119692-59-0

Basic information

• Product Name: 4-Hydroxybutyl acrylate glycidyl ether
• Synonyms: 4-Hydroxybutyl acrylate glycidyl ether;4-(2,3-EPOXYPROPOXY)BUTYLACRYLATE;4-(oxiran-2-ylmethoxy)butyl prop-2-enoate
• CAS NO: 119692-59-0
• Molecular Formula: C₁₀H₁₆O₄
• Molecular Weight: 200.23164
• Product Categories: Crosslinking monomer
• Mol File: 119692-59-0.mol

Chemical Properties

• Boiling Point: 287.531°C at 760 mmHg
• Flash Point: 123.267°C
• Appearance: /
• Density: 1.077g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.463
• CAS DataBase Reference: 4-Hydroxybutyl acrylate glycidyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxybutyl acrylate glycidyl ether(119692-59-0)
• EPA Substance Registry System: 4-Hydroxybutyl acrylate glycidyl ether(119692-59-0)

Safety Data

• Hazardous Substances Data: 119692-59-0(Hazardous Substances Data)

Usage

Uses

Used in Paint and Coating Materials:
4-Hydroxybutyl acrylate glycidyl ether is used as a component in paint and coating materials for its excellent scratch resistance, mechanical properties, and chemical properties.
Used in Powder Coatings:
4-Hydroxybutyl acrylate glycidyl ether is used as a component in powder coatings to enhance their performance and durability.
Used in UV/EB Curable Composition:
4-Hydroxybutyl acrylate glycidyl ether is used as a component in UV/EB curable compositions, contributing to their high crosslinking ratio and improved properties.
Used in Epoxy Acrylate:
4-Hydroxybutyl acrylate glycidyl ether is used as a component in epoxy acrylate formulations, providing improved crosslinking and acid rain resistance.
Used in Adhesives:
4-Hydroxybutyl acrylate glycidyl ether is used as a component in adhesives to improve their bonding strength and resistance to environmental factors.

Synthesis

The flask was charged with 144 g of 4-hydroxybutyl acrylate and 0.7 g of boron trifluoride ether complex as a catalyst, heated to 55 ° C., and then 92.5 g of epichlorohydrin was added dropwise over 2 hours with stirring. After completion of the dropwise addition, analysis by gas chromatography revealed that the conversion rate of 4-hydroxybutyl acrylate was about 70%, and most of it was converted to a chloroether form.

InChI:InChI=1/C10H16O4/c1-2-10(11)13-6-4-3-5-12-7-9-8-14-9/h2,9H,1,3-8H2

Synthetic route

1,4-butanediol monoglycidyl ether (4711-95-9) + ethyl acrylate (140-88-5) → 4-Hydroxybutyl acrylate glycidyl ether (119692-59-0)

Conditions	Yield
Stage #1: 1,4-butanediol monoglycidyl ether; ethyl acrylate With titanium(IV) isopropylate at 95℃; under 300.03 Torr; for 4h; Reflux; Stage #2: With 4-methoxy-phenol under 300.03 Torr;	97%
With titanium(IV) isopropylate; 4-methoxy-phenol at 95℃; under 300.03 Torr; for 6h; Reflux;

2-methoxyethyl acrylate (3121-61-7) + 1,4-butanediol monoglycidyl ether (4711-95-9) → 4-Hydroxybutyl acrylate glycidyl ether (119692-59-0)

Conditions	Yield
With tetrabutoxytitanium; 4-methoxy-phenol In o-xylene at 80 - 90℃; under 75.0075 Torr;	83.7%

tetrahydrofurfuryl acrylate (2399-48-6) + 1,4-butanediol monoglycidyl ether (4711-95-9) → 4-Hydroxybutyl acrylate glycidyl ether (119692-59-0)

Conditions	Yield
With tetrabutoxytitanium; 4-methylisopropylbenzene; 4-methoxy-phenol at 89 - 102℃; under 30.003 Torr;	70.4%

1,4-butanediol monoglycidyl ether (4711-95-9) + acrylic acid methyl ester (292638-85-8) → 4-Hydroxybutyl acrylate glycidyl ether (119692-59-0)

Conditions	Yield
With tetrabutoxytitanium; 4-methoxy-phenol In hexane; toluene at 72 - 92℃;	111.1 g

4-Hydroxybutyl acrylate glycidyl ether (119692-59-0) + 4-Hydroxybenzophenone (1137-42-4) → acrylic acid 4-[3-(4-benzoyl-phenoxy)-2-hydroxy-propoxy]butyl ester (1214748-83-0)

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Reflux;
With sodium hydroxide; potassium carbonate In hexane; dichloromethane; water; acetonitrile
With potassium carbonate In acetonitrile for 24h; Reflux;	5.5 g

2-Benzoylbenzoic acid (85-52-9) + 4-Hydroxybutyl acrylate glycidyl ether (119692-59-0) → 2-benzoyl-benzoic acid 3-(4-acryloyloxy-butoxy)-2-hydroxy-propyl ester (1214748-82-9)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; tetrabutylammomium bromide In ISOPROPYLAMIDE; acetonitrile for 16h; Reflux;
With 2,6-di-tert-butyl-4-methyl-phenol; tetrabutylammomium bromide In N,N-dimethyl acetamide; acetonitrile for 16h; Reflux;
With 2,6-di-tert-butyl-4-methyl-phenol; tetrabutylammomium bromide In N,N-dimethyl acetamide; acetonitrile for 16h; Reflux;	45.2 g

2-[(9-oxo-9H-thioxanthen-2-yl)oxy]-acetic acid (84434-05-9) + 4-Hydroxybutyl acrylate glycidyl ether (119692-59-0) → acrylic acid 4-{2-hydroxy-3-[2-(9-oxo-9H-thioxanthen-2-yloxy)-acetoxy]-propoxy}-butyl ester (1214748-81-8)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; tetrabutylammomium bromide In ISOPROPYLAMIDE; acetonitrile for 16h; Reflux;
With 2,6-di-tert-butyl-4-methyl-phenol; tetrabutylammomium bromide In acetonitrile for 16h; Reflux;	1.8 g

2[(9-oxo-9H-thioxanthen-2-yl)oxy]-propionic acid + 4-Hydroxybutyl acrylate glycidyl ether (119692-59-0) → acrylic acid 4-{2-hydroxy-3-[2-(9-oxo-9H-thioxanthen-2-yloxy)-propionyloxy]propoxy}-butyl ester (1214748-80-7)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; tetrabutylammomium bromide In ISOPROPYLAMIDE; acetonitrile for 16h; Reflux;
With 2,6-di-tert-butyl-4-methyl-phenol; tetrabutylammomium bromide In N,N-dimethyl acetamide; acetonitrile for 16h; Reflux;	3.7 g

9-oxo-9H-thioxanthen-1-carboxylic acid (51762-69-7) + 4-Hydroxybutyl acrylate glycidyl ether (119692-59-0) → 9-oxo-9H-thioxanthene-1-carboxylic acid-3-(4-acryloyloxy-butoxy)-2-hydroxy-propyl ester (1214748-78-3)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; tetrabutylammomium bromide In dimethyl sulfoxide; acetonitrile for 24h; Reflux;
With 2,6-di-tert-butyl-4-methyl-phenol; tetrabutylammomium bromide In dimethyl sulfoxide; acetonitrile for 24h; Reflux;
With 2,6-di-tert-butyl-4-methyl-phenol; tetrabutylammomium bromide In dimethyl sulfoxide; acetonitrile for 24h; Reflux;	2.6 g

9-oxo-9H-thioxanthene-2-carboxylic acid (25095-94-7) + 4-Hydroxybutyl acrylate glycidyl ether (119692-59-0) → 9-oxo-9H-thioxanthene-2-carboxylic acid-3-(4-acryloyloxy-butoxy)-2-hydroxy-propyl ester (1214748-79-4)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; tetrabutylammomium bromide In ISOPROPYLAMIDE; acetonitrile for 24h; Reflux;
With 2,6-di-tert-butyl-4-methyl-phenol; tetrabutylammomium bromide In N,N-dimethyl acetamide; acetonitrile for 24h; Reflux;
With 2,6-di-tert-butyl-4-methyl-phenol; tetrabutylammomium bromide In N,N-dimethyl acetamide; acetonitrile for 24h; Reflux;	2.5 g

4-Hydroxybutyl acrylate glycidyl ether (119692-59-0) + C29H29NO4 → C39H45NO8 (1311143-99-3)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; tetrabutylammomium bromide In acetonitrile for 16h; Reflux;

2-Benzoylbenzoic acid (85-52-9) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 4-Hydroxybutyl acrylate glycidyl ether (119692-59-0) → 2-benzoyl-benzoic acid 3-(4-acryloyloxy-butoxy)-2-hydroxy-propyl ester (1214748-82-9)

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In tert-butyl methyl ether; ISOPROPYLAMIDE; water; acetonitrile

2-[(9-oxo-9H-thioxanthen-2-yl)oxy]-acetic acid (84434-05-9) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 4-Hydroxybutyl acrylate glycidyl ether (119692-59-0) → acrylic acid 4-{2-hydroxy-3-[2-(9-oxo-9H-thioxanthen-2-yloxy)-acetoxy]-propoxy}-butyl ester (1214748-81-8)

Conditions	Yield
With tetrabutylammomium bromide In ISOPROPYLAMIDE; acetonitrile

2[(9-oxo-9H-thioxanthen-2-yl)oxy]-propionic acid + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 4-Hydroxybutyl acrylate glycidyl ether (119692-59-0) → acrylic acid 4-{2-hydroxy-3-[2-(9-oxo-9H-thioxanthen-2-yloxy)-propionyloxy]propoxy}-butyl ester (1214748-80-7)

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In tert-butyl methyl ether; ISOPROPYLAMIDE; water; acetonitrile

9-oxo-9H-thioxanthen-1-carboxylic acid (51762-69-7) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 4-Hydroxybutyl acrylate glycidyl ether (119692-59-0) → 9-oxo-9H-thioxanthene-1-carboxylic acid-3-(4-acryloyloxy-butoxy)-2-hydroxy-propyl ester (1214748-78-3)

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In dichloromethane; water; dimethyl sulfoxide; ethyl acetate; acetonitrile

9-oxo-9H-thioxanthene-2-carboxylic acid (25095-94-7) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) + 4-Hydroxybutyl acrylate glycidyl ether (119692-59-0) → 9-oxo-9H-thioxanthene-2-carboxylic acid-3-(4-acryloyloxy-butoxy)-2-hydroxy-propyl ester (1214748-79-4)

Conditions	Yield
With sodium hydroxide; tetrabutylammomium bromide In tert-butyl methyl ether; ISOPROPYLAMIDE; water; acetonitrile

(1-chloro-9-oxo-9H-thioxanthen-4-yloxy)-acetic acid + 4-Hydroxybutyl acrylate glycidyl ether (119692-59-0) → acrylic acid 4-{3-[2-(1-chloro-9-oxo-9H-thioxanthen-4-yloxy)-acetoxy]-2-hydroxy-propoxy}-butyl ester (1372490-05-5)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; tetrabutylammomium bromide In ISOPROPYLAMIDE; acetonitrile for 24h; Reflux;
With 2,6-di-tert-butyl-4-methyl-phenol In ISOPROPYLAMIDE; acetonitrile for 24h; Reflux;

4-Hydroxybutyl acrylate glycidyl ether (119692-59-0) + (1-fluoro-9-oxo-9H-thioxanthen-4-yloxy)-acetic acid (1372490-34-0) → acrylic acid 4-{3-[2-(1-fluoro-9-oxo-9H-thioxanthen-4-yloxy)-acetoxy]-2-hydroxy-propoxy}-butyl ester (1372490-37-3)

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; tetrabutylammomium bromide In ISOPROPYLAMIDE; acetonitrile at 94℃; for 24h;
With 2,6-di-tert-butyl-4-methyl-phenol; tetrabutylammomium bromide In ISOPROPYLAMIDE; acetonitrile at 94℃; for 24h;

2,2-dimethyl-4-methylenepentanedioic acid (10297-25-3) + 4-Hydroxybutyl acrylate glycidyl ether (119692-59-0) → AFM-6 (1392192-38-9)

Conditions	Yield
With triphenylantimony; triphenylphosphine at 100℃; for 45.5h;

4-Hydroxybutyl acrylate glycidyl ether (119692-59-0) + 2-Phosphono-butane-1,2,4-tricarboxylic acid → C37H59O21P

Conditions	Yield
With tetrabutylammomium bromide In isopropyl alcohol; acetonitrile Inert atmosphere;

4-Hydroxybutyl acrylate glycidyl ether (119692-59-0) + dibutyl phosphate (107-66-4) → C18H35O8P

Conditions	Yield
at 60℃; for 1h;

Upstream product

• 4711-95-9 1,4-butanediol monoglycidyl ether 
• 292638-85-8 acrylic acid methyl ester 
• 3121-61-7 2-methoxyethyl acrylate 
• 2399-48-6 tetrahydrofurfuryl acrylate 
• 140-88-5 ethyl acrylate 

Downstream Products

• 1214748-83-0 acrylic acid 4-[3-(4-benzoyl-phenoxy)-2-hydroxy-propoxy]butyl ester 
• 1214748-82-9 2-benzoyl-benzoic acid 3-(4-acryloyloxy-butoxy)-2-hydroxy-propyl ester 
• 1311143-99-3 C₃₉H₄₅NO₈ 

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