3033-62-3

Basic information

• Product Name: Bis(2-dimethylaminoethyl) ether
• Synonyms: 2,2’-oxybis[n,n-dimethyl-ethanamin;2,2’-oxybis[N,N-dimethyl-Ethanamine;A 99;A 99 (Amine);a99(amine);dabcobl11;dabcobl19;dabcobl19i
• CAS NO: 3033-62-3
• Molecular Formula: C₈H₂₀N₂O
• Molecular Weight: 160.26
• EINECS: 221-220-5
• Mol File: 3033-62-3.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 189 °C 760 mm Hg
• Flash Point: 151 °F
• Appearance: A clear or yellow liquid
• Density: 0.841 g/mL at 25 °C
• Vapor Pressure: 49Pa at 20℃
• Refractive Index: n 20/D 1.430
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Soluble in water
• PKA: 9.12±0.28(Predicted)
• Water Solubility: 100g/L at 20℃
• BRN: 1739668
• CAS DataBase Reference: Bis(2-dimethylaminoethyl) ether(CAS DataBase Reference)
• NIST Chemistry Reference: Bis(2-dimethylaminoethyl) ether(3033-62-3)
• EPA Substance Registry System: Bis(2-dimethylaminoethyl) ether(3033-62-3)

Safety Data

• Hazard Codes: T
• Statements: 20-22-24-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2927 6.1/PG 2
• WGK Germany: 2
• RTECS: KR9460000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 3033-62-3(Hazardous Substances Data)

Usage

Chemical Properties

Colorless and transparent liquid or Brown liquid. Soluble in water, easily soluble in alcohol, benzene, etc.

Uses

Bis(2-dimethylaminoethyl) ether is an efficient tertiary amine catalyst, which is suitable for the production of almost all foam products, mainly for the production of flexible foam products, especially for high resilience and RIM products. It is characterized by high catalytic activity, smooth foaming, large tolerance to tin, easy to adjust the formulation, and the physical and chemical properties of products produced with it, such as resilience and elongation, are better than other products.

Preparation

The main methods for the synthesis of Bis(2-dimethylaminoethyl) ether are:(1) reaction of sodium dimethylaminoethanol and SO3 or chlorosulfonic acid;(2) Reaction of trimethylamine with dichloroethyl ether or dimethylaminoethoxyethyl ether;(3) One-step synthesis of dimethylamine and monoethyleneglycol under solid catalyst.

Application

Bis(2-dimethylaminoethyl) Ether (Potassium Clavulanate EP Impurity M) is used in the manufacturing of flexible polyurethane foams.

General Description

Bis(2-(dimethylamino)ethyl)ether appears as a clear or yellow liquid. Bp: 188°C. Toxic by inhalation, by skin absorption, ingestion, and eye contact.

Reactivity Profile

Bis (2-(dimethylamino)ethyl)ether reacts as a base. Reacts exothermically with acids. May form explosive peroxides upon exposure to the air.

Safety Profile

Poison by skin contact.Moderately toxic by ingestion. Experimental reproductiveeffects. A severe skin and eye irritant.

Synthetic route

2-(N,N-dimethylamino)ethanol (108-01-0) + dimethyl amine (124-40-3) + acetylene (74-86-2) → Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3)

Conditions	Yield
With potassium hydroxide In dibutyl ether at 100℃; for 5h;	90.4%

2-(N,N-dimethylamino)ethanol (108-01-0) → Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3)

Conditions	Yield
In water at 175 - 180℃; for 3h; Temperature; Time;	78.5%
With 4-methyl-morpholine; ammonium tungstate at 145 - 155℃; for 15h; Reagent/catalyst; Autoclave; Inert atmosphere; Sealed tube;	73.6%
With sulfuric acid at 190℃; for 12h; Temperature; Reagent/catalyst;	65%

2-(N,N-dimethylamino)ethanol (108-01-0) + N-Methyldiethanolamine (105-59-9) → 2-((2-(2-(dimethylamino)ethoxy)ethyl)methyl-amino)-ethanol + Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3)

Conditions	Yield
With 4-methyl-morpholine; silica-alumina at 145 - 155℃; for 15h; Catalytic behavior; Reagent/catalyst; Time; Concentration; Temperature; Autoclave; Inert atmosphere; Sealed tube; Overall yield = 95.6 %;	A 76.4% B 75 g

1-O-Dimethylaminoethyl-ethylenglykol (1704-62-7) + dimethyl amine (124-40-3) → Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3)

Conditions	Yield
With hydrogen at 220℃; under 15001.5 - 142514 Torr; for 8h; Temperature; Pressure;	74.63%
With hydrogen at 200℃; under 5931.67 Torr; Product distribution / selectivity;	47 %Chromat.

2-(N,N-dimethylamino)ethanol (108-01-0) + 2-(dimethylamino)ethyl chloride (107-99-3) → Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3)

Conditions	Yield
With sodium hydroxide; adogen 464 In tetrahydrofuran for 6h; Heating;	35%

dimethyl amine (124-40-3) + 3-oxa-1,5-dichloropentane (111-44-4) + benzene (71-43-2) → 4-methyl-morpholine (109-02-4) + Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3)

Conditions	Yield
at 140℃;

dimethyl amine (124-40-3) + 3-oxa-1,5-dichloropentane (111-44-4) → Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3)

Conditions	Yield
With ethanol at 120℃;
With benzene at 140℃;

sodium N,N-dimethylethanolamine (37616-36-7) + 2-(dimethylamino)ethyl chloride (107-99-3) → Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3)

Conditions	Yield
With toluene

2-(dimethylamino)ethyl chloride (107-99-3) + benzene (71-43-2) + sodium-compound of acetamide → 2-(N,N-dimethylamino)ethanol (108-01-0) + Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3) + 2-(dimethylamino)ethyl acetate (1421-89-2) + N-<2-(dimethylamino)ethyl>acetamide (3197-11-3)

Conditions	Yield
Produkt5: 1,2-Bis-dimethylamino-aethan;

1-O-Dimethylaminoethyl-ethylenglykol (1704-62-7) + methylamine (74-89-5) → 4-methyl-morpholine (109-02-4) + N,N,N'-trimethylbis(aminoethyl)ether (93240-93-8) + Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3)

Conditions	Yield
With hydrogen at 195℃; under 11879 Torr; for 23.3h; Product distribution / selectivity; Compressed gas(es);	A 3.1 %Chromat. B 44.3 %Chromat. C 1.6 %Chromat.
With hydrogen; potassium nitrate at 200℃; under 4395.7 Torr; Product distribution / selectivity;
With hydrogen at 200℃; under 4369.84 Torr; Product distribution / selectivity;

dimethyl amine (124-40-3) + diethylene glycol (111-46-6) → 1-O-Dimethylaminoethyl-ethylenglykol (1704-62-7) + Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3)

Conditions	Yield
With hydrogen; γ-Al2O3 (45 weight %), CuO (55 weight %), hydrogenated at 190℃; under 15001.5 Torr; Product distribution / selectivity;
Stage #1: diethylene glycol With C39H57ClNP2Rh In 5,5-dimethyl-1,3-cyclohexadiene; ethanol at -78℃; for 0.5h; Autoclave; Inert atmosphere; Stage #2: dimethyl amine In 5,5-dimethyl-1,3-cyclohexadiene; ethanol at 150℃; under 112511 Torr; for 120h; Solvent; Reagent/catalyst; Pressure; Autoclave; Inert atmosphere;

1-O-Dimethylaminoethyl-ethylenglykol (1704-62-7) → morpholine (110-91-8) + 4-methyl-morpholine (109-02-4) + N,N,N'-trimethylbis(aminoethyl)ether (93240-93-8) + 2-(2-aminoethoxy)-N,N-dimethylethanamine (85322-63-0) + Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3) + bis-(2-(N,N-dimethylamino)ethoxyethyl)methylamine (65286-55-7) + [2-(2-amino-ethoxy)-ethyl]-[2-(2-dimethylamino-ethoxy)-ethyl]-methyl-amine (1257084-24-4) + bis-(2-(N,N-dimethylamino)ethoxyethyl)amine (1257084-22-2) + [2-(2-dimethylamino-ethoxy)-ethyl]-[2-(2-methylamino-ethoxy)-ethyl]-amine (1257084-23-3)

Conditions	Yield
With ammonia; copper chromite at 200℃; under 52505.3 Torr; Product distribution / selectivity; Industry scale;

...Expand

dimethyl amine (124-40-3) + diethylene glycol (111-46-6) → Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3)

Conditions	Yield
With hydrogen; shaped bodies of reduced CuO/γ-Al2O3 (55 wt%/45 wt%) at 210℃; under 15001.5 Torr; Product distribution / selectivity;

1-O-Dimethylaminoethyl-ethylenglykol (1704-62-7) + methylamine (74-89-5) → N,N,N'-trimethylbis(aminoethyl)ether (93240-93-8) + Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3)

Conditions	Yield
With copper chromite at 166℃; under 7500.75 Torr; for 513h;	A 26.81 %Chromat. B 19.37 %Chromat.

1-O-Dimethylaminoethyl-ethylenglykol (1704-62-7) + trimethylamine (75-50-3) → Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3)

Conditions	Yield
Stage #1: 1-O-Dimethylaminoethyl-ethylenglykol With thionyl chloride In toluene for 1.5h; Reflux; Stage #2: trimethylamine at 50 - 80℃; for 3h; Stage #3: With ethylenediamine at 100 - 170℃; for 3h; Temperature; Autoclave;	132 g

1-O-Dimethylaminoethyl-ethylenglykol (1704-62-7) + dimethyl amine (124-40-3) → 4-methyl-morpholine (109-02-4) + Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3)

Conditions	Yield
With hydrogen at 230℃; under 11400.8 Torr; Temperature; Pressure; Reagent/catalyst;

2,2'-diiodoethyl ether (34270-90-1) + Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3) → N,N,N',N'-tetramethyl-1,7-diaza-4,10-dioxacyclododecane di-iodide

Conditions	Yield
In acetonitrile under 7500600 Torr; for 48h; Mechanism; Quantum yield; Ambient temperature; further substrates and reactants;	99%
In acetonitrile under 7500600 Torr; for 48h; Ambient temperature;	99%
In acetonitrile at 25℃; under 8250660 Torr; for 20h;	99%

Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3) + 1,2-bis-(2-iodoethoxy)benzene (110431-62-4) → N,N,N',N'-tetramethyl-5,6-benzo-1,10-diaza-4,7,13-trioxacyclopentadecane di-iodide

Conditions	Yield
In acetonitrile under 7500600 Torr; for 48h; Ambient temperature;	96%
In acetonitrile at 25℃; under 8250660 Torr; for 20h;	96%

Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3) + 1,2-bis-(2-iodoethoxy)ethane (36839-55-1) → N,N,N',N'-tetramethyl-1,10-diaza-4,7,13-trioxacyclopentadecane di-iodide

Conditions	Yield
In acetonitrile under 7500600 Torr; for 48h; Ambient temperature;	95%
In acetonitrile at 25℃; under 8250660 Torr; for 20h;	95%

Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3) + 1-dodecylbromide (143-15-7) → 2,2'-bis(dodecyldimethylammonium)diethyl ether dibromide

Conditions	Yield
In water; acetonitrile at 80℃; for 55h; Solvent;	95%

Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3) + 1-(bromomethyl)-4-(dodecyloxy)benzene (123436-89-5) → bis{2-N,N-dimethyl-N-[p-(n-dodecyloxybenzyl)]ammonium} bromide ethyl ether

Conditions	Yield
In acetonitrile for 1h; Reflux;	94%

2-Bromoethyl ethyl ether (592-55-2) + Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3) → 2,2'-oxybis(N-(2-ethoxyethyl)-N,N-dimethylethanammonium) bromide

Conditions	Yield
In acetone for 24h; Cooling with ice; Reflux;	88%

1-bromo dodecane (112-29-8) + Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3) → bis(N-decyl-N,N-dimethylethylammonium)ether dibromide

Conditions	Yield
In acetonitrile at 80℃; for 55h;	83%

Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3) + potassium hexamethylsilazane (40949-94-8) → C40H112K4N8O2Si8

Conditions	Yield
In hexane Inert atmosphere; Schlenk technique;	66%

Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3) + potassium hexamethylsilazane (40949-94-8) → C22H58KN5O2Si2

Conditions	Yield
In hexane Inert atmosphere; Schlenk technique;	62%

Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3) + 2-tert-butyl-4,5-di-(1,1-dimethylpropyl) imidazole (1279010-11-5) + bis(tetrahydrofuran)strontium di(bis(trimethylsilyl)amide) (133766-06-0) → bis(2-tert-butyl-4,5-di-tert-amylimidazolyl)(2,2'-oxybis(N,N-dimethylethylamine))strontium (1279016-87-3)

Conditions	Yield
In hexane at 20℃; Inert atmosphere;	43%

2,2,6,6-tetramethyl-piperidine (768-66-1) + n-butyllithium (109-72-8, 29786-93-4) + Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3) + diisobutylaluminum chloride (1779-25-5) → [Li(μ-2,2,6,6-tetramethylpiperidide)(μ-bis[2-(N,N-dimethylamino)ethyl]ether)Al(isobutyl)2]

Conditions	Yield
Stage #1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium In hexane at 20℃; for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: diisobutylaluminum chloride In hexane for 1h; Inert atmosphere; Schlenk technique; Stage #3: Bis<2-(N,N-dimethylamino)aethyl>aether In hexane Inert atmosphere; Schlenk technique;	42%

Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3) + epichlorohydrin (106-89-8) → N,N′-(oxybis(ethane-2,1-diyl))bis(3-chloro-2-hydroxy-N,N-dimethylpropan-1-aminium) chloride

Conditions	Yield
With hydrogenchloride In water at 25 - 70℃; for 6h; pH=< 2 - 8.5;	39.4%

di(pyridin-2-yl)amine (1202-34-2) + Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3) → [(N,N,N′,N′-tetramethyldiaminoethylether)Na(2,2′-dipyridylamide)]2

Conditions	Yield
Stage #1: di(pyridin-2-yl)amine With butylsodium In hexane for 1h; Inert atmosphere; Schlenk technique; Stage #2: Bis<2-(N,N-dimethylamino)aethyl>aether In hexane at -30℃; for 48h; Inert atmosphere; Schlenk technique;	37%

Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3) + butylsodium (3525-44-8) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) + sodium iodide (7681-82-5) → C30H90IN5Na5Si10(1-)*C16H40N4NaO2(1+)

Conditions	Yield
Stage #1: butylsodium; 1,1,1,3,3,3-hexamethyl-disilazane In hexane for 2h; Inert atmosphere; Schlenk technique; Stage #2: sodium iodide In hexane for 24h; Inert atmosphere; Schlenk technique; Stage #3: Bis<2-(N,N-dimethylamino)aethyl>aether In hexane for 15h; Inert atmosphere; Schlenk technique;	36%

Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3) + 1-lithio-2-tert-butyl-1,2-dihydropyridine → C17H34LiN3O

Conditions	Yield
In tetrahydrofuran; hexane at -30℃; for 168h; Inert atmosphere;	32%

ethyl bromide (74-96-4) + Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3) → N,N'-diethyl-N,N,N',N'-tetramethyl-N,N'-(3-oxa-pentanediyl)-di-ammonium; dibromide (64049-67-8)

Conditions	Yield
With acetone

Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3) + benzyl chloride (100-44-7) → N,N'-dibenzyl-N,N,N',N'-tetramethyl-N,N'-(3-oxa-pentanediyl)-di-ammonium; dichloride (63722-05-4)

Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3) + ethyl iodide (75-03-6) → N,N'-diethyl-N,N,N',N'-tetramethyl-N,N'-(3-oxa-pentanediyl)-di-ammonium; diiodide

Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3) + chloroacetic acid ethyl ester (105-39-5) → N,N'-bis-ethoxycarbonylmethyl-N,N,N',N'-tetramethyl-N,N'-(3-oxa-pentanediyl)-di-ammonium; dichloride

Conditions	Yield
With acetone
In isopropyl alcohol for 8h; Reflux;

Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3) + methyl iodide (74-88-4) → hexa-N-methyl-N,N'-(3-oxa-pentanediyl)-di-ammonium; diiodide (2576-43-4)

Conditions	Yield
With ethanol

Bis<2-(N,N-dimethylamino)aethyl>aether (3033-62-3) → F-bis[2-(N,N-dimethylamino)ethyl] ether

Conditions	Yield
With hydrogen fluoride In water electrochemical fluorination; Yield given;

Upstream product

• 37616-36-7 sodium N,N-dimethylethanolamine 
• 107-99-3 2-(dimethylamino)ethyl chloride 
• 71-43-2 benzene 
• 1704-62-7 1-O-Dimethylaminoethyl-ethylenglykol 
• 74-89-5 methylamine 
• 124-40-3 dimethyl amine 
• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 74-86-2 acetylene 
• 111-46-6 diethylene glycol 
• 111-44-4 3-oxa-1,5-dichloropentane 
• 75-50-3 trimethylamine 
• 105-59-9 N-Methyldiethanolamine 

Downstream Products

• 50-00-0 formaldehyd 
• 68-12-2 N,N-dimethyl-formamide 
• 2576-43-4 hexa-N-methyl-N,N'-(3-oxa-pentanediyl)-di-ammonium; diiodide 
• 63722-05-4 N,N'-dibenzyl-N,N,N',N'-tetramethyl-N,N'-(3-oxa-pentanediyl)-di-ammonium; dichloride 

Relevant articles and documents

Selective Synthesis of Bisdimethylamine Derivatives from Diols and an Aqueous Solution of Dimethylamine through Iridium-Catalyzed Borrowing Hydrogen Pathway

Bisdimethylamine derivatives are an important class of compounds in the polymer and pharmaceutical industries. However, existing methods for the synthesis of these compounds have several drawbacks such as low selectivity, use of toxic reagents, and generation of waste. In this study, a new system was developed for the selective synthesis of bisdimethylamine derivatives using a diol and dimethylamine as starting materials and an iridium complex bearing an N-heterocyclic carbene ligand as catalyst. The starting materials were easily available, less toxic, inexpensive, and easy to handle. The reaction proceeded efficiently through a borrowing hydrogen pathway under aqueous conditions, without any additional organic solvent, to afford various bisdimethylamine derivatives in good to excellent yields.

Production method of BDMAEE

The invention discloses a production method of BDMAEE. The production method comprises the following steps: adding sulfuric acid, DMEA and super-strong solid acid taken as a catalyst in a reaction vessel to perform an etherification reaction; adding an extractant to obtained etherification liquid, and introducing ammonia to an extraction system to neutralize while stirring, and stopping introducing ammonia to neutralize until pH is 11-13; filtering an obtained product to achieve solid-liquid separation; washing and drying a solid obtained by filtering to obtain ammonium sulfate; and carrying out distillation on filtrate obtained by filtering to obtain BDMAEE. BDMAEE prepared by the method disclosed by the invention is high in efficiency and product yield, high in purity and less in wastewater, and can realize resource utilization of by-products.

Bis(2-dimethylaminoethyl)ether synthesis method

The invention belongs to the technical field of organic macromolecular compounds and relates to a bis(2-dimethylaminoethyl)ether synthesis method. The method includes subjecting dimethylamine and ethylene oxide to reaction in a high-pressure reactor, wherein a mole ratio is 1:2-2.2, a reaction temperature is 60-100 DEG C, reaction time is 2-5 hours, and curing time is 0.5-1 hour; adding a catalyst Cu-Ni/gamma-Al2O3, adopting hydrogen for adjusting an internal pressure of the reactor to 1.5-2.5 MPa, controlling the temperature at 190-220 DEG C, controlling a reaction pressure to be 10-25 MPa, and reacting for 6-13h; after the pressure drops to 1.0 MPa, feeding to the middle of an amine/hydrogen removal tower to discharge the dimethylamine and the hydrogen in the mixture from the top of the amine/hydrogen removal tower, and subjecting a crude product of bis(2-dimethylaminoethyl)ether at the bottom of the amine/hydrogen removal tower to reduced pressure distillation and separation. The bis(2-dimethylaminoethyl)ether synthesis method is applied to polyether preparation and has advantages of high equipment utilization rate, high preparation efficiency and the like.