6425-39-4

Basic information

• Product Name: 2,2-Dimorpholinodiethylether
• Synonyms: 4,4’-(oxydi-2,1-ethanediyl)bis-morpholin;Dimorpholinodiethylether;BIS(2-MORPHOLINOETHYL) ETHER;BIS[2-(N-MORPHOLINO)ETHYL] ETHER;LUPRAGEN(R) N 106;4,4'-(3-OXAPENTANE-1,5-DIYL)BISMORPHOLINE;4,4-(OXYDI-2,1-ETHANEDIYL)BISMORPHOLINE;2,2'-DIMORPHOLINODIETHYL ETHER
• CAS NO: 6425-39-4
• Molecular Formula: C₁₂H₂₄N₂O₃
• Molecular Weight: 244.33
• EINECS: 229-194-7
• Product Categories: Organics;Polymer Additives;Polymer Science;Polymerization and Polymer Property Modifiers
• Mol File: 6425-39-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: -28 °C
• Boiling Point: 309 °C(lit.)
• Flash Point: 295 °F
• Appearance: STRAW YELLOW
• Density: 1.06 g/mL at 25 °C(lit.)
• Vapor Pressure: 66Pa at 20℃
• Refractive Index: n20/D 1.484(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 6.92±0.10(Predicted)
• Water Solubility: 100g/L at 20℃
• CAS DataBase Reference: 2,2-Dimorpholinodiethylether(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-Dimorpholinodiethylether(6425-39-4)
• EPA Substance Registry System: 2,2-Dimorpholinodiethylether(6425-39-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-36
• WGK Germany: 1
• Hazardous Substances Data: 6425-39-4(Hazardous Substances Data)

Usage

Uses

Catalyst for flexible polyester foams, molded foams, and moisture-cured foams and coatings. Good blowing catalyst that does not cause cross-linking.

General Description

4,4′-(Oxydi-2,1-ethanediyl)bismorpholine (DMDEE) is an amine based catalyst that is also known as dimorpholino-diethyl ether. It can act as a catalyst for blowing reactions and facilitates the process of polymeric curing.

Flammability and Explosibility

Notclassified

Synthetic route

N-(2-chlorethyl)morpholine (3240-94-6) + 2-(morpholin-4-yl)ethanol (622-40-2) → 2,2'-dimorpholinodiethyl ether (6425-39-4)

Conditions	Yield
With sodium hydroxide; adogen 464 In tetrahydrofuran for 6h; Heating;	84%
With sodium

triethanolamine hydrochloride (637-39-8) → morpholine (110-91-8) + 2-(morpholin-4-yl)ethanol (622-40-2) + 1,2-dimorpholylethane (1723-94-0) + 2,2'-dimorpholinodiethyl ether (6425-39-4)

Conditions	Yield
at 190 - 230℃;

triethanolamine hydrochloride (637-39-8) → 2,2'-dimorpholinodiethyl ether (6425-39-4)

Conditions	Yield
at 200 - 230℃;

N-(2-chlorethyl)morpholine (3240-94-6) + 4-(2-hydroxypropyl)morpholine (2109-66-2) → 2,2'-dimorpholinodiethyl ether (6425-39-4) + alpha-methyl-bis<2(4-morpholino)ethyl> ether + beta-methyl bis<2(4-morpholino)ethyl> ether

Conditions	Yield
With sodium hydroxide; adogen 464 In tetrahydrofuran for 6h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

2-(morpholin-4-yl)ethanol (622-40-2) → 2,2'-dimorpholinodiethyl ether (6425-39-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 / 2 h / Heating 2: 50percent NaOH / Adogen 464 / tetrahydrofuran / 6 h / Heating View Scheme
Multi-step reaction with 2 steps 1: SOCl2 / 2 h / Heating 2: 84 percent / 50percent NaOH / Adogen 464 / tetrahydrofuran / 6 h / Heating View Scheme
With sulfuric acid at 130 - 200℃; for 15h;

ammonia (7664-41-7) + diethylene glycol (111-46-6) → 2,2'-dimorpholinodiethyl ether (6425-39-4)

Conditions	Yield
With hydrogen; γ-Al2O3 (45 weight %), CuO (55 weight %), hydrogenated at 210℃; under 12001.2 Torr; Product distribution / selectivity;

triethanolamine (102-71-6) → 2,2'-dimorpholinodiethyl ether (6425-39-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / 15 h / 130 - 200 °C 2: sulfuric acid / 15 h / 130 - 200 °C View Scheme

triethanolamine (102-71-6) → 2-(morpholin-4-yl)ethanol (622-40-2) + 2,2'-dimorpholinodiethyl ether (6425-39-4)

Conditions	Yield
With sulfuric acid at 130 - 200℃; for 15h; Temperature; Time;

2,2'-dimorpholinodiethyl ether (6425-39-4) + pentafluorophenyl ester of quinaldic acid (148315-27-9) → morpholino(quinolin-2-yl)methanone (78224-46-1)

Conditions	Yield
With palladium diacetate In chlorobenzene at 115℃; for 24h;	69%

2,2'-dimorpholinodiethyl ether (6425-39-4) → C12F24N2O3 (108709-76-8)

Conditions	Yield
With hydrogen fluoride In water at 50℃; under 1551.4 Torr; for 233h; average voltage of electrochemical cell = 5.8 volts; 20 amps;	44%

Upstream product

• 7664-41-7 ammonia 
• 111-46-6 diethylene glycol 
• 102-71-6 triethanolamine 
• 622-40-2 2-(morpholin-4-yl)ethanol 
• 3240-94-6 N-(2-chlorethyl)morpholine 
• 2109-66-2 4-(2-hydroxypropyl)morpholine 
• 637-39-8 triethanolamine hydrochloride 

Relevant articles and documents

Production method of DMDEE

The invention discloses a production method of DMDEE. The production method comprises the following steps: dropwise adding TEOA to sulfuric acid to form a synthesis reaction system, heating to the temperature of 160 to 250 DEG C after dropwise adding and carrying out heat preservation for 3 to 24 h, and discharging water in the synthesis reaction process out of the synthesis reaction system to realize dehydration; adding water, a solvent and an alkali substance to carry out a neutralization reaction after cooling an obtained reaction solution and ending the neutralization reaction until the pHvalue is 8 to 14; filtering a product obtained by the neutralization reaction, and carrying out distillation separation on filtrate obtained by filtering to obtain DMDEE. DMDEE prepared by the methodhas the technical advantages of simple process, low cost and less pollution.

Amine bisulfites

This invention relates to the amine bisulfites which are useful as a combination corrosion inhibitor/oxygen scavenger. This is illustrated by heterocyclic amine bisulfites such as pyridine bisulfites.