94-28-0

Basic information

• Product Name: Triethylene glycol bis(2-ethylhexanoate)
• Synonyms: 1,2-bis-[2-(2-ethyl-hexanoyloxy)-ethoxy]-ethane;2-(2-(2-[(2-Ethylhexanoyl)oxy]ethoxy)ethoxy)ethyl 2-ethylhexanoate;2-ethyl-hexanoicacidiesterwithtriethyleneglycol;Ethane, 1,2-(2'-hydroxyethoxy)-, di-(2-ethylhexanoate)-;Flexol plasticizer 3go;flexol3go;flexolplasticizer3go;Hexanoic acid, 2-ethyl-, 1,2-ethanediylbis(oxy-2,1-ethanediyl) ester
• CAS NO: 94-28-0
• Molecular Formula: C₂₂H₄₂O₆
• Molecular Weight: 402.57
• EINECS: 202-319-2
• Mol File: 94-28-0.mol
• Article Data: 9

Chemical Properties

• Melting Point: −50 °C(lit.)
• Boiling Point: 344 °C(lit.)
• Flash Point: >230 °F
• Appearance: clear very slightly yellow liquid
• Density: 0.97 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.001Pa at 25℃
• Refractive Index: n20/D 1.445
• Water Solubility: Insoluble
• CAS DataBase Reference: Triethylene glycol bis(2-ethylhexanoate)(CAS DataBase Reference)
• NIST Chemistry Reference: Triethylene glycol bis(2-ethylhexanoate)(94-28-0)
• EPA Substance Registry System: Triethylene glycol bis(2-ethylhexanoate)(94-28-0)

Safety Data

• Safety Statements: 24/25
• RTECS: MO7725000
• TSCA: Yes
• Hazardous Substances Data: 94-28-0(Hazardous Substances Data)

Usage

Uses

Tri(ethylenglycol)bis-2-ethylhexanoate is a plasticizer; it is used method for improving dispersibility of PVB film viscosity modifier for automobile front windshield laminated glass.

Synthetic route

2-Ethylhexanoic acid (149-57-5) + 2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → triethylene glycol bis(2-ethylhexanoate) (94-28-0)

Conditions	Yield
With titanium(IV) isopropylate at 220℃; under 225.023 - 450.045 Torr; for 3h; Reagent/catalyst; Pressure; Time; Concentration; pH-value;	97%
With pyrographite at 225℃; under 300.03 - 675.068 Torr; for 14.5h; Product distribution / selectivity;
With pyrographite at 225℃; under 300.03 - 675.068 Torr; for 14.5h; Product distribution / selectivity;

2-Ethylhexanoic acid (149-57-5) + benzoic acid (65-85-0) + 2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → 2-(2-(2-phenylcarbonyloxyethoxy)ethoxy)ethyl 2-ethylhexanoate + triethylene glycol bis(2-ethylhexanoate) (94-28-0) + triethylene glycol dibenzoate (120-56-9)

Conditions	Yield
titanium(IV) isopropylate In xylene at 220℃; for 6h; Product distribution / selectivity;

2-ethylhexanoic acid chloride (760-67-8) → triethylene glycol bis(2-ethylhexanoate) (94-28-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: propan-1-ol / 3.5 - 20 °C / Inert atmosphere 2: sodium methylate / 22 h / 138 °C View Scheme
Multi-step reaction with 2 steps 1: propan-1-ol / 3.5 - 20 °C / Inert atmosphere 2: potassium carbonate / 4 h / 160 °C View Scheme

methyl 2-ethylhexanoate (816-19-3) + 2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → triethylene glycol bis(2-ethylhexanoate) (94-28-0) + triethylene glycol 2-ethylhexanoate

Conditions	Yield
With sodium methylate at 138℃; for 22h; Time;

methyl 2-ethylhexanoate (816-19-3) + 2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → triethylene glycol bis(2-ethylhexanoate) (94-28-0)

Conditions	Yield
With potassium carbonate at 160℃; for 4h; Reagent/catalyst; Temperature;

Upstream product

• 816-19-3 methyl 2-ethylhexanoate 
• 112-27-6 2,2'-[1,2-ethanediylbis(oxy)]bisethanol 
• 760-67-8 2-ethylhexanoic acid chloride 
• 149-57-5 2-Ethylhexanoic acid 
• 65-85-0 benzoic acid 

Relevant articles and documents

SYNTHESIS OF TRIETHYLENE GLYCOL BIS(2-ETHYLHEXANOATE)

A process for the transesterification of methyl-2- ethylhexanoate with triethylene glycol to produce triethylene glycol di-2-ethylhexanoate is provided. In the process, methyl-2- ethylhexanoate is combined with triethylene glycol to form a first mixture. The first mixture is heated in the presence of a catalyst to form a second mixture comprising methanol and triethylene glycol di-2-ethylhexanoate. Methanol is separated from the second mixture to yield triethylene glycol di-2-ethylhexanoate. Na2CO3, CS2CO3, K2CO3, Rb2CO3, sodium methoxide or titanium isopropoxide are suitable catalysts.

METHOD FOR PRODUCING AN ESTER

Disclosed is a method for production of an ester obtained from a reaction between at least one alcohol having at least one hydroxyl group, such as a diol, and at least one linear of branched C3-C20 monocarboxylic acid, said reaction being performed in presence of at least one azeotropic solvent and optionally at least one antioxidant. Said method comprises the steps of (a) charging said alcohol, said monocarboxylic acid, and said azeotropic solvent and optionally said antioxidant to a reactor, (b) subjecting said alcohol and said carboxylic acid to esterification under reflux, (c) removing azeotropic solvent and unreacted carboxylic acid from yielded reaction mixture, (d) steam stripping off residual unreacted carboxylic acid, (e) neutralising yielded reaction product with an aqueous base, (f) separating water and organic phases, (g) recovering said organic phase and evaporating residual water, and (h) filtering off said antioxidant and possible remaining salts in yielded reaction product. The method is preferably performed in at least one reactor equipped with reflux, at least one vacuum pump, evaporation/distillation, steam stripping and decantation, and at least one filtration unit and optionally at least one coalescer filtre.

Method for Producing Polyol Esters

A process for preparing polyol esters by reacting polyols with linear or branched aliphatic monocarboxylic acids having 3 to 20 carbon atoms, is characterized in that a mixture of the starting compounds is allowed to react in the presence of a Lewis acid containing at least one element of groups 4 to 14 of the periodic table of the elements as a catalyst and in the presence of an adsorbent with removal of the water formed, and then the crude ester obtained is aftertreated by adding a further adsorbent which is an acidic activated carbon having a pH of 1 to 6.5.