111-42-2

Basic information

• Product Name: diethanolamine
• Synonyms: 2,2'-Iminobis[ethanol];2,2'-Iminodi-1-ethanol;2-[(2-Hydroxyethyl)amino]ethanol;Aliphatic amine;Bis(hydroxyethyl)amine;Dabco DEOA-LF;dela;Diaethanolamin
• CAS NO: 111-42-2
• Molecular Formula: C₄H₁₁NO₂
• Molecular Weight: 105.14
• EINECS: 203-868-0
• Product Categories: Pharmaceutical Intermediates;Thanolamine Series;Analytical Chemistry;Mass Spectrometry;Matrix Materials (FABMS & liquid SIMS);Biological Buffers;Buffers A to Z;Amino Alcohols;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;ACS Grade;Essential Chemicals;Inorganic Salts;Research Essentials;Solutions and Reagents;Chemical raw materials
• Mol File: 111-42-2.mol
• Article Data: 60

Chemical Properties

• Melting Point: 28 °C(lit.)
• Boiling Point: 268 °C
• Flash Point: 280 °F
• Appearance: APHA: ≤15/Viscous Liquid or Low Melting Solid
• Density: 1.097 g/mL at 25 °C(lit.)
• Vapor Density: 3.6 (vs air)
• Vapor Pressure: <0.98 atm ( 100 °C)
• Refractive Index: n20/D 1.477(lit.)
• Storage Temp.: Store at RT
• Solubility: H2O: 1 M at 20 °C, clear, colorless
• PKA: 8.88(at 25℃)
• Explosive Limit: 2.1-10.6%(V)
• Water Solubility: MISCIBLE
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with carbon dioxide, strong acids, strong oxidizing agents. Deliquescent.
• Merck: 14,3107
• BRN: 605315
• CAS DataBase Reference: diethanolamine(CAS DataBase Reference)
• NIST Chemistry Reference: diethanolamine(111-42-2)
• EPA Substance Registry System: diethanolamine(111-42-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-38-41-48/22
• Safety Statements: 26-36/37/39-46
• RIDADR: 3267
• WGK Germany: 1
• RTECS: KL2975000
• F: 3
• TSCA: Yes
• PackingGroup: II
• Hazardous Substances Data: 111-42-2(Hazardous Substances Data)

Usage

Description

Diethanolamine is an organic base which has been used as an emulsifying and dispersing agent.It can also be used as a basic buffer, with optimal pH about pH 9, if titrated with HCl or other acid. Other uses include: to "scrub" gases, as a chemical intermediate, as humectant or softening agent.

Chemical Properties

The USP32–NF27 describes diethanolamine as a mixture of ethanolamines consisting largely of diethanolamine. At about room temperature it is a white, deliquescent solid. Above room temperature diethanolamine is a clear, viscous liquid with a mildly ammoniacal odor. Diethanolamine is used as surface-active agent in metal-cutting fluids and oils, as a corrosion inhibitor, as a dispersant in agricultural chemical formulations, and as an intermediate in the production of other compounds such as fatty acid condensates of diethanolamine which are extensively used in soaps and cosmetics as emulsifiers, thickeners, wetting agents and detergents (Beyer et al., 1983). In the cosmetic formulations, the concentration of diethanolamine may range from 1 to 25% (National Toxicology Program, 1999a).

Uses

Different sources of media describe the Uses of 111-42-2 differently. You can refer to the following data:
1. Diethanolamine similar to triethanolamine (T775580) is used as a surfactant. It also has the potential to be a corrosion inhibitor by means of chemisorption.
2. To scrub gases as indicated under ethanolamine. Diethanolamine can be used with cracking gases and coal or oil gases which contain carbonyl sulfide that would react with monoethanolamine. As rubber chemicals intermediate. In the manufacture of surface active agents used in textile specialties, herbicides, petroleum demulsifiers. As emulsifier and dispersing agent in various agricultural chemicals, cosmetics, and pharmaceuticals. In the production of lubricants for the textile industry. As humectant and softening agent. In organic syntheses.
3. Diethanolamine is used in the production ofsurface-active agents and lubricants for thetextile industry; as an intermediate for rubberchemicals; as an emulsifier; as a humectantand softening agent; as a detergent in paints,shampoos, and other cleaners; and as anintermediate in resins and plasticizers.

Preparation

Diethanolamine is prepared commercially by the ammonolysis of ethylene oxide. The reaction yields a mixture of monoethanolamine, diethanolamine, and triethanolamine which is separated to obtain the pure products.

Definition

ChEBI: A member of the class of ethanolamines that is ethanolamine having a N-hydroxyethyl substituent.

Production Methods

Diethanolamine is produced with monoethanolamine and triethanolamine by ammonolysis of ethylene oxide; diethanolamine is then separated by distillation (Mullins 1978). In 1984, 166.2 million pounds of diethanolamine were produced in the United States (USTIC 1985).

General Description

Oily colorless liquid or solid white crystals. Slight rotten fish or ammonia odor. Denser than water.

Air & Water Reactions

Water soluble.

Reactivity Profile

2,2'-Iminodiethanol is an aminoalcohol. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. 2,2'-Iminodiethanol is hygroscopic. 2,2'-Iminodiethanol may be sensitive to exposure to air and light. 2,2'-Iminodiethanol can react with oxidizing materials, acids, CO2, copper alloys, aluminum, zinc, galvanized iron and copper.

Health Hazard

The irritant action of diethanolamine on theeyes can be severe. Direct contact of thepure liquid can impair vision. Irritation onthe skin may be mild to moderate. Theacute oral toxicity of this compound waslow in test animals. The toxic symptomsinclude somnolence, excitement, and musclecontraction.LD50 value, oral (mice): 3300 mg/kgThe vapor pressure of diethanolamine isnegligibly low (<0.01 torr at 20°C (68°F)).At ordinary temperature, this compoundshould not cause any inhalation hazard. Themists, fumes, or vapors at high temperatures,however, can produce eye, skin, and respiratory tract irritation.In contrast to monoethanolamine, dieth anolamine administered to mice at 1125 mg/kg/day caused no change in maternal mortality, litter size, or percentage survival of thepups (Environmental Health Research andTesting 1987).

Flammability and Explosibility

Nonflammable

Chemical Reactivity

Reactivity with Water : No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Flush with water; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Pharmaceutical Applications

Diethanolamine is primarily used in pharmaceutical formulations as a buffering agent, such as in the preparation of emulsions with fatty acids. In cosmetics and pharmaceuticals it is used as a pH adjuster and dispersant. Diethanolamine has also been used to form the soluble salts of active compounds, such as iodinated organic acids that are used as contrast media. As a stabilizing agent, diethanolamine prevents the discoloration of aqueous formulations containing hexamethylenetetramine-1,3-dichloropropene salts. Diethanolamine is also used in cosmetics.

Industrial uses

Diethanolamine undergoes reactions characteristic of secondary amines and of alcohols. Two industrially important reactions of the ethanolamines involve reaction with carbon dioxide or hydrogen sulfide to yield water soluble salts, and reaction with long chain fatty acids to form neutral ethanolamine soaps (Mullins 1978). Substituted ethanolamine compounds, such as soaps, are used extensively as emulsifiers, thickeners, wetting agents, and detergents in cosmetic formulations (including skin cleaners, creams, and lotions) (Beyer et al 1983). Diethanolamine is used as a dispersing agent in various agricultural chemicals, as an absorbent for acidic gases (hydrogen sulfide and carbon dioxide), as a humectant, as an intermediate in the synthesis of morpholine, as a surface-active agent in cutting fluids, as a corrosion inhibitor, as a component in textile specialty agents, and as a secondary vulcanization accelerator in the rubber industry. Diethanolamine is also used in cleaners and pharmaceutical ointments, in polyurethane formulations, in herbicides, and in a variety of organic syntheses (Beyer et al 1983; Mullins 1978; Windholz 1983). Diethanolamine is permitted in articles intended for use in the production, processing, or packaging of food (CFR 1981), and is permitted as a secondary direct food additive from use in delinting cottonseed in the production of cottonseed oil or meal cake (Fed. Reg. 1982). Because of the wide industrial and consumer uses, large amounts of this chemical are discharged into water and sewage in an unaltered form (Yordy and Alexander 1981).

Contact allergens

Diethanolamine is contained in many products, as a metalworking fuid. Traces may exist in other etha- nolamine-containing fuids.

Safety Profile

Poison by intraperitoneal route. Moderately toxic by ingestion and subcutaneous routes. Mildly toxic by skin contact. A severe eye and mild skin irritant. Experimental reproductive effects. Combustible when exposed to heat or flame; can react with oxidizing materials. To fight fire, use alcohol foam, water, Co2, dry chemical. When heated to decomposition it emits toxic fumes such as NOx. See also AMINES.

Safety

Diethanolamine is used in topical and parenteral pharmaceutical formulations, with up to 1.5% w/v being used in intravenous infusions. Experimental studies in dogs have shown that intravenous administration of larger doses of diethanolamine results in sedation, coma, and death.Animal toxicity studies suggest that diethanolamine is less toxic than monoethanolamine, although in rats the oral acute and subacute toxicity is greater. Diethanolamine is said to be heptacarcinogenic in mice and has also been reported to induce hepatic choline deficiency in mice.Diethanolamine is an irritant to the skin, eyes, and mucous membranes when used undiluted or in high concentration. However, in rabbits, aqueous solutions containing 10% w/v diethanolamine produce minor irritation. The lethal human oral dose of diethanolamine is estimated to be 5–15g/kg body-weight. The US Cosmetic Ingredient Review Expert Panel evaluated diethanolamine and concluded that it is safe for use in cosmetic formulations designed for discontinuous, brief use followed by thorough rinsing from the surface of the skin. In products intended for prolonged contact with the skin, the concentration of ethanolamines should not exceed 5%. Diethanolamine should not be used in products containing N-nitrosating agents.LD50 (guinea pig, oral): 2.0g/kgLD50 (mouse, IP): 2.3g/kg LD50 (mouse, oral): 3.3g/kgLD50 (rabbit, skin): 12.2g/kg LD50 (rat, IM): 1.5g/kgLD50 (rat, IP): 0.12g/kgLD50 (rat, IV): 0.78g/kgLD50 (rat, oral): 0.71g/kgLD50 (rat, SC): 2.2g/kg

Potential Exposure

Diethanolamine is present in machining and grinding fluids and has been detected in workplace air in the metal manufacturing industry. It was present in bulk cutting fluids at levels ranging from 4 to 5% (Kenyon et al., 1993). Diethanolamine has also been reported to be present in wetting fluids used in road paving. A level of 0.05 mg/m3 was detected in a stationary sample at a slurry machine discharging a bitumen emulsion containing 0.2% of the amine. All personal exposures were below the detection limit (0.02 mg/m3) (Levin et al., 1994). In a German study (1992–94), diethanolamine was measured in samples of metalworking fluids in a range of 0–44% (n = 69). The number of samples with diethanolamine present steadily declined from 90% to 60% over the study period (Pfeiffer et al., 1996).

Carcinogenicity

When DEA was administered cutaneously to pregnant rats and rabbits during organogenesis, developmental toxicity (skeletal variations) was observed only in the rat and only at doses causing significant maternal toxicity. The 2003 ACGIH threshold limit valuetime- weighted average (TLV-TWA) is 3ppm (13mg/m3).

Metabolism

Treatment of Wistar or Sherman rats with diethanolamine caused increases in the formation of hepatic phospholipids (Artom et al 1949). In addition, dietary administration led to incorporation of ethanolamine into hepatic phospholipids (Artom et al 1949), and repeated oral administration of diethanolamine in drinking water (one to three wk) at a dose of 320 mg/kg/d was found to reduce the level of incorporation of ethanolamine and choline into hepatic and renal phospholipids in Sprague-Dawley rats (Barbee and H?rtung 1979b). Dermal absorption of diethanolamine is suggested to occur in rats since Nnitrosodiethanolamine was excreted in the urine of male Sprague-Dawley rats which had been administered diethanolamine by dermal application and given nitrite in their drinking water (Preussman et al 1981).

storage

Diethanolamine is hygroscopic and light- and oxygen-sensitive; it should be stored in an airtight container, protected from light, in a cool, dry place.

Purification Methods

Fractionally distil the amine twice, then fractionally crystallise it from its melt. Its solubility in H2O is 10% at 20o. [Perrin & Dempsey Buffers for pH and Metal Ion Control Chapman & Hall, London 1974, Beilstein 4 H 283, 4 II 729, 4 III 689, 4 IV 1514.]

Incompatibilities

Diethanolamine is a secondary amine that contains two hydroxy groups. It is capable of undergoing reactions typical of secondary amines and alcohols. The amine group usually exhibits the greater activity whenever it is possible for a reaction to take place at either the amine or a hydroxy group.Diethanolamine will react with acids, acid anhydrides, acid chlorides, and esters to form amide derivatives, and with propylene carbonate or other cyclic carbonates to give the corresponding carbonates. As a secondary amine, diethanolamine reacts with aldehydes and ketones to yield aldimines and ketimines. Diethanolamine also reacts with copper to form complex salts. Discoloration and precipitation will take place in the presence of salts of heavy metals.

Waste Disposal

Controlled incineration; incinerator equipped with a scrubber or thermal unit to reduce nitrogen oxides emissions

Regulatory Status

Included in the FDA Inactive Ingredients Database (IV infusions, ophthalmic solutions, and topical preparations). Included in medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.

InChI:InChI=1/C4H11NO2/c6-3-1-5-2-4-7/h5-7H,1-4H2

Synthetic route

oxirane (75-21-8) + ethanolamine (141-43-5) → triethanolamine (102-71-6) + 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
With ammonia; ZSM-5 type zeolite ion exchange with lanthanum at 45℃; under 75007.5 Torr; Industry scale; Adiabatic conditions;	A 91.1% B 7.6%
With ammonia In water Continous process;	A 85.3% B 9.3%
With ammonia; ZSM-5 type zeolite ion exchange with lanthanum at 45℃; under 75007.5 Torr; Adiabatic conditions; Industry scale;	A 76.6% B 9.9%
In water Industry scale;
With ammonia; La/zeolites(ZSM-5) at 45℃; under 75007.5 Torr;

C9H19NO2 (1586805-11-9) → 2-pentanol (584-02-1) + 1-(2-hydroxyethyl)-2-ethyl-3-methylpyrrole + 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
With potassium hydroxide Reflux;	A n/a B 81% C n/a

2,2-hexamethylene-3-(2-hydroxyethyl)oxazolidine (91322-91-7) → cycloheptanol (502-41-0) + 1-(2-hydroxyethyl)-5,6,7,8-tetrahydrocyclohepta(b)pyrrole (91322-87-1) + 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
With potassium hydroxide Reflux;	A n/a B 76% C n/a

2-Spirocyclohexyl-3-(β-hydroxyethyl)oxazolidine (2359-11-7) → 1-(2-hydroxyethyl)-4,5,6,7-tetrahydro-1H-indole (51265-34-0) + 2,2'-iminobis[ethanol] (111-42-2) + cyclohexanol (108-93-0)

Conditions	Yield
With potassium hydroxide for 4h; Product distribution; Heating; alcoholates(C1-C4) of K, Na, Li, Ba, Ba, Al as reagents;	A 73% B n/a C n/a
With potassium hydroxide for 4h; Heating; CH3ONa as reagent;	A 73% B n/a C n/a

2,2-dipropyl-3-(2-hydroxyethyl)oxazolidine (91322-93-9) → heptan-4-ol (589-55-9) + 1-(2-hydroxyethyl)-2-propyl-3-ethylpyrrole (91322-89-3) + 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
With potassium hydroxide Reflux;	A n/a B 64% C n/a

2-(6-Methyl-1-oxa-4-aza-spiro[4.5]dec-4-yl)-ethanol (106345-17-9) → 2-Methylcyclohexanol (583-59-5) + 2-(7-Methyl-4,5,6,7-tetrahydro-indol-1-yl)-ethanol (106345-21-5) + 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
With potassium hydroxide Heating; CH3ONa as reagent;	A n/a B 59% C n/a

C13H27NO2 (1586805-13-1) → 5-nonanol (623-93-8) + 2-butyl-1-(2-hydroxyethyl)-3-propylpyrrole (1586805-19-7) + 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
With potassium hydroxide Reflux;	A n/a B 53% C n/a

C14H29NO2 (69470-38-8) → 1-Decanol (112-30-1) + 1-(2-hydroxyethyl)-3-octylpyrrole (1586805-20-0) + 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
With potassium hydroxide Reflux;	A n/a B 53% C n/a

oxirane (75-21-8) + ammonia (7664-41-7) → triethanolamine (102-71-6) + ethanolamine (141-43-5) + 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
water at 48.84 - 76.84℃; under 12751.3 Torr; for 0.25h;	A 7.7% B 52.1% C 40.2%

ethylene glycol (107-21-1) → piperazine (110-85-0) + ethanolamine (141-43-5) + 2-(2-Aminoethylamino)ethanol (111-41-1) + ethylenediamine (107-15-3) + 1,5-diamino-3-azapentane (111-40-0) + 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
Stage #1: ethylene glycol With ammonia; hydrogen at 150℃; under 150015 Torr; Stage #2: copper oxide; graphite; molybdenum oxide; nickel oxide; zirconium dioxide; mixture of at 170℃; under 150015 Torr;	A 6.8% B 29% C 5.7% D 49.5% E 3.9% F 1.7%
With ammonia; hydrogen at 170 - 180℃; under 150015 Torr; Conversion of starting material;
With ammonia; water; hydrogen at 180℃; under 150015 Torr; Conversion of starting material;
With ammonia; hydrogen at 150 - 170℃; under 150015 Torr; Conversion of starting material;
With ammonia; hydrogen at 200℃; under 150015 Torr; Conversion of starting material;

C12H17NO2 (495419-32-4) → 1-(2-hydroxyethyl)-2-phenylpyrrole + 1-Phenylethanol (98-85-1, 13323-81-4) + 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
With potassium hydroxide Reflux;	A 34% B n/a C n/a

C9H19NO2 → i-Amyl alcohol (123-51-3) + 1-(2-hydroxyethyl)-3-isopropylpyrrole + 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
With potassium hydroxide Reflux;	A n/a B 30% C n/a

2-(2,2-dimethyl-oxazolidin-3-yl)-ethanol (80136-05-6) → N-hydroxy-2 ethyl-1 methyl-2 pyrrole (104803-80-7) + 2,2'-iminobis[ethanol] (111-42-2) + isopropyl alcohol (67-63-0)

Conditions	Yield
With potassium hydroxide Reflux;	A 20% B n/a C n/a

oxirane (75-21-8) → ethanolamine (141-43-5) + 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
With ammonia at 79.84℃; under 60006 Torr;
With ammonia at 130℃; under 82376.9 Torr;
With ammonia at 110℃; Temperature; Reagent/catalyst;

oxirane (75-21-8) → 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
With ammonia; water at 100℃; under 44130.5 - 58840.6 Torr;
With ammonia

oxirane (75-21-8) → triethanolamine (102-71-6) + 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
With ammonia; water; ethanolamine at 15℃;
With ammonia In water
With ammonia; water; ethanolamine at 15℃;

pyridine (110-86-1) + triethanolamine (102-71-6) + dibenzoyl peroxide (94-36-0) → Glycolaldehyde (141-46-8) + 2,2'-iminobis[ethanol] (111-42-2)

N,N-bis-(2-hydroxy-ethyl)-hydroxylamine (95073-63-5) → 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
With hydrogenchloride; zinc at 0℃;

tris(2-hydroxyethyl)amine-N-oxide (7529-23-9) + furan-2,3,5(4H)-trione pyridine (1:1) → triethanolamine (102-71-6) + 2,2'-iminobis[ethanol] (111-42-2)

tris(2-hydroxyethyl)amine-N-oxide (7529-23-9) → triethanolamine (102-71-6) + 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
With sodium hydroxide
With water; zinc beim Erhitzen mit Natronlauge;

glycolonitrile (107-16-4) → 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
With methanol; nickel at 100℃; Hydrogenation;

2-chloro-ethanol (107-07-3) → 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
With ammonia

oxirane (75-21-8) → triethanolamine (102-71-6) + ethanolamine (141-43-5) + 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
With ammonia; wofatit KPS at 80℃; under 44253.5 Torr; for 0.25h; Product distribution; 10 - 30 min, water as a catalyst;	A 10.8 % Chromat. B 55.5 % Chromat. C 33.7 % Chromat.
With ammonia In water at 60℃;
With ammonia In water under 90009 - 105011 Torr; Heating;

triethanolamine (102-71-6) → acetaldehyde (75-07-0) + 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
In water Mechanism; Rate constant; radiolysis;

bis(2-hydroxyethyl)carbamate (116849-46-8) → carbon dioxide (124-38-9) + 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
In water at 25℃; Thermodynamic data; Equilibrium constant; ΔH,ΔG, ΔS;

sodium diethanolamine carbamate → 2,2'-iminobis[ethanol] (111-42-2)

Conditions	Yield
With sodium hydroxide; sodium perchlorate; sodium hydrogencarbonate at 29.9 - 57.9℃; Equilibrium constant;

2,2'-iminobis[ethanol] (111-42-2) + 1-Bromooctadecane (112-89-0) → N,N-diethanolstearylamine (10213-78-2)

Conditions	Yield
In acetonitrile Heating;	100%
With potassium carbonate; potassium iodide In acetonitrile	100%
With potassium hydrogencarbonate; potassium iodide In acetonitrile for 3h; Heating / reflux;	100%
With 2-pentanol das Hydrobromid ensteht;

benzyl bromide (100-39-0) + 2,2'-iminobis[ethanol] (111-42-2) → N-benzyl-diethanolamine (101-32-6)

Conditions	Yield
With potassium carbonate In acetone Reflux;	100%
With potassium carbonate In acetone for 8h; Heating;	97%
With potassium carbonate In acetone for 8h; Heating / reflux;	97%

phenyl isocyanate (103-71-9) + 2,2'-iminobis[ethanol] (111-42-2) → 1,1-[Di-(2-hydroxyethyl)]-3-phenylurea (20074-78-6)

Conditions	Yield
In dichloromethane	100%
In benzene
In dichloromethane; toluene at 20℃;
In dichloromethane at 20℃; for 0.0166667h; Inert atmosphere;	1.14 g

2,2'-iminobis[ethanol] (111-42-2) → bis(2-bromoethyl)amine (3890-99-1)

Conditions	Yield
With hydrogen bromide Reflux;	100%
With hydrogen bromide

1,2-bis(2-chloroethoxy)ethane (112-26-5) + 2,2'-iminobis[ethanol] (111-42-2) → 3,12-Bis(2-hydroxyethyl)-6,9-dioxa-3,12-diaza-1,14-tetradecanediol (78995-84-3)

Conditions	Yield
With sodium carbonate In xylene for 48h; Heating;	100%
With sodium carbonate In xylene Yield given;

2-[2-(vinyloxy)ethoxymethyl]oxirane (16801-19-7) + 2,2'-iminobis[ethanol] (111-42-2) → N-<2-hydroxy-2-(2-vinyloxyethoxymethyl)ethyl>-bis(2-hydroxyethyl)amine (122278-65-3)

Conditions	Yield
at 55 - 60℃; under 760 Torr; for 2h;	100%
at 20 - 60℃; for 1.5h;	80%

di-tert-butyl dicarbonate (24424-99-5) + 2,2'-iminobis[ethanol] (111-42-2) → N,N-bis(2-hydroxyethyl)-O-tert-butylcarbamate (103898-11-9)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 24h;	100%
In tetrahydrofuran for 24h; Ambient temperature;	100%
In tetrahydrofuran at 20℃; for 24h;	100%

2-(vinyloxy)ethyl isothiocyanate (59565-09-2) + 2,2'-iminobis[ethanol] (111-42-2) → 1,1-Bis-(2-hydroxy-ethyl)-3-(2-vinyloxy-ethyl)-thiourea (121612-58-6)

Conditions	Yield
	100%

2,2'-iminobis[ethanol] (111-42-2) + phosphonic acid diethyl ester (762-04-9) → bis-(2-hydroxy-ethyl)-amidophosphoric acid diethyl ester (2359-07-1)

Conditions	Yield
With potassium carbonate; potassium hydrogencarbonate; tetrabutylammomium bromide In tetrachloromethane; dichloromethane at 15 - 20℃; for 2h;	100%
With tetrachloromethane; triethylamine In chloroform at 10 - 20℃;
With tetrabutylammomium bromide; potassium carbonate; potassium hydrogencarbonate In tetrahydrofuran; tetrachloromethane for 1h; Ambient temperature; Yield given;

carbon monoxide (201230-82-2) + 2,2'-iminobis[ethanol] (111-42-2) + cyclohexanecarbaldehyde (2043-61-0) → 2-(2-cyclohexyl-oxazolidin-3-yl)-ethanol (55135-29-0)

Conditions	Yield
With 1-Methylpyrrolidine; water; 3>PF6 at 140℃; under 51714.8 Torr; for 6h;	100%

3-chloro-4-fluoronitrobenzene (350-30-1) + 2,2'-iminobis[ethanol] (111-42-2) → 2-[(2-Chloro-4-nitro-phenyl)-(2-hydroxy-ethyl)-amino]-ethanol (65976-57-0)

Conditions	Yield
at 130℃; for 2h;	100%
In dimethyl sulfoxide	64%

2,2'-iminobis[ethanol] (111-42-2) → bis-(2-chloroethyl)amine hydrochloride (821-48-7)

Conditions	Yield
With thionyl chloride In 1,2-dichloro-ethane at 50℃; for 3h;	100%
With thionyl chloride In dichloromethane for 24h;	100%
With thionyl chloride In chloroform at 50℃; for 4h; Temperature;	98.8%

2,2'-iminobis[ethanol] (111-42-2) + tert-butylchlorodiphenylsilane (58479-61-1) → N,N-[bis(2-tert-butyldiphenylsilyloxyethyl)]amine (189279-33-2)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 0.5h;	100%
With triethylamine; dmap In dichloromethane at 0 - 20℃; for 20h; Product distribution / selectivity;	90%
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 20h;	90%
With dmap; triethylamine In methanol; dichloromethane	2.53 g (2.13 mmol, 29%)
With dmap; triethylamine In methanol; dichloromethane	2.53 g (2.13 mmol, 29%)

2,2'-iminobis[ethanol] (111-42-2) + (4R,5R)-2-thioxo-4,5-bis(tert-butyloxycarbonyl)-1,3-dioxolane (464188-90-7) → (2R,3R)-di-tert-butyl 2-[bis(2-hydroxyethyl)]thiocarbamoyloxy-3-hydroxysuccinate

Conditions	Yield
In dichloromethane at 20℃; for 0.5h;	100%

lauryl acrylate (2156-97-0) + 2,2'-iminobis[ethanol] (111-42-2) → 3-[bis-(2-hydroxy-ethyl)-amino]-propionic acid dodecyl ester

Conditions	Yield
at 50℃; Michael addition;	100%

2,2'-iminobis[ethanol] (111-42-2) + C50H98O25 → C54H109NO27

Conditions	Yield
at 50℃; Michael addition;	100%

[4-(4-Benzyloxycarbonylaminobutyl)phenoxy]acetic acid ethyl ester (587880-74-8) + 2,2'-iminobis[ethanol] (111-42-2) → [4-(4-{[N,N-bis-(2-hydroxyethyl)carbamoyl]methoxy}phenyl)butyl]carbamic acid benzyl ester (847201-08-5)

Conditions	Yield
With ethanol at 70℃; for 72h;	100%

2,2'-iminobis[ethanol] (111-42-2) + DTP2 (308795-79-1) → C4H11NO2*C20H30O2 (467222-19-1)

Conditions	Yield
In tetrahydrofuran; methanol for 1h;	100%

2,2'-iminobis[ethanol] (111-42-2) + hexadecanyl bromide (112-82-3) → 2,2'-(hexadecylazanediyl)diethanol (18924-67-9)

Conditions	Yield
With potassium hydrogencarbonate; potassium iodide In acetonitrile for 3h; Reflux;	100%
With potassium carbonate; potassium iodide In acetonitrile for 12h; Inert atmosphere; Reflux;	96.1%
With potassium carbonate; potassium iodide In acetonitrile
With N-ethyl-N,N-diisopropylamine In methanol for 96h; Reflux;

1-[6-fluoro-8-methoxy-3-({[2-methyl-4-(trifluoromethoxy)benzyl]amino}carbonyl)-4-oxo-1-(2,2,2-trifluoroethyl)-1,4-dihydroquinolin-7-yl]piperidine-4-carboxylic acid (945892-54-6) + 2,2'-iminobis[ethanol] (111-42-2) → 1-[6-fluoro-8-methoxy-3-({[2-methyl-4-(trifluoromethoxy)benzyl]amino}carbonyl)-4-oxo-1-(2,2,2-trifluoroethyl)-1,4-dihydroquinolin-7-yl]piperidine-4-carboxylic acid diethanolamine salt (945892-80-8)

Conditions	Yield
In water; acetonitrile at 20℃;	100%

(2′Z-3′E)-6-bromoindirubin-3′-[O-(2-bromoethyl)oxime] (1067884-35-8) + 2,2'-iminobis[ethanol] (111-42-2) → (2'Z-3'E)-6-bromoindirubin-3'-[O-(2-(N,N-(2-hydroxyethyl)amino)ethyl)oxime] (1067884-43-8)

Conditions	Yield
In N,N-dimethyl-formamide at 50℃;	100%

4-methoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylboronic acid (1159105-82-4) + 2,2'-iminobis[ethanol] (111-42-2) → 2-(4-methoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,6,2-dioxazaborocane (1159105-98-2)

Conditions	Yield
In tetrahydrofuran at 25℃; for 1h; Inert atmosphere;	100%

4-ethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylboronic acid (1159105-85-7) + 2,2'-iminobis[ethanol] (111-42-2) → 2-(4-ethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,6,2-dioxazaborocane (1159106-01-0)

Conditions	Yield
In tetrahydrofuran at 25℃; for 1h; Inert atmosphere;	100%

4-propoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylboronic acid (245435-17-0) + 2,2'-iminobis[ethanol] (111-42-2) → 2-(4-propoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,6,2-dioxazaborocane (1159106-04-3)

Conditions	Yield
In tetrahydrofuran at 25℃; for 1h; Inert atmosphere;	100%

4-butoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylboronic acid (1159105-89-1) + 2,2'-iminobis[ethanol] (111-42-2) → 2-(4-butoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,6,2-dioxazaborocane (1159106-07-6)

Conditions	Yield
In tetrahydrofuran at 25℃; for 1h; Inert atmosphere;	100%

4-pentyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylboronic acid (1159105-92-6) + 2,2'-iminobis[ethanol] (111-42-2) → 2-(4-pentyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,6,2-dioxazaborocane (1159106-10-1)

Conditions	Yield
In tetrahydrofuran at 25℃; for 1h; Inert atmosphere;	100%

4-hexyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylboronic acid (1159105-95-9) + 2,2'-iminobis[ethanol] (111-42-2) → 2-(4-hexyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,6,2-dioxazaborocane (1159106-14-5)

Conditions	Yield
In tetrahydrofuran at 25℃; for 1h; Inert atmosphere;	100%

C28H20ClN5O5S2 (1112459-57-0) + 2,2'-iminobis[ethanol] (111-42-2) → 2-Hydroxy-N-(2-hydroxyethyl)ethanaminium 3-(2-{4-[2-amino-6-({[2-(4-chlorophenyl)-1,3-thiazol-4-yl]methyl}thio)-3,5-dicyanopyridin-4-yl]phenoxy}ethoxy)-3-oxopropanoate (1112459-39-8)

Conditions	Yield
In 1,4-dioxane; water at 20℃;	100%

Ixazomib (1072833-77-2) + 2,2'-iminobis[ethanol] (111-42-2) → 2,5-dichloro-N-[(2-((1R)-3-methyl-1-[1,3,6,2]-dioxaborolan-2-yl)-butylamino)-2-oxyethyl]benzamide

Conditions	Yield
In ethyl acetate at 20℃; for 2h; Product distribution / selectivity;	100%

3-(2,6-dichloropyridin-4-yl)-4-methylaniline + 2,2'-iminobis[ethanol] (111-42-2) → 2,2'-((4-(5-amino-2-methylphenyi)-6-chloropyridin-2-yl)azanediyl)diethanol

Conditions	Yield
at 105℃;	100%

Upstream product

• 107-16-4 glycolonitrile 
• 107-21-1 ethylene glycol 
• 106345-17-9 2-(6-Methyl-1-oxa-4-aza-spiro[4.5]dec-4-yl)-ethanol 
• 102-71-6 triethanolamine 
• 2359-11-7 2-Spirocyclohexyl-3-(β-hydroxyethyl)oxazolidine 
• 75-21-8 oxirane 
• 107-07-3 2-chloro-ethanol 
• 7529-23-9 tris(2-hydroxyethyl)amine-N-oxide 
• 110-86-1 pyridine 
• 94-36-0 dibenzoyl peroxide 
• 141-43-5 ethanolamine 
• 141-46-8 Glycolaldehyde 
• 1116-54-7 N-nitrosodiethanolamine 
• 1586805-16-4 2-butyl-2-methyl-3-(2-hydroxyethyl)oxazolidine 

Downstream Products

• 95745-94-1 4-nitro-benzoic acid-{bis-[2-(4-nitro-benzoyloxy)-ethyl]-amide} 
• 4439-34-3 2,2'-(pyridin-2-ylazanediyl)bis(ethan-1-ol) 
• 4388-18-5 2-amino-1-phenylethanol 
• 101424-27-5 N,N-bis-(2-hydroxy-ethyl)-N'-(4-[2]pyridyl-phenyl)-thiourea 
• 108851-92-9 1-[bis-(2-hydroxy-ethyl)-amino]-3-o-tolyloxy-propan-2-ol 
• 6312-66-9 6- purin 
• 3197-06-6 N,N-bis(2-hydroxyethyl)ethylidenediamine 
• 66354-57-2 1-(bis(2-hydroxyethyl)amino)-3-(decyloxy)propan-2-ol 
• 23008-81-3 2-(8-methyl-1-oxa-4,8-diaza-spiro[4.5]dec-4-yl)-ethanol 
• 66354-56-1 1-(bis(2-hydroxyethyl)amino)-3-(octyloxy)propan-2-ol 
• 6712-98-7 1-[N,N-bis(2-hydroxyethyl)amino]-2-propanol 
• 334-22-5 N,N-bis(chloro-2-ethyl)amine 
• 21569-01-7 bis-(2-nitryloxy-ethyl)-amine; nitrate 
• 4185-47-1 nitro-bis-(2-nitryloxy-ethyl)-amine 

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Relevant articles and documents

Chain Decomposition of Aqueous Trietanolamine

A radiation-induced chain decomposition of aqueous triethanolamine into acetaldehyde and diethanolamine is reported.Chain length over 1000 have been observed, depending on pH, concentration, and radiation intensity.The chain propagation steps include OH group migration in the 2-hydroxy-1-(diethanolamino)ethyl radical and NR2 migration in 1-hydroxy-2-(diethanolamine)ethyl radical, each producing a 2-hydroxy-2-(diethanolamine)ethyl radical.Free-radical spectra and rate constants are given.Studies of diethanolamine and diethylethanolamine solutions gave similar free-radical spectra but much shorter chains.

Temperature dependency of the equilibrium constant for the formation of carbamate from diethanolamine

The equilibrium constant for the formation of diethanolamine carbamate was determined experimentally at (303, 313, 323, and 331) K for ionic strengths up to 1.8 mol dm-3, the inert electrolyte being NaClO4. A linear relationship was found to hold between log K and I0.5. The thermodynamical constant has been determined and expressed by the equation log K1 = -5.12 + 1.781 × 103 K/T.

Boronic Ester Based Vitrimers with Enhanced Stability via Internal Boron-Nitrogen Coordination

Boron-containing polymers have many applications resulting from their prominent properties. Organoboron species with reversible B-O bonds have been successfully employed for the fabrication of various self-healing/healable and reprocessable polymers. However, the application of the polymers containing boronic ester or boroxine linkages is limited because of their instability to water. Herein, we report the hydrolytic stability and dynamic covalent chemistry of the nitrogen-coordinating cyclic boronic diester (NCB) linkages, and a new class of vitrimers based on NCB linkages is developed through the chemical reactions of reactive hydrogen with isocyanate. Thermodynamic and kinetic studies demonstrated that NCB linkages exhibit enhanced water and heat resistance, whereas the exchange reactions between NCB linkages can take place upon heating without any catalyst. The model compounds of NCBC-X1 and NCBC-X2 containing a urethane group and urea group, respectively, also showed higher hydrolytic stability compared to that of conventional boronic esters. Polyurethane vitrimers and poly(urea-urethane) vitrimers based on NCB linkages exhibited excellent solvent resistance and mechanical properties like general thermosets, which can be repaired, reprocessed, and recycled via the transesterification of NCB linkages upon heating. Especially, vitrimers based on NCB linkages presented improved stability to water and heat compared to those through conventional boronic esters because of the existence of N → B internal coordination. We anticipate that this work will provide a new strategy for designing the next generation of sustainable materials.

ZEOLITE CATALYZED PROCESS FOR THE AMINATION OF ALKYLENE OXIDES

The present invention relates to a process for the conversion of ethylene oxide to 2- aminoethanol and/or Di(2-hydroxyethyl)amine comprising (i) providing a catalyst comprising a zeolitic material comprising YO2 and X2O3 in its frame- work structure, wherein Y is a tetravalent element and X is a trivalent element, wherein the zeo- litic material has a framework-type structure selected from the group consisting of MFI and/or MEL, including MEL/MFI intergrowths, and wherein the zeolitic material contains one or more rare earth elements; (ii) providing a mixture in the liquid phase comprising ethylene oxide and ammonia; (iii) contacting the catalyst provided in (i) with the mixture in the liquid phase provided in (ii) for converting ethylene oxide to 2-aminoethanol and/or Di(2-hydroxyethyl)amine, wherein the catalyst provided in (i) is obtained and/or obtainable by a process comprising load- ing one or more salts of the one or more rare earth elements into the pores of the porous structure of the zeolitic material and optionally on the surface of the zeolitic material.

AgI/TMG-Promoted Cascade Reaction of Propargyl Alcohols, Carbon Dioxide, and 2-Aminoethanols to 2-Oxazolidinones

Chemical valorization of CO2 to access various value-added compounds has been a long-term and challenging objective from the viewpoint of sustainable chemistry. Herein, a one-pot three-component reaction of terminal propargyl alcohols, CO2, and 2-aminoethanols was developed for the synthesis of 2-oxazolidinones and an equal amount of α-hydroxyl ketones promoted by Ag2O/TMG (1,1,3,3-tetramethylguanidine) with a TON (turnover number) of up to 1260. By addition of terminal propargyl alcohol, the thermodynamic disadvantage of the conventional 2-aminoethanol/CO2 coupling was ameliorated. Mechanistic investigations including control experiments, DFT calculation, kinetic and NMR studies suggest that the reaction proceeds through a cascade pathway and TMG could activate propargyl alcohol and 2-aminoethanol through the formation of hydrogen bonds and also activate CO2.