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ETHANOLAMINES

Monoethanolamine DSA9781.qxd 1/31/03 10:21 AM Page 2

CONTENTS

Introduction ...... 2 Applications...... 3 Gas Sweetening ...... 3 Detergents, Specialty Cleaners, Personal Care Products...... 4 Textiles...... 4 Metalworking ...... 5 Other Applications...... 5 Ethanolamine Physical Properties ...... 6 Typical Physical Properties ...... 6 Vapor Pressure of (Figure 1)...... 7 Heat of Vaporization of Ethanolamines (Figure 2)...... 7 Specific Heats of Ethanolamines (Figure 3) ...... 8 Comparative Hygroscopicities of Diethanolamine and Triethanolamine (Figure 4) ...... 8 Weight Percent Ethanolamine in Aqueous Solutions vs Normality of Solution (Figure 5).....9 pH of Ethanolamine Solutions (Figure 6) ...... 9 Partial Pressure of Ethanolamines in Aqueous Solutions at Various Temperatures (Figure 7, 9, 11) ...... 10-12 Vapor- Equilibria of Aqueous Solutions at 760 mm Hg Absolute (Figure 8, 10, 12) ...... 10-12 Absolute of Aqueous Solutions (Figures 13-15) ...... 13 Freezing Points of Aqueous Ethanolamine Solutions (Figure 16)...... 14 Specific Gravity of Aqueous Ethanolamine Solutions (Figure 17) ...... 14 Weight per Gallon of Aqueous Solutions at Various Temperatures (Figures 18-20)...... 15-16 Specific Heats of Aqueous Solutions (Figures 21-23) ...... 17 Storage and Handling ...... 18 Shipping Information ...... 19 Specifications ...... 19 Product Safety...... 19

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ETHANOLAMINES

Dow’s versatile family of ethanolamines — including monoethanolamine (MEA), diethanolamine (DEA), and triethanolamine (TEA) — offers a broad spectrum of application opportunities. Triethanolamine is available as TEA, 99% and TEA, Commercial (which contains nominally 15% diethanolamine). Because ethanolamines combine the properties of and , they exhibit the unique capability of undergoing reactions common to both groups. As amines, they are mildly alkaline and react with to form salts or soaps. As alcohols, they are hygroscopic and can be esterified. The chemical structures of the ethanolamines are:

MEA H2NCH2CH2OH Monoethanolamine DEA HN(CH2CH2OH)2

TEA N(CH2CH2OH)3 Ethanolamines find uses in such diverse areas as gas sweetening, where they serve as lubri- Diethanolamine cants and scouring agents; detergent and specialty cleaner formulations, in which they are used to form various salts and to control pH; and in a host of other applications including concrete admixtures, flexible urethane foam catalysts, pharmaceuticals, personal Triethanolamine care products, agricultural chemicals, photographic , and more. TECHNOLOGY LEADERSHIP Ethanolamines from Dow are backed by approximately 80 years of innovative scientific research. Since their introduction in the late 1920s, MEA, DEA, and TEA have undergone extensive commercial development in our laboratories at South Charleston, WV.

WORLD SCALE PRODUCTION CAPACITY Backed by the world’s largest capacity, Dow’s efficient ethanolamines facilities, located at Seadrift, TX, are the world’s largest. Designed for flexibility, this is capable of producing ethanolamines to meet the most demanding specifications of the marketplace. Additional worldscale ethanolamines facilities were added in 1997 at Taft, LA, and in 2002, at the Optimal joint venture between Dow and Petronas at Kertih, Malaysia. Additional will be added to meet other developing worldwide markets. Dow’s position as the leading producer of basic ethylene oxide and ethanolamines translates into dependability, not only as a source of supply, but in quality of product as well. The purity and consistency of Dow’s ethanolamines are unsurpassed.

BROADEST DISTRIBUTION NETWORK The Dow network of sales personnel, technical service experts, bulk storage terminals, and distributors has been carefully constructed to reach all of Dow’s customers worldwide. Problem solving assistance is virtually a phone call away, and Dow’s vast distribution system assures fast delivery of tanker, barge, tank truck, tank car, or drum quantities from strategically located bulk terminals and warehouses. Whatever your needs in ethanolamines — MEA, DEA, or TEA — Dow has the technical, production, and distribution resources to serve you best. This booklet has been designed to provide the answers to most questions about Dow’s ethanolamine products. For further information contact your Dow representative.

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Ethanolamine Applications

TEA, Typical Applications MEA DEA Commercial TEA, 99%

Adhesives ✗ Agricultural Chemicals ✗✗

Cement Grinding Aids ✗✗ Concrete Additives ✗

Detergents, Specialty Cleaners Personal Care Products ✗✗✗✗

Gas Treating ✗✗✗✗ Metalworking ✗✗✗

Oil Well Chemicals ✗✗✗ Packaging & Printing Inks ✗

Photographic Chemicals ✗✗ Rubber ✗

Textile Finishing ✗✗✗✗ Urethane Foams ✗✗✗

ETHANOLAMINES FOR GAS SWEETENING Aqueous solutions of monoethanolamine and diethanolamine react with dioxide and sulfide at ambient temperature to form compounds that, when exposed to elevated temperatures, release the gas and regenerate the amine for reuse. Monoethanolamine is commonly used for treating synthesis gas streams formed in , hydrogen, carbon monoxide, and facilities. is the principal contaminant that is removed. Diethanolamine is primarily used for treating natural and refinery gas and for liquid streams. Carbon dioxide and are the principal contaminants removed. Engineering companies can provide individually designed plants or standard packaged units that can be installed wherever it is necessary to remove carbon dioxide and/or hydrogen sulfide from gas streams. For natural gas systems and refinery-treating systems in sulfur service, diethanolamine solutions have performed satisfactorily for years in units where carbon steel has been the major material of construction. In improperly designed or improperly operated units, however, corrosion will occur in carbon steel exchangers, condensers, and reboiler-type bundles. In special situations, therefore, alloy materials of construction may be required. In addition, improved design and operating criteria may be specified, including activated carbon filtration and good inlet separation.

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ETHANOLAMINES FOR DETERGENTS, SPECIALTY CLEANERS, AND PERSONAL CARE PRODUCTS Ethanolamines are used in heavy-duty liquid laundry detergents because they provide a unique combination of beneficial property and performance qualities. These ethanolamines impart a reserve alkalinity to the laundry bath, which is essential to efficient cleaning. They neutralize the fatty acids present in the oily soil components and, through this neutralization, convert them to amine soaps. These soaps, in turn, aid in the overall cleaning process. The effect is readily observed when standard industrial oily soils are used. These same ethanolamines are also effective soil anti-redeposition agents. They help to keep soil in the laundry bath from redepositing onto the fabric during the cleaning process. The effect is evident in the performance of nonionic, anionic, and mixed nonionic/anionic -based products on cotton, blended cotton/polyester, and polyester fabrics. Diethanolamine is used to prepare amides, which may be used in various personal care products. Triethanolamine may be reacted with lauryl sulfate to form the foaming base surfactant used in hair . Fatty acids neutralized with ethanolamines, particularly triethanolamine, are excellent emulsifiers for -in-water emulsions. Gel-type industrial hand cleaners, aerosol shave creams, and hand and body are only a few of the consumer products commonly formulated with such soaps. Triethanolamine is also used as the base component in the production of certain mild bar soaps.

ETHANOLAMINES FOR TEXTILES Ethanolamines are used in textile processing as reaction intermediates for the preparation of durable press fabric finishes and softeners. Amine soaps are used as scouring agents for wool and silk because of their low alkalinity. Ethanolamines are also used as dye auxiliaries. Because of their hygroscopicity, ethanolamines find application in the preparation of vat printing pastes. Diethanolamine and triethanolamine are used in making acetate rayon dyes. Textile lubricants often incorporate salts of ethanolamines to benefit from their anticorrosion and antistatic properties. Ethanolamine salts of mono- or di-phosphates, sulfonates, and sulfates are typical components of staple finishes.

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ETHANOLAMINES FOR METALWORKING Acidic additives and/or acidic decomposition products are the prime contributors to corrosion of metal surfaces, particularly in the presence of moisture. Ethanolamines are often used as neutralizers of acid components in lubricants and are a time-tested means of preventing corrosion. In water-soluble cutting and grinding fluids, ethanolamines are used to provide the alkalinity needed to protect against rusting (ferrous metals do not oxidize under alkaline conditions). Ethanolamines are also used as intermediates in the preparation of water-soluble lubricants, emulsifiers, proprietary corrosion inhibitors, and biocides.

OTHER ETHANOLAMINE APPLICATIONS In addition to supplying ethanolamines for the four major applications already discussed, Dow provides these versatile materials for a variety of other uses (See Applications Chart, page 3). Diethanolamine and triethanolamine are used as catalysts that promote stability during the reaction process in the manufacture of flexible and rigid urethane foams. In the photographic chemical industry, these ethanolamines find application in complex modern developing systems. Diethanolamine and triethanolamine are used in the agricultural chemical field as intermediates in a number of applications, most notably the manufacture of herbicides. Triethanolamine finds use as an intermediate for additives that control the rate at which water evaporates from drying concrete. In another application, triethanolamine is used as a compo- nent in the formulation of cement grinding media during the manufacture of cement. In still another important use, triethanolamine is utilized “down hole” in oil wells to prevent corrosion of drilling equipment. Triethanolamine also functions as an intermediate for adhesive and rubber chemicals. Mono- ethanolamine is used as a pH control agent in the formulation of packaging and printing inks. Triethanolamine (Trolamine 99% NF Grade) meets the requirements of the applicable National Formulary monograph.

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Typical Physical Properties

The properties of Dow’s family of ethanolamines enable these versatile materials to be utilized in a broad range of applications. Typical properties of the ethanolamines are shown in the table below and in Figures 1-23. Table 1 • Typical Properties of DOW Ethanolamines Monoethanolamine Diethanolamine Triethanolamine

Formula H2NCH2CH2OH HN(CH2CH2OH)2 N(CH2CH2OH)3 Molecular Weight 61.08 105.14 149.19 Apparent Sp. Gr. at 20/20°C 1.017 1.092(a) 1.126(f) ∆Sp. Gr./∆t at 10 to 80°C 0.00080 0.00065(b) 0.00059 Boiling Point at 760 mm Hg, °C 170.4 268(c) 335(c) at 50mm Hg, °C 101 182 245(c) at 10mm Hg, °C 71 150 205 Vapor Pressure at 20°C, mm Hg <1 <0.01 <0.001 Freezing Point, °C(°F) 10.5 (50.9) 28.0 (82.4) 21.6 (70.9)(e) Absolute at 20°C, cP 24.1 — 921(f) at 30°C, cP 16.2 380 404 at 20°C, % by wt In Water Complete Complete(f) Complete(f) Water In Complete — Complete(f) Solubility in Organic at 25°C, % by wt Acetone Complete Complete(f) Complete Benzene 0.6 0.03 2 Carbon Tetrachloride 0.1 0.01 Complete Ethyl Ether 0.7 0.5 2 Heptane 0.1 0.03 <0.03 Methanol Complete Complete(f) Complete Surface Tension, dynes/cm 48.3(d) 48.5(g) 48.9(d) 20 (g) (f) , nD 1.4539 1.4747 1.4852 ∆ ∆ (b) ND/ t at 20 to 40°C per °C 0.00034 0.00027 0.00020 Flash Point, °C (°F) 96 (205)(h) 191 (375)(h) 208 (407)(h) (a) At 30/20°C (e) Supercools easily (b) At 35 to 65°C (f) Supercooled liquid (c) Extrapolated (decomposes) (g) At 30°C (d) At 25°C (h) Determined by ASTM Method D 93, using the Pensky-Martens Closed Cup

NOTE This table sets forth typical properties of Monoethanolamine, Diethanolamine, and Triethanolamine based upon analysis(ses) of commercial product or purified sample, etc.; however, Dow does not analyze each shipment of product for all of these properties. Dow warrants only that, at the time of delivery, product will conform to Dow’s standard specifica- tions as then in effect.

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Figure 1 Vapor Pressure of Ethanolamines Temperature, °F 70 90 120 160 200 240 320 400 480 1000 800 600 500 400 300 200

10 0 80 60 50 40 30 20 Note: Ethanolamines begin MEA DEA decomposing at temperatures TEA above about 200°C and can 10

undergo self-sustained Pressure, mm Hg Vapor 8 6 decomposition at temperatures 5 above 250°C. 4 3 2

1 20 40 60 80 120 160 200 240 Temperature, °C Figure 2 Heat of Vaporization of Ethanolamines Temperature, °F 150 250 350 450 550 650 440

410 MEA 380

350

320 DEA 290

260 Heat of Vaporization, Btu/lb* Heat of Vaporization, *1 Btu/lb = 0.56 cal/g TEA 230

200 50 100 150 200 250 300 350 Temperature, °C 7 DSA9781.qxd 1/31/03 10:21 AM Page 9

Figure 3 Specific Heat of Ethanolamines Temperature, °F 40 80 120 160 200 240 280 320 360 0.84 0.82 0.80 0.78 0.76 MEA 0.74 0.72 DEA 0.70 0.68 TEA 0.66 0.64 Specific Heat, Cal/g-°C 0.62 0.60 0.58 0.56 0.54 0 20 40 60 80 100 120 140 160 180 200 Temperature, °C Figure 4 Comparative Hygroscopicities of Diethanolamine and Triethanolamine from 75° to 80°F

100 80 60 DEA 40 TEA

20

10 8 6

4

Percent Gain in Weight at Equilibrium Percent Gain in Weight 2

1 10 20 30 40 50 60 70 80 Relative Humidity, % 8 DSA9781.qxd 1/31/03 10:21 AM Page 10

Figure 5 Weight Percent Ethanolamine in Aqueous Solutions vs Normality of Solution

70 TEA DEA 60 MEA

50

40

30

20

Amine, Percent by Weight in Solution Amine, Percent by Weight 10

0 0 3 6 9 12 15 Normality of Amine Solution Figure 6 pH of Ethanolamine Solutions

40

20 TEA, 99%

10 TEA, Commercial 4 2 1 DEA MEA .4 .2

Amine, Percent by Weight .1

.04 .02 .01 8 9 10 11 12 13 pH at 20°C 9 DSA9781.qxd 1/31/03 10:21 AM Page 11

Figure 7 Partial Pressure of Monoethanolamine in Aqueous Solutions at Various Temperatures Temperature, °F 40 60 80 100 120 10 MEA % by wt

100 1 95 90

80 0.1 60 40 30 20 0.01 10 5

10-3 Partial Pressure of Monoethanolamine, mm Hg

10-4 01020304050 Temperature, °C Figure 8 Vapor-Liquid Equilibria (T-x-y) of Aqueous Monoethanolamine Solutions at 760 mm Hg Absolute

180

170 340

160 320 Vapor Phase 150 300

140 280 130 260 120 Temperature, °C Temperature, 240 °F Temperature, 110 220 100 Liquid Phase 200 90 180 80 0 102030405060708090100 Monoethanolamine, Percent by Weight 10 DSA9781.qxd 1/31/03 10:21 AM Page 12

Figure 9 Partial Pressure of Diethanolamine in Aqueous Solutions at Various Temperatures Temperature, °F 60 80 100 120 140 0.1 DEA % by wt

0.01 100 95

10-3 80

60

40 10-4 20 10 10-5 5 Partial Pressure of Diethanolamine, mm Hg

10-6 15 20 25 30 35 40 45 50 55 60 65 70 Temperature, °C Figure 10 Vapor-Liquid Equilibria (T-x-y) of Aqueous Diethanolamine Solutions at 760 mm Hg Absolute

275 495 255 Vapor Phase 235 455

215 415

195 375

175 335 155 Temperature, °C Temperature, 295 °F Temperature, 135 255 115 Note: Ethanolamines can Liquid Phase 215 undergo decomposition 95 at temperatures above 175 approximately 200°C 75 0 102030405060708090100 Diethanolamine, Percent by Weight 11 DSA9781.qxd 1/31/03 10:21 AM Page 13

Figure 11 Partial Pressure of Triethanolamine in Aqueous Solutions at Various Temperatures Temperature, °F 120 140 160 180 200 0.1 TEA % by wt

0.01 100 95

10-3 80

60 10-4 40 20 10-5 10 5

10-6 Partial Pressure of Triethanolamine, mm Hg Partial Pressure of Triethanolamine,

10-7 45 50 55 60 65 70 75 80 85 90 95 100 Temperature, °C Figure 12 Vapor-Liquid Equilibria (T-x-y) of Aqueous Triethanolamine Solutions at 760 mm Hg Absolute

380 360 680 340 640 320 600 300 Vapor Phase 560 280 520 260 480 240 440 220 200 400 Temperature, °C Temperature, 180 360 °F Temperature, 160 320 140 280 Note: Ethanolamines can 120 undergo decomposition 240 100 at temperatures above Liquid Phase 200 approximately 200°C 80 0 102030405060708090100 Triethanolamine, Percent by Weight 12 DSA9781.qxd 1/31/03 10:21 AM Page 14

Figure 13 Absolute Viscosity of Aqueous Monoethanolamine Solutions

100 60 40 20 1 10 2 6 4 3 2 4 1 30°C (86°F) 1 2 50°C (122°F) 0.6 3 75°C (167°F) 0.4 4 100°C (212°F) 0.2

Absolute Viscosity, Centipoise Absolute Viscosity, 0.1 0 102030405060708090100 Monoethanolamine, Percent by Weight

Figure 14 Absolute Viscosity of Aqueous Diethanolamine Solutions

1000 400 200 1 100 40 2 20 3 10 4 4 1 30°C (86°F) 2 2 50°C (122°F) 1 3 75°C (167°F) 0.4 4 100°C (212°F) 0.2

Absolute Viscosity, Centipoise Absolute Viscosity, 0.1 0 102030405060708090100 Diethanolamine, Percent by Weight

Figure 15 Absolute Viscosity of Aqueous Triethanolamine Solutions

1000 400 200 1 100 40 2 20 3 10 4 4 1 30°C (86°F) 2 2 50°C (122°F) 1 3 75°C (167°F) 0.4 4 100°C (212°F) 0.2

Absolute Viscosity, Centipoise Absolute Viscosity, 0.1 0 102030405060708090100 Triethanolamine, Percent by Weight

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Figure 16 Freezing Points of Aqueous Ethanolamine Solutions

60 140

120

40 100

80 20 Triethanolamine 60

40 0 Diethanolamine 20 Freezing Point, °F Freezing Point, °C -20 0 -20

Note: Freezing point data -40 -40 for 70% to 90% Diethanolamine in water are Monoethanolamine -60 extrapolated -60 0 20 40 60 80 100 Ethanolamine, Percent by Weight Figure 17 Specific Gravity of Aqueous Ethanolamine Solutions at 20/20°C

1.13 1.12 1.11 Triethanolamine 1.10 1.09 Freezing 1.08 Point 1.07 1.06 Diethanolamine 1.05 1.04 Specific Gravity, 20/20°C Specific Gravity, 1.03 1.02 Monoethanolamine 1.01 1.00 0 102030405060708090100 Ethanolamine, Percent by Weight 14 DSA9781.qxd 1/31/03 10:21 AM Page 16

Figure 18 Weight per Gallon of Aqueous Monoethanolamine Solutions at Various Temperatures

9.2

Freezing Point Curve 9.0

0°F 8.8 30°F 60°F 8.6 90°F 120°F 8.4 150°F

Pounds per Gallon 180°F 8.2 210°F

8.0

7.8 0 20 40 60 80 100 Monoethanolamine, Percent by Weight Figure 19 Weight per Gallon of Aqueous Diethanolamine Solutions at Various Temperatures

9.4 Freezing Point Curve -20 °F 9.2 0 °F 30°F 60°F 9.0 90°F 120°F 150°F 8.8 180°F 210°F 8.6 240°F Pounds per Gallon 8.4 Boiling Point 8.2

8.0 0 20 40 60 80 100 Diethanolamine, Percent by Weight 15 DSA9781.qxd 1/31/03 10:21 AM Page 17

Figure 20 Weight per Gallon of Aqueous Triethanolamine Solutions at Various Temperatures

9.6 Freezing Point Curve 9.4 30°F 0°F 60°F 90°F 9.2 120°F 150°F 180°F 9.0 210°F 240°F 8.8

8.6

Pounds per Gallon 8.4 Boiling Point 8.2

8.0

7.8 0 20 40 60 80 100 Triethanolamine, Percent by Weight

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Figure 21

Specific Heats of Aqueous Monoethanolamine Solutions Temperature, °F 40 80 120 160 200 240 1.1 MEA % by Wt 1.0 0

0.9 25

Cal/g-°C 0.8 50 75 0.7 100 0.6 0 20 40 60 80 100 120 Temperature, °C

Figure 22 Specific Heats of Aqueous Diethanolamine Solutions Temperature, °F 40 80 120 160 200 240 1.1 DEA % by Wt 1.0 0

0.9 25

Cal/g-°C 0.8 50

0.7 75 100 0.6 0 20 40 60 80 100 120 Temperature, °C

Figure 23

Specific Heats of Aqueous Triethanolamine Solutions Temperature, °F 40 80 120 160 200 240 1.1 TEA % by Wt 1.0 0 0.9 25 0.8 50 Cal/g-°C 0.7 75 0.6 100 0.5 0 20 40 60 80 100 120 Temperature, °C

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Storage and Handling

Proper storage and handling will help maintain the quality of ethanolamine products. Under normal conditions ethanolamines are considered to be thermally stable and are not corrosive to the proper containers. However, they are sufficiently reactive that upon exposure to adventitious carbon dioxide, nitrogen oxides, and , trace levels of byproducts can form and increased color often results. For storage and handling information contact your Dow representative.

SAFETY NOTE — MONOETHANOLAMINE Monoethanolamine in contact with iron can form a crystalline complex called tris(ethanolamino)-iron. This compound can ignite when heated to 130-160°F (54-71°C) in the presence of air. A fire is known to have occurred in a storage tank equipped with a carbon steel heating coil using 150 psig steam. For internal steam applications, stainless steel heating coils should be used; low-pressure steam is preferred for safety and product quality.

STORAGE TEMPERATURES Ethanolamines require heated and insulated storage and transfer facilities. Ethanolamines darken, however, at temperatures above 140°F (60°C). Table 2 • Storage Temperatures for Ethanolamines Approximate Freezing Storage Viscosity, cP, Point, °C (°F) Temperature, °F 30°C (86°F) Monoethanolamine 10.5 (50.9) 65-95 15 Diethanolamine 28.0 (82.4) 95-120 380 Triethanolamine, Commercial 15.8 (60.4) 75-110 400 Triethanolamine, 99% 21.6 (70.9)(a) 85-110 400 (a) Supercools easily

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Shipping Information

For your convenience in ordering, Dow markets ethanolamines both direct and through an effective network of distributors. Less than full tank car or tank truck quantities can be delivered most rapidly through a Dow distributor. Consult your Dow representative for the name of the distributor nearest you. For delivery of large volume orders, ethanolamines are stocked in terminals throughout the world. Table 3 • Shipping Data for Ethanolamines Monoethanolamine Diethanolamine Triethanolamine, Triethanolamine, Commercial 99% Pounds per Gallon at 20°C 8.47 9.10 (30°C) 9.37 9.38 Kilograms per liter at 20°C 1.015 1.088 (30°C) 1.123 1.124 Coefficient of Expansion 0.00081 0.00060 0.00049 0.00053 at 55°C, per °C Flash Point, °C (°F)(a) 96 (205) 191 (375) 194 (382) 208 (407) (a) Determined by ASTM Method D 93, using the Pensky-Martens Closed Cup

Specifications

Specifications for DOW Ethanolamines are available on request from your Dow sales representative.

Product Safety When considering the use of any Dow products in a particular application, you should review Dow’s latest Material Safety Data Sheets and ensure that the use you intend can be accomplished safely. For Material Safety Data Sheets and other product safety information, please contact us using the numbers on the back cover of this brochure. Before handling any other products mentioned in the text, you should obtain available product safety infor- mation and take necessary steps to ensure safety of use. No chemical should be used as or in a food, drug, medical device, or cosmetic, until the user has determined the suitability and legality of the use. Since government regulations and use conditions are subject to change, it is the user’s responsibility to determine that this information is appropriate and suitable under current, applicable laws and regulations. Dow requests that the customer read, understand, and comply with the information contained in this publication and the current Material Safety Data Sheet(s). The customer should furnish the information in this publication to its employees, contractors, and customers, or any other users of the product(s), and request that they do the same.

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Published January 2003 *

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