Natural source of hydrocarbons	Its main features
Oil	Multi-component mixture consisting mainly of hydrocarbons. Hydrocarbons are mainly represented by alkanes, cycloalkanes and arenes.
Associated petroleum gas	A mixture consisting almost exclusively of alkanes with a long carbon chain from 1 to 6 carbon atoms, is formed along with the extraction of oil, hence the origin of the name. There is a trend: the lower the molecular weight of the alkane, the higher its percentage in associated petroleum gas.
Natural gas	A mixture consisting predominantly of low molecular weight alkanes. The main component of natural gas is methane. Its percentage, depending on the gas field, can be from 75 to 99%. In second place in terms of concentration by a wide margin is ethane, propane is even less contained, etc. The fundamental difference between natural gas and associated petroleum gas is that the proportion of propane and isomeric butanes in associated petroleum gas is much higher.
Coal	Multicomponent mixture of various compounds of carbon, hydrogen, oxygen, nitrogen and sulfur. Also, the composition of coal includes a significant amount of inorganic substances, the proportion of which is significantly higher than in oil.

Oil refining

Oil is a multicomponent mixture of various substances, mainly hydrocarbons. These components differ from each other in boiling points. In this regard, if oil is heated, then the lightest-boiling components will first evaporate from it, then compounds with a higher boiling point, etc. Based on this phenomenon primary oil refining , consisting in distillation (rectification) oil. This process is called primary, since it is assumed that during its course chemical transformations of substances do not occur, and oil is only separated into fractions with different boiling points. Below is a schematic diagram of a distillation column with a brief description of the distillation process itself:

Before the rectification process, oil is prepared in a special way, namely, it is removed from impurity water with salts dissolved in it and from solid mechanical impurities. The oil prepared in this way enters the tubular furnace, where it is heated to a high temperature (320-350 o C). After being heated in a tubular furnace, high-temperature oil enters the lower part of the distillation column, where individual fractions evaporate and their vapors rise up the distillation column. The higher the section of the distillation column is, the lower its temperature. Thus, the following fractions are taken at different heights:

1) distillation gases (taken from the very top of the column, and therefore their boiling point does not exceed 40 ° C);

2) gasoline fraction (boiling point from 35 to 200 o C);

3) naphtha fraction (boiling points from 150 to 250 o C);

4) kerosene fraction (boiling points from 190 to 300 o C);

5) diesel fraction (boiling point from 200 to 300 o C);

6) fuel oil (boiling point over 350 o C).

It should be noted that the average fractions isolated during the rectification of oil do not meet the standards for fuel quality. In addition, as a result of oil distillation, a considerable amount of fuel oil is formed - far from being the most demanded product. In this regard, after the primary processing of oil, the task is to increase the yield of more expensive, in particular, gasoline fractions, as well as to improve the quality of these fractions. These tasks are solved using various processes. oil refining , such as cracking andreforming .

It should be noted that the number of processes used in the secondary processing of oil is much larger, and we touch on only some of the main ones. Let's now understand what is the meaning of these processes.

Cracking (thermal or catalytic)

This process is designed to increase the yield of the gasoline fraction. For this purpose, heavy fractions, such as fuel oil, are subjected to strong heating, most often in the presence of a catalyst. As a result of this action, long-chain molecules that are part of the heavy fractions are torn and hydrocarbons with a lower molecular weight are formed. In fact, this leads to an additional yield of a more valuable gasoline fraction than the original fuel oil. The chemical essence of this process is reflected by the equation:

Reforming

This process performs the task of improving the quality of the gasoline fraction, in particular, increasing its knock resistance (octane number). It is this characteristic of gasolines that is indicated at gas stations (92nd, 95th, 98th gasoline, etc.).

As a result of the reforming process, the proportion of aromatic hydrocarbons in the gasoline fraction increases, which among other hydrocarbons has one of the highest octane numbers. Such an increase in the proportion of aromatic hydrocarbons is achieved mainly as a result of the dehydrocyclization reactions occurring during the reforming process. For example, when heated sufficiently n-hexane in the presence of a platinum catalyst, it turns into benzene, and n-heptane in a similar way - into toluene:

Coal processing

The main method of coal processing is coking . Coal coking called the process in which coal is heated without access to air. At the same time, as a result of such heating, four main products are isolated from coal:

1) coke

A solid substance that is almost pure carbon.

2) Coal tar

Contains a large number of various predominantly aromatic compounds, such as benzene, its homologues, phenols, aromatic alcohols, naphthalene, naphthalene homologues, etc.;

3) Ammonia water

Despite its name, this fraction, in addition to ammonia and water, also contains phenol, hydrogen sulfide and some other compounds.

4) coke oven gas

The main components of coke oven gas are hydrogen, methane, carbon dioxide, nitrogen, ethylene, etc.

NATURAL SOURCES OF HYDROCARBONS

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

Indeed, this element, like no other, is “insatiable”: it strives to form chains, straight and branched, then rings, then grids from a multitude of its atoms. Hence the many compounds of carbon and hydrogen atoms.

Hydrocarbons are both natural gas - methane, and another household combustible gas, which is filled with cylinders - propane C 3 H 8. Hydrocarbons are oil, gasoline, and kerosene. And also - an organic solvent C 6 H 6, paraffin, from which New Year's candles are made, petroleum jelly from a pharmacy, and even a plastic bag for food packaging ...

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

COAL

More known around the world 36 thousand coal basins and deposits, which together occupy 15% territories of the globe. Coal fields can stretch for thousands of kilometers. In total, the general 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 burning brown coal, anthracite, the flame is invisible, the combustion is smokeless, and coal makes a loud crack when burning.

Anthraciteis the oldest fossil coal. Differs in the big density and gloss. Contains up to 95% carbon.

Coal- contains up to 99% carbon. Of all fossil coals, it is the most widely used.

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

Carbon is the main constituent of coal 99% ), brown coal ( up to 72%). The origin of the name carbon, i.e., “bearing coal”. Similarly, the Latin name "carboneum" at the base contains the root carbo-coal.

Like oil, coal contains a large amount of organic matter. In addition to organic substances, it also includes inorganic substances, such as water, ammonia, hydrogen sulfide and, of course, carbon itself - coal. One of the main ways of coal processing 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:

coke oven gas- it consists of hydrogen, methane, carbon monoxide and carbon dioxide, impurities 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.

Top-tar 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 cannot be overestimated. What is the geography of distribution of this mineral?

The main part of coal resources falls on the northern hemisphere - Asia, North America, Eurasia. What countries stand out in terms of reserves and coal production?

China, USA, India, Australia, Russia.

Countries are the main exporters of coal.

USA, Australia, Russia, South Africa.

main import centers.

Japan, Overseas Europe.

It is a very environmentally dirty fuel. Explosions and fires of methane occur during coal mining, and certain environmental problems arise.

Environmental pollution - this is any undesirable change in the state of this environment as a result of human activities. This also happens in mining. Imagine a situation in a coal mining area. Together with coal, a huge amount of waste rock rises to the surface, which, as unnecessary, is simply sent to dumps. Gradually formed waste heaps- huge, tens of meters high, cone-shaped mountains of waste rock, which distort the appearance of the natural landscape. And will all the coal raised to the surface be necessarily exported to the consumer? Of course not. After all, the process is not hermetic. 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 region.

Coal contains radioactive carbon - C, but after the fuel is burned, the hazardous substance, along with smoke, enters the air, water, soil, and is baked into slag or ash, which is used to produce building materials. As a result, in residential buildings, walls and ceilings “glow” and pose a threat to human health.

OIL

Oil has been known to mankind since ancient times. On the banks of the Euphrates, it was mined

6-7 thousand years BC uh . It was used to illuminate dwellings, to prepare mortars, as medicines and ointments, and for embalming. Oil in the ancient world was a formidable weapon: fiery rivers poured on the heads of those who stormed the fortress walls, burning arrows dipped in oil flew to the besieged cities. Oil was an integral part of the incendiary agent that went down in history under the name "Greek fire" In the Middle Ages, it was mainly used 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.

Distinguish between light and heavy oil. Light oil is extracted from the subsoil by pumps or by the fountain method. Mostly gasoline and kerosene are made from such oil. Heavy grades of oil are sometimes extracted even by the mine method (in the Komi Republic), and bitumen, fuel oil, and various oils are prepared from it.

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

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

Oil is a "bundle of energy". With only 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 1mg can be extracted. nuclear fuel must be processed tons of rocks.

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

Here, the famous words of D. I. Mendeleev are in place “burning oil is the same as heating 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. In spite of “ own 10%” , petrochemical synthesis provides many thousands of organic compounds that satisfy the urgent needs of modern society. No wonder 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. Sometimes oil is white or colorless, like water (for example, in the Surukhanskoye 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 (mainly normal structure), cycloalkanes and aromatic hydrocarbons. The ratio of these hydrocarbons in the oil of 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 in the northern hemisphere. Total 75 countries of the world produce oil, but 90% of its production falls on the share of only 10 countries. Near ? world oil reserves are in developing countries. (The teacher calls and shows on the map).

Main producing countries:

Saudi Arabia, USA, Russia, Iran, Mexico.

At the same time more 4/5 oil consumption falls on the share of economically developed countries, which are the main importing countries:

Japan, Overseas Europe, USA.

Oil in its raw form is not used anywhere, but refined products are used.

Oil refining

A modern plant consists of an oil heating furnace and a distillation column where the oil is separated into factions - individual mixtures of hydrocarbons according to their boiling points: gasoline, naphtha, kerosene. The furnace has a long tube coiled into a coil. The furnace is heated by the combustion products of fuel oil or gas. Oil is continuously supplied to 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 with a height of about 40m. It has inside several dozen horizontal partitions with holes - the so-called plates. Oil vapors, entering the column, rise up and pass through the holes in the plates. As they gradually cool as they move upwards, they partially liquefy. Less volatile hydrocarbons are liquefied already on the first plates, forming a gas oil fraction; more volatile hydrocarbons are collected above and form a kerosene fraction; even higher - naphtha fraction. The most volatile hydrocarbons leave the column as vapors and, after condensation, form gasoline. Part of the gasoline is fed back to the column for "irrigation", which contributes to a better mode of operation. (Entry in a notebook). Gasoline - contains hydrocarbons C5 - C11, boiling in the range from 40 0 ​​C to 200 0 C; naphtha - contains hydrocarbons C8 - C14 with a boiling point of 120 0 C to 240 0 C; kerosene - contains hydrocarbons C12 - C18, boiling at a temperature of 180 0 C to 300 0 C; gas oil - contains hydrocarbons C13 - C15, distilled off at a temperature of 230 0 C to 360 0 C; lubricating oils - C16 - C28, boil at a temperature of 350 0 C and above.

After distillation of 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 by additional distillation. The non-distilling part of fuel oil is called tar, which is used in construction and when 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. The problem arises: how to meet the ever-increasing needs of society in automotive and aviation fuel? The solution was found at the end of the 19th century by a Russian engineer Vladimir Grigorievich Shukhov. AT 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% (calculated as 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 with 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 the cracking of petroleum products (from the English "Cracking" - splitting). There are several types of cracking: thermal, catalytic, high pressure cracking, reduction. Thermal cracking consists in the splitting of hydrocarbon molecules with a long chain into shorter ones under the influence of high temperature (470-550 0 C). In the process of this splitting, along with alkanes, alkenes are formed:

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 allows you to get higher quality gasoline. Under the conditions of catalytic cracking, along with cleavage reactions, isomerization reactions take place, that is, the transformation of hydrocarbons of a normal structure into branched hydrocarbons.

Isomerization affects the quality of gasoline, since the presence of branched hydrocarbons greatly increases its octane number. Cracking is referred to the so-called secondary processes of oil refining. A number of other catalytic processes, such as reforming, are also classified as secondary. Reforming- this is the aromatization of gasolines by heating them 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 oilfield

For petrochemical production, the problem of the environment is especially relevant. Oil production is associated with energy costs and environmental pollution. A dangerous source of pollution of the oceans is offshore oil production, and the oceans are also polluted during the transportation of oil. Each of us has seen on TV the consequences of oil tanker accidents. Black, oil-covered shores, black surf, choking dolphins, Birds whose wings are in viscous fuel oil, people in protective suits collecting oil with shovels and buckets. I would like to cite the data of a serious environmental disaster that occurred in the Kerch Strait in November 2007. 2,000 tons of oil products and about 7,000 tons of sulfur got into the water. The Tuzla Spit, which is located at the junction of the Black and Azov Seas, and the Chushka Spit suffered the most because of the disaster. After the accident, fuel oil settled to the bottom, which killed a small shell-heart-shaped, the main food of the inhabitants of the sea. It will take 10 years to restore the ecosystem. More than 15 thousand birds died. A liter of oil, having fallen into the water, spreads over its surface in spots 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 disturbed. "suffocate". Plankton, which is the backbone of the ocean food chain, is dying. Currently, about 20% of the area of ​​the World Ocean is 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” fountains and leaks during well startups, exploratory drilling, and pipeline repairs. The largest area of ​​oil-contaminated land, according to the Committee for the Environment of the Yamalo-Nenets Autonomous Okrug, falls on the Purovsky District.

NATURAL AND ASSOCIATED PETROLEUM GAS

Natural gas contains hydrocarbons with a low molecular weight, the main components are methane. Its content in the gas of various fields ranges from 80% to 97%. In addition to methane - ethane, propane, butane. Inorganic: nitrogen - 2%; CO2; H2O; H2S, noble gases. When natural gas is burned, a lot of heat is released.

In terms of its properties, natural gas as a fuel surpasses even oil, it is more caloric. This is the youngest branch of the fuel industry. Gas is even easier to extract and transport. It is the most economical of all fuels. True, there are also disadvantages: the complex intercontinental transportation of gas. Tankers - methane manure, transporting gas in a liquefied state, are extremely complex and expensive structures.

It is used as: effective fuel, raw material in the chemical industry, in the production of acetylene, ethylene, hydrogen, soot, plastics, acetic acid, dyes, medicines, etc. production. Petroleum gas contains less methane, but more propane, butane and other higher hydrocarbons. Where is the gas produced?

More than 70 countries of the world have commercial 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 opportunities to use it or a way to sell gas to other countries that are on the same continent with them. International gas trade is less active than oil trade. About 15% of the world's produced gas enters the international market. Almost 2/3 of world gas production is provided by 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 Novy Urengoy is rightfully recognized as the gas capital. The largest deposits include Urengoyskoye, Yamburgskoye, Medvezhye, Zapolyarnoye. The Urengoy field is included in the Guinness Book of Records. The reserves and production of the deposit are unique. Explored reserves exceed 10 trillion. m 3 , 6 trln. m 3. In 2008 JSC "Gazprom" plans to produce 598 billion m 3 of "blue gold" at the Urengoy field.

Gas and ecology

The imperfection of the technology of oil and gas production, their transportation causes the constant burning of the volume of gas in the heat units of compressor stations and in flares. Compressor stations account for about 30% of these emissions. About 450,000 tons of natural and associated gas are burned annually at flare installations, while more than 60,000 tons of pollutants enter the atmosphere.

Oil, gas, coal are valuable raw materials for the chemical industry. In the near future, they will find a replacement in the fuel and energy complex of our country. Currently, scientists are looking for ways to use solar and wind energy, nuclear fuel in order to completely replace oil. Hydrogen is the most promising fuel of the future. Reducing the use of oil in thermal power engineering is the way 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 is not changing yet, and up to 94% of the produced oil is used as fuel. D. I. Mendeleev wisely said: “Burning oil is the same as heating the furnace with banknotes.”

The most important natural sources of hydrocarbons are oil , natural gas and coal . They form rich deposits in various regions of the Earth.

Previously, extracted natural products were used exclusively as fuel. At present, methods for their processing have been developed and are widely used, which make it possible to isolate valuable hydrocarbons, which are used both as high-quality fuel and as raw materials for various organic synthesis. Processing of natural sources of raw materials petrochemical industry . Let us analyze the main methods of processing natural hydrocarbons.

The most valuable source of natural raw materials - oil . It is an oily liquid of dark brown or black color with a characteristic odor, practically insoluble in water. The density of oil is 0.73–0.97 g/cm3. Oil is a complex mixture of various liquid hydrocarbons in which gaseous and solid hydrocarbons are dissolved, and the composition of oil from different fields may differ. Alkanes, cycloalkanes, aromatic hydrocarbons, as well as oxygen-, sulfur- and nitrogen-containing organic compounds can be present in various proportions in the composition of oil.

Crude oil is practically not used, but is processed.

Distinguish primary oil refining (distillation ), i.e. separating it into fractions with different boiling points, and recycling (cracking ), during which the structure of hydrocarbons is changed

dov included in its composition.

Primary oil refining It is based on the fact that the boiling point of hydrocarbons is the greater, the greater their molar mass. Oil contains compounds with boiling points from 30 to 550°C. As a result of distillation, oil is separated into fractions boiling at different temperatures and containing mixtures of hydrocarbons with different molar masses. These fractions find a variety of uses (see table 10.2).

Table 10.2. Products of primary oil refining.

Fraction	Boiling point, °C	Compound	Application
Liquefied gas	<30	Hydrocarbons С 3 -С 4	Gaseous fuels, raw materials for the chemical industry
Petrol	40-200	Hydrocarbons C 5 - C 9	Aviation and automotive fuel, solvent
Naphtha	150-250	Hydrocarbons C 9 - C 12	Diesel engine fuel, solvent
Kerosene	180-300	Hydrocarbons С 9 -С 16	Diesel engine fuel, household fuel, lighting fuel
gas oil	250-360	Hydrocarbons С 12 -С 35	Diesel fuel, feedstock for catalytic cracking
fuel oil	> 360	Higher hydrocarbons, O-, N-, S-, Me-containing substances	Fuel for boiler plants and industrial furnaces, feedstock for further distillation

The share of fuel oil accounts for about half of the mass of oil. Therefore, it is also subjected to thermal processing. To prevent decomposition, the fuel oil is distilled under reduced pressure. In this case, several fractions are obtained: liquid hydrocarbons, which are used as lubricating oils ; mixture of liquid and solid hydrocarbons - petrolatum used in the preparation of ointments; a mixture of solid hydrocarbons - paraffin , going to the production of shoe polish, candles, matches and pencils, as well as for the impregnation of wood; non-volatile residue tar used to produce road, construction and roofing bitumen.

Oil refining includes chemical reactions that change the composition and chemical structure of hydrocarbons. Its variety

ty - thermal cracking, catalytic cracking, catalytic reforming.

Thermal cracking usually subjected to fuel oil and other heavy oil fractions. At a temperature of 450–550°C and a pressure of 2–7 MPa, the free radical mechanism splits hydrocarbon molecules into fragments with a smaller number of carbon atoms, and saturated and unsaturated compounds are formed:

C 16 N 34 ¾® C 8 N 18 + C 8 N 16

C 8 H 18 ¾®C 4 H 10 +C 4 H 8

In this way, automobile gasoline is obtained.

catalytic cracking carried out in the presence of catalysts (usually aluminosilicates) at atmospheric pressure and a temperature of 550 - 600°C. At the same time, aviation gasoline is obtained from kerosene and gas oil fractions of oil.

The splitting of hydrocarbons in the presence of aluminosilicates proceeds according to the ionic mechanism and is accompanied by isomerization, i.e. the formation of a mixture of saturated and unsaturated hydrocarbons with a branched carbon skeleton, for example:

CH 3 CH 3 CH 3 CH 3 CH 3

cat., t||

C 16 H 34 ¾¾® CH 3 -C -C-CH 3 + CH 3 -C \u003d C - CH-CH 3

catalytic reforming carried out at a temperature of 470-540°C and a pressure of 1-5 MPa using platinum or platinum-rhenium catalysts deposited on a base of Al 2 O 3 . Under these conditions, the transformation of paraffins and

petroleum cycloparaffins to aromatic hydrocarbons

cat., t, p

¾¾¾¾® + 3H 2

cat., t, p

C 6 H 14 ¾¾¾¾® + 4H 2

Catalytic processes make it possible to obtain improved quality gasoline due to the high content of branched and aromatic hydrocarbons in it. The quality of gasoline is characterized by its octane rating. The more the mixture of fuel and air is compressed by the pistons, the greater the power of the engine. However, compression can only be carried out up to a certain limit, above which detonation (explosion) occurs.

gas mixture, causing overheating and premature engine wear. The lowest resistance to detonation in normal paraffins. With a decrease in the chain length, an increase in its branching and the number of double

ny connections, it increases; it is especially high in aromatic carbohydrates.

before giving birth. To assess the resistance to detonation of various grades of gasoline, they are compared with similar indicators for a mixture isooctane and n-heptane with different ratio of components; the octane number is equal to the percentage of isooctane in this mixture. The larger it is, the higher the quality of gasoline. The octane number can also be increased by adding special antiknock agents, for example, tetraethyl lead Pb(C 2 H 5) 4 , however, such gasoline and its combustion products are toxic.

In addition to liquid fuels, lower gaseous hydrocarbons are obtained in catalytic processes, which are then used as raw materials for organic synthesis.

Another important natural source of hydrocarbons, the importance of which is constantly increasing - natural gas. It contains up to 98% by volume of methane, 2–3% by volume. its closest homologues, as well as impurities of hydrogen sulfide, nitrogen, carbon dioxide, noble gases and water. Gases released during oil production ( passing ), contain less methane, but more of its homologues.

Natural gas is used as fuel. In addition, individual saturated hydrocarbons are isolated from it by distillation, as well as synthesis gas , consisting mainly of CO and hydrogen; they are used as raw materials for various organic syntheses.

Mined in large quantities coal - inhomogeneous solid material of black or gray-black color. It is a complex mixture of various macromolecular compounds.

Coal is used as a solid fuel, and is also subjected to coking – dry distillation without air access at 1000-1200°С. As a result of this process are formed: coke , which is a finely divided graphite and is used in metallurgy as a reducing agent; coal tar , which is subjected to distillation and aromatic hydrocarbons (benzene, toluene, xylene, phenol, etc.) are obtained and pitch , going to the preparation of roofing roofing; ammonia water and coke oven gas containing about 60% hydrogen and 25% methane.

Thus, natural sources of hydrocarbons provide

the chemical industry with diverse and relatively cheap raw materials for organic syntheses, which make it possible to obtain numerous organic compounds that are not found in nature, but are necessary for man.

The general scheme for the use of natural raw materials for the main organic and petrochemical synthesis can be represented as follows.

Arenas Syngas Acetylene AlkenesAlkanes

Basic organic and petrochemical synthesis

Control tasks.

1222. What is the difference between primary oil refining and secondary refining?

1223. What compounds determine the high quality of gasoline?

1224. Suggest a method that allows, starting from oil, to obtain ethyl alcohol.

Target. Generalize knowledge about natural sources of organic compounds and their processing; show the successes and prospects for the development of petrochemistry and coke chemistry, their role in the technical progress of the country; deepen knowledge from the course of economic geography about the gas industry, modern directions of gas processing, raw materials and energy problems; develop independence in working with a textbook, reference and popular science literature.

PLAN

Natural sources of hydrocarbons. Natural gas. Associated petroleum gases.
Oil and oil products, their application.
Thermal and catalytic cracking.
Coke production and the problem of obtaining liquid fuel.
From the history of the development of OJSC Rosneft-KNOS.
The production capacity of the plant. Manufactured products.
Communication with the chemical laboratory.
Environmental protection in the factory.
Plant plans for the future.

Natural sources of hydrocarbons.
Natural gas. Associated petroleum gases

Before the Great Patriotic War, industrial stocks natural gas were known in the Carpathian region, in the Caucasus, in the Volga region and in the North (Komi ASSR). The study of natural gas reserves was associated only with oil exploration. Industrial reserves of natural gas in 1940 amounted to 15 billion m 3 . Then gas fields were discovered in the North Caucasus, Transcaucasia, Ukraine, the Volga region, Central Asia, Western Siberia and the Far East. On the
On January 1, 1976, explored reserves of natural gas amounted to 25.8 trillion m 3, of which 4.2 trillion m 3 (16.3%) in the European part of the USSR, 21.6 trillion m 3 (83.7 %), including
18.2 trillion m 3 (70.5%) - in Siberia and the Far East, 3.4 trillion m 3 (13.2%) - in Central Asia and Kazakhstan. As of January 1, 1980, potential reserves of natural gas amounted to 80–85 trillion m 3 , explored - 34.3 trillion m 3 . Moreover, the reserves increased mainly due to the discovery of deposits in the eastern part of the country - explored reserves there were at a level of about
30.1 trillion m 3, which was 87.8% of the all-Union.
Today, Russia has 35% of the world's natural gas reserves, which is more than 48 trillion m 3 . The main areas of occurrence of natural gas in Russia and the CIS countries (fields):

West Siberian oil and gas province:
Urengoyskoye, Yamburgskoye, Zapolyarnoye, Medvezhye, Nadymskoye, Tazovskoye – Yamalo-Nenets Autonomous Okrug;
Pokhromskoye, Igrimskoye - Berezovskaya gas-bearing region;
Meldzhinskoye, Luginetskoye, Ust-Silginskoye - Vasyugan gas-bearing region.
Volga-Ural oil and gas province:
the most significant is Vuktylskoye, in the Timan-Pechora oil and gas region.
Central Asia and Kazakhstan:
the most significant in Central Asia is Gazli, in the Ferghana Valley;
Kyzylkum, Bairam-Ali, Darvaza, Achak, Shatlyk.
North Caucasus and Transcaucasia:
Karadag, Duvanny - Azerbaijan;
Dagestan Lights - Dagestan;
Severo-Stavropolskoye, Pelagiadinskoye - Stavropol Territory;
Leningradskoye, Maykopskoye, Staro-Minskoye, Berezanskoye - Krasnodar Territory.

Also, natural gas deposits are known in Ukraine, Sakhalin and the Far East.
In terms of natural gas reserves, Western Siberia stands out (Urengoyskoye, Yamburgskoye, Zapolyarnoye, Medvezhye). Industrial reserves here reach 14 trillion m 3 . The Yamal gas condensate fields (Bovanenkovskoye, Kruzenshternskoye, Kharasaveyskoye, etc.) are now acquiring particular importance. On their basis, the Yamal-Europe project is being implemented.
Natural gas production is highly concentrated and focused on areas with the largest and most profitable deposits. Only five deposits - Urengoyskoye, Yamburgskoye, Zapolyarnoye, Medvezhye and Orenburgskoye - contain 1/2 of all industrial reserves of Russia. The reserves of Medvezhye are estimated at 1.5 trillion m 3 , and those of Urengoy – at 5 trillion m 3 .
The next feature is the dynamic location of natural gas production sites, which is explained by the rapid expansion of the boundaries of the identified resources, as well as the relative ease and cheapness of their involvement in development. In a short time, the main centers for the extraction of natural gas moved from the Volga region to Ukraine, the North Caucasus. Further territorial shifts were caused by the development of deposits in Western Siberia, Central Asia, the Urals and the North.

After the collapse of the USSR in Russia, there was a drop in the volume of natural gas production. The decline was observed mainly in the Northern economic region (8 billion m 3 in 1990 and 4 billion m 3 in 1994), in the Urals (43 billion m 3 and 35 billion m and
555 billion m 3) and in the North Caucasus (6 and 4 billion m 3). Natural gas production remained at the same level in the Volga region (6 bcm) and in the Far East economic regions.
At the end of 1994, there was an upward trend in production levels.
Of the republics of the former USSR, the Russian Federation provides the most gas, in second place is Turkmenistan (more than 1/10), followed by Uzbekistan and Ukraine.
Of particular importance is the extraction of natural gas on the shelf of the World Ocean. In 1987, offshore fields produced 12.2 billion m 3 , or about 2% of the gas produced in the country. Associated gas production in the same year amounted to 41.9 bcm. For many areas, one of the reserves of gaseous fuel is the gasification of coal and shale. Underground gasification of coal is carried out in the Donbass (Lysichansk), Kuzbass (Kiselevsk) and the Moscow Basin (Tula).
Natural gas has been and remains an important export product in Russian foreign trade.
The main natural gas processing centers are located in the Urals (Orenburg, Shkapovo, Almetyevsk), in Western Siberia (Nizhnevartovsk, Surgut), in the Volga region (Saratov), ​​in the North Caucasus (Grozny) and in other gas-bearing provinces. It can be noted that gas processing plants tend to sources of raw materials - deposits and large gas pipelines.
The most important use of natural gas is as a fuel. Recently, there has been a trend towards an increase in the share of natural gas in the country's fuel balance.

The most valued natural gas with a high content of methane is Stavropol (97.8% CH 4), Saratov (93.4%), Urengoy (95.16%).
Natural gas reserves on our planet are very large (approximately 1015 m 3). More than 200 deposits are known in Russia, they are located in Western Siberia, in the Volga-Ural basin, in the North Caucasus. Russia holds the first place in the world in terms of natural gas reserves.
Natural gas is the most valuable type of fuel. When gas is burned, a lot of heat is released, so it serves as an energy-efficient and cheap fuel in boiler plants, blast furnaces, open-hearth furnaces and glass melting furnaces. The use of natural gas in production makes it possible to significantly increase labor productivity.
Natural gas is a source of raw materials for the chemical industry: the production of acetylene, ethylene, hydrogen, soot, various plastics, acetic acid, dyes, medicines and other products.

Associated petroleum gas- this is a gas that exists together with oil, it is dissolved in oil and is located above it, forming a "gas cap", under pressure. At the exit from the well, the pressure drops, and the associated gas is separated from the oil. This gas was not used in the past, but was simply burned. It is currently being captured and used as a fuel and valuable chemical feedstock. The possibilities of using associated gases are even wider than those of natural gas. their composition is richer. Associated gases contain less methane than natural gas, but they contain significantly more methane homologues. In order to use associated gas more rationally, it is divided into mixtures of a narrower composition. After separation, gas gasoline, propane and butane, dry gas are obtained. Individual hydrocarbons are also extracted - ethane, propane, butane and others. By dehydrogenating them, unsaturated hydrocarbons are obtained - ethylene, propylene, butylene, etc.

Oil and oil products, their application

Oil is an oily liquid with a pungent odor. It is found in many places on the globe, impregnating porous rocks at various depths.
According to most scientists, oil is the geochemically altered remains of plants and animals that once inhabited the globe. This theory of the organic origin of oil is supported by the fact that oil contains some nitrogenous substances - the decomposition products of substances present in plant tissues. There are also theories about the inorganic origin of oil: its formation as a result of the action of water in the strata of the globe on hot metal carbides (compounds of metals with carbon), followed by a change in the resulting hydrocarbons under the influence of high temperature, high pressure, exposure to metals, air, hydrogen, etc.
When oil is extracted from oil-bearing strata, which sometimes lie in the earth's crust at a depth of several kilometers, oil either comes to the surface under the pressure of gases located on it, or is pumped out by pumps.

The oil industry today is a large national economic complex that lives and develops according to its own laws. What does oil mean today for the national economy of the country? Oil is a raw material for petrochemistry in the production of synthetic rubber, alcohols, polyethylene, polypropylene, a wide range of various plastics and finished products from them, artificial fabrics; a source for the production of motor fuels (gasoline, kerosene, diesel and jet fuels), oils and lubricants, as well as boiler and furnace fuel (fuel oil), building materials (bitumen, tar, asphalt); raw material for obtaining a number of protein preparations used as additives in livestock feed to stimulate its growth.
Oil is our national wealth, the source of the country's power, the foundation of its economy. The oil complex of Russia includes 148 thousand oil wells, 48.3 thousand km of main oil pipelines, 28 oil refineries with a total capacity of more than 300 million tons of oil per year, as well as a large number of other production facilities.
About 900,000 employees are employed at the enterprises of the oil industry and its service industries, including about 20,000 people in the field of science and scientific services.
Over the past decades, fundamental changes have taken place in the structure of the fuel industry associated with a decrease in the share of the coal industry and the growth of oil and gas extraction and processing industries. If in 1940 they amounted to 20.5%, then in 1984 - 75.3% of the total production of mineral fuel. Now natural gas and open pit coal are coming to the fore. The consumption of oil for energy purposes will be reduced, on the contrary, its use as a chemical raw material will expand. Currently, in the structure of the fuel and energy balance, oil and gas account for 74%, while the share of oil is declining, while the share of gas is growing and is approximately 41%. The share of coal is 20%, the remaining 6% is electricity.
Oil refining was first started by the Dubinin brothers in the Caucasus. Primary oil refining consists in its distillation. Distillation is carried out at refineries after the separation of petroleum gases.

A variety of products of great practical importance are isolated from oil. First, dissolved gaseous hydrocarbons (mainly methane) are removed from it. After distillation of volatile hydrocarbons, the oil is heated. Hydrocarbons with a small number of carbon atoms in the molecule, which have a relatively low boiling point, are the first to go into a vapor state and are distilled off. As the temperature of the mixture rises, hydrocarbons with a higher boiling point are distilled. In this way, individual mixtures (fractions) of oil can be collected. Most often, with this distillation, four volatile fractions are obtained, which are then subjected to further separation.
The main oil fractions are as follows.
Gasoline fraction, collected from 40 to 200 ° C, contains hydrocarbons from C 5 H 12 to C 11 H 24. Upon further distillation of the isolated fraction, gasoline (t kip = 40–70 °C), petrol
(t kip \u003d 70–120 ° С) - aviation, automobile, etc.
Naphtha fraction, collected in the range from 150 to 250 ° C, contains hydrocarbons from C 8 H 18 to C 14 H 30. Naphtha is used as fuel for tractors. Large quantities of naphtha are processed into gasoline.
Kerosene fraction includes hydrocarbons from C 12 H 26 to C 18 H 38 with a boiling point of 180 to 300 °C. Kerosene, after being refined, is used as a fuel for tractors, jet planes and rockets.
Gas oil fraction (t bale > 275 °C), otherwise called diesel fuel.
Residue after distillation of oil - fuel oil- contains hydrocarbons with a large number of carbon atoms (up to many tens) in the molecule. The fuel oil is also fractionated by reduced pressure distillation to avoid decomposition. As a result, get solar oils(diesel fuel), lubricating oils(autotractor, aviation, industrial, etc.), petrolatum(technical petroleum jelly is used to lubricate metal products in order to protect them from corrosion, purified petroleum jelly is used as a basis for cosmetics and in medicine). From some types of oil paraffin(for the production of matches, candles, etc.). After distillation of volatile components from fuel oil remains tar. It is widely used in road construction. In addition to processing into lubricating oils, fuel oil is also used as liquid fuel in boiler plants. Gasoline obtained during the distillation of oil is not enough to cover all needs. In the best case, up to 20% of gasoline can be obtained from oil, the rest is high-boiling products. In this regard, chemistry faced the task of finding ways to obtain gasoline in large quantities. A convenient way was found with the help of the theory of the structure of organic compounds created by A.M. Butlerov. High-boiling oil distillation products are unsuitable for use as a motor fuel. Their high boiling point is due to the fact that the molecules of such hydrocarbons are too long chains. If large molecules containing up to 18 carbon atoms are broken down, low-boiling products such as gasoline are obtained. This way was followed by the Russian engineer V.G. Shukhov, who in 1891 developed a method for the splitting of complex hydrocarbons, later called cracking (which means splitting).

The fundamental improvement of cracking was the introduction of the catalytic cracking process into practice. This process was first carried out in 1918 by N.D. Zelinsky. Catalytic cracking made it possible to produce aviation gasoline on a large scale. In catalytic cracking units at a temperature of 450 °C, under the action of catalysts, long carbon chains are split.

Thermal and catalytic cracking

The main way of processing oil fractions are various types of cracking. For the first time (1871–1878), oil cracking was carried out on a laboratory and semi-industrial scale by A.A. Letniy, an employee of the St. Petersburg Technological Institute. The first patent for a cracking plant was filed by Shukhov in 1891. Cracking has become widespread in industry since the 1920s.
Cracking is the thermal decomposition of hydrocarbons and other constituents of oil. The higher the temperature, the greater the cracking rate and the greater the yield of gases and aromatics.
Cracking of oil fractions, in addition to liquid products, produces a raw material of paramount importance - gases containing unsaturated hydrocarbons (olefins).
There are the following main types of cracking:
liquid phase (20–60 atm, 430–550 °C), gives unsaturated and saturated gasoline, the yield of gasoline is about 50%, gases 10%;
headspace(normal or reduced pressure, 600 °C), gives unsaturated aromatic gasoline, the yield is less than with liquid-phase cracking, a large amount of gases is formed;
pyrolysis oil (normal or reduced pressure, 650–700 °C), gives a mixture of aromatic hydrocarbons (pyrobenzene), a yield of about 15%, more than half of the raw material is converted into gases;
destructive hydrogenation (hydrogen pressure 200–250 atm, 300–400 °C in the presence of catalysts - iron, nickel, tungsten, etc.), gives marginal gasoline with a yield of up to 90%;
catalytic cracking (300–500 °С in the presence of catalysts - AlCl 3 , aluminosilicates, MoS 3 , Cr 2 O 3 , etc.), gives gaseous products and high-grade gasoline with a predominance of aromatic and saturated hydrocarbons of isostructure.
In technology, the so-called catalytic reforming– conversion of low-grade gasolines into high-grade high-octane gasolines or aromatic hydrocarbons.
The main reactions during cracking are the reactions of splitting hydrocarbon chains, isomerization and cyclization. Free hydrocarbon radicals play a huge role in these processes.

Coke production
and the problem of obtaining liquid fuel

Stocks hard coal in nature far exceed oil reserves. Therefore, coal is the most important type of raw material for the chemical industry.
Currently, industry uses several ways of coal processing: dry distillation (coking, semi-coking), hydrogenation, incomplete combustion, and calcium carbide production.

Dry distillation of coal is used to obtain coke in metallurgy or domestic gas. When coking coal, coke, coal tar, tar water and coking gases are obtained.
Coal tar contains a wide variety of aromatic and other organic compounds. It is separated into several fractions by distillation at normal pressure. Aromatic hydrocarbons, phenols, etc. are obtained from coal tar.
coking gases contain mainly methane, ethylene, hydrogen and carbon monoxide (II). Some are burned, some are recycled.
Hydrogenation of coal is carried out at 400–600 °C under a hydrogen pressure of up to 250 atm in the presence of a catalyst, iron oxides. This produces a liquid mixture of hydrocarbons, which are usually subjected to hydrogenation on Nickel or other catalysts. Low-grade brown coals can be hydrogenated.

Calcium carbide CaC 2 is obtained from coal (coke, anthracite) and lime. Later it is converted into acetylene, which is used in the chemical industry of all countries on an ever-increasing scale.

From the history of the development of OJSC Rosneft-KNOS

The history of the development of the plant is closely connected with the oil and gas industry of the Kuban.
The beginning of oil production in our country is a distant past. Back in the X century. Azerbaijan traded oil with various countries. In the Kuban, industrial oil development began in 1864 in the Maykop region. At the request of the head of the Kuban region, General Karmalin, D.I. Mendeleev in 1880 gave an opinion on the oil content of the Kuban: Ilskaya".
During the years of the first five-year plans, large-scale prospecting work was carried out and commercial oil production began. Associated petroleum gas was partially used as household fuel in workers' settlements, and most of this valuable product was flared. In order to put an end to the wastefulness of natural resources, the USSR Ministry of the Oil Industry in 1952 decided to build a gas and gasoline plant in the village of Afipsky.
During 1963, an act was signed for the commissioning of the first stage of the Afipsky gas and gasoline plant.
At the beginning of 1964, the processing of gas condensates from the Krasnodar Territory began with the production of A-66 gasoline and diesel fuel. The raw material was gas from Kanevsky, Berezansky, Leningradsky, Maikopsky and other large fields. Improving production, the staff of the plant mastered the production of B-70 aviation gasoline and A-72 gasoline.
In August 1970, two new technological units for the processing of gas condensate with the production of aromatics (benzene, toluene, xylene) were put into operation: a secondary distillation unit and a catalytic reforming unit. At the same time, treatment facilities with biological wastewater treatment and the commodity and raw material base of the plant were built.
In 1975, a unit for the production of xylenes was put into operation, and in 1978, an import-made toluene demethylation unit was put into operation. The plant has become one of the leaders in the Minnefteprom for the production of aromatic hydrocarbons for the chemical industry.
In order to improve the management structure of the enterprise and the organization of production units in January 1980, the production association Krasnodarnefteorgsintez was established. The association included three plants: the Krasnodar site (in operation since August 1922), the Tuapse oil refinery (in operation since 1929) and the Afipsky oil refinery (in operation since December 1963).
In December 1993, the enterprise was reorganized, and in May 1994 Krasnodarnefteorgsintez OJSC was renamed into Rosneft-Krasnodarnefteorgsintez OJSC.

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