Manufacture of ADMT

MANUFACTURE OF 2-AMINO DIMETHYL TERAPHTALATE

GROUP MEMBERS TANUJAKUNIKA

PROJECT GUIDE PROF. S.S. MUJUMDAR

ACKNOWLEDMENT

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We take this opportunity to express my profound gratitude and deep regards

to my guide “PROF.S.S.Mujumdar” sir for his exemplary guidance, monitoring

and constant encouragement throughout the course of this thesis. The

blessing, help and guidance given by him time to time shall carry me a long

way in the journey of life on which I am about to embark.

I am obliged to staff members of chemical engineering department for the

valuable information provided by them. I am grateful for their cooperation

during the period of my assignment.

We are sincerely thank mrs.neelam kevalramani for her support in completing

this project

Lastly, I thank library staff and other staff of chemical engineering for their

constant encouragement without which this assignment would not be

possible.

Index

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SR NO

CONTENT PAGE NO

1 ACKNOWLEDGEMENT 22 HISTORY 43 INTRODUCTION 84 PROPERTIES 105 CHEMICAL REACTION 116 REACTOR 127 FLOWHEET 138 BLOCK DIAGRAM 149 MASS BALANCE 1510 ENERGY BALANCE 2311 BIBILIOGRAPHY 32

History of ADMT

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ADMT is used in the manufacture of polyester fibre yarn and film and also certain polyester resins. Of these, polyester fibre and yarn account for a major portion of ADMT used. ADMT production in the world commenced as early as 1949 in England, whereas in India the first ADMT plant was set up in 1973 by Indian Petrochemical Corporation Limited (IPCL) at present there are three (3) major producers of ADMT in India with a total installed capacity of 1,35,000 TPY (Indian Petrochemical Corporation Limited - 30,000, Refinery & Petrochemicals Limited - 45,000, Bombay Dyeing & Manufacturing Company Limited-60,000).

The targeted production for 1985-86 was 55,000 TPY because two of the units i.e. BRPL and BDML commenced production during 1985 only. The two main raw materials required for ADMT manufacture are p-xylem and methanol. For p-xylem, IPCL and BRPL have production capacity of 46,000 TPY which is not adequate to meet the demand of the installed ADMT production capacity. Therefore, p-xylem is being imported to meet the short-fall.

The total methanol capacity on the other hand, shared between four (4) units is 81,000 TPY. Additional capacity of 5,31,000TPY is covered by licences and with the progress of their implementation the total installed capacity would be adequate to meet the projected demand for polyester during the VII Five Year Plan. In this process a mixture of p-xylem and recycled p-methyl tolerate is oxidized catalytically with air to produce p-telic acid and terephthalate.

These acids are with methanol into p-methyl tolerate and ADMT. Crude ADMT obtained is purified by crystallization and distillation.

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The major items of equipment in a ADMT plant i.e. Oxidator, etherification columns, machine, centrifuge, special purpose pumps and spares have been imported.

The foreign exchange component of the total investment is reported as 44% for IPCL, BRPL and process licensors are Nobel AG Krupp-Kippers GmbH and Hercufina’s respectively. The agreements generally include know-how, basic engineering design as well as supply equipment, supervision of erection and start-up for a total payment. (EIL) and Tata Consulting Engineers (TCE).

EIL had rendered services towards detailed engineering for plant, procurement and construction services for off-site facilities for both IPCL and BRPL, TCE were associated in the supervision of dismantling of Hercufina's plant, design and engineering procurement, inspection and expediting, construction, supervision, project management, start-up and commissioning for BDML. Apart from these, a number of local equipment suppliers and contractors had rendered their services covering civil, mechanical, piping, electrical and instrumentation jobs for these projects.

In the international scene, the majority of ADMT plants in operation are based on Witten process. However, the production capacities are much higher, viz. 200 to 500 TPD. All the development work relating to ADMT is being carried out by IPCL, being the oldest unit in production. The research and development centre at IPCL has been active in examining steps on ADMT production. In terms of indigenisation of capital goods, IPCL has introduced technological

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improvement in ADMT manufacture with the commissioning of horizontal oxidator for the first time in the world. Efforts are still being made to further improve this.

The national institution/laboratories have yet to make any significant contribution in effecting improvement in ADMT technology in the country. Due to the development of a production process for high purity fibre grade terephthalic acid its share in polyester fibre production has been increasing steadily and, at present, accounts for over 50% internationally.

In India, following the international trend, the production facility for purified terephthalic acid (PTA) is being created and more new units are competing for it. Any new capacity to be set up in India is likely to be for PTA rather than ADMT. There is however, scope for carrying out improvements in existing units and the following recommendations are made:

There is no need for any further import of technology for production of ADMT The in-house development work should be continued to improve the efficiency and quality with a view to reduce the cost of production. The existing manufacturers of ADMT may consider developing the process and facilities to make pure terephthalic acid from their ADMT plants so that they are able to meet the fluctuating demand of these two raw-materials. A co-ordinated effort by three units, in which the resources pooled and the costs shared would accelerate this development. Considering the importance of this development, financial assistance as required should be provided

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and R & D programmes approved to accelerate the development. While the bulk of the equipment in the existing plants was imported at the time of their setting up, for future projects it should not be necessary. Import of equipment that can be produced in India, should not be allowed. Production facilities should be established for the manufacture of p-xylem to meet the demand for ADMT and PTA manufacture.

Introduction

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Chemical name – 2 amino dimethyl terephthalate

Molecular structure –

Dye intermediate as intermediates for a variety of aromatic compounds, refers to the production of dyes and organic pigments. They are since the coal chemical industry and petroleum chemical benzene, toluene, naphthalene and anthracite aromatic as raw material, through a series of organic synthesis unit process (see the reaction process) process.

With the development of chemical industry, the scope of application of dye intermediates has been extended to the pharmaceutical industry, pesticide industry, explosive industry, information recording materials industry, the production department and additives, surface active agent, spice, plastics, synthetic fibber etc.. A lot of dye intermediate species, the more important it has hundreds of.

The most important early dye intermediates, such as nitrobenzene, aniline, phenol, ophthalmic anhydride, chlorobenzene and two, because of wide usage, dosage, has developed into a basic important organic intermediates, the world annual production of over 1 million tons. Now the most important of the dye intermediates o-, p-, o-

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nitrotoluene,P-nitrotoluene,2- naphthol1- , etc.. Starting from these intermediates, after a series of organic synthesis unit process, and can prepare intermediate complex structure.

ADMT is manufactured from NDMT which is basically used in the manufacturing of dyes .it also known as dyes intermediate Dye intermediate mainly benzene , naphthalene intermediates and intermediate of series four categories, in addition, there are some heterocyclic intermediates.

The production of intermediates used in reaction process mainly includes Nitrification, suffocated, , reduction, , hydrolysis, oxidation, condensation. Intermediate for the synthesis of a complex, often have to go through many unit processes, sometimes using the basic raw material and different synthetic routes. For , initially with benzene nitration, reduction and acetyl aniline, synthetic route, nitration, hydrolysis, the production process, high cost.

Now instead of Benzene Chlorination, nitration, from p-, synthetic route of high pressure ammonia solution. For intermediates in manufacturing dyes, pesticides or medicine, usually complicated structure, often and final products supporting the production, production of smaller, the use of batch production. Some intermediates widely used, such as nitrobenzene, aniline, phenol and chlorobenzene, such as production, usually, in a comprehensive large-scale chemical plant production, production of continuous operation.

Properties of ADMT

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Chemical name dimethyl amino terephthalate

Molecular formula C10 H11NO4

Molecular weight 209.2

Melting point 132 0c

Boiling point 327

Appearance beige to brown powder

Partition coefficient 87

Chemical property slightly yellow crystalline powder

Chemical reactions involved

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Reactor

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Block diagram

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Mass and energy balance

A mass balance ( also called material balance ) is an application of conservation of mass to the analysis of physical system

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Raw material used in ADMT

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NDMT

2 – nitro dimethyl terephthalate that is extensively known as pharmaceutical intermediate used in different pharmaceutical application

Structure

Formula = C10 H9 NO6

Molecular weight = 239.18

Melting point = 73oc

Density = 1.272

Water solubility = insoluble

Chemical property = white powder

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Monochlrobenzene

Structure

Formula = C6H5CL

Molecular weight = 112.56

Physical appearance = clear colourless liquid

Specific gravity = 1.099 at 27 oc

Solubility = insoluble in H2O , soluble in organic compounds

Application

It is used as a raw material in chemical industry

It is used in manufacturing of phenol, aniline, solvent for paint and heat transfer media

Manufacturing of ADMT

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Sulphuric acid (H2SO4)

Structure

Formula = H2SO4

Density = 1.84 g/cm3

Molecular weight = 98.079 g/mol

Boiling point = 337 o c

Melting point = 10 °C

Solubility in water = miscible

It is highly corrosive strong mineral acid

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Acetic acid

Structure

Formula = CH3COOH

Molecular weight = 60.05 g/mol

Density = 1.05 gm/cm3

Boiling point = 118 o c

Melting point = 16 o c

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Acetic acid is a chemical reagent for the production of chemical

compounds. The largest single use of acetic acid is in the production

of vinyl acetate monomer, closely followed by acetic anhydride and

ester production. The volume of acetic acid used in vinegar is

comparatively small

1. It is an organic compound

2. It is colourless liquid when undiluted it is called glacial acetic

acid

3. Acetic acid is used in vinyl acetate monomer

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Iron powder

Atomic number = 26

Atomic weight = 55.845 G/mol

Density = 7.874 g/cm3

Melting point = 1538

Boiling point = 2862

Application

Iron powder is used in powder metallurgy of iron steel and in

combination with other metals they are used in great quantities in

the automotive industry as well as in ferromagnetism

Iron powder is used in soil remediation and water purification

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Material balance

Basis :

385 kg/day of AADMT produced

Since we know

500 kg of NADMT =========== 385 kg of AADMT

Then per day our production from reactor = 346 kg/day

500 = 385

? = 346

X = 449.3506 kg of NADMT will be required per day

In the reactor

Basis :

200 litres of mono chlorobenzene is added

Assume 1 litre = 1 kg

200 litres of MCB = 385 kg/day

9 (Y) = 346 kg/day

Then

Y = 179.74 litres of MCB will be required

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Basis

25 litre of acetic acid is added for 385 kg of AADMT

25 litre = 385 kg/day

(Z) = 346 kg/ day

Z = 22.46 litres of acetic acid is required

Basis :

25 kg of iron powder is required for 385 kg of AADMT

Then ,

25 kg = 385 kg

? (P) = 346 kg /day

P = 22.46 of iron powder will be required

Basis :

120 litres of H2O = 385

Q = 346

Q = 107.84 litres of H2O will be required per day

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Molecular weight

1) NADMT = C10H9NO6 = 239.192) MCB = C6H5CL3) Acetic acid = CH3COOH =60.054) H2O= 185) Iron powder = 55.845

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1. NDMT Kmol = weight ----------------------- Molecular weight

449.35/239.19 = 239.19

2) MCB Kmol = 179.74/112.56 = 1.59 Kmol

3) ACETIC ACID = 22.46/60.05 = 0.37 kg/mol

4) IRON powder =22.46/55.84 = 0.044 kg/mol

5) H2O= 107.84/18= 5.991 kg/mol

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Energy balance

Q = M cp Δ T

= M x cp x (T2 – T1)

Here

T2 = 85 o c

T1 = 25 o c

M = mass of reactant

= 2670 kg

Cp = average Cp of reactant

= 0.8075 kcal/ kgoc

Q = 0.8075 x 2670 (85 – 25)

= 129361.5 kcal

Amount of heat removal while cooling

Q = M x Cp x Δ T

M = mass of products

= 2055.9 kg

Cp = average Cp of product

= 0.2818 kcal/ kgoc

Q = 2055.9 x 0.2818 x (85 – 25)

= 34761.1572 kcal

HEAT OF REACTION = HF (products ) – HF ( reactants )

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NDMT

SubstanceNitro dimethyl terephthalate C10H9NO6

304.26

Acetic acid CH3COOH - 108.75

Iron Fe - 57.15

Mono chloro benzene C6H5CL 7.5

Sodium bicarbonate NaHCO3 -222.1

ADMT C10H11NO4 -197.2

H2O - 68.315

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Heat of reaction

HR = 1 ( - 197.2) + 1 ( 304.26)

= - 504.46 kcal/mol

Reaction is exothermic

HR = HF (product) – HR (Reactants) + Cp + d T

Cp of product = 0.0590 Kcal/Gmol o C

= - 501.46 + 0.0590 x (85 – 25) = - 497.92 Kcal/mol

Feed rate of NADMT = 500/239.19

= 2.29 mole

Feed rate of acetic acid = 25/60.05

= 0.416 mole

Feed rate of water = 120/18

= 6.66 mole Feed rate of MCB = 200/112.56

= 17.76

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Feed rate of Iron = 25/55.845

= 0.44

Feed rate of sodium bicarbonate

= 65/89

=0.730

Total molar flow rate of reactant = 2.29 + 0.416 + 6.66 + 17.76 + 0.730 = 28.29 kmoles/batch

Heat flow = heat of reaction x molar flow rate of feed

= - 501.46 x 28.29

= - 14189.31216 kcal

Since the reaction is exothermic the reaction temperature is

maintained constant by circulating cold water through jacket

We have,

Heat evolved during reaction = heat gained by cold water

Q = M cp Δ T

Cp = 1 kcal/kgoc

Δ T = temperature gradient

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Inlet temp of cold water = 25 o c

Outlet temp of hot water = 40 o c

= -14189.31216 = m x 1 x ( 40 - 25 )

= -14189.31216 = m x 15

= -14189.31216/15 = m

= -945.95 kg/batch = m

Total water requirement is 945.95 kg/batch

Manufacture of ADMT

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