Chapter 23Chapter 23

Organic Chemistry

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MethaneMethane

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ButanesButanes

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CycloalkanesCycloalkanes

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Gasoline-KnockingGasoline-Knocking

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Internal Combustion EngineInternal Combustion EngineBox 8.2, pg. 285 Text

C9H20(l) + 14O2(g) ---> 9CO2(g) + 10H2O(g)

CH3 CH3 | |CH3 - C - CH2 - CH - CH3 | CH3 isooctaneoctane number = 100

CH3- CH2- CH2- CH2- CH2- CH2- CH3

n-heptaneoctane number = 0

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Octane RatingOctane Rating

(R+M)/2R - RON - research octane number,

indicates the quality of the fuel used under normal driving conditions. The car is driving on level ground ~ 45 miles/hour. The RON engine is operating at 600 RPMs with normal carboration.

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Octane RatingOctane Rating(R+M)/2

M - MON - MON testing uses a similar test engine to that used in RON testing, but with a preheated fuel mixture, a higher engine speed, and variable ignition timing to further stress the fuel's knock resistance. Depending on the composition of the fuel, the MON of a modern gasoline will be about 8 to 10 points lower than the RON.

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Octane RatingOctane Rating

(R+M)/2engine is operated under test conditionsdegree of knocking determinedfuel is then blended from n-heptane and

isooctane to duplicate conditionspercentages measured, 87% isooctane, 87

octane gasoline

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Oxygenated & Reformulated Oxygenated & Reformulated GasolinesGasolines

Oxygenated Gasolines – gasoline blends with organic compunds that contain oxygen, such as MTBE, methanol, ethanol, and tert-butyl alcohol

Reformulated Gasolines – oxygenated gasolines that contain lower percentage of aromatic hydrocarbons and have a lower volatility than ordinary gasoline

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Catalytic CrackingCatalytic Cracking

A process that uses a catalyst, heat, and pressure to break long-chain hydrocarbons into shorter-chain hydrocarbons including both alkanes and alkenes, many in the gasoline boiling point range

Alkenes have higher octane numbers than corresponding alkanes

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EthyleneEthylene

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Addition PolymerAddition Polymerpolymer formed by joining many molecules

of the same compound to form the large molecule

The compound usually contains a carbon-carbon double bond

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Condensation PolymerCondensation Polymerpolymer formed by molecules of two

different compounds joining to form the large molecule

one compound usually has an amine functional group

other molecule has carboxylic acid functional group

split out water molecule to form peptide linkage

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Uses for Plastic ContainersUses for Plastic Containers

Soft-drink bottles, most commonly recycled plastic

Milk, juice and water jugs. Recycled HDPE used as trash containers, drainage pipes, garbage bags, and fencing. Second most commonly recycled plastic.

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Uses for Plastic ContainersUses for Plastic Containers

vinyl siding, magnetic stripe cards, window profiles, gramophone records (which is the source of the term vinyl records), insultation on electrical wire, pipe, plumbing and conduit fixtures.

various containers, dispensing bottles, wash bottles, tubing, plastic bags for computer components, and various molded laboratory equipment. Its most common use is in plastic bags

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Plastic ContainersPlastic Containers

food packaging, ropes, textiles, stationery, plastic parts and reusable containers of various types, laboratory equipment, loudspeakers, automotive components, and polymer banknotes

plastic model assembly kits, license plate frames, plastic cutlery,CD "jewel" cases

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Plastic ContainersPlastic Containers

Container manufactured using a blend of plastics, eg two or moreplastics (PET and any other polymer), the container should beidentified 7.

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Polyethylene terephthalatePolyethylene terephthalate (aka (aka PETPET) )

+

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PolyethylenePolyethylene

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PolyethylenePolyethylene

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Polyvinyl ChloridePolyvinyl Chloride

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PolypropylenePolypropylene

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PolystyrenePolystyrene

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Benzene-AromaticityBenzene-Aromaticity

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TolueneToluene

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2,4,6-Trinitrotoluene2,4,6-Trinitrotoluene

NO2

NO2

O2NHNO3

H2SO4

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Mr. Watson HST

Alcohols and Carboxylic AcidsAlcohols and Carboxylic Acids

Alcohol R’-O-H

O

Carboxylic acid R-C-O-H

O

Ester R-C-O- R’

where R & R’=> alkyl group => CH3-(CH2)n-

n = 0, 1, 2, 3, etc

==

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Triglycerides – Fats and Oils Triglycerides – Fats and Oils SoapSoap

O

CH2-O-C-R

O

CH -O-C-R’

O

CH2-O-C-R”

==

=

OCH2-O-H Na-O-C-R

OCH -O-H Na-O-C-R’

OCH2-O-H Na-O-C-R”

==

=

NaOH

heat

fat or oil glycerol fatty acid salts

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Triglycerides – Fats and Oils Triglycerides – Fats and Oils BiodieselBiodiesel

O

CH2-O-C-R

O

CH -O-C-R’

O

CH2-O-C-R”

==

=CH2-O-H CH -O-HCH2-O-H3 CH3OH

heat

fat or oil

glycerol

methyl estersbiodiesel

OCH3-O-C-R =

OCH3-O-C-R’=

OCH3-O-C-R”=

+

+

+

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Triglycerides – Fats, SaturatedTriglycerides – Fats, Saturated

O

CH2-O-C-C7H15

O

CH -O-C-C7H15

O

CH2-O-C-C7H15=

==

saturated – fat - solid

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Triglycerides – Oils, UnsaturatedTriglycerides – Oils, Unsaturated O

CH2-O-C-(CH2)nCH=CH(CH2)nCH3

OCH -O-C- (CH2)nCH=CH(CH2)nCH3

OCH2-O-C- (CH2)nCH=CH(CH2)nCH3

==

=

unsaturated – oil - liquid

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NitroglycerinNitroglycerin

CH2-O-HCH -O-HCH2-O-H-

- HNO3

CH2-NO2

CH –NO2

CH2-NO2--

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CholesterolCholesterol

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AlcoholsAlcohols

Methanol – CH3OH

Ethanol – CH3CH2OH

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EthanolEthanol

CH3CH2OH CH2=CH2 + H2

ethanol catalyst ethylene

Important in 1970-1990s for plastic production

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SugarsSugars

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EthanolEthanol

C6H12O6 3 CH3CH2OH

glucose enzyme ethanol

unbalanced

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StarchStarch(C6H12O6)n 3n CH3CH2OH

starch enzyme ethanol

corn

unbalancedImportant in 21st century as source of fuel

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Synthetic RubberSynthetic Rubber

1,3-Butadiene

= =n ( )n=

butadiene rubber

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Synthetic RubberSynthetic Rubber

vulcanization

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Neoprene RubberNeoprene Rubber

SCl2

n

= =

= =

sss

s

sss

s

Cl

Cl

Cl

Cl

Cl

Cl

ss

s

s

Cl

Cl