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; |
Conditions | Yield |
---|---|
With potassium hydroxide Reflux; | A n/a B 81% C n/a |
2,2-hexamethylene-3-(2-hydroxyethyl)oxazolidine
A
cycloheptanol
B
1-(2-hydroxyethyl)-5,6,7,8-tetrahydrocyclohepta(b)pyrrole
C
2,2'-iminobis[ethanol]
Conditions | Yield |
---|---|
With potassium hydroxide Reflux; | A n/a B 76% C n/a |
2-Spirocyclohexyl-3-(β-hydroxyethyl)oxazolidine
A
1-(2-hydroxyethyl)-4,5,6,7-tetrahydro-1H-indole
B
2,2'-iminobis[ethanol]
C
cyclohexanol
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
A
heptan-4-ol
B
1-(2-hydroxyethyl)-2-propyl-3-ethylpyrrole
C
2,2'-iminobis[ethanol]
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
A
2-Methylcyclohexanol
B
2-(7-Methyl-4,5,6,7-tetrahydro-indol-1-yl)-ethanol
C
2,2'-iminobis[ethanol]
Conditions | Yield |
---|---|
With potassium hydroxide Heating; CH3ONa as reagent; | A n/a B 59% C n/a |
C13H27NO2
A
5-nonanol
B
2-butyl-1-(2-hydroxyethyl)-3-propylpyrrole
C
2,2'-iminobis[ethanol]
Conditions | Yield |
---|---|
With potassium hydroxide Reflux; | A n/a B 53% C n/a |
C14H29NO2
A
1-Decanol
B
1-(2-hydroxyethyl)-3-octylpyrrole
C
2,2'-iminobis[ethanol]
Conditions | Yield |
---|---|
With potassium hydroxide Reflux; | A n/a B 53% C n/a |
oxirane
ammonia
A
triethanolamine
B
ethanolamine
C
2,2'-iminobis[ethanol]
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
A
piperazine
B
ethanolamine
C
2-(2-Aminoethylamino)ethanol
D
ethylenediamine
E
1,5-diamino-3-azapentane
F
2,2'-iminobis[ethanol]
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; |
Conditions | Yield |
---|---|
With potassium hydroxide Reflux; | A 34% B n/a C n/a |
Conditions | Yield |
---|---|
With potassium hydroxide Reflux; | A n/a B 30% C n/a |
2-(2,2-dimethyl-oxazolidin-3-yl)-ethanol
A
N-hydroxy-2 ethyl-1 methyl-2 pyrrole
B
2,2'-iminobis[ethanol]
C
isopropyl alcohol
Conditions | Yield |
---|---|
With potassium hydroxide Reflux; | A 20% B n/a C n/a |
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; |
Conditions | Yield |
---|---|
With ammonia; water at 100℃; under 44130.5 - 58840.6 Torr; | |
With ammonia |
Conditions | Yield |
---|---|
With ammonia; water; ethanolamine at 15℃; | |
With ammonia In water | |
With ammonia; water; ethanolamine at 15℃; |
pyridine
triethanolamine
dibenzoyl peroxide
A
Glycolaldehyde
B
2,2'-iminobis[ethanol]
N,N-bis-(2-hydroxy-ethyl)-hydroxylamine
2,2'-iminobis[ethanol]
Conditions | Yield |
---|---|
With hydrogenchloride; zinc at 0℃; |
tris(2-hydroxyethyl)amine-N-oxide
A
triethanolamine
B
2,2'-iminobis[ethanol]
tris(2-hydroxyethyl)amine-N-oxide
A
triethanolamine
B
2,2'-iminobis[ethanol]
Conditions | Yield |
---|---|
With sodium hydroxide | |
With water; zinc beim Erhitzen mit Natronlauge; |
Conditions | Yield |
---|---|
With methanol; nickel at 100℃; Hydrogenation; |
Conditions | Yield |
---|---|
With ammonia |
oxirane
A
triethanolamine
B
ethanolamine
C
2,2'-iminobis[ethanol]
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; |
Conditions | Yield |
---|---|
In water Mechanism; Rate constant; radiolysis; |
bis(2-hydroxyethyl)carbamate
A
carbon dioxide
B
2,2'-iminobis[ethanol]
Conditions | Yield |
---|---|
In water at 25℃; Thermodynamic data; Equilibrium constant; ΔH,ΔG, ΔS; |
2,2'-iminobis[ethanol]
Conditions | Yield |
---|---|
With sodium hydroxide; sodium perchlorate; sodium hydrogencarbonate at 29.9 - 57.9℃; Equilibrium constant; |
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; |
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
2,2'-iminobis[ethanol]
1,1-[Di-(2-hydroxyethyl)]-3-phenylurea
Conditions | Yield |
---|---|
In dichloromethane | 100% |
In benzene | |
In dichloromethane; toluene at 20℃; | |
In dichloromethane at 20℃; for 0.0166667h; Inert atmosphere; | 1.14 g |
Conditions | Yield |
---|---|
With hydrogen bromide Reflux; | 100% |
With hydrogen bromide |
1,2-bis(2-chloroethoxy)ethane
2,2'-iminobis[ethanol]
3,12-Bis(2-hydroxyethyl)-6,9-dioxa-3,12-diaza-1,14-tetradecanediol
Conditions | Yield |
---|---|
With sodium carbonate In xylene for 48h; Heating; | 100% |
With sodium carbonate In xylene Yield given; |
2-[2-(vinyloxy)ethoxymethyl]oxirane
2,2'-iminobis[ethanol]
N-<2-hydroxy-2-(2-vinyloxyethoxymethyl)ethyl>-bis(2-hydroxyethyl)amine
Conditions | Yield |
---|---|
at 55 - 60℃; under 760 Torr; for 2h; | 100% |
at 20 - 60℃; for 1.5h; | 80% |
di-tert-butyl dicarbonate
2,2'-iminobis[ethanol]
N,N-bis(2-hydroxyethyl)-O-tert-butylcarbamate
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
2,2'-iminobis[ethanol]
1,1-Bis-(2-hydroxy-ethyl)-3-(2-vinyloxy-ethyl)-thiourea
Conditions | Yield |
---|---|
100% |
2,2'-iminobis[ethanol]
phosphonic acid diethyl ester
bis-(2-hydroxy-ethyl)-amidophosphoric acid diethyl ester
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
2,2'-iminobis[ethanol]
cyclohexanecarbaldehyde
2-(2-cyclohexyl-oxazolidin-3-yl)-ethanol
Conditions | Yield |
---|---|
With 1-Methylpyrrolidine; water; 3>PF6 at 140℃; under 51714.8 Torr; for 6h; | 100% |
3-chloro-4-fluoronitrobenzene
2,2'-iminobis[ethanol]
2-[(2-Chloro-4-nitro-phenyl)-(2-hydroxy-ethyl)-amino]-ethanol
Conditions | Yield |
---|---|
at 130℃; for 2h; | 100% |
In dimethyl sulfoxide | 64% |
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]
tert-butylchlorodiphenylsilane
N,N-[bis(2-tert-butyldiphenylsilyloxyethyl)]amine
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]
(4R,5R)-2-thioxo-4,5-bis(tert-butyloxycarbonyl)-1,3-dioxolane
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 0.5h; | 100% |
Conditions | Yield |
---|---|
at 50℃; Michael addition; | 100% |
Conditions | Yield |
---|---|
at 50℃; Michael addition; | 100% |
[4-(4-Benzyloxycarbonylaminobutyl)phenoxy]acetic acid ethyl ester
2,2'-iminobis[ethanol]
[4-(4-{[N,N-bis-(2-hydroxyethyl)carbamoyl]methoxy}phenyl)butyl]carbamic acid benzyl ester
Conditions | Yield |
---|---|
With ethanol at 70℃; for 72h; | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran; methanol for 1h; | 100% |
2,2'-iminobis[ethanol]
hexadecanyl bromide
2,2'-(hexadecylazanediyl)diethanol
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
2,2'-iminobis[ethanol]
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
Conditions | Yield |
---|---|
In water; acetonitrile at 20℃; | 100% |
(2′Z-3′E)-6-bromoindirubin-3′-[O-(2-bromoethyl)oxime]
2,2'-iminobis[ethanol]
(2'Z-3'E)-6-bromoindirubin-3'-[O-(2-(N,N-(2-hydroxyethyl)amino)ethyl)oxime]
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
2,2'-iminobis[ethanol]
2-(4-methoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,6,2-dioxazaborocane
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
2,2'-iminobis[ethanol]
2-(4-ethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,6,2-dioxazaborocane
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
2,2'-iminobis[ethanol]
2-(4-propoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,6,2-dioxazaborocane
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
2,2'-iminobis[ethanol]
2-(4-butoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,6,2-dioxazaborocane
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
2,2'-iminobis[ethanol]
2-(4-pentyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,6,2-dioxazaborocane
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
2,2'-iminobis[ethanol]
2-(4-hexyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-1,3,6,2-dioxazaborocane
Conditions | Yield |
---|---|
In tetrahydrofuran at 25℃; for 1h; Inert atmosphere; | 100% |
C28H20ClN5O5S2
2,2'-iminobis[ethanol]
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
Conditions | Yield |
---|---|
In 1,4-dioxane; water at 20℃; | 100% |
Ixazomib
2,2'-iminobis[ethanol]
Conditions | Yield |
---|---|
In ethyl acetate at 20℃; for 2h; Product distribution / selectivity; | 100% |
2,2'-iminobis[ethanol]
Conditions | Yield |
---|---|
at 105℃; | 100% |
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)
As surfactant and corrosion inhibitor, Diethanolamine (CAS No.111-42-2) is used to remove hydrogen sulfide and carbon dioxide from natural gas.
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.
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. |
Community Right-To-Know List. Reported in EPA TSCA Inventory.
Safety Information of Diethanolamine (CAS No.111-42-2):
Hazard Codes: Xn
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)
OSHA PEL: TWA 3 ppm
ACGIH TLV: TWA 0.46 ppm (skin)
For occupational chemical analysis use NIOSH: Aminoethanol Compounds II 3509.
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.
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