CHBE 378

ELEMENTS of SUSTAINABLE CHEMICAL ENGINEERING

HOMEWORK-2

Submitted by ;

Cansu ERBEY

Submission date : 11.05.2018

Submitted to : Assist. Prof. Betül ÜNLÜSÜ

 Yeditepe University

Kayışdağı/İstanbul

1.Butyl Acetate
Butyl acetate is an organic compound which occurs naturally in food products.
However, it can also be produced chemically. It is commonly used as a solvent
in the production of lacquers and paints. It is a colorless liquid with a low
viscosity, having a sweet banana-like odor. This liquid is volatile but
flammable in nature.

Figure 1.1.Chemical Structure of Butyl Acetate

1.1.Formation
Butyl acetate is a type of an ester; a substance formed by the reaction
between an acid and an alcohol along with the elimination of water. In this
case, the reaction is between acetic acid and butyl alcohol.

Figure 1.2.Formation reaction of Butyl Acetate

Butyl acetate has four isomers: isobutyl acetate, sec-butyl

acetate, tert-butyl acetate, and n-butyl acetate. An isomer is a compound
that exists in forms having different arrangements of atoms, but the same
molecular weight. The following table provides information regarding the
properties of all four isomers of butyl acetate.

1.2.Properties

Table 1.1.Properties of Butyl Acetate

isobutyl sec-butyl tert-butyl n-butyl

Property
acetate acetate acetate acetate

Appearan colorless colorless colorless

colorless liquid
ce liquid liquid liquid

IUPAC isobutyl sec-butyl tert-butyl

butyl acetate
Name acetate acetate acetate
Systemati 2-methylpro 1-methylpro 1,1-dimethylet butyl
c Name pyl acetate pyl hyl ethanoate

n-butyl
acetate;
1-butyl
acetate;
acetic acid
sec-butyl
n-butyl ester;
ester; acetic acid
n-butyl
Other isobutyl s-butyl tert-butyl
ethanoate;
Names ester acetate; ester; t-butyl
butyl ester of
2-butyl acetate
acetic acid;
acetate
1-acetoxybuta
ne; 1-butanol,
acetate; butyl
ester, acetic
acid

Formula C6H12O2 C6H12O2 C6H12O2 C6H12O2

Molar 116.16 116.16

116.16 g/mol 116.16 g/mol
Mass g/mol g/mol

Density 0.875 g/cm3 0.87 g/cm3 0.8593 g/cm3 0.8825 g/cm3

−99°C −99°C −62°C −78°C

Melting
(−146°F; 174 (−146°F; 174 (-79.6°F; (−108°F; 195
Point
K) K) 211.15 K) K)

118°C 112°C 97.8°C 126.1°C

Boiling
(244°F; 391 (234°F; 385 (208.0°F; (259.0°F;
Point
K) K) 370.9 K) 399.2 K)
 17.77°C
Flash 31°C (88°F; 11°C (51.8°F; 22°C (72°F;
(64°F;
Point 304.15 K) 284.15 K) 295 K)
290.92 K)

Specific
Gravity at 0.873 0.872 0.87 0.8826
20/20°C

Solubility 0.8 g/100 0.68 g/100 mL

7 g/L (20ºC) insoluble
in Water mL (20°C) (20°C)

Vapor 15 mmHg 10 mmHg 47 mmHg 11.25 mmHg

Pressure (20°C) (20°C) (25°C) (25°C)

CAS
110-19-0 105-46-4 540-88-5 123-86-4
Number

1.2.Applications of Butyl Acetate

● tert-Butyl acetate is used as an additive to gasoline to prevent engine

knocking. It is also used as a solvent for lacquers.

● n-Butyl acetate easily dissolves nitrocellulose, a nitric acid ester used in

lacquers. Therefore, it is used as a solvent in the manufacture of
nitrocellulose lacquers.

● It is used as a solvent in the production of nail polish, nail polish removers,

basecoats, and other nail-care products.

● It is used as a synthetic-fruit flavoring in foods such as candy, ice cream,

baked goods, cheeses, yogurts, etc.

● It is used in as a solvent in organic chemistry laboratories.

● It is used in the manufacture of Penicillin-G, the principal component of
many commercial antibiotics.

● It is used in the manufacture of artificial leather, cleaners, photographic

films, plastics, and safety glass.

● Due to its low solubility in water, n-Butyl acetate is used as an extractant in

the manufacture of pharmaceutical preparations.

● It is used as a diluting agent for dyes in inks used for marking vegetables
and fruits.

● n-butyl and isobutyl acetate both are used in the production of perfumes.

● sec-Butyl acetate is used as a solvent for nail polish and lacquer. It is also
used in the production of paper coatings.

1. Gas Expanded Liquids

1.1. Physical and Chemical Properties

While supercritical carbon dioxide systems offer many desirable properties,

they require elevated temperatures and high pressures and only allow for the
poor solubility of many species. These limitations can be addressed through
the use of gas-expanded liquid (GXL) systems . Gas-eXpanded Liquids (GXLs)
are mixtures of an organic solvent and a pressurized gas. In these systems, a
liquid solvent (e.g., hexane) is pressurized with a gas (e.g., CO2) where the
gas partitions (dissolves) into the liquid phase to create a solvent mixture at
greater than atmospheric pressure but less than the vapor pressure of the
pure gas. At low pressures, very little gas is dissolved in the organic phase,
however with increases in the applied pressure of the gas, the volume of the
liquid phase drastically increases due to the increased solubility of the gas. A
commom GXL has been hexane-CO2 mixtures; the vapor liquid equilibrium of
this hexane-CO2 mixture, as well as other mixtures, can be predicted using
the Peng-Robinson equation of state . Figure 1.4a demonstrates the volume
change of hexane when pressurized with CO2 such that

V V  Va

Va Va

where V is the total liquid volume at an applied CO 2 pressure and Vo is the

liquid volume of neat hexane at atmospheric conditions. As the applied CO 2
pressure increases, the solubility of CO2 in the organic solvent (in this case,
hexane), increases drastically leading to a volume increase and a significant
change in the properties of the liquid mixture. The composition and
physico-chemical properties (e.g., density, viscosity, diffusivity, solvent
strength, and surface tension) of the solvent mixtures can be easily tuned
between those of the organic solvent and those of the pure gas by simple
variations the applied partial 20 pressure of the gas. An additional advantage
of using these systems involves the recovery and recycle of both the organic
phase and gas through simple depressurization. The solvent strength of GXLs
can be tuned between those of the gas and those of the liquid, in part, due to
the ability to change the polarity of the solvent mixture. Wyatt et al.
reported the Kamlett-Taft π ∗ parameter (a measure of solvent polarity and
polarizability) as measured by solvatochromic dyes for CO2-expanded acetone
and methanol. It was found that the addition of CO2 to those solvents greatly
reduced the solvent polarity as CO2 is a net-zero pole. Jessop and coworkers
were able to use gas expanded liquids as switchable solvents for the
dissolution and subsequent recovery of flourocompounds ). Mcleod et al.
were able to demonstrate the controllable solvent strength of GXLs through
the controlled precipitation of nanoparticles . Mass transport properties of
gas-expanded liquid systems have been shown to be tunable with the applied
system pressure of the selected gas. The diffusion coefficient of benzene in
CO2-expanded methanol was reported to be enhanced between 4 and 5 fold
with CO2 addition . Likewise, the diffusivities of pyridine, pyrimidine,
pyrazine, and 1,3,5-triazine in CO2-expanded methanol increased with
applied CO2 pressure . Kho et al. reported the measured viscosities of
CO2-expanded fluorinated solvents and found a 4-5 fold decrease with CO2
addition . Hsu et al. found the surface tension of CO 2-expanded n-hexane
decreased by two orders of magnitude with CO2 addition .

1.2. Applications of Gas Expanded Liquids

2.2.1.Economics

There are relatively few known examples of commercialization in the areas

of chemical manufacturing and particle formation processes employing dense
C02 , despite nearly two decades of research in these areas and the promise
of many potential applications. This is in contrast to the many industrial scale
C02 - based plants worldwide in the food and natural products industries (such
as the decaffeination of coffee beans, extraction of hops and spices, etc.)
and other C0 2 applications including dry cleaning and precision cleaning
(141,142), paints and coatings (Union Carbide process), polymer processing
(DuPont Fluoropolymers Plant) and hydrogenations. For GXL-based
technologies to gain wider acceptance in chemical manufacturing, process
economic analysis based on plant scale simulations and demonstration of
satisfactory pilot plant scale performance are necessary. Reliable knowledge
of the phase behavior, intrinsic kinetics, fluid dynamics and transport
properties involving GXLs is essential for rational process design and
simulation.

2.2.3.Safety

When using compressed C02 to expand less volatile liquid phases, the
vapor-liquid equilibrium is such that the vapor phase is dominated by C02 .
The presence of C02 in the vapor phase provides safety benefits in the case of
02 - based oxidation reactions by reducing the propensity to form explosive
hydrocarbon/02 mixtures in the vapor phase. "Calculated Adiabatic Reaction
Temperature" (CART) is the most widely used method to estimate vapor
phase hazardous behavior. The temperature rise of a combustion reaction,
based on vapor phase composition, is calculated under adiabatic conditions.
The Gibbs free energy minimization method is typically employed for
predicting the flammability of fuels and chemicals such as lower alkanes,
esters and carboxylic acids . It is well known that inert gases arrest flames
when used in substantial quantities (>50% by volume in an 02 /inert/fuel
mixture). In general, triatomic inert gases (C02 , water) reduce the
flammable region to a greater extent than diatomic or monoatomic inert
gases . In the case of each inert, the flammable region vanishes completely
beyond a certain concentration. As shown in Figure 11, for methane+02
mixtures, this critical concentration is around 20 mole% for C0 2 . In other
words, an adequate presence of C02 (instead of N2 ) in an 02-containing vapor
phase reduces the flammability of various hydrocarbon+O mixtures . This
implies the possibility of operating with 02-enriciied atmospheres (where 0 2
concentration exceeds 21 mole%) in the presence of C02 with reduced or even
no flammability hazards.

REFERENCES

1. https://sciencestruck.com/butyl-acetate-properties-uses

2. Gas Expanded Liquids:Fundamentals and Applications , Aaron M. Scurto ,

Keith Hutchenson , and Bala Subramaniam1