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109-16-0

Basic Information
CAS No.: 109-16-0
Name: Triethylene glycol dimethacrylate
Article Data: 21
Molecular Structure:
Molecular Structure of 109-16-0 (Triethylene glycol dimethacrylate)
Formula: C14H22O6
Molecular Weight: 286.325
Synonyms: 2-Propenoicacid, 2-methyl-, 1,2-ethanediylbis(oxy-2,1-ethanediyl) ester (9CI);Methacrylicacid, diester with triethylene glycol (6CI,8CI);Methacrylic acid,ethylenebis(oxyethylene) ester (7CI);1,2-Bis[2-(methacryloyloxy)ethoxy]ethane;ATM 2 (methacrylate);Acryester 3ED;Bisomer TEGDMA;Blemmer PDE 150;Esschem 943X7469;Ethylenebis(oxyethylene) methacrylate;Light Ester 3EG;NKEster 3G;NSC 84260;Neomer PM 201;New Frontier NF Bisomer TEGDMA;SR 205;Sartomer SR 205;TEDMA;TGM 3;TGM 3PC;TGM 3S;Triethylene glycoldimethacrylate;
EINECS: 203-652-6
Density: 1.063 g/cm3
Melting Point: -52 °C
Boiling Point: 335.5 °C at 760 mmHg
Flash Point: 159.1 °C
Solubility: 3.6g/L at 20℃
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-28
PSA: 71.06000
LogP: 1.25820
Synthetic route
753-73-1

dimethyltin dichloride

150-76-5

4-methoxy-phenol

80-62-6

methacrylic acid methyl ester

109-16-0

triethyleneglycol dimethacrylate

Conditions
ConditionsYield
With sodium methylate; hydroquinone In n-heptane; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol91%
920-46-7

Methacryloyl chloride

201037-95-8

2-(2-(2-(tert-butyl-dimethyl-silanyloxy)-ethoxy)-ethoxy)-ethanol

A

109-16-0

triethyleneglycol dimethacrylate

B

495417-68-0

2-[2-[2-[(tert-butyldimethylsilyl)oxy]ethoxy]ethoxy]ethyl methacrylate

Conditions
ConditionsYield
With triethylamine In diethyl ether at 20℃;A n/a
B 81%
920-46-7

Methacryloyl chloride

112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

109-16-0

triethyleneglycol dimethacrylate

Conditions
ConditionsYield
With sodium hydroxide
79-41-4

poly(methacrylic acid)

112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

109-16-0

triethyleneglycol dimethacrylate

Conditions
ConditionsYield
With sulfuric acid
80-62-6

methacrylic acid methyl ester

112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

109-16-0

triethyleneglycol dimethacrylate

Conditions
ConditionsYield
With sodium methylate; hydroquinone
79-41-4

poly(methacrylic acid)

112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

A

109-16-0

triethyleneglycol dimethacrylate

B

2351-42-0

2-(2-(2-hydroxyethoxy)ethoxy)ethyl methacrylate

C

107-21-1

ethylene glycol

D

111-46-6

diethylene glycol

Conditions
ConditionsYield
toluene-4-sulfonic acid at 70 - 100℃; Kinetics; bulbs method; at various concentrations of catalyst;
112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

109-16-0

triethyleneglycol dimethacrylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 73 percent / pyridine / CH2Cl2 / 20 °C
2: triethylamine / diethyl ether / 20 °C
View Scheme
920-46-7

Methacryloyl chloride

112-27-6

2,2'-[1,2-ethanediylbis(oxy)]bisethanol

A

109-16-0

triethyleneglycol dimethacrylate

B

2351-42-0

2-(2-(2-hydroxyethoxy)ethoxy)ethyl methacrylate

Conditions
ConditionsYield
Stage #1: 2,2'-[1,2-ethanediylbis(oxy)]bisethanol With pyridine In dichloromethane at 18 - 28℃; for 0.5h; Inert atmosphere;
Stage #2: Methacryloyl chloride In dichloromethane at 18 - 28℃; for 4h; Cooling with ice; Inert atmosphere;

5-norbornen-2-yl acetate

109-16-0

triethyleneglycol dimethacrylate

poly(triethylene glycol dimethacrylate-co-5-norbornen-2-yl acetate)

poly(triethylene glycol dimethacrylate-co-5-norbornen-2-yl acetate)

Conditions
ConditionsYield
(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)(η6-p-cymene)RuCl2 for 0.0333333h; blue light irradiation;99%
109-16-0

triethyleneglycol dimethacrylate

polymer, crosslinked, obtained by polymerization triethyleneglycol dimethylacrylate, initiated by N-propyloyloxytrimethylammonium tetraphenylborate; monomer(s): triethyleneglycol dimethylacrylate

polymer, crosslinked, obtained by polymerization triethyleneglycol dimethylacrylate, initiated by N-propyloyloxytrimethylammonium tetraphenylborate; monomer(s): triethyleneglycol dimethylacrylate

Conditions
ConditionsYield
With sulfuric acid for 0.00416667h;98%
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The Methacrylic acid, diester with triethylene glycol is an organic compound with the formula C14H22O6. The IUPAC name of this chemical is 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate. With the CAS registry number 109-16-0, it is also named as 1,2-Ethanediylbis(oxy-2,1-ethanediyl) bis(2-methylacrylate). The product's categories are Functional Monomer; Biocompatible/Biodegradable Materials; C12 to C63Materials Science; Carbonyl Compounds; Crosslinking AgentsPolymer Science; Esters; Homobifunctional PEGs; Poly(ethylene glycol) and Poly(ethylene oxide). Besides, it is widely used in epoxy / polyester hybrid coating, also used for spinning polyester fibers.

Physical properties about Methacrylic acid, diester with triethylene glycol are: (1)ACD/LogP: 1.81; (2)ACD/LogD (pH 5.5): 1.81; (3)ACD/LogD (pH 7.4): 1.81; (4)ACD/BCF (pH 5.5): 13.93; (5)ACD/BCF (pH 7.4): 13.93; (6)ACD/KOC (pH 5.5): 229.31; (7)ACD/KOC (pH 7.4): 229.31; (8)#H bond acceptors: 6; (9)#Freely Rotating Bonds: 13; (10)Polar Surface Area: 71.06 Å2; (11)Index of Refraction: 1.455; (12)Molar Refractivity: 73.08 cm3; (13)Molar Volume: 269.1 cm3; (14)Polarizability: 28.97×10-24cm3; (15)Surface Tension: 33.6 dyne/cm; (16)Density: 1.063 g/cm3; (17)Flash Point: 159.1 °C; (18)Enthalpy of Vaporization: 57.86 kJ/mol; (19)Boiling Point: 335.5 °C at 760 mmHg; (20)Vapour Pressure: 0.000119 mmHg at 25°C.

Uses of Methacrylic acid, diester with triethylene glycol: it can be used to produce poly(styrene-co-triethyleneglycol dimethacrylate), crosslinked, radical suspension polymerized, 2 mol percent triethyleneglycol dimethacrylate; monomers: styrene; triethyleneglycol dimethacrylate at temperature of 80 °C. This reaction is a kind of Polymerization. It will need reagent benzoyl peroxide, polyvinylalcohol and solvent toluene, H2O with reaction time of 8 hours. The yield is about 54%.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. After contact with skin, you should wash immediately with plenty of ... (to be specified by the manufacturer).

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OCCOCCOCCOC(=O)\C(=C)C)\C(=C)C
(2)InChI: InChI=1/C14H22O6/c1-11(2)13(15)19-9-7-17-5-6-18-8-10-20-14(16)12(3)4/h1,3,5-10H2,2,4H3
(3)InChIKey: HWSSEYVMGDIFMH-UHFFFAOYAE
(4)Std. InChI: InChI=1S/C14H22O6/c1-11(2)13(15)19-9-7-17-5-6-18-8-10-20-14(16)12(3)4/h1,3,5-10H2,2,4H3
(5)Std. InChIKey: HWSSEYVMGDIFMH-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 10750mg/kg (10750mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 47(4), Pg. 17, 1982.
rat LD50 oral 10837mg/kg (10837mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 47(4), Pg. 17, 1982.