High purity dibasic acid compositions and methods of making the same

Patent metadata

Field	Value
Publication number	US-9487463-B2
Application number	US-201414502382-A
Country	US
Kind code	B2
Filing date	Sep 30, 2014
Priority date	Oct 8, 2013
Publication date	Nov 8, 2016
Grant date	Nov 8, 2016

Abstract

High-purity dibasic acid compositions are generally disclosed. In some embodiments, the dibasic acid compositions are solutions or suspensions. In some other embodiments, the compositions are solid-state compositions. In some such embodiments, the solid-state compositions include a dibasic acid as a crystalline solid and further include a low quantity of certain impurities, such as monobasic acids, various esters, and the like. Methods and systems for making such high-purity dibasic acid compositions are also disclosed.

First claim

What is claimed is:

1. A method for hydrolyzing a dibasic ester, comprising:
introducing a dibasic ester to a reactor, where the dibasic ester is 1,18 dimethyl octadecanedioate; and
reacting the dibasic ester with water in the reactor at an elevated temperature to form a dibasic acid and one or more alcohols, wherein water is added to the reactor during the reacting, and wherein at least 50% of the added water is added as steam, wherein the dibasic acid is 1,18-octadecanedioic acid, and wherein the one or more alcohols comprise methanol;
wherein at least a portion of the formed alcohols are removed from the reactor during the reacting.

2. The method of claim 1 , wherein the reactor comprises:
an inlet for introducing a liquid medium to the reactor; and
an outlet for releasing a gaseous medium from the reactor.

3. The method of claim 1 , wherein at least 20 percent by weight of the formed alcohols are removed from the reactor during the reacting.

4. The method of claim 3 , wherein at least 50 percent by weight of the formed alcohols are removed from the reactor during the reacting.

5. The method claim 1 , wherein the mole-to-mole ratio of water to formed alcohols in the reactor is at least 1:1 during the reacting.

6. The method of claim 5 , wherein the mole-to-mole ratio of water to formed alcohols in the reactor is at least 2:1 during the reacting.

7. The method of claim 1 , wherein the dibasic ester is continuously or semi-continuously added, and optionally removed, to maintain a residence time for the dibasic ester of 1 to 24 hours.

8. The method of claim 1 , wherein the yield of the dibasic acid is at least 75 percent.

9. The method of claim 1 , wherein the reacting further forms one or more colored impurities, and wherein the mole-to-mole ratio of the formed dibasic acid and the formed colored impurities is at least 25:1.

10. The method of claim 1 , wherein the concentration of O 2 in the reactor does not exceed 250 ppm during the reacting, based on the total number of gaseous species in the reactor.

Assignees

• Elevance Renewable Sciences

Inventors

• Patel Alpeshkumar K
• Pease Brian
• Dreyer Bradon J
• Viswanath Yenamandra

Classifications

• C07C51/09 Primary

  from carboxylic acid esters or lactones · CPC title

• C07C67/475

  by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of [IMAGE cpc-sch-C07C-0963.gif] groups between different molecules · CPC title

• C07C67/303

  by hydrogenation of unsaturated carbon-to-carbon bonds · CPC title

• C07C51/43 Primary

  by change of the physical state, e.g. crystallisation · CPC title

• C07C69/34

  Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom · CPC title