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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
oil and its derivates
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
oil and its derivates
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
oil and its derivates
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?
5
oil and its derivates
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
6
oil and its derivates
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
7
oil and its derivates
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.
8
oil and its derivates
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
9
oil and its derivates
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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oil and its derivates
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
11
oil and its derivates
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
12
oil and its derivates
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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oil and its derivates
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.
14
oil and its derivates
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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oil and its derivates
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
16
oil and its derivates
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
oil and its derivates
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
oil and its derivates
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
oil and its derivates
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)
20
oil and its derivates
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.
21
oil and its derivates
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
22
oil and its derivates
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.
23
oil and its derivates
Flow Chart
Materiale sviluppato da eniscuola nell’ambito del protocollo d’intesa con il MIUR
Start
extraction
Fractional distillation
refining
polymerization
transformation
the end