WO2025101710A1 - Transesterification catalysis by unneutralized poly alkoxylates - Google Patents
Transesterification catalysis by unneutralized poly alkoxylates Download PDFInfo
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- WO2025101710A1 WO2025101710A1 PCT/US2024/054867 US2024054867W WO2025101710A1 WO 2025101710 A1 WO2025101710 A1 WO 2025101710A1 US 2024054867 W US2024054867 W US 2024054867W WO 2025101710 A1 WO2025101710 A1 WO 2025101710A1
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
- C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
Definitions
- This invention relates generally to transesterification catalysis by unneutralized poly alkoxylates.
- (Meth)acrylate monomers of polyethoxylated or poly alkoxylated alcohols are typically synthesized via either direct esterification or transesterification.
- a common method for producing (meth)acrylate monomers of polyethoxylated or poly alkoxylated alcohols is transesterification of the polyethoxylated or poly alkoxylated alcohols with an alkyl (meth)acrylate using a transesterification catalyst such as lithium hydroxide (LiOH) or tetraethylhexyl titanate.
- a transesterification catalyst such as lithium hydroxide (LiOH) or tetraethylhexyl titanate.
- the poly alkoxylated alcohol is mixed with the alkyl (meth)acrylate and then dehydrated, after which a transesterification catalyst (e.g., LiOH)is added to form the (meth) aery late monomer of the poly alkoxylated alcohol.
- Polyethoxylated or poly alkoxylated alcohols are typically synthesized by base-catalyzed ethoxylation of fatty alcohols.
- Commonly used base catalysts include sodium hydroxide (NaOH) and potassium hydroxide (KOH). These ethoxylation or alkoxylation reactions are terminated by neutralization by acids such as acetic acid or phosphoric acid. It has been discovered that acid neutralization of polyethoxylated or poly alkoxylated alcohols can quench the transesterification catalyst LiOH and result in production irregularities.
- hydroxides such as NaOH and KOH have not been found to provide any appreciable conversions under similar transesterification conditions used for LiOH-catalyzed transesterification reactions to produce (meth)acrylate monomers of polyethoxylated or poly alkoxylated alcohols.
- the present invention solves one or more of the problems associated with conventional processes for producing (meth) acrylate monomers of polyethoxylated or poly alkoxylated alcohols.
- One aspect of the invention provides a process for producing a (meth)acrylate monomer of a poly alkoxylated alcohol.
- the process comprises providing an unneutralized poly alkoxylated alcohol, wherein the unneutralized poly alkoxylated alcohol was produced by basecatalyzed alkoxylation, and transesterifying an alkyl (meth)acrylate with the unneutralized poly alkoxylated alcohol to produce the (meth)acrylate monomer of a poly alkoxylated alcohol.
- No transesterification catalyst is added during the step of esterifying the alkyl (meth)acrylate with the unneutralized poly alkoxylated alcohol.
- Another aspect of the invention provides a process for producing a (meth)acrylate monomer of a poly alkoxylated alcohol comprising reacting an alkyl alcohol with an epoxide in the presence of a base catalyst to form a poly alkoxylated alcohol of formula (I) R OR ⁇ nOH (I) wherein R is an alkyl group comprising 8 to 24 carbon atom, R 1 is an alkenyl group comprising 2 to 4 carbon atoms, and n ranges from 10 to 30.
- An alkyl (meth)acrylate is transesterified with the poly alkoxylated alcohol to produce the (meth)acrylate monomer of the poly alkoxylated alcohol.
- the poly alkoxylated alcohol is not neutralized prior to transesterifying the alkyl (meth)acrylate with the poly alkoxylated alcohol.
- (meth)acrylate monomers of poly alkoxylated alcohols can be prepared by directly transesterifying an alkyl (meth)acrylate with an unneutralized poly alkoxylated alcohol that has been prepared by base-catalyzed alkoxylation.
- This discovery is significant because it allows the transesterification to be performed without adding any additional transesterification catalyst, without the use of expensive lithium hydroxide catalyst, and/or at a faster rate than traditional lithium hydroxide-catalyzed transesterification reactions.
- (meth) acrylate refers to either acrylate or methacrylate or combinations thereof.
- substituted refers to having at least one attached chemical group, for example, alkyl group, alkenyl group, vinyl group, hydroxyl group, carboxylic acid group, other functional groups, and combinations thereof.
- the present invention relates to processes for producing a (meth )acry late monomer of a poly alkoxylated alcohol.
- On aspect of the invention relates to a process for producing a (meth)acrylate monomer of a poly alkoxylated alcohol comprising providing an unneutralized poly alkoxylated alcohol, wherein the unneutralized poly alkoxylated alcohol was produced by base-catalyzed alkoxylation, and transesterifying an alkyl (meth) acrylate with the unneutralized poly alkoxylated alcohol to produce the (meth) acrylate monomer of a poly alkoxylated alcohol.
- the base-catalyzed alkoxylation reaction preferably uses a base catalyst selected from sodium hydroxide (NaOH) and potassium hydroxide (KOH).
- the base catalyst is still present in the unneutralized poly alkoxylated alcohol when the alkyl (meth)acrylate is transesterified with the poly alkoxylated alcohol.
- the inventors have surprisingly discovered that the base catalyst remaining from the alkoxylation reaction is sufficient to catalyze the subsequent transesterification reaction. This outcome is particularly surprising because NaOH and KOH do not typically produce appreciable conversions when used according to conventional transesterification reactions of alkyl (meth)acrylates and poly alkoxylated alcohols catalyzed by lithium hydroxide (LiOH).
- transesterification reactions such as the production of biodiesel
- sodium hydroxide or potassium hydroxide may use sodium hydroxide or potassium hydroxide as a transesterification catalyst.
- these transesterifications use a solvent, such as methanol, that increases the solubility of the catalyst and allows them to effectively catalyze the reaction.
- a solvent such as methanol
- no additional solvent such as methanol or other solvent that increases the solubility of the transesterification catalyst, is added to the reaction in the inventive process.
- transesterification catalyst is added during the step of transesterifying the alkyl (meth)acrylate with the unneutralized poly alkoxylated alcohol.
- the transesterification reaction is catalyzed solely by the residual base catalyst used for the alkoxylation reaction.
- the unneutralized poly alkoxylated alcohol comprises a compound of formula (I):
- R 1 is an alkenyl group comprising 2 to 4 carbon atoms, preferably 2 or 3 carbon atoms (i.e., an ethylenyl or propenyl group), and more preferably 2 carbon atoms (i.e., an ethylenyl group).
- the variable n ranges from 10 to 30, preferably from 15 to 25.
- poly alkoxylated alcohols examples include cetyl alcohol ethoxylate, s (caryl alcohol ethoxylate, lauryl alcohol ethoxylate, and combinations thereof (e.g., cetyl stearyl alcohol ethoxylate).
- the alkyl (meth)acrylate is preferably methyl methacrylate or methyl acrylate. More preferably, the alkyl (meth)acrylate is methyl methacrylate.
- the alkyl (meth)acrylate is preferably added to the reaction mixture in a molar excess with respect to the poly alkoxylated alcohol.
- the molar ratio of alkyl (meth)acrylate to the poly alkoxylated alcohol is at greater than 1:1, more preferably at least 1.5:1, and even more preferably at least 2: 1.
- a polymerization inhibitor may be added with the alkyl (meth)acrylate to prevent unwanted polymerization.
- Suitable polymerization inhibitors are known in the art.
- 4-hydroxy-TEMPO (4-HT) monomethyl ether hydroquinone (MeHQ), or phenothiazine (PTZ) may be used as a polymerization inhibitor.
- the transesterification reaction may take place at a temperature ranging from 100 to 140 °C, preferably from 110 to 130 °C.
- the transesterification reaction is preferably conducted at sub-atmospheric pressure.
- the poly alkoxylated alcohol When the poly alkoxylated alcohol is prepared at a different site or substantially before the transesterification reaction occurs (e.g., at least an hour prior to the transesterification reaction), the poly alkoxylated alcohol can be maintained at an elevated temperature.
- Another aspect of the present invention relates to a process for producing a (meth)acrylate monomer of a poly alkoxylated alcohol comprising reacting an alkyl alcohol with an epoxide in the presence of a base catalyst to form a poly alkoxylated alcohol.
- An alkyl (meth)acrylate is transesterified with the poly alkoxylated alcohol to produce the (meth)acrylate monomer of a poly alkoxylated alcohol.
- the poly alkoxylated alcohol is not neutralized prior to transesterifying an alkyl (meth)acrylate with the poly alkoxylated alcohol.
- the poly alkoxylated alcohol is a compound of formula (I):
- the resulting mixture was heated to the setpoint of 115 °C under reduced pressure of 550 mm Hg.
- the vapor temperature varied between 57 °C and 60 °C.
- the reflux/distillation splitter was set at 70/30 and the distillate was collected over three hours, at this point vapor temperature started to rise and reached 65 °C.
- the amount of MMA/MeOH distillate collected was 14 ml/11.1 g.
- the 'H-NMR analysis of the reaction mixture revealed a 99% conversion of MACOL alcohol.
- the examples further shows that NaOH was incapable of catalyzing the transesterification reaction (Comparative Example #1) using the same reaction conditions as Comparative Example #2, which used LiOH as the transesterification catalyst.
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Abstract
A process for producing a (meth)acrylate monomer of a poly alkoxylated alcohol comprises providing an unneutralized poly alkoxylated alcohol, wherein the unneutralized poly alkoxylated alcohol was produced by base-catalyzed alkoxylation. An alkyl (meth)acrylate is transesterified with the unneutralized poly alkoxylated alcohol to produce the (meth)acrylate monomer of a poly alkoxylated alcohol. No transesterification catalyst is added during the step of transesterifying the alkyl (meth)acrylate with the unneutralized poly alkoxylated alcohol.
Description
TRANSESTERIFICATION CATALYSIS BY UNNEUTRALIZED POLY
ALKOXYLATES
FIELD OF THE INVENTION
This invention relates generally to transesterification catalysis by unneutralized poly alkoxylates.
BACKGROUND
(Meth)acrylate monomers of polyethoxylated or poly alkoxylated alcohols are typically synthesized via either direct esterification or transesterification.
A common method for producing (meth)acrylate monomers of polyethoxylated or poly alkoxylated alcohols is transesterification of the polyethoxylated or poly alkoxylated alcohols with an alkyl (meth)acrylate using a transesterification catalyst such as lithium hydroxide (LiOH) or tetraethylhexyl titanate. Typically, the poly alkoxylated alcohol is mixed with the alkyl (meth)acrylate and then dehydrated, after which a transesterification catalyst (e.g., LiOH)is added to form the (meth) aery late monomer of the poly alkoxylated alcohol.
Polyethoxylated or poly alkoxylated alcohols are typically synthesized by base-catalyzed ethoxylation of fatty alcohols. Commonly used base catalysts include sodium hydroxide (NaOH) and potassium hydroxide (KOH). These ethoxylation or alkoxylation reactions are terminated by neutralization by acids such as acetic acid or phosphoric acid.
It has been discovered that acid neutralization of polyethoxylated or poly alkoxylated alcohols can quench the transesterification catalyst LiOH and result in production irregularities. Other hydroxides such as NaOH and KOH have not been found to provide any appreciable conversions under similar transesterification conditions used for LiOH-catalyzed transesterification reactions to produce (meth)acrylate monomers of polyethoxylated or poly alkoxylated alcohols.
With the rapidly increasing costs of lithium-based catalysts, there is a need for an improved process for producing (meth)acrylate monomers of poly ethoxylated or poly alkoxylated alcohols. The present invention solves one or more of the problems associated with conventional processes for producing (meth) acrylate monomers of polyethoxylated or poly alkoxylated alcohols.
SUMMARY OF THE INVENTION
One aspect of the invention provides a process for producing a (meth)acrylate monomer of a poly alkoxylated alcohol. The process comprises providing an unneutralized poly alkoxylated alcohol, wherein the unneutralized poly alkoxylated alcohol was produced by basecatalyzed alkoxylation, and transesterifying an alkyl (meth)acrylate with the unneutralized poly alkoxylated alcohol to produce the (meth)acrylate monomer of a poly alkoxylated alcohol. No transesterification catalyst is added during the step of esterifying the alkyl (meth)acrylate with the unneutralized poly alkoxylated alcohol.
Another aspect of the invention provides a process for producing a (meth)acrylate monomer of a poly alkoxylated alcohol comprising reacting an alkyl alcohol with an epoxide in the presence of a base catalyst to form a poly alkoxylated alcohol of formula (I)
R OR^nOH (I) wherein R is an alkyl group comprising 8 to 24 carbon atom, R1 is an alkenyl group comprising 2 to 4 carbon atoms, and n ranges from 10 to 30. An alkyl (meth)acrylate is transesterified with the poly alkoxylated alcohol to produce the (meth)acrylate monomer of the poly alkoxylated alcohol. The poly alkoxylated alcohol is not neutralized prior to transesterifying the alkyl (meth)acrylate with the poly alkoxylated alcohol.
DETAILED DESCRIPTION
The inventors have surprisingly found that (meth)acrylate monomers of poly alkoxylated alcohols can be prepared by directly transesterifying an alkyl (meth)acrylate with an unneutralized poly alkoxylated alcohol that has been prepared by base-catalyzed alkoxylation. This discovery is significant because it allows the transesterification to be performed without adding any additional transesterification catalyst, without the use of expensive lithium hydroxide catalyst, and/or at a faster rate than traditional lithium hydroxide-catalyzed transesterification reactions.
As used herein, the term “(meth) acrylate” refers to either acrylate or methacrylate or combinations thereof. As used herein, the term “substituted” refers to having at least one attached chemical group, for example, alkyl group, alkenyl group, vinyl group, hydroxyl group, carboxylic acid group, other functional groups, and combinations thereof.
The present invention relates to processes for producing a (meth )acry late monomer of a poly alkoxylated alcohol.
On aspect of the invention relates to a process for producing a (meth)acrylate monomer of a poly alkoxylated alcohol comprising providing an unneutralized poly alkoxylated alcohol,
wherein the unneutralized poly alkoxylated alcohol was produced by base-catalyzed alkoxylation, and transesterifying an alkyl (meth) acrylate with the unneutralized poly alkoxylated alcohol to produce the (meth) acrylate monomer of a poly alkoxylated alcohol.
The base-catalyzed alkoxylation reaction preferably uses a base catalyst selected from sodium hydroxide (NaOH) and potassium hydroxide (KOH). The base catalyst is still present in the unneutralized poly alkoxylated alcohol when the alkyl (meth)acrylate is transesterified with the poly alkoxylated alcohol. The inventors have surprisingly discovered that the base catalyst remaining from the alkoxylation reaction is sufficient to catalyze the subsequent transesterification reaction. This outcome is particularly surprising because NaOH and KOH do not typically produce appreciable conversions when used according to conventional transesterification reactions of alkyl (meth)acrylates and poly alkoxylated alcohols catalyzed by lithium hydroxide (LiOH). Other transesterification reactions, such as the production of biodiesel, may use sodium hydroxide or potassium hydroxide as a transesterification catalyst. However, these transesterifications use a solvent, such as methanol, that increases the solubility of the catalyst and allows them to effectively catalyze the reaction. Preferably, no additional solvent, such as methanol or other solvent that increases the solubility of the transesterification catalyst, is added to the reaction in the inventive process.
No transesterification catalyst is added during the step of transesterifying the alkyl (meth)acrylate with the unneutralized poly alkoxylated alcohol. The transesterification reaction is catalyzed solely by the residual base catalyst used for the alkoxylation reaction.
Preferably, the unneutralized poly alkoxylated alcohol comprises a compound of formula (I):
R OR' OH (I)
in which R is an alkyl group comprising 8 to 24 carbon atoms, preferably from 10 to 20 carbon atoms. R1 is an alkenyl group comprising 2 to 4 carbon atoms, preferably 2 or 3 carbon atoms (i.e., an ethylenyl or propenyl group), and more preferably 2 carbon atoms (i.e., an ethylenyl group). The variable n ranges from 10 to 30, preferably from 15 to 25.
Examples of poly alkoxylated alcohols include cetyl alcohol ethoxylate, s (caryl alcohol ethoxylate, lauryl alcohol ethoxylate, and combinations thereof (e.g., cetyl stearyl alcohol ethoxylate).
The alkyl (meth)acrylate is preferably methyl methacrylate or methyl acrylate. More preferably, the alkyl (meth)acrylate is methyl methacrylate.
The alkyl (meth)acrylate is preferably added to the reaction mixture in a molar excess with respect to the poly alkoxylated alcohol. Preferably, the molar ratio of alkyl (meth)acrylate to the poly alkoxylated alcohol is at greater than 1:1, more preferably at least 1.5:1, and even more preferably at least 2: 1.
A polymerization inhibitor may be added with the alkyl (meth)acrylate to prevent unwanted polymerization. Suitable polymerization inhibitors are known in the art. For example, 4-hydroxy-TEMPO (4-HT), monomethyl ether hydroquinone (MeHQ), or phenothiazine (PTZ) may be used as a polymerization inhibitor.
The transesterification reaction may take place at a temperature ranging from 100 to 140 °C, preferably from 110 to 130 °C. The transesterification reaction is preferably conducted at sub-atmospheric pressure.
When the poly alkoxylated alcohol is prepared at a different site or substantially before the transesterification reaction occurs (e.g., at least an hour prior to the transesterification reaction), the poly alkoxylated alcohol can be maintained at an elevated temperature.
Another aspect of the present invention relates to a process for producing a (meth)acrylate monomer of a poly alkoxylated alcohol comprising reacting an alkyl alcohol with an epoxide in the presence of a base catalyst to form a poly alkoxylated alcohol. An alkyl (meth)acrylate is transesterified with the poly alkoxylated alcohol to produce the (meth)acrylate monomer of a poly alkoxylated alcohol. The poly alkoxylated alcohol is not neutralized prior to transesterifying an alkyl (meth)acrylate with the poly alkoxylated alcohol.
Preferably, the poly alkoxylated alcohol is a compound of formula (I):
R(OR1)nOH (I) in which R is an alkyl group comprising 8 to 24 carbon atoms, preferably from 10 to 20 carbon atoms; R1 is an alkenyl group comprising 2 to 4 carbon atoms, preferably 2 or 3 carbon atoms, and more preferably 2 carbon atoms; and n ranges from 10 to 30, preferably from 15 to 25.
Some embodiments of the invention will now be described in detail in the following Examples.
EXAMPLES
Inventive Example
To a 1000 ml four- necked flask fitted with a stirrer, thermometer, 10-tray distillation head, and a reflux splitter was added unneutralized cetyl stearyl alcohol ethoxylate (CSA-20, 277.9 g, 0.224 mol), methyl methacrylate (MMA, 149.7 g, 1.49 mol), and polymerization inhibitor 4-HT (0.1 g 0.6 mmol). The reaction mixture was heated to the setpoint of 120 °C under reduced pressure (550 mmHg). The vapor temperature varied between 57 °C and 63 °C. The reflux/distillation splitter was set at 70/30 and the distillate was collected over 2 hours. The amount of MMA/MeOH distillate collected was 13 ml/8.9 g. The 111-NMR analysis of the
reaction mixture after Ih and 2 h revealed 90 and 99% conversion of the cetyl stearyl alcohol ethoxylate.
Excess MM A was distilled off at 200 mmHg to 1 mmHg and the resulting mixture was diluted with 85 g of GMAA and 43 g of water.
Comparative Example #1
To a 1000 ml four-necked flask fitted with a stirrer, thermometer, 10-tray distillation head, and a reflux splitter was added neutralized cetyl stearyl alcohol ethoxylate (CSA-20 acquired from BASF, 278.1 g, 0.224 mol), methyl methacrylate (MMA, 149.5 g, 1.49 mol), and polymerization inhibitor 4-HT (0.25 g). The resulting mixture was dehydrated by distilling off 30 g of MMA under a 550 mmHg vacuum and 105 °C reactor temperature. After the dehydration contents were cooled down and NaOH (0.2 g, 0.005 mol) was added. The resulting mixture was heated to the setpoint of 115 °C under reduced pressure of 550 mm Hg.
After 1 hour of heating at 109 °C, the vapor temperature remained above 90 °C indicating no MeOH generation. The lack of MeOH generation indicates that no transesterification occurred.
Comparative Example #2
To a 1000 ml four-necked flask fitted with a stirrer, thermometer, 10-tray distillation head, and a reflux splitter was added neutralized cetyl stearyl alcohol ethoxylate (CSA-20 from BASF, 278.1 g, 0.224 mol), methyl methacrylate (MMA, 180 g, 1.8 mol), and polymerization inhibitor 4-HT (0.25 g). The resulting mixture was dehydrated by distilling off 29 g of MMA under a 550 mmHg vacuum and 105 °C reactor temperature. After the dehydration contents were
cooled down and LiOH (0.205 g, 0.005 mol) was added. The resulting mixture was heated to the setpoint of 115 °C under reduced pressure of 550 mm Hg. The vapor temperature varied between 57 °C and 60 °C. The reflux/distillation splitter was set at 70/30 and the distillate was collected over three hours, at this point vapor temperature started to rise and reached 65 °C. The amount of MMA/MeOH distillate collected was 14 ml/11.1 g. The 'H-NMR analysis of the reaction mixture revealed a 99% conversion of MACOL alcohol.
Excess MM A was distilled off at 200 mmHg to 1 mmHg and the resulting mixture was diluted with 85 g of GMAA and 43 g of water.
A comparison of the Inventive Example and Comparative Example #1 surprisingly shows that the no additional catalyst was required to conduct the transesterification reaction. The examples further shows that NaOH was incapable of catalyzing the transesterification reaction (Comparative Example #1) using the same reaction conditions as Comparative Example #2, which used LiOH as the transesterification catalyst. A comparison of the Inventive Example and Comparative Example #2 surprisingly shows that even without adding a separate transesterification catalyst, the Inventive Example was able to complete the transesterification reaction faster than using the convention LiOH transesterification catalyst.
Claims
1. A process for producing a (meth)acrylate monomer of a poly alkoxylated alcohol comprising: providing an unneutralized poly alkoxylated alcohol, wherein the unneutralized poly alkoxylated alcohol was produced by base-catalyzed alkoxylation; and transesterifying an alkyl (meth)acrylate with the unneutralized poly alkoxylated alcohol to produce the (meth)acrylate monomer of a poly alkoxylated alcohol; wherein no transesterification catalyst is added during the step of transesterifying the alkyl (meth)acrylate with the unneutralized poly alkoxylated alcohol.
2. The process of claim 1, wherein the step of transesterifying the alkyl (meth)acrylate with the unneutralized poly alkoxylated alcohol to produce the (meth) acrylate monomer of a poly alkoxylated alcohol is catalyzed by residual base catalyst present in the unneutralized poly alkoxylated alcohol.
3. The process of claim 2, wherein the residual base catalyst present in the unneutralized poly alkoxylated alcohol is selected from sodium hydroxide and potassium hydroxide.
4. The process of any one of the preceding claims, the unneutralized poly alkoxylated alcohol comprises a compound of formula (I)
R(OR1)nOH (I) wherein:
R is an alkyl group comprising 8 to 24 carbon atoms;
R1 is an alkenyl group comprising 2 to 4 carbon atoms; and n ranges from 10 to 30.
5. The process of claim 4, wherein R is an alkyl group comprising 10 to 20 carbon atoms.
6. The process of claim 5, wherein R is an alkyl group comprising 12 to 16 carbon atoms.
7. The process of claim 4, wherein R1 is an ethylenyl or propenyl group.
8. The process of claim 7, wherein R1 is an ethylenyl group.
9. The process of claim 4, wherein n ranges from 15 to 25.
10. The process of claim 1, wherein the unneutralized poly alkoxylated alcohol is selected from cetyl alcohol ethoxylate, stearyl alcohol ethoxylate, lauryl alcohol ethoxylate, and combinations thereof.
11. The process of any one of the preceding claims, wherein the unneutralized poly alkoxylated alcohol comprises base catalyst from the base-catalyzed alkoxylation.
12. The process of claim 11, wherein the base catalyst comprises sodium hydroxide or potassium hydroxide.
13. The process of any one of the preceding claims, wherein the alkyl (meth)acrylate is methyl methacrylate.
14. The process of any one of the preceding claims, wherein a polymerization inhibitor is added during the step of transesterifying the alkyl (meth)acrylate with the unneutralized poly alkoxylated alcohol.
15. A process for producing a (meth)acrylate monomer of a poly alkoxylated alcohol comprising: reacting an alkyl alcohol with an epoxide in the presence of a base catalyst to form a poly alkoxylated alcohol of formula (I)
RCOR^nOH (I) wherein:
R is an alkyl group comprising 8 to 24 carbon atoms;
R1 is an alkenyl group comprising 2 to 4 carbon atoms; and n ranges from 10 to 30; and
transesterifying an alkyl (meth)acrylate with the poly alkoxylated alcohol to produce the (meth)acrylate monomer of a poly alkoxylated alcohol. wherein the poly alkoxylated alcohol is not neutralized prior to transesterifying an alkyl (meth)acrylate with the poly alkoxylated alcohol.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0902017A1 (en) * | 1997-08-29 | 1999-03-17 | Rohm And Haas Company | Transesterification process |
| US7687596B2 (en) * | 2003-07-10 | 2010-03-30 | Basf Aktiengesellschaft | (Meth)acrylic acid esters of alkyoxylated unsaturated polyol ethers, and production thereof |
| US20150232409A1 (en) * | 2014-02-18 | 2015-08-20 | Basf Se | Preparation of (meth)acrylic esters of polyalkoxy-containing alcohols |
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- 2024-11-07 WO PCT/US2024/054867 patent/WO2025101710A1/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0902017A1 (en) * | 1997-08-29 | 1999-03-17 | Rohm And Haas Company | Transesterification process |
| US7687596B2 (en) * | 2003-07-10 | 2010-03-30 | Basf Aktiengesellschaft | (Meth)acrylic acid esters of alkyoxylated unsaturated polyol ethers, and production thereof |
| US20150232409A1 (en) * | 2014-02-18 | 2015-08-20 | Basf Se | Preparation of (meth)acrylic esters of polyalkoxy-containing alcohols |
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