Dimethyl Aniline PDF
Dimethyl Aniline PDF
Dimethyl Aniline PDF
PROJECT BY mIKHIL
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MANUFACTURE OF DMA
Table of Contents
CHAPTER 1: INTRODUCTION 5
1.1 DIMETHYLANILINE 6
1.2 HISTORY 8
CHAPTER 2: PHYSICAL AND CHEMICAL PROPERTIES 9
2.1 CHEMICAL AND PHYSICAL DATA 10
CHAPTER 3: MATERIAL SAFETY AND DATA SHEET 12
3.1 MSDS 13
CHAPTER 4: APPLICATION 20
4.1 APPLICATION 21
5.1 PROCESSES 24
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CHAPTER 1
INTRODUCTION
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A
BRIEF
HISTORY
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1.2 HISTORY
DMA was first reported in 1850 by A. W. Hofmann, who prepared it by heating aniline and
iodomethane:
C6H5NH2 + 2 CH3I → C6H5N(CH3)2 + 2 HI
DMA is produced industrially by alkylation of aniline with methanol in the presence of an acid
catalyst:
C6H5NH2 + 2 CH3OH → C6H5N(CH3)2 + 2 H2O
Similarly, it is also prepared using dimethyl ether as the methylating agent.
Dimethylaniline undergoes many of the reactions expected for an aniline, being
weakly basic and reactive toward electrophiles. N, N-Dimethylaniline is produced commercially
by heating aniline at 300°C with
Methanol in the presence of a catalyst at high pressure; sulfuric acid, phosphoric acid or
Alumina can be used as the catalyst (Northcott, 1978; Rosenwald, 1978; Budavari, 1989).
N, N- Dimethylanilne is produced by one company each in France, Germany, Hungary,Korea,
Spain and the USA, by two companies in Japan and The United Kingdom and by four companies
in India (Chemical Information Services, 1991).
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CHAPTER 2
PHYSICAL
AND
CHEMICAL
PROPERTIES
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(2-14 g/l at 25°C). Since N,N-dimethyl aniline is a basic compound, its solubility is dependent
on the pH of the aqueous medium: its solubility in water at pH ).
7 is lower than that in water of pH .: 5. The data on aqueous solubility reported in the literature
thus vary widely (US Environmental Protection Agency, 1986). Soluble in acetone, benzene,
chloroform, diethyl ether and ethanol (Amoore & Hautala, 1983; Dragun & Hellng, 1985; Sax &
Lewis, 1987; Lide, 1991)
(g) Volatility: Vapour pressure, 1 mm Hg (133 Pal at 29.5 °C (Lide, 1991)
(h) Stability: Slowly oxidizes and darkens in air; can react with nitrous acid to form ring-
substituted nitroso compounds (US Environmental Protection Agency, 1986)
(i) Octanol/water partition coeffcient (P): 2.31 (Hansch & Leo, 1979)
(j) Conversion factor: mg/m3 = 4.95 x ppm1.
TRANSPORTATION
PACKING: 180 Kg in Drum
HAZARD CLASS: 6.1 (Packing group: II)
UN NO.: 2253
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CHAPTER 3
MATERIAL
SAFETY
DATA
SHEET
(M.S.D.S.)
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Composition:
Name CAS # % by Weight
{N,N-}Dimethylaniline 121-69-7 100
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Eye Contact: Check for and remove any contact lenses. Immediately flush eyes with running
water for at least 15 minutes, keeping eyelids open. Cold water may be used. Do not use an eye
ointment. Seek medical attention.
Skin Contact: After contact with skin, wash immediately with plenty of water. Gently and
thoroughly wash the contaminated skin with running water and non-abrasive soap. Be
particularly careful to clean folds, crevices, creases and groin. Cold water may be used. Cover
the irritated skin with an emollient. If irritation persists, seek medical attention. Wash
contaminated clothing before reusing.
Serious Skin Contact: Wash with a disinfectant soap and cover the contaminated skin with an
anti-bacterial cream. Seek immediate medical attention.
Inhalation:
Allow the victim to rest in a well ventilated area. Seek immediate medical attention.
Serious Inhalation: Evacuate the victim to a safe area as soon as possible. Loosen tight clothing
such as a collar, tie, belt or waistband. If breathing is difficult, administer oxygen. If the victim is
not breathing, perform mouth-to-mouth resuscitation. Seek medical attention.
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Ingestion: Do not induce vomiting. Examine the lips and mouth to ascertain whether the tissues
are damaged, a possible indication that the toxic material was ingested; the absence of such
signs, however, is not conclusive. Loosen tight clothing such as a collar, tie, belt or waistband. If
the victim is not breathing, perform mouth-to-mouth resuscitation. Seek immediate medical
attention.
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Small Spill: Dilute with water and mop up, or absorb with an inert dry material and place in an
appropriate waste disposal container.
Large Spill: Combustible material. Keep away from heat. Keep away from sources of ignition.
Stop leak if without risk. Be careful that the product is not present at a concentration level above
TLV. Check TLV on the MSDS and with local authorities.
Precautions: Keep away from heat. Keep away from sources of ignition. Ground all equipment
containing material. Do not ingest. Do not breathe gas/fumes/ vapour/spray. Wear suitable
protective clothing In case of insufficient ventilation, wear suitable respiratory equipment If
ingested, seek medical advice immediately and show the container or the label. Avoid contact
with skin and eyes
Storage: Flammable materials should be stored in a separate safety storage cabinet or room.
Keep away from heat. Keep away from sources of ignition. Keep container tightly closed. Keep
in a cool, well-ventilated place. Ground all equipment containing material. Keep container dry.
Keep in a cool place.
Engineering Controls: Provide exhaust ventilation or other engineering controls to keep the
airborne concentrations of vapors below their respective threshold limit value. Ensure that
eyewash stations and safety showers are proximal to the work-station location.
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Personal Protection: Splash goggles. Lab coat. Vapor respirator. Be sure to use an
approved/certified respirator or equivalent. Gloves.
Personal Protection in Case of a Large Spill: Splash goggles. Full suit. Vapor respirator.
Boots. Gloves. A self contained breathing apparatus should be used to avoid inhalation of the
product. Suggested protective clothing might not be sufficient; consult a specialist BEFORE
handling this product.
Exposure Limits:
TWA: 5 CEIL: 10 (ppm) from ACGIH (TLV) TWA: 25 CEIL: 50 (mg/m3) from ACGIHConsult
local authorities for acceptable exposure limits
Toxicity to Animals: Acute oral toxicity (LD50): 1410 mg/kg [Rat]. Acute dermal toxicity
(LD50): 1770 mg/kg [Rabbit].
Other Toxic Effects on Humans: Very hazardous in case of ingestion. Hazardous in case of
skin contact (irritant, permeator), of inhalation.
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Products of Biodegradation:
Possibly hazardous short term degradation products are not likely. However, long term
degradation products may arise.
Toxicity of the Products of Biodegradation: The products of degradation are more toxic.
Waste Disposal:
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Other Classifications:
WHMIS (Canada): CLASS B-3: Combustible liquid with a flash point between 37.8°C (100°F)
and 93.3°C (200°F). CLASS D-1A: Material causing
Immediate and serious toxic effects (VERY TOXIC). CLASS D-2B: Material causing other
toxic effects (TOXIC).
DSCL (EEC):R21/22- Harmful in contact with skin and if swallowed. R36/38- Irritating to eyes
and skin.
HMIS (U.S.A.):
Health Hazard: 3
Fire Hazard: 2
Reactivity: 0
Personal Protection: h
National Fire Protection Association (U.S.A.):
Health: 3
Flammability: 2
Reactivity: 0
Specific hazard:
Protective Equipment:
Gloves. Lab coat. Vapor respirator. Be sure to use an approved/certified respirator or equivalent.
Wear appropriate respirator when ventilation is inadequate. Splash goggles.
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CHAPTER 4
APPLICATIONS
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4.1 Applications
DYES
N, N-Dimethylaniline is used in the manufacture of Michler's ketone which is a chemical
intermediate used in the synthesis of many dyes and pigments, particularly auramine derivatives.
These pigments are used to dye paper, textiles, and leather. The main types of the dyes that can
be manufactured from DMA are alkali light yellow, alkali purple 5BN, alkali light green, alkali
turquoise blue, bright red 5 GN, bright blue. DMA is a key precursor to commercially important
triarylmethane dyes such as Malachite green or Crystal (Gentian) violet used as a histological
stain and in Gram's method of classifying bacteria.
PROMOTERS
DMA serves as a promoter in the curing of polyester and vinyl ester resins. This compound can
be used on its own with benzoyl peroxide (BPO) type catalysts or in combination with cobalt 6%
promoters with methyl ethyl ketone(MEKP) type catalysts. These systems give rapid cure at
room temperature. DMA helps the catalyst to start the chemical reaction. Promoters must never
be mixed directly with catalyst since a violent explosive reaction results.
STABILISERS
DMA is used as a stabilizer for colorimetric peroxidase determination.
FRAGRANCE
N,N-Dimethylaniline is used as an intermediate to manufacture vanillin.
PHARMA
DMA is used to manufacture cephalosporin V, madribon, sulphormethoxine and flucytosine in
medical industry. It is used as an acid scavenger in the synthesis of penicillins and
cephalosporins and has been reported as a contaminant of commercial preparations of those
antibiotics at levels of up to 1500 ppm.
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Other Uses:
Specialty industrial solvent and rubber vulcanizing agent.
Reagent in chemical synthesis.
Catalytic hardener in certain fibreglass resins.
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CHAPTER 5
MANUFATURING
PROCESSES
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1] BY ALKYLATION OF ANILINE:
REACTION:
Thus, aniline, with a considerable excess of methyl alcohol and a catalytic amount of sulfuric
acid, is heated in an autoclave at about 200oC for 5 or 6 hours at a high reaction pressure we get
dimethylaniline . Vacuum distillation is used for purification.
In the alkylation of aniline to dimethylaniline by heating aniline and methyl
alcohol, sulfuric acid cannot be used because it will form ether; consequently,hydrochloric acid is
employed, but these conditions are so corrosive that the steel used to resist the pressure must be fitted
with replaceable enameled liners.Thus in presence of Al2O3 as a catalyst is used.
2] BY NITRATION OF BENZENE:
REACTION:
Benzene ring in presence of H2SO4 reacts with nitric acid to give nitrobenzene and water. The
obtained nitrobenzene is subjected to hydrogenation in presence of palladium catalyst and ethanol gives
aniline. And further, aniline on reacting with methyl chloride or chloromethane produces N, N-Dimethyl
aniline.
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CHAPTER 6
PROCESS
DESCRIPTION
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ANILINE
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PROPERTIES OF ANILINE
Molecular formula:C6H5NH2
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METHANOL
Derived from natural gas, methanol is a hydrocarbon, comprised of carbon, hydrogen and
oxygen. Its chemical formula is CH3OH.
Methanol is an alcohol and is a colorless, neutral, polar and flammable liquid. It is miscible with
water,alcohols, esters and most other organic solvents. It is only slightly soluble in fats and oils.
Detailed physical and chemical properties of methanol are provided in the following pages.
Methanex produces methanol using a catalytic process with natural gas and steam as the
feedstocks. The natural gas is catalytically reformed to carbon oxides and hydrogen. The
resulting synthesis gas mixture is circulated under pressure and moderate temperature in the
presence of a metallic catalyst and converted to crude methanol. The crude methanol is distilled
to yield commercial chemical grade methanol.
Other common names for methanol include methyl alcohol, methyl hydrate, wood spirit, wood
alcohol, and methyl hydroxide.
Methanol is used as a building block for many chemicals and products. Other uses include
windshield washer antifreeze, fuels, waste water treatment and biodiesel production.
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PROPERTIES OF METHANOL
Molecular formula:CH4O
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First methanol is passed through heat exchanger to rise the temperature to 2600 C.
Then it is passed to the reactor to convert it into dimethylether gas in presence of alumina
(Al2O3)a instead of sulphuric acid as a catalyst , because sulphuric acid is corrossive
towards the reactor vessel.
REACTION:
2CH3OH → CH3-O-CH3+H2O
METHANOL DIMETHYLETHER
The effluent from the reactor is passed to ETP and DME gas is passed to autoclave.
Here, it is mixed with aniline at high temperature and high pressure of 540 psi (3.7
MPa)about 5 to 6 hours.
REACTION:
CH3-O-CH3+C6H5NH2 → C6H5N(CH3)2+H2O
DIMETHYLETHER ANILINE DIMETHYLANILINE
To purify the mixture from autoclave, it is passed through series of vaccum distillation
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coloumn. Thus, pure dimethylaniline is formed and passed to further processes and
storage.
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CHAPTER 6
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CHAPTER 6
MATERIAL
BALANCE
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MATERIAL BALANCE
REACTION 1:
2CH3OH → CH3-O-CH3 + H2
x = 36.8gm of DME
REACTION 2:
Therefore ,
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DME = 7.36gm
H2O =11.52gm
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34.44kmol/hr
REACTION 1:
REACTION 2:
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F DB D x f xb
Fx f Dxd Bxb B x d x f
6637.7
Total
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CHAPTER 8
ENERGY
BALANCE
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ENERGY BALANCE
Total feed=4898.24kg
Assume water used 500kg
Reactor 1
mxCpxΔT=mxCpxΔT
4898.24x(533-298)x2.51=mx4.187x(573-T)
Q=2889226.864kJ/kg
4896.24x(533-298)x2.51=5000x4.187x(573-T)
T(out) of Water=434.9K
Q=mxCpxΔT+Mxλ
=153.057x0.06143x(623-533)+34.4x153.057
=611.367kJ
Req. of steam for the autoclave
Q=mxλ
611.36=mx1736.2
=3.51kg
λaniline=4.838kJ/kmolK
Cp(mix)=Cp(aniline)xmolar mass of aniline+Cp(DME)xmolar mass of DME
=12.115kJ/kmolK
Reactor 2
Q=mxCpxΔT+Mxλ
=332.55x12.11x(673-473)+222.5x4.838
=805545.148kJ
Req. of heat for total reactor
Q=mxλ
805545.148=mX1825.1
=441.37kg/hr
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CHAPTER 9
EQUIPMENT
DESIGN
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Shell side
MOC: CS
No. of shells: 1
No. of passes: 1
Fluid: liquid
Head
Bolts: steel
Vent: 25mm
Drain: 25mm
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No. of tubes: 54
Length: 12m
Fluid: gas
Working pressure:19N/mm2
MOC: CS
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Shell side
Shell Diameter
a=S2T=252=625mm2
an=2x54x625=67500mm2
As=π/4xD=an/β β=0.7
Ds=(61500x4/0.7xπ)0.5
=350.4mm
Shell Thickness
t=pDi /(2fJ-p)
=0.5x400/(2x95x0.85-0.5)
=1.24mm
tn=pDi/(2fJ-p)
=0.5x75/(2x95x0.85-0.5)
=0.23mm
Head Thickness
th= [pRcW/(2fJ)]+c
= [0.5x400x1.54/(2x95x0.85)]+1.5
= 3.4mm
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Go=440mm
Gi=416mm
G=428mm
bo=N/2=24/2=12
b=2.5x bo0.5
=8.66
Seating stress(Ya)=53.4N/mm2
Gasket factor(m)=3.75
Wm1=πbGYa
=πx8.66x428x53.40
=6.2x105N
Wm2=πx2x8.66x428x3.75x0.5+(π/4)x4282x0.5
=1.15x105N
k=1/(0.3+(1.5WmhG/HG))
Wm=6.2x105
hG =48.5
H=71936.6
G=428
k=0.565
tf=G(p/kf)0.5
=428x(0.5/0.565x95)0.5
=41.3mm
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Tube side
Thickness of tube
tf=pDo /(2fJ+p)
=(21.5x18)/(2x100.6+21.5)
=1.74mm
Tube sheet
t=FGx(0.25p/f)0.5
=1.25x380x(0.25x21.5/100.6)0.5
=109.8mm
T=Gc x(kp/f)0.5
=380x(0.3x21.5/95)
=99.02mm
G=380mm
bo=w/8=22/8=2.75mm
Ya=126.6N/mm2
m=5.5
Wm1=πbGYa
=πx980x2.75x126.6
=4.16x105N
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Wm2=πx2x2.75x380x5.5x21.5+(π/4)x3802x21.5
=32.14x105N
=22859.2mm2
No. of bolt=38/2.5
=15.2
=42.65mm
Flange thickness
k=1/(0.3+(1.5WmhG/HG))
=1.47
Tube sheet
tf=G(p/kf)0.5
=145mm
Nozzles
tn=pDi/(2fJ-p)
=9.6mm
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SHELL:
Weir height 50 mm
Downcomer clearance 25 mm
SUPPORT SKIRT:
Height of support 1 m
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TRAYS-SIEVE TYPE:
Number of trays = 9
Number of holes:
Tray spacing:
Thickness = 3 mm
Di = diameter of shell, mm
C = Corrosion allowance, mm
J = Joint factor
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J= 85% = 0.85
W= ¼ × (3 + (Rc/Rk)0.5)
Rk = 6% × Rc = 0.06×1990 = 119.4 mm
= 0.366×1.88×105× (6/1990)2
Hence, the thickness is satisfactory. The thickness of the shell and the head are made
Weight of Head:
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sf =1”
icr = 1¼”
d = 84.45” = 2144.97 mm
3.2 a Compressive stress due to Weight of shell up to a distance ‘X’ meter from top.
fds=0.85x Xkg/cm2
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Where
Dins, tins, ρins are diameter, thickness and density of insulation respectively.
Dm = (Dc+ (Dc+2ts))/2
3.2c Stress due to the weight of the liquid and tray in the column up to a height X meter
fd, liq. = weight of liquid and tray per unit height X/ π×Dm× (ts - c)
The top chamber height is 0.3 m and it does not contain any liquid or tray. Tray spacing is 500
mm.
3.2d Compressive stress due to attachments such as internals, top head, platforms and ladder
up to height X meter
Now total weight up to height X meter = weight of top head + pipes +ladder, etc., Taking the weight
of pipes, ladder and platforms as 25 kg/m = 0.25 kg/cm
2
fd (attch.)= (170.19+25X) × 10/ π×199× (6 - 3) = 0.907 + 0.133X kg/cm
Total compressive dead weight stress:
fdx = fds + fins +fd (liq) + fd (attch)
= 0.85X + 0.98155X + [3.26X+0.653] + [0.907 +0.133X]
fdx = 5.225X + 1.559 kg/cm2
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= 1.5 for distillation column with several manways, and with plate Support
rings or equivalent fittings
Hv = height or length between tangent lines (length of cylindrical section) g =
gravitational acceleration = 9.81 m/s2
t = wall thickness
m = density of vessel material, kg/m3
Dm = mean diameter of vessel = Di + (t ×10-3)
= 1.99+ (6 ×10-3) = 1.996 m
Trays:
The trays are standard sieve plates throughout the column. The plates have 6981
holes in Enriching section and 10726.11 holes in the Stripping section of 5mm
diameter arranged on a 15mm triangular pitch. The trays are supported on purloins.
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CHAPTER 11
PLANT
LAYOUT
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PLANT LAYOUT
A preliminary site layout has been sketched. The layout of the plant is decided keeping the
following factors in mind.
The utilities and storage facilities are segregated from the main body of the plant. A separate
gate may be provided in this area. This gate can be used for trucks and tankers carrying the raw
materials, cooling water.
The units in the plant are the main plant, administrative building, utilities, canteen etc. The
vessel should be located close to the entry and exit point of the plant to facilitate loading and un
loading. The fire engines have easy access to all parts of the plant in case of any accidents.
Prevailing the wind conditions should also be considered in the relative locations of equipment.
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CHAPTER 12
HAZOP
STUDY
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HAZOP
The basic data is to let the mind go free in a controlled fashion in order to consider all
possible ways that process and operational failures can occur.
Before HAZOP study started , detailed information on the process must be available.
This includes up-to-date process flow diagrams (PFDs), process and instrumentation diagrams
(P & Ids).Detailed equipments specifications, MOC & Mass & energy balances.
Here as far as our project is concerns the main hazards can from reactor itself where the
endothermic reaction is carried out.
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CHAPTER 13
PROJECT
COST
ESTIMATION
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COST ESTIMATION
Acceptable plant design must present a process that is capable of operating under conditions,
which will yield profit. Since net profit equal total value minus all expenses, it is essential that
the chemical engineer be aware of the many different types of cost involved in the manufacturing
processes. Capital must allocate for the direct, plant expenses, such as those for raw material,
labor and equipment.
Money is worth hence must be spent where required in a definite foolproof manner. For any
project the cost is of prime importance. The cost estimation is required so as to study about the
financial requirements, so that no future financial crisis should occur, for any project.
FIXED CAPITAL:
No. of building = 5
= 5000 m2
= 5000 x 1500
= 75,00,000 Rs.
= 5000 x 2000
= 1,00,00,000Rs.
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REACTOR 1 30,00,000
CONDENSER 1 75000
AUTOCLAVE 1 30,00,000
PUMPS 4 40,000
= 6,81,500 Rs.
=4,77,050 Rs.
= 6,13,350Rs.
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MANUFACTURE OF DMA
= 85,86,900Rs.
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MANUFACTURE OF DMA
WORKING CAPITAL:
A) ADMINISTRATIVE EXPENSES:
Total
Position People required Salary (lakhs./annum)
(lakhs./annum)
Engineers 3 3 9.0
Chemists 1 2 2.0
Receptionist 1 1 1.0
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MANUFACTURE OF DMA
C) UTILITIES COST:
ELECTRICITY 15
STEAM 10
= 24,57,11,580Rs.
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MANUFACTURE OF DMA
Profit margin
Assuming 100% capacity utilization
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MANUFACTURE OF DMA
CHAPTER 14
CONCLUSION
&
REFERENCES
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MANUFACTURE OF DMA
CONCLUSION
This report gives a pre-preliminary feasibility study of a plant manufacturing of Dimethyl
aniline to be set up in India. Alkylation of aniline is the manufacturing process selected which
gives good yield and purity.
As a part of this report, the basic Mass Balance, Energy Balance, Process and
Instrumentation, Process Designing was included to give an analysis of the feasibility of the
project.
The estimated cost of the project was found to be Rs. 27.18 Crores. A payback period of
20.83 yrs is expected with a return on investment (ROI) of 4.8 %, assuming 100% capacity
utilization. By seeing the payback period and the profits, it seems that the project is economically
attractive and profitable.
In this analysis several assumptions have been made including that of an ideal market
with all that is produced being sold. Also, product prices have been assumed to remain constant.
To get a clearer picture a detailed feasibility report has to be done. However the
preliminary study does provide sufficient reason to conduct a detailed analysis to come at exact
figures.
This pre-preliminary feasibility report thus calls for and justifies the need for a more
detailed and rigorous analysis of the project in terms of the market demand for the product, the
actual yields from the process and the saleability of the product.
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MANUFACTURE OF DMA
Bibliography
ROBERT THORNTON MORRISON AND ROBERT NEILSON BOYD,ORGANIC
CHEMISTRY,SIXTH EDITION.
JAMES G. SPEIGHT, CHEMICAL AND PROCESS DESIGN HANDBOOK.
Shreve‟s Chemical process Industries
Perry‟s Chemical Engineers Handbook, Robert H. Perry, Don W. Green 7th Edition.
M. V. Joshi & V. V. Mahajani, “Process Equipment Design”
Beigler, Grossman and Westerberg, “Systematic Methods of Chemical Process Design”.
R.K.Sinnott, Coulson & Richardson, “Chemical Engineering Design” - Volume 6.
Webliography
www.google.com
www.wikipedia.com
www.britannica.com
www.compositesaustralia.com
toxnet.nlm.nih.gov
ScienceLab.com
MGM’s College of Engineering & Technology Kamothe, Navi Mumbai (2011-12). Page 68