petroleum is in the form of . compounds and may be classified as basic and nonbasic. Basic nitrogen compounds are mainly composed of pyridine and have the tendency to exist in the high-boiling fractions and residue.

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. The .. compounds are usually concentrated in the heavier and in crude oil residues. 12. 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 . of chemicals, we can understand why the early petroleum producers adopted the methods generally used for classification. 13. Earlier, .was the principal specification for petroleum products. However, the derived relationships between the density and its composition were only valid if they were applied to a certain type of .. 14. Carbon residue is the percentage of carbon by weight for coke. ., and heavy fuels found by evaporating oil to .. under standard laboratory conditions. 15. The is the measure of the .. of a liquid to flow, hence indicating the pump ability: of oil. 16. The crude sample is usually .. in an atmosphere of air and the ash is the ..left unburned. 17. In particular, arsenic, nickel, lead, and vanadium are poisons for process catalysts. Metal contents are reported in parts per million (ppm). 18. Salt in crude oil and in heavier products may create . corrosion problems, especially in the top tower zone and the ..condensers in distillation columns. 19. In addition, these . define what products can be obtained from a crude oil and contribute effectively to safety and environmental aspects. 20. One can summarize the two of examining crude oils as follows: chemical . and physical properties. 21 . In order to establish a basis for the comparison between different types of crude oil, it is necessary to produce . data in the form of what is known as an assay . 22 The basis of the assay is the . of a crude oil under specified conditions in a bath distillation column, operated at high efficiency. 23 A comparison of the .. of different types of crude oil over the distillation rage could be made via a ..that relates the following: the density of distillate fractions and their mid-boiling points. 24. In United States crude oils are classified into three types: Paraffinic, . and Asphaltic. 25. Correlation indexes or characterization are used in the petroleum industry to indicate the crude type or class. There are several correlations between ......and type of crude in terms of aromaticity and parafinicity.

CHAPTER 7:Solutions(5)
7.1 What are solutions? Why are they important?

Thon Bunheng HCM UT university of technology

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

Thon Bunheng HCM UT university of technology

21. 22. 23. 24. 25. 26. 27.

In the past, though less so now solvents used for parts cleaning were allowed to . to the atmosphere, a major source of atmospheric .. pollutants. The chemical makeup s fibers, such as rayon, are dissolved in solvents, and then forced under very high .. through small holes in a special die to make individual filaments of the fiber. One of the most important uses for solvents is in , which include paint, printing inks, lacquers, and antirust formulation. The volatile liquid, one that quickly to form a vapor; when it evaporates, it leaves the coating behind as a thin layer. Some organic solvents, such as benzene, are even more of a fire .. than gasoline. Both benzene and carbon tetrachloride are toxic and can damage the body in cases of excess exposure. The toxicity hazard of solvents arises from ..through the skin and inhalation through the lungs.

Sugars and many other biologically important compounds are also ..in water. However, greases and oils generally are not soluble in water but . in organic solvents instead. 28. Hydrogen .. 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. 29. They .with the water molecules and occupy spaces that open up between water molecules to accommodate the N2 and O2 molecules. 30. If the water is heated, some of the are driven out of solution. This may be observed as the small .. that appear in heated water just before it boils. 31. The hydrogen chloride molecule . of a hydrogen atom bonded to a chlorine atom with a . bond. 32. In describing a solution it is necessary to do ., that is, to specify what that solvent is and what the solutes are. 33. It is necessary to have .. information about a solution, its concentration. 34. The concentration of a solution is the amount of .. material dissolved in a particular amount of solution, or by a particular amount of solvent. 35. The terms part per million and milligrams per liter are both frequently used in reference to levels of .. in water. 36. The molar concentration of a solution is the .. of moles of solute dissolved in a liter of solution. 37. Often it is necessary to make a less concentrated solution from a more concentrated solution; this process is called ... 38. Concentration of dissolved in water is frequently measured by atomic spectroscopy.

Thon Bunheng HCM UT university of technology

39. A solution that has dissolved as much of a solute as possible is said to be . with regard to that solute. The concentration of the substance in the saturated solution is the .