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
• Article Data: 2

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

Description

4-Hydroxybutyl Acryrate Glycidyl Ether with a glycidylether group at the end of a longer alkyl chain, gives excellent scratch resistance due to its high crosslinking ratio and unique flexibility.This copolymer has good acid rain resistance.It is used in Paint and coating materials,UV/EB curable composition.

Chemical Properties

4HBAGE has a glycidylether functional group and a double bond group in the molecule.Various vinyl monomers can be copolymerized with 4HBAGE.The co-polymerized polymer with 4HBAGE achieves a higher crosslinking ratio with curing agents.This is because the glycidylether is further away from the copolymer backbone chain.This copolymer has good acid rain resistance.

Application

Paint and coating materials (excellent scratch resistance, mechanical properties, and chemical properties)Powder coatingsUV/EB curable composition.Epoxy acrylateAdhesives

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

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

Relevant articles and documents

(Meth) acrylate, an epoxy group end manufacturing method

PROBLEM TO BE SOLVED: To provide a method of producing an epoxy-terminated (meth)acrylate of high purity at a high yield, by preventing the polymerization of an epoxy-terminated (meth)acrylate during its distillation/purification. SOLUTION: The method of producing an epoxy-terminated (meth)acrylate represented by formula (1) by subjecting a (meth)acrylate compound and a compound comprising a specific glycidyl group to a transesterification reaction in the presence of a metal alcoholate and subsequently distilling/purifying the resulting epoxy-terminated (meth)acrylate in the presence of a polymerization inhibitor which is a copper compound, is characterized by keeping the amount of the metal contained therein derived from the metal alcoholate not higher than 500 ppm and not higher than 2.5 times in the molar ratio relative to the polymerization inhibitor present in the distillation/purification process (in the formula, Y represents a 2C-8C saturated hydrocarbon group, and R represents a hydrogen atom or a methyl group). COPYRIGHT: (C)2011,JPOandINPIT