Selective synthesis of 2-octyl acrylate by acid catalyzed esterification of 2-octanol and acrylic acid

Patent metadata

Field	Value
Publication number	US-9604902-B2
Application number	US-201414769875-A
Country	US
Kind code	B2
Filing date	Mar 4, 2014
Priority date	Mar 15, 2013
Publication date	Mar 28, 2017
Grant date	Mar 28, 2017

Abstract

A method of making 2-octyl acrylate comprising reacting 2-octanol with acrylic acid in the presence of an acid catalyst and added water is described. The 2-octanol may be derived from renewable resources, such as castor oil. The method is efficient and provides selectivity for 2-octyl acrylate.

First claim

What is claimed is:

1. A method of making 2-octyl acrylate comprising reacting 2-octanol with acrylic acid in the presence of an acid catalyst and added water.

2. The method of claim 1 wherein the acid catalyst comprises a heterogeneous acid catalyst.

3. The method of claim 1 wherein functional groups on the acid catalyst comprise sulfonic acid.

4. The method of claim 3 wherein the acid catalyst comprises a cation exchange resin.

5. The method of claim 1 wherein the 2-octanol and acrylic acid are provided in a 3:1 to a 1:3 molar ratio.

6. The method of claim 1 wherein the 2-octyl acrylate comprises between 50% and 100% by weight biobased carbon, as determined using ASTM D6866-12.

7. The method of claim 6 wherein the 2-octanol is derived from castor oil.

8. The method of claim 1 wherein the added water comprises 1 to 5 percent by weight of the total reactants.

9. The method of claim 1 wherein the reaction is performed at a temperature of 60° C. to 130° C.

10. The method of claim 1 wherein the reaction is performed in a continuous reactor at a weight hourly space velocity (WHSV) of 0.1 h −1 to 3 h −1 , wherein the WHSV is a ratio of mass flow of 2-octanol and acrylic acid entering the system per hour to the mass of the acid catalyst.

11. The method of claim 1 wherein 15 to 70% by weight of the 2-octanol is converted to 2-octyl acrylate.

12. The method of claim 1 wherein the acid catalyst comprises a liquid homogeneous acid catalyst.

13. The method of claim 1 wherein the 2-octanol has a 14 C/C ratio of 1.0×10 −14 or higher.

14. A method of making an adhesive comprising:
a. reacting 2-octanol with acrylic acid in the presence of an acid catalyst and added water, thereby forming 2-octyl acrylate; and
b. reacting at least some of the 2-octyl acrylate with at least one initiator and at least one (meth)acrylic acid comonomer, thereby forming the adhesive.

15. The method of claim 14 , wherein the 2-octyl acrylate is the reaction product of 2-octanol with acrylic acid, wherein the 2-octanol has a 14 C/C ratio of 1.0×10 −14 or higher.

Assignees

• 3M Innovative Properties Co

Inventors

• Colby Joshua L
• Clem Tabitha A
• Spawn Terence D
• Hutt Aaron E
• Teply Wade T

Classifications

• Y02P20/582

  Recycling of unreacted starting or intermediate materials · CPC title

• C09J133/08

  Homopolymers or copolymers of acrylic acid esters · CPC title

• C07C57/02

  with only carbon-to-carbon double bonds as unsaturation · CPC title

• C07C67/08 Primary

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

• C08F220/18

  with acrylic or methacrylic acids · CPC title