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CAS No. : | 6422-86-2 | MDL No. : | MFCD00072256 |
Formula : | C24H38O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RWPICVVBGZBXNA-UHFFFAOYSA-N |
M.W : | 390.56 | Pubchem ID : | 22932 |
Synonyms : |
|
Num. heavy atoms : | 28 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.67 |
Num. rotatable bonds : | 16 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 116.3 |
TPSA : | 52.6 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -3.39 cm/s |
Log Po/w (iLOGP) : | 5.24 |
Log Po/w (XLOGP3) : | 7.45 |
Log Po/w (WLOGP) : | 6.43 |
Log Po/w (MLOGP) : | 5.24 |
Log Po/w (SILICOS-IT) : | 6.98 |
Consensus Log Po/w : | 6.27 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 1.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -6.06 |
Solubility : | 0.000342 mg/ml ; 0.000000876 mol/l |
Class : | Poorly soluble |
Log S (Ali) : | -8.39 |
Solubility : | 0.0000016 mg/ml ; 0.0000000041 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -7.4 |
Solubility : | 0.0000156 mg/ml ; 0.0000000399 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 3.87 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With hydrogen at 150℃; for 3h; | 1.2 2) Hydrogenation 1,000 g of the composition resulting from the esterification and 20 g of ruthenium catalyst (NE CHEMCAT) were added as components to a 1.5 L high-pressure reaction vessel, and hydrogen was added at a pressure of 8 MPa to perform hydrogenation at 150° C. for 3 hours. And then complete the reaction. After the reaction, the catalyst was filtered and subjected to a conventional purification process to prepare a hydrogenated material with a yield of 99%. |
97% | With hydrogen at 140℃; for 3.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.5% | With phenol and titanium tetraisopropoxide resin at 200℃; for 4h; Dean-Stark; Inert atmosphere; | 4 Example 2 (comparative) . Preparing 2-ethylhexyl terephthalate (DOTP) in the presence of titanium SUBSTITUTE SHEET RULE 26 tetraisopropoxide General procedure: Example 2 (comparative) . Preparing 2-ethylhexyl terephthalate (DOTP) in the presence of titanium SUBSTITUTE SHEET RULE 26 tetraisopropoxideTerephthalic acid (TPA) (0.63 mol) and 2-ethylhexanol (1.44 mol) at a molar ratio of 1:2.3 are loaded to a 500 ml steel reaction vessel equipped with a heatable jacket, a steam control valve, and a Dean-Stark trap for distillation and separation of a water-alcohol azeotropic mixture. The mixture is heated to 200°C and then titanium tetraisopropoxide is added in an amount of 600 ppm per acid-alcohol mixture. The reaction is continued for 4 hours under stirring at a rate of 800 rpm, while passing through nitrogen gas at a rate of 0.05 L/min. During the reaction, the water-alcohol azeotropic mixture is distilled. The distilled alcohol is recycled into the reaction mixture. When the reaction is completed, the mixture is cooled and unreacted acid is filtered off. The yield of the reaction and the calculated efficiency of the process are given in Table 1. |
99% | With titanium isopropoxide at 170 - 200℃; Inert atmosphere; Large scale; | 1.1 1) Esterification 498.0 g of purified terephthalic acid (PTA), 1,170 g of 2-ethylhexanol (2-EH; PTA: 2-EH molar ratio (1.0): (3.0)) and as a catalyst 1.54gThe titanium catalyst (tetraisopropyl titanate (TIPT);0.31 parts by weight relative to 100 parts by weight of PTA) A 4-neck 3L reaction vessel equipped with a cooler, a condenser, a decanter, a reflux pump, a temperature controller, a stirrer, and the like was placed. The temperature was then slowly raised to about 170°C.At about 170°C, produce water,And the esterification is carried out for about 4.5 hours while continuously adding nitrogen at a reaction temperature of about 220°C under atmospheric pressure.Then terminate when the acid value reaches 0.01.After the reaction, distillation extraction is performed under reduced pressure for 0.5 to 4 hours to remove unreacted components. In order to remove the unreacted components to a predetermined content or less, steam extraction is performed using steam under reduced pressure for 0.5 to 3 hours, and neutralization is performed using an alkali solution after the reaction solution is cooled to about 90°C. . In addition, washing may be performed and then the reaction solution may be dehydrated to remove moisture. A filter media was placed in the dehydrated reaction solution, stirred for a predetermined time and then filtered to finally obtain 1,326.7 g of bis(2-ethylhexyl) terephthalate (DEHTP) (yield: 99.0%). |
99% | With titanium isopropoxide at 170 - 220℃; for 4.5h; Inert atmosphere; Large scale; | 1 Preparation Example 1: Preparation of DiethylhexylTerephthalate 10019] To a 4-neck 3 liter reactor provided with a cooler, a water stripper, a condenser, a decanter, a reflux pump, a temperature controller, a stirrer and the like, 498.4 g of purified terephthalic acid (PIA), 1172.1 g of ethylhexyl alcohol (LG Chem.) (molar ratio of terephthalic acid:ethylhexyl alcohol was 1:3), and 1.54 g of a titanium-based catalyst (TIPT, tetra isopropyl titanate) as a catalyst (0.3 parts by weight based on 100 parts by weight of the terephthalic acid) were added, and the temperature was slowly raised up to approximately 170° C. Water started to be generated near approximately 170° C., and an ester reaction was conducted for approximately 4.5 hours while continuously adding nitrogen gas at a reaction temperature of approximately 220° C. and under atmospheric pressure, and the reaction terminated when an acid value reached0.01.10020] After the reaction terminated, extractive distillationwas conducted for 0.5 hours to 4 hours under reduced pressure in order to remove unreacted raw materials. Neutralization was conducted using an alkali solution aftercooling the reaction solution. Afier that, moisture was removed by dehydrating the reaction solution. A filtermedium was added to the moisture-removed reaction solution, and the result was stirred for a certain period of time and then filtered to finally prepare 1162 g of di-(2-ethyl-.hexyl)terephthalate (yield: 99.0 /o). |
99.5% | With polystyrene-supported 1-methylene-3-butylimidazolium chlorostannate ionic liquid at 210℃; for 2.5h; | 4.2; 4.3 Example 4 2. Synthesis of DOTP In a 500 mL glass three-necked flask equipped with a stirring, thermometer, condenser, and water separator,Add 50g of terephthalic acid and 134mL of 2-ethylhexanol (PTA: 2-EH = 1:2.2) and 16gA polystyrene-supported butylimidazolium chloride stannous ionic liquid (10% of the sum of the mass of terephthalic acid and 2-ethylhexanol).The esterification synthesis reaction was carried out at 210 °C for 2.5 h, and the water formed by the reaction was continuously distilled off through a water separator. 3. Product separation and ion recoveryAfter the reaction is over, excess isooctanol is distilled off while hot. The temperature in the glass three-necked flask was lowered to 150 ° C. The solid catalyst and the liquid phase product are separated by filtration, and the acid value of the liquid phase product is 0.81 mgKOH/g.The yield of DOTP is 99.5%, and the catalyst can be directly used for recycling in the next synthesis reaction. |
99% | With titanium isopropoxide In lithium hydroxide monohydrate at 170 - 220℃; for 4.5h; Inert atmosphere; | 1 Preparation of bis(2-ethylhexyl) terephthalate (DEHTP) 498.0g purified terephthalic acid (TPA), 1,170g 2-ethylhexanol(2-EH; Ding Jie Ba: 2411 molar ratio = 1.0: 3.0), and 1.54g (0.31 weightParts, this is relative to 100 parts by weight of TPA) titanium catalyst (tetraisopropyl titanate(TIPT)) is added to equipped with cooler, condenser, decanter, return pump,Temperature controller, stirrer, etc. 4-neck 3L reaction flask, and then slowlyThe temperature of the reaction flask was increased to about 170°C.Start to generate at about 170°CWater, and under the continuous introduction of nitrogen, under atmospheric pressure and about 220°C reactionUnder the temperature, carry out esterification for about 4.5 hours, and stop the reaction when the acid value reaches 0.01should.After the reaction is complete, carry out distillation extraction under reduced pressure for 0.5 to 4 hoursTo remove unreacted raw materials.To make unreacted by removing unreacted raw materialsThe level of raw materials is reduced to a predetermined content level or lower, using steam under reduced pressureSteam extraction is performed for 0.5 to 3 hours.Cool the temperature of the reaction solution to about90°C, to neutralize with alkaline solution. In this case, you canTo be cleaned. After that, the reaction solution is dehydrated to remove water. Filter mediaThe material is introduced into the dehydrated reaction solution, stirred for a predetermined time and thenAfter filtration, 1,326.7 g of DEHTP was finally obtained (yield: 99.0%). |
96% | With methanesulfonic acid In lithium hydroxide monohydrate at 140 - 180℃; for 8h; Inert atmosphere; | 2 ExampleSynthesis of DOTP from Terephthalic Acid and 2-Ethylhexanol with MSA as Catalyst UnderReduced Pressure Terephthalic acid (249 g, 1.50 mol), 2-ethylhexanol (469 g, 3.60 mol), and methanesulfonic acid (Lutropur MSA, I3ASF, 6.13 g of an approximately 70% by weight aqueous solution, 0.04 5 mol) are used as initial charge in a 1.6 L double-walled stirred-tank reactor which can be heated by way of a programmable thermostat and has anchor stirrer, Jennewein water separator, condenser, nitrogen inlet, and connection for a vacuum pump, and the reactor is inertized with nitrogen. The nitrogen flow rate through the apparatus was set to from 2 to 4 L h-’, and the reaction mixture was heated to 180° C., whereupon an azeotropic mixture of water and 2-ethylhexanol was formed and liquefied in the condenser, and was passed through to the water separator. After phase separation, the organic phase was returned to the reactor, while the aqueous phase was discarded. The water removed was weighed and used to monitor the reaction. In order to ensure a constant flow of distillate and to achieve full conversion in the reaction, the temperature was increased within 4 h in stages to 200° C. and finally within a period of 2 h to 215° C. The temperature was kept at that level until the reaction mixture took the form of a clear solution and the calculated amount of water derived from the reaction and from the methanesulfonic acidusedhadbeen collected (56 g). The reaction time was 7.25 h. The reaction mixture was also studied by gas chromatography. Afier cooling to room temperature, the acid number of the mixture was determined by the known methods, and the mixture was rendered alkaline by using 150 mL of 1.2% NaOH (50% excess, based on the acid number determined). Afier the phases had been separated, the mixture was washed with water until neutral, and the excess 2-ethylhexanol, and also all of the other compounds with a boiling point below the boiling point of DOTP, were drawn off in vacuo (205° C., 8 mbar). The resultant product was filtered through a pressure-filter funnel. Reaction time: 7.25 h.Yield: 91%. GC content: 98.73% of DOTP (area %). Color value (APHA, Hazen): 12._10209] The reaction was carried out as described in inventive example 1. However, the pressure during the reaction was reduced from 750 mbar to 400 mbar, and the temperature was kept at from 140 to 180° C. Reaction time: 8 h. Yield: 96%. GC content: 97.27% of DOTP (area %). |
88.9% | at 180 - 260℃; for 10.5 - 21.5h; | EXAMPLES The process provided by the present invention is further illustrated by the following examples wherein all percentages given are by weight unless specified otherwise. A 500 milliliter autoclave was charged with 137.9 g (0.83 mole) TPA, 250 g (1.92 moles) EH and 125 ppm (0.048 g) TIPT catalyst. The autoclave was equipped with a stirrer, a conduit for feeding EH and nitrogen below the surface of the TPA/EH catalyst mixture, a pressure relief conduit and a conduit fitted with a control valve (backpressure regulator) for the removal of water and EH. The autoclave then was sealed and heated to approximately 180° C. to generate a pressure of 1 barg within the autoclave. As the reaction proceeded, a mixture of water and EH was removed and the EH was pumped back to the autoclave. Nitrogen was fed with the recycled EH to facilitate removal of water. Total reaction time was 10.5 hours at a maximum temperature of 260° C. and a maximum autoclave pressure of approximately 3 barg. Unreacted TPA (14 g) was recovered by filtration. The crude product then was neutralized with 2.5% aqueous NaOH, washed with water and filtered. Excess EH was stripped off at reduced pressure and the residue then steam stripped. The stripped product was treated with activated carbon at 90° C. for one hour then filtered through a filter aid to give 136.6 g of product (80% conversion). Analysis (Gas Chromatography, area percentages): 0.04% EH; 0.07% di-(2-ethylhexyl) phthalate, 0.13% methyl (2-ethylhexyl) terephthalate; 0.02% unknown; 99.42% DOTP. Color (PCS): 20. A comparative experiment was performed at atmospheric pressure. To a 2-liter, round-bottom flask equipped with overhead stirrer, thermometer, heating mantel and vapor decanter was added 350 g (2.107 mol) of TPA, 687 g (5.28 mol) of EH and 0.208 g (200 ppm) of TIPT. Upon heating, the reaction began at 180° C. The temperature slowly reached 189° C. in 6 hours. A temperature of 202° C. was achieved after 10 hours reaction time. The temperature was held at about 205° C. until 14 hours of reaction time were completed. The temperature then reached 210° C. at 15 hours, 222° C. at 18 hours and the final temperature was 230° C., where it was held for 2 hours. A reaction time of 21.5 hours was therefore required before water evolution slowed to the point that the reaction was discontinued. A total of 73.5 g of water-containing distillate was collected out of a theoretical amount of 75.8 g. The crude product was stripped of volatiles, giving a total of 125.3 g. The residue weighed 733.7 g for a yield of 88.9%. Analysis (Gas Chromatography, area percentages): 0.04% EH; 0.04% di-(2-ethylhexyl) phthalate, 0.36% DOTP Isomer; 99.39% DOTP. Color (PCS): 40. |
86% | With titanium(IV) oxide acetyl acetonate at 170 - 210℃; for 24h; Dean-Stark; | 1; 2 Example 1. Esterification of terephthalic acid (TPA) with 2-ethylhexanol (2-EH) The following general procedure was used. To a four-neck round bottom flask equipped with a mechanical/magnetic stirrer, Dean-Stark apparatus, and a thermometer pocket for monitoring internal temperature, 100 g TPA and 3.5 equivalents (eq) of 2-EH were added with agitation. The mixture was heated over an oil bath with a set temperature of 210°C. The titanium catalyst was added when the internal temperature was 170 °C. The quantity of catalyst varied from 0.11 mol% to 0.22 mol% with respect to TPA. After catalyst addition, slow formation of water was observed. The water formed during the reaction was collected in the Dean-Stark apparatus and drained out from time to time from the layer-separated mixture of water and 2-EH. The reaction was continued for 24 hours and then filtered. Conversion of TPA was determined by filtering the solids (unreacted TPA). HPLC was used to determine selectivity of the reaction. A comparative study using titanium tetraisopropoxide (Ti-1) versus titanium oxyacetylacetonate (Ti-2) was carried out using 0.22 mol% of catalyst using the conditions described above. When the reaction was carried out in the presence of Ti-1 the reaction provided a TPA conversion of 90% at 24 hours, a selectivity to formation of DOTP of 98.4% (Table 2), and 16 to 18 ml water was collected. In contrast, reaction in the presence of Ti-2 under the same conditions resulted in 98% conversion of TPA at 24 hours, a selectivity to DOTP of 99.5 %, and 20 to 21 ml water was collected. The filtrate of Example 1 was cooled to below 100°C and set for a distillation to remove excess 2-EH. After setting the vacuum at 7 to 8 mbar, the temperature of the reaction mixture was slowly raised in the following sequence: 130 to 150 to 200 to 210°C, to remove most of the 2-EH. The mixture cooled back to 90°C and 1 ml of aqueous caustic (NaOH) solution (49%, w/v) and 2 ml water were added to the mixture and stirred for 30 to 40 min. Excess caustic was neutralized by purging in-situ generated CO2 in the reaction mixture for 20 to 30 min. Then the mixture was again distilled to remove water and the rest of the 2-EH following the previous distillation method. The mixture was cooled to 120°C and filtered over lg CELITE (1 wt% on the basis of the weight TPA used in the reaction) to remove the white solid (residual sodium salt of TPA and carbonate salt and Titanium salt) resulting in a viscous liquid. The liquid was treated at 60 to 65 °C for 30 to 40 min with 1 g of acid-washed charcoal to remove colored impurities, followed by filtration over 1 g CELITE to obtain the final product, DOTP, which is colorless, viscous liquid. |
85% | With methanesulfonic acid In lithium hydroxide monohydrate at 180℃; for 4.5h; Inert atmosphere; | 1 Inventive Example 1 Synthesis of DOTP from Terephthalic Acid and 2-Ethylhexanol with MSA as Catalyst and 1-Ethyl-3-Methylimidazolium Methanesulfonate (Basionics AT 35) as Cosolvent Terephthalic acid (249 g, 1.50 mol), 2-ethylhexanol (469 g, 3.60 mol), and methanesulfonic acid (Lutropur MSA, BASF, 6.13 g of an approximately 70% by weight aqueous solution, 0.045 mol) and 1-ethyl-3-methylimidazolium methanesulfonate (Basionics ST 35, 55 g) are used as initial charge in a 1.6 L double-walled stirred-tank reactor which can be heated by way of a programmable thermostat and has anchor stirrer, Jennewein water separator, condenser, nitrogen inlet, and connection for a vacuum pump, and the reactor is inertized with nitrogen. The nitrogen flow rate through the apparatus was set to from 2 to 4 L h-1, and the reaction mixture was heated to 180° C., whereupon an azeotropic mixture of water and 2-ethylhexanol was formed and liquefied in the condenser, and was passed through to the water separator. After phase separation, the organic phase was returned to the reactor, while the aqueous phase was discarded. The water removed was weighed and used to monitor the reaction. In order to ensure a constant flow of distillate, the temperature was increased within 3 h in stages to 200° C. and finally within a period of 1.5 h to 224° C. Thereafter both phases of the reaction mixture were present in the form of clear solutions. After a reaction time of 4.5 h, the conversion, based on the amount of water removed, was 90%. The reaction mixture was also studied by gas chromatography. Here it was found, surprisingly, that <1% of the amount of 2-ethylhexanol used had been lost to side reactions. After cooling to 80° C., the phases were separated and the ionic fraction (63 g), which as well as the ionic liquid also contained the catalyst and the unreacted terephthalic acid, was separated off and kept for recycling. The phase containing DOTP and 2-ethylhexanol was washed with 1.8% NaOH (25 g) and water (200 mL), and then the excess 2-ethylhexanol, and also all of the other compounds with a boiling point below the boiling point of DOTP, were drawn off in vacuo (220° C., 5 mbar). The resultant product was filtered through a pressure-filter funnel. Reaction time: 4.5 h. Yield: 85%. GC content: 98.77% of DOTP (area %). Color value (APAH, Hazen): 30. |
1235 g | With Tyzor IAM at 230 - 250℃; for 3.8h; Inert atmosphere; Large scale; | 5 Example 5 Example 5 The same reactor as in Example 1 was used, but the filled distillation column was replaced by a 30 cm single column, and the catalyst was Tyzor IAM. 1333.2 g (10.24 mole) of 2-EH, 531.5 g (3.20 mole) of PTA, and 1.68 g (Ti=82 ppm) of Tyzor IAM were added to the reactor. The reactor was fully stirred in a nitrogen flow and pressurized to a gauge pressure of 4.0 kg/cm2, such that the temperature was allowed to increase to 230° C. in 0.8 hr. The water and alcohol mixture carried out by the nitrogen flow was passed through the filled distillation column and the condenser and then condensed in the oil-water separator. The upper alcohol mixture was directed back to the reactor via the return pipe so as to ensure the 2-EH/PTA of the reaction system be maintained at a fixed molar ratio of 3.2/1, and the lower water was continuously distilled off and removed from the oil-water separator for metering. The reaction was carried out for 0.5 hours and further heated to 250° C. to react for additional 2.7 hrs, and then the water was removed from the separator and metered as 114.5 ml (theoretical value 99.4%). The reactor was slowly depressurized to normal pressure, the temperature of the reaction system was 242° C., and 188 g of 2-EH were collected through the condenser. The acid value of the di-ester in the resultant crude reactants was 0.10 mg KOH/g, and the esterification lasted for 2.7 hrs in total. Next, the crude ester product was depressurized from 100 mmHg to a vacuum degree of <2 mmHg gradually to continuously distill off the unreacted alcohol at a distillation temperature of 180-190° C. After the vacuum degree reached <2 mmHg, the reaction lasted for 0.5 hrs, and was continued by filtering lasted for 6 min and 43 sec, thereby obtaining 1235 g of an odorless DOTP having a hue (platinum-cobalt) of 25 and an acid value of 0.08. |
With titanium isopropoxide; 2-(ethylamino)ethan-1-ol Heating; | Esterification of TPA with 2-EH Using Various Promoter Candidates This example used the reactor system and associated distillation column 30 shown in the FIGURE. The equipment included a one-liter base 31 fitted with a heating mantel 32, a magnetic stirrer bar 33, a temperature sensor 37, and a distillation column 34. The column 34 contained 10 inches of Penn State packing (which is equivalent to approximately 5 HETS). The top of the column 34 was fitted with a head 35 to allow the water/2-ethylhexanol azeotrope to condense via a condenser 39 and collect in a decanter 36. The top 2-ethylhexanol layer in the decanter 36 was returned to the column 34 via an overflow tube 38, and the water layer was collected in a collection device 40 and cooled in cooler 41 for weighing. [0028] The reactor column base 31 was charged with 343.48 g (2.637 moles, 25 mole % excess, MW=130.23) of 2-ethylhexanol, 1.054 mole (175 g, MW=166.13) of purified terephthalic acid (PTA), 3000 ppm of promoter candidate (1.55 g) listed in Table 1, and 3000 ppm (1.55 g) of tetraisopropoxy titanate (TIPT). In the case of promoter candidate DEA Titanate, 6000 ppm was used since it is thought to be a roughly 1:1 complex of organo-titanium and diethanol amine. [0029] The decanter was charged with 36.6 g of 2-ethylhexanol to make up for the removal of the 25 mole % excess from the system. [0030] Heat-up was started, and the reaction progress was monitored by the production of water. The total water removed was typically 40-42 g. A 98.5% recovery of materials was typically achieved. Table 1 shows the promoter candidates tested and the total reaction time to achieve completion for each candidate. | |
With titanium catalyst at 180 - 220℃; Inert atmosphere; | 1 Example 1, which is an embodiment of the plasticizer composition of this disclosure, is prepared in a reactor having a vent and a water removal column mounted to the reactor. The vent has an open and closed position. When the vent is in the open position (i.e., the vent is open), pressure is not formed in the reactor. As such, the reactor is maintained at atmospheric pressure. 2-ethylhexanol is pumped into the reactor and agitated. Terephthalic acid, in the form of a solid, is added to the reactor. No components other than 2-ethylhexanol and terephthalic acid are added to the reactor. The reactor is heated to approximately 180 °C using natural gas burners located beneath the reactor and with 8 bar steam through an internal heating coil in the reactor. The vent on the reactor is in the open position prior to the heating of the reactor. The vent continues to stay in the open position as the reactor is heated to 180 °C. The vent, while in the open position, prevents any pressure from forming in the reactor such that the reactor operates at atmospheric pressure. No measurable amount of reaction occurs between the 2-ethylhexanol and the terephthalic acid while the reactor is heated to 180 °C. Once the reactor reaches 180 °C, the reaction between 2- ethylhexanol and terephthalic acid begins. The water is continuously removed from the reactor through the water removal tower. (0104) [00104] After the reaction reaches 180 °C, a titanium catalyst is added and the vent is closed. After the vent is closed, nitrogen gas is continuously pumped into the reactor to increase the reaction pressure from 1 atm (atmospheric pressure) to 1.4 atm. The process of pumping nitrogen gas into the reactor lasts for the duration of the reaction. The reaction pressure is maintained at 1.4 atm. After the catalyst is added and the pressure reaches 1.4 atm, the temperature in the reactor is increased from 180 °C to 220 °C. A vacuum is introduced (i.e., pulled) to prevent any pressure over 1.4 atm. (0105) [00105] As the 2-ethylhexanol and terephthalic acid reaction proceeds, water is continuously removed from the reactor. As the reaction nears completion, the vacuum is increased to lower the reaction pressure to 0.4 atm to form the plasticizer composition. (0106) [00106] The plasticizer composition has an acid number that is less than 0.07 mg KOH. The plasticizer composition is then washed with an aqueous solution of sodium hydroxide, distilled, and filtered. | |
1235g | With TyzorIAM In lithium hydroxide monohydrate at 230 - 250℃; for 4h; Autoclave; Inert atmosphere; | 5 Example 5 The reactor was used as in Example 1, but instead of a 30 cm single tube, the fractionation column was packed and the catalyst was TyzorIAM. 1333.2 g (10.24 mole) of 2-EH, 531.5 g (3.20 mole) of PTA, 1.68 g (Ti = 82 ppm)Of the TyzorTE into the reactor. The reaction vessel was stirred well under a nitrogen stream and pressurized to a gauge pressureAnd the temperature was raised to 230 ° C over a period of 0.8 hours. The mixture of water and alcohol was purged with a nitrogen streamThe single-tube and condenser are then condensed in an oil-water separator, and the upper alcohol mixture is returned to the reactor from the reflux tube to ensure2-EH / PTA was maintained at a fixed molar ratio of 3.2 / 1, and the lower water was continuously distilled off from the oil-water separator.The reaction was continued for 0.5 hour and then the temperature was raised to 250 ° C. After 2.7 hours, the water was removed from the separator,Ml (theoretical value of 99.4%), began to slowly pressure to atmospheric pressure, reaction temperature of 242 and by the condenser to collect188 g of 2-EH, which was measured as the acid value of the crude ester of the reaction was 0.10 mg KOH / g, and the esterification reaction lasted 2.7hour. Next, the crude ester was depressurized and gradually reduced in pressure from 100 mm Hg to a vacuum <2 mm HgAnd the distillation temperature at 180-190 ° C under the conditions of continuous distillation of excess alcohol, the reaction in the vacuum to reach <2 mm Hg0.5 hours after the decompression, filtration, filtration time of 6 minutes and 43 seconds to get 1235g of DOTP, itsHue (platinum-cobalt) 35, the acid value of 0.08 odorless products. |
370 g | With titanium(IV) n-propoxide at 230℃; for 30h; Inert atmosphere; | 2 General procedure: Terephthalic acid (166 g, 1.0 mol) and 2-ethylhexanol (312 g, 2.4 mol) were placed in a pressurized reaction vessel having a capacity of 3 L equipped with a condenser and a decanter, and after substituting reduced pressure nitrogen, tetrapropyl titanate 0.1 wt% based on the weight of the reaction mixture) was charged as a reaction starting point, pressure rise was started so that the pressure became 0.1 MPa and the reaction temperature became 230 ° C. When the esterification rate reached 70%, the pressure reaction time was 15 hours. Thereafter, the pressure was restored to atmospheric pressure, and unreacted terephthalic acid was removed by filtration at 220 ° C. Subsequently, in order to complete the reaction, the reaction was carried out under normal pressure to reduced pressure condition while maintaining the temperature, and after the acid value reached 0.5 mg KOH / g, excessive amount of alcohol was removed by distillation under reduced pressure condition , The reaction was terminated when the hydroxyl value reached 0.5 mg KOH / g. After pressure reactionThe time from the completion of the reaction was 7 hours. The product yield (production volume) was 273 g, and the production amount (g / hour) per unit time was 12.4.Under the same conditions as in Example 1, when the pressure reaction was carried out until the esterification ratio reached 90%, the pressure reaction time was 30 hours, the time from the pressurization reaction to the reaction completion was 4 hours. The product yield (production amount) was 370 g, and the production amount per unit time was 10.9. |
With methanesulfonic acid at 210℃; for 19h; Dean-Stark; | 4 Esterification of terephthalic acid with 2-ethylhexanol was carried out in the presence of methanesulfonic acid (MSA), dodecyl benzene sulfonic acid (DBSA), para-toluene sulfonic acid (PTSA), or sulfuric acid (H2SO4), according to the chemical reaction shown below. (0038) (0039) As a comparison, an esterification reaction was also carried out using a titanium-containing catalyst. The reaction mixture was analyzed using high performance liquid chromatography (HPLC). [0029] Terephthalic acid (100 grams) and 2-ethylhexanol (3.5 molar equivalents relative to terephthalic acid) were added to a round bottom flask equipped with a mechanical/magnetic stirrer, a Dean-Stark apparatus, and a thermometer for monitoring internal temperature. The flask was placed in an oil bath set to 210°C, and the mixture was heated. The mixture remained as a heterogeneous mixture. The desired catalyst in an amount of 0.22 to 0.33 mole percent was added when the internal temperature reached 170°C. Immediately following catalyst addition, water formation was observed. Water formed during the reaction was collected in the Dean- Stark apparatus. The reactions were carried out for 24 hours. When methanesulfonic acid and sulfuric acid were used as catalysts, a homogenous reaction mixture was observed at 19 hours and 17 hours, respectively. In both of these cases, 100% conversion of terephthalic acid was achieved. In contrast, when a titanium-containing catalyst was used, 90% conversion was achieved after 24 hours. (0040) [0030] The reaction mixture was cooled to less than 100°C. A portion of the 2- ethylhexanol was removed by distillation under vacuum at 7-8 millibar while slowly raising the temperature to 210°C stepwise (130°C, 150°C, 200°C, 210°C). The mixture was then cooled again to 90°C, and 1-3 milliliter of an aqueous alkaline solution (49 wt% sodium hydroxide) was added based on the acid value of the reaction mixture. The mixture was stirred for 30 to 40 minutes and the carbon dioxide gas generated was purged for 20 to 30 minutes. The resulting mixture was further distilled to remove water and the remaining portion of the 2-ethylhexanol using the same distillation method as described previously. Following the second distillation, the mixture was cooled to 120°C and filtered over celite to remove solids. The liquid obtained was then treated with 1 gram of acid-washed activated charcoal, and then filtered over celite to provide pure diisooctyl terephthalate. The selectivity was 99.8%, the color of the diisooctyl terephthalate was 31, determined according to ASTM D1209, and the acid value was 0.04. The results obtained for each catalyst test are summarized in Table 1. As demonstrated by Comparative Example 1 , when the reaction was carried out using a titanium-containing catalyst, 90% conversion was only achieved after 24 hours, and the reaction mixture remained heterogeneous. Additionally, foaming was a critical problem for this reaction, which significantly hampers the water removal during the reaction. Examples 1 to 3 show that DBSA, PTSA, and MSA catalysts at a loading of 0.22 mole percent provide conversions of 97%, 68%, and 98.5%, respectively. The selectivity for each of these Examples was 98%, and the mixture further included 1 to 1.5% of the corresponding monoester. As shown by Examples 4 and 5, when the catalyst loading was increased to 0.33 mole percent, complete conversion of terephthalic acid was achieved in 19 hours for MSA, and 17 hours for H2SO4. The selectivity also improved to 99.8% and 99.5% for Examples 4 and 5, respectively. | |
With titanium isopropoxide at 180 - 225℃; for 2.5h; Inert atmosphere; | 1 [Example 1] As shown in Table 1, the PTA composition was first subdivided by a homogenizer. (1) 119 g of terephthalic acid (PTA) was mixed with 119 g of 2-EH, and then homogenized (the specification: 3000-6000 rpm, Horsepower: 50~60Hz) after 6 treatments,(2) Then take 192g of 2-EH to clean the slurry of the PTA residue of the homogenizer. The catalyst TIPT (tetraisopropyl titanate) is added in an amount of 0.6g, and then the slurry of (1) and (2) is added. After mixing and the catalyst are simultaneously fed into the four-necked flask,The reaction temperature was gradually increased from 180 ° C to 225 ° C under nitrogen, and the reaction time was 2.5 hours. The reaction pressure is 1013 mbar, and the water must be removed during the reaction.When the reaction is carried out to an acid value of 1 mgKOH/g or less,When neutralizing with an aqueous solution of an alkali metal hydroxide to a value of 0.07 mgKOH/g or less of the acid value of the synthesis reaction mixture, distillation is carried out to reduce the alcohol content to 300 ppm or less, followed by filtration purification. | |
at 95℃; | ||
Stage #1: 2-Ethylhexyl alcohol; terephthalic acid at 180℃; for 0.166667h; Stage #2: With 1-methyl-3-butylimidazole nitrate at 205℃; for 4.5h; | 1-5 Example 1 Add 100.00g terephthalic acid and 250.00g isooctyl alcohol into the reaction flask, heat and stir, raise to 180, maintain for 10min,Then add 1.00g 1-methyl-3-butylimidazole nitrate,During the reaction, the water generated by the reaction is continuously removed by a water separator to maintain the reflux of isooctyl alcohol. The reaction temperature was controlled at 205°C, and the reaction time was 4.5h. Anhydrous was formed. After the reaction solution was cooled to room temperature, 100 mL of cold water was added, the ionic liquid and the product were separated into two phases, and the product and the ionic liquid were separated. The product was poured into a flask, and the isooctanol was removed by vacuum distillation, the dealcoholization pressure was controlled to 500 Pa, and the dealcoholization was carried out at 160°C for 2.0 h. After the dealcoholization, add 3.5 g of activated clay, stir and decolorize at 100°C for 1.0 h, remove the activated clay by suction and filter, and obtain the product diisooctyl terephthalate. The test data are as follows: platinum cobalt color number: 20, acid value: 0.62mgKOH/g, ester content: 99.87%, open flash point: 206°C.Ionic liquid recycling: the recovered ionic liquid is rotary evaporated at 105°C for 1.0h, and then under 60kPa pressure, the temperature is controlled at 80°C and dried for 1.5h. The obtained ionic liquid is reused. | |
Heating; | Example The following examples are merely illustrative of the present invention and are not intended to limit the scope of the present invention. Terephthalic acid is selected as dicarboxylic acid and 2-ethylhexanol is selected as alcohol, and the amount of di(2-ethylhexyl) terephthalate produced in each case and consumed in heating the reactor by using aspen batch modeler, a simulation program that simulates chemical processes. The amount of steam produced was calculated. | |
With titanium tetra-n-butoxide; Butane-1,4-diol at 180 - 220℃; for 8h; Inert atmosphere; | 1 Example 1 In a 1L reactor equipped with a temperature sensor, a mechanical stirrer, a condenser, a decantor and a nitrogen injection device, 2-ethylhexanol(2-ethylhexanol) 320g, terephthalic acid 200g and 1,4-butanediol 22.5gThen, the temperature was raised to 180 degrees while stirring under nitrogen conditions. After the temperature was raised, 0.2 g of TNBT (Tetra N-butyl Titanate) was added.The esterification reaction was performed for 8 hours by heating to 220°C. When the reaction is complete, up to 90 degreesAfter cooling, an alkali solution (1M NaOH solution) was added and filtered using diatomaceous earth. Afterwards, the rotary evaporatorwas used to remove unreacted alcohol, water, and impurities, and the final product, an ester plasticizer composition, was obtained. | |
With titanium(IV) tetraisopropoxide at 225℃; for 6h; Inert atmosphere; | 1-4; 1-2 [Example 1] According to the formula in Table 1, take 120 g with terephthalic acid (PTA), 310 g with 2EH alcohol, 0.168 g with 911 alcohol (diluted with 2-EH), catalyst TIPT (tetraisopropyl titanate) Addition amount 0.6 g, feed terephthalic acid, 2EH alcohol, 911 alcohol mixture and catalyst into a four-necked flask at the same time. Under nitrogen, the reaction temperature is 225, the reaction time is 6 hours, and the reaction pressure is 5-1033 mbar. Moisture must be removed during the process. When the reaction reaches an acid value of 1 mgKOH/g or less, neutralize it with an aqueous solution of alkali metal hydroxide until the acid value of the synthesis reaction mixture is below 0.07 mgKOH/g, and then perform distillation to reduce the alcohol content. To less than 300 ppm, and then filter and purify, and makeLow migrationDi(2-ethylhexyl) phthalate is used as a plasticizer. | |
With titanium isopropoxide at 225℃; for 6h; Inert atmosphere; | 1-4; 1-2 [Example 1] According to the formula in Table 1, take 120 g with terephthalic acid (PTA), 310 g with 2EH alcohol, 0.168 g with 911 alcohol (diluted with 2-EH), catalyst TIPT (tetraisopropyl titanate) Addition amount 0.6 g, feed terephthalic acid, 2EH alcohol, 911 alcohol mixture and catalyst into a four-necked flask at the same time. Under nitrogen, the reaction temperature is 225, the reaction time is 6 hours, and the reaction pressure is 5-1033 mbar. Moisture must be removed during the process. When the reaction reaches an acid value of 1 mgKOH/g or less, neutralize it with an aqueous solution of alkali metal hydroxide until the acid value of the synthesis reaction mixture is below 0.07 mgKOH/g, and then perform distillation to reduce the alcohol content. To less than 300 ppm, and then filter and purify, and makeLow migration Di(2-ethylhexyl) phthalate is used as a plasticizer. | |
In lithium hydroxide monohydrate at 210℃; for 5.12h; | 1-2; 1-2 Example 1 Dioctyl terephthalate (DOTP), which is a diester, was prepared using the reaction system shown in FIG. 1 . Specifically, 2-ethylhexanol (7.5 mol) and terephthalic acid (3.0 mol) were supplied into the reactor 100 in which the catalyst was present, and the esterification reaction was performed while maintaining the temperature in the reactor 100 at 210 °C. At this time, the temperature in the reactor 100 was maintained by supplying high-pressure steam (HPS) in the reactor 100, and 2-ethylhexanol and water vaporized from the top of the reactor 100 were included. The top discharge stream passed through the column 400 through the gaseous discharge line 410 and then was condensed through the condenser 300 and supplied to the bed separator 200 . Thereafter, the mixed stream of 2-ethylhexanol and water supplied to the bed separator 200 is an alcohol layer 210 including 2-ethylhexanol in the bed separator 200, and a water layer comprising 220), the upper discharge stream of the bed separator 200 containing 2-ethylhexanol is refluxed to the top of the column 400, and the lower discharge stream containing water is discharged to the outside of the reaction system. removed. In the column 400 , the gaseous alcohol and water vaporized and discharged from the reactor 100 are refluxed from the upper part of the bed separator 100 to the upper part of the column 400 . The liquefied, mostly gaseous alcohol was selectively liquefied and refluxed to the reactor 100 through the reflux line 420 . In the process, the reflux of the overhead effluent stream comprising the alcohol to the reactor is initiated when the liquid level of the alcohol bed 210 in the bed separator reaches a set-point, the From the point in time when the conversion rate of the esterification reaction is 90%, the reflux ratio is linearly increased from 1 to 0 by constantly and gradually increasing the set value of the alcohol in the bed separator 200 using an actuator (Case in FIG. 1.) reduced. Thereafter, when the reflux ratio becomes 0, the pressure in the reactor is reduced to a vacuum state using the pump 500, and the total amount of residual alcohol in the reactor 100 is recovered with the bed separator 200, thereby terminating the reaction and A bottoms effluent stream comprising dioctyl terephthalate was obtained from reactor 100. At this time, the esterification reaction conversion rate, reaction time, and steam usage per batch (steam usage (100%) compared to steam usage in Comparative Example 2) at the time when the reflux ratio becomes 0 are shown in Table 1 below. |
Yield | Reaction Conditions | Operation in experiment |
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With titanium tetraisopropoxide at 160℃; for 4h; Inert atmosphere; Large scale; | 6 Example 6 1,000 g of DEHTP and 130 g of BuOH (13 parts by weight based on 100 parts by weight of the DEHTP) were introduced into a reactor equipped with a stirrer, a condenser, and a decanter, and transesterification reaction was conducted by adding a titanium-based catalyst (tetra isopropyl titanate, TIPT) in an amount (10.0 g) corresponding to 1.0 wt % of the introduced amount of DEHTP at a reaction temperature of 160° C. for 5 hours under a nitrogen atmosphere to obtain a reaction product including 64.5 wt % of DEHTP, 32.0 wt % of BEHTP, and 3.5 wt % of DBTP. [0100] A mixture distillation of the reaction product was conducted to remove butyl alcohol and 2-ethylhexyl alcohol and to prepare a final ester plasticizer. | |
at 160℃; for 2h; Inert atmosphere; | 1 Preparation of Mixture of DEBTP/BEHTP/DBTP 2000 g of di(2-ethylhexyl) terephthalate (manufactured by LG Chemical Co., Ltd.) and 340 g of n-butanol (17 parts by weight based on 100 parts by weight of DERTP) were charged into a reactor equipped with a stirrer, a condenser and a decanter, a transesterification reaction was carried out in a nitrogen atmosphere at a reaction temperature of 160° C. for 2 hours, and thereby a composition including dibutyl terephthalate (DBTP) at 4.0 wt %, butyl (2-ethylhexyl) terephthalate (BERTP) at 35.0 wt % and di(2-ethylhexyl) terephthalate (DERTP) at 61.0 wt % was prepared.10081] The reaction product was mixed and distilled to remove butanol and 2-ethylhexyl alcohol, and thereby a mixed composition was finally prepared. | |
at 160℃; for 2h; Inert atmosphere; | 1 Preparation Example 1: Preparation ofTerephthalate-Based Material To a reactor equipped with a stirrer, a condenser and a decanter, 2000 g of di(2-ethylhexyl) terephthalate (LG Chem,) and 340 g of n-butanol (17 parts by weight based on 100 parts by weight of DEHTP) were injected, and transesterification was carried out under a nitrogen atmosphere at a reaction temperature of 160° C. for 2 hours to obtain a composition including dibutyl terephthalate (DBTP), butyl (2-ethylhexyl) terephthalate (BEHTP) and di(2-ethylhexyl) terephthalate (DEHTP) in amounts of 4.0 wt %, 35.0 wt % and 61.0 wt %, respectively. The reaction product was distilled to remove butanol and 2-ethylhexyl alcohol to finally prepare a mixture composition. |
for 1.16667h; Autoclave; Reflux; Industrial scale; |
Yield | Reaction Conditions | Operation in experiment |
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With methanesulfonic acid at 210℃; for 4h; Inert atmosphere; | 4 General procedure: 498.4 g of purified terephthalic acid, 1015.8 g of ethylhexyl alcohol, 89 g of butyl alcohol, and 15 g (3 parts by weight based on 100 parts by weight of the PTA) of methanesulfonic acid (MSA) as a catalyst were put in a 3 liter, four-neck reactor equipped with a cooler, a water stripper, a condenser, a decanter, a reflux pump, a temperature controller, and a stirrer, and the temperature was slowly increased to about 210° C. The generation of water was initiated at about 170° C., and an esterification reaction was conducted for about 4 hours while continuously introducing nitrogen gas at a reaction temperature of about 210° C. under an atmospheric pressure condition. The reaction was terminated when an acid value reached 4.After the completion of the reaction, distillation extraction was performed for 0.5 hours to 4 hours under reduced pressure in order to remove unreacted raw materials. Steam extraction was performed for 0.5 hours to 3 hours under reduced pressure using steam in order to remove the unreacted raw materials below a predetermined amount level. A temperature of a reaction solution was cooled to about 90° C. to perform a neutralization treatment using an alkaline solution. In addition, washing may also be performed and thereafter, water was removed by dehydrating the reaction solution. Filter media were introduced into the dehydrated reaction solution and stirred for a predetermined time. Then, the solution was filtered to finally obtain 1 wt % of dibutyl terephthalate (DBTP), 15 wt % of 1-butyl 4-(2-ethylhexyl)terephthalate (BEHTP), and 84 wt % of di-(2-ethylhexyl)terephthalate (DEHTP). |
Yield | Reaction Conditions | Operation in experiment |
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With methanesulfonic acid at 210℃; for 4h; Inert atmosphere; | 3 Comparative Example 3 498.4 g of purified terephthalic acid, 1015.8 g of ethylhexyl alcohol, 89 g of butyl alcohol, and 15 g (3 parts by weight based on 100 parts by weight of the PTA) of methanesulfonic acid (MSA) as a catalyst were put in a 3 liter, four-neck reactor equipped with a cooler, a water stripper, a condenser, a decanter, a reflux pump, a temperature controller, and a stirrer, and the temperature was slowly increased to about 210° C. The generation of water was initiated at about 170° C., and an esterification reaction was conducted for about 4 hours while continuously introducing nitrogen gas at a reaction temperature of about 210° C. under an atmospheric pressure condition. The reaction was terminated when an acid value reached 4.After the completion of the reaction, distillation extraction was performed for 0.5 hours to 4 hours under reduced pressure in order to remove unreacted raw materials. Steam extraction was performed for 0.5 hours to 3 hours under reduced pressure using steam in order to remove the unreacted raw materials below a predetermined amount level. A temperature of a reaction solution was cooled to about 90° C. to perform a neutralization treatment using an alkaline solution. In addition, washing may also be performed and thereafter, water was removed by dehydrating the reaction solution. Filter media were introduced into the dehydrated reaction solution and stirred for a predetermined time. Then, the solution was filtered to finally obtain 1 wt % of dibutyl terephthalate (DBTP), 15 wt % of 1-butyl 4-(2-ethylhexyl)terephthalate (BEHTP), and 84 wt % of di-(2-ethylhexyl)terephthalate (DEHTP). |
Yield | Reaction Conditions | Operation in experiment |
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at 140℃; for 5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
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With titanium tetraisopropoxide at 160℃; for 5h; Inert atmosphere; | 12 Example 12 Transesterification reaction was conducted in the same manner as in Example 1, except that bis(2-propylheptyl)terephthalate was used instead of di-(2-ethylhexyl)terephthalate, 70 g of 2-ethyl hexanol (7 parts by weight based on 100 parts by weight of DEHTP) was used instead of 70 g of butanol, the reaction temperature in Example 1 was changed to 160° C., and a titanium-based catalyst (tetra isopropyl titanate, TIPT) was added in an amount (1.0 g) corresponding to 0.1 wt % of the added amount of DEHTP, to obtain a reaction product including 73 wt % of bis(2-propylheptyl)terephthalate, 25 wt % of 2-propylheptyl ethylhexyl terephthalate, and 2 wt % of DEHTP. The product was distilled by the same method to prepare a final ester plasticizer. |
Yield | Reaction Conditions | Operation in experiment |
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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 |
Yield | Reaction Conditions | Operation in experiment |
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With titanium tetraisopropoxide at 160℃; for 5h; Inert atmosphere; | 11 Example 11 Transesterification reaction was conducted in the same manner as in Example 1, except that 70 g of 2-propyl heptanol (7 parts by weight based on 100 parts by weight of DEHTP) was used instead of 70 g of butanol, the reaction temperature in Example 1 was changed to 160° C., and a titanium-based catalyst (tetra isopropyl titanate, TIPT) was added in an amount (1.0 g) corresponding to 0.1 wt % of the added amount of DEHTP, to obtain a reaction product including 74 wt % of DEHTP, 24 wt % of 2-propylheptyl octyl terephthalate, and 2 wt % of bis(2-propylheptyl)terephthalate. The product was distilled by the same method to prepare a final ester plasticizer. |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: titanium tetraisopropoxide / 5 h / 160 °C / Inert atmosphere 2: titanium tetraisopropoxide / 5 h / 160 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
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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 |
Yield | Reaction Conditions | Operation in experiment |
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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 |
Yield | Reaction Conditions | Operation in experiment |
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With titanium(IV) isopropylate; 2-(Ethylamino)ethanol for 1.4h; Heating; | 3 Example 2 was compared with an optimized dimethyl terephthalate run using the same reaction equipment. The following were charged to the flask: 364.6 g of 2-ethylhexanol (2.8 moles, 40 mole % excess, MW=130.23); 194.2 g of DMT (1 mole; MW=194.18); and 0.055 g of TIPT (98 ppm). [0037] A total of 1.4 hours reaction time resulted in removing 255 mL of methanol to completion of the reaction. Thus, the best reaction time achievable with terephthalic acid of 1.75 hours compares favorably with the 1.4 hours reaction time obtained with dimethyl terephthalate. |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogen at 120℃; for 12h; | 2.5 DOTP Ring Hydrogenation (Dioctyl Terephthalate) A 300 mL pressure reactor is initially charged with the catalyst A prepared according to Example 1.1. (7.5 g) in a catalyst insert basket, which is admixed with 150 g of dioctyl terephthalate. The hydrogenation was performed with pure hydrogen at a constant pressure of 200 bar and a temperature of 120° C. Hydrogenation is effected for 12 h. The reactor was subsequently decompressed. The conversion is 100%. (GC column: optimal, length 30 m, layer thickness 1 μm; temperature program: 50° C., 10 min, at 10° C./min to 300° C.) The selectivity for dioctyl 1,4-cyclohexanedicarboxylate is 97.7% as a mixture of the cis and trans isomers. | |
With Rh/Al2O3; hydrogen at 155 - 165℃; Industrial scale; stereoselective reaction; | 2 Example 1 Dioctyl terephthalate (DOTP) having purity of 99% was introduced into a reactor, and hydrogenation was conducted at a reaction pressure of 150 bar and a reaction temperature of 165 to 175° C. (0083) The mass flux of DOTP per unit area of the reactor (m2) was 20,000 kg/h, and hydrogen was introduced at a hydrogen/DOTP mole ratio of 6. (0084) The reactor was in the form of a single-lumen tube, the total length of a part filled with a catalyst in the tube was 3.0 m, and a cooling fluid (Therminol 55) was flowed to the external jacket of the reactor to control such that a temperature deviation of the reactor was maintained at 15 to 25° C. during the reaction (a temperature deviation per unit length at 5° C./m). In addition, the reaction amount per unit volume (m3) of the reactor during the reaction was set up as 30 kmol/h or less. (0085) The catalyst used in the reactor was a ruthenium (Ru) catalyst having a ruthenium content of 0.5 wt %, based on 100 wt % of an alumina (Al2O3) carrier, and a cylinder type of catalyst having a diameter of 3 mm and a height of 3 mm was used. |
Yield | Reaction Conditions | Operation in experiment |
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With titanium(IV) tetraethanolate at 220℃; for 5h; Inert atmosphere; | 1 preparation example 1 one pot preparation [0059] 1.8 g of tetraisopropyl titanate as a reaction catalyst was added to a reactant, in which 1.5 mol terephthalicacid, 1.5 mol isophthalic acid, and 9.0 mol 2-ethylhexanol were mixed in a five-neck round flask equipped with a temperaturesensor, a mechanical stirrer, a condenser, a decanter, and a nitrogen injection apparatus, and the reaction wasperformed for 5 hours while increasing temperature to 220°C.[0060] After the reaction, an excessive amount of alcohol was extracted under reduced pressure, and neutralizationand washing processes were performed using soda ash and distilled water. Then, dehydration and filtration were carriedout by vacuum distillation.[0061] As a result of analyzing the obtained composition with a GC-Mass analyzer, it was identified that the compositionwas formed of compounds respectively having the following Chemical Formulae 1 and 2 and a weight ratio was 50:50.[0062] The same process was repeated except that a reactant, in which 2.1 mol terephthalic acid, 0.9 mol isophthalicacid, and 9.0 mol 2-ethylhexanol were mixed, was used in Preparation Example 1.[0063] As a result of analyzing the obtained plasticizer with a GC-Mass analyzer, it was identified that the plasticizerincluded the compounds respectively having Chemical Formulae 2 and 1, which were suggested in Preparation Example1, at a weight ratio of 70:30 (Chemical Formula 2:Chemical Formula 1).[0064] The same process was repeated except that a reactant, in which 3.0 mol isophthalic acid and 9.0 mol 2-ethylhexanol were mixed while not using terephthalic acid, was used in Preparation Example 1.[0065] As a result of analyzing the obtained plasticizer with a GC-Mass analyzer, it was identified that the plasticizerwas a compound having Chemical Formula 1 which was suggested in Preparation Example 1.[0066] |
Yield | Reaction Conditions | Operation in experiment |
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With titanium(IV) isopropylate at 235℃; for 4h; Inert atmosphere; | 1 A 5-neck round flask equipped with a temperature sensor, a mechanical stirrer, a condenser, a decanter and a nitrogen inlet was charged with 2.65 mol of terephthalic acid, 1.59 mol of 2-ethylhexanol and 6.36 mol of 2-propylheptanol 0.0056 mol of tetraisopropyl titanate was added as a reaction catalyst and the reaction was carried out at 235 ° C for 4 hours.After the reaction, the excess alcohol was extracted under reduced pressure, neutralized with sodium sulphate and distilled water, dehydrated under reduced pressure distillation, and passed through a filter to obtain an ester plasticizer composition as the plasticizer composition of the present invention.The obtained plasticizer was analyzed by a GC-Mass analyzer. As a result, it was confirmed that the compound was composed of the compound having the formula (1), (2), and (3), and that the weight ratio was 25: 2: 73. |
Yield | Reaction Conditions | Operation in experiment |
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1: 54 %Chromat. 2: 36 %Chromat. 3: 10 %Chromat. | With titanium(IV) isopropylate at 220℃; for 9h; | 4 Comparative Example 4 In Example 1, 2.65 mol of terephthalic acid, 5.29 mol of 2-ethylhexanol and 5.29 mol of 2-isononyl alcohol were reacted at a temperature of 220 for 9 hours under 0.056 mol of tetraisopropyl titanate, Alcohol was extracted and removed.Neutralized by using soda ash, rinsed once with water, and then dehydrated by heating under reduced pressure. Then, the filter material was charged and filtered to obtain a plasticizer composition.The obtained plasticizer was analyzed by a GC-Mass analyzer. As a result, it was confirmed that 10% of diethylhexyl terephthalate, 54% of ethylhexyl isononyl terephthalate, and 36% of diisononyl terephthalate. |
Yield | Reaction Conditions | Operation in experiment |
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With titanium(IV) isopropylate; monobutyltin triisooctanoate at 150 - 230℃; for 2h; | 2 Ingredients: terephthalic acid, iso-octanol, tetrabutyl titanate, monobutyltin triisooctanoate tin; Submit CorrectionsCloseThe amount of alcohol to acid ratio 2.81 of isooctyl alcohol and terephthalic acid into the reactor and heated to 150 ° C dehydration, then add accounting terephthalic 0.15% wt of tetrabutyl titanate and 0.1% wt monobutyl tin triisooctanoate heating and stirring continuously out of the system during the reaction generated water, iso-octanol reflux. 2.81150°C0.15%wt0.1%wt Submit CorrectionsCloseRaising the temperature to 230 ° C, the reaction took 2 hours, when the reaction to the acid value |
Yield | Reaction Conditions | Operation in experiment |
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at 160℃; for 2h; Inert atmosphere; | 1 Example 1 To a reactor provided with a stirrer, a condenser and a decanter, 2000 g of di-(2-ethylhexyl)terephthalate obtained in Preparation Example 1 and 320 g of isobutanol (16 parts by weight based on 100 parts by weight of the DEHTP) were added, and then the result was conducted transesterification for 2 hours at a reaction temperature of 160° C. under nitrogen atmosphere to prepare an ester-based plasticizer composition comprising 5.6% by weight of diisobutyl terephthalate (DiI3TP), 37.3% by weight of isobutyl(2-ethylhexyl)terephthalate (i-I3EHTP or i-I3OTP) and 57.1% by weight of di-(2-ethylhexyl)terephthalate (DEHTP or DOTP). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen at 150℃; for 3h; | 3 Preparation of Rydrogenated Mixture ofDERTP/BERTP/DBTP 1000 g of the composition prepared in Preparation Example 1 as a raw material and 20 g of a ruthenium catalyst (N.E CREMCAT) were charged in a 1.5 L high-pressure reactor, hydrogen was added to a pressure of 8 MPa andhydrogenation reaction was carried out at a temperature150° C. for 3 hours to complete the reaction. Afier completion of the reaction, the catalyst was filtered, and a mixed composition hydrogenated in a yield of 99% was prepared through a conventional purification process. Finally, a composition including di(2-ethylhexyl) cyclohexane 1 ,4-diester (1,4-DERCR) at 55 wt %, butyl di(2-ethylhexyl) 1,4-cyclo- hexane diester (1 ,4-BERCR) at 38 wt %, and dibutyl 1 ,4-cyclohexanediester (1 ,4-DBCR) at 7 wt % was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 2 h / 160 °C / Inert atmosphere 2: hydrogen / 3 h / 150 °C / 60006 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With titanium(IV) isopropylate at 170 - 220℃; for 4.5h; Inert atmosphere; | 2 Preparation of Mixture of DINTP/ERINTP/DERTP 498.0 g of purified terephthalic acid (PTA), 819 g of 2-ethylhexyl alcohol (2-ER) (the molar ratio of PTA:2- ER=1.0:2.1), 389 g of isononyl alcohol (INA)(the molar ratio of PTA:INA=1 .0:0.9), and 1.54 g of a titanium-based catalyst (TIPT, tetra isopropyl titanate) (0.31 parts by weight based on 100 parts by weight of PTA) as a catalyst were added to a 3-liter four-neck reactor equipped with a cooler, a condenser, a decanter, a reflux pump, a temperature controller, a stirrer and the like, and a temperature was slowly raised to about 170° C. The generation of water was initiated at about 170° C., and an esterification reaction was conducted for about 4.5 hours while continuously introducing nitrogen gas at a reaction temperature of about 220° C. under atmospheric pressure. The reaction was terminated when an acid value reached 0.01. After the completion of the reaction, distillation extraction was performed for 0.5 hours to 4 hours under reduced pressure in order to remove unreacted raw materials. Steam extraction was performed for 0.5 to 3 hours under reduced pressure using steam in order to remove the unreacted raw materials to below a predetermined content level. A temperature of a reaction solution was cooled to about 90° C. to perform a neutralization treatment using an alkaline solution. In addition, washing may be further performed and then water was removed by dehydrating the reaction solution. Filter media were introduced into the dehydrated reaction solution and stirred for a predetermined time. Then, the solution was filtered to finally obtain a composition including diisononyl terephthalate (DINTP) at 6 wt %, (2-ethylhexyl) isononyl terephthalate (ERINTP) at 30 wt % and di(2-ethylhexyl) terephthalate (DERTP) at 64 wt %. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84.2% | With choline chloride; zinc diacetate at 185℃; for 1h; Green chemistry; | |
With titanium(IV) isopropylate at 180 - 225℃; for 5h; Inert atmosphere; | 1 [Embodiment 1] Preparation of Dioctyl Terephthalate 400 g of recycled polyethylene terephthalate is mixed with 700 g of 2-ethylhexanol, and added with 0.71 g of catalyst tetraisopropyl titanate (TIPT), where the nitrogen reaction will gradually increase in temperature from 180° C. to 225° C. The reaction time is 2.5 hours, the reaction pressure is 1013 mbar for 1.5 hours, then -30 mbar for 1 hour to obtain the slurry of dioctyl terephthalate. After the reaction, the acid value of the slurry of dioctyl terephthalate is 1 mg KOH/g, and is neutralized with alkali hydroxides solution to the acid value less than 0 07 mg KOH/g. Then, distillation is performed to reduce the alcohol content to below 300 ppm. After the reaction, the colorimetry of the dioctyl terephthalate is 200, and the colorimetry after the alkaline washing and neutralization step is 105. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 2-Ethylhexyl acrylate; C13H24O3 With sulfuric acid; hydroquinone In N,N-dimethyl-formamide at 150℃; for 12h; Sealed tube; Stage #2: With palladium on activated charcoal In ethyl acetate at 240℃; for 12h; Inert atmosphere; |
Tags: 6422-86-2 synthesis path| 6422-86-2 SDS| 6422-86-2 COA| 6422-86-2 purity| 6422-86-2 application| 6422-86-2 NMR| 6422-86-2 COA| 6422-86-2 structure
[ 63468-13-3 ]
2-Ethylhexyl methyl terephthalate
Similarity: 1.00
[ 155603-50-2 ]
4-(((2-Ethylhexyl)oxy)carbonyl)benzoic acid
Similarity: 1.00
[ 63468-13-3 ]
2-Ethylhexyl methyl terephthalate
Similarity: 1.00
[ 155603-50-2 ]
4-(((2-Ethylhexyl)oxy)carbonyl)benzoic acid
Similarity: 1.00
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