28768-32-3

Basic information

• Product Name: 4,4'-Methylenebis(N,N-diglycidylaniline)
• Synonyms: 4,4'-METHYLENEBIS(N,N-DIGLYCIDYLANILINE);4,4’-Methylenebis(diglycidylaniline);n,n’-(methylenedi-4,1-phenylene)bis[n-(oxiranylmethyl)-oxiranemethanamin;N,N’-(methylenedi-4,1-phenylene)bis[N-(oxiranylmethyl)-Oxiranemethanamine;tetraglycidyl-4,4’-methylenedianiline;4,4'-methylenebis[N,N-bis(2,3-epoxypropyl)aniline];Oxiranemethanamine, N,N-(methylenedi-4,1-phenylene)bisN-(oxiranylmethyl)-;4,4′-Methylenbis(N,N-bis(2,3-epoxypropyl)anilin)
• CAS NO: 28768-32-3
• Molecular Formula: C₂₅H₃₀N₂O₄
• Molecular Weight: 422.52
• EINECS: 249-204-3
• Product Categories: Organics;Epoxide Monomers;Monomers;Polymer Science
• Mol File: 28768-32-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 619.3 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: /
• Density: 1.15 g/mL at 25 °C(lit.)
• Vapor Pressure: 0Pa at 24.85℃
• Refractive Index: n20/D 1.601(lit.)
• PKA: 4.58±0.50(Predicted)
• Water Solubility: 9.2mg/L at 20℃
• CAS DataBase Reference: 4,4'-Methylenebis(N,N-diglycidylaniline)(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Methylenebis(N,N-diglycidylaniline)(28768-32-3)
• EPA Substance Registry System: 4,4'-Methylenebis(N,N-diglycidylaniline)(28768-32-3)

Safety Data

• Hazard Codes: Xi,N
• Statements: 43-51/53
• Safety Statements: 36/37-61
• RIDADR: UN 3082 9 / PGIII
• WGK Germany: 2
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 28768-32-3(Hazardous Substances Data)

Usage

Chemical Properties

Yellow sticky liquid

Synthetic route

C25H34Cl4N2O4 → N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane (28768-32-3)

Conditions	Yield
With sodium hydroxide In water at 50℃; for 1.5h; Temperature;	96%
With sodium hydroxide at 45℃; under 760.051 Torr; for 2.5h; Temperature;	91%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water at 30℃; for 2h; Flow reactor;	88.4%

4,4'-diamino diphenyl methane (101-77-9) + epichlorohydrin (106-89-8) → N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane (28768-32-3)

Conditions	Yield
Stage #1: 4,4'-diamino diphenyl methane; epichlorohydrin With lanthanum nitrate In toluene at 60 - 85℃; under 150.015 - 300.03 Torr; Stage #2: With benzyltrimethylammonium chloride; sodium hydroxide In water; toluene at 60 - 70℃; under 150.015 - 375.038 Torr; Pressure; Reagent/catalyst;	91%

4,4'-diamino diphenyl methane (101-77-9) → N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane (28768-32-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid / 80 °C / Flow reactor 2: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / water / 2 h / 30 °C / Flow reactor View Scheme

piperazine (110-85-0) + N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane (28768-32-3) → 4,4'-methylene-bis(N,N-di-2-hydroxypropyl-3-piperazinylaniline)

Conditions	Yield
In methanol; diethylene glycol dimethyl ether at 60℃; for 65h;	94%

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane (28768-32-3) + Diethyl iminodiacetate (6290-05-7) → C57H90N6O20

Conditions	Yield
In methanol; dichloromethane at 20 - 40℃; for 130.5h;	78%

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane (28768-32-3) + N-methylaniline (100-61-8) → C53H66N6O4

Conditions	Yield
at 110℃; for 24h; Inert atmosphere;	52%

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane (28768-32-3) + 1,1'-(methylenedi-4,1-phenylene)bismaleimide (13676-54-5) + dapsone (80-08-0) → polymer; monomer(s): N,N,N\,,N\-tetraglycidyl-4,4\-diaminodiphenylmethane; 4,4\-diaminodiphenyl sulfone; 4,4\-bis(maleimido)diphenylmethane

Conditions	Yield
Stage #1: N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane; 1,1'-(methylenedi-4,1-phenylene)bismaleimide; dapsone at 140℃; for 16h; Stage #2: at 200℃; for 4h;

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane (28768-32-3) + dapsone (80-08-0) → polymer; monomer(s): N,N,N\,,N\-tetraglycidyl-4,4\-diaminodiphenylmethane; 4,4\-diaminodiphenyl sulfone

Conditions	Yield
Stage #1: N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane; dapsone at 140℃; for 16h; Stage #2: at 200℃; for 4h;

styrene (292638-84-7) + N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane (28768-32-3) → polymer, Mw/Mn = 1.27; monomer(s): styrene; 4,4\-methylene-bis(N,N\-diglycidylaniline)

Conditions	Yield
With bis(cyclopentadienyl)titanium (III) chloride In 1,4-dioxane at 90℃; Kinetics;
With bis(cyclopentadienyl)titanium (III) chloride In 1,4-dioxane at 90℃;

styrene (292638-84-7) + N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane (28768-32-3) → polymer, Mn,GPC = 7496, Mw/Mn = 1.09; monomer(s): styrene; 4,4\-methylene-bis(N,N\-diglycidylaniline)

Conditions	Yield
With bis(cyclopentadienyl)titanium (III) chloride In 1,4-dioxane at 90℃; for 7h;

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane (28768-32-3) + 2-amino-2-hydroxymethyl-1,3-propanediol (77-86-1) → C29H41N3O7 + C33H52N4O10 + C37H63N5O13 + C41H74N6O16

Conditions	Yield
In methanol; dichloromethane at 40 - 60℃; for 72h; Product distribution / selectivity;

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane (28768-32-3) + 2,2'-iminobis[ethanol] (111-42-2) → C37H63N5O10 + C41H74N6O12

Conditions	Yield
In methanol at 20 - 60℃; for 48h;

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane (28768-32-3) + Diethyl iminodiacetate (6290-05-7) → C33H45N3O8 + C41H60N4O12

Conditions	Yield
In methanol; dichloromethane at 20℃; for 48.5h;

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane (28768-32-3) + C37H42N4O6S (103443-52-3) → C62H72N6O10S

Conditions	Yield
Activation energy; Heating;

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane (28768-32-3) + dapsone (80-08-0) → C37H42N4O6S (103443-52-3)

Conditions	Yield
Activation energy; Heating;

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane (28768-32-3) + dapsone (80-08-0) → C62H72N6O10S

Conditions	Yield
Multi-step reaction with 2 steps 1: Heating 2: Heating View Scheme

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane (28768-32-3) + allyl alcohol (107-18-6) → C31H42N2O6

Conditions	Yield
With tetraethylammonium bromide; sodium hydroxide In tetrahydrofuran; acetonitrile at 20℃; for 6h;

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane (28768-32-3) → C51H84N4O14Si2

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; tetraethylammonium bromide / acetonitrile; tetrahydrofuran / 6 h / 20 °C 2: N-ethyl-N,N-diisopropylamine / acetonitrile / 30 h / 65 °C View Scheme

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane (28768-32-3) → C43H74N2O12Si2

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; tetraethylammonium bromide / acetonitrile; tetrahydrofuran / 6 h / 20 °C 2: platinum(IV) oxide / toluene / 24 h / 80 °C View Scheme

N,N,Ν',N'-tetraglycidyl-4,4'-diaminodiphenylmethane (28768-32-3) + ethanol (64-17-5) → C29H42N2O6

Conditions	Yield
With tetraethylammonium bromide; sodium hydroxide In tetrahydrofuran; acetonitrile at 26℃; for 2.5h;

Upstream product

• 101-77-9 4,4'-diamino diphenyl methane 
• 87017-81-0 C₂₅H₃₄Cl₄N₂O₄ 
• 106-89-8 epichlorohydrin 

Downstream Products

• 103443-52-3 C₃₇H₄₂N₄O₆S 

Relevant articles and documents

MANUFACTURING METHOD FOR COMPOUND HAVING N,N-BIS(2-HYROXY-3-CHLOROPROPYL)AMINO GROUP

A method efficiently and safely manufactures, on an industrial scale, a compound having an N,N-bis(2-hydroxy-3-chloropropyl)amino group. (1) an amine compound or a solution thereof, (2) epichlorohydrin or a solution thereof, and (3) an acidic compound or a solution thereof are continuously supplied to a flow reactor and reacted at a reaction temperature of 40 to 130° C. and a liquid space velocity of 0.2 to 10 h?1 so that a compound having an N,N-bis(2-hydroxy-3-chloropropyl)amino group is manufactured. The obtained compound having an N,N-bis(2-hydroxy-3-chloropropyl)amino group is dehydrochlorinated by reaction with an alkali so that a polyfunctional glycidylamine type epoxy compound is manufactured.