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111-42-2

Basic Information
CAS No.: 111-42-2
Name: Diethanolamine
Article Data: 84
Molecular Structure:
Molecular Structure of 111-42-2 (Diethanolamine)
Formula: C4H11NO2
Molecular Weight: 105.137
Synonyms: 2,2-Iminodi-1-ethanol;2,2-Dihydroxydiethylamine;bis(2-hydroxyethyl)azanium;N,N-Diethanolamine;Diethanolamine (NF);Iminodiethanol;Bis(2-hydroxyethyl)amine;Diethylolamine;2-(2-hydroxyethylamino)ethanol;Di(2-hydroxyethyl)amine;Purified Isophthalic Acid;Diethanolamin 98%;Diethanolamin min. 85%;2,2'-iminodiethanol;Ethanol, 2,2-iminodi-;Diethanolamine (DEA);Diethylamine, 2,2-dihydroxy-;DEA;2, 2-Iminobis[ethanol];Ethanol, 2,2-iminobis-;2,2-Iminodiethanol;2-[(2-Hydroxyethyl)amino]ethanol;Ethanol,2,2'-iminobis-;
EINECS: 203-868-0
Density: 1.096 g/cm3
Melting Point: 28 °C(lit.)
Boiling Point: 268.389 °C at 760 mmHg
Flash Point: 137.778 °C
Solubility: miscible with water
Appearance: solid or viscous liquid
Hazard Symbols: HarmfulXn
Risk Codes: 22-38-41-48/22
Safety: 26-36/37/39-46
Transport Information: UN 1760
PSA: 52.49000
LogP: -1.04850
Synthetic route
75-21-8

oxirane

141-43-5

ethanolamine

A

102-71-6

triethanolamine

B

111-42-2

2,2'-iminobis[ethanol]

Conditions
ConditionsYield
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;
1586805-11-9

C9H19NO2

A

584-02-1

2-pentanol

B

1-(2-hydroxyethyl)-2-ethyl-3-methylpyrrole

C

111-42-2

2,2'-iminobis[ethanol]

Conditions
ConditionsYield
With potassium hydroxide Reflux;A n/a
B 81%
C n/a
91322-91-7

2,2-hexamethylene-3-(2-hydroxyethyl)oxazolidine

A

502-41-0

cycloheptanol

B

91322-87-1

1-(2-hydroxyethyl)-5,6,7,8-tetrahydrocyclohepta(b)pyrrole

C

111-42-2

2,2'-iminobis[ethanol]

Conditions
ConditionsYield
With potassium hydroxide Reflux;A n/a
B 76%
C n/a
2359-11-7

2-Spirocyclohexyl-3-(β-hydroxyethyl)oxazolidine

A

51265-34-0

1-(2-hydroxyethyl)-4,5,6,7-tetrahydro-1H-indole

B

111-42-2

2,2'-iminobis[ethanol]

C

108-93-0

cyclohexanol

Conditions
ConditionsYield
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
91322-93-9

2,2-dipropyl-3-(2-hydroxyethyl)oxazolidine

A

589-55-9

heptan-4-ol

B

91322-89-3

1-(2-hydroxyethyl)-2-propyl-3-ethylpyrrole

C

111-42-2

2,2'-iminobis[ethanol]

Conditions
ConditionsYield
With potassium hydroxide Reflux;A n/a
B 64%
C n/a
106345-17-9

2-(6-Methyl-1-oxa-4-aza-spiro[4.5]dec-4-yl)-ethanol

A

583-59-5

2-Methylcyclohexanol

B

106345-21-5

2-(7-Methyl-4,5,6,7-tetrahydro-indol-1-yl)-ethanol

C

111-42-2

2,2'-iminobis[ethanol]

Conditions
ConditionsYield
With potassium hydroxide Heating; CH3ONa as reagent;A n/a
B 59%
C n/a
1586805-13-1

C13H27NO2

A

623-93-8

5-nonanol

B

1586805-19-7

2-butyl-1-(2-hydroxyethyl)-3-propylpyrrole

C

111-42-2

2,2'-iminobis[ethanol]

Conditions
ConditionsYield
With potassium hydroxide Reflux;A n/a
B 53%
C n/a
69470-38-8

C14H29NO2

A

112-30-1

1-Decanol

B

1586805-20-0

1-(2-hydroxyethyl)-3-octylpyrrole

C

111-42-2

2,2'-iminobis[ethanol]

Conditions
ConditionsYield
With potassium hydroxide Reflux;A n/a
B 53%
C n/a
75-21-8

oxirane

7664-41-7

ammonia

A

102-71-6

triethanolamine

B

141-43-5

ethanolamine

C

111-42-2

2,2'-iminobis[ethanol]

Conditions
ConditionsYield
water at 48.84 - 76.84℃; under 12751.3 Torr; for 0.25h;A 7.7%
B 52.1%
C 40.2%
107-21-1

ethylene glycol

A

110-85-0

piperazine

B

141-43-5

ethanolamine

C

111-41-1

2-(2-Aminoethylamino)ethanol

D

107-15-3

ethylenediamine

E

111-40-0

1,5-diamino-3-azapentane

F

111-42-2

2,2'-iminobis[ethanol]

Conditions
ConditionsYield
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;
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    Diethanolamine

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  • 2,2'-Iminodiethanol

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    2,2'-Iminodiethanol

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Chemistry

Molecular Structure of Diethanolamine (CAS No.111-42-2):

Molecular Formula: C4H11NO2
Molecular Weight: 105.14
IUPAC Name: 2-(2-Hydroxyethylamino)ethanol 
CAS No: 111-42-2
EINECS: 203-868-0
H bond acceptors: 3
H bond donors: 3
Freely Rotating Bonds: 6
Polar Surface Area: 52.49 Å2
Index of Refraction: 1.465
Molar Refractivity: 27.24 cm3
Molar Volume: 98.3 cm3
Surface Tension: 43.5 dyne/cm
Density: 1.068 g/cm3
Flash Point: 137.8 °C 
Melting Point: 28 °C(lit.)
Enthalpy of Vaporization: 58.81 kJ/mol
Boiling Point: 268.4 °C at 760 mmHg
Vapour Pressure: 0.00104 mmHg at 25°C
Melting Point: 27-30 ºC
Refractive Index: 1.475-1.479
Water Solubility: Miscible
Sensitive: Hygroscopic
Classification Code: Drug / Therapeutic Agent;Pharmaceutic aid [alkalizing agent];Reproductive Effect;Skin / Eye Irritant;TSCA Flag T [Subject to the Section 4 test rule under TSCA];Tumor data
Product Categories: Pharmaceutical Intermediates;Thanolamine Series;Analytical Chemistry;Mass Spectrometry;Matrix Materials (FABMS liquid SIMS)

Uses

  As surfactant and corrosion inhibitor, Diethanolamine (CAS No.111-42-2) is used to remove hydrogen sulfide and carbon dioxide from natural gas.

Production

The reaction of Ethylene oxide with aqueous ammonia first produces Ethanolamine:
C2H4O + NH3 → H2NCH2CH2OH
which reacts with a second and third equivalent of Ethylene oxide to give Diethanolamine and Triethanolamine:
C2H4O + H2NCH2CH2OH → HN(CH2CH2OH)2
C2H4O + HN(CH2CH2OH)2 → N(CH2CH2OH)3
About 300M kg are produced annually in this way. The ratio of the products can be controlled by changing the stoichiometry of the reactants.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 2gm/kg (2000mg/kg)   "Documentation of the Threshold Limit Values and Biological Exposure Indices," 5th ed., Cincinnati, OH, American Conference of Governmental Industrial Hygienists, Inc., 1986Vol. 5, Pg. 197, 1986.
guinea pig LD50 skin 11900uL/kg (11.9mL/kg)   National Technical Information Service. Vol. OTS0516742,
mammal (species unspecified) LDLo oral 3gm/kg (3000mg/kg)   National Technical Information Service. Vol. OTS0520710,
mouse LD50 intraperitoneal 210mg/kg (210mg/kg)   National Technical Information Service. Vol. OTS0516742,
mouse LD50 oral 3300mg/kg (3300mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 29(11), Pg. 25, 1964.
rabbit LD50 oral 2200mg/kg (2200mg/kg)   Environmental Space Science. English Translation of Kosmicheskaya Biologiya Meditsina. 1967-70.Vol. 2, Pg. 289, 1968.
rabbit LD50 skin 7640uL/kg (7.64mL/kg) BEHAVIORAL: ATAXIA

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

MUSCULOSKELETAL: OTHER CHANGES
National Technical Information Service. Vol. OTS0516797,
rat LD50 intramuscular 1500mg/kg (1500mg/kg)   Environmental Space Science. English Translation of Kosmicheskaya Biologiya Meditsina. 1967-70.Vol. 2, Pg. 289, 1968.
rat LD50 intraperitoneal 120mg/kg (120mg/kg)   Environmental Space Science. English Translation of Kosmicheskaya Biologiya Meditsina. 1967-70.Vol. 2, Pg. 289, 1968.
rat LD50 intravenous 778mg/kg (778mg/kg)   Environmental Space Science. English Translation of Kosmicheskaya Biologiya Meditsina. 1967-70.Vol. 2, Pg. 289, 1968.
rat LD50 oral 620uL/kg (0.62mL/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: TREMOR

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
National Technical Information Service. Vol. OTS0516797,
rat LD50 subcutaneous 2200mg/kg (2200mg/kg)   Environmental Space Science. English Translation of Kosmicheskaya Biologiya Meditsina. 1967-70.Vol. 2, Pg. 289, 1968.

Consensus Reports

Community Right-To-Know List. Reported in EPA TSCA Inventory.

Safety Profile

Safety Information of Diethanolamine (CAS No.111-42-2):
Hazard Codes: HarmfulXn
Risk Statements: 22-38-41-48/22 
R22:Harmful if swallowed. 
R38:Irritating to skin. 
R41:Risk of serious damage to the eyes. 
R48/22:Harmful: danger of serious damage to health by prolonged exposure if swallowed.
Safety Statements: 26-36/37/39-46
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S46:If swallowed, seek medical advice immediately and show this container or label.
RIDADR: 3267
WGK Germany: 1
RTECS: KL2975000
F: 3
PackingGroup: II
Hazardous Substances Data: 111-42-2(Hazardous Substances Data)

Standards and Recommendations

OSHA PEL: TWA 3 ppm
ACGIH TLV: TWA 0.46 ppm (skin)

Analytical Methods

For occupational chemical analysis use NIOSH: Aminoethanol Compounds II 3509.

Specification

   Diethanolamine (CAS No.111-42-2), it also can be called 2,2'-Dihydroxydiethylamine ; 2,2'-Iminodiethanol ; Bis(2-hydroxyethyl)amine ; DEA .It is solid or viscous liquid with an amine odour.