oil and its derivates -...

chemistry course exercises

Liceo Scientifico Isaac Newton – Roma

oil and its derivates

in accordo con il Ministero dell’Istruzione, Università, Ricerca

e sulla base delle Politiche Linguistiche della Commissione Europea

percorso formativo a carattere tematico-linguistico-didattico-metodologico

scuola secondaria di secondo grado

professor

Luciana Leonzi

2


Indice Modulo

Strategies - Before

• Prerequisites

• Linking to Previous Knowledge and Predicting con questionari basati su stimoli relativi alle conoscenze pregresse e alle ipotesi riguardanti i contenuti da affrontare

• Italian/English Glossary

Strategies – During

• Video con scheda grafica • Keywords riferite al video attraverso esercitazioni mirate • Conceptual Map

Strategies - After

• Esercizi: � Multiple Choice � Matching

� True or False � Cloze o Completion � Flow Chart

� Think and Discuss

• Summary per abstract e/o esercizi orali o scritti basati su un questionario e per esercizi quali traduzione e/o dettato

• Web References di approfondimento come input interattivi per test orali e scritti e per esercitazioni basate sul Problem Solving

Answer Sheets

3


1

Strategies Before

Prerequisites

Concepts of element and compound Difference between mixture and compound Methods of separating mixtures Atom structure Chemical bonds Hybrid orbitals Catalyst

Oxidoreduction reactions

4


2

Strategies Before

Linking to Previous Knowledge and Predicting

1. What do we mean by heterogeneous mixture?

2. What is the difference between a mixture and a compound?

3. You want to separate salt from sand, how do you proceed?

4. How does a covalent bond polar form?

5. Why are the non-polar covalent substances insoluble in water?

6. What are the main types of hybrid orbitals?

7. What is the difference between σ bond and π bond?

8. Why are most substances in compounds form instead of single elements?

9. What do we mean by oxidation number?

10. When does an oxidoreduction occur?

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3

Strategies Before

Italian/English Glossary

Alcani o paraffine Alkanes or Paraffines Alcheni AlKenes Antidetonante Anti-knock Atomo Atom Azoto Nytrogen Asfalto Asphalt Benzene Benzene Benzina Gasoline Catena lineare Straight chain Catena ramificata Branched chain Carbonio Carbon Catrame Tar Cera Wax Carbocatione Carbocation Catalizzatore Catalyst Cherosene Kerosene Cicloalcani Cycloalkanes or naphthenes Colonna di distillazione Distilling column Combustibile Fuel Composto Compound Condensare To condense Delocalizzato Delocalized Densità Density Derivato Derivate Desulfurizzazione Desulphurization Distillazione frazionata Fractional distillation Distillazione sotto vuoto Vacuum distillation Elettrone Electron Energia Energy Esano Hexane Esotermico Exothermic Etano Ethane Etilene o etene Ethylene or ethene Formula Formula Gassoso Gaseous Giacimento Oil field Greggio Crude oil Idrocarburo Hydrocarbon Idrocarburi aromatici Aromatic hydrocarbons Idrogeno Hydrogen

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Isobutano Isobutane Insaturo Unsaturated Isomerizzazione Isomerization Legame covalente semplice Single covalent bond Legame covalente doppio Double covalent bond Liquido Liquid Lubrificante Lubricating Materie plastiche Plastics Materia prima Raw material Metano Methane Metil Methyl Miscuglio Mixture Molecola Molecule Monomero Monomer Nafta Naphtha Ossigeno Oxygen Petrolio Petroleum or oil Picco del petrolio Peak oil Polimero Polymer Pozzo petrolifero Oil well Punto di ebollizione Boiling point Radicale Radical Raffinazione Refining Reazione Reaction Scissione omolitica Homolytic fission Scissione eterolitica Heterolytic fission Solido Solid Sotto vuoto Vacuum Struttura Structure Temperatura Temperature Toluene Toluene Vapore Vapor Viscosità Viscosity Zolfo Sulfur

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4

Strategies During

Keywords

1) Circle which of the following substances are examples of hydrocarbons:

Methane, plastics, residue, benzene, polymer, isobutene, isomer, ethane, gasoline, cycloalkane, monomer, kerosene, toluene, propane, paraffins

2) Circle which of the following processes are used for the oil refining:

oxidoreduction, fractional distillation, combustion, polymerization,

transformation, cracking, isomerization, reforming, extraction.

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5

Strategies During

Conceptual Map

Complete the conceptual map, using the following words:

is

of of

separated

into into

Some subjected to reforming

that can occur that can occur

divided

into

Petroleum gas (1 to 4 C) Naphtha (5 to 9 C) Gasoline (5 to 10 C) Kerosene (10 to 18 C) Gas oil or diesel Heavy gas Lubricating oil Coke, asphalt, tar, waxes

Organic compounds different from hydrocarbons

Alkanes

Cycloalkanes

Some subjected to cracking

Alkanes (6-9 carbon atoms)converted into alkenes, alkenes into aromatic hydrocarbons

Petroleum

widely

used

For energy

For transport

A mixture of, hydrocarbons, aromatic hydrocarbons, at atmospheric pressure, vacuum, long chain hydrocarbons into shorter chain hydrocarbons, for chemical industry.

By fractional distillation

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6

Strategies After Multiple Choice

1. The general formula of alkanes is:

a. Cn H n b. C2n H2n+2 c. Cn H2n+2 d. Cn H2n-2

2. The formula of benzene is:

a. C2 H4 b. C6 H8 c. C2 H6 d. C6 H6

3. Identify among the compounds following those which are isomers.

a. CH3 - CH2 - CH2 - OH b. CH3 - CH2 - CH3 c. CH3 – CH2 – CH2- CH3 d. CH3 - CH2 - CH2 - CH2 - CH3 e. CH3 - CH2 - O - CH3 f. CH3 - CH2 - CH2 - CH3

4. Two alkanes are certainly isomers when...

a. they have the same structural formula b. they have different molecular formula, but the same physical properties

c. they are formed by the same atoms, bound in a different way d. they have the same structural formula, but different molecular weight

5. In the organic compounds carbon atom is always tetravalent, this means that:

a. carbon atom contains the valence electrons in fourth energy level b. carbon atom is always bound a four different atoms c. carbon atom is bound at four hydrogen atoms d. carbon atom always forms four covalent bonds

6. Petroleum is…. a. an heterogeneous mixture of hydrocarbons b. a polymer of hydrocarbons c. a heterogeneous mixture of hydrocarbons and other organic molecules

d. an organic compound containing atoms of carbon and hydrogen

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7. The fractional distillation of oil is based on: a. different nature of chemical bonds of hydrocarbons b. mass of hydrocarbons c. the freezing point of hydrocarbons d. the boiling point of hydrocarbons

8. The cracking process increases the yield on gasoline..... a. because it produces longer chain alkanes b. because it produces branched and shorter chain alkanes c. because it produces cycloalkane d. because it produces polymers

9. In the vacuum distillation…… a. the residue of atmospheric distillation is separated into its components b. lower molecular weight hydrocarbons are transformed into higher weight

molecular hydrocarbons c. fractional distillation occurs at a higher pressure. d. the yield of gasoline is increased 10. An alkane is called saturated because: a. it is a straight chain hydrocarbon b. all carbon atoms are bound by a single bond c. it dissolves in organic solvents d. it contains only carbon atoms

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7

Strategies After

Matching

Match the sentences defined with a letter with the correct part defined with a

number:

1. The alkanes molecules

2. The molecules of aromatic hydrocarbons

3. The residue of atmospheric distillation is subjected to vacuum distillation

4. The cracking process

5. The reforming process

6. The combustion

7. The cycloalkanes

8. The elastomers

9. Refining

a. transforms naphthenes into aromatic compounds, keeping the same number of carbon atoms

b. is an exothermic reaction c. breaks the bonds of long chain hydrocarbons producing mixtures of smaller chain

alkanes and alkenes

d. are polymerization products e. is the set of the processes which make it possible to obtain the petroleum

derivates

f. are hydrocarbons with one or more rings of carbon atoms to which hydrogen atoms are bound according to the formula CnH2n

g. contain only single covalent bonds in their molecules. h. are formed by one or more rings of carbon atoms and characterized by presence of

π delocalized electrons

i. to avoid molecules decomposition at high temperature

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8

Strategies After

True or False

State if the sentences are true or false.

1. Hydrocarbons molecules are formed by chains of carbon atoms of various length.

2. σ bonds are absent in hydrocarbons

3. Alkanes molecules are formed by straight or branched chains

4. A type of polymerization occurs by addition of molecules with fewer than five

carbon atoms

5. Three-dimensional polymers form thermoplastic resins or unvulcanized elastomers

6. Atmospheric fractional distillation occurs at a constant temperature

7. ∆G of combustion reaction has negative sign

8. Crude oil is an organic substance.

9. The cracking process is used to separate the components of the oil

a. CH3

b. | 10. The formula of 2-Methylpentane is CH3-CH- CH2-CH2- CH3

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9

Strategies After

Cloze

A) Petroleum constituents containing fewer than..1.. carbon atoms can be converted

into ..2..molecular weight hydrocarbons via..3.. polymerization. Linear ..4..

form..5.. resins or unvulcanized elastomers, ..6. .polymers form thermosetting

..7.. or vulcanized elastomers. In the case of polyethene polymerization, the ..8..

of double bond between the ..9.. atoms of ethene molecules is broken, so that the

molecules of ethane can bind to each other

B) To obtain the petroleum ..1.., crude oil is subjected to different processes. The

first process is fractional ..2.. during which the oil components are separated

according to their..3.. Through cracking and reforming processes, many

distillation products are transformed into others, in order to improve their ..4.. or

to increase their ..5.. During cracking the ..6.. between carbon atoms is broken,

so long chains of hydrocarbons molecules are transformed into ..7 .. chains.

Through the reforming process some alkanes can be converted into ..8..

hydrocarbons. Most oil derivates are used as fuel; the other derivates are used as

..9.. for the chemical industry.

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10

Strategies After

Flow Chart

Complete the flow chart representing the sequence of events occurring in the entire manufacturing cycle from oil to plastic products.

refining

Start

polymerization

transformation

Fractional distillation

crude oil

extraction

The end

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11

Strategies After

Think and Discuss

The following activity can be performed in a written or oral form. The teacher will

choose the modality, depending on the ability (writing or speaking) that needs to be

developed.

The contexts in which the task will be presented to the students are:

A) the student is writing an article about petroleum

B) the student is preparing for an interview on a local TV about petroleum

The student should:

1) Choose one of the following topics:

• Describe and highlights the differences between the various types of

hydrocarbons

• Fractional distillation of oil is based on the different boiling point of

hydrocarbons. In your opinion, what is the reason of this difference?

2) Prepare the article or the debate, outlining the main points of the argument, on

the basis of what has been studied.

3) If the written activity is the modality chosen by the teacher, the student should

provide a written article, indicating the target of readers to whom the article is

addressed and the type of magazine / newspaper / school magazine where the

article would be published.

4) If the oral activity is the modality chosen by the teacher, the student should present his point of view on the topics to the whole class and a debate could

start at the end of his presentation

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12

Strategies After

Summary

Petroleum or oil is a mixture of hydrocarbons and small amounts of other organic

compounds. The oil hydrocarbons are alkanes, cycloalkanes and aromatic

hydrocarbons. There aren’t alkenes and alkynes, which form during some refining

processes.

The crude oil doesn’t have almost any possibility of application, unlike its derivates,

obtained through refining processes.

Refining begins with fractional distillation. Oil is heated at temperature above 340°C

in a furnace, the vapours are piped into a distillation column, where the oil fractions

are separated according their boiling point.

Distillation products are petroleum gasses (they include liquefiable gasses, as propane

and butane, known as GPL), gasoline, kerosene, gas oil, heavy oil and residual, from

which fuel oil, lubricating oil, waxes, and bitumen are obtained by vacuum distillation

Only heavy fractions and residual can be marketed directly.

In order to increase the yield of gasoline, the product with the most important

commercial value, and also to obtain products suitable as raw material for

petrochemical, the other fractions are subjected to further processes as cracking and

reforming.

Trough cracking, the long chains of carbon atoms of paraffin are broken

into shorter-chain alkanes. The process occurs by the action of temperature, pressure

and suitable catalysts, this last modality is the most commonly used.

The products of this process are alkanes and alkenes, saturated and unsaturated

hydrocarbons, with low molecular weight, used to obtain gasoline components; other

alkanes for making plastics and carbon coke for the steel and aluminum industry

Through reforming hydrocarbons molecules undergo profound changes in their

structure while retaining the same number of carbon atoms. The process occurs at

high pressure and temperature and in presence of catalysts. It improves the quality

of gasoline, increasing its anti-Knock power.

The most important reaction bound to the use of oil fraction is combustion, redox reaction, highly exothermic. Part of the hydrocarbon fractions extracted from oil are used as raw material for plastics.

17


1. Answer to the following questions:

a) How does the heterolytic fission of σ bond between two carbon

atoms take place?

b) How does the vacuum distillation occur?

c) What are the characteristics of the benzene ring

d) What is a polymer?

e) How do you explain the great variety of hydrocarbons?

f) What is the difference between alkanes and aromatic hydrocarbons?

g) What is the importance of polymerization in the transformation of hydrocarbons into plastics? h) What is role of isomerization in the oil refining process? i) How many different types of hybridization may be performed by a carbon atom?

2. Write a short abstract of the summary (about 150 words), highlighting

the main points of the video.

18


Web References

Websites about hydrocarbons

In the first website there is also the structural formula of ethane with animation

http://www.territorioscuola.com/wikipedia/it.wikibooks.php?title=Chimica_organica/Al

cani_(Conformazione)

http://chemistry.about.com/od/lecturenoteslabs/a/Alkanes.htm

http://www.eoearth.org/article/Hydrocarbon_chemistry?topic=49557

http://chemed.chem.purdue.edu/genchem/topicreview/bp/1organic/hydro.html

video about structural formulas of hydrocarbons in following website

http://www.youtube.com/watch?v=snLbLIDke_o&feature=related

http://www.chemguide.co.uk/organicprops/alkanes/cracking.html#top

http://www.youtube.com/watch?v=snLbLIDke_o&feature=related

Websites about the refining process

http://www.petroleum.co.uk/

http://www.aip.com.au/industry/fact_refine.htm

http://www.green-planet-solar-energy.com/fractional-distillation-of-crude-oil.html

http://www.eoearth.org/article/Cracking

Websites about reserves, consumption, production of petroleum

http://www.nationmaster.com/cat/ene-energy

http://www.huffingtonpost.com/tag/country-with-most-oil

http://www.infoplease.com/ipa/A0922041.html

Website videos about oil peak

http://www.google.it/search?q=oil+peak+2011&hl=it&rlz=1G1GGLQ_ITIT377&prmd

=ivns&source=univ&tbm=vid&tbo=u&sa=X&ei=TgSiTcKAEM30sgaApIHtAQ&ved=0CH

wQqwQ

http://www.engineeringnews.co.za/article/global-oil-production-likely-to-peak-in-

2011-analyst-2008-03-18

http://www.crudeoilpeak.com/?page_id=51

http://www.hubbertpeak.com/

Websites about plastics

http://www.americanchemistry.com/hops/intro_to_plastics/teachers.html#resinid

http://sunfh.tripod.com/chem3.htm

http://science.howstuffworks.com/plastic5.htm

19


In the following websites there is the protocol of the experiment about the

polymerization: “from milk to plastic”

http://www.google.it/url?sa=t&source=web&cd=10&sqi=2&ved=0CHUQxQEwCQ&url

=http%3A%2F%2Fdocs.google.com%2Fviewer%3Fa%3Dv%26q%3Dcache%3A9_LJX

UH_dewJ%3Aumanitoba.ca%2Foutreach%2Fcrystal%2Fresources%252520for%2525

20teachers%2FPolymerization%252520-

%252520Christy%252520Boettcher%252520%2526.doc%2Bpolymerization%2Bfor%

2Bplastics%26hl%3Dit%26gl%3Dit%26pid%3Dbl%26srcid%3DADGEEShh4GYfZTXzIT

KO5-

kO_WPlySLRuIpYfLiC_x5jaJ_9UUbqQke7I3wxkwxp12xYN64pMUgSONNOMXQTbNCogk

3dEm7OCYp1RTPgWlgNiCLkmeVCbAesNqReWmdqvDpRKcr5Ge_J%26sig%3DAHIEtbQ

sP0f9dRG6Zr9L8HCht94wA7d8gg&ei=Pw-

iTaS9B4z2sgb15JCHAg&usg=AFQjCNESEmeboFVOcDiXqNCxcsKCqKbEew&sig2=bNTM

8szY-hmMoH953a3IKQ

Websites about bioplastics

http://www.chemeurope.com/en/encyclopedia/Bioplastic.html#_ref-15/

http://www.thenakedscientists.com/HTML/articles/article/bioplastics

http://portal.acs.org/preview/fileFetch/C/CNBP_024548/pdf/CNBP_024548.pdf

http://www.eucia.org/uploads/3f75f56f43c63b9defafb9f6441714b2.pdf

https://www.cia.gov/library/publications/the-world-

factbook/rankorder/2178rank.html

http://www.energoclub.it/doceboCms/page/31/Fonti_primarie_Petrolio.html

http://www.bp.com/sectiongenericarticle.do?categoryId=9023769&contentId=704491

5

http://www.green-planet-solar-energy.com/plastics-raw-materials.htm

Websites about biofuels

http://greenexperience.net/evolution-of-biofuels/

http://www.green-planet-solar-energy.com/biofuel.html

http://evolution.berkeley.edu/evolibrary/news/090401_biofuels

http://www.thebioenergysite.com/articles/861/ethanols-evolution-new-research-

goes-beyond-corn

Video website MoneyTV01 (MoneyTV-Evolution of biofuel feed stock)

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13

Activities Based on Problem Solving

The following activities can be performed at school, if a computer room is

available, or at home. Students are invited to use the web references listed

above.

1) Small group activity.

Choose one of the following topics related to petroleum, use the web

references listed above, prepare a power point presentation and present

it to your classmates.

Topics:

a. The development of biofuels: after the questions raised by use of corn or sugar cane, attention is concentrated on second and third generation biofuels.

Describe the differences in production and the different consequences in

environmental and food safety.

b. The oil is running out? Read up on the current reserves and prospects for the future

2) Class project.

Elaborate a poster indicating oil importance in our daily life. You can pin

up the poster in your school.

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Answer Sheets

Keywords:

1) Methane, benzene, isobutene, ethane, cycloalkane, toluene, propane, paraffins. 2) fractional distillation, polymerization, cracking, isomerization, reforming. Conceptual Map:

is

of of

separated

into into

Some subjected to reforming

that can occur that can occur

divided

into hydrocarbons

Petroleum gas (1 to 4 C) Naphtha (5 to 9 C) Gasoline (5 to 10 C) Kerosene (10 to 18 C) Gas oil or diesel Heavy gas Lubricating oil Coke, asphalt, tar, waxes

a mixture of

organic compounds different from hydrocarbons

alkanes

Aromatic hydrocarbons

cycloalkanes

long chain hydrocarbons into shorter chain hydrocarbons

Some subjected to cracking

alkanes (6-9 carbon atoms)into alkenes, alkenes into aromatic

at atmospheric

pressure

vacuum

widely

used

for chemical

industry

for energy

for transport

by fractional distillation

Petroleum

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Multiple Choice: 1c; 2d; 3a-e; 4c; 5d; 6c; 7d; 8b; 9a; 10b.

Matching:

1g; 2h; 3i; 4c; 5a; 6b; 7f; 8d; 9e.

True or False:

1true; 2 false; 3 true; 4 true; 5 false; 6 false; 7 true; 8 false; 9 false; 10 true

Cloze:

A) 1.five 2. higher 3. acid-catalyzed 4. polymers 5. thermoplastic 6. three-

dimensional 7. resins 8. π bond 9. carbon

B) 1. derivates 2. distillation 3. boiling points 4. quality 5. amounts 6. σ bond 7.

shorter 8. aromatic 9. raw materials.

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Flow Chart

Materiale sviluppato da eniscuola nell’ambito del protocollo d’intesa con il MIUR

Start

extraction

Fractional distillation

refining

polymerization

transformation

the end

oil and its derivates -...

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