Plasticizer composition comprising di(2-ethylhexyl) terephthalate

Patent metadata

Field	Value
Publication number	US-9309183-B2
Application number	US-201414184853-A
Country	US
Kind code	B2
Filing date	Feb 20, 2014
Priority date	Feb 20, 2014
Publication date	Apr 12, 2016
Grant date	Apr 12, 2016

Abstract

A plasticizer composition is disclosed that includes di(2-ethylhexyl) terephthalate, and which is substantially free of a di-ester according to Formula I:

where R 1 is a straight-chain or branched alkyl group having from 1 to 13 carbon atoms, and where R 1 is different than 2-ethylhexane. The plasticizer composition may be used in a plastisol composition, a powder coating composition, a molding composition, and various other compositions. A method of preparing an aromatic di-ester is also disclosed. The method may prepare the plasticizer composition.

First claim

The invention claimed is:

1. A plasticizer composition comprising di(2-ethylhexyl) terephthalate and which is substantially free of a di-ester according to Formula I:

wherein R1 is a straight-chain or branched alkyl group having from 1 to 13 carbon atoms;
wherein R1 is different than 2-ethylhexane; and
wherein said di(2-ethylhexyl) terephthalate is present in an amount greater than or equal to 99.9 parts by weight based on 100 parts by weight of said plasticizer composition and said di-ester according to Formula I is present in an amount less than 0.1 parts by weight based on 100 parts by weight of said plasticizer composition.

2. The plasticizer composition as set forth in claim 1 wherein said di(2-ethylhexyl) terephthalate is present in an amount greater than or equal to 99.95 parts by weight based on 100 parts by weight of said plasticizer composition, and said di-ester according to Formula I is present in an amount less than 0.05 parts by weight based on 100 parts by weight of said plasticizer composition.

3. The plasticizer composition as set forth in claim 2 wherein said di(2-ethylhexyl) terephthalate is present in an amount greater than or equal to 99.97 parts by weight based on 100 parts by weight of said plasticizer composition, and said di-ester according to Formula I is present in an amount less than 0.03 parts by weight based on 100 parts by weight of said plasticizer composition.

4. The plasticizer composition as set forth in claim 1 wherein said di-ester according to Formula I comprises methyl (2-ethylhexyl) terephthalate.

5. The plasticizer composition as set forth in claim 1 wherein said plasticizer composition is also substantially free of the reaction product of:
i. terephthalic acid; and
ii. decomposition products of 2-ethylhexanol, decomposition products of a titanium catalysts, or combinations thereof.

6. The plasticizer composition as set forth in claim 5 wherein said plasticizer composition is also substantially free of di(methyl) terephthalate.

7. The plasticizer composition as set forth in claim 1 wherein said plasticizer composition further comprises one or more ester that is different from said di(2-ethylhexyl) terephthalate; and said one or more ester is selected from a group consisting of cyclohexanedicarboxylic acid esters, phthalic acid dialkyl esters, phthalic acid alkylaralkyl esters, terephthalic acid dialkyl esters different from said di-ester in accordance with Formula I and said di(methyl) terephthalate, trimellitic acid trialkyl esters, adipic acid dialkyl esters, benzoic acid alkyl esters, dibenzoic acid esters of glycols, hydroxybenzoic acid esters, esters of saturated monocarboxylic acids and dicarboxylic acids, esters of unsaturated dicarboxylic acids, amides and esters of aromatic sulfonic acids, alkylsulfonic acid esters, glycerol esters, isosorbide esters, phosphoric acid esters, citric acid triesters, alkylpyrrolidone derivatives, 2,5-furandicarboxylic acid esters, 2,5-tetrahydrofurandicarboxylic acid esters, epoxidized vegetable oils based on triglycerides and saturated or unsaturated fatty acids, and polyesters of aliphatic and aromatic polycarboxylic acids with polyhydric alcohols.

8. A plastisol composition comprising said plasticizer composition as set forth in claim 1 .

9. A powder coating composition comprising said plasticizer composition as set forth in claim 1 .

10. An extrusion aid composition, a calendaring agent composition, a rheology modifier composition, a surface-active composition, a melt flow enhancer composition, a film-forming agent composition, a defoamer composition, an antifoamer composition, a wetting agent composition, a coalescing agent composition, an emulsifier composition, a lubricant composition, a lubricating oil composition, a lubricating grease composition, a quenchers for a chemical reaction, a phlegmatizer composition, a pharmaceutical composition, an adhesive composition, an impact modifier composition, an extender composition, or a heat transfer oil composition comprising said plasticizer composition as set forth in claim 1 .

11. A plasticizer composition comprising;
di(2-ethylhexyl) terephthalate present in an amount greater than or equal to 99.9 parts by weight based on 100 parts by weight of said plasticizer composition;
wherein said plasticizer composition comprises less than a combined total of 0.1 parts by weight based on 100 parts by weight of said plasticizer composition, of the following:
i. a di-ester according to Formula I:

wherein R 1 is a straight chain or branched alkyl group having from 1 to 13 carbon atoms, and
wherein R 1 is different than 2-ethylhexane;

ii. the reaction product of:
a. terephthalic acid, and
b. decomposition products of 2-ethylhexanol, decomposition products of a titanium catalyst, or combinations thereof; and

iii. di(methyl) terephthalate.

12. A plasticizer composition comprising di(2-ethylhexyl) terephthalate which is substantially free of a di-ester according to Formula I:

R 1 is a straight-chain or branched alkyl group having from 1 to 13 carbon atoms and R 1 is different than 2-ethylhexane;
wherein said plasticizer composition is prepared by a method comprising the steps of:
combining terephthalic acid and 2-ethylhexanol to firm a mixture;
heating the mixture from a first temperature (T1) to a second temperature (T2) without a catalyst present in the mixture;
combining a titanium catalyst with the mixture after the mixture is at the second temperature (T2);
increasing pressure from a first pressure (P1) to a second pressure (P2) after the mixture is at the second temperature (T2); and
increasing the temperature of the mixture from the second temperature (T2) to a third temperature (T3) while maintaining the second pressure (P2);

wherein said di(2-ethylhexyl) terephthalate is present in an amount greater than or equal to 99.9 parts by weight based on 100 parts by weight of said plasticizer composition and said di-ester according to Formula I is present in an amount less than 0.1 parts by weight based on 100 parts by weight of said plasticizer composition.

13. The plasticizer composition as set forth in claim 12 wherein the second temperature (T2) is from about 175 to about 185° C.

14. The plasticizer composition as set forth in claim 13 wherein the third temperature (T3) is from about 210 to about 240° C.

15. The plasticizer composition as set forth in claim 12 wherein the method further comprises the step of preventing pressure from increasing from the first pressure (P1) as the temperature is increased from the first temperature (T1) to the second temperature (T2).

16. The plasticizer composition as set forth in claim 12 wherein the first pressure (P1) is about atmospheric pressure.

17. The plasticizer composition as set forth in claim 16 wherein the second pressure (P2) is from about 11.3 to about 1.6 atm.

18. The plasticizer composition as set forth in claim 12 wherein the method further comprises:
adding the aqueous solution of sodium hydroxide to neutralize any remaining carboxylic acid groups on the terephthalic acid and form a salt with the titanium catal

Assignees

• Basf Se
• Basf Corp

Inventors

• Storzum Uwe
• Breitscheidel Boris
• Todd Kevin Scott
• Veinot Jason David

Classifications

• C07C67/08 Primary

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title

• C08K5/12

  of cyclic polycarboxylic acids · CPC title

• C07C69/82

  Terephthalic acid esters · CPC title