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MANUFACTURING OF DMA
MAHATMA GANDHI MISSION’S
COLLEGE OF ENGINEERING & TECHNOLOGY
KAMOTHE, NAVI MUMBAI.
ACADEMIC YEAR : 2011-2012.
PROJECT REPORT
ON
MANUFACTURE OF “DIMETHYL ANILINE”
UNDER THE GUIDANCE OF
Prof : ANIL RANVEER
SUBMITTED BY-
SIDDHESH A. VEDANTE
SIDDHESH A. PHANSEKAR
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MANUFACTURING OF DMA
Department of Chemical Engineering
MAHATMA GANDHI MISSION’S
COLLEGE OF ENGINEERING & TECHNOLOGY
KAMOTHE, NAVI MUMBAI.
CERTIFICATE
This is to certify that the following students,
SIDDHESH A. VEDANTE
SIDDHESH A. PHANSEKAR
have successfully completed the project report entitled “DIMETHYL ANILINE” during
the prescribed period in the academic year 2010-12. This Project report is submitted in the
partial fulfillment of “BACHELOR OF CHEMICAL ENGINEERING” of Mumbai
University.
GUIDE EXAMINER
( Prof. ANIL RANVEER )
HEAD OF DEPARTMENT PRINCIPAL
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MANUFACTURING OF DMA
ACKNOWLEDGEMENTS
This project would never have seen the light of the day if it hadn’t been for support and
encouragement of multitude of very exemplary people.
We would like to sincerely thank my guide Prof. ANIL RANVEER who is the driving force
behind this project and discussion with him proved to be enlightening.
We express our sincere gratitude toward our principal Dr. GEETHA JAYARAJ & Head
of Chemical Engineering Department Dr. C K MISTRY , for providing us with the opportunity
to chose this project. We would be failing our duty if we do not acknowledge the help extended
by professors of Chemical Department of MGM’S college of engineering and technology. Our
heart felt gratitude to library and their staff member.
SIDDHESH A. VEDANTE
SIDDHESH A. PHANSEKAR
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MANUFACTURING 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
CHAPTER 5: MANUFACTURING PROCESS 23
5.1 PROCESSES 24
CHAPTER 6: PROCESS DESCRIPTION 25
6.1 RAW MATERIALS 26
6.2 DETAILS OF SELECTED PROCESS 27
6.3 PROCESS FLOW DIAGRAM 32
BIBLIOGRAPHY 33
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MANUFACTURING OF DMA
CHAPTER 1
INTRODUCTION
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MANUFACTURING OF DMA
1.1 Introduction Of Dimethylaniline
N,N-Dimethylaniline (DMA) is an organic chemical compound, a substituted derivative of
aniline. It consists of a tertiary amine, featuring dimethylamino group attached to a phenyl group.
This oily liquid is colourless when pure, but commercial samples are often yellow. It is an
important precursor to dyes such as Crystal violet.
N, N- Dimethylaniline is used as an intermediate in the manufacture of dyes and other products
and as a solvent for special purposes, a rubber
vulcanizing agent and a stabilizer. It has been
detected in ambient water and soil in the vicinity
of industrial facilities N, N-Dimethylaniline can be
detected in air by adsorption on silica gel,
desorption with ethanol and analysis by gas
chromatography and flame ionization detection.
The limit of detection is 10 l1g/sample Amines
can be liberated during the manufacture of rubber,
especially by vulcanization and by other thermal
degradations. A method was described for the
determination of free aromatic amines.
Including N,N-dimethylaniline, using high-temperature glass-capillary gas chromatography and
nitrogen-selective detection (thermionic specific detector), with detection limits of 10-20 pg.
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MANUFACTURING OF DMA
A
BRIEF
HISTORY
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MANUFACTURING OF DMA
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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MANUFACTURING OF DMA
CHAPTER 2
PHYSICAL
AND
CHEMICAL
PROPERTIES
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MANUFACTURING OF DMA
2.1 Chemical and physical data
N,N-Dimethylaniline (DMA) is colourless or pale yellow to brown, oily liquid with
characteristic amine-like odor. DMA is less dense than water and insoluble in water. Freely
soluble in alcohol, acetone, benzene, chloroform, diethyl ether, ethanol and acid solution. Stable
under ordinary conditions of use and storage. Combustible. DMA is a weak base incompatible
with strong oxidizing agents, strong acids, acid chlorides, acid anhydrides, chloroformates,
halogens. It emits toxic fumes of nitriogen oxides, carbon oxides, and aniline when heated to
decomposition. (C8H11N) MoL. wt: 121.18.
Synonyms, structural and molecular data
Chem. Abstr. Sem Reg. No.: 121-69-7
Chem. Abstr. Name: N,N- Dimethyl benzenamine
IUPAC Systematic Name: N,N-Dimethylaniline
Synonyms: (Dimethylamino )benzene; N,N-dimethylaminobenzene; dimethylanilne;
dimethylphenylamine; N,N-dimethylphenylamine
Chemical and physical properties
(a) Description: Yellowish to brownish oily liquid (Sax & Lewis, 1987)
(b) Boiling-point: 192-194 °C (ElIer, 1985; Lide, 1991)
(c) Melting-point: 2-2.45 °C (ElIer, 1985; Lide, 1991)
(d) Density: 0.956 g/ml at 20°C (Eller, 1985)
(e) Refractive Index: 1.5580
(f) Spectroscopy data: Infrared, ultraviolet and nuclear magnetic resonance spectral data have
been reported (Sadtler Research Laboratories, 1980; Pouchert, 1981, 11983; US Nation9al
Toxicology 9Pro 1)gram., 1989; Sadtler .Research Laboratories, if Solubilty: Insoluble in water
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MANUFACTURING OF DMA
(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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MANUFACTURING OF DMA
CHAPTER 3
MATERIAL
SAFETY
DATA
SHEET
(M.S.D.S.)
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MANUFACTURING OF DMA
3.1 Material Saftey And Data Sheet
Section 1: Chemical Product and Company Identification
Product Name: N,N-Dimethylaniline
Catalog Codes: SLD3868
CAS#: 121-69-7
RTECS: BX4725000
TSCA: TSCA 8(b) inventory: N,N-Dimethylaniline
CI#: Not available.
Synonym: Xylidine
Chemical Formula: C8H11N
Section 2: Composition and Information on Ingredients
Composition:
Name CAS # % by Weight
{N,N-}Dimethylaniline 121-69-7 100
Toxicological Data on Ingredients: N,N-Dimethylaniline: ORAL (LD50): Acute: 1410 mg/kg
[Rat]. DERMAL (LD50): Acute:1770 mg/kg.
Section 3: Hazards Identification
Potential Acute Health Effects:
Very hazardous in case of ingestion. Hazardous in case of skin contact (irritant, permeator), of
eye contact (irritant), of inhalation.
Potential Chronic Health Effects:
Hazardous in case of skin contact (irritant, permeator), of eye contact (irritant), of inhalation.
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MANUFACTURING OF DMA
CARCINOGENIC EFFECTS: Not available.
MUTAGENIC EFFECTS: Not available.
TERATOGENIC EFFECTS: Not available.
DEVELOPMENTAL TOXICITY: The substance is toxic to blood, kidneys, liver. Repeated or
prolonged exposure to the substance can produce target organs damage
Section 4: First Aid Measures
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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MANUFACTURING OF DMA
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.
Serious Ingestion: Not available.
Section 5: Fire and Explosion Data
Flammability of the Product: Combustible.
Auto-Ignition Temperature: 371°C (699.8°F)
Flash Points: CLOSED CUP: 63°C (145.4°F).
Flammable Limits: LOWER: 1.1%
Products of Combustion: These products are carbon oxides (CO, CO2).
Fire Hazards in Presence of Various Substances: Not available.
Explosion Hazards in Presence of Various Substances:
Risks of explosion of the product in presence of mechanical impact: Not available. Risks of
explosion of the product in presence of static discharge: Not available.
Fire Fighting Media and Instructions:
SMALL FIRE: Use DRY chemical powder. LARGE FIRE: Use water spray, fog or foam. Do
not use water jet.
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MANUFACTURING OF DMA
Special Remarks on Fire Hazards: Not available.
Special Remarks on Explosion Hazards: Not available.
Section 6: Accidental Release Measures
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.
Section 7: Handling and Storage
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.
Section 8: Exposure Controls/Personal Protection
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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MANUFACTURING OF DMA
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
Section 9: Toxicological Information
Routes of Entry: Dermal contact. Eye contact. Inhalation. Ingestion.
Toxicity to Animals: Acute oral toxicity (LD50): 1410 mg/kg [Rat]. Acute dermal toxicity
(LD50): 1770 mg/kg [Rabbit].
Chronic Effects on Humans: The substance is toxic to blood, kidneys, liver.
Other Toxic Effects on Humans: Very hazardous in case of ingestion. Hazardous in case of
skin contact (irritant, permeator), of inhalation.
Special Remarks on Toxicity to Animals: Not available.
Special Remarks on Chronic Effects on Humans: Not available.
Special Remarks on other Toxic Effects on Humans: Not available.
Section 10: Ecological Information
Ecotoxicity: Not available.
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MANUFACTURING OF DMA
BOD and COD: Not available.
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.
Special Remarks on the Products of Biodegradation: Not available.
Section 11: Disposal Considerations
Waste Disposal:
Section 11: Transport Information
DOT Classification: CLASS 6.1: Poisonous material.
Identification: N,N-Dimethylaniline : UN2253 PG: II
Special Provisions for Transport: Not available.
Section 12: Other Regulatory Information
Federal and State Regulations: Pennsylvania RTK: N, N-Dimethylaniline Massachusetts RTK:
N,N-Dimethylaniline TSCA 8(b) inventory: N,N-Dimethylaniline SARA 313 toxic chemical
notification and release reporting: N,N-Dimethylaniline CERCLA: Hazardous substances.:
N,NDimethylaniline
Other Regulations: OSHA: Hazardous by definition of Hazard Communication Standard
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MANUFACTURING OF DMA
(29 CFR 1910.1200).
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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MANUFACTURING OF DMA
CHAPTER 4
APPLICATIONS
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MANUFACTURING OF DMA
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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MANUFACTURING OF DMA
Other Uses:
Specialty industrial solvent and rubber vulcanizing agent.
Reagent in chemical synthesis.
Catalytic hardener in certain fibreglass resins.
N,N-Dimethylaniline is used as an intermediate in the manufacture of dyes, Michler's
ketone and vanilin. It is also used as a specialty industrial solvent, a rubber vulcanizing agent
(see IARC, 1982b, 1987b), a stabilizer and an acid scavenger
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MANUFACTURING OF DMA
CHAPTER 5
MANUFATURING
PROCESSES
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MANUFACTURING OF DMA
1] BY ALKYLATION OF ANILINE:
REACTION:
C6H5NH2 + 2CH3OH →C6H5N(CH3)2 + 2H2O
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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MANUFACTURING OF DMA
CHAPTER 6
PROCESS
DESCRIPTION
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MANUFACTURING OF DMA
6.1 Raw Materials Used
ANILINE
Aniline, phenylamine or aminobenzene is an organic compound with the formula C6H5NH2.
Consisting of a phenyl group attached to an amino group, aniline is the prototypical aromatic
amine. Being a precursor to many industrial chemicals, its main use is in the manufacture of
precursors to polyurethane. Like most volatile amines, it possesses the somewhat unpleasant
odour of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic
compounds. Aniline is colorless, but it slowly oxidizes and resinifies in air, giving a red-brown
tint to aged samples.
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MANUFACTURING OF DMA
PROPERTIES OF ANILINE
Molecular formula:C6H5NH2
Molar mass: 93.13 g/mol
Appearance: colorless liquid
Density : 1.0217 g/mL, liquid
Melting point: -6.3 °C, 267 K, 21 °F
Boiling point: 184.13 °C, 457 K, 363 °F
Solubility in water:3.6 g/100 mL at 20°C
Basicity (pKb): 9.3
Viscosity: 3.71 cP (3.71 mPa·s at 25 °C
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MANUFACTURING OF DMA
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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MANUFACTURING OF DMA
PROPERTIES OF METHANOL
Molecular formula:CH4O
Molar mass : 32.04 g mol−1
Appearance: Colorless liquid
Density: 0.7918 g cm−3
Melting point: -98--97 °C, 175-176 K, -144--143 °F
Boiling point: 65 °C, 338 K, 149 °F
Vapor pressure: 13.02 kPa (at 20 °C)
Acidity (pKa): 15.5[2]
Viscosity: 5.9×10−4 Pa s (at 20 °C)
Dipole moment: 1.69 D
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MANUFACTURING OF DMA
6.2 MANUFACTURING OF DIMETHYLANILINE (DMA) BY
ALKYLATION OF ANILINE
A method for the production of dimethylaniline which consist alkylation of aniline with
use of methanol.
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
At the end of reaction we get dimethylaniline , which we need to purify.
To purify the mixture from autoclave, it is passed through series of vaccum distillation
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MANUFACTURING OF DMA
coloumn. Thus, pure dimethylaniline is formed and passed to further processes and
storage.
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MANUFACTURING OF DMA
6.3 PROCESS FLOW DIAGRAM FOR DIMETHYLANILINE
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MANUFACTURING OF DMA
Bibliography
ROBERT THORNTON MORRISON AND ROBERT NEILSON BOYD,ORGANIC CHEMISTRY,SIXTH EDITION.
JAMES G. SPEIGHT, CHEMICAL AND PROCESS DESIGN HANDBOOK.
Webliography
www.google.com
www.wikipedia.com
www.britannica.com
www.compositesaustralia.com
toxnet.nlm.nih.gov
ScienceLab.com
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