Contents Introduction ............................................3 Product Profiles.......................................4 Ethylenediamine (EDA).........................4 Diethylenetriamine (DETA) ..................4 Triethylenetetramine (TETA) ................4 Tetraethylenepentamine (TEPA) ..........4 Heavy Polyamine (HPA) ........................5 Piperazine (PIP)......................................5 Aminoethylpiperazine (AEP) ................5 Aminoethylethanolamine (AEEA) ........5 Typical Physical Properties ....................6 Ethyleneamines Vapor Pressure vs. Temperature ........8 Viscosity vs. Temperature...................9 Specific Gravity vs. Temperature .....10 Ethylenediamine Aqueous Solutions Freezing Point vs. Composition.......11 Vapor-Liquid Equilibria at 760 mm Hg ................................12 Heat of Solution at 22°C ...................13 Specific Gravity vs. Temperature .....14 Piperazine Aqueous Solutions Freezing Point vs. Composition.......15 Vapor-Liquid Equilibria at 760 mm Hg ................................16 Reactions of Ethyleneamines...............17 Reaction Notes ......................................18 Ethyleneamines Applications ..............20 Major End-Uses....................................21 Lubricant and Fuel Additives..............22 Polyamide Resins .................................23 Asphalt Additives and Emulsifiers.......24 Petroleum Production and Refining....24 Resins and Additives for Pulp and Paper .....................................25 Epoxy Curing Agents............................26 Bleach Activators..................................26 Chelates and Chelating Agents...........27 Metal Ore Processing ...........................27 Surfactants and Emulsifiers ................28 Anthelmintics (Dewormers) ...............28 Fabric Softeners....................................29 Fungicides.............................................30 Textiles...................................................31 Polymers and Elastomers....................31 Other Applications ...............................31 Shipping Data........................................32 Product Specifications..........................32 Product Availability...............................33 Storage and Handling ...........................34 Health Effects ........................................35 Ecological Fate and Effects...................36 Product Safety .......................................37 FDA Status .............................................38 References .............................................40 Emergency Service................................47 2 Introduction he Dow Chemical Company, pioneered ethyleneamines development in 1935, when the company was the first to commercialize production, and has been the acknowledged world leader in the business ever since. Today, Dow manufactures ethyleneamines in two world-scale facilities at its Taft, Louisiana, petrochemicals complex. We are the only producer to use both the ethylene dichloride and reductive amination catalytic processes, thus providing unparalleled flexibility in meeting customer needs. Unexcelled quality – in product, technology, and services – is the byword of Dow’s ethyleneamines business. Another first for the company was receipt of ISO 9002 registration in 1990 for the Taft quality systems. Since then, registrations have been received for raw material quality systems, including those for ethylene, ethylene oxide, and ethanolamines, as well as for domestic and international distribution systems. In 1994, our ethyleneamines business won the Shingo Prize for Excellence in Manufacturing. The award recognizes outstanding achievements in manufacturing processes, quality enhancement, productivity improvement, and customer satisfaction. Helping to drive these evergreen quality programs is Dow’s technology leadership. Dedicated research and development focused on the ethyleneamines production processes has constantly improved product quality. Manufacturing technicians employ advanced statistical process control and zone charting for continuous improvement and reduced variability. Backing them is the in-plant laboratory with dedicated equipment for each of the ethyleneamines covered in this publication. And our applications scientists, unsurpassed in their knowledge of ethyl-eneamine end uses, are always ready to assist customers with their needs. Dow’s worldwide distribution network assures you of a readily available source of ethyleneamines. T 3 Product Profiles Ethylenediamine (EDA) (1,2-diaminoethane) is the lowest molecular weight member of the ethyleneamines family. It contains two primary amine groups and forms a maximum boiling azeotrope with water. H2NCH2CH2NH2 EDA is used primarily as an intermediate in the production of bleach activators, fungicides, chelating agents, plastic lubricants, textile resins, polyamides, and fuel additives. Diethylenetriamine (DETA) is the second linear member of the ethyleneamines family. It contains two primary and one secondary amine groups. Compared to ethylenediamine, DETA exhibits a broad liquid range: 207°C (405°F) boiling point at 760 mm Hg and -39°C (-38°F) freezing point. H2NCH2CH2NHCH2CH2NH2 DETA is used primarily as an intermediate to manufacture wet-strength paper resins, chelating agents, ion exchange resins, ore processing aids, textile softeners, fuel additives, and corrosion inhibitors. Triethylenetetramine (TETA) is a liquid containing linear, branched, and cyclic molecules. The principal tetramine structures are: H2NC2H4NHC2H4NHC2H4NH2 (H2NC2H4)3N HN NC2H4NHC2H4NH2 H2NC2H4N NC2H4NH2 Linear TETA Tris-aminoethylamine (TAEA) Piperazinoethylethylenediamine (PEEDA) Diaminoethylpiperazine (DAEP) (Bis-aminoethylpiperazine) The major applications of TETA include epoxy curing agents, and the production of polyamides and oil and fuel additives. Tetraethylenepentamine (TEPA) is a mixture containing linear, branched, and cyclic molecules. The structures of the major TEPA components are: H2NC2H4NHC2H4NHC2H4NHC2H4NH2 H2NC2H4NHC2H4N(C2H4NH2)2 H2NC2H4NHC2H4N NC2H4NH2 HN NC2H4NHC2H4NHC2H4NH2 Linear TEPA Aminoethyltris-aminoethylamine (AE-TAEA) Aminoethyldiaminoethylpiperazine (AE-DAEP) Aminoethylpiperazinoethylethylenediamine (AE-PEEDA) Among the major end-uses for TEPA are the preparation of oil and fuel additives, reactive polyamides, epoxy curing agents, and corrosion inhibitors. 4 HN NC2H4NH2 Major end-uses for AEP include the production of urethane catalysts. combine the features of an ethyleneamine and an ethanolamine. and one tertiary nitrogen atom. H2NC2H4NHC2H4OH Principal end-uses include surfactants. HN NH Among the major applications for PIP are anthelmintics. commercial piperazine is often sold in aqueous solutions to facilitate handling and storage. branched. an anhydrous piperazine is available in flake form. one secondary. The structures of the principal components contain six or more nitrogen atoms per molecule. and as an intermediate for the production of triethylenediamine polyurethane catalyst. polyamides. corrosion inhibitors. In addition. The product has two secondary amine groups.4 °F). epoxy curing agents. fuel additives. The primary and secondary amine groups. Anhydrous PIP has a fairly high freezing point of 110°C (230°F) and a boiling point of 146°C (295°F) at 760 mm Hg. and asphalt additives. Note: “mlm” or “mlm” = –CH 2 CH 2 – 5 .Heavy Polyamine (HPA) is a complex mixture of linear. Aminoethylpiperazine (AEP) is unique among the ethyleneamines: it contains one primary. and coatings. AEP has a broad liquid range: boiling point of 222°C (432°F) at 760 mm Hg and a freezing point of -17°C (1. together with the hydroxyl group. Piperazine (PIP) is the simplest cyclic member of the ethyleneamines family. The major end-use applications for HPA include oil and fuel additives. and cyclic ethyleneamines. and asphalt additives. Aminoethylethanolamine (AEEA) is an organic base with unique properties that make it an invaluable intermediate. Since this narrow liquid range makes it difficult to handle. the structures of which can be deduced from the chemistry of manufacture and a knowledge of the structures present in TETA and TEPA. fabric softeners. chelates. pharmaceutical preparations. 14(3) 86. mm Hg 10.17 .32 8.72 — — (9) (9) Solubility in Water at 20°C.40 x 0.4(10) — (9) 0.95 x 10-4 (2) 0.65 x 0.986 1.21 104.22 10.01 6.52 0. at 25°C in Water 0.45(6) Vapor Pressure at 20°C.01 < 0. K1. 65% Piperazine.007 0. micromhos/cm Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine. Anhydrous Aminoethylpiperazine Aminoethylethanolamine Molecular Weight 60. % by wt 100 100 100(12) 100(12) 100(12) 100(10) 14 100 100 7.036(4) 0.994 1.08 < 0.39 .86 0.980 0.877(5) 0.01 < 0.10(7) < 0.17 146. with decomposition Solid at this condition At 42°C At 130°C Forms hydrate with time 6 .13 Vapor pressure of the solid Extrapolated. Anhydrous At 42°C/42°C At 130°C/20°C Pour point Ionization Constant.24 0.29 12.73 x 10-4 0.14 129.15 Freezing Point.28 0.35 .72 x 10-4 (2) 0.898 0.31 x (7) (8) (9) (10) (11) (12) 0.015 1.30(1) 275(2) 86.091 0.32(6) 41 110 .01 < 0.01 Electrical Conductivity at 25°C.030 Ethyleneamine Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine.13 19. Anhydrous Aminoethylpiperazine Aminoethylethanolamine (1) (2) (3) (4) (5) (6) Linear component only Typical molecular weight For Piperazine.43 x 10-4 0.63 10-4 10-4 7.Typical Physical Properties Apparent Specific Gravity at 20/20°C 0.63 x 10-4 10-4 (2) Dielectric Constant at 23°C 13.43 x 10-4 (3) 0.24 9.46(6) .40 0. 65% Piperazine.10 103.092 49.24(1) 189.952 0. ˚C 11 . 403 .14353 .4 88.80 7. heat of fusion 72.045 — 0.13910 .14487 .5(10) 0.73(11) 15.483 1.3 100.0 206.83 cal/g Estimated from vapor pressure using Clausius-Clapeyron equation Calculated from gross heat of combustion 7 .499 1. cal/g•°C 0.9 127.3 161.74 cal/g At 130°C.6°C.049 Absolute Viscosity at 20°C.Boiling Point.0 Refractive Index.058 0.056 0.78(13) 0.6 134.0 242.8 123. melting point 109.8 50 mm Hg 47.12395 Heat of Formation at 25°C. BTU/lb(15) 270 197 162 162 99 528 250 152 237 Heat of Combustion at 25°C.3 183 215 279(8) 54 — (9) 10 mm Hg 19.68 0.58 0.052 0.7 22.139(1) — — .043 0.63 0. cP 1.52 0.16 26.0 83.14643 .457 1.256 .569 .9 144 184 236 27 — (9) ∆ Boiling Point/∆p. °C 760 mm Hg 117.65 0.036 0. 750-770 mm. BTU/lb . melting point 36°C.505 1.486 (13) (14) (15) (16) At 42°C.14744 .14696 .513 — — (9) (9) Specific Heat at 20°C.1193 1.9261 . °C per mm Hg 0. BTU/lb(16) .9 277(8) 288(8) — 116 146.162(1) .13251 . heat of fusion 50.63(14) 0.304 .64 Heat of Vaporization at 760 mm Hg.501 1.1 460.1 221.61 0. nD20°C 1.037 0.4 140. Figure 1: Ethyleneamines. Vapor Pressure vs. ˚F 0 1000 800 600 500 400 300 PIP 200 20 40 80 120 160 200 240 320 400 480 560 Vapor Pressure. Temperature Temperature. ˚C 8 . mm Hg 100 80 60 50 40 30 20 10 8 6 5 4 3 2 EDA 65% PIP DETA AEP AEEA TETA TEPA UHP HPA X 1 -20 0 20 40 80 120 160 240 320 Temperature. 0 65% PIP PIP 0.0 AEEA TEPA UHP 100. ˚C 150 200 250 9 .0 EDA 1.0 HPA X 1000. Temperature 10000.0 Viscosity.1 -50 0 50 100 Temperature. cP TETA AEP DETA 10.Figure 2: Ethyleneamines. Viscosity vs. Figure 3: Ethyleneamines.95 EDA 0.00 AEP TETA DETA Specific Gravity. Temperature 1. ˚C 10 .10 1.75 -20 20 60 100 140 180 220 260 Temperature.90 TEPA UHP PIP 0. Specific Gravity vs.85 0. t˚C/20˚C 0.05 AEEA 65% PIP HPA X 1.80 0. 0˚C -55 0 10 20 30 40 50 60 70 80 90 100 Composition. Composition 15 5 Eutectic -0. Freezing Point vs.Figure 4: Ethylenediamine Aqueous Solutions. ˚C -15 -25 -35 -45 Eutectic -53.8˚C -5 Temperature. Weight % Ethylenediamine 11 Composition of Monohydrate Composition of Dihydrate . ˚C 112 108 104 100 0 10 20 30 40 50 60 70 80 90 100 Composition. Vapor-Liquid Equilibria at 760 mm Hg 120 Vapor Phase 116 Liquid Phase Temperature. Mole % Ethylenediamine 12 .Figure 5: Ethylenediamine Aqueous Solutions. cal/gm of Solution 30 25 20 15 10 5 0 0 10 20 30 40 50 60 70 80 90 100 Composition. Heat of Solution at 22˚C 50 45 40 35 -∆ Hm. Weight % Water 13 .Figure 6: Ethylenediamine Aqueous Solutions. Figure 7: Ethylenediamine Aqueous Solutions.92 0.88 0 10 20 30 40 50 60 70 80 90 100 Composition.98 0.00 0.96 Specific Gravity at 20/20˚C 0. Weight % Ethylenediamine 14 . Temperature 1.90 0.94 0. Specific Gravity vs. Weight % Piperazine Studies show evidence of a metastable freezing point in the region of 20 wt.% piperazine Composition of Hexahydrate 15 . ˚C 60 40 Eutectic 33.Figure 8: Piperazine Aqueous Solutions. Composition 120 100 80 Temperature.2˚C 20 0 Eutectic -1˚C -20 0 10 20 30 40 50 60 70 80 90 100 Composition. Freezing Point vs. Figure 9: Piperazine Aqueous Solutions. Vapor-Liquid Equilibria at 760 mm Hg 150 145 140 135 Vapor Phase 130 Temperature. ˚C 125 Liquid Phase 120 115 110 105 100 95 0 10 20 30 40 50 60 70 80 90 100 Composition. Mole % Piperazine 16 . 17 . depending upon structure. Other ethyleneamines react similarly.Reactions of Ethyleneamines† † Illustrated by reactions of ethylenediamine (EDA). RX 5. 18 .Inorganic Acids Ethyleneamines react vigorously with commonly available inorganic acids.Reaction Notes RX 1. . RX 2. Various diamides of EDA are prepared from the appropriate methyl ester or acid at moderate temperatures (2. or acyl halides to form amidoamines and polyamides. Product distribution is controlled by the ethyleneamine-to-aziridine mole ratio. RX 4. . . Monoamides can be cyclized to form imidazolines.Ureas Ethyleneamines react with urea to form substituted ureas and ammonia (11). Either gas. .Epoxides Ethyleneamines react readily with epoxides. acid anhydrides.Alcohols and Alkylene Glycols Simple aliphatic alcohols can be used to alkylate ethyleneamines with hydrogen in the presence of a reductive amination catalyst (17). water soluble salts. to form mixtures of hydroxyalkyl derivatives (12-14).Organic Acids Ethyleneamines react with acids. This can be done without isolating the monoamide (4-8).or liquid-phase reactions of ethyleneamines with glycols in the presence of several different metal oxide catalysts lead to predominantly cyclic ethyleneamine products (18). Product distribution is controlled by the amine-to-epoxide mole ratio.Nitriles Hydrogen cyanide (HCN) and aliphatic nitriles (RCN) can be used to form imidazolines (9-10). RX 7. an explosive compound. forming crystalline.Aziridines Aziridines react with ethyleneamines in an analogous fashion to epoxides (15-16). . esters. is made by reacting one mole of EDA with two moles of nitric acid and splitting two moles of water from the salt at elevated temperatures (1) . RX 3. RX 6. .3). Ethylenedinitramine. . such as nitrogen oxides. However. nitrites. . activated by electron withdrawing groups. is prepared by reacting CS2 in aqueous EDA (22). depending on the reactant ratio (20). and structure of the ethyleneamine. Aliphatic dihalides.or disubstituted derivatives. Ethylene thiourea. amine hydrates may form. crosslinked. they are sufficiently reactive that upon exposure to adventitious water.Environmental Reagents: CO2. trace levels of byproducts can form and increased color usually results. RX 9. in concentrated aqueous solutions. NOx. RX 10. carbon dioxide. or nitrous acid. . which can be reacted with zinc (or manganese) to give the appropriate dithiocarbamate salt. Mixing methylene chloride and EDA reportedly causes a runaway reaction (19). . The products depend on stoichiometry.RX 8. the reaction being mildly exothermic. to form nitrosamine derivatives (24). RX 11. a suspect human carcinogen.and disubstituted imidazolidines via cyclization of the intermediate Schiff base (21). 19 . metal complexation or choice of solvent. However. nitrogen oxides. N-Alkyl-piperazines and piperazine can react with nitrosating agents. Ethyleneamines are soluble in water.Sulfur Compounds EDA reacts readily with two moles of carbon disulfide (CS2) in aqueous sodium hydroxide to form bis sodium dithiocarbamate. Reactions of aldehydes with such ethyleneamines as EDA or DETA give mono. reaction conditions. react with ethyleneamines to form various polymeric. Product distribution is controlled by reactant ratio. O2 Under normal conditions ethyleneamines are considered to be thermally stable molecules. react with ethyleneamines to form mono. .Aldehydes Ethyleneamines react exothermically with aliphatic aldehydes. The hydrates of linear TETA and PIP melt around 50°C (25-26). water-soluble cationic products or higher ethyleneamine products. Carbon dioxide reacts readily with EDA in methanol to form crystalline N-(2-aminoethyl)carbamate (23). and oxygen. H2O. such as ethylene dichloride.Halides Alkyl halides and aryl halides. basicity.Ethyleneamines Applications Ethyleneamines are utilized in a wide variety of applications because of their unique combination of reactivity. The following table lists the major end-use applications for these versatile materials. They are predominantly used as intermediates in the production of functional products. . and surface activity. Major End-Uses for Ethyleneamines Application Lube Oil Additives Fuel Additives Polyamide Resins Asphalt Chemicals Corrosion Inhibitors Wet-Strength Paper Resins Epoxy Curing Agents Bleach Activators Chelating Agents Ore Flotation Agents Surfactants Fabric Softeners Fungicides Anthelmintics Spandex Fibers Urethanes Military Decontamination Agents Plastic Lubricants Ion Exchange Resins Coatings NOTE: The largest volume applications are indicated by ++ EDA DETA TETA TEPA Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine HPA PIP AEP AEEA Heavy Polyamine Piperazine Aminoethylpiperazine Aminoethylethanolamine EDA DETA + TETA + + ++ + + ++ TEPA ++ + ++ + + + ++ HPA ++ PIP AEP AEEA ++ ++ + + ++ ++ ++ + + ++ ++ + + ++ + + ++ ++ ++ + + ++ ++ ++ + + ++ + + + ++ ++ + + + ++ 21 . The lubricant additives function mainly to reduce the formation of however. The ethyleneamine derivatives most commonly employed for these tasks are the mono.and bis-polyisobutenyl-succinimides. Post-treatments of the succinimides are commonly utilized for performance improvement in engine oils (4658). normally prepared by the condensation reaction of polyisobutenyl-succinic anhydrides (PIBSAs) (1. 22 . by solubilizing oil-insoluble liquids. a different linkage is employed in another important class of ashless dispersants – the Mannich bases (60-70). Ethyleneamines are also used in dispersant- sludge and varnish deposits within internal combustion engines by inhibiting the aggregation of particles. The alkyl and ethyleneamine moieties are similar to those used in the succinimide products. 2) with ethyleneamines (3-44). and in certain dispersantdetergents for fuels. They are prepared on a commercial scale by reaction of an alkylphenol with formaldehyde and an ethyleneamine (71-76). Besides the more common means of linking long-chain hydrophobic moieties to ethyleneamines via the succinimide linkage. The higher molecular weight ethyleneamines are most popular for these derivatives.Lubricant and Fuel Additives The largest application area for ethyleneamines is in ashless dispersants for engine oils and other lubricants. and by neutralizing acidic species formed in the combustion process. varnish inhibitors for lubricating oils for twostroke engines (59). all the ethyleneamines have been employed for various products (45). tri. for example. Numerous similar products made generally by alkylating or acylating EDA or DETA (87-95) are also used as fuel detergent and deposit control additives. Anti-rust additives for lubricating oils have also been prepared by reacting ethyleneamines with fatty acids followed by reaction with polyalkylenesuccinic anhydrides (77. and foil webs (8). overprint varnishes. 4). pressure-sensitive. cellophane. 78).Lubricant and Fuel Additives (cont’d) Additives for lubricating oils providing a combination of viscosity index improvement (VII) and dispersancy have also been reported. and. Polyamide Resins The main polyamide resin type. a number of antiwear/antiscuff additives for lube oils and greases also use ethyleneamines. and heat-seal adhesives for leather. to plasticize nitrocellulose lacquers (6). abrasionresistant. These additives are prepared from ethyleneamines by reaction with various viscosity index improvement polymers that have been modified. plastic. EDA is a principal amine reactant (1). Being soluble in alcohol-based solvents and exhibiting outstanding adhesion to polyolefins. and metal. Oil additives providing detergent properties have also been prepared from ethyleneamines (79. EDA. they are particularly suited to these applications. They are also used in preparing fatty acid/amine soaps and poly(urea) thickeners for lubricating greases. polyester. however.and polybasic fatty acids.and tetramines are sometimes used at low levels to achieve specific performance (2). Polyamide resins find wide use as binders in printing inks for flexogravure application on certain paper. is that prepared generally by the condensation reaction of diamines with di. PIP and certain PIP derivatives are used with EDA in certain cases (3. They are also used to modify alkyd resins in certain thixotropic coating systems (5). 23 . and AEEA have found significant commercial application as dispersant detergent additives for gasoline when made by this route. and as corrosion inhibitors in alkyd paints (7). Dispersant-detergent additives useful in gasoline are prepared by the direct alkylation of ethyleneamines with chlorinated polybutenes (81-86). 80). and paper. via chlorination. Thermoplastic polyamides are similarly used in formulating glossy. DETA. paper. Cetane improvement in diesel fuels has been reported for a mixture containing EDA (96). These polyamides are used in hot-melt. to provide a reaction site. in addition to the liquid resins used as epoxy hardeners. film. i. they are represented by the products made from DETA and fatty acids (1-7). for example. and TETA. 17).Asphalt Additives and Emulsifiers Mono. Specific ethyleneamine derivatives can also be used for water clarification (16. 12. The oil-water emulsions generated at times by petroleum wells can often be broken with certain ethyleneamine derivatives (8-10) (EDA. mono. 13). to separate carbon disulfide from a pyrolysis fraction (21). and their mixtures are used in antistrip formulations and asphalt-in-water emulsions. 11. These are generally used as their HCl or acetic acid salts. and pH and increase resistance to hydrolysis (15). They are typically prepared from the higher molecular weight ethyleneamines and fatty acids (1-7). 24 . In some secondary recovery operations. TEPA and other ethyleneamines combined with thickeners help stabilize viscosity. Ethyleneamines are also employed in petroleum refining operations. imidazolines. as part of a composition used as an antioxidant to control fouling (19). Petroleum Production and Refining A number of ethyleneamine derivatives are also employed in petroleum production and refining operations as corrosion inhibitors. and in the processing of certain catalysts (22-25). to separate alkenes from thermally-cracked petroleum products (20). Similar ethyleneamine derivatives are used to make stable asphalt-in-water emulsions (8-16). patching.and bis-amidoamines. Typically. mobility. These films displace the corrosive production fluids and attract a film of petroleum which further isolates the steel from the fluid.e. as part of a system used to extract thiols from petroleum distillates (18). and polyamides.and bis-amidoamines. DETA. neutralizers. They are usually applied to the petroleum well by any of several methods designed to create a film of inhibitor on the surfaces of the steel structures in the petroleum well. Antistrip additives promote adhesion between the mineral aggregate and the asphalt in mixtures for road paving. Corrosion inhibitor formulations for downhole petroleum production applications use a significant volume of ethyleneamines. and surfacing. They generally utilize the condensation reaction products of higher ethyleneamines and fatty or dimer acids. demulsifiers. and functional additives. ethyleneamines can be used to decrease the migration of injected chemicals into the formation by adsorption and precipitation (14). imidazolines.. and paper coatings (21). incorporate ethyleneamines such as DETA. ethylenebis(stearamide). packaging paper products. Ethyleneamines are also used in the preparation of certain flocculating agents (13). made by the reaction of ethyleneamines with epichlorohydrin (9). toweling. 8). Cationic formaldehyde. The bis-amide made by reacting EDA with stearic acid. is used as a defoamer in paper mill operations. Polyamine wetstrength resins. 2). The most popular paper wet strength resins are the modified polyamides typically made with DETA. adipic acid and epichlorohydrin (37). and acidic conditions required by modified formaldehyde resins. to make nonacidic papers.Resins and Additives for Pulp and Paper Ethyleneamine-based chemicals are used widely in the paper industry to impart specific functional characteristics to the finished paper. waterproofing and sizing compounds (14-16). and polyamine resins. antistatic agents (17-20). are also used. TETA. These resins can be used under less corrosive neutral or alkaline conditions. and/or TEPA in the resin backbone to provide substantivity to the cellulose fibers in paper. Improved rates of EDA recovery (25) have also been developed for EDA-sulfide pulping processes (26. represent a major end use for ethyleneamines. Even though they tend to be less expensive. both urea. The cationic formaldehyde resins. 25 . these types of paper wetstrength resins have been decreasing in popularity due to the adverse health effects associated with formaldehyde. 6. polyamide. 11) and polyamines (12). added to the beater stock to improve the wet strength of tissue. The sulfur-free delignification of wood chips with EDA-soda liquors has received some interest in the past few years (22-24). 27).and melamine-formaldehyde types (1. Numerous modifications of this resin type have been reported (4. rather than the Certain pigment retention and drainage additives made with ethyleneamines include various polyamides (10. etc. respectively. laminates. The presence of different polyamino functionalities in the higher ethyleneamines allows partial reaction with various modifiers while retaining sufficient primary and secondary amino functionality for reaction with the epoxy resin portion of the system. grouts.Epoxy Curing Agents All the commercial ethyleneamines are used either neat or as derivatives for curing epoxy resin-based coatings. Bleach Activators Tetraacetylethylenediamine (TAED) has been widely adopted for use in home laundry products as an activator for peroxygen bleaches. castings. which is then reacted with two moles of acetic anhydride to form the tetra-amide. It is prepared by first reacting EDA with two moles of acetic acid to form the bis-amide. formaldehyde. are widely used for longer pot life and better flexibility. Mannich bases prepared from a phenol. (1). Although the ethyleneamines themselves are often used as the curing agent or part of a curing agent package. to give derivatives providing longer pot life and better wetting of glass (14). patibility with liquid epoxy resins (9-13). a common modification is the addition of an alkylene oxide. and solvent resistance (8). Other modifications of the ethyleneamines include partial reaction with epoxy resin to form a prepolymer. handling. 26 . adhesives. such as ethylene oxide. For example. and tertiary amino functionality to catalyze that reaction. they are commonly modified in various ways to achieve performance. 7). cyanoethylation. and a variety of other ethyleneamine modifications (15-18). which provides improved com- ments. ketimines. usually by reaction with acrylonitrile. made by the reaction of EDA with acetone. adhesion. and a polyamine. and safety improveAmidoamines and reactive polyamides prepared by condensation of TETA or higher polyamines with fatty acids (3-5) and dimer acids (6. to DETA (2) as shown above. Most of the amidoamines and reactive polyamides contain significant levels of imidazoline structure. They may be made also by reaction of the ethyleneamine with sodium chloroacetate. chromium. concentrated. and as ingredients in systems for etching and for stripping nickel and nickel alloy coatings. 2). Chelating resins. These same kinds of derivatives can be used for beneficiation of niobium and tantalum ores (3). separated.Chelates and Chelating Agents Polycarboxylic acids and their salts derived from ethyleneamines are used in a variety of applications where specific metal ions interfere with processing. where their metal complexing properties are required. called chelates. 2). This property makes the ethyleneamines useful in specialized applications. The most important commercial family of chelating agents is ethylenediamine tetraacetic acid (EDTA) and its various sodium salts. and formaldehyde in the presence of sodium hydroxide (1. with most di. 5). and the ethyleneamines themselves aid extraction of copper. and nickel from their sulfide and oxide ores (4). AEEA and DETA are also used to make similar polyacetic acid or acetate products. has found application recently in chlorine-free paper pulp bleaching to prevent iron from decreasing efficiency of the hydrogen peroxide (6). The intermediate polynitrile may either be hydrolyzed in situ (3). made from EDA. Metal Ore Processing Certain processes for enrichment of iron and phosphate ores use amidoamines and imidazolines made from ethyleneamines and fatty acids. Diethylenetriaminepentaacetate (DETPA). These derivatives selectively adhere to silica particles and permit their removal by flotation procedures (1. and in lead ore processing and recovery operations (5-8). 8). made from DETA. It should be pointed out that unmodified ethyleneamines also form stable complexes with certain metal ions. polymers (7. sodium or hydrogen cyanide. They operate by forming stoichiometric complexes.or polyvalent metals. These compounds are produced on an industrial scale primarily through the reaction of the ethyleneamine. 27 . such as zinc and copper. and fibers (9) have also been developed. or transported. such as electroplating and electroless metal coating with specific metals and many alloys. or separated and hydrolyzed separately (4. or need to be buffered. TEPA. 28 . The imidazolines are generally converted into amphoteric surfactants for this application by reaction with one or two moles of sodium chloroacetate (9-11). ethoxylated with an average of 17 moles of ethylene oxide. amidoamines derived by the non-cyclicizing reaction between amine and acid. The PIP salts have long been the agents of choice for use against roundworms and pinworms (1). The products of a reaction between DETA. and the imidazoline formed by the reaction under vacuum at virtue of their mildness and good foaming characteristics.Surfactants and Emulsifiers To prepare surfactants derived from ethyleneamines. improves the soil antiredeposition and clay soil removal properties of certain liquid laundry detergents (13). 2). or TEPA and fatty acids also function as water-in-oil or oil-in-water emulsifiers (12). Anthelmintics (Dewormers) Piperazine is the active ingredient in certain veterinary anthelmintic preparations – primarily for combating intestinal worms in poultry and swine. A variety of 2-alkylimidazolines and their salts prepared mainly from EDA or AEEA are reported to have good foaming properties (3-8). elevated temperature to remove two moles of water are all used. AEEA-based imidazolines are also important intermediates for surfactants used in shampoos by TETA. amine salts or soaps obtained by simply mixing the amine with a fatty acid (1. made from DETA and fatty acids. “softer” or more pleasing to the touch. which gives amphoteric softeners (9). to yield compounds that can be formulated into softener products for home laundry use (4-6). As a result. and impart fluffiness. Softeners also act as antistatic and antisoiling agents. that are either cyclized to the corresponding imidazoline by further dehydration.Fabric Softeners Softeners are commonly added to textile materials to make them less harsh. or reacted with ethylene oxide (3) to convert the central secondary amine group to a tertiary amine. 29 . These intermediates are then quaternized. or sodium chloroacetate. Softeners are added to the home washing machine during a rinse cycle or as part of a detergent/softener combination product. 2). as well as their quaternized derivatives. The amino esters. Softening agents based on DETA and TEPA are also used in industrial textile processing operations (1. are more subject to hydrolysis than the amidoamine and imidazoline compounds. Amino esters are made from acids and an amino alcohol. generally with dimethyl sulfate. decreased storage stability and performance. they have gained some popularity where environmental biodegradation concerns outweigh their The most common ethyleneamine-based fabric softeners are bis-amidoamines. or to the clothes dryer. Softeners based on bis-imidazoline compounds are also prepared by condensing TETA or TEPA with fatty acids (7) or triglycerides (8). such as AEEA. followed by quaternization with dimethyl sulfate. They are used on many fruit. It is used as the acetate salt for control of apple scab and cherry leaf spot.Fungicides The ethylenebisdithiocarbamates (EBDCs) are a class of broad-spectrum. contact fungicides first used in the early 1940’s. rust. 30 . and grain crops for prevention of mildew. preventative. The ammonium (amobam) and mixed zinc and manganese (mancozeb) salts are also known. and blight. scab. vegetable. primary commercial products. was found to be unstable. potato. A 2:1 EDA-copper sulfate complex has been suggested for control of aquatic fungi (10). The EBDCs are prepared by reacting EDA with carbon disulfide in the presence of an aqueous base. nabam. it is stabilized by conversion to certain other divalent metal salts. The most important of the imidazoline type (8) is 2-heptadecyl-2-imidS CH2–NH–C–S–Na H2C–CH2–CH2–NH2 + CS2 + 2NaOH CH2–NH–C–S–Na S + 2 H2O This sodium derivative. prepared from EDA and stearic acid. Zineb and maneb are normally formed by the addition of zinc or manganese salts to nabam solutions. The zinc (zineb) and manganese salts (maneb) are especially effective (1-7) and are today the azoline (9). However. Other materials based on EDA have also been suggested as fungicides. industrial corrosion inhibition. shrinkproofing wool (5). viscosity regulator. Ethyleneamines find application in vulcanization processes for certain rubbers (1-11). and surface gloss enhancer. including the treatment of a wide variety of natural and synthetic fibers for modification of certain properties (1. stone and concrete coatings. as precursors for certain compounds providing durable press (3). ion exchange resins. fire retardants. polymer concrete and concrete additives. The bisamidoamine condensate made from TETA or TEPA and stearic acid is used as a defoamer in certain textile treatment baths. static prevention (6).Textiles Ethyleneamines are used in the textile-related industries for a variety of applications. functional fluids. and polyol starters. TETA has been recommended as a curing agent for furfural resin binders in foundry molds and molded graphite. to reduce static in polystyrene foam. DETA. catalysts (TEDA [triethylenediamine] is a significant example). Dye assist compounds for synthetic fibers have been derived from EDA. pharmaceuticals. EDA is used in preparing silane and silanol compounds that improve the adhesion between inorganic surfaces and polymer films. 2). in phenolic resin curing. petroleum production. Urethane systems and processes employ certain ethyleneamines and their derivatives as curing agents. preservative. explosives. ceramics. and they are used in styrene-butadiene latex processes to coagulate the low levels of finely-dispersed particles in the reaction medium (12-15). light stabilization of spandex fibers (4). and mothproofing (7). Polymers and Elastomers EDA is a key component of the polymer in spandex fiber. to inhibit isoprene polymerization. plaster systems. 31 . gas and water treating. and as a parting material. EDA reacted with stearic acid makes ethylene-bis(stearamide) (EBS) that is used as an external lubricant for ABS resin and PVC. and for etching polyimide films. DETA is a component of Nylon 6 (11). Acrylate and other monomer vapors can be efficiently removed from vent streams with scrubber solvents containing TETA. EDA specifically can be used as a stabilizer for certain urea resins. and TEPA (8-10). TETA. Other Applications Ethyleneamines find application in numerous other specific industries. They include coal-oil emulsification and coal extraction. and membranes. 18 8.92 8.24 8.027 (5) At 80 °C at 15.995 1. additional information on shipping data.21 8. Please contact Dow at the numbers on the back of this booklet. kg Ethyleneamine Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine. We will provide a technical contact to discuss specific questions you might have.984 1.30 8.51 7.896 0.95 8.48 7.56°C 0.44 8.980 0.27 8.949 0. Anhydrous Aminoethylpiperazine Aminoethylethanolamine (1) At 65°C (2) Solid at this condition (3) At 20°C to 30°C (4) At 45°C to 65°C at 20°C 0.953 0.15 8.56°C 7.977 0. labeling and container requirements may be obtained by contacting Dow at the numbers on the back of this booklet.60 Metric Units Average Weight per liter. 65% Piperazine.031 Product Specifications Product specifications and methods are available upon request. 32 .900 0. Anhydrous Aminoethylpiperazine Aminoethylethanolamine (1) At 65°C (2) Solid at this condition (3) At 20°C to 30°C (4) At 45°C to 65°C at 20°C 7.Shipping Data Since governmental regulations are subject to change.005 (1) — (2) 0.39 (1) — (2) 8.57 (5) At 80 °C at 15.47 — (2) — (2) 8.011 1. Average Weight per gallon. lb Ethyleneamine Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine.991 1.987 1. 65% Piperazine.015 — (2) — (2) 0. 00106 0. ASTM Method D 93 C = Cleveland Open Cup.000792 0.00083 0.00085 0.00794 0.00085 0. °F Closed Cup 110 T 208 P 300 P 340 P 345 P None T 130 P 215 P 260 P Open Cup 103 TO 225 C 310 C 360 C 445 C 205 C 215 C 250 C 310 C (6) T = Tag Closed Cup.00077 at 55°C 0.00092 0.00077 Flash Point (6).00642 (3) 0.000747 (3) 0. per °C 0.00076 0.00095 (5) — (2) 0.00640 (3) Coefficient of Expansion.00081 0.00077 Flash Point (6). ASTM Method D 92 TO = Tag Open Cup.00077 at 55°C 0. ASTM Method D 1310 ∆kg/liter/∆t 10°C to 30°C. per °C at 20°C 0.00081 0.000951 0.00092 0.00089 0.∆lb/gal/∆t 10°C to 30°C.00623 (3) 0.000769 (3) 0.000943 (4) — (2) 0. per °C at 20°C 0.00076 — (2) — (2) 0.00086 0.00661 0.00076 — (2) — (2) 0.000767 (3) Coefficient of Expansion.000815 (3) 0.000842 0. per °C 0. and nominal 55gallon drums.00076 0.00106 0. rail car. 33 .00089 0.00080 0.00703 0. ASTM Method D 1310 Product Availability Products are available in bulk ocean tanker. ASTM Method D 93 C = Cleveland Open Cup.00095 (5) — (2) 0. °C Closed Cup 43 T 98 P 149 P 171 P 174 P None T 54 P 102 P 127 P Open Cup 39 TO 107 C 154 C 182 C 229 C 96 C 102 C 121 C 154 C (6) T = Tag Closed Cup.00680 (3) 0.00787 (4) — (2) 0.00110 0. ASTM Method D 56 P = Pensky-Martens Closed Cup.00081 0.00110 0.00080 0.00086 0. ASTM Method D 56 P = Pensky-Martens Closed Cup.00083 0. tank truck.00081 0. ASTM Method D 92 TO = Tag Open Cup. heavier ethyleneamines without noticeable impact on product quality. A 300 series stainless steel is often specified for pumps. Galvanized steel. nitrogen oxides. Carbon steel with baked phenolic lining is acceptable for storage of many pure ethyleneamines. dedicated processing equipment is recommended. TFE is an alternative to elastomers since it is resistant to ethyleneamines. To avoid this situation. heating coils. porous insulation may introduce the hazard of spontaneous combustion if the insulation is saturated with ethyleneamines from a leak or external spill. minimizing insulated flanges and fittings. except EDA. Carbon steel is not recommended for EDA. this may lead to spontaneous combustion. then 300 series stainless steels are recommended for the storage tanks. If this cannot be tolerated. Storage under a dry. e. and small agitated tanks. and either smoldering or a flame may be observed. transfer lines. carbon dioxide. it may not always prove suitable as a replacement material.. spill absorbents and metal wire mesh (such as that used in vapor mist eliminators). for nonaqueous. even at ambient temperature. maintenance of weather barriers. valves. Risk of insulation fires can be reduced by insisting on good housekeeping.Storage and Handling Ethyleneamines react with many other chemicals.001 in/yr) at typical storage temperatures. watersaturated containers. Modest storage temperature (less than 60°C) and nitrogen blankets will allow the use of carbon steel. Water. Consequently. since TFE is not a true elastomer. Closed cellular glass insulation is normally resistant to insulation fires because it is difficult for the ethyleneamines to saturate these materials and also difficult for air to contact the product. In some cases. self-heating of ethyleneamines may occur by slow oxidation in other absorbent or high-surface-area media. Nonmetallic equipment is not normally used for ethyleneamine service. This may lead to low levels of byproducts and increase the color of the product.g. sometimes rapidly and usually exothermically. like many other combustible liquids. Proper selection of materials of construction for ethyleneamine service is essential to ensure the integrity of the handling system and to maintain product quality. Carbon steel transfer lines or agitated equipment will suffer enhanced corrosion because of erosion of the passive film by the product velocity. copper and copper-bearing alloys are unacceptable for all ethyleneamine service. Ethyleneamines can permeate polyethylene and polypropylene. or AEEA storage tanks. or be thoroughly wetted with water and then disposed of in closed. No single elastomer is acceptable for the entire product line. inert atmosphere (such as low CO2-containing nitrogen) will minimize this sort of degradation. consistent with local and federal regulations. Most commonly used industrial thermal insulating materials are acceptable for ethyleneamine service. However. but the products will pick up iron and discolor badly. any of these media contaminated with ethyleneamines should be washed with water to remove the amines. and oxygen from the atmosphere may be absorbed by the amines. Corrosion is not extreme (<0. in dedicated service. Recommended gaskets for ethyleneamine service are made of GRAFOIL™ flexible graphite or polytetrafluoroethylene (TFE). 34 . and training personnel. DETA. dumped filter cake. However. certain grades of these materials may be acceptable in some storage applications. Also. However. Water cleanup of ethyleneamine equipment can result in hydrate problems. EDA has the lowest flash point (Tag Closed Cup): 43°C (110°F). Vent fouling can be reduced by using nitrogen blankets on storage tanks to exclude atmospheric CO2. Hydrates can plug processing equipment. heavier ethyleneamines may be stored at elevated temperatures (40-60°C) to ease inplant handling by lowering the viscosity. mineral acids contamination). which causes the carbamates to decompose. vent units and relief devices may be steam-traced to maintain 160°C. Additionally. contact Dow at the numbers on the back of this booklet. For additional information. 35 . Additionally. In addition. Hydrate problems are usually avoided by insulating and heat tracing equipment to maintain a temperature of at least 50°C. may be found in the Material Safety Data Sheets. Health Effects Information on health effects and their management. ethyleneamines exhibit good temperature stability. which can be a nuisance in handling. in certain concentrations. Tank vents and safety devices are also susceptible to fouling by solid amine carbamates formed by the reaction of the amines with carbon dioxide. This information is of a general nature.The amines do not present any unusual flammability problem at ordinary temperatures. contact Dow at the numbers on the back of this booklet and request our Ethyleneamines Storage and Handling Brochure and/or a technical contact who will discuss specific questions about acceptable materials of construction and storage practices. Testing for thermal stability is suggested whenever ethyleneamines are mixed with other materials. At elevated temperatures some product breakdown may be observed in the form of ammonia and the formation of lower and higher molecular weight species. vent lines and safety devices. Warm water cleanup can reduce the extent of the problem. All amine vents should be routed to a safe location and “smoking vents” routed to water scrubbers to capture the vapors. For the latest Material Safety Data Sheets on ethyleneamines. Vent units require periodic inspection to verify that fouling is not occurring and to ensure that seals are functioning properly to exclude air from the tank. Also. Ethyleneamines are typically maintained above their freezing points which may require storage above ambient temperatures (particularly EDA and PIP). Storage at elevated temperatures can cause vapors “breathing” from the tank to contain significant concentrations of product. As commercially pure materials. solid amine hydrates may form. although the amines are water-soluble. contaminants can lower the onset of rapid exothermic thermal decomposition (for example. which are updated as new information becomes available. This degradation increases in rate as the temperature and/or time increases. even in areas where routine processing is nonaqueous. as well as recommended safety procedures. 63 Calc.Ecological Fate and Effects Dow has conducted a series of laboratory studies on the biodegradation and ecological effects of these amines.86 1. Calculated value based on oxygen required to oxidize the chemical to carbon dioxide and water. (2) Measured in dilution bottle biochemical oxygen demand test published in Standard Methods. Ecological Fate and Effects of Ethyleneamines Theoretical Oxygen Demand. and AEP. Aquatic toxicity measurements showed only moderate toxicity for most of the tested amines. The data presented in the following table show that the amines biodegrade slowly. 65% Aminoethylpiperazine Aminoethylethanolamine Carbonaceous Meas.86 1.33 1. (ThOD) mg/mg(1) Product Evaluated Ethylenediamine Diethylenetriamine Triethylenetetramine Tetraethylenepentamine UHP Heavy Polyamine X Piperazine. and 20. Biodegradation was measured by the riversimulating 20-day biochemical oxygen demand (BOD) test using nonacclimated microorganisms. 17th ed. 2. ASTM.75 — — 1. (3) The measured biooxidation as a percent of the total carbonaceous and nitrogenous oxygen demand (sum of calculated carbonaceous and nitrogenous ThOD values) is presented for Days 5.13 1.88 1. Several amines.68 1. These studies were conducted by procedures which follow the EPA. and Standard Methods techniques.84 1. Natural acclimation in a wastewater treatment plant or in the general environment would be expected to increase the rate and extent of biodegradation for the related compounds.94 1. (COD) 1.69 — 1. 1. (1989).49 1.54 Nitrogenous Calc. with the exception of EDA/DETA studies which used acclimated seed. Bacterial inhibition tests indicate that none of these amines tested should be inhibitory to conventional wastewater treatment processes at expected discharge levels of less than 500 mg/L.55 1. except for EDA and AEEA. Nonacclimated domestic sewage microorganisms used as seed.64 1.48 1. Public Health Assoc. EDA. showed more toxicity to Daphnia magna with LC50 values ranging from 5 to 40 mg/L. The biooxidation values are calculated as percentage ratio of BOD and ThOD (BOD/ThOD x 100). 10. The impact of acclimation on the rate and extent of biodegradation is shown by the EDA and DETA acclimated seed data.. DETA.28 1. TETA.50 1.86 1.93 1. while the nitrogen converts to and remains as ammonia.23 (1) Measured by Chemical Oxygen Demand (COD) procedure published in Standard Methods for the Examination of Water and Wastewater. 36 . The nitrogenous oxygen demand is calculated based on nitrogen being oxidized to nitrate by nitrifying bacteria. which rapidly biodegraded. contractors. you should obtain available product safety information and take necessary steps to ensure safety of use. you should review our latest Material Safety Data Sheets and ensure that the use you intend can be accomplished safely. No chemical should be used as or in a food. No nitrification was measured in the acclimated systems. medical device. Before handling any other products mentioned in the text. The customer should furnish the information in these publications to its employees. The 95% confidence limits (95% CL) are shown in parentheses. understand. and comply with the information contained in this publication and the current Material Safety Data Sheet(s). mg/L 48-hour 96-hour Daphnia magna Fathead Minnow 5 (4-6) 17 (15-19) 40 (35-50) — — 90 (80-110) 36 (25-50) 110 (90-130) 210 (190-230) 260 (220-310) 330 (280-400) 310 — 720 (640-800) 560 (500-620) 515 (470-560) (4) Determined by turbidity/growth procedures where the median inhibition concentration (IC50) is measured after 16 hours of incubation with sewage microorganisms. (5) Fathead minnows and Daphnia magna bioassays were conducted using procedures published by EPA and ASTM. For Material Safety Data Sheets and other product safety information. or cosmetic. drug. % biooxidation Total Carbonaceous(2) Days 5/10/20 68/100/100 A36(6)/A45(6)/A70(6) <5/<5/<5 A23(6)/A46(6)/A70(6) 3/4/9 4/7/12 <5/<5/<5 <10/<10/<10 2/4/7 2/64/90 —/—/— —/—/— —/—/— —/—/— —/—/— —/—/— 1/37/53 >5000 680 — — 4600 1400 >5000 25/37/78 1000 Nitrogenous(3) Days 5/10/20 Bacterial (4) Inhibition IC50. Dow requests that the customer read. Biochemical Oxygen Demand(2).Product Safety When considering the use of any Dow products in a particular application. medical device. it is the user’s responsibility to determine that this information is appropriate and suitable under current. or in a product or process in which it may contact a food. Since government regulations and use conditions are subject to change. (6) Biooxidation values for EDA and DETA are taken from tests with acclimated microorganisms. mg/L Aquatic Toxicity (5) LC50. contact Dow at the numbers on the back of this booklet. or cosmetic until the user has determined the suitability and legality of the use. and customers. or any other users of the product(s). 37 . drug. applicable laws and regulations. and request that t hey do the same. Polyamide-epichlorohydrin resins prepared by reacting adipic acid or other acids with diethylenetriamine to form a basic polyamide and further reaction of the polyamide with other materials to form water-soluble thermosetting resins for use in the manufacture of paper and paperboard. Component in an antimicrobial formulation used in cane sugar mills.180 176.300 175.1010 177.105 175. crusher.320 175. Polyamides formed by reaction with dimerized vegetable oil acids for use as components of food-packaging adhesives. applied to the sugar mill grinding. Crosslinker with epichlorohydrin to make ion-exchange resins used in the processing of food.1200 177.0 ppm based on the weight of raw cane or beets processed. Urea-formaldehyde resins chemically modified with polyamines made by reacting ethylenediamine with dichloroethane or dichloropropane for use as a component of the coated or uncoated food-contact surface of paper and paperboard in contact with dry food.170 176.25 173. Catalyst for epoxy resins and component of polyamides for use in making closures with sealing gaskets.1210 177.180 176.180 176. Component in an antimicrobial formulation used in cane sugar and beet sugar mills. and/or diffusor systems at a maximum level of 2.3120 38 . 175. sulfanilic acid. Component of adhesives used in articles intended for packaging. aqueous. and dry food.210 176. it is the responsibility of the user of an ethyleneamine as a Direct or Indirect Food Additive to read and understand any applicable FDA regulations in Title 21 of the Code of FDA Regulation Ethylenediamine 21 CFR Permitted Uses 173. and other listed amines.300 177.380 175.1200 177. Polyamines made by reacting ethylenediamine with dichloroethane or dichloropropane. at a level not to exceed 0.170 176.2600 178.300 Preparation of ion-exchange membranes used in the processing of grapefruit juice.300 175. Additive in the production of animal glue. and dry food.0 ppm based on the weight of raw cane processed.170 176. Catalyst activator in semirigid and rigid acrylic and modified acrylic plastics.105 175.180 176. However. Modifier for urea-formaldehyde and melamine-formaldehyde resins used as the basic polymer in resinous and polymeric coatings on a metal substrate. Modifier for amino resins used as a component of the coated and uncoated food-contact surface of paper and paperboard in contact with fatty. Polyamines made by reacting ethylenediamine with dichloroethane or dichloropropane for modifying urea-formaldehyde resins used as the basic polymer and as a resin to anchor coatings to the substrate in the manufacture of food-packaging cellophane.5 wt% of the rubber product.1200 177.170 176. Catalyst for epoxy resins used as the food contact surface of paper and paperboard in contact with fatty. Modifier for urea-formaldehyde and melamine-formaldehyde resins for use as a component of the coated or uncoated food-contact surface of paper and paperboard in contact with fatty. Catalyst and crosslinking agent for epoxy resins used in resinous and polymeric coatings applied as a continuous film or enamel over a metal substrate or applied as a continuous film or enamel to any suitable substrate provided that the coating serves as a functional barrier between the food and the substrate and is intended for repeated food-contact use.20 173.1200 177. transporting. Adjuvant in the preparation of slimicides used as antimicrobial agents to control slime in the manufacture of paper and paperboard. and as a resin to anchor coatings to substrate. and dry food. Modifier for melamine-formaldehyde resins for use as the basic polymer in cellophane. or holding food.FDA Status Dow provides the following FDA Status Summary for the convenience of our customers. as a modifier for melamine-formaldehyde resins used in cellophane. and/or diffusor systems at a maximum level of 1. Polyamides from vegetable oil acids and sebacic acid for use in side seam and can-end cements.5 wt% based on the monomers. not to exceed 1.180 176.300 175.180 176. applied to the sugar mill grinding.320 173. Catalyst for epoxy resins and component of polyamides for use in xylene-formaldehyde resins condensed with 4. Catalyst for epoxy resins and component of polyamides for use in zinc-silicon dioxide matrix coatings. aqueous. aqueous. Accelerator in vulcanization of rubber articles intended for repeated use. Component of the coated or uncoated food-contact surface of paper and paperboard in contact with dry food (as a crosslinking agent in polymerization).390 176. Formulation of defoaming agents used in the manufacture of paper and paperboard prior to and during the sheet forming operation.4’-iso-propylidenediphenol epichlorohydrin epoxy resins. Polyamides from dimerized vegetable oils for use as adjuncts for epoxy resins. Modifier for urea-formaldehyde resins for use as the basic polymer in cellophane and as a resin to anchor coatings to substrate. crusher. Diethylenetriamine (EDA) Triethylenetetramine (DETA) ✔ ✔ Tetraethylenepentamine (TETA) ✔ Aminoethylethanolamine (TEPA) ✔ (AEEA) ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ ✔ 39 . Furthermore. safe. it is the responsibility of the user to determine that any such use is suitable.Federal Regulations (21 CFR) to determine any limitations or restrictions on the proposed use. and FDA-compliant. Patent 4. al.892 (Lubrizol. Bulekova.360. 10. et. N. 58.341. Kokai 76 20.082 (The Lubrizol Corporation..B.P. 25.018. 54. Patent 184. 2. 1988.481. Res. U. News.941. 15. 12/8/61). 9. 17. U.S.539..623.094 (Lubrizol Corp. DE 2. 22.. 10. 95.S. and Narducy. .310. U. Patent 3.. European Patent Application 411. G. J. Prod. J. Patent 3. Vol.T. 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