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

A technology of acrylic acid and acid catalyst, which is applied in the preparation of carboxylic acid esters, ester copolymer adhesives, organic chemistry, etc., and can solve problems such as price and supply instability of adhesive products

Inactive Publication Date: 2015-11-18
3M INNOVATIVE PROPERTIES CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The rise in oil prices and the concomitant rise in the prices of petroleum-derived products have led to price and supply instability for many adhesive products.

Method used

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

Examples

Experimental program
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example

[0117] These examples are for illustrative purposes only, and are not intended to unduly limit the scope of the appended claims. Notwithstanding that the numerical ranges and parameters setting forth the broad scope of the invention are approximations, the numerical values ​​set forth in the specific examples are reported as precisely as possible. Any numerical value, however, inherently contains certain errors necessarily resulting from the standard deviation found in their respective testing measurements. At the very least, and not as an attempt to limit the application of the doctrine of equivalents to the scope of the claims, each numerical parameter should at least be construed in light of the number of reported significant digits and by applying ordinary rounding techniques.

[0118] material overview

[0119] All parts, percentages, ratios, etc. in the examples, as well as in the remainder of this specification, are by weight unless otherwise indicated. Table 1 prov...

example 1

[0124] The 2-octanol conversion, octyl acrylate yield and octene yield of Example 1 were 6.4%, 6.3% and 0.1%, respectively. The 2-octanol conversion, octyl acrylate yield and octene yield of Example 2 were 23.7%, 20.9% and 2.8%, respectively. Octyl acrylate yield is defined as the ratio of the molar flow of octyl acrylate exiting the reactor divided by the molar flow of 2-octanol entering the reactor. Octene yield is defined as the ratio of the molar flow of octene exiting the reactor divided by the molar flow of 2-octanol entering the reactor. The selectivities of the octyl acrylate products of Example 1 and Example 2 were 98.4% and 88.1%, respectively. All results are provided in Table 2 below.

example 3

[0125] Example 3: High yield and selectivity of 2-octyl acrylate

[0126] A 0.5 inch I.D. x 12 inch long stainless steel reactor tube was filled with 20 g of AMBERLY ST 70 catalyst material (sulfonated styrene divinylbenzene copolymer). A 1:1 molar ratio of premixed 2-octanol:acrylic acid (2-octanol derived from castor oil and acrylic acid containing 200 ppm by weight of MEHQ) containing 1% by weight of added water was added at 0.2 mL min -1 Total flow (0.00436molmin -1 or 0.56764gmin -1 2-octanol, 0.00436molmin -1 or 0.31409gmin -1 Acrylic acid, 0.00049molmin -1 or 0.00891gmin -1 water) was continuously fed into the reactor and the reactor pressure was maintained at approximately 50 psig (0.45 MPa). The reactor temperature was maintained at 90°C throughout. After at least three dwells (eg, about 3 minutes total) to reach a steady state, the product was collected for analysis and found to consist primarily of a mixture of octanol, acrylic acid, octene isomers, water, ...

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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.

Description

technical field [0001] The present disclosure relates to the selective synthesis of 2-octyl acrylate comprising the acid-catalyzed esterification of 2-octanol and acrylic acid. Background technique [0002] Pressure sensitive adhesives (PSAs) are known to have properties including: (1) strong and durable tack, (2) cohesiveness under no more than finger pressure, (3) sufficient retention to adherends or on the substrate, and (4) sufficient cohesive strength to enable clean removal from the adherend. Materials that have been found to function well as PSAs include polymers that are designed and formulated to exhibit the requisite viscoelasticity to achieve the desired combination of tack, peel adhesion, and shear holding power. balance. PSAs are characterized by being generally tacky at room temperature (eg 20°C). PSAs do not include compositions simply because they are sticky or capable of clinging to certain surfaces. [0003] Only a limited number of one class of polymer...

Claims

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Application Information

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IPC IPC(8): C07C67/08C08F220/18C09J133/08C07C69/54
CPCC07C67/08C08F220/18C09J133/08Y02P20/582C08F220/1808C07C69/54C08F220/06C07C57/02
Inventor 乔舒亚·L·科尔比塔比萨·A·克莱姆特伦斯·D·斯帕阿伦·E·胡特韦德·T·特普利
Owner 3M INNOVATIVE PROPERTIES CO
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