94-28-0

Usage

Uses

Used in Plasticizer Applications:
Triethylene glycol bis(2-ethylhexanoate) is used as a plasticizer to improve the flexibility, elongation, and toughness of polymers. It is particularly effective in reducing the brittleness and increasing the workability of materials, making them more suitable for a wide range of applications.
Used in Viscosity Modifier Applications:
As a viscosity modifier, Triethylene glycol bis(2-ethylhexanoate) is utilized to adjust the flow properties of liquids and pastes. This allows for better control over the application process and improved performance of the final product.
Used in Automobile Industry:
In the automobile industry, Triethylene glycol bis(2-ethylhexanoate) is used as a viscosity modifier for PVB (polyvinyl butyral) film. This film is an essential component in the laminated glass of automobile front windshields, where it serves to hold the glass layers together in the event of an impact, enhancing safety and durability.
Used in Film Manufacturing:
Triethylene glycol bis(2-ethylhexanoate) is also used in the manufacturing of films, particularly for improving the dispersibility and workability of PVB film. This contributes to the production of high-quality films with desirable properties, such as increased transparency, flexibility, and resistance to environmental factors.

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 academic research and scientific papers

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 OF PREPARING GLYCOL ESTERS WITH LOW COLOR AND PEROXIDE CONTENT

?The present invention relates to the field of preparing glycol esters used as plasticizers in the manufacture of films for multilayered glass. In particular, the invention relates to a method for preparing triethylene glycol ester of 2-ethylhexanoic acid. The claimed method includes the steps of esterification, clarification of a crude ester by treating thereof with hydrogen peroxide and alkali metal metasilicate at a temperature of from 70 to 200oC, inclusive, and allowing to stand for 0.5 to 1.5 hours, inclusive, to obtain a clarified ester, neutralization of acidic compounds in the clarified ester by treating thereof with an alkaline solution, filtration, and drying of the ester. The technical result of the invention is the development of an economical and safe method of preparing glycol esters that are characterized by low values of color, acidity and peroxide content.

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 Post-Treating Polyol Esters

A batchwise process for aftertreatment of polyol esters prepared by reacting polyols of the general formula (II) [in-line-formulae]H—(—O—[—CR1R2—]m—)o—OH ??(II)[/in-line-formulae] in which R1 and R2 are each independently hydrogen, an alkyl radical having 1 to 5 carbon atoms, preferably methyl, ethyl or propyl, or a hydroxyalkyl radical having 1 to 5 carbon atoms, preferably the hydroxymethyl radical, m is an integer from 1 to 10, preferably 1 to 8 and especially 1, 2, 3 or 4, o is an integer from 2 to 15, preferably 2 to 8 and especially 2, 3, 4 or 5, with excess linear or branched aliphatic monocarboxylic acids having 3 to 20 carbon atoms and having a lower boiling point than the polyols used. The process is carried out in the presence of a Lewis acid and in the presence of an adsorbent, while removing the water formed, characterized in that the excess monocarboxylic acid is removed by distillation and water is added to the crude ester obtained at a temperature below the boiling point of water at the particular pressure and the crude ester with added water is aftertreated with avoidance of basic compounds, and the sparingly soluble conversion products and the adsorbent present in the esterification reaction are filtered off.

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.

PROCESS FOR PREPARING POLYOL ESTERS

The present invention relates to a process for preparing polyol esters by reacting polyols with linear or branched aliphatic monocarbocxylic acids having 3 to 20 carbon atoms, the reaction taking place in the presence of a Lewis acid comprising at least one element from groups 4 to 14 of the Periodic Table of the Elements as catalyst, and in the presence of an adsorbent, the reaction product being subjected subsequently to a steam treatment.

Process for preparing polyol esters

The present invention relates to a process for preparing polyol esters by reacting polyols with linear or branched aliphatic monocarboxylic acids having 3 to 20 carbon atoms in the presence of an adsorbent and subsequent steam treatment in the course of workup of the crude ester.

Process for preparing polyol esters

The present invention relates to a process for preparing polyol esters by reacting polyols with linear or branched aliphatic monocarboxylic acids having 3 to 20 carbon atoms by partial recycling of the aliphatic monocarboxylic acid removed into the esterification reaction or into subsequent esterification batches.

TRIETHYLENEGLYCOL ESTER BASED PLASTICIZER COMPOSITION FOR POLYVINYL CHLORIDE RESIN AND METHOD OF PREPARING THE SAME

Provided is a novel triethyleneglycol based compound, a plasticizer composition for polyvinyl chloride resin including the same, and a method of preparing the plasticizer composition. In particular, the plasticizer composition for polyvinyl chloride resin includes the novel compound, 2-(2-(2-(2-ethylhexanoyloxy)ethoxy)ethoxy)ethyl 2-ethylhexanoate, and 2-(2-(2-phenylcarbonyloxyethoxy)ethoxy)ethyl benzoate in a proper mixture ratio. A polyvinyl chloride prepared using the plasticizer composition has low heating loss, excellent adhesion, high plasticization efficiency, high elongation, high tensile strength, and high transparency.