Method of making plasticizers

• US 5,434,294 A
• Filed: 04/04/1994
• Issued: 07/18/1995
• Est. Priority Date: 04/04/1994
• Status: Expired due to Term

• Current Assignee: BASF Corporation (BASF SE)
• Original Assignee: Aristech Chemical Corporation (Energy Transfer Operating, L.P.)
• Inventors: Smeal, Thomas W., Pugach, Joseph
• Primary Examiner(s): Acquah, Samuel A.
• Application Number:
  US08/223,399
• Time in Patent Office: 470 Days
• Field of Search: 528/275, 528/279, 528/296, 528/308, 528/489, 560/78, 560/98, 560/99
• US Class Current: 560/99
• CPC Class Codes: C07C 67/08 by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
• CPC Class Codes: C07C 69/76 Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 69/80 Phthalic acid esters

Abstract

A process for the titanate catalyzed preparation of plasticizers from polycarboxylic acids and alcohols which minimizes waste water and is energy efficient. The reaction product is treated with aqueous caustic and is then filtered using an absorbent medium which removes titanium, caustic, acid salts and water. The need for water washing is obviated, and the final plasticizer product has excellent properties.

Claims

1. Method of making an ester of a polycarboxylic acid whereby no appreciable amount of waste water is created, comprising (a) reacting said polycarboxylic acid or anhydride with an alkanol having 4-18 carbon atoms at a temperature of 180°

-250°

C. in the presence of an organic titanium-containing catalyst to obtain a plasticizer product having an acid number of no more than 0.1, (b) adding to said plasticizer product an aqueous alkaline solution at a temperature of about 80°

-150°

C., (c) passing said plasticizer product through an absorbent medium, thereby producing a permeate including said plasticizer product and alkanol and having reduced titanium and sodium contents, (d) stripping alkanol from said permeate, and (e) recovering said plasticizer product therefrom.

2. Method of claim 1 wherein the amount of aqueous alkaline solution added in step (b) is at least equivalent to the acid number of said polyesterified product.

3. Method of claim 1 wherein the aqueous alkaline solution added in step (b) is equivalent to about 1.3 to about 1.7 times the acid number of said polyesterified product.

4. Method of claim 1 wherein the aqueous alkaline solution comprises sodium hydroxide.

5. Method of claim 1 wherein the temperature in step (b) is about 90°

-110°

C.

6. Method of claim 1 wherein the absorbent medium is fuller'"'"'s earth.

7. Method of claim 1 wherein the absorbent medium is hydrotalcite.

8. Method of claim 1 wherein the absorbent medium is magnesium silicate.

9. Method of claim 6 wherein the fuller'"'"'s earth is used in an amount about 2-30 g fuller'"'"'s earth per kilogram of plasticizer product.

10. Method of claim 1 wherein the polycarboxylic acid or anhydride is phthalic anhydride.

11. Method of claim 1 wherein the alcohol is 2-ethylhexanol.

12. Method of claim 1 wherein the polycarboxylic acid or anhydride is trimellitic anhydride.

14. Method of claim 1 wherein said aqueous alkaline solution has a caustic concentration of 10-30 wt %.

13. Method of making an ester of a polycarboxylic acid comprising (a) reacting said polycarboxylic acid or anhydride with an alkanol having 4-18 carbon atoms at a temperature of 180°

-250°

C. in the presence of an organic titanium-containing catalyst to obtain a plasticizer product having an acid number of no more than 0.1, (b) adding to said plasticizer product an aqueous alkaline solution at a temperature of about 80°

-150°

C., (c) passing said plasticizer product through an absorbent medium selected from the group consisting of fuller'"'"'s earth, hydrotalcite, and magnesium silicate, thereby producing a permeate including said plasticizer product and alkanol and having reduced titanium, sodium and water contents, (d) stripping alkanol from said permeate, and (e) recovering said plasticizer product therefrom.