6422-86-2

Basic information

• Product Name: Dioctyl terephthalate
• Synonyms: di-(2-ethylhexyl)terephthalate;Di(2-ethylhexyl)terephthalate;kodaflexdotp;terephthalicacid,bis(2-ethylhexyl)ester;DIOCTYL TEREPHTHALATE;DOTP;EASTMAN PA-6 PLASTICIZER ADHESIVE;BIS(2-ETHYLHEXYL) TEREPHTHALATE
• CAS NO: 6422-86-2
• Molecular Formula: C₂₄H₃₈O₄
• Molecular Weight: 390.56
• EINECS: 229-176-9
• Mol File: 6422-86-2.mol
• Article Data: 29

Chemical Properties

• Melting Point: 30-34 °C(lit.)
• Boiling Point: 400 °C(lit.)
• Flash Point: 230 °F
• Appearance: Clear colorless/Liquid
• Density: 0.986 g/mL at 25 °C(lit.)
• Vapor Pressure: 1 mm Hg ( 217 °C)
• Refractive Index: n20/D 1.49(lit.)
• Storage Temp.: 2-8°C
• Solubility: Aqueous Base (Slightly)
• Water Solubility: insoluble
• Stability: Hygroscopic
• CAS DataBase Reference: Dioctyl terephthalate(CAS DataBase Reference)
• NIST Chemistry Reference: Dioctyl terephthalate(6422-86-2)
• EPA Substance Registry System: Dioctyl terephthalate(6422-86-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 1
• RTECS: WZ0883500
• Hazardous Substances Data: 6422-86-2(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless liquid

Uses

Different sources of media describe the Uses of 6422-86-2 differently. You can refer to the following data:
1. It is used primarily as a plasticizer for polyvinyl chloride and other polymers.
2. DOTP can form a composite blend with polyaniline (PANI)-ethyene dimethacrylate (EDMA), which can be used in the fabrication of conductive films. It may also be used as a plasticizer with polyvinyl chloride (PVC) to form solutions for artificial intravessel plaque.

Production Methods

DEHT is manufactured by the esterification of terephthalic acid and 2-ethylhexanol.

General Description

Dioctyl terephthalate (DOTP) is a plasticizer that can be prepared by alcoholysis of polyethylene terephthalate (PET) with isooctyl alcohol.

Carcinogenicity

The carcinogenic potential of DEHT was evaluated in a 2-year study in which male and female rats were given diets containing 1500, 6000, or 12,000 ppm. There was no effect on tumor incidence, and therefore, the NOEL for tumorigenicity was at least 12,000 ppm (equivalent to 666 mg/kg/day in males and 901 mg/kg/day in females).

InChI:InChI=1/C24H38O4/c1-5-9-11-19(7-3)17-27-23(25)21-13-15-22(16-14-21)24(26)28-18-20(8-4)12-10-6-2/h13-16,19-20H,5-12,17-18H2,1-4H3/t19-,20-/m1/s1

Synthetic route

2-Ethylhexyl alcohol (104-76-7) + terephthalic acid (100-21-0) → di(2-ethylhexyl)terephthalate (6422-86-2)

Conditions	Yield
With phenol and titanium tetraisopropoxide resin at 200℃; for 4h; Reagent/catalyst; Dean-Stark; Inert atmosphere;	99.5%
With titanium(IV) isopropylate at 170 - 200℃; Inert atmosphere; Large scale;	99%
With titanium(IV) isopropylate at 170 - 220℃; under 760.051 Torr; for 4.5h; Inert atmosphere; Large scale;	99%

2-Ethylhexyl alcohol (104-76-7) + polyethylene terephthalate → di(2-ethylhexyl)terephthalate (6422-86-2)

Conditions	Yield
With choline chloride; zinc diacetate at 185℃; for 1h; Kinetics; Reagent/catalyst; Temperature; Time; Green chemistry;	84.2%
With titanium(IV) isopropylate at 180 - 225℃; for 5h; Inert atmosphere;

terephthalic acid (100-21-0) + (+-)-2-ethyl-hexanol → di(2-ethylhexyl)terephthalate (6422-86-2)

2-Ethylhexyl alcohol (104-76-7) + terephthalic acid (100-21-0) + butan-1-ol (71-36-3) → di-n-butyl terephthalate (1962-75-0) + di(2-ethylhexyl)terephthalate (6422-86-2) + 1-butyl 4-(2-ethylhexyl)terephthalate

Conditions	Yield
With methanesulfonic acid at 210℃; under 760.051 Torr; for 4h; Inert atmosphere;

2-Ethylhexyl alcohol (104-76-7) + di-n-butyl terephthalate (1962-75-0) → di(2-ethylhexyl)terephthalate (6422-86-2) + 1-butyl 4-(2-ethylhexyl)terephthalate

Conditions	Yield
at 140℃; for 5h; Inert atmosphere;

di(2-ethylhexyl)terephthalate (6422-86-2) → bis(2-ethylhexyl)cyclohexane-1,4-dicarboxylate (84731-70-4)

Conditions	Yield
With hydrogen at 150℃; under 60006 Torr; for 3h;	99%
With hydrogen; alumina substrate/0.05 wtpercent Ru at 140℃; under 150015 Torr; for 3.5h;	97%

di(2-ethylhexyl)terephthalate (6422-86-2) + butan-1-ol (71-36-3) → di-n-butyl terephthalate (1962-75-0) + 1-butyl 4-(2-ethylhexyl)terephthalate

Conditions	Yield
With titanium tetraisopropoxide at 160℃; for 4h; Reagent/catalyst; Temperature; Concentration; Inert atmosphere; Large scale;
at 160℃; for 2h; Inert atmosphere;
at 160℃; for 2h; Inert atmosphere;

2-Ethylhexyl alcohol (104-76-7) + terephthalic acid (100-21-0) → di(2-ethylhexyl)terephthalate (6422-86-2)

Conditions	Yield
With phenol and titanium tetraisopropoxide resin at 200℃; for 4h; Reagent/catalyst; Dean-Stark; Inert atmosphere;	99.5%
With titanium(IV) isopropylate at 170 - 200℃; Inert atmosphere; Large scale;	99%
With titanium(IV) isopropylate at 170 - 220℃; under 760.051 Torr; for 4.5h; Inert atmosphere; Large scale;	99%

2-Ethylhexyl alcohol (104-76-7) + polyethylene terephthalate → di(2-ethylhexyl)terephthalate (6422-86-2)

Conditions	Yield
With choline chloride; zinc diacetate at 185℃; for 1h; Kinetics; Reagent/catalyst; Temperature; Time; Green chemistry;	84.2%
With titanium(IV) isopropylate at 180 - 225℃; for 5h; Inert atmosphere;

terephthalic acid (100-21-0) + (+-)-2-ethyl-hexanol → di(2-ethylhexyl)terephthalate (6422-86-2)

2-Ethylhexyl alcohol (104-76-7) + terephthalic acid (100-21-0) + butan-1-ol (71-36-3) → di-n-butyl terephthalate (1962-75-0) + di(2-ethylhexyl)terephthalate (6422-86-2) + 1-butyl 4-(2-ethylhexyl)terephthalate

Conditions	Yield
With methanesulfonic acid at 210℃; under 760.051 Torr; for 4h; Inert atmosphere;

2-Ethylhexyl alcohol (104-76-7) + di-n-butyl terephthalate (1962-75-0) → di(2-ethylhexyl)terephthalate (6422-86-2) + 1-butyl 4-(2-ethylhexyl)terephthalate

Conditions	Yield
at 140℃; for 5h; Inert atmosphere;

2-Ethylhexyl alcohol (104-76-7) + bis(2-propylheptyl)terephthalate → di(2-ethylhexyl)terephthalate (6422-86-2) + 2-propylheptyl 2-ethylhexyl terephthalate

Conditions	Yield
With titanium tetraisopropoxide at 160℃; for 5h; Inert atmosphere;

terephthalic acid (100-21-0) → di(2-ethylhexyl)terephthalate (6422-86-2) + 1-butyl 4-(2-ethylhexyl)terephthalate

Conditions	Yield
Multi-step reaction with 2 steps 1: methanesulfonic acid / 4 h / 210 °C / 760.05 Torr / Inert atmosphere 2: 5 h / 140 °C / Inert atmosphere View Scheme

1,4-benzenedicarboxylic acid dimethyl ester (120-61-6) + 2-Ethylhexyl alcohol (104-76-7) → di(2-ethylhexyl)terephthalate (6422-86-2)

Conditions	Yield
With titanium(IV) isopropylate; 2-(Ethylamino)ethanol for 1.4h; Heating;

2-Ethylhexyl alcohol (104-76-7) + isophthalic acid (121-91-5) + terephthalic acid (100-21-0) → Bis(2-ethylhexyl) isophthalate (137-89-3) + di(2-ethylhexyl)terephthalate (6422-86-2)

Conditions	Yield
With titanium(IV) tetraethanolate at 220℃; for 5h; Concentration; Inert atmosphere;

2-propylheptan-1-ol (10042-59-8) + 2-Ethylhexyl alcohol (104-76-7) + terephthalic acid (100-21-0) → di(2-ethylhexyl)terephthalate (6422-86-2) + bis(2-propylheptyl)terephthalate + 2-propylheptyl 2-ethylhexyl terephthalate

Conditions	Yield
With titanium(IV) isopropylate at 235℃; for 4h; Temperature; Inert atmosphere;

2-Ethylhexyl alcohol (104-76-7) + 2-isononyl alcohol (66793-83-7) + terephthalic acid (100-21-0) → di(2-ethylhexyl)terephthalate (6422-86-2) + diisononyl terephthalate + ethylhexyl isononyl terephthalate

Conditions	Yield
With titanium(IV) isopropylate at 220℃; for 9h;	A 10 %Chromat. B 36 %Chromat. C 54 %Chromat.

6-methylheptanol (1653-40-3) + terephthalic acid (100-21-0) → di(2-ethylhexyl)terephthalate (6422-86-2)

Conditions	Yield
With titanium(IV) isopropylate; monobutyltin triisooctanoate at 150 - 230℃; for 2h; Reagent/catalyst; Temperature;

2-Ethylhexyl alcohol (104-76-7) + 7-methyl-1-octanol (2430-22-0) + terephthalic acid (100-21-0) → diisononyl terephthalate + di(2-ethylhexyl)terephthalate (6422-86-2) + (2-ethylhexyl) isononyl terephthalate

Conditions	Yield
With titanium(IV) isopropylate at 170 - 220℃; for 4.5h; Inert atmosphere;

di(2-ethylhexyl)terephthalate (6422-86-2) → bis(2-ethylhexyl)cyclohexane-1,4-dicarboxylate (84731-70-4)

Conditions	Yield
With hydrogen at 150℃; under 60006 Torr; for 3h;	99%
With hydrogen; alumina substrate/0.05 wtpercent Ru at 140℃; under 150015 Torr; for 3.5h;	97%

di(2-ethylhexyl)terephthalate (6422-86-2) + butan-1-ol (71-36-3) → di-n-butyl terephthalate (1962-75-0) + 1-butyl 4-(2-ethylhexyl)terephthalate

Conditions	Yield
With titanium tetraisopropoxide at 160℃; for 4h; Reagent/catalyst; Temperature; Concentration; Inert atmosphere; Large scale;
at 160℃; for 2h; Inert atmosphere;
at 160℃; for 2h; Inert atmosphere;

2-propylheptan-1-ol (10042-59-8) + di(2-ethylhexyl)terephthalate (6422-86-2) → bis(2-propylheptyl)terephthalate

Conditions	Yield
With titanium tetraisopropoxide at 160℃; for 5h; Inert atmosphere;

di(2-ethylhexyl)terephthalate (6422-86-2) → 2-propylheptyl 2-ethylhexyl terephthalate

Conditions	Yield
Multi-step reaction with 2 steps 1: titanium tetraisopropoxide / 5 h / 160 °C / Inert atmosphere 2: titanium tetraisopropoxide / 5 h / 160 °C / Inert atmosphere View Scheme

di(2-ethylhexyl)terephthalate (6422-86-2) → di-n-butyl terephthalate (1962-75-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: titanium tetraisopropoxide / 5 h / 160 °C / Inert atmosphere 2: titanium tetraisopropoxide / 5 h / 160 °C / Inert atmosphere 3: titanium tetraisopropoxide / 4 h / 160 °C / Inert atmosphere; Large scale View Scheme

di(2-ethylhexyl)terephthalate (6422-86-2) → bis(2-propylheptyl)terephthalate

Conditions	Yield
Multi-step reaction with 3 steps 1: titanium tetraisopropoxide / 4 h / 160 °C / Inert atmosphere; Large scale 2: 5 h / 140 °C / Inert atmosphere 3: titanium tetraisopropoxide / 5 h / 160 °C / Inert atmosphere View Scheme

di(2-ethylhexyl)terephthalate (6422-86-2) → C24H44O4 + C24H44O4

Conditions	Yield
With hydrogen at 120℃; under 150015 Torr; for 12h; Reagent/catalyst;
With Rh/Al2O3; hydrogen at 155 - 165℃; under 112511 Torr; Temperature; Industrial scale; stereoselective reaction;

2-methyl-propan-1-ol (78-83-1) + di(2-ethylhexyl)terephthalate (6422-86-2) → diisobutyl terephthalate (18699-48-4) + isobutyl(2-ethylhexyl) terephthalate

Conditions	Yield
at 160℃; for 2h; Inert atmosphere;

di-n-butyl terephthalate (1962-75-0) + di(2-ethylhexyl)terephthalate (6422-86-2) + 1-butyl 4-(2-ethylhexyl)terephthalate → bis(2-ethylhexyl)cyclohexane-1,4-dicarboxylate (84731-70-4) + 1,4-DBCH + 1,4-BEHCH

Conditions	Yield
With hydrogen at 150℃; under 60006 Torr; for 3h;

di(2-ethylhexyl)terephthalate (6422-86-2) → 1,4-BEHCH

Conditions	Yield
Multi-step reaction with 2 steps 1: 2 h / 160 °C / Inert atmosphere 2: hydrogen / 3 h / 150 °C / 60006 Torr View Scheme

Upstream product

• 103-11-7 2-Ethylhexyl acrylate 
• 104-76-7 2-Ethylhexyl alcohol 
• 2430-22-0 7-methyl-1-octanol 
• 100-21-0 terephthalic acid 
• 1653-40-3 6-methylheptanol 
• 66793-83-7 7-methyloctan-2-ol 
• 10042-59-8 2-propylheptan-1-ol 
• 121-91-5 isophthalic acid 
• 120-61-6 1,4-benzenedicarboxylic acid dimethyl ester 
• 1962-75-0 di-n-butyl terephthalate 
• 71-36-3 butan-1-ol 

Downstream Products

• 1962-75-0 di-n-butyl terephthalate 
• 84731-70-4 bis(2-ethylhexyl)cyclohexane-1,4-dicarboxylate 
• 93158-39-5 1,4-DBCH 
• 18699-48-4 diisobutyl terephthalate 

Relevant articles and documents

Alcoholysis of polyethylene terephthalate to produce dioctyl terephthalate using choline chloride-based deep eutectic solvents as efficient catalysts

Dioctyl terephthalate (DOTP) is a new kind of green and non-toxic plasticizer. The traditional process to prepare DOTP is costly and complicated, thus it is very necessary to find an efficient and environmentally-friendly way to obtain DOTP. In this study, we prepared DOTP from the alcoholysis of polyethylene terephthalate (PET) by using 2-ethyl-1-hexanol (2-EH) as the solvent, and used choline chloride-based deep eutectic solvents (ChCl-based DESs) as the catalysts due to their cheapness, low toxicity and ease of preparation. Under the optimized conditions (ChCl/Zn(Ac)2 1:1, 5 wt%, 180 °C, 60 min, PET:2-EH 1:5 molar ratio), the conversion of PET and the yield of DOTP were 100% and 84.7%, respectively. Furthermore, the possible mechanism was proposed through density functional theory (DFT) calculations and experimental results. It revealed that the hydrogen bonds (H-bonds) formed between 2-EH and DESs played a key role in accelerating the degradation process. Furthermore, the kinetics of the reaction was also investigated, and the results indicated that the alcoholysis of PET is a first-order reaction with an activation energy of 95.05 kJ mol-1. This work confirmed that ChCl-based DESs are favorable for the degradation of PET to prepare DOTP under mild conditions, which can also be used for other polymer degradation strategies.

METHODS FOR MANUFACTURING AND DECOLORIZING DIOCTYL TEREPHTHALATE

A method for manufacturing and a method for decolorizing dioctyl terephthalate are provided. The decolorizing dioctyl terephthalate includes: providing an unpurified dioctyl terephthalate; mixing the unpurified dioctyl terephthalate with a reducing agent and an adsorption medium to obtain a first decolorizing product; and mixing the first decolorizing product with a decolorizing adsorbent material to obtain a second decolorizing product. The method for manufacturing dioctyl terephthalate includes: a transesterification step, an alkaline washing and neutralization step, a redox step, a decolorization step and a stripping step; the decolorizing adsorbent material has an acid value between 0.1 and 2 mg KOH/g, a relative humidity between 2 and 10%, and a fineness between 80 and 100 cm2 /g.

ESTER COMPOUNDS AND THEIR APPLICATION AS PLASTICISER

The present invention relates to a novel ester-based compound and a use thereof and, especially, to a use of a novel ester-based compound as a plasticizer to improve heat resistance and compatibility. The use of the ester-based compound according to the present invention as a plasticizer for a heat-resistant resin composition can contribute to the improvement in properties of a molded product by offering synergistic effects in the improvement of properties, such as migration resistance and a weight loss on heating, and can improve the processability of a heat-resistant resin composition through a fast absorption rate and a short melting time.