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Industrial Organic Chemistry and Catalysis, second half > Industrial Perspective > Flashcards

Industrial Perspective Flashcards

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1
Q

What are the five important processes used in an oil refinery to produce useful fuels and other olefins from crude oil?

A

1) Hydrotreatment
2) Catalytic Reforming
3) Cracking
4) Hydrocracking
5) Fluid Catalytic Cracking

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2
Q

What are the purposes of Hydrotreatment?

A

To remove sulfure and oxygen impurities since these might inhibit catalysts for other processes, as well as preventing SO2 emissions (harmful)

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3
Q

What are the starting materials, conditions and products of hydro treatment?

A

Ring structures (aromatic) i.e. containing sulfur react in the presence of a MoS catalyst in 300-400*C to hydrocarbon degrees with varying degrees of unsaturation (i.e. butane, butene, and butadiene)

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4
Q

What is the purpose of Catalytic Reforming?

A

To produce more branched alkane structures, and thus raise the octane numbers of the starting materials without affecting their enthalpy of combustion.

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5
Q

Why are high octane numbers preferable?

A

High octane numbers are an indicator that the respective fuel is less likely to cause knocking aka less likely to auto ignite under high pressure. This happens since the branching prevents stronger stacking.

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6
Q

What is the catalyst in Catalytic Reforming and how does it create branched alkanes (short explanation)

A

The catalyst is a Zeolite Brønsted acid with Pt present. The Pt abstracts a hydride, after which hydride shifts and methyl shifts move around a carbocation to produce the most branched molecule possible before the hydride is reattached (can be stopped at different stages in the process -> many products possible)

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7
Q

What is the purpose of cracking and hydrocracking.

A

To produce shorter carbohydrates from longer chains.

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8
Q

What is the key differences between cracking and hydrocracking?

A

While cracking produces alkenes, hydrocracking contains a second step in which the alkene is hydrogenated over Pd/C to produce alkanes.

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9
Q

What is the catalyst for cracking and the first step of hydrocracking?

A

The catalyst is a radical initiator under high temperatures. It is able to abstract a hydrogen in the initiation step, leaving a carbon radical. This radical electron then combines with an electron on a beta bond to form a pi bond over the existing alpha single bond, simultaneously allowing the second beta electron to form a new radical, and so on. Termination can occur in many ways, i.e. by forming a bond between a radical H and a radical C. The double bond formation process is not position-selective.

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10
Q

Both tertiary carbocations and radicals are more stable than their primary counterparts. Then why are the cracking process not position selective while catalytic reforming is?

A

The relative stability of tertiary carbocations is much stronger than that of the radical, which does not factor into stability anywhere near as strongly. Hence, the carbocation facilitated process of reforming will be more position selective than the radical-based cracking.

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11
Q

What are the two main types of feedstock?

A

Fossil (oil, coal, gas, minerals) and renewables (biomass, air, water)

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12
Q

How is acetylene (ethyne) produced industrially?

A

Calcium carbide (produced from calcium oxide and carbon) reacts with water to form acetylene and calcium hydroxide.

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13
Q

What is the purpose of fluid catalytic cracking?

A

To produce smaller carbohydrates with high octane numbers (branched or aromatic). Essentially, it is a combination of cracking and reforming.

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14
Q

Which catalyst is used in fluid catalytic cracking?

A

Zeolite acid with noble metals at high temperature (v. similar to reforming)

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15
Q

What is the main production pathway of making hydrogen?

A

Steam methane reforming: CH4 + H20 -> CO + 3H2

Alternatively, there is also autothermal methane reforming which proceeds via oxygen and carbon dioxide at high temp.s

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16
Q

How can we produce syngas (hydrogen and carbon monoxide) from coal?

A

Coal gasification: Carbon is reacted with oxygen in the presence of air.

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17
Q

How is ammonia produced industrially?

A

Ammonia is produced via the Haber-Bosch process (largest hydrogen user in industry): 3H2 + N2 -> 2NH3

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18
Q

What are ammonia’s uses in industry?

A

NH3 can be used to produce HCN via the Andrussow oxidation (methane and oxygen gas) or the Degussa process (methane) at high temp.s in the presence of Pt. Furthermore, it is used to produce nitric acid (a fertilizer) or hydrazine (rocket fuel)

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19
Q

What are the building blocks of the following polymers? PVC (polyvinyl chloride), polystyrene, PET (polyethylene terephlate)

A

choroethene (ethene), styrene (ethene and benzene, ethylene glycol and para di benzoic acid

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20
Q

How can we convert syngas to hydrocarbon fuels? - one step route

A

Via the Fischer Tropsch process which occurs at high pressures in the presence of an Fe or Co catalyst.

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21
Q

How can we convert syngas to hydrocarbon fuels? - three step route

A

First by producing methanol from syngas in the presence of a metal catalyst, high pressure and high temp. Then by proceeding to react methanol to dimethyl ether (DME) over a zeolite acid, which is then used to make a long hydrocarbon.

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22
Q

What are the three significant processes carbon feedstocks undergo and what do they produce?

A

1) gasification to produce syngas
2) liquefaction to produce liquid fuels
3) pyrolysis to produce liquid or solid fuels or coke

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23
Q

What is the most commonly known type of catalytic cracking?

A

Steam cracking: produces small building blocks such as ethene, propene, benzene, etc. from naphtha via the common cracking mechanism in the presence of steam.

24
Q

What is the purpose of the Shell higher olefin process?

A

To polymerise ethene into long alkenes (whatever the desired olefin is)

25
Q

What are the five steps of the SHOP and what do they mean?

A

1) Oligomerization: producing long chains from ethene (with high pressure and a nickel catalyst)
2) separation: finished olefins go on while the nickel catalyst is recycled
3) distillation: chains that are too short are distilled off.
4) Isomerization: terminal alkenes are turned into non-terminal alkenes.
5) Metathesis: used to produce the desired olefin: the product of step 4) is reacted with a short alkene, where the R-groups switch around.

26
Q

What are useful products of the SHOP?

A
  • Butylene to make PBT
  • substrates for synthetic esters
  • alcohols for the production of PVC Plasticisers
  • higher olefins (longer chains of 11 to 14 carbons)
27
Q

What is the purpose of PVC plasticisers?

A

Plasticisers are larger molecules containing phenyl and ester groups which are added to the otherwise very hard and brittle polyvinyl chloride plastic to make it softer and malleable.

28
Q

What is an alternative way to Fischer-Tropsch of making 1-hexene and 1-octene?

A

Alkene tri- and tetramerization from ethene in the presence of a metal catalyst.

29
Q

How can we industrially make aldehydes?

A

Hydroformulation

30
Q

What are the substrates and catalyst of hydroformulation?

A

a terminal alkene along with CO and H2 from syngas can react in the presence of a homogeneous Co or Rh catalyst to an aldehyde.

31
Q

Why is hydro formulation such a relevant reaction for industry?

A
  • Both starting materials easy to come by (syngas and an alkene)
  • The product can be used in many applications: red/ox reactions to alcohols or carboxylic acids, aldol condensations, immune formation, acetal formation, alkylation
32
Q

What are the ways with which we can make epoxides and why are some more preferable?

A

1) reacting alkenes with HOCl -> not great since this produces HCl
2) organic peroxides -> peroxides are corrosive
OPTIMAL
3) with oxygen (only works for ethene, not for propene due to the possibility of side products)

33
Q

From which feedstock do we produce multi carbon building blocks such as ethene, propene, benzene, toluene, butadiene, etc.?

A

crude oil

34
Q

From which feedstock do we produce syngas?

A

natural gas and coal

35
Q

From which feedstock do we produce methanol?

A

syngas (natural gas and coal) and coal.

36
Q

From which compounds do we commercially make polyesters (general answer)

A

Diacids and Diols

37
Q

What is the difference between nylon 6,6 and nylon 6?

A

Their building blocks:
nylon 6,6 : 6C diamine and hexanoic acid
nylon 6: 7-membered amide ring

38
Q

From which starting materials can we produce diamines?

A

i.e. butadiene and HCN (gets hydrogenated)

39
Q

If butadiene is chlorinated to yield a terminal alkene instead of a non-terminal (which forms a diamine), what is the product after Hal elimination?

A

neoprene

40
Q

What are the starting materials and products of the Wacker oxidation?

A

Starting materials: alkene, oxygen, Pd/Cu catalyst
Product: aldehyde or ketone

41
Q

What are the starting materials and products of epoxidation?

A

starting materials: alkene, peroxide/oxygen/HOCl
Product: epoxide

42
Q

What are the similarities and differences between the Wacker oxidation and an epoxidation?

A

Similarites: both use alkenes (i.e. ethene and propylene) and possibly oxygen as starting materials.
Differences: the hacker oxidation produces carbonyl compounds, while epoxidations produce epoxides.

43
Q

What is the difference in products of a nucleophilic single-substituted epoxide opening in the presence of an acid or a base?

A

Acid: the alcohol is terminal
Base: the nucleophile is terminal

44
Q

What is the difference between the two ways of producing HCN?

A

Andrussow oxidation uses NH3, CH4 and O2 whereas Degauss does not use O2

45
Q

What is polyacrylonitrile a precursor to?

A

Carbon fibre

46
Q

What can be made from poly acrylic acid?

A

diapers

47
Q

What can be made from polystyrene?

A

Plastic cups

48
Q

What can be made from nylon?

A

stockings

49
Q

Adiponitrile is the thermodynamic product of the chlorination of butadiene. What is the ultimate kinetic product (after another couple of steps?)

A

neoprene

50
Q

What is poly vinyl acetate used to make?

A

Paint, cheese rind, etc

51
Q

What are the building blocks of epoxy resin?

A

benzene, propylene, and carbon monoxide

52
Q

Describe the steps via which we can produce bisphenol A:

A

1) alkylation of benzene with propylene to form cumene
2) oxidation to propanone and phenol
3) dehydration condensation to bisphenol A

53
Q

What are the steps of the classical production of MMA?

A

1) benzene and propylene to cumene
2) oxidation to propanone and phenol
3) propanone attacked by -CN
4) reduced MMA except instead of OMe, NH3+
5) nucleophilic substitution by methanoate

54
Q

Which common material is MMA the building block of?

A

plexiglas

55
Q
A

Industrial Organic Chemistry and Catalysis, second half (1 decks)

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