IP Library Granted Patent US 9,096,512
Granted Patent B2
US 9,096,512 · App. 14/487,281 · Granted Aug 4, 2015

Methods for preparing methacrylic acid from biobased starting materials

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Quick Facts
Patent No.
US 9,096,512
App. No.
14/487,281
Granted
Aug 4, 2015
Kind
B2
Abstract

Described herein are methods for preparing methacrylic acid from biobased starting materials.

Claims (19)

1. A method for preparing methacrylic acid, comprising the following steps:

a) oxidizing a compound of formula I

wherein R 1 is oxo or hydroxyl, to obtain isobutyric acid;

b) halogenating the isobutyric acid to obtain 3-haloisobutyric acid; and

c) dehalogenating the 3-haloisobutyric acid to obtain methacrylic acid wherein step b) is carried out in the presence of acetic anhydride.

2. The method of claim 1 , wherein R 1 is oxo.

3. The method of claim 1 , wherein R 1 is hydroxyl.

4. The method of claim 1 , wherein the compound of formula I is selected from isobutanol and isobutanal.

5. The method of claim 1 , wherein the oxidizing agent is selected from ozone, potassium permanganate, nitric acid, chromic acid and chromium trioxide.

6. The method of claim 5 , wherein the oxidizing agent is potassium permanganate.

7. The method of claim 1 , wherein the isobutyric acid is halogenated with a halogen selected from fluorine, chlorine, bromine, and iodine.

8. The method of claim 1 , wherein the isobutyric acid is halogenated with chlorine.

9. The method of claim 1 , further comprising the step of purifying the methacrylic acid.

10. The method of claim 9 , wherein the methacrylic acid is purified by distillation.

11. The method of claim 1 , wherein the compound of formula I is prepared by fermentation.

12. The method of claim 1 , wherein the 3-haloisobutryic acid is dehalogenated using an inorganic base.

13. The method of claim 12 , wherein the inorganic base is selected from sodium hydroxide and potassium hydroxide.

14. The method of claim 13 , wherein the inorganic base is sodium hydroxide.

15. The method of claim 1 , further comprising the step of esterifying the methacrylic acid to obtain a methacrylate ester.

Assignments (10)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 26, 2023
From: AFI LICENSING LLC
To: AHF, LLC D/B/A AHF PRODUCTS
Reel/Frame 062499/0179 →
RELEASE OF SECURITY INTEREST Recorded Jul 26, 2022
From: PATHLIGHT CAPITAL LP
To: ARMSTRONG FLOORING, INC.; AFI LICENSING LLC
Reel/Frame 060934/0242 →
RELEASE OF SECURITY INTEREST Recorded Jul 26, 2022
From: BANK OF AMERICA, N.A.
To: ARMSTRONG FLOORING, INC.; AFI LICENSING LLC
Reel/Frame 060934/0554 →
RELEASE OF SECURITY INTEREST Recorded Jul 26, 2022
From: BANK OF AMERICA, N.A.
To: ARMSTRONG FLOORING, INC.; AFI LICENSING LLC
Reel/Frame 060934/0566 →
SECURITY INTEREST Recorded Sep 9, 2020
From: AFI LICENSING LLC
To: BANK OF AMERICA, N.A., AS COLLATERAL AGENT
Reel/Frame 053731/0016 →
SECURITY INTEREST Recorded Jun 24, 2020
From: ARMSTRONG FLOORING, INC.; AFI LICENSING, LLC
To: PATHLIGHT CAPITAL, LP
Reel/Frame 053033/0726 →
CORRECTIVE ASSIGNMENT TO CORRECT THE PROPERTY NUMBERS PREVIOUSLY RECORDED AT REEL: 47999 FRAME: 554. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 1, 2020
From: AFI LICENSING LLC
To: BANK OF AMERICA, N.A., AS COLLATERAL AGENT
Reel/Frame 052804/0921 →
SECURITY INTEREST Recorded Jan 2, 2019
From: AFI LICENSING LLC
To: BANK OF AMERICA, N.A., AS COLLATERAL AGENT
Reel/Frame 047999/0554 →
RELEASE OF SECURITY INTEREST Recorded Dec 31, 2018
From: BANK OF AMERICA, N.A., AS COLLATERAL AGENT
To: AFI LICENSING LLC
Reel/Frame 047996/0459 →
SECURITY INTEREST Recorded Oct 17, 2016
From: AFI LICENSING LLC
To: BANK OF AMERICA, N.A., AS COLLATERAL AGENT
Reel/Frame 040381/0180 →