Design and Analysis of Process Systems

Project 1

Technology Assessment: Fuel Oxygenates

Due Date: 02/10/20

 Abstract

In this report, we were tasked with performing a technology assessment of fuel

oxygenates. The assessment included the analysis of fuel oxygenate characteristics, benefits, and
performances, as well as the manufacturing processes of the two major fuel, oxygenates,
bioethanol and Methyl Tertiary Butyl Ether (MTBE). MTBE is commonly produced to be used
as a fuel oxygenate by petrochemical companies. It was used as a replacement for metal-based
anti-knocking agents until it was found to be an environmental and health hazard. Eventually,
MTBE was determined to be an environmental hazard, so today ethanol is now the most widely-
used biofuel oxygenate. While ethanol is made from corn, MTBE is the product of an exothermic
reaction between methanol and butylenes under catalytic conditions.
In gasoline blends, using an oxygenate content greater than 10% has been shown to substantially
increase octane rating in the fuel. It allows for more complete combustion, which keeps the
engine cleaner and prolongs the life of the engine. The main disadvantages of these two
oxygenates are the negative environmental and health implications and the impracticality of
worldwide implementation. Bioethanol is incredibly expensive to produce when the cost of
production of corn feedstock is factored in, and MTBE is highly toxic and can easily contaminate
groundwater due to their miscibility.
The rest of this paper covers the product specifications for both MTBE and bioethanol, as
well as the reaction pathways for their synthesis and flow sheets for large scale commercial
production.

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Introduction

Fuel is utilized in multiple industries and systems worldwide, unfortunately, the exhaust from
fuel systems is usually toxic and harmful to the surrounding environment and conventional fuels
don’t yield maximum efficiency. Due to the exponential increase in the demand for fuel, the use
of fuel oxygenates is increasingly important, in order to reduce environmental pollution, improve
fuel efficiency and reduce operating costs. Fuel oxygenates are oxygen-containing compounds,
mainly ethers, and alcohols, which are added to fuels such as gasoline in order to increase their
octane numbers. Increasing the octane number of fuel reduces the compression ratio for the
gasoline combustion thus promoting more complete combustion.
Tetra alkyl lead components used to be used as octane enhancers, however, in the 1990s, lead
was removed from gasoline due to the severe health and environmental concerns associated with
‘leaded fuel’[1]. The removal of lead from motor gasoline led to the significant lowering of the
octane number of the fuels and oxygenates were introduced in a bid to offset this loss.
In the USA, a Clean Air Act was established that required oxygenates to be used to enforce
emission control and reduce the carbon monoxide emission. Oxygenates play a vital role in the
reduction of toxic, hazardous emissions. The high oxygen content aids in the complete
combustion of the hydrocarbon fuel which reduces hazardous waste in the fuel system exhaust.
In this report, we were tasked with performing a technology assessment of fuel oxygenates. The
assessment included the analysis of fuel oxygenate characteristics, benefits, and performances, as
well as the manufacturing processes of the two major fuel, oxygenates, bioethanol and MTBE.

There are a number of different oxygenates (Table 1&2) that can be used as fuel components to
increase the octane number. Figure 1 below shows some of the chemical structures of the
oxygenates.

Figure 1: Chemical structures of oxygenates [2]

Properties of fuel oxygenates

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The fuel properties of oxygenates vary significantly with length and type of alkyl chains.
Oxygenates with higher molecular weight often have higher density, higher boiling point, higher
viscosity, lower volatility, and lower flammability than respective candidates with lower
molecular weight. Therefore, they are better suited to be used as diesel fuel components.

Below are some of the physical and chemical properties of some common fuel oxygenates i.e
ethers and alcohols.

Table 1: Physical and chemical properties of ethers [2]

Table 2: Physical and chemical properties of alcohols [2]

Other chemical and physical characteristics [3] to consider when assessing fuel oxygenates, since
they may contribute to the overall functioning of the fuel and may pose certain constraints,
include:
● Miscibility of different compounds depends on a number of different properties for
example density and polarity of the individual compounds. The densities of the
oxygenates proportionally affect the densities of the fuel blends and a low-density fuel
leads to reduced power output and higher fuel consumption. Oxygenates are usually polar
compounds whereas hydrocarbon fuels are non-polar compounds, this variance in

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 polarity makes some oxygenates easier to blend with fuels than others. For the less polar
oxygenates, additives are usually necessary to complete the blending process.
● Hygroscopy; this refers to the affinity of a substance to water. The polar nature of
oxygenates makes it such that oxygenates easily absorb water present in their surrounding
environments. Ethanol, for example, is water-soluble and therefore carries moisture into
the fuel system. The solubility of hydrocarbons reduces with the reduction of temperature
and increase of water in the system, this increases the chances of phase separation which
destroys the fuel. Water also reduces the energy content of the fuel and free water
freezes at low temperatures.
● The viscosity of fuel influences the quality of its combustion, therefore, using fuel of the
right viscosity is important to the proper functioning of the fuel system. Low viscosities
cause leaks and delays in the system and high viscosities increase the load and power
needed by the system.
● Reid Vapor Pressure (RVP) is a measure of volatility and is defined as the pressure at
which a hydrocarbon liquid will begin to flash to vapor under specific conditions. Figure
2 shows the effect of various oxygenates on the RVP. The addition of oxygenates causes
an increase in the vapor pressure of the fuel and a consequent reduction in the boiling
point temperature. Since RVP defines the evaporation characteristics of the fuel, higher
values of RVP are correlated with increased emission therefore oxygenates can lead to
hazardous environmental consequences.

Figure 2: The effect of oxygenates on vapor pressure [1]

Benefits of fuel oxygenates

The major benefit of fuel oxygenates is the role they play in the reduction of fuel emissions from
fuel systems. Exhaust from diesel engines produces a lot of air pollution such as carbon

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monoxide, unburned hydrocarbons (HC), oxides of Nitrogen (NOx) and Particulate matter (PM)
emissions. Fuel oxygenates aid in the complete combustion of the fuel which minimizes the
amount of toxic hazardous waste released to the environment. Hydrocarbon and Carbon
monoxide emissions are produced from incomplete/partial oxidations, the higher oxygen
quantity and higher cetane number reduce both these emissions.
NOx emissions are considered one of the most dangerous emissions. The oxygen supports the
burning of the fuel while emitting very low levels of inert materials e.g. Nitrogen, this reduces
the number of toxic NOx emissions.
Particulate Matter (PM) are solid and liquid particles suspended in the air such as soot. It can be
shown experimentally that particulate matter can be significantly reduced by adding oxygenated
species to fuels. Using Bosch smoke number, it is seen that the measure of particulate/ soot level
in diesel exhaust falls from about 55% for conventional diesel fuel to less than 1% when the
oxygen content of the fuel is above 25 - 30 % by mass [2].
A number of mechanisms are proposed to explain the reduction of PM due to fuel oxygenates but
generally oxidizing agents are suppressing soot early in the nucleation process and reduce its
peak production. The presence of oxygen also leads to the reduction of ethylene production,
which is often considered a precursor of soot and PAH, this decreases the formation of soot.

Figure 4: Smoke emissions from diesel engines [4]

Other benefits include increasing the power of the fuel system and thus the efficiency of the
overall system.

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Fuel oxygenate alcohols and ethers performance, advantages, disadvantages, factors
affecting adoption:

Commercial gasoline is given octane rating, such as 87, which indicates that the fuel is
either 87% octane, or it contains a combination of additives and fuel that produces the same
compression ratio as an 87/13 octane and heptane blend without spontaneously igniting under
compression – thus preventing knock. To get a better understanding of the performance of
oxygenates in fuel, octane numbers need to be further explored.

To properly illustrate the anti-knock abilities of gasoline additives, two octane numbers
are used: Research Octane Number (RON) and Motor Octane Number (MON). These numbers
describe the performance of gasoline combustion engines using oxygenates under different
conditions (acceleration, constant speed, etc). According to recent studies, the Research Octane
Number is slightly more important in newer cars. It has been shown that actually lowering the
Motor Octane Number specification would actually improve vehicle performance. This not only
helps the consumer save wear and tear on their vehicle, but it also makes the refinery process a
little bit easier and less expensive.

In 2016, a group of European researchers from gas companies created a “fuel matrix” that
allowed them to track and test the effectiveness and performance of oxygenates as fuel additives.
In their research, they tested gasoline/ethanol as well gasoline/ETBE (Ethyl Tertiary Butyl Ether)
blends and compared the results, which are shown in the table below. The fuels with the highest
octane ratings had oxygenate contents of 20% and over. It is obvious from their findings that
gasoline without any oxygenate additives have noticeably lower Research Octane Numbers and
Motor Octane Numbers. They also found that increasing the RON appears to provide a larger
boost to acceleration and engine power. [5]

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Despite being able to increase the octane number of gasoline, the
metal-based antiknock fuel additives, such as tetra-ethyl lead, had
a plethora of disadvantages (i.e. lead toxicity), which is why they
are no longer used outside of certain types of aviation fuel. Today,
most gasoline additives that are used to increase octane ratings are
organic chemicals. These typically consist of alcohols and ethers,
as well as some aromatic compounds. The most immediate
advantage of using oxygenates in fuel is the obvious boost in
octane – the higher the octane number, the
better it burns. They prevent knocking and
allow for much cleaner, full burning – no ash is formed [6]. Some
oxygenates, like methanol, are incredibly inexpensive to produce. Others,
like MTBE, are significantly more expensive. One disadvantage to using
oxygenates is the needed use of solvents to properly blend them with
gasoline. Benzene, a solvent used in conjunction with oxygenates, is
highly toxic and has been shown to cause cancer. Another major
disadvantage of these compounds is the volume required to boost octane
numbers. As shown in the table below, up to 15% of the fuel by volume needs to be oxygenated
and up to 35% aromatic solvents [6]. Unfortunately, the now-banned tetra-ethyl lead was only
needed in very small amounts (< 100 ppm) to give fuel the needed octane boost.

During World War II, the United States divided itself into five different economic regions
to help better allocate gasoline and diesel, as well as track and organize the other various
petroleum products being used across the county. These regions are known as Petroleum
Administration for Defense Districts or PADDs. In the figures below, it is shown across all five
PADDs how little gasoline is actually mixed with oxygenates.

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 According to researchers at the Department of Energy, during winter months, oxygenated
gasoline makes up only about 5 percent of the gasoline sold. Overall, the yearly average tops out
at a measly 1.3 percent. (eia.gov/outlooks/steo/special/pdf/mtbe.pdf)
The largest factors affecting the adoption of oxygenates into all reformulated gasoline are
the cost, scope, and impracticality. That large of a change would undoubtedly be a long and
expensive implementation, but the U.S. government is slowly trying to find ways to make it
happen. One of the main things being done is finding ways of reducing the cost of growing and
converting biomass feedstocks into ethanol. USDA is actively focusing primarily on reducing the
cost of growing and converting agricultural feedstocks, such as corn, into ethanol. Some
researchers believe that these attempts are futile and that using ethanol from corn as fuel is
unsustainable and impractical. According to David Pimentel, a Cornell professor in the College
of Agriculture and Life Sciences, roughly 131,000 BTUs are used to make a single gallon of
ethanol. One gallon of ethanol contains only about 77,000 BTU of energy, meaning 70% more
energy is needed to produce ethanol than what is actually contained in it – a net energy loss of
54,000 BTU [7]. Additionally, the cost of ethanol production lies entirely on crop seasons. If
farmers have a bad year and there is a corn shortage, the cost of ethanol will skyrocket, and it has
before as shown in the graph below. This level of instability will always be a significant concern.

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 Another significant concern over the mass implementation of oxygenates is the potential
for water supply contamination. While ethanol isn’t directly harmful in small amounts, other
oxygenates such as ethers can be incredibly damaging to not only the environment, but to
humans as well. Groundwater can become tainted in the event of a gasoline spill, and since
oxygenates are soluble in water, it becomes a difficult challenge to separate the two. Studies
have shown that long-term exposure to oxygenates such as MTBE causes cancer in laboratory
animals, as well as cause severe adverse effects on the liver, kidney and central nervous system
[8].

Fuel oxygenate raw materials and costs of production:

MTBE, which used to be one of the most commonly used oxygenates, is relatively
inexpensive to produce. There are currently three types of MTBE production plants: refineries
and petrochemical plants, TBA plants, and merchant plants. Refineries and petrochemical plants
use isobutylene, a byproduct from refinery crackers, as the feed stock for MTBE [9]. It is reacted
with methanol to produce MTBE and costs roughly $2.14 per gallon to make [10].

Merchant plants start with n-butane as feedstock and isomerize it to isobutane. From
there, the isobutane is dehydrogenated and converted to isobutylene, which is then in turn reacted
with methanol to give MTBE. The cost of production in these plants is significantly high, mostly
due to the additional isomerization and dehydrogenation steps. Merchant plants cost $20,000 to
$28,000 per daily barrel of capacity.

The smallest source of MTBE production comes from TBA plants, as there are only two
chemical plants in the United States that currently use this process. Tertiary butyl alcohol is a
leftover byproduct from the production of propylene oxide. This TBA is simply reacted with
methanol to give MTBE [9].

Ethanol and other alcohols are currently among the most commonly added oxygenates.
Ethanol is produced mainly from corn and costs roughly $1.57 per gallon to make, which is
compared with about $1.75 to produce a gallon of gasoline [10]. And this doesn’t even take into

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consideration the growing costs, let alone environmental ones. Pimentel noted that an acre of
planted corn will yield roughly 7,110 pounds of processable corn material that can be turned into
approximately 328 gallons of ethanol. But in order to plant, grow, and harvest that much corn,
140 gallons of fossil fuels are needed, which comes to about $350 per acre based on current gas
prices. Therefore, the cost of just the feedstock comes to $1.06 for every gallon of ethanol
produced.

Product specification for fuel oxygenate MTBE:

There is a large amount of companies that produce MTBE for purchase. Every company tests
and provides specifications of their product for their potential customers. When companies
purchase products such as MTBE it is very important that the specifications are determined and
released so that they may decide if it meets their requirements. Below is an example of the
specifications of MTBE produced by Monument Chemical Company [11].

Table 1B: Specifications for MTBE produced by Monument Chemical Company. [11]

Reaction path for fuel oxygenate MTBE:

The reaction of methanol and isobutylene is generally an exothermic reaction that occurs at high
temperatures. Treverlyst catalysts are used to increase the reaction conversion rate which allows
the reaction to occur at lower temperatures [12]. Below is a diagram of the reaction between
methanol and isobutylene over a treverlyst catalyst to produce MTBE and water as products.

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 Figure 1B: MTBE reaction path. [12]

Flowsheet and process narrative for fuel oxygenate MTBE:

Below is a process flow diagram for the production of methyl tertiary butyl ether
(MTBE) from methanol and butylenes feed [13]. The process begins by mixing the methanol
and butylenes feed. The mixed stream is then sent through a pump followed by a heat exchanger.
This brings the mixture of methanol and butylenes to the conditions required for the reaction.
The stream is then delivered to the reactor containing a catalyst that ensures a high conversion of
MTBE. Upon exiting the reactor, the mixture is then sent to a distillation column where it is
distilled.
The bottoms from the distillation column consists of MTBE as product. The stream from
the top of the column is then sent to a scrubber where the methanol and butylenes are separated
from the water. The separated water is discarded as waste. Once the methanol and butylenes are
separated from the stream, the unused methanol is recycled while the butylenes are further
processed. By further processing the butylenes this allows the more abundant less desirable
reactants to be removed before the butylenes are recycled back into the process. Processing the
butylenes is a very important step before recycling the stream because it allows the plant to reuse
them while retaining a high rate of conversion.

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Figure 2B: Process Flow Diagram of MTBE production from Methanol and Butylenes. [13]

Following are the tables of the specifications, flow rates, temperatures, pressures and various
other important criteria that must be met for the process to work properly with a high rate of
conversion. [13]

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Table 2B: Specifications of the Streams labeled in Figure 2B. [13]

Table 3B: Specifications of the Utility Stream Flow labeled in Figure 2B. [13]

Table 4B: Specifications of the Reactors and Vessels labeled in Figure 2B. [13]

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 Table 5B: Specifications of the Heat Exchangers labeled in Figure 2B. [13]

Table 6B: Specifications of the Pumps labeled in Figure 2B. [13]

Table 7B: Specifications of the Towers labeled in Figure 2B. [13]

Product specification for fuel oxygenate bioethanol:

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 Figure 1C: How Ethanol Fuel is Represented at the Pump [14]

Bioethanol is ethanol that is produced from biomass such as corn or sugarcane, and is used as
fuel. With the current worldwide problem of global warming, ethanol is a potential fuel source
that is clean to the environment. “The addition of ethanol to gasoline results in improvement of
gasoline properties including octane, oxygen content, volatility, and water solubility” [17]. At
this point, most cars are unable to run on pure ethanol, so it is mixed with gasoline in order for
the common engine to run it. The main advantage of an ethanol mixture fuel is that it creates a
reaction closer to complete combustion, which results in a cleaner exhaust [17]. Another
advantage is that there are many sources of ethanol, which can include any biomass with starch
or sugar. The environmental advantage of bioethanol is that it's a neutral carbon emitter. This is
because ethanol releases carbon when combusted, but the biomass sources consume it to grow.
The most common form of ethanol fuel used today is E10, which is a mixture of gasoline
blendstock and ethanol. In this mixture, the ethanol volume percent is less than 10 [16]. This
blend is able to run in most cars manufactured after 1986, which use a fuel injection system. The
E10 blend is estimated to increase the AKI of the fuel by 2-4 [16]. The ethanol blended fuels are
available at select gas stations, and are very easy to distinguish as you can see in Figure 1C.
There are very strict specifications that ethanol fuel must meet. The industry standard for
ethanol is the ASTM D4960 Standard specification for Denatured Fuel Ethanol for Blending
with Gasoline Use as Automotive Spark Ignition Engine Fuel. The table of specifications for
ethanol used is shown below.

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 Table 1C: Specification Sheet for Bioethanol Fuel [16]

In addition to these standards, the state of California has additional specifications for ethanol
which are as follows.

Table 2C: Additional Specification Sheet for Bioethanol Fuel in California [16]

This is due to California’s increased efforts to decrease emissions. Another, less common form
of ethanol-based gasoline is E85. E85 is a gasoline composed of between 70 and 85 percent
ethanol and unleaded petrol [16]. The problem with this fuel is that it can only be used in select
cars that have an engine built to run on it. These vehicles include V8 super cars and flex-fuel
vehicles. The use of ethanol as fuel has a very promising future, now let's look deeper at the
reaction path and how its formed.

Reaction path for fuel oxygenate bioethanol:

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 Figure 2C: Reaction Path for Glucose to Ethanol [15]

The fermentation process of creating ethanol is a multiple step reaction. The overall reaction
for fermentation of ethanol is 𝐶6 𝐶12 𝐶6 → 2𝐶2 𝐶5 𝐶𝐶 + 2𝐶𝐶2 [16]. The fermentation converts
a mole of sucrose which is normally gathered from corn or sugar cane into two moles of ATP
and ethanol [16]. In the first step of the reaction, the enzyme invertase breaks the glycosidic
linkage connecting fructose and glucose. This reaction is shown by the equation 𝐶12 𝐶22 𝐶11 +
𝐶2 𝐶 + 𝐶𝐶𝐶𝐶𝐶𝐶𝐶𝐶𝐶 → 2𝐶6 𝐶12 𝐶6[16]. The next step in the reaction is called glycolysis.
In this step, the glucose molecules are split into two pyruvate molecules. This reaction is shown
by the equation 𝐶6 𝐶12 𝐶6 + 2𝐶𝐶𝐶 + 2𝐶𝐶 + 2𝐶𝐶𝐶+ → 2𝐶𝐶3 𝐶𝐶𝐶𝐶𝐶− + 2𝐶𝐶𝐶 +
2𝐶𝐶𝐶𝐶𝐶 + 2𝐶2 𝐶 + 2𝐶+ ,where 𝐶𝐶3 𝐶𝐶𝐶𝐶𝐶− is pyruvate and 𝐶𝐶 is inorganic phosphate
[16]. The final two steps show how the pyruvate is turned into carbon dioxide and ethanol. The
first reaction is catalyzed by pyruvate decarboxylase, and turns the pyruvate into acetaldehyde
and carbon dioxide as follows, 𝐶𝐶3 𝐶𝐶𝐶𝐶𝐶− + 𝐶+ → 𝐶𝐶3 𝐶𝐶𝐶 + 𝐶𝐶2 [16]. The final step
turns the acetaldehyde into ethanol and 𝐶𝐶𝐶+ . The 𝐶𝐶𝐶+ is recycled into the glycolysis
reaction. This reaction is catalyzed by alcohol dehydrogenase and is as follows, 𝐶𝐶3 𝐶𝐶𝐶 +
𝐶𝐶𝐶𝐶 + 𝐶+ → 𝐶2 𝐶5 𝐶𝐶 + 𝐶𝐶𝐶+ .[16]. Next, let's look at the flowsheet for how bioethanol is
made.

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Flowsheet and process narrative for fuel oxygenate bioethanol:

Figure 3C: Process Flow Diagram of Ethanol Production from Corn

Above (Figure 3C), is the process flow diagram of ethanol production from corn. The
production starts when the corn is delivered. The corn is normally cleaned and inspected before
reaching the plant. The corn is then sent through a grinder where it is ground into powder called
meal. The meal is mixed with alpha amylase and water, then sent to the cooker. Alpha amylase
is an enzyme that breaks down the alpha bonds of starches [14]. In the cookers, it is important to
keep the pH at 7, this is done by adding sulfuric acid. The cookers have two stages, a high
temperature stage that operates between 120℃ and 150℃, and a low stage that operates around
95℃ [14]. The high temperature stage is used to kill all the bacteria in the liquid mixture. After
the liquid mixture is cooled, another enzyme glucoamylase is added to convert the molecules of
starch to sugar. These sugars include glucose which is fermented shown in Figure 2C. Once the
liquid mixture is sent to the fermenter, yeast is added and fermentation occurs. The fermentation
normally occurs around 30℃ to 35℃ [15]. Most fermentation occurs using a batch reactor
process, where the liquid mixture ferments for roughly two days. Most of the CO2 released in
fermentation is collected and sold to soft drink companies.
After the liquid mixture is fermented, it is referred to as beer. Beer not only includes the
fermented liquid mixture, but also solids from the corn and yeast that were not able to ferment.
The beer is sent to a continuous flow distillation system. In this system the alcohol leaves as
distillate with a .96 wt% [14]. The remainder of the product, referred to as stillage, is sent to a
centrifuge and co-product process. The centrifuge separates the solubles from the grain. Then,
the souables are sent to an evaporator where they are concentrated to 30 wt% solids [14]. This
mixture is referred to as Condensed Distillers Solubles, also known as syrup. The syrup can be
sold as is, or mixed with grain. When the grain and syrup is mixed and dried, a nutritious

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livestock feed is produced. Drying this mixture takes a lot of energy and can total up to 33% of
the plants' energy usage [14].
The alcohol that left the distillation column as distillate is sent through a molecular sieve.
The sieve is used to rid the ethanol solution of any water. The solution is then sent to holding
tanding tanks, and often mixed with a gasoline blendstock before reaching the market. Safe
ethanol handling shows the tanks should be kept at 13℃ [14].

Conclusion:

While both bioethanol and MTBE can be used to increase the fuel efficiency in
combustion engines, we believe bioethanol to be the best choice when blending fuel. Even
though MTBE provides more complete combustion of the fuel, it has several major weaknesses
as compared to bioethanol such as cost and being considered a carcinogenic. Considering
bioethanol requires agricultural products to be produced, which can influence the cost of the
products on the market, but with advancements in genetic engineering the yields of crops are
increasing, resulting in less strain on the market. Bioethanol has only begun to be implemented
by petroleum companies. Over time, the goal is to make an increasing amount of vehicles able
to run on a majority ethanol fuel like E85. More ethanol based fuels would result in lower
emissions and less impact on the environment.

Bibliography (APA):

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