What hydrocarbons are contained in natural gas. Preparation of aromatic hydrocarbons

Lesson objectives:

Educational:

Develop students' cognitive activity.
To familiarize students with natural sources of hydrocarbons: oil, natural gas, coal, their composition and processing methods.
To study the main deposits of these resources globally and in Russia.
Show their significance in the national economy.
Consider environmental protection issues.

Educational:

Cultivating interest in studying the topic, instilling speech culture in chemistry lessons.

Educational:

Develop attention, observation, listening skills and drawing conclusions.

Pedagogical methods and techniques:

Perceptual approach.
Gnostic approach.
Cybernetic approach.

Equipment: Interactive whiteboard, multimedia, electronic textbooks of MarSTU, Internet, collections “Oil and the main products of its processing”, “Coal and the most important products of its processing”.

During the classes

I. Organizational moment.

I introduce the purpose and objectives of this lesson.

II. Main part.

The most important natural sources of hydrocarbons are: oil, coal, natural and associated petroleum gases.

Oil – “black gold” (I introduce students to the origin of oil, main reserves, production, composition of oil, physical properties, and refined products).

During the rectification process, oil is divided into the following fractions:

I am showing samples of fractions from the collection (demonstration accompanied by explanation).

Distillation gases– a mixture of low-molecular hydrocarbons, mainly propane and butane, with a boiling temperature of up to 40 ° C,
Gasoline fraction (gasoline)– HC composition C 5 H 12 to C 11 H 24 (boiling point 40-200°C, with a finer separation of this fraction one gets gas oil(petroleum ether, 40 - 70°C) and petrol(70 - 120°C),
Naphtha fraction– HC composition from C 8 H 18 to C 14 H 30 (boil temperature 150 - 250°C),
Kerosene fraction– HC composition from C 12 H 26 to C 18 H 38 (boil temperature 180 - 300°C),
Diesel fuel– HC composition from C 13 H 28 to C 19 H 36 (boil temperature 200 - 350°C)

Residue from oil refining – fuel oil– contains hydrocarbons with the number of carbon atoms from 18 to 50. Distillation under reduced pressure from fuel oil produces solar oil(C 18 H 28 – C 25 H 52), lubricating oils(C 28 H 58 – C 38 H 78), petrolatum And paraffin– low-melting mixtures of solid hydrocarbons. Solid residue from fuel oil distillation – tar and products of its processing - bitumen And asphalt used for making road surfaces.

The products obtained as a result of oil rectification are subjected to chemical processing. One of them is cracking.

Cracking is the thermal decomposition of petroleum products, which leads to the formation of hydrocarbons with a smaller number of carbon atoms in the molecule. (I use the MarSTU electronic textbook, which talks about the types of cracking).

Students compare thermal and catalytic cracking. (Slide No. 16)

Thermal cracking.

The breakdown of hydrocarbon molecules occurs at a higher temperature (470-5500 C). The process proceeds slowly, hydrocarbons with an unbranched chain of carbon atoms are formed. Gasoline obtained as a result of thermal cracking, along with saturated hydrocarbons, contains many unsaturated hydrocarbons. Therefore, this gasoline has greater detonation resistance than straight distilled gasoline. Thermally cracked gasoline contains many unsaturated hydrocarbons, which easily oxidize and polymerize. Therefore, this gasoline is less stable during storage. When it burns, various parts of the engine can become clogged.

Catalytic cracking.

The splitting of hydrocarbon molecules occurs in the presence of catalysts and at a lower temperature (450-5000 C). The main focus is on gasoline. They are trying to get more of it and always of better quality. Catalytic cracking appeared precisely as a result of the long-term, persistent struggle of oil workers to improve the quality of gasoline. Compared to thermal cracking, the process proceeds much faster, and not only the splitting of hydrocarbon molecules occurs, but also their isomerization, i.e. hydrocarbons with a branched chain of carbon atoms are formed. Catalytic cracked gasoline is even more resistant to detonation than thermally cracked gasoline.

Coal. (I introduce students to the origin of coal, main reserves, production, physical properties, processed products).

Origin: (I use the electronic textbook of MarSTU, where they talk about the origin of coal).

Main reserves: (slide number 18) On the map I show students the largest coal deposits in Russia in terms of production volume - these are the Tunguska, Kuznetsk, and Pechora basins.

Production:(I use the MarSTU electronic textbook, where they talk about coal mining).

Coke gas– which includes H 2, CH 4, CO, CO 2, impurities of NH 3, N 2 and other gases,
Coal tar– contains several hundred different organic substances, including benzene and its homologues, phenol and aromatic alcohols, naphthalene and various heterocyclic compounds,
Nadsmolnaya, or ammonia water– contains dissolved ammonia, as well as phenol, hydrogen sulfide and other substances,
Coke– solid coking residue, almost pure carbon.

Natural and petroleum associated gases. (I introduce students to the main reserves, production, composition, processed products).

III. Generalization.

In the summary part of the lesson, I created a test using the Turning Point program. The students armed themselves with remote controls. When a question appears on the screen, by pressing the appropriate button, they select the correct answer.

1. The main components of natural gas are:

Ethane;
Propane;
Methane;
Butane.

2. Which fraction of petroleum distillation contains from 4 to 9 carbon atoms per molecule?

Naphtha;
Gas oil;
Petrol;
Kerosene.

3. What is the purpose of cracking heavy petroleum products?

Methane production;
Obtaining gasoline fractions with high detonation resistance;
Synthesis gas production;
Hydrogen production.

4. Which process is not related to oil refining?

Coking;
Fractional distillation;
Catalytic cracking;
Thermal cracking.

5. Which of the following events is the most dangerous for aquatic ecosystems?

Violation of oil pipeline tightness;
Oil spill as a result of a tanker accident;
Violation of technology during deep oil production on land;
Transportation of coal by sea.

6. From methane, which forms natural gas, we obtain:

Synthesis gas;
Ethylene;
Acetylene;
Butadiene.

7. What features distinguish catalytic cracking gasoline from straight distilled gasoline?

Presence of alkenes;
Presence of alkynes;
The presence of hydrocarbons with a branched chain of carbon atoms;
High detonation resistance.

The test result is immediately visible on the screen.

Homework:§ 10, ex.1 – 8

Literature:

L.Yu. Alikberova “Entertaining chemistry”. – M.: “AST-Press”, 1999.
O.S. Gabrielyan, I.G. Ostroumov “Handbook for chemistry teachers, grade 10.” – M.: “Blik and K,” 2001.
O.S. Gabrielyan, F.N. Maskaev, S.Yu. Ponomarev, V.I. Terenin “Chemistry 10th grade.” – M.: “Drofa”, 2003.

Compounds consisting only of carbon and hydrogen atoms.

Hydrocarbons are divided into cyclic (carbocyclic compounds) and acyclic.

Cyclic (carbocyclic) are compounds that contain one or more cycles consisting only of carbon atoms (in contrast to heterocyclic compounds containing heteroatoms - nitrogen, sulfur, oxygen, etc.). Carbocyclic compounds, in turn, are divided into aromatic and non-aromatic (alicyclic) compounds.

Acyclic hydrocarbons include organic compounds whose carbon skeleton molecules are open chains.

These chains can be formed by single bonds (alkanes), contain one double bond (alkenes), two or more double bonds (dienes or polyenes), or one triple bond (alkynes).

As you know, carbon chains are part of most organic matter. Thus, the study of hydrocarbons is of particular importance, since these compounds are the structural basis of other classes of organic compounds.

In addition, hydrocarbons, especially alkanes, are the main natural sources of organic compounds and the basis of the most important industrial and laboratory syntheses (Scheme 1).

You already know that hydrocarbons are the most important type of raw material for the chemical industry. In turn, hydrocarbons are quite widespread in nature and can be isolated from various natural sources: oil, associated petroleum and natural gas, coal. Let's take a closer look at them.

Oil- a natural complex mixture of hydrocarbons, mainly alkanes of linear and branched structure, containing from 5 to 50 carbon atoms in molecules, with other organic substances. Its composition significantly depends on the place of its extraction (deposit); in addition to alkanes, it may contain cycloalkanes and aromatic hydrocarbons.

Gaseous and solid components of oil are dissolved in its liquid components, which determines its state of aggregation. Oil is an oily liquid of a dark (brown to black) color with a characteristic odor, insoluble in water. Its density is less than that of water, therefore, when oil gets into it, it spreads over the surface, preventing the dissolution of oxygen and other air gases in the water. It is obvious that, when oil enters natural bodies of water, it causes the death of microorganisms and animals, leading to environmental disasters and even catastrophes. There are bacteria that can use oil components as food, converting it into harmless products of their vital activity. It is clear that the use of cultures of these bacteria is the most environmentally safe and promising way to combat environmental pollution with oil during its production, transportation and refining.

In nature, oil and associated petroleum gas, which will be discussed below, fill the cavities of the earth's interior. Being a mixture of various substances, oil does not have a constant boiling point. It is clear that each of its components retains its individual physical properties in the mixture, which makes it possible to separate the oil into its components. To do this, it is purified from mechanical impurities and sulfur-containing compounds and subjected to so-called fractional distillation, or rectification.

Fractional distillation is a physical method of separating a mixture of components with different boiling points.

Distillation is carried out in special installations - distillation columns, in which cycles of condensation and evaporation of liquid substances contained in oil are repeated (Fig. 9).

The vapors formed when a mixture of substances boils are enriched with a lower boiling component (i.e., having a lower temperature). These vapors are collected, condensed (cooled to below boiling point) and brought back to a boil. In this case, vapors are formed that are even more enriched with a low-boiling substance. By repeating these cycles many times, it is possible to achieve almost complete separation of the substances contained in the mixture.

The distillation column receives oil heated in a tube furnace to a temperature of 320-350 °C. The distillation column has horizontal partitions with holes - the so-called trays, on which condensation of oil fractions occurs. Low-boiling fractions accumulate on the higher ones, and high-boiling ones - on the lower ones.

During the rectification process, oil is divided into the following fractions:

Rectifying gases are a mixture of low molecular weight hydrocarbons, mainly propane and butane, with a boiling point of up to 40 ° C;

Gasoline fraction (gasoline) - hydrocarbons of composition from C 5 H 12 to C 11 H 24 (boiling point 40-200 ° C); with a finer separation of this fraction, gasoline (petroleum ether, 40-70 °C) and gasoline (70-120 °C) are obtained;

Naphtha fraction - hydrocarbons of composition from C8H18 to C14H30 (boiling point 150-250 °C);

Kerosene fraction - hydrocarbons of composition from C12H26 to C18H38 (boiling point 180-300 °C);

Diesel fuel - hydrocarbons of composition from C13H28 to C19H36 (boiling point 200-350 ° C).

The remainder of oil distillation is fuel oil- contains hydrocarbons with the number of carbon atoms from 18 to 50. By distillation under reduced pressure from fuel oil, diesel oil (C18H28-C25H52), lubricating oils (C28H58-C38H78), petroleum jelly and paraffin are obtained - low-melting mixtures of solid hydrocarbons. The solid residue from the distillation of fuel oil - tar and the products of its processing - bitumen and asphalt are used for the manufacture of road surfaces.

The products obtained as a result of oil rectification are subjected to chemical processing, which includes a number of complex processes. One of them is cracking of petroleum products. You already know that fuel oil is separated into components under reduced pressure. This is explained by the fact that at atmospheric pressure its components begin to decompose before reaching the boiling point. This is precisely the basis of cracking.

Cracking - thermal decomposition of petroleum products, leading to the formation of hydrocarbons with a smaller number of carbon atoms in the molecule.

There are several types of cracking: thermal, catalytic cracking, high-pressure cracking, and reduction cracking.

Thermal cracking involves the splitting of hydrocarbon molecules with a long carbon chain into shorter ones under the influence of high temperature (470-550 ° C). During this cleavage, alkenes are formed along with alkanes.

In general, this reaction can be written as follows:

C n H 2n+2 -> C n-k H 2(n-k)+2 + C k H 2k
alkane alkane alkene
with long chain

The resulting hydrocarbons can be cracked again to form alkanes and alkenes with an even shorter chain of carbon atoms in the molecule:

Conventional thermal cracking produces a lot of low molecular weight gaseous hydrocarbons, which can be used as raw materials for the production of alcohols, carboxylic acids, and high molecular weight compounds (for example, polyethylene).

Catalytic cracking occurs in the presence of catalysts, which use natural aluminosilicates of the composition RA1203" T8Iu2-

Cracking with the use of catalysts leads to the formation of hydrocarbons having a branched or closed chain of carbon atoms in the molecule. The content of hydrocarbons of this structure in motor fuel significantly increases its quality, primarily the resistance to detonation - the octane number of gasoline.

Cracking of petroleum products occurs at high temperatures, so carbon deposits (soot) often form, contaminating the surface of the catalyst, which sharply reduces its activity.

Cleaning the surface of the catalyst from carbon deposits - its regeneration - is the main condition for the practical implementation of catalytic cracking. The simplest and cheapest way to regenerate a catalyst is to roast it, during which carbon deposits are oxidized with atmospheric oxygen. Gaseous oxidation products (mainly carbon dioxide and sulfur dioxide) are removed from the surface of the catalyst.

Catalytic cracking is a heterogeneous process in which solid (catalyst) and gaseous (hydrocarbon vapor) substances participate. It is obvious that catalyst regeneration - the interaction of solid soot with atmospheric oxygen - is also a heterogeneous process.

Heterogeneous reactions(gas - solid) flow faster as the surface area of the solid increases. Therefore, the catalyst is crushed, and its regeneration and cracking of hydrocarbons is carried out in a “fluidized bed”, familiar to you from the production of sulfuric acid.

The cracking feedstock, such as gas oil, enters a conical reactor. The lower part of the reactor has a smaller diameter, so the flow rate of raw material vapor is very high. The gas moving at high speed captures catalyst particles and carries them to the upper part of the reactor, where due to an increase in its diameter, the flow rate decreases. Under the influence of gravity, catalyst particles fall into the lower, narrower part of the reactor, from where they are carried upward again. Thus, each grain of catalyst is in constant motion and is washed from all sides by a gaseous reagent.

Some catalyst grains enter the outer, wider part of the reactor and, not encountering resistance to the gas flow, fall to the lower part, where they are picked up by the gas flow and carried into the regenerator. There, in the “fluidized bed” mode, the catalyst is fired and returned to the reactor.

Thus, the catalyst circulates between the reactor and the regenerator, and gaseous products of cracking and roasting are removed from them.

The use of cracking catalysts makes it possible to slightly increase the reaction rate, reduce its temperature, and improve the quality of cracking products.

The resulting hydrocarbons of the gasoline fraction mainly have a linear structure, which leads to low detonation resistance of the resulting gasoline.

We will consider the concept of “knock resistance” later, for now we will only note that hydrocarbons with molecules of a branched structure have significantly greater detonation resistance. It is possible to increase the proportion of isomeric branched hydrocarbons in the mixture formed during cracking by adding isomerization catalysts to the system.

Oil fields contain, as a rule, large accumulations of so-called associated petroleum gas, which collects above the oil in the earth's crust and is partially dissolved in it under the pressure of the overlying rocks. Like oil, associated petroleum gas is a valuable natural source of hydrocarbons. It contains mainly alkanes, whose molecules contain from 1 to 6 carbon atoms. It is obvious that the composition of associated petroleum gas is much poorer than oil. However, despite this, it is also widely used both as a fuel and as a raw material for the chemical industry. Just a few decades ago, in most oil fields, associated petroleum gas was burned as a useless supplement to oil. Currently, for example, in Surgut, the richest oil reserve in Russia, the cheapest electricity in the world is generated using associated petroleum gas as fuel.

As already noted, associated petroleum gas, compared to natural gas, is richer in composition in various hydrocarbons. Dividing them into fractions, we get:

Gas gasoline is a highly volatile mixture consisting mainly of lenthane and hexane;

A propane-butane mixture, consisting, as the name implies, of propane and butane and easily turning into a liquid state when the pressure increases;

Dry gas is a mixture containing mainly methane and ethane.

Gasoline, being a mixture of volatile components with a small molecular weight, evaporates well even at low temperatures. This makes it possible to use gas gasoline as fuel for internal combustion engines in the Far North and as an additive to motor fuel, making it easier to start engines in winter conditions.

A propane-butane mixture in the form of liquefied gas is used as household fuel (the familiar gas cylinders at your dacha) and for filling lighters. The gradual transition of road transport to liquefied gas is one of the main ways to overcome the global fuel crisis and solve environmental problems.

Dry gas, close in composition to natural gas, is also widely used as fuel.

However, the use of associated petroleum gas and its components as fuel is far from the most promising way to use it.

It is much more efficient to use the components of associated petroleum gas as raw materials for chemical production. From the alkanes that make up associated petroleum gas, hydrogen, acetylene, unsaturated and aromatic hydrocarbons and their derivatives are obtained.

Gaseous hydrocarbons can not only accompany oil in the earth's crust, but also form independent accumulations - natural gas deposits.

Natural gas - a mixture of gaseous saturated hydrocarbons with a low molecular weight. The main component of natural gas is methane, the share of which, depending on the field, ranges from 75 to 99% by volume. In addition to methane, natural gas includes ethane, propane, butane and isobutane, as well as nitrogen and carbon dioxide.

Like associated petroleum, natural gas is used both as a fuel and as a raw material for the production of a variety of organic and inorganic substances. You already know that hydrogen, acetylene and methyl alcohol, formaldehyde and formic acid, and many other organic substances are obtained from methane, the main component of natural gas. Natural gas is used as fuel in power plants, in boiler systems for water heating of residential and industrial buildings, in blast furnace and open-hearth industries. By striking a match and lighting the gas in the kitchen gas stove of a city house, you “trigger” a chain reaction of oxidation of alkanes that make up natural gas. In addition to oil, natural and associated petroleum gases, coal is a natural source of hydrocarbons. 0n forms thick layers in the bowels of the earth, its proven reserves significantly exceed oil reserves. Like oil, coal contains a large amount of various organic substances. In addition to organic substances, it also contains inorganic substances, such as water, ammonia, hydrogen sulfide and, of course, carbon itself - coal. One of the main methods of processing coal is coking - calcination without air access. As a result of coking, which is carried out at a temperature of about 1000 °C, the following are formed:

Coke oven gas, which contains hydrogen, methane, carbon dioxide and carbon dioxide, admixtures of ammonia, nitrogen and other gases;
coal tar containing several hundred times-personal organic substances, including benzene and its homologues, phenol and aromatic alcohols, naphthalene and various heterocyclic compounds;
suprasin, or ammonia water, containing, as the name implies, dissolved ammonia, as well as phenol, hydrogen sulfide and other substances;
coke is a solid residue from coking, almost pure carbon.

Coke is used in the production of iron and steel, ammonia - in the production of nitrogen and combined fertilizers, and the importance of organic coking products can hardly be overestimated.

Thus, associated petroleum and natural gases, coal are not only the most valuable sources of hydrocarbons, but also part of a unique storehouse of irreplaceable natural resources, the careful and reasonable use of which is a necessary condition for the progressive development of human society.

1. List the main natural sources of hydrocarbons. What organic substances are included in each of them? What do their compositions have in common?

2. Describe the physical properties of oil. Why doesn't it have a constant boiling point?

3. Summarizing media reports, describe the environmental disasters caused by oil leaks and ways to overcome their consequences.

4. What is rectification? What is this process based on? Name the fractions obtained as a result of oil rectification. How are they different from each other?

5. What is cracking? Give equations for three reactions corresponding to the cracking of petroleum products.

6. What types of cracking do you know? What do these processes have in common? How are they different from each other? What is the fundamental difference between different types of cracking products?

7. Why does associated petroleum gas have this name? What are its main components and their uses?

8. How does natural gas differ from associated petroleum gas? What do their compositions have in common? Give the combustion reaction equations for all components of associated petroleum gas known to you.

9. Give reaction equations that can be used to obtain benzene from natural gas. Specify the conditions for these reactions.

10. What is coking? What are its products and their composition? Give equations of reactions characteristic of the products of coking coal known to you.

11. Explain why burning oil, coal and associated petroleum gas is far from the most rational way to use them.

The most important sources of hydrocarbons are natural and associated petroleum gases, oil, and coal.

By reserves natural gas The first place in the world belongs to our country. Natural gas contains hydrocarbons with low molecular weight. It has the following approximate composition (by volume): 80–98% methane, 2–3% of its closest homologues - ethane, propane, butane and a small amount of impurities - hydrogen sulfide H 2 S, nitrogen N 2, noble gases, carbon monoxide (IV ) CO 2 and water vapor H 2 O . The composition of gas is specific to each field. There is the following pattern: the higher the relative molecular weight of the hydrocarbon, the less it is contained in natural gas.

Natural gas is widely used as a cheap fuel with a high calorific value (up to 54,400 kJ is released when 1 m 3 is burned). This is one of the best types of fuel for domestic and industrial needs. In addition, natural gas serves as a valuable raw material for the chemical industry: the production of acetylene, ethylene, hydrogen, soot, various plastics, acetic acid, dyes, medicines and other products.

Associated petroleum gases are in deposits together with oil: they are dissolved in it and are located above the oil, forming a gas “cap”. When oil is extracted to the surface, gases are separated from it due to a sharp drop in pressure. Previously, associated gases were not used and were flared during oil production. Currently, they are captured and used as fuel and valuable chemical raw materials. Associated gases contain less methane than natural gas, but more ethane, propane, butane and higher hydrocarbons. In addition, they contain basically the same impurities as in natural gas: H 2 S, N 2, noble gases, H 2 O vapors, CO 2 . Individual hydrocarbons (ethane, propane, butane, etc.) are extracted from associated gases; their processing makes it possible to obtain unsaturated hydrocarbons by dehydrogenation - propylene, butylene, butadiene, from which rubbers and plastics are then synthesized. A mixture of propane and butane (liquefied gas) is used as household fuel. Gas gasoline (a mixture of pentane and hexane) is used as an additive to gasoline for better ignition of the fuel when starting the engine. The oxidation of hydrocarbons produces organic acids, alcohols and other products.

Oil– an oily, flammable liquid of dark brown or almost black color with a characteristic odor. It is lighter than water (= 0.73–0.97 g/cm3) and is practically insoluble in water. In terms of composition, oil is a complex mixture of hydrocarbons of different molecular weights, so it does not have a specific boiling point.

Oil consists mainly of liquid hydrocarbons (solid and gaseous hydrocarbons are dissolved in them). Typically these are alkanes (mostly of normal structure), cycloalkanes and arenes, the ratio of which in oils from different fields varies widely. Ural oil contains more arenes. In addition to hydrocarbons, oil contains oxygen, sulfur and nitrogenous organic compounds.

Crude oil is not usually used. To obtain technically valuable products from oil, it is subjected to processing.

Primary processing oil consists of its distillation. Distillation is carried out at oil refineries after separation of associated gases. When distilling oil, light petroleum products are obtained:

gasoline ( t boil = 40–200 °C) contains hydrocarbons C 5 – C 11,

naphtha ( t boil = 150–250 °C) contains hydrocarbons C 8 – C 14,

kerosene ( t boil = 180–300 °C) contains hydrocarbons C 12 – C 18,

gas oil ( t kip > 275 °C),

and the remainder is a viscous black liquid - fuel oil.

The fuel oil is subjected to further processing. It is distilled under reduced pressure (to prevent decomposition) and lubricating oils are isolated: spindle, machine, cylinder, etc. Vaseline and paraffin are isolated from fuel oil of some types of oil. The remainder of the fuel oil after distillation - tar - after partial oxidation is used to produce asphalt. The main disadvantage of oil distillation is the low yield of gasoline (no more than 20%).

Petroleum distillation products have various uses.

Petrol It is used in large quantities as aviation and automobile fuel. It usually consists of hydrocarbons containing an average of 5 to 9 C atoms in their molecules. Naphtha It is used as fuel for tractors, and also as a solvent in the paint and varnish industry. Large quantities of it are processed into gasoline. Kerosene It is used as fuel for tractors, jet aircraft and rockets, as well as for domestic needs. Solar oil – gas oil– used as motor fuel, and lubricating oils– for lubrication of mechanisms. Petrolatum used in medicine. It consists of a mixture of liquid and solid hydrocarbons. Paraffin used for the production of higher carboxylic acids, for impregnating wood in the production of matches and pencils, for making candles, shoe polish, etc. It consists of a mixture of solid hydrocarbons. Fuel oil In addition to processing into lubricating oils and gasoline, it is used as boiler liquid fuel.

At secondary processing methods oil, the structure of the hydrocarbons included in its composition changes. Among these methods, cracking of petroleum hydrocarbons is of great importance, carried out in order to increase the yield of gasoline (up to 65–70%).

Cracking– the process of splitting hydrocarbons contained in oil, which results in the formation of hydrocarbons with a smaller number of C atoms in the molecule. There are two main types of cracking: thermal and catalytic.

Thermal cracking is carried out by heating the feedstock (fuel oil, etc.) at a temperature of 470–550 °C and a pressure of 2–6 MPa. In this case, hydrocarbon molecules with a large number of C atoms are split into molecules with a smaller number of atoms of both saturated and unsaturated hydrocarbons. For example:

(radical mechanism),

This method is used to produce mainly motor gasoline. Its yield from oil reaches 70%. Thermal cracking was discovered by Russian engineer V.G. Shukhov in 1891.

Catalytic cracking carried out in the presence of catalysts (usually aluminosilicates) at 450–500 °C and atmospheric pressure. This method produces aviation gasoline with a yield of up to 80%. This type of cracking mainly affects kerosene and gas oil fractions of oil. During catalytic cracking, along with splitting reactions, isomerization reactions occur. As a result of the latter, saturated hydrocarbons with a branched carbon skeleton of molecules are formed, which improves the quality of gasoline:

Catalytic cracking gasoline has a higher quality. The process of obtaining it proceeds much faster, with less thermal energy consumption. In addition, catalytic cracking produces relatively many branched-chain hydrocarbons (isocompounds), which are of great value for organic synthesis.

At t= 700 °C and above pyrolysis occurs.

Pyrolysis– decomposition of organic substances without air access at high temperatures. In the pyrolysis of oil, the main reaction products are unsaturated gaseous hydrocarbons (ethylene, acetylene) and aromatic hydrocarbons - benzene, toluene, etc. Since oil pyrolysis is one of the most important ways to obtain aromatic hydrocarbons, this process is often called oil aromatization.

Aromatization– transformation of alkanes and cycloalkanes into arenes. When heavy fractions of petroleum products are heated in the presence of a catalyst (Pt or Mo), hydrocarbons containing 6–8 C atoms per molecule are converted into aromatic hydrocarbons. These processes occur during reforming (gasoline upgrading).

Reforming- This is the aromatization of gasoline, carried out as a result of heating them in the presence of a catalyst, for example Pt. Under these conditions, alkanes and cycloalkanes are converted into aromatic hydrocarbons, as a result of which the octane number of gasoline also increases significantly. Aromatization is used to obtain individual aromatic hydrocarbons (benzene, toluene) from gasoline fractions of oil.

In recent years, petroleum hydrocarbons have been widely used as a source of chemical raw materials. In various ways, substances necessary for the production of plastics, synthetic textile fibers, synthetic rubber, alcohols, acids, synthetic detergents, explosives, pesticides, synthetic fats, etc. are obtained from them.

Coal Just like natural gas and oil, it is a source of energy and valuable chemical raw materials.

The main method of processing coal is coking(dry distillation). When coking (heating to 1000 °C - 1200 °C without air access), various products are obtained: coke, coal tar, tar water and coke oven gas (diagram).

Scheme

Coke is used as a reducing agent in the production of cast iron in metallurgical plants.

Coal tar serves as a source of aromatic hydrocarbons. It is subjected to rectification distillation and benzene, toluene, xylene, naphthalene, as well as phenols, nitrogen-containing compounds, etc. are obtained. Pitch is a thick black mass remaining after distillation of the resin, used for the preparation of electrodes and roofing felt.

Ammonia, ammonium sulfate, phenol, etc. are obtained from tar water.

Coke oven gas is used to heat coke ovens (about 18,000 kJ are released when 1 m 3 is burned), but it is mainly subjected to chemical processing. Thus, hydrogen is isolated from it for the synthesis of ammonia, which is then used to produce nitrogen fertilizers, as well as methane, benzene, toluene, ammonium sulfate, and ethylene.

The main natural sources of hydrocarbons are oil, gas, and coal. Most of the substances of organic chemistry are isolated from them. We will discuss this class of organic substances in more detail below.

Composition of minerals

Hydrocarbons are the most extensive class of organic substances. These include acyclic (linear) and cyclic classes of compounds. There are saturated (saturated) and unsaturated (unsaturated) hydrocarbons.

Saturated hydrocarbons include compounds with single bonds:

alkanes- linear connections;
cycloalkanes- cyclic substances.

Unsaturated hydrocarbons include substances with multiple bonds:

alkenes- contain one double bond;
alkynes- contain one triple bond;
alkadienes- include two double bonds.

There is a separate class of arenes or aromatic hydrocarbons containing a benzene ring.

Rice. 1. Classification of hydrocarbons.

Mineral resources include gaseous and liquid hydrocarbons. The table describes natural sources of hydrocarbons in more detail.

*Source*	*Kinds*
		Alkanes, cycloalkanes, arenes, oxygen, nitrogen, sulfur-containing compounds
	natural - a mixture of gases found in nature; associated - a gaseous mixture dissolved in oil or located above it	Methane with impurities (no more than 5%): propane, butane, carbon dioxide, nitrogen, hydrogen sulfide, water vapor. Natural gas contains more methane than associated gas
	anthracite - includes 95% carbon; stone - contains 99% carbon; brown - 72% carbon	Carbon, hydrogen, sulfur, nitrogen, oxygen, hydrocarbons

Every year more than 600 billion m 3 of gas, 500 million tons of oil, and 300 million tons of coal are produced in Russia.

Recycling

Minerals are used in processed form. Coal is calcined without oxygen (coking process) to separate several fractions:

coke oven gas- a mixture of methane, carbon oxides (II) and (IV), ammonia, nitrogen;
coal tar- a mixture of benzene, its homologues, phenol, arenes, heterocyclic compounds;
ammonia water- a mixture of ammonia, phenol, hydrogen sulfide;
coke- the final coking product containing pure carbon.

Rice. 2. Coking.

One of the leading branches of world industry is oil refining. Oil extracted from the depths of the earth is called crude oil. It is recycled. First, mechanical purification from impurities is carried out, then the purified oil is distilled to obtain various fractions. The table describes the main fractions of oil.

*Fraction*	*Compound*	*What do you get?*
	Gaseous alkanes from methane to butane
Gasoline	Alkanes from pentane (C 5 H 12) to undecane (C 11 H 24)	Gasoline, esters
Naphtha	Alkanes from octane (C 8 H 18) to tetradecane (C 14 H 30)	Naphtha (heavy gasoline)
Kerosene
Diesel	Alkanes from tridecane (C 13 H 28) to nonadecane (C 19 H 36)
	Alkanes from pentadecane (C 15 H 32) to pentacontane (C 50 H 102)	Lubricating oils, petroleum jelly, bitumen, paraffin, tar

Rice. 3. Oil distillation.

Plastics, fibers, and medicines are produced from hydrocarbons. Methane and propane are used as household fuel. Coke is used in the production of iron and steel. Nitric acid, ammonia, and fertilizers are produced from ammonia water. Tar is used in construction.

What have we learned?

From the topic of the lesson we learned from what natural sources hydrocarbons are isolated. Oil, coal, natural and associated gases are used as raw materials for organic compounds. Minerals are purified and divided into fractions, from which substances suitable for production or direct use are obtained. Liquid fuels and oils are produced from oil. The gases contain methane, propane, butane, used as household fuel. Liquid and solid raw materials are extracted from coal for the production of alloys, fertilizers, and medicines.

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NATURAL SOURCES OF HYDROCARBONS

Hydrocarbons are all so different -
Liquid and solid and gaseous.
Why are there so many of them in nature?
It's about insatiable carbon.

Indeed, this element, like no other, is “insatiable”: it strives to form chains, straight and branched, rings, or networks from its many atoms. Hence there are many compounds of carbon and hydrogen atoms.

Hydrocarbons are both natural gas - methane, and another household flammable gas that is used to fill cylinders - propane C 3 H 8. Hydrocarbons include oil, gasoline, and kerosene. And also - organic solvent C 6 H 6, paraffin from which New Year's candles are made, Vaseline from the pharmacy and even a plastic bag for packaging products...

The most important natural sources of hydrocarbons are minerals - coal, oil, gas.

COAL

More is known on the globe 36 thousand coal basins and deposits, which together occupy 15% territories of the globe. Coal basins can stretch for thousands of kilometers. The total geological reserves of coal on the globe are 5 trillion 500 billion tons, including explored deposits - 1 trillion 750 billion tons.

There are three main types of fossil coals. When brown coal and anthracite burn, the flame is invisible, the combustion is smokeless, and when burning coal makes a loud crackling sound.

Anthracite- the oldest of fossil coals. It is distinguished by high density and shine. Contains up to 95% carbon.

Coal– contains up to 99% carbon. Of all fossil coals, it has the widest application.

Brown coal– contains up to 72% carbon. Has a brown color. As the youngest of fossil coals, it often retains traces of the structure of the wood from which it was formed. It is characterized by high hygroscopicity and high ash content ( from 7% to 38%), therefore, it is used only as local fuel and as raw material for chemical processing. In particular, by hydrogenation, valuable types of liquid fuel are obtained: gasoline and kerosene.

Carbon is the main component of coal ( 99% ), brown coal ( up to 72%).

The origin of the name carbon, that is, “giving birth to coal.” Similarly, the Latin name “carboneum” contains the root carbo-charcoal at its base.

Like oil, coal contains large amounts of organic matter. In addition to organic substances, it also contains inorganic substances, such as water, ammonia, hydrogen sulfide and, of course, carbon itself - coal. One of the main methods of processing coal is coking - calcination without air access. As a result of coking, which is carried out at a temperature of 1000 0 C, the following is formed:– it contains hydrogen, methane, carbon dioxide and carbon dioxide, admixtures of ammonia, nitrogen and other gases.

Coal tar – contains several hundred different organic substances, including benzene and its homologues, phenol and aromatic alcohols, naphthalene and various heterocyclic compounds.

Resin or ammonia water – containing, as the name implies, dissolved ammonia, as well as phenol, hydrogen sulfide and other substances.

Coke– solid coking residue, practically pure carbon.

Coke is used in the production of iron and steel, ammonia is used in the production of nitrogen and combined fertilizers, and the importance of organic coking products can hardly be overestimated. What is the geography of distribution of this mineral?

The bulk of coal resources are located in the northern hemisphere - Asia, North America, Eurasia. Which countries stand out in terms of coal reserves and production?

China, USA, India, Australia, Russia.

The main exporters of coal are countries.

USA, Australia, Russia, South Africa.

Main import centers.

Japan, Foreign Europe.

This is a very environmentally polluting fuel. When mining coal, explosions and methane fires occur, and certain environmental problems arise.

Environmental pollution is any undesirable change in the state of this environment as a result of human economic activity. This also happens during mining. Let's imagine the situation in a coal mining area. Together with the coal, a huge amount of waste rock rises to the surface, which is simply sent to dumps as unnecessary. Gradually formed waste heaps- huge, tens of meters high, cone-shaped mountains of waste rock that distort the appearance of the natural landscape. Will all the coal raised to the surface be transported to the consumer? Of course not. After all, the process is not airtight. A huge amount of coal dust settles on the surface of the earth. As a result, the composition of soils and groundwater changes, which will inevitably affect the flora and fauna of the area.

Coal contains radioactive carbon - C, but after burning the fuel, the dangerous substance, along with the smoke, enters the air, water, soil, and is sintered into slag or ash, which is used for the production of building materials. As a result, walls and ceilings in residential buildings “sink” and pose a threat to human health.

OIL

Oil has been known to mankind since ancient times. It was mined on the banks of the Euphrates

6-7 thousand years BC uh . It was used for lighting homes, for preparing mortars, as medicines and ointments, and for embalming. Oil in the ancient world was a formidable weapon: rivers of fire poured onto the heads of those storming fortress walls, burning arrows dipped in oil flew into besieged cities. Oil was an integral part of the incendiary agent, which went down in history under the name "Greek fire" In the Middle Ages it was used mainly for street lighting.

More than 600 oil and gas basins have been explored, 450 are being developed , and the total number of oil fields reaches 50 thousand.

There are light and heavy oils. Light oil is extracted from the subsoil using pumps or the fountain method. This oil is mainly used to make gasoline and kerosene. Heavy grades of oil are sometimes even extracted using a mine method (in the Komi Republic), and bitumen, fuel oil, and various oils are prepared from it.

Oil is the most versatile fuel, high in calories. Its extraction is relatively simple and cheap, because when extracting oil there is no need to put people underground. Transporting oil through pipelines is not a big problem. The main disadvantage of this type of fuel is its low resource availability (about 50 years ) . General geological reserves are equal to 500 billion tons, including explored 140 billion tons .

IN 2007 year, Russian scientists proved to the world community that the underwater Lomonosov and Mendeleev ridges, which are located in the Arctic Ocean, are a continental shelf zone, and therefore belong to the Russian Federation. A chemistry teacher will tell you about the composition of oil and its properties.

Oil is a “clump of energy”. With just 1 ml of it, you can heat a whole bucket of water by one degree, and in order to boil a bucket samovar, you need less than half a glass of oil. In terms of energy concentration per unit volume, oil ranks first among natural substances. Even radioactive ores cannot compete with it in this regard, since the content of radioactive substances in them is so small that 1 mg can be extracted. Nuclear fuel requires processing tons of rocks.

Oil is not only the basis of the fuel and energy complex of any state.

The famous words of D.I. Mendeleev are in place here “burning oil is the same as lighting a furnace banknotes". Each drop of oil contains more than 900 various chemical compounds, more than half of the chemical elements of the Periodic Table. This is truly a miracle of nature, the basis of the petrochemical industry. Approximately 90% of all oil produced is used as fuel. Despite “ your 10%” , petrochemical synthesis provides the production of many thousands of organic compounds that satisfy the urgent needs of modern society. It is not for nothing that people respectfully call oil “black gold”, “the blood of the Earth”.

Oil is an oily dark brown liquid with a reddish or greenish tint, sometimes black, red, blue or light and even transparent with a characteristic pungent odor. There is oil that is white or colorless, like water (for example, in the Surukhan field in Azerbaijan, in some fields in Algeria).

The composition of oil is not the same. But all of them usually contain three types of hydrocarbons - alkanes (mostly of normal structure), cycloalkanes and aromatic hydrocarbons. The ratio of these hydrocarbons in oil from different fields is different: for example, Mangyshlak oil is rich in alkanes, and oil in the Baku region is rich in cycloalkanes.

The main oil reserves are located in the northern hemisphere. Total 75 Countries in the world produce oil, but 90% of its production comes from just 10 countries. Near ? The world's oil reserves are in developing countries. (The teacher names and shows on the map).

Main producing countries:

Saudi Arabia, USA, Russia, Iran, Mexico.

At the same time more 4/5 Oil consumption accounts for the share of economically developed countries, which are the main importing countries:

Japan, Foreign Europe, USA.

Crude oil is not used anywhere, but refined petroleum products are used.

Oil refining

A modern installation consists of a furnace for heating oil and a distillation column, where the oil is separated into factions – separate mixtures of hydrocarbons in accordance with their boiling points: gasoline, naphtha, kerosene. The furnace has a long pipe rolled into a coil. The furnace is heated by combustion products of fuel oil or gas. Oil is continuously fed into the coil: there it is heated to 320 - 350 0 C in the form of a mixture of liquid and vapor and enters the distillation column. The distillation column is a steel cylindrical apparatus about 40 m high. It has several dozen horizontal partitions with holes inside - the so-called plates. Oil vapor entering the column rises up and passes through holes in the plates. Gradually cooling as they move upward, they partially liquefy. Less volatile hydrocarbons are liquefied already on the first plates, forming a gas oil fraction; more volatile hydrocarbons collect higher and form the kerosene fraction; even higher – naphtha fraction. The most volatile hydrocarbons exit the column as vapors and, after condensation, form gasoline. Part of the gasoline is fed back into the column for “irrigation,” which contributes to better operating conditions. (Write in notebook). Gasoline – contains hydrocarbons C5 – C11, boiling in the range from 40 0 C to 200 0 C; naphtha – contains C8 - C14 hydrocarbons with a boiling point from 120 0 C to 240 0 C; kerosene - contains C12 – C18 hydrocarbons, boiling at a temperature from 180 0 C to 300 0 C; gas oil - contains C13 – C15 hydrocarbons, distilled at temperatures from 230 0 C to 360 0 C; lubricating oils - C16 - C28, boil at a temperature of 350 0 C and above.

After distilling light products from oil, a viscous black liquid remains - fuel oil. It is a valuable mixture of hydrocarbons. Lubricating oils are obtained from fuel oil through additional distillation. The non-distillable part of fuel oil is called tar, which is used in construction and for paving roads. (Demonstration of a video fragment). The most valuable fraction of direct distillation of oil is gasoline. However, the yield of this fraction does not exceed 17-20% by weight of crude oil. A problem arises: how to satisfy the ever-increasing needs of society for automobile and aviation fuel? The solution was found at the end of the 19th century by a Russian engineer Vladimir Grigorievich Shukhov. IN 1891 year he first carried out an industrial cracking kerosene fraction of oil, which made it possible to increase the yield of gasoline to 65-70% (based on crude oil). Only for the development of the process of thermal cracking of petroleum products, grateful humanity inscribed the name of this unique person in the history of civilization in golden letters.

The products obtained as a result of oil rectification are subjected to chemical processing, which includes a number of complex processes. One of them is cracking of petroleum products (from the English “Cracking” - splitting). There are several types of cracking: thermal, catalytic, high-pressure cracking, and reduction cracking. Thermal cracking consists of splitting long-chain hydrocarbon molecules into shorter ones under the influence of high temperature (470-550 0 C). During this cleavage, alkenes are formed along with alkanes:

Currently, catalytic cracking is the most common. It is carried out at a temperature of 450-500 0 C, but at a higher speed and makes it possible to obtain higher quality gasoline. Under catalytic cracking conditions, along with splitting reactions, isomerization reactions occur, that is, the conversion of hydrocarbons of normal structure into branched hydrocarbons.

Isomerization affects the quality of gasoline, since the presence of branched hydrocarbons greatly increases its octane number. Cracking is classified as a so-called secondary oil refining process. A number of other catalytic processes, such as reforming, are also classified as secondary. Reforming- This is the aromatization of gasoline by heating it in the presence of a catalyst, for example, platinum. Under these conditions, alkanes and cycloalkanes are converted into aromatic hydrocarbons, as a result of which the octane number of gasoline also increases significantly.

Ecology and oil field

For petrochemical production, the environmental problem is especially pressing. Oil production involves energy costs and environmental pollution. A dangerous source of pollution of the World Ocean is offshore oil production, and the World Ocean is also polluted during oil transportation. Each of us has seen on television the consequences of oil tanker accidents. Black shores covered with a layer of fuel oil, black surf, gasping dolphins, Birds whose wings are covered in viscous fuel oil, people in protective suits collecting oil with shovels and buckets. I would like to provide data on a serious environmental disaster that occurred in the Kerch Strait in November 2007. 2 thousand tons of petroleum products and about 7 thousand tons of sulfur got into the water. The most affected by the disaster were the Tuzla spit, which is located at the junction of the Black and Azov seas, and the Chushka spit. After the accident, the fuel oil settled to the bottom, causing the death of the small heart-shaped shell, the main food of the sea inhabitants. It will take 10 years to restore the ecosystem. More than 15 thousand birds died. A liter of oil, once in the water, spreads over its surface in spots with an area of 100 sq.m. The oil film, although very thin, forms an insurmountable barrier to the path of oxygen from the atmosphere to the water column. As a result, the oxygen regime and the ocean are disrupted “suffocates.” Plankton, which is the basis of the ocean food chain, is dying. Currently, about 20% of the area of the World Ocean is already covered with oil spills, and the area affected by oil pollution is growing. In addition to the fact that the World Ocean is covered with an oil film, we can also observe it on land. For example, in the oil fields of Western Siberia more oil is spilled per year than a tanker can hold - up to 20 million tons. About half of this oil ends up on the ground as a result of accidents, the rest is “planned” gushers and leaks during the startup of wells, exploratory drilling, and pipeline repairs. The largest area of oil-contaminated land, according to the Environmental Committee of the Yamalo-Nenets Autonomous Okrug, is in the Purovsky district.

NATURAL AND ASSOCIATED PETROLEUM GAS

Natural gas contains hydrocarbons with low molecular weight, the main components being methane.

In terms of its properties, natural gas as a fuel is superior even to oil; it is more caloric. This is the youngest branch of the fuel industry. Gas is even easier to extract and transport. This is the most economical of all types of fuel. There are, however, some disadvantages: complicated intercontinental gas transportation. Methane tankers transporting gas in a liquefied state are extremely complex and expensive structures.

Used as: effective fuel, raw materials in the chemical industry, in the production of acetylene, ethylene, hydrogen, soot, plastics, acetic acid, dyes, medicines, etc. Associated (petroleum gases) are natural gases that dissolve in oil and are released during its mining

Petroleum gas contains less methane, but more propane, butane and other higher hydrocarbons. Where is the gas produced?

More than 70 countries around the world have industrial gas reserves. Moreover, as in the case of oil, developing countries have very large reserves. But gas production is carried out mainly by developed countries. They have the ability to use it or a way to sell gas to other countries on the same continent. International gas trade is less active than oil trade. About 15% of the world's gas is supplied to the international market. Almost 2/3 of world gas production comes from Russia and the USA. Undoubtedly, the leading gas production region not only in our country, but also in the world is the Yamalo-Nenets Autonomous Okrug, where this industry has been developing for 30 years. Our city of Novy Urengoy is rightfully recognized as the gas capital. The largest deposits include Urengoyskoye, Yamburgskoye, Medvezhye, Zapolyarnoye. The Urengoy deposit is included in the Guinness Book of Records. The deposit's reserves and production are unique. Explored reserves exceed 10 trillion. m 3, since operation, 6 trillion have already been produced. m 3. In 2008, OJSC Gazprom plans to extract 598 billion m 3 of “blue gold” from the Urengoy deposit.

Gas and ecology

Oil, gas, coal are valuable raw materials for the chemical industry. In the near future, a replacement will be found for them in the fuel and energy complex of our country. Currently, scientists are searching for ways to use solar and wind energy and nuclear fuel to completely replace oil. The most promising type of fuel of the future is hydrogen. Reducing the use of oil in thermal power engineering is the path not only to its more rational use, but also to the preservation of this raw material for future generations. Hydrocarbon raw materials should be used only in the processing industry to obtain a variety of products. Unfortunately, the situation has not yet changed, and up to 94% of produced oil serves as fuel. D.I. Mendeleev wisely said: “Burning oil is the same as heating a furnace with banknotes.”