3033-77-0

Basic information

• Product Name: 2,3-Epoxypropyltrimethylammonium chloride
• Synonyms: (2,3-epoxypropyl)trimethyl-ammoniuchloride;glycidyltrimethylammonium;glytac;glytaca100;g-mac;n,n,n-trimethyl-oxiranemethanaminiuchloride;n,n,n-trimethyloxiranemethanaminiumchloride;Glycidyltrimethylammonium chloride,(2,3-Epoxypropyl)trimethylammonium chloride
• CAS NO: 3033-77-0
• Molecular Formula: C₆H₁₄NO*Cl
• Molecular Weight: 151.63
• EINECS: 221-221-0
• Mol File: 3033-77-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 137-139 °C
• Flash Point: 170 °C
• Appearance: solid
• Density: 1.13 g/mL at 20 °C(lit.)
• Refractive Index: 1.48
• Storage Temp.: 2-8°C
• Solubility: Methanol (Slightly), Water (Sparingly)
• Water Solubility: 852g/L at 20℃
• Stability: Stable. Incompatible with oxidizing agents
• BRN: 3914931
• CAS DataBase Reference: 2,3-Epoxypropyltrimethylammonium chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Epoxypropyltrimethylammonium chloride(3033-77-0)
• EPA Substance Registry System: 2,3-Epoxypropyltrimethylammonium chloride(3033-77-0)

Safety Data

• Hazard Codes: T
• Statements: 45-21/22-41-43-48/22-68-52/53-20/21/22-60
• Safety Statements: 53-14-26-36/37/39-45-61
• WGK Germany: 3
• RTECS: BQ3480000
• Hazardous Substances Data: 3033-77-0(Hazardous Substances Data)

Usage

Description

Used in the production of cationic starch for the paper industry, 2,3-Epoxypropyl trimethyl ammonium chloride (EPTMAC) caused contact dermatitis in the workers.

Chemical Properties

solid

Uses

Different sources of media describe the Uses of 3033-77-0 differently. You can refer to the following data:
1. Reagent used for synthesis and antimicrobial activity of a water soluble chitosan derivative with a fiber-reactive group.
2. Glycidyltrimethylammonium chloride be used as a derivatizing agent to synthesize N-(2-hydroxypropyl)-3-trimethylammonium chitosan chloride (HTCC), a water-soluble chitosan derivative, by reacting with chitosan. HTCC can form nanocomposite films with silver nanoparticles that show good antimicrobial property and optical transparency. Cationic starches can also be prepared by derivatization of starch with GTMAC.

General Description

Glycidyltrimethylammonium chloride (GTMAC) is a cationizing agent commonly used for starch modification.

Contact allergens

Used in the production of cationic starch for the paper industry; EPTMAC caused contact dermatitis in workers.

Safety Profile

Suspected carcinogen. Poison by subcutaneous route. Mutation data reported. When heated to decomposition it emits toxic fumes of Cl-, NH3, and NOx. See also AMMONIUM CHLORIDE.

InChI:InChI=1/C6H14NO/c1-7(2,3)4-6-5-8-6/h6H,4-5H2,1-3H3/q+1

Synthetic route

epichlorohydrin (106-89-8) + trimethylamine (75-50-3) → glycidyltrimethylammonium chloride (3033-77-0)

Conditions	Yield
With ethanol at 100℃;
at 120℃;
In water at 20℃;
In chloroform; toluene at 20℃; Solvent; Temperature; Autoclave;	405.5 g

N-(3-chloro-2-hydroxypropyl)trimethylammonium chloride → glycidyltrimethylammonium chloride (3033-77-0)

Conditions	Yield
With sodium hydroxide In water at 20℃; for 0.5h;
With sodium hydroxide In water
With sodium hydroxide at 13 - 15℃; for 1.16667h;
With sodium hydroxide

epichlorohydrin (106-89-8) → glycidyltrimethylammonium chloride (3033-77-0)

TREHALOSE (99-20-7) + glycidyltrimethylammonium chloride (3033-77-0) → C24H50N2O13(2+)*2Cl(1-)

Conditions	Yield
With sodium chloride; sodium hydroxide In isopropyl alcohol at 20 - 40℃; for 7h; pH=11;	96%

cobalt(II) molybdate + glycidyltrimethylammonium chloride (3033-77-0) → glycidyltrimethylammonium cobalt(III) molybdate

Conditions	Yield
In water for 0.166667h;	90%

molybdenum vanadate + water (7732-18-5) + glycidyltrimethylammonium chloride (3033-77-0) → penta(glycidyltrimethylammonium)phosphomolybdic vanadate

Conditions	Yield
for 0.166667h;	90%

ammonium molybdate tetrahydrate + glycidyltrimethylammonium chloride (3033-77-0) → glycidyltrimethylammonium pentaammonium molybdate

Conditions	Yield
In water for 0.166667h;	90%

sodium molybdate + glycidyltrimethylammonium chloride (3033-77-0) → penta(glycidyltrimethylammonium) molybdate

Conditions	Yield
In water for 0.166667h;	90%

glycidyltrimethylammonium chloride (3033-77-0) + deacetylated chitosan → N-[(2-hydroxy-3-trimethylammonium)propyl]chitosan chloride

Conditions	Yield
In water for 10h;	87.8%

glycidyltrimethylammonium chloride (3033-77-0) + dimethyl amine (124-40-3) → 3-(dimethylamino)-2-hydroxy-N,N,N-trimethylpropan-1-aminium chloride

Conditions	Yield
In water at 60℃;	87%

C17H6Br2Cl2N4O2 + glycidyltrimethylammonium chloride (3033-77-0) + 1,14-diamino-3,6,9,12-tetraoxatetradecane (68960-97-4) → C33H43Br2ClN7O7(1+)*Cl(1-)

Conditions	Yield
Stage #1: C17H6Br2Cl2N4O2; 1,14-diamino-3,6,9,12-tetraoxatetradecane With sodium carbonate at 35 - 40℃; for 2h; pH=5-6; Stage #2: glycidyltrimethylammonium chloride With hydrogenchloride at 85℃; pH=4;	82.46%

geranic acid (459-80-3) + glycidyltrimethylammonium chloride (3033-77-0) → C16H30NO3(1+)*Cl(1-)

Conditions	Yield
With sodium hydrogencarbonate In isopropyl alcohol; acetone at 80℃; for 16h;	79%

cis-Octadecenoic acid (112-80-1) + glycidyltrimethylammonium chloride (3033-77-0) → (Z)-2-hydroxy-3-[(1-oxo-9-octadecenyl)oxy]propyltrimethylammonium chloride

Conditions	Yield
With sodium hydrogencarbonate In isopropyl alcohol; acetone at 80℃; for 16h;	79%

1-(4,6-dichloro-[1,3,5]triazin-2-ylamino)-anthraquinone (6522-75-4) + glycidyltrimethylammonium chloride (3033-77-0) + 1,14-diamino-3,6,9,12-tetraoxatetradecane (68960-97-4) → C33H45ClN7O7(1+)*Cl(1-)

Conditions	Yield
Stage #1: 1-(4,6-dichloro-[1,3,5]triazin-2-ylamino)-anthraquinone; 1,14-diamino-3,6,9,12-tetraoxatetradecane With sodium carbonate at 35 - 40℃; for 2h; pH=5-6; Stage #2: glycidyltrimethylammonium chloride With hydrogenchloride at 85℃; pH=4;	79%

3-hydroxyethylammonium-n-propanesulfonate (1119-23-9) + glycidyltrimethylammonium chloride (3033-77-0) → N-(2-hydroxy-3-trimethylammoniumpropyl)-N-(2-hydroxyethyl)homotaurine inner salt (1379044-59-3)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol; water at 5 - 20℃; for 21h;	76%

glycidyltrimethylammonium chloride (3033-77-0) + 3-Phenylpropionic acid (501-52-0) → C15H24NO3(1+)*Cl(1-)

Conditions	Yield
With sodium hydrogencarbonate In isopropyl alcohol; acetone at 80℃; for 16h;	76%

2-benzyloxybenzoic acid (14389-86-7) + glycidyltrimethylammonium chloride (3033-77-0) → C20H26NO4(1+)*Cl(1-)

Conditions	Yield
With sodium hydrogencarbonate In isopropyl alcohol; acetone at 80℃; for 16h;	73%

3-methylbutyric acid (503-74-2) + glycidyltrimethylammonium chloride (3033-77-0) → C11H24NO3(1+)*Cl(1-)

Conditions	Yield
With sodium hydrogencarbonate In isopropyl alcohol; acetone at 80℃; for 16h;	70%

glycidyltrimethylammonium chloride (3033-77-0) + cyclomaltooctaose (17465-86-0) → C54H94NO41(1+)*Cl(1-)

Conditions	Yield
With sodium hydroxide In water at 60℃; for 2h;	60%

Cytosine (71-30-7) + glycidyltrimethylammonium chloride (3033-77-0) → [3-(4-Amino-2-oxo-2H-pyrimidin-1-yl)-2-hydroxy-propyl]-trimethyl-ammonium; chloride

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 16h;	57%

glycidyltrimethylammonium chloride (3033-77-0) + heptakis(6-amino-6-deoxy)-β-cyclodextrin (30754-24-6) → heptakis-[6-deoxy-6-(2-hydroxy-3-trimethylammonion-propyl)amino]-beta-cyclomaltoheptaose

Conditions	Yield
In aq. buffer at 50℃; for 24h; pH=10;	51%

guanidine sulfamate (50979-18-5) + glycidyltrimethylammonium chloride (3033-77-0) → C7H19N4O(1+)*Cl(1-)*H3NO3S

Conditions	Yield
With water; 4-pyrrolidin-1-ylpyridine at 45℃; for 2h; Temperature;	50.5%

glycidyltrimethylammonium chloride (3033-77-0) + benzoic acid (65-85-0) → C13H20NO3(1+)*Cl(1-)

Conditions	Yield
With sodium hydrogencarbonate In isopropyl alcohol; acetone at 60℃; for 16h;	26%

glycidyltrimethylammonium chloride (3033-77-0) + hexanoic acid (142-62-1) → C12H26NO3(1+)*Cl(1-)

Conditions	Yield
With sodium hydrogencarbonate In isopropyl alcohol; acetone at 60℃; for 16h;	25%

glycidyltrimethylammonium chloride (3033-77-0) + alpha cyclodextrin (10016-20-3) → C42H74NO31(1+)*Cl(1-)

Conditions	Yield
With sodium hydroxide at 50℃;	23%

bis(2-propyl)-p-toluenesulfonyloxymethylphosphonate (35717-98-7) + glycidyltrimethylammonium chloride (3033-77-0) + adenine (66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9) → 9-(2-(phosphonomethoxy)-3-(trimethylammonio)propyl)adenine

Conditions	Yield
Multistep reaction;

bis(2-propyl)-p-toluenesulfonyloxymethylphosphonate (35717-98-7) + glycidyltrimethylammonium chloride (3033-77-0) + 2,6-diaminopurine (1904-98-9) → 9-(2-(phosphonomethoxy)-3-(trimethylammonio)propyl)-2,6-diaminopurine

Conditions	Yield
Multistep reaction;

methanol (67-56-1) + glycidyltrimethylammonium chloride (3033-77-0) + β‐cyclodextrin (7585-39-9) → [3-((3R,4S,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-2-hydroxy-propyl]-trimethyl-ammonium; chloride + [3-((2R,3R,4S,5R)-3,5-Dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-2-hydroxy-propyl]-trimethyl-ammonium; chloride + [2-Hydroxy-3-((2R,3S,4S,5R)-3,4,5-trihydroxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-propyl]-trimethyl-ammonium; chloride

Conditions	Yield
With sodium hydroxide Product distribution; var. conditions; also degradation of γ-cyclodextrin;

bis(2-propyl)-p-toluenesulfonyloxymethylphosphonate (35717-98-7) + glycidyltrimethylammonium chloride (3033-77-0) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + adenine (66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9) → 9-(2-(phosphonomethoxy)-3-(trimethylammonio)propyl)adenine + 3-[2-(phosphonomethoxy)-3-(trimethylammonio)propyl]adenine

Conditions	Yield
With ammonium hydroxide; trimethylsilyl bromide; sodium hydride; triethylamine Yield given. Multistep reaction;
With ammonium hydroxide; trimethylsilyl bromide; sodium hydride; triethylamine Multistep reaction;

bis(2-propyl)-p-toluenesulfonyloxymethylphosphonate (35717-98-7) + glycidyltrimethylammonium chloride (3033-77-0) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + adenine (66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9) → [3-(6-Amino-purin-9-yl)-2-(diisopropoxy-phosphorylmethoxy)-propyl]-trimethyl-ammonium; chloride + [3-(6-Amino-purin-3-yl)-2-(diisopropoxy-phosphorylmethoxy)-propyl]-trimethyl-ammonium; chloride

Conditions	Yield
With ammonium hydroxide; sodium hydride Multistep reaction. Title compound not separated from byproducts;

bis(2-propyl)-p-toluenesulfonyloxymethylphosphonate (35717-98-7) + glycidyltrimethylammonium chloride (3033-77-0) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + adenine (66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9) → {2-(Diisopropoxy-phosphorylmethoxy)-3-[6-(dimethylamino-methyleneamino)-purin-3-yl]-propyl}-trimethyl-ammonium; chloride + {2-(Diisopropoxy-phosphorylmethoxy)-3-[6-(dimethylamino-methyleneamino)-purin-9-yl]-propyl}-trimethyl-ammonium; chloride

Conditions	Yield
With sodium hydride Multistep reaction. Title compound not separated from byproducts;

glycidyltrimethylammonium chloride (3033-77-0) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + adenine (66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9) → {3-[6-(Dimethylamino-methyleneamino)-purin-9-yl]-2-hydroxy-propyl}-trimethyl-ammonium; chloride + {3-[6-(Dimethylamino-methyleneamino)-purin-3-yl]-2-hydroxy-propyl}-trimethyl-ammonium; chloride

Conditions	Yield
With 1.) CsCO3 1.) DMF, 120 deg C, 16 h, 2.) DMF, 20 deg C, 24 h; Multistep reaction. Title compound not separated from byproducts;

Upstream product

• 106-89-8 epichlorohydrin 
• 75-50-3 trimethylamine 
• 101396-91-2 N-(3-chloro-2-hydroxypropyl)trimethylammonium chloride 

Downstream Products

• 19467-38-0 (Z)-2-hydroxy-3-[(1-oxo-9-octadecenyl)oxy]propyltrimethylammonium chloride 
• 118604-99-2 2-Hydroxy-3-(2-benzoylphenoxy)-N,N,N-trimethyl-1-propanaminium chloride 
• 118605-01-9 2-Hydroxy-3-(4-(4-methylbenzoyl)phenoxy)-N,N,N-trimethyl-1-propanaminium chloride 
• 118604-98-1 2-Hydroxy-3-(3-benzoylphenoxy)-N,N,N-trimethyl-1-propanaminium chloride 
• 118605-00-8 2-Hydroxy-3-(2-benzoyl-5-methoxyphenoxy)-N,N,N,-trimethyl-1-propanaminium chloride 
• 113184-23-9 2-hydroxy-3-(4-benzoylphenoxy)-N,N,N-trimethyl-1-propanaminium chloride 

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