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Industrial Chemistry > The organic side > Flashcards

The organic side Flashcards

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1
Q

What is the limit of sulfur content found in Canadian gasoline?

A

40ppm

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2
Q

The majority of refined petroleum is used in?

A

Motor gasoline

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3
Q

What are the 3 rules for predicting octane number?

A
  1. Higher branching or amount of rings gives higher octane number
  2. Increasing multiple bonds increases octane number
  3. aromatics, alkenes, alkynes > cyclic and branched alkanes > straight chain alkanes
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4
Q

Combustion is a what type of reaction?

A

A radical reaction

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5
Q

What are the three main steps used to increase and refine petroleum?

A
  1. Hydrotreating
  2. Catalytic cracking or thermal cracking
  3. Catalytic reforming
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6
Q

What happens in ‘hydrotreating’? What catalyst does hydrotreating use?

A

In hydrotreating, the amount of sulfur and nitrogen gets reduced - however a reduction in octane number for some of the hydrocarbons cannot be prevented.
The catalyst used in hydrotreating is cobalt or nickel oxide over molybdenum catalyst.

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7
Q

What does catalytic cracking do? What is the catalyst used in catalytic cracking?

A

Catalytic cracking breaks down long hydrocarbon chains into smaller ones. Hydrocarbons also rearrange due to their differences in radical stabilities. Catalytic cracking uses a silica - alumina catalyst (SiO2 - Al2O23)

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8
Q

What is the difference between catalytic and thermal cracking?

A

Thermal cracking does not involve a catalyst, but gives a higher yield of C2, C3 & C4 olefins (and BTX) - these chemicals are needed in the chemical industry. ‘Beta - scissons’ occur in thermal cracking - and produces ethane.

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9
Q

What happens in catalytic reforming and what catalyst does catalytic reforming use?

A

Catalytic reforming increases the amount of double bonds in a hydrocarbon without changing the amount of carbons - this is done by 1,2 methyl and 1,2 H shifts. The catalyst used in catalytic reforming is platinum and/or rhenium (Re) on alumina.

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10
Q

What acts as the Lewis acid in catalytic reforming?

A

The alumina.

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11
Q

Where can we find methane?

A

97% of methane is in natural gas and 85% is in ‘typical’ natural gas

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12
Q

What are the 4 steps when refining methane?

A
  1. Dehydration
  2. Elimination of hydrogen sulfide and carbon dioxide
  3. Dissolution of the higher boiling point gas
  4. Fractional distillation which separates out the methane, ethane, propane, n - butane and isobutane
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13
Q

How is ethylene made?

A

By thermal cracking (thermal cracking requires no catalyst).

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14
Q

During the synthesis of ethylene, what is used to inhibit “coking” (coal forming) and to increase the amount of ethylene made?

A

Steam.

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15
Q

What is the main use of ethylene? Name two other polymers made from ethylene.

A

To make polyethylene - a plastic. Polyvinyl - chloride and styrene.

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16
Q

What is the main and minor way that propylene is made?

A

The main way propylene is made is by thermal cracking. The minor way pure propylene is made is by steam cracking - which is used in chemical manufacture.

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17
Q

What is propylene mainly used for? Name two other chemicals made from propylene.

A

To make polypropylene - a plastic used in films, containers, packaging, etc. Acrylonitrile and cumene.

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18
Q

C4 composition #1, 3 butadiene. What are the two steps in making 1,3 butadiene?

A
  1. Dehydrogenation

2. Extraction distillation

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19
Q

What is the catalyst used in the dehydrogenation step when making 1, 3 butadiene?

A

Fe2O3

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20
Q

How does 1, 3 butadiene get extracted in the ‘extraction distillation’ steps (3 steps)?

A
  1. The crude mixture is extracted with acetone since the pi bonds are more polar than the saturated hydrocarbons (gets rid of butane).
  2. A non volatile solvent that mixes well with 1, 3 butadiene is added to change the volatility of 1, 3 butadiene.
  3. 1, 3 butadiene is then extracted by conventional distillation.
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21
Q

What is the main use of 1,3 butadiene?

A

To make styrene - butadiene rubber.

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22
Q

What is the main use of isobutylene?

A

For alkylation or polymerization of gasoline.

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23
Q

Why are there 2 ways of forming isobutylene?

A

The first way just makes isobutylene and the second way makes isobutylene and gives off useful side products. < be able to draw out those two reactions>

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24
Q

What does BTX stand for?

A

Benzene, toluene and xylene.

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25
Q

How is benzene made?

A

Benzene is made by catalytic reforming of naphtha (naphthalene); naphtha is a flammable oil that contains various of hydrocarbons.

26
Q

What is the catalyst use in catalytic reforming for benzene? What is the catalyst called

A

3 to 6mm pellets of platinum catalyst. The ‘platforming process’.

27
Q

During the catalytic reforming of benzene, what gas gets re - used and what is it called?

A

Hydrogen gas gets re - used and it is called the ‘reforming gas’.

28
Q

In the catalytic reforming process of benzene, what does the ‘Udex extraction’ do?

A

The ‘Udex extraction’ separates out the non - aromatic components from the aromatic compounds via a liquid - liquid extraction technique.

29
Q

When forming benzene, sometimes toluene is formed. What is the reaction and catalyst used to convert toluene back into benzene?

A

Toluene is reacted with hydrogen gas with chromium (Cr), molybdenum (Mo) or cobalt oxides on alumina (Al2O3) catalyst to get back benzene and methane as a side product.

30
Q

What is benzene mainly used for?

A

Benzene is mainly used to make ethylbenzene (ethylbenzene is then used to make styrene).

31
Q

How does para xylene get separated out from othro and meta xylene?

A

By cooling down the mixture to turn para xylene into a solid - this is possible since they all have different melting and boiling points.

32
Q

What does para xylene turned into?

A

Para xylene is turned into dimethyl terephthalate which then gets turned into a polymer (polyester aka PET)

33
Q

What is ortho xylene turned into?

A

Phthalic anhydride (used to make plastic more flexible)

34
Q

What is ethylene dichloride mainly turned into?

A

Vinyl chloride

35
Q

What are the two types of catalyst used to make ethylene dichloride (2 different reaction that uses different catalyst but both make ethylene dichloride)

A
  1. Iron (III) chloride catalyst with chlorine gas

2. Copper (II) chloride catalyst in the presence of oxygen gas and HCl (‘oxyochlorination’)

36
Q

What is vinyl chloride mainly turned into?

A

Polyvinyl chloride

37
Q

How is vinyl chloride form and what catalyst does it use?

A

Vinyl chloride is formed by thermal dehydrochlorination (forms HCl) of ethylene dichloride and it uses a charcoal catalyst

38
Q

What is acetic acid mainly turned into?

A

To make vinyl acetate (a polymer)

39
Q

What are the 4 different ways to form acetic acid?

A
  1. methanol carbonylation
  2. acetaldehyde oxidation
  3. using butane from the C4 fraction
  4. fermentation (from bugs)
40
Q

What type of processes is used in methanol carbonylation and what are the 2 catalyst used?
Which process is ‘greener’?

A

The Monsato and the Cativa process, The catalyst used in the Monsato process is a rhodium catalyst (think Wilkinson’s). The catalyst used in the Cativa process is iridium catalyst. The greener process is the Cativa process

41
Q

What process is used in the acetaldehyde oxidation and what are the 2 steps to form acetic acid? What catalyst is used in the acetaldehyde oxidation?

A

The Wacker process is used. The two steps to form acetic acid are formation of an acetaldehyde and then oxidizing the acetaldehyde to form acetic acid. The catalyst used is palladium dichloride and copper chloride

42
Q

When using butane from the C4 stream to make acetic acid, what is the catalyst used?

A

Cobalt (the best), manganese or chromium acetates catalyst

43
Q

What is the main use of vinyl acetate? What catalyst forms vinyl acetate?

A

To make poly - vinyl acetate (used in water - based adhesives, coatings and paints). Wacker’s catalyst (PdCl2 and CuCl).

44
Q

What are the 3 catalysts used to make POLY - vinylacetate?

A
  1. C-PdCl2 - CuCl2
  2. PdCl2 - Al2O3
  3. Pd-C, KOAc
45
Q

What is ethyl bezene mainly turned into?

A

Styrene

46
Q

How is ethyl benzene made?

A

By Friedel Crafts alkylation

47
Q

In the synthesis of ethyl benzene what is the catalyst used in vapor phase? In gas phase?

A

In vapor phase, the catalyst that is used are boron triflouride, phosphoric acid or alumina - silica. In gas phase the catalyst that is used is a Mobil - Badger zeolite catalyst

48
Q

What is styrene mainly turned into?

A

Polystryene (used in toys, bottles, jars, cushion foams)

49
Q

What are the steps in making styrene?

A
  1. Ethyl benzene gets oxidized
  2. The oxidized ethyl benzene is then reacted with propylene to form MBA
  3. MBA is then dehydrated with acidic silica gel or titanium dioxide to form styrene
50
Q

What is ethylene oxide mainly used for?

A

To make ethylene glycol

51
Q

What catalyst is used to make ethylene oxide?

A

A silver over silver oxide catalyst (oxidizes ethane)

52
Q

What is ethylene glycol mainly used to make?

A

Polyester fiber or antifreeze

53
Q

What condition are required to form ethylene glycol?

A

Acidic conditions; it uses a 0.5 to 1% H2SO4 catalyst)

54
Q

What is acrylonitrile mainly used for?

A

Acrylonitrile is mainly used for adiponitrile (which is used to make nylon).

55
Q

What are the reactants and what is the catalyst used to make acrylonitrile?

A

The reactants are ammonia, propylene and oxygen gas. The catalyst use is Bi2O3 . nMoO3

56
Q

Propylene oxide is mainly turned into?

A

Polypropylene glycol

57
Q

What are the two ways to make propylene oxide?

A
  1. Chlorohydrin formation (uses propylene, chlorine and water)
  2. The Halcon process (oxidizes isobutene over a molybdenum naphthenate catalyst to form BHP; BHP then reacts with propylene to get propylene oxide)
58
Q

What is cumene mainly turned into?

A

Phenol and acetone

59
Q

What is the type of reaction to form cumene and what are the reactants?

A

The reaction to form cumene is a Fiedel Craft reaction. The reactants are benzene and propylene

60
Q

What are the catalyst used to make cumene?

A

Zeolites or solid phosphoric acid

61
Q

What is acetone mainly turned into?

A

Acetone-cyano-hydrin

62
Q

What is the major and minor way to form acetone?

A

The major way is by using cumene and the minor way is by using cumene

Industrial Chemistry (1 decks)

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