Synergistic fouling prevention agent composition and method of use thereof
A dispersant, solvating agent, and accelerator composition inhibits ethylenically unsaturated monomer polymerization, addressing fouling issues and maintaining production efficiency by synergistic action.
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- ECOLAB USA INC
- Filing Date
- 2023-10-20
- Publication Date
- 2026-04-23
AI Technical Summary
Ethylenically unsaturated monomers, such as vinyl acetate and methacrylate, polymerize prematurely at high temperatures, leading to fouling and equipment contamination, which reduces production efficiency and requires additional cleaning steps.
A composition comprising a dispersant (imidazoline), a solvating agent (phthalate), and an accelerator (acylamide) is used to mitigate fouling by inhibiting polymerization, even under acidic conditions.
The composition effectively prevents fouling by synergistically inhibiting polymerization, maintaining production efficiency and reducing the need for cleaning, with the components working together to provide greater fouling mitigation than individually.
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Abstract
Description
[Technical Field]
[0001] This disclosure relates, in general, to fouling prevention compositions comprising a blend of a dispersant, a solvating agent, and an accelerator, and to methods of using the same. More specifically, this disclosure relates to a composition comprising an imidazoline-containing dispersant, a phthalate-containing solvating agent, and an acylamide-containing accelerator, which is useful for mitigating fouling of ethylenically unsaturated monomers. This disclosure further relates to a method for preparing a composition having an imidazoline-containing dispersant, a phthalate-containing solvating agent, and an acylamide-containing accelerator. [Background technology]
[0002] The production of ethylenically unsaturated monomers typically involves three steps: reaction, recovery, and purification. High-temperature distillation operations are often involved in the recovery and purification steps. Ethylenelycol-unsaturated monomers, such as vinyl acetate, acrylate, and methacrylate monomers, can be present in the process stream or in purified products produced by various chemical industrial processes. However, these monomer types can undesirably polymerize through radical polymerization, especially at high temperatures, if polymerization initiators are present. As a result, solid deposits of polymers may form on the surface of process equipment during industrial production, processing, handling, or storage. The resulting polymers can be problematic and can lead to equipment "fouling" and product contamination. This may therefore necessitate processing the equipment to remove the polymers or requiring a processing step to remove the polymers from the composition stream or stored composition. These undesirable polymerization reactions consume valuable reagents, resulting in reduced production efficiency, and additional steps may be required to clean the equipment and / or remove the undesirable polymers.
[0003] The premature polymerization of these monomers is generally controlled by administering polymerization inhibitors that can reduce the premature polymerization of the monomers. Conventional polymerization inhibitors contain stable free radicals that can effectively capture carbon-center radicals. Conventional polymerization inhibitors such as 4-hydroxy-2,2,6,6-tetramethylpiperidine-1-oxyl (HTEMPO) and 4-oxo-2,2,6,6-tetramethylpiperidine-1-oxyl (OTEMPO) generally degrade in acidic environments, reducing their effectiveness as polymerization inhibitors. Therefore, there is a need to develop novel polymerization inhibitors, particularly those that are stable under acidic conditions.
[0004] Methyl methacrylate plants are plagued by fouling problems that can occur in methacrylic acid (MAA) production, esterification, purification, and waste acid units. Phenothiazine (PTZ) solutions are typically prepared at low concentrations due to insufficient solubility, but concentrated formulations are needed to improve fouling prevention applications. [Overview of the project]
[0005] Compositions for mitigating fouling caused by monomer polymerization are disclosed herein. The composition comprises a dispersant which is imidazoline, a solvating agent which is a phthalate, and an accelerator which is an acylamide. In some embodiments, the composition is useful for mitigating fouling of ethylenically unsaturated monomers including methacrylic acid, methyl methacrylate, acrylic acid, acrylic acid esters, methacrylamide sulfate, vinyl acetate, acrylonitrile, acrolein, acrylate, methacrylate, 1,3-butadiene, styrene, isoprene, and combinations thereof.
[0006] In some embodiments, the dispersant is of formula (I): [ka] [In the formula, R is C1~C 30is an alkylene, and R 1 , R 2 and R 3 are each independently selected from the group consisting of H, C1-C 30 alkyl, C2-C 30 alkenyl, C6-C 30 aryl, C1-C 30 alkyl-C6-C 30 aryl, C6-C 30 aryl-C1-C 30 alkyl, C1-C 30 aminoalkyl, and C6-C 30 aminoaryl, and R 4 is hydrogen, -(CH)COOH, -CHCH(CH)COOH, imidazoline, C1-C 30 alcohol, C1-C 30 ester, C1-C 30 amide, and C1-C 30 alkyl-C6-C 30 aryl, and n is 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9. The imidazoline or its derivative is included. In some embodiments, R is C1-C 10 alkylene. In some embodiments, R 4 is hydrogen, -CH2COOH, -(CH2)2COOH, -CH2CH(CH3)COOH, imidazoline, C1-C 30 alcohol, and C1-C 30 alkyl-C6-C 20 aryl selected from the group consisting of.
[0007] In some embodiments, R is C1-C 10 alkylene, and R 1 , R 2 and R 3 are each independently selected from the group consisting of H, C1-C 10 alkyl, C2-C 10 alkenyl, C6-C 20 aryl, C1-C 10 alkyl-C6-C 20 aryl, C6-C 20 aryl-C1-C 10 alkyl, C1-C 10Aminoalkyl, and C6-C 20 Independently selected from the group consisting of aminoaryls, R 4 These are hydrogen, -(CH)COOH, -CHCH(CH)COOH, imidazoline, C1~C 10 Alcohol, C1~C 10 Ester, C1~C 10 Amides, and C1-C 10 Alkyl-C6~C 20 Selected from a group consisting of aryl groups.
[0008] In some embodiments, R 1 , R 2 , and R 3 Each of these is hydrogen, n is 0, and R 4 It is hydroxyethyl.
[0009] In certain embodiments, imidazoline is selected from the group consisting of tall oil hydroxyethylimidazoline (CAS number 61791-39-7) and oleate imidazoline (CAS number 68052-47-1). In certain embodiments, imidazoline is tall oil hydroxyethylimidazoline.
[0010] In some embodiments, phthalate is given by formula (II); [ka] [In the formula, R 5 and R 6 These are C1 to C, respectively. 10 Alkyl, C2~C 10 Alkenil, C6~C 10 Aryl, C1~C 10 Alkyl-C6~C 10 Aryl, C6~C 10 Aryl-C1~C 10 Alkyl, C1-C 10 Aminoalkyl, and C6-C 10 It includes compounds independently selected from the group consisting of aminoaryl compounds.
[0011] In certain embodiments, the phthalate is selected from the group consisting of dimethyl phthalate, diethyl phthalate, and diisobutyl phthalate. In certain embodiments, the phthalate is dimethyl phthalate.
[0012] In some embodiments, acylamide is given by formula (III): [ka] [In the formula, R 7 , R 8 and R 9 These are hydrogen, C1-C, respectively. 20 Alkyl, C2~C 20 Alkenyl, and C6~C 20 Includes compounds independently selected from the group consisting of aryl compounds.
[0013] In certain embodiments, the acylamide is selected from the group consisting of dimethylacetamide and N,N-dimethylformamide. In certain embodiments, the acylamide is dimethylacetamide.
[0014] In some embodiments, the compositions of the Disclosure exhibit synergistic effects with respect to their ability to mitigate fouling. For example, in some embodiments, the compositions of the Disclosure exhibit greater fouling mitigation than the individual components present in the composition, thereby controlling the dosage of the active ingredient.
[0015] In some embodiments, the compositions of the present disclosure are active even under acidic conditions, unlike conventional polymerization inhibitors known in the art. Accordingly, in some embodiments, the compositions of the present disclosure also include one or more acids.
[0016] Methods for mitigating fouling caused by monomer polymerization are also disclosed herein. These methods include adding the compositions of the disclosure to monomers. Adding the compositions of the disclosure to process equipment can mitigate fouling.
[0017] The foregoing has broadly outlined the features and technical advantages of the present disclosure so that subsequent embodiments for carrying out the invention may be better understood. Further features and advantages of the present disclosure, which form the subject matter of the claims of this application, are described below. It should be understood by those skilled in the art that the disclosed concepts and specific embodiments can be readily used as a basis for modifying or designing other embodiments to accomplish the same objectives as the present disclosure. It should also be recognized by those skilled in the art that such equivalent embodiments do not deviate from the spirit and scope of the present disclosure as expressed in the appended claims. [Modes for carrying out the invention]
[0018] Various embodiments of this disclosure are described below. The relationships and functions of the various elements of the embodiments can be better understood by referring to the detailed description below. However, embodiments are not limited to those expressly described herein.
[0019] This disclosure relates to compositions comprising a blend of fouling inhibitors and methods for using them to mitigate fouling caused by polymerization of ethylenically unsaturated monomers. The fouling inhibitor compositions of this disclosure comprise a dispersant comprising imidazoline, a solvating agent comprising a phthalate, and an accelerator comprising an acylamide. The fouling inhibitor compositions may be blends of multiple components, comprising, in addition to the aforementioned compounds, a component comprising a dispersant comprising imidazoline, a solvating agent comprising a phthalate, and an accelerator comprising an acylamide.
[0020] definition The term “fowling” refers to the formation of polymers, prepolymers, oligomers, and / or other materials that become insoluble in a flow and / or precipitate out of the flow and accumulate in the equipment under operating conditions. Similarly, the inhibitors, retarders, and amine stabilizer components and compositions of this disclosure can be referred to as “fowling-preventive” as they inhibit or reduce such formation.
[0021] As used herein, "mitigate" or "mitigate," etc., means that the composition does not inhibit polymer formation or fouling itself, and rather, does not block the pipeline, allowing the formed foulant to move from the system to subsequent units.
[0022] Composition of the present disclosure This disclosure relates to compositions for mitigating fouling caused by monomer polymerization, comprising a dispersant containing imidazoline, a solvating agent containing a phthalate, and an accelerator containing an acylamide. In some embodiments, the compositions are for mitigating fouling caused by monomer polymerization, and the monomers are ethylenically unsaturated monomers. For example, the compositions of this disclosure are useful for mitigating fouling caused by polymerization of ethylenically unsaturated monomers, including but not limited to methacrylic acid, methyl methacrylate, acrylic acid, acrylic acid esters, methacrylamide sulfate, vinyl acetate, acrylonitrile, acrolein, acrylate, methacrylate, 1,3-butadiene, styrene, isoprene, and combinations thereof.
[0023] In some embodiments, the dispersant is of formula (I): [ka] [In the formula, R is C1~C 30 It is alkylene, R 1 , R 2 and R 3 These are H, C1-C respectively. 30 Alkyl, C2~C 30 Alkenil, C6~C 30 Aryl, C1~C 30 Alkyl-C6~C 30 Aryl, C6~C 30 Aryl-C1~C 30 Alkyl, C1-C 30 Aminoalkyl, and C6-C 30 Independently selected from the group consisting of aminoaryls, R 4is selected from the group consisting of hydrogen, -CH2COOH, -(CH2)2COOH, -CH2CH(CH3)COOH, imidazoline, C1-C 30 alcohol, C1-C 30 ester, C1-C 30 amide, and C1-C 30 alkylaryl, and n is 0, 1, 2, 3, 4, 5, 6, 7, 8, or 9, and includes an imidazoline or a derivative thereof. In some embodiments, R is C1-C 10 alkylene.
[0024] In some embodiments, R is C1-C 10 alkylene, and R 1 , R 2 and R 3 are each independently selected from the group consisting of H, C1-C 10 alkyl, C2-C 10 alkenyl, C6-C 20 aryl, C1-C 10 alkyl-C6-C 20 aryl, C6-C 20 aryl-C1-C 10 alkyl, C1-C 10 aminoalkyl, and C6-C 20 aminoaryl, and R 4 is selected from the group consisting of hydrogen, -(CH)COOH, -CHCH(CH)COOH, imidazoline, C1-C 10 alcohol, C1-C 10 ester, C1-C 10 amide, and C1-C 10 alkyl-C6-C 20 aryl.
[0025] ] In some embodiments, R 1 , R 2 , and R 3 are each hydrogen, n is 0, and R 4 is hydroxyethyl.
[0026] In certain embodiments, imidazoline is selected from the group consisting of tall oil hydroxyethylimidazoline (CAS number 61791-39-7) and oleate imidazoline (CAS number 68052-47-1). In certain embodiments, imidazoline is tall oil hydroxyethylimidazoline.
[0027] In some embodiments, phthalate is given by formula (II); [ka] [In the formula, R 5 and R 6 These are C1 to C, respectively. 10 Alkyl, C2~C 10 Alkenyl, C1~C 10 Aryl, C1~C 10 Alkyl-C6~C 10 Aryl, C6~C 10 Aryl-C1~C 10 Alkyl, C1-C 10 Aminoalkyl, and C6-C 10 It includes compounds independently selected from the group consisting of aminoaryl compounds.
[0028] In certain embodiments, the phthalate is selected from the group consisting of dimethyl phthalate, diethyl phthalate, and diisobutyl phthalate. In certain embodiments, the phthalate is dimethyl phthalate.
[0029] In some embodiments, acylamide is given by formula (III): [ka] [In the formula, R 7 , R 8 and R 9 These are hydrogen, C1-C, respectively. 20 Alkyl, C2~C 20 Alkenyl and C1-C 20 Includes compounds independently selected from the group consisting of aryl compounds.
[0030] In certain embodiments, the acylamide is selected from the group consisting of dimethylacetamide and N,N-dimethylformamide. In certain embodiments, the acylamide is dimethylacetamide.
[0031] In some embodiments, the compositions unexpectedly exhibit synergistic effects, with the combination of an imidazoline dispersant, a phthalate solvating agent, and an acylamide accelerator resulting in a greater degree of fouling relief than would be expected for that combination.
[0032] In some embodiments, the accelerator is present in the composition at a concentration of about 0.1% to about 99.9% by weight. For example, the accelerator may be present in the composition at concentrations of about 0.1% to about 99.9% by weight, about 0.1% to about 99% by weight, about 0.1% to about 95% by weight, about 0.1% to about 90% by weight, about 0.1% to about 80% by weight, about 0.1% to about 75% by weight, about 0.1% to about 70% by weight, about 0.1% to about 60% by weight, about 0.1% to about 50% by weight, about 0.1% to about 40% by weight, about 0.1% to about 30% by weight, about 0.1% to about 25% by weight, and about 0.1% to about 2% by weight. 0% by weight, about 0.1% to about 15% by weight, about 0.1% to about 10% by weight, about 0.1% to about 5% by weight, about 0.1% to about 1% by weight, about 1% to about 99.9% by weight, about 1% to about 99% by weight, about 1% to about 95% by weight, about 1% by weight About 90% by weight, about 1% to about 80% by weight, about 1% to about 75% by weight, about 1% to about 70% by weight, about 1% to about 60% by weight, about 1% to about 50% by weight, about 1% to about 40% by weight, about 1% to about 30% by weight, about 1% to about 25% by weight, About 1% to about 20% by weight, about 1% to about 15% by weight, about 1% to about 10% by weight, about 1% to about 5% by weight, about 5% to about 99% by weight, about 5% to about 95% by weight, about 5% to about 90% by weight, about 5% to about 80% by weight, about 5% to about 5% by weight 75% by weight, about 5% to about 70% by weight, about 5% to about 60% by weight, about 5% to about 50% by weight, about 5% to about 40% by weight, about 5% to about 30% by weight, about 5% to about 25% by weight, about 5% to about 20% by weight, about 5% to about 15% by weight, about 5% to about 10% by weight, about 10% to about 99.9% by weight, about 10% to about 99% by weight, about 10% to about 95% by weight, about 10% to about 90% by weight, about 10% to about 80% by weight, about 10% to about 75% by weight, about 10% to about 70% by weight %, about 10% to about 60%, about 10% to about 50%, about 10% to about 40%, about 10% to about 30%, about 10% to about 25%, about 10% to about 20%, about 10% to about 15%, about 15% to about 99%.9% by weight, approximately 15% to approximately 99% by weight, approximately 15% to approximately 95% by weight, approximately 15% to approximately 90% by weight, approximately 15% to approximately 80% by weight, approximately 15% to approximately 75% by weight, approximately 15% to approximately 70% by weight, approximately 15% to approximately 60% by weight, approximately 15% to approximately 50% by weight, approximately 15% to approximately 40% by weight, approximately 15% to approximately 30% by weight, approximately 15% to approximately 25% by weight, approximately 15% to approximately 20% by weight, approximately 20% to approximately 99.9% by weight, approximately 20% to approximately 99% by weight, approximately 20% to approximately 95% by weight, approximately 20% to approximately 90% by weight, approximately 20% to approximately 80% by weight Approximately 20% to 75% by weight, approximately 20% to 70% by weight, approximately 20% to 60% by weight, approximately 20% to 50% by weight, approximately 20% to 40% by weight, approximately 20% to 30% by weight, approximately 20% to 25% by weight, approximately 25% to 99.9% by weight, approximately 25% to 99% by weight, approximately 25% to 95% by weight, approximately 25% to 90% by weight, approximately 25% to 80% by weight, approximately 25% to 75% by weight, approximately 25% to 70% by weight, approximately 25% to 60% by weight, approximately 25% to 50% by weight, approximately 25% to 40% by weight, approximately 25% by weight %~approx. 30% by weight, 30% by weight~approx. 99.9% by weight, 30% by weight~approx. 99% by weight, 30% by weight~approx. 95% by weight, 30% by weight~approx. 90% by weight, 30% by weight~approx. 80% by weight, 30% by weight~approx. 75% by weight, 30% by weight~approx. 70% by weight, 30% by weight~approx. 60% by weight, 30% by weight~approx. 50% by weight, 30% by weight~approx. 40% by weight, 40% by weight~approx. 99.9% by weight, 40% by weight~approx. 99% by weight, 40% by weight~approx. 95% by weight, 40% by weight~approx. 90% by weight, 40% by weight~approx. 80% by weight, 40% by weight~approx. 75% by weight, 40% by weight~approx. 70% by weight, approximately 40% to 60% by weight, approximately 40% to 50% by weight, approximately 50% to 99.9% by weight, approximately 50% to 99% by weight, approximately 50% to 95% by weight, approximately 50% to 90% by weight, approximately 50% to 80% by weight, approximately 50% to 75% by weight, approximately 50% to 70% by weight, approximately 50% to 60% by weight, approximately 60% to 99.9% by weight, approximately 60% to 99% by weight, approximately 60% to 95% by weight, approximately 60% to 90% by weight, approximately 60% to 80% by weight, approximately 60% to 70% by weight, approximately 70% to 99% by weight.9% by weight, about 70% to about 99% by weight, about 70% to about 95% by weight, about 70% to about 90% by weight, about 70% to about 80% by weight, about 70% to about 75% by weight, about 75% to about 99.9% by weight, about 75% to about 99% by weight, About 75% to about 95% by weight, about 75% to about 90% by weight, about 75% to about 80% by weight, about 80% to about 99.9% by weight, about 80% to about 99% by weight, about 80% to about 95% by weight, about 80% to about 90% by weight, about 90% by weight The accelerator can be present in concentrations of approximately 99.9% by weight, approximately 90% to approximately 99% by weight, approximately 90% to approximately 95% by weight, approximately 95% to approximately 99.9% by weight, approximately 95% to approximately 99% by weight, approximately 0.1% by weight, 1% by weight, 5% by weight, 10% by weight, 15% by weight, 20% by weight, 25% by weight, 30% by weight, 40% by weight, 50% by weight, 60% by weight, 70% by weight, 75% by weight, 80% by weight, 90% by weight, 95% by weight, 99% by weight, or 99.9% by weight. In some embodiments, the accelerator is present in the composition at a concentration of approximately 10% to approximately 60% by weight.
[0033] In some embodiments, the dispersant is present in the composition at a concentration of about 0.1% to about 99.9% by weight. For example, the dispersant may be present in the composition at concentrations of about 0.1% to about 99.9% by weight, about 0.1% to about 99% by weight, about 0.1% to about 95% by weight, about 0.1% to about 90% by weight, about 0.1% to about 80% by weight, about 0.1% to about 75% by weight, about 0.1% to about 70% by weight, about 0.1% to about 60% by weight, about 0.1% to about 50% by weight, about 0.1% to about 40% by weight, about 0.1% to about 30% by weight, about 0.1% to about 25% by weight, and about 0.1% to about 2% by weight. 0% by weight, about 0.1% to about 15% by weight, about 0.1% to about 10% by weight, about 0.1% to about 5% by weight, about 0.1% to about 1% by weight, about 1% to about 99.9% by weight, about 1% to about 99% by weight, about 1% to about 95% by weight, about 1% by weight About 90% by weight, about 1% to about 80% by weight, about 1% to about 75% by weight, about 1% to about 70% by weight, about 1% to about 60% by weight, about 1% to about 50% by weight, about 1% to about 40% by weight, about 1% to about 30% by weight, about 1% to about 25% by weight, About 1% to about 20% by weight, about 1% to about 15% by weight, about 1% to about 10% by weight, about 1% to about 5% by weight, about 5% to about 99% by weight, about 5% to about 95% by weight, about 5% to about 90% by weight, about 5% to about 80% by weight, about 5% to about 5% by weight 75% by weight, about 5% to about 70% by weight, about 5% to about 60% by weight, about 5% to about 50% by weight, about 5% to about 40% by weight, about 5% to about 30% by weight, about 5% to about 25% by weight, about 5% to about 20% by weight, about 5% to about 15% by weight, about 5% to about 10% by weight, about 10% to about 99.9% by weight, about 10% to about 99% by weight, about 10% to about 95% by weight, about 10% to about 90% by weight, about 10% to about 80% by weight, about 10% to about 75% by weight, about 10% to about 70% by weight %, about 10% to about 60%, about 10% to about 50%, about 10% to about 40%, about 10% to about 30%, about 10% to about 25%, about 10% to about 20%, about 10% to about 15%, about 15% to about 99%.9% by weight, approximately 15% to approximately 99% by weight, approximately 15% to approximately 95% by weight, approximately 15% to approximately 90% by weight, approximately 15% to approximately 80% by weight, approximately 15% to approximately 75% by weight, approximately 15% to approximately 70% by weight, approximately 15% to approximately 60% by weight, approximately 15% to approximately 50% by weight, approximately 15% to approximately 40% by weight, approximately 15% to approximately 30% by weight, approximately 15% to approximately 25% by weight, approximately 15% to approximately 20% by weight, approximately 20% to approximately 99.9% by weight, approximately 20% to approximately 99% by weight, approximately 20% to approximately 95% by weight, approximately 20% to approximately 90% by weight, approximately 20% to approximately 80% by weight Approximately 20% to 75% by weight, approximately 20% to 70% by weight, approximately 20% to 60% by weight, approximately 20% to 50% by weight, approximately 20% to 40% by weight, approximately 20% to 30% by weight, approximately 20% to 25% by weight, approximately 25% to 99.9% by weight, approximately 25% to 99% by weight, approximately 25% to 95% by weight, approximately 25% to 90% by weight, approximately 25% to 80% by weight, approximately 25% to 75% by weight, approximately 25% to 70% by weight, approximately 25% to 60% by weight, approximately 25% to 50% by weight, approximately 25% to 40% by weight, approximately 25% by weight %~approx. 30% by weight, 30% by weight~approx. 99.9% by weight, 30% by weight~approx. 99% by weight, 30% by weight~approx. 95% by weight, 30% by weight~approx. 90% by weight, 30% by weight~approx. 80% by weight, 30% by weight~approx. 75% by weight, 30% by weight~approx. 70% by weight, 30% by weight~approx. 60% by weight, 30% by weight~approx. 50% by weight, 30% by weight~approx. 40% by weight, 40% by weight~approx. 99.9% by weight, 40% by weight~approx. 99% by weight, 40% by weight~approx. 95% by weight, 40% by weight~approx. 90% by weight, 40% by weight~approx. 80% by weight, 40% by weight~approx. 75% by weight, 40% by weight~approx. 70% by weight, approximately 40% to 60% by weight, approximately 40% to 50% by weight, approximately 50% to 99.9% by weight, approximately 50% to 99% by weight, approximately 50% to 95% by weight, approximately 50% to 90% by weight, approximately 50% to 80% by weight, approximately 50% to 75% by weight, approximately 50% to 70% by weight, approximately 50% to 60% by weight, approximately 60% to 99.9% by weight, approximately 60% to 99% by weight, approximately 60% to 95% by weight, approximately 60% to 90% by weight, approximately 60% to 80% by weight, approximately 60% to 70% by weight, approximately 70% to 99% by weight.9% by weight, about 70% to about 99% by weight, about 70% to about 95% by weight, about 70% to about 90% by weight, about 70% to about 80% by weight, about 70% to about 75% by weight, about 75% to about 99.9% by weight, about 75% to about 99% by weight, About 75% to about 95% by weight, about 75% to about 90% by weight, about 75% to about 80% by weight, about 80% to about 99.9% by weight, about 80% to about 99% by weight, about 80% to about 95% by weight, about 80% to about 90% by weight, about 90% by weight The dispersant can be present in concentrations of approximately 99.9% by weight, approximately 90% to approximately 99% by weight, approximately 90% to approximately 95% by weight, approximately 95% to approximately 99.9% by weight, approximately 95% to approximately 99% by weight, approximately 0.1% by weight, 1% by weight, 5% by weight, 10% by weight, 15% by weight, 20% by weight, 25% by weight, 30% by weight, 40% by weight, 50% by weight, 60% by weight, 70% by weight, 75% by weight, 80% by weight, 90% by weight, 95% by weight, 99% by weight, or 99.9% by weight. In some embodiments, the dispersant is present in the composition at a concentration of approximately 30% to approximately 80% by weight.
[0034] In some embodiments, the solvating agent is present in the composition at a concentration of about 0.1% to about 99.9% by weight. For example, the solvating agent may be present in the composition at concentrations of about 0.1% to about 99.9% by weight, about 0.1% to about 99% by weight, about 0.1% to about 95% by weight, about 0.1% to about 90% by weight, about 0.1% to about 80% by weight, about 0.1% to about 75% by weight, about 0.1% to about 70% by weight, about 0.1% to about 60% by weight, about 0.1% to about 50% by weight, about 0.1% to about 40% by weight, about 0.1% to about 30% by weight, about 0.1% to about 25% by weight, and about 0.1% to about 2% by weight. 0% by weight, about 0.1% to about 15% by weight, about 0.1% to about 10% by weight, about 0.1% to about 5% by weight, about 0.1% to about 1% by weight, about 1% to about 99.9% by weight, about 1% to about 99% by weight, about 1% to about 95% by weight, about 1% by weight About 90% by weight, about 1% to about 80% by weight, about 1% to about 75% by weight, about 1% to about 70% by weight, about 1% to about 60% by weight, about 1% to about 50% by weight, about 1% to about 40% by weight, about 1% to about 30% by weight, about 1% to about 25% by weight, About 1% to about 20% by weight, about 1% to about 15% by weight, about 1% to about 10% by weight, about 1% to about 5% by weight, about 5% to about 99% by weight, about 5% to about 95% by weight, about 5% to about 90% by weight, about 5% to about 80% by weight, about 5% to about 5% by weight 75% by weight, about 5% to about 70% by weight, about 5% to about 60% by weight, about 5% to about 50% by weight, about 5% to about 40% by weight, about 5% to about 30% by weight, about 5% to about 25% by weight, about 5% to about 20% by weight, about 5% to about 15% by weight, about 5% to about 10% by weight, about 10% to about 99.9% by weight, about 10% to about 99% by weight, about 10% to about 95% by weight, about 10% to about 90% by weight, about 10% to about 80% by weight, about 10% to about 75% by weight, about 10% to about 70% by weight %, about 10% to about 60%, about 10% to about 50%, about 10% to about 40%, about 10% to about 30%, about 10% to about 25%, about 10% to about 20%, about 10% to about 15%, about 15% to about 99%.9% by weight, approximately 15% to approximately 99% by weight, approximately 15% to approximately 95% by weight, approximately 15% to approximately 90% by weight, approximately 15% to approximately 80% by weight, approximately 15% to approximately 75% by weight, approximately 15% to approximately 70% by weight, approximately 15% to approximately 60% by weight, approximately 15% to approximately 50% by weight, approximately 15% to approximately 40% by weight, approximately 15% to approximately 30% by weight, approximately 15% to approximately 25% by weight, approximately 15% to approximately 20% by weight, approximately 20% to approximately 99.9% by weight, approximately 20% to approximately 99% by weight, approximately 20% to approximately 95% by weight, approximately 20% to approximately 90% by weight, approximately 20% to approximately 80% by weight Approximately 20% to 75% by weight, approximately 20% to 70% by weight, approximately 20% to 60% by weight, approximately 20% to 50% by weight, approximately 20% to 40% by weight, approximately 20% to 30% by weight, approximately 20% to 25% by weight, approximately 25% to 99.9% by weight, approximately 25% to 99% by weight, approximately 25% to 95% by weight, approximately 25% to 90% by weight, approximately 25% to 80% by weight, approximately 25% to 75% by weight, approximately 25% to 70% by weight, approximately 25% to 60% by weight, approximately 25% to 50% by weight, approximately 25% to 40% by weight, approximately 25% by weight %~approx. 30% by weight, 30% by weight~approx. 99.9% by weight, 30% by weight~approx. 99% by weight, 30% by weight~approx. 95% by weight, 30% by weight~approx. 90% by weight, 30% by weight~approx. 80% by weight, 30% by weight~approx. 75% by weight, 30% by weight~approx. 70% by weight, 30% by weight~approx. 60% by weight, 30% by weight~approx. 50% by weight, 30% by weight~approx. 40% by weight, 40% by weight~approx. 99.9% by weight, 40% by weight~approx. 99% by weight, 40% by weight~approx. 95% by weight, 40% by weight~approx. 90% by weight, 40% by weight~approx. 80% by weight, 40% by weight~approx. 75% by weight, 40% by weight~approx. 70% by weight, approximately 40% to 60% by weight, approximately 40% to 50% by weight, approximately 50% to 99.9% by weight, approximately 50% to 99% by weight, approximately 50% to 95% by weight, approximately 50% to 90% by weight, approximately 50% to 80% by weight, approximately 50% to 75% by weight, approximately 50% to 70% by weight, approximately 50% to 60% by weight, approximately 60% to 99.9% by weight, approximately 60% to 99% by weight, approximately 60% to 95% by weight, approximately 60% to 90% by weight, approximately 60% to 80% by weight, approximately 60% to 70% by weight, approximately 70% to 99% by weight.9% by weight, about 70% to about 99% by weight, about 70% to about 95% by weight, about 70% to about 90% by weight, about 70% to about 80% by weight, about 70% to about 75% by weight, about 75% to about 99.9% by weight, about 75% to about 99% by weight, About 75% to about 95% by weight, about 75% to about 90% by weight, about 75% to about 80% by weight, about 80% to about 99.9% by weight, about 80% to about 99% by weight, about 80% to about 95% by weight, about 80% to about 90% by weight, about 90% by weight The solvating agent can be present in concentrations of approximately 99.9% by weight, approximately 90% to approximately 99% by weight, approximately 90% to approximately 95% by weight, approximately 95% to approximately 99.9% by weight, approximately 95% to approximately 99% by weight, approximately 0.1% by weight, 1% by weight, 5% by weight, 10% by weight, 15% by weight, 20% by weight, 25% by weight, 30% by weight, 40% by weight, 50% by weight, 60% by weight, 70% by weight, 75% by weight, 80% by weight, 90% by weight, 95% by weight, 99% by weight, or 99.9% by weight. In some embodiments, the solvating agent is present in the composition at a concentration of approximately 30% to approximately 80% by weight.
[0035] In some embodiments, the weight ratio of the dispersant to the solvating agent may be about 10:1 to about 1:10. While not limiting, examples of weight ratios of dispersant to solvating agents include approximately 10:1 to 1:10, 10:1 to 1:9, 10:1 to 1:8, 10:1 to 1:7, 10:1 to 1:6, 10:1 to 1:5, 10:1 to 1:4, 10:1 to 1:3, 10:1 to 1:2, 10:1 to 1:1, 9:1 to 1:10, 9:1 to 1:9, 9:1 to 1:8, 9:1 to 1:7, 9:1 to 1:6, 9:1 to 1:5, 9:1 to 1:4, 9:1 to 1:3, 9:1 to 1:2, and 9:1 to 1: 1:1, approx. 8:1~approx. 1:10, approx. 8:1~approx. 1:9, approx. 8:1~approx. 1:8, approx. 8:1~approx. 1:7, approx. 8:1~approx. 1:6, approx. 8:1~approx. 1:5, approx. 8:1~approx. 1:4, approx. 8:1~approx. 1:3, approx. 8:1~approx. 1:2, approx. 8:1~approx. 1:1, approx. 7:1~approx. 1:10, approx. 7:1~approx. 1:9, approx. 7:1~approx. 1:8, approx. 7:1~approx. 1:7, approx. 7:1~approx. 1:6, approx. 7:1~approx. 1:5, approx. 7:1~approx. 1:4, approx. 7:1~approx. 1:3, approx. 7:1~approx. 1:2, approx. 7:1~approx. 1:1, approx. 6:1~approx. 1:10, approx. 6:1~approx. 1:9, approx. 6:1~approx. 1:8, Approximately 6:1~1:7, Approximately 6:1~1:6, Approximately 6:1~1:5, Approximately 6:1~1:4, Approximately 6:1~1:3, Approximately 6:1~1:2, Approximately 6:1~1:1, Approximately 5:1~1:10, Approximately 5:1~1:9, Approximately 5:1~1:8, Approximately 5:1~1:7, Approximately 5:1~1:6, Approximately 5:1~1:5, Approximately 5:1~1:4, Approximately 5:1~1:3, Approximately 5:1~1:2, Approximately 5:1~1:1, Approximately 4:1~1:10, Approximately 4:1~1:9, Approximately 4:1~1:8, Approximately 4:1~1:7, Approximately 4:1~1:6, Approximately 4:1~1:5, Approximately 4:1~ Approximately 1:4, approximately 4:1~1:3, approximately 4:1~1:2, approximately 4:1~1:1, approximately 3:1~1:10, approximately 3:1~1:9, approximately 3:1~1:8, approximately 3:1~1:7, approximately 3:1~1:6, approximately 3:1~1:5, approximately 3:1~1:4, approximately 3:1~1:3, approximately 3:1~1:2, approximately 3:1~1:1, approximately 2:1~1:10, approximately 2:1~1:9, approximately 2:1~1:8, approximately 2:1~1:7, approximately 2:1~1:6, approximately 2:1~1:5, approximately 2:1~1:4, approximately 2:1~1:3, approximately 2:1~1:2, approximately 2:1~1:1,The ratios may be approximately 1:1 to 1:10, 1:1 to 1:9, 1:1 to 1:8, 1:1 to 1:7, 1:1 to 1:6, 1:1 to 1:5, 1:1 to 1:4, 1:1 to 1:3, 1:1 to 1:2, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, or 1:10.
[0036] The composition may also optionally contain one or more additional solvents. In certain embodiments, the additional solvents may be selected from water, esters, aromatic compounds, aliphatic compounds, amides, acylamides, alcohols, liquid polymers, and combinations thereof. If an alcohol is used, it may be the same as, for example, an alcohol used in a manufacturing process such as a (meth)acrylate manufacturing process.
[0037] In some embodiments, the composition also comprises one or more ethylenically unsaturated monomers. Those skilled in the art will understand that there are many ethylenically unsaturated monomers that are compatible with the compositions of the present disclosure. For example, in some embodiments, one or more ethylenically unsaturated monomers are selected from methyl methacrylate, acrylic acid, acrylic acid esters, methacrylamide sulfate, acrolein, acrylate, methacrylate, vinyl acetate, acrylonitrile, acrylate, methacrylate, 1,3-butadiene, styrene, isoprene, methacrylic acid, and combinations thereof. In certain embodiments, the composition also comprises vinyl acetate. In certain embodiments, the composition also comprises acrylonitrile. In certain embodiments, the composition also comprises acrylate. In certain embodiments, the composition also comprises methacrylate. In certain embodiments, the composition also comprises 1,3-butadiene. In certain embodiments, the composition also comprises styrene. In certain embodiments, the composition also comprises isoprene. In certain embodiments, the composition also comprises acrylic acid and / or methacrylic acid.
[0038] In some embodiments, the composition does not contain (is excluded from) phenol, nitroxyl radicals, nitroso compounds, or hydroquinones.
[0039] The compositions of this disclosure are stable and remain useful fouling relievers even under acidic conditions. Therefore, the compositions of this disclosure are useful for mitigating polymer fouling during manufacturing processes, particularly during manufacturing processes carried out under acidic conditions. For example, the compositions of this disclosure are useful for preventing polymerization of acrylates, including but not limited to acrylonitrile, acrylic acid, methyl methacrylic acid and their esters, and vinyl acetate.
[0040] In certain embodiments, the compositions of this disclosure are generally stable under acidic conditions. Therefore, in some embodiments, the compositions also include one or more acids. For example, in some embodiments, the compositions also include one or more acids selected from the group consisting of mineral acids and carboxylic acids. Examples of mineral acids include, but are not limited to, hydrochloric acid, hydrofluoric acid, hydrobromic acid, hydroiodic acid, nitric acid, phosphoric acid, sulfuric acid, boric acid, and perchloric acid. Examples of carboxylic acids include, but are not limited to, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, ethaneic acid, caprylic acid, undecylic acid, lauric acid, oxalic acid, acrylic acid, substituted acrylic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, and suberic acid.
[0041] In some embodiments, the compositions of the present disclosure also contain hydrochloric acid. In some embodiments, the compositions of the present disclosure also contain nitric acid. In some embodiments, the compositions of the present disclosure also contain phosphoric acid. In some embodiments, the compositions of the present disclosure also contain sulfuric acid. In some embodiments, the compositions of the present disclosure also contain acetic acid. In some embodiments, the compositions of the present disclosure also contain propionic acid. In some embodiments, the compositions of the present disclosure also contain butyric acid. In some embodiments, the compositions of the present disclosure also contain valeric acid.
[0042] In some embodiments, the composition may be combined with or used together with additional fouling inhibitors, such as hydroquinone, or inhibitors, such as HTEMPO and its derivatives, or phenothiazines, passivators, detergents, transition metal salts, antioxidants, or defoamers, which may be injected together or separately in the methods of the present disclosure.
[0043] Methods using the compositions disclosed herein The Disclosure also relates to a method for mitigating fouling caused by monomer polymerization, comprising adding the composition of the Disclosure to a monomer. In some embodiments, an effective amount of the composition of the Disclosure is added to the monomer, the effective amount being any amount sufficient to mitigate the fouling caused by monomer polymerization.
[0044] In some embodiments, the monomer is an ethylenically unsaturated monomer. In some embodiments, the monomer is disclosed to be an ethylenically unsaturated monomer selected from vinyl acetate, acrylonitrile, acrylate, methacrylate, 1,3-butadiene, styrene, isoprene, (meth)acrylic acid, and combinations thereof. In some embodiments, the methods disclosed herein are useful for inhibiting the polymerization of vinyl acetate. In some embodiments, the methods disclosed herein are useful for inhibiting the polymerization of acrylonitrile. In some embodiments, the methods disclosed herein are useful for inhibiting the polymerization of acrylate. In some embodiments, the methods disclosed herein are useful for inhibiting the polymerization of methacrylate. In some embodiments, the methods disclosed herein are useful for inhibiting the polymerization of 1,3-butadiene. In some embodiments, the methods disclosed herein are useful for inhibiting the polymerization of styrene. In some embodiments, the methods disclosed herein are useful for inhibiting the polymerization of isoprene. In some embodiments, the methods disclosed herein are useful for inhibiting the polymerization of methacrylic acid and / or acrylic acid.
[0045] The compositions of this disclosure can be added to a fluid manually or automatically. The compositions can also be added continuously and / or intermittently. Automatic addition can be achieved by using a chemical injection pump. The chemical injection pump can be programmed to add a specific amount of polymerization inhibitor composition or any of its components to the fluid at certain time intervals. In another embodiment, the chemical injection pump can be manually controlled to add a specific amount of polymerization inhibitor composition or any of its components to the fluid. By adding the polymerization inhibitor compositions of this disclosure to a monomer, the polymerization of the monomer is inhibited.
[0046] In some embodiments, the monomer is provided as a neat liquid. In other embodiments, the monomer is provided in a solution hereafter referred to as the "monomer solution".
[0047] In some embodiments, the monomer solution also includes one or more additional components selected from acids, organic solvents, water, and combinations thereof. For example, in some embodiments, the monomer solution includes one or more organic solvents selected from vinyl acetate, dimethyl phthalate, dimethylformamide, toluene, xylene, highly aromatic naphtha, acetonitrile, ethyl acetate, acetone, dichloromethane, tetrahydrofuran, hexane, dimethyl sulfoxide, N-methyl-2-pyrrolidone, and combinations thereof. In some embodiments, the monomer solution includes one or more acids selected from hydrochloric acid, hydrofluoric acid, hydrobromic acid, hydroiodic acid, nitric acid, phosphoric acid, sulfuric acid, boric acid, perchloric acid, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, caproic acid, ethaneic acid, caprylic acid, undecylic acid, lauric acid, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, and suberic acid. In some embodiments, the monomer solution includes water.
[0048] In some embodiments, the monomer solution has a pH value of about 1 to about 7. In some embodiments, the monomer solution has a pH value of about 1 to about 6. In some embodiments, the monomer solution has a pH value of about 2 to about 6. In some embodiments, the monomer solution has a pH value of about 3 to about 6. In some embodiments, the monomer solution has a pH value of about 4 to about 6. In some embodiments, the monomer solution has a pH value of about 5 to about 6.
[0049] In some embodiments, the compositions are added to the monomer such that the overall concentration of the composition (dispersant, solvant, and accelerator) is approximately 0.01 ppm to 10,000 ppm. Examples of overall composition concentrations, though not limited to these, include approximately 0.01 ppm to 10,000 ppm, approximately 0.01 ppm to 5,000 ppm, approximately 0.01 ppm to 4,000 ppm, approximately 0.01 ppm to 3,000 ppm, approximately 0.01 ppm to 2,000 ppm, approximately 0.01 ppm to 1,000 ppm, approximately 0.01 ppm to 500 ppm, approximately 0.01 ppm to 100 ppm, approximately 0.01 ppm to 50 ppm, and approximately 0.01 ppm to 40 ppm. pm, about 0.01ppm to about 30ppm, about 0.01ppm to about 20ppm, about 0.01ppm to about 10ppm, about 0.01ppm to about 5ppm, about 0.01ppm to about 1ppm, about 0.1ppm to about 10,000ppm, about 0. 1ppm to approximately 5,000ppm, approximately 0.1ppm to approximately 4,000ppm, approximately 0.1ppm to approximately 3,000ppm, approximately 0.1ppm to approximately 2,000ppm, approximately 0.1ppm to approximately 1,000ppm, approximately 0.1ppm to approximately 500ppm, Approximately 0.1 ppm to 100 ppm, approximately 0.1 ppm to 50 ppm, approximately 0.1 ppm to 40 ppm, approximately 0.1 ppm to 30 ppm, approximately 0.1 ppm to 20 ppm, approximately 0.1 ppm to 10 ppm, approximately 0.1 ppm to 5 ppm, approximately 0.1 ppm to 1 ppm, approximately 1 ppm to 10,000 ppm, approximately 1 ppm to 5,000 ppm, approximately 1 ppm to 4,000 ppm, approximately 1 ppm to 3,000 ppm, approximately 1 ppm to 2,000 ppm, approximately 1 ppm ~approximately 1,000 ppm, approximately 1 ppm to approximately 500 ppm, approximately 1 ppm to approximately 100 ppm, approximately 1 ppm to approximately 50 ppm, approximately 1 ppm to approximately 40 ppm, approximately 1 ppm to approximately 30 ppm, approximately 1 ppm to approximately 20 ppm, approximately 1 ppm to approximately 10 ppm, approximately 1 ppm to approximately 5 ppm, approximately 5 ppm to approximately 10,000 ppm, approximately 5 ppm to approximately 5,000 ppm, approximately 5 ppm to approximately 4,000 ppm, approximately 5 ppm to approximately 3,000 ppm, approximately 5 ppm to approximately 2,000 ppm, approximately 5 ppm to approximately 1,000ppm, approximately 5ppm to approximately 500ppm, approximately 5ppm to approximately 100ppm, approximately 5ppm to approximately 50ppm, approximately 5ppm to approximately 40ppm, approximately 5ppm to approximately 30ppm, approximately 5ppm to approximately 20ppm, approximately 5ppm to approximately 10ppm, approximately 10ppm to approximately 10,000ppm, approximately 10ppm to approximately 5,000ppm, approximately 10ppm to approximately 4,000ppm, approximately 10ppm to approximately 3,000ppm, approximately 10ppm to approximately 2,000ppm, approximately 10ppm to approximately 1,000ppm, approximately 10ppm to approximately 500ppm, approximately 10ppm to approximately 100ppm, approximately 10ppm to approximately 50ppm, Approximately 10ppm to 40ppm, approximately 10ppm to 30ppm, approximately 10ppm to 20ppm, approximately 20ppm to 10,000ppm, approximately 20ppm to 5,000ppm, approximately 20ppm to 4,000ppm, approximately 20ppm to 3,000ppm, approximately 20ppm to 2,000ppm, approximately 20ppm to 1,000ppm, approximately 20ppm to 500ppm, approximately 20ppm to 100ppm, approximately 20ppm to 50ppm, approximately 20ppm to 40ppm, approximately 20ppm to 30ppm, approximately 30ppm to 10,000ppm, approximately 30ppm to 5,000ppm 0 ppm, approximately 30 ppm to 4,000 ppm, approximately 30 ppm to 3,000 ppm, approximately 30 ppm to 2,000 ppm, approximately 30 ppm to 1,000 ppm, approximately 30 ppm to 500 ppm, approximately 30 ppm to 100 ppm, approximately 30 ppm to 50 ppm, approximately 30 ppm to 40 ppm, approximately 40 ppm to 10,000 ppm, approximately 40 ppm to 5,000 ppm, approximately 40 ppm to 4,000 ppm, approximately 40 ppm to 3,000 ppm, approximately 40 ppm to 2,000 ppm, approximately 40 ppm to 1,000 ppm, approximately 40 ppm to 500 ppm m, about 40ppm to about 100ppm, about 40ppm to about 50ppm, about 50ppm to about 10,000ppm, about 50ppm to about 5,000ppm, about 50ppm to about 4,000ppm, about 50ppm to about 3,000ppm, about 50ppm to about 2,000ppm, about 50ppm to Approx. 1,000ppm, Approx. 50ppm~Approx. 500ppm, Approx. 50ppm~Approx. 100ppm, Approx. 100ppm~Approx. 10,000ppm, Approx. 100ppm~Approx. 5,000ppm, Approx.000ppm, about 100ppm to about 1,000ppm, about 100ppm to about 500ppm, about 500ppm to about 10,000ppm, about 500ppm m ~ approx. 5,000ppm, approx. 500ppm ~ approx. 4,000ppm, approx. 500ppm ~ approx. 3,000ppm, approx. 500ppm ~ approx. 2,000ppm, Approximately 500ppm to approximately 1,000ppm, approximately 1,000ppm to approximately 10,000ppm, approximately 1,000ppm to approximately 5,000ppm, approximately 1,000p pm ~ approx. 4,000ppm, approx. 1,000ppm ~ approx. 3,000ppm, approx. 1,000ppm ~ approx. 2,000ppm, approx. 2,000 ~ approx. 10,00 Possible values include 0 ppm, approximately 2,000 ppm to 5,000 ppm, approximately 2,000 ppm to 4,000 ppm, approximately 2,000 ppm to 3,000 ppm, approximately 3,000 ppm to 10,000 ppm, approximately 3,000 ppm to 5,000 ppm, approximately 3,000 ppm to 4,000 ppm, approximately 4,000 ppm to 10,000 ppm, approximately 4,000 ppm to 5,000 ppm, approximately 5,000 ppm to 10,000 ppm, approximately 0.01, 0.1, 1, 5, 10, 20, 30, 40, 50, 100, 500, 1,000, 2,000, 3,000, 4,000, or 5,000 ppm.
[0050] The methods of the present disclosure are useful for mitigating fouling caused by premature polymerization of monomers during manufacturing processes, particularly under acidic conditions. For example, the methods of the present disclosure are useful for mitigating fouling caused by polymerization of acrylates, including but not limited to acrylonitrile, acrylic acid, methyl methacrylic acid and their esters, and vinyl acetate.
[0051] Process for preparing the compositions of this disclosure The compositions of this disclosure can be prepared by blending, or by adding each component to a process instrument in situ. Related manufacturing processes may include, for example, methods for producing methyl methacrylate, such as an ACH process, which is an oxidation process that can be divided into four units (methyl methacrylate production unit, esterification unit, purification unit, and waste acid unit). The compositions or components thereof of this disclosure may be injected separately or together.
[0052] In the ACH manufacturing process, three reactive monomers are present: methacrylic acid, methacrylamide sulfate, and methyl methacrylate. All of these monomers readily polymerize, causing fouling problems. Polymerization usually occurs in the same location, resulting in complex and variable fouling problems. Fouling problems often occur in the esterification unit, purification unit, and waste acid unit.
[0053] In some embodiments, additional fouling prevention chemicals, including antioxidants, hydroquinone, phenothiazine, tetramethylpiperidinooxy, inorganic salts, and phenylenediamine, can be added to the reactor. [Examples]
[0054] Example 1 - Miscibility Test Dimethyl phthalate (DMP) was mixed with tall oil hydroxyethylimidazoline in a 50 / 50 mixture, and the two components were mixed by shaking. The tube was allowed to stand for 2 days, after which the two components were separated into separate layers.
[0055] When 45% DMP, 45% tall oil hydroxyethylimidazoline, and 10% dimethacetamide were mixed and allowed to stand, no separation was observed.
[0056] Example 2 - Faurant dissolution test Faurant particles (0.3 g) were added to 15 mL of 30% dimethacetamide / 70% DMP, DMP alone, or 30% dimethacetamide / 70% imidazoline in a test tube. After standing at room temperature for 3 days, Faurant partially dissolved in the dimethacetamide-containing sample but did not dissolve in the DMP-only sample. This indicates that dimethacetamide improves the efficiency of DMP and imidazoline in dissolving Faurant.
[0057] Asphalten faurant particles (0.5 g) were added to 15 mL of 30% dimethacetamide / 70% DMP, 50% dimethacetamide / 50% DMP, DMP alone, or 30% dimethacetamide / 70% imidazoline in test tubes. After standing at room temperature for 3 days, faurant did not dissolve well in DMP but partially dissolved in the other samples. This indicates that dimethacetamide improves the efficiency of DMP and imidazoline in dissolving faurant.
[0058] Example 3 - Dispersion Test The process flow was simulated by adding 0.5 mL of faurant solution to 10 mL of methyl methacrylate. 50 μL of 20% dimethacetamide / 80% DMP, 20% dimethacetamide / 80% imidazoline, or 20% dimethacetamide / 40% DMP / 40% imidazoline were added to separate tubes containing faurant solution and methyl methacrylate. The mixtures were then mixed and allowed to stand for 10 minutes. Dimethacetamide / DMP showed limited dispersion performance, with most of the faurant settling at the bottom, while the other two samples showed more faurant suspended in the liquid. The above results indicate that, although DMP is the solvent for faurant and imidazoline is the dispersant, the two do not mix sufficiently without dimethacetamide, which acts as a solvent booster for faurant, enabling rapid dissolution and suspension of faurant in the process flow.
[0059] All compositions and methods disclosed and claimed herein can be prepared and performed without undue experimentation, taking into consideration this disclosure. The present invention can be embodied in many different forms, and certain preferred embodiments of the present invention are described in detail herein. This disclosure is illustrative of the principles of the present invention and is not intended to limit the present invention to the specific embodiments illustrated. In addition, unless expressly stated otherwise, the term "a" is intended to include "at least one" or "one or more." For example, "a compound" is intended to include "at least one compound" or "one or more compounds."
[0060] Any range given, whether absolute or approximate, is intended to encompass both, and any definitions used herein are intended to clarify, not limit. Numerical ranges and parameters that specify the broad scope of the invention are approximate, but the numerical values specified in specific examples are reported as accurately as possible. However, any numerical value inherently contains a certain degree of error, which is necessarily due to the standard deviation observed in their respective test measurements. Furthermore, all ranges disclosed herein should be understood to encompass all subranges contained therein (including all decimal and total values).
[0061] Any composition disclosed herein may include, consist of, or essentially consist of, any element, component, and / or raw material disclosed herein, or any combination of two or more of the elements, components, or raw materials disclosed herein.
[0062] Any method disclosed herein may include, consist of, or essentially consist of, any method step disclosed herein, or any combination of two or more method steps disclosed herein.
[0063] The transitional phrase "comprising," which is synonymous with "including," "containing," or "characterized by," is either comprehensive or open-ended and does not exclude additional unlisted elements, components, raw materials, and / or process steps.
[0064] The transitional phrase "consisting of" excludes any elements, components, raw materials, and / or process steps not specified in the claims.
[0065] The transitional phrase "consisting essentially of" limits the scope of the claims to specific elements, components, raw materials and / or processes, and does not substantially affect the fundamental and novel features of the claimed invention.
[0066] Unless otherwise specified, all molecular weights mentioned herein are weight-average molecular weights, and all viscosities were measured at 25°C using neat (undiluted) polymers.
[0067] As used herein, the term “approximately” means a cited value that is within the error resulting from the standard deviation found in each of those test measurements, and if those errors cannot be determined, “approximately” may mean, for example, within 5%, 4%, 3%, 2%, or 1% of the cited value.
[0068] Furthermore, the present invention encompasses any possible combination of some or all of the various embodiments described herein. It should also be understood that various changes and modifications to the preferred embodiments of the present invention described herein will be obvious to those skilled in the art. Such changes and modifications can be made without departing from the spirit and scope of the invention and without diminishing its intended advantages. Accordingly, such changes and modifications are intended to be covered by the appended claims.
Claims
1. A composition for mitigating monomer polymerization, wherein the composition is A dispersant containing imidazoline or its derivatives, A solvating agent containing phthalate or its derivative, A composition comprising an accelerator containing an acylamide or a derivative thereof.
2. The imidazoline comprises the compound of formula (I), 【Chemistry 1】 During the ceremony, R is C １ ~C ３０ It is alkylene, R １ 、 R ２ and R ３ are each independently selected from the group consisting of H, C １ to C ３０ alkyl, C ２ to C ３０ alkenyl, C ６ to C ３０ aryl, C １ to C ３０ alkyl-C ６ to C ３０ aryl, C ６ to C ３０ aryl-C １ to C ３０ alkyl, C １ to C ３０ aminoalkyl, and C ６ to C ３０ aminoaryl, and are selected from the group consisting of R ４ is hydrogen, -CH ２ COOH, -(CH ２ ) ２ COOH, -CH ２ CH (CH ３ ) COOH, imidazoline, alcohol, C １ ~C ３０ Ester, C １ ~C ３０ Amides, and C １ ~C ３０ Alkyl-C ６ ~C ３０ Selected from the group consisting of aryls, The composition according to claim 1, wherein n is 1, 2, 3, 4, 5, 6, 7, 8, or 9.
3. R １ , R ２ and R ３ Each of them is hydrogen, n is 0, R ４ The composition according to claim 2, wherein is hydroxyethyl.
4. R is C １ ~C １０ The composition according to claim 2, wherein the composition is alkylene.
5. The composition according to any one of claims 1 to 3, wherein the imidazoline is selected from the group consisting of tall oil hydroxyethylimidazoline and oleate imidazoline.
6. The phthalate comprises the compound of formula (II), 【Chemistry 2】 In the formula, R ５ and R ６ Each of them is independent of C １ ~C １０ Alkyl, C ２ ~C １０ Alkenil, C ６ ~C １０ Ariel, C １ ~C １０ Alkyl-C ６ ~C １０ Ariel, C ６ ~C １０ Aryl-C １ ~C １０ Alkyl, C １ ~C １０ Aminoalkyl, and C ６ ~C １０ A composition according to any one of claims 1 to 5, selected from the group consisting of aminoaryls.
7. The composition according to any one of claims 1 to 6, wherein the phthalate is selected from the group consisting of dimethyl phthalate, diethyl phthalate, and diisobutyl phthalate.
8. The acylamide comprises a compound of formula (III), 【Transformation 3】 In the formula, R ７ , R ８ and R ９ These are, independently, hydrogen and C １ ~C ２０ Alkyl, C ２ ~C ２０ Alkenyl and C ６ ~C ２０ A composition according to any one of claims 1 to 7, selected from the group consisting of aryls.
9. The composition according to any one of claims 1 to 8, wherein the acylamide is selected from the group consisting of dimethylacetamide and N,N-dimethylformamide.
10. The composition according to any one of claims 1 to 9, wherein the accelerator is present in the composition at a concentration of about 0.1% to about 99.9% by weight.
11. The composition according to any one of claims 1 to 10, wherein the accelerator is present in the composition at a concentration of about 10% to about 60% by weight.
12. The composition according to any one of claims 1 to 11, wherein the dispersant and the solvating agent are present in a concentration of about 0.1% by weight to about 99.9% by weight.
13. The composition according to any one of claims 1 to 12, wherein the dispersant and the solvating agent are present in a concentration of about 30% to about 80% by weight.
14. The composition according to any one of claims 1 to 13, wherein the weight ratio of the dispersant to the solvating agent may be about 1:10 to about 10:
1.
15. The composition according to any one of claims 1 to 14, further comprising a monomer.
16. The composition according to claim 15, wherein the monomer is an ethylenically unsaturated monomer.
17. The composition according to claim 15 or 16, wherein the monomer is methacrylic acid, methyl methacrylate, methacrylamide sulfate, acrylic acid, acrylic acid ester, vinyl acetate, or any combination thereof.
18. The composition according to any one of claims 1 to 17, further comprising a polymerization inhibitor or an antioxidant.
19. A method for inhibiting monomer polymerization, wherein the method is A method comprising adding the composition according to any one of claims 1 to 18 to the monomer.
20. The method according to claim 19, wherein the monomer is provided in a solution.
21. The method according to claim 20, wherein the solution further comprises an additional component selected from an acid, an organic solvent, water, and any combination thereof.
22. The method according to any one of claims 19 to 21, wherein the monomer is an ethylenically unsaturated monomer.
23. The method according to any one of claims 19 to 22, wherein the composition is added to the monomer such that the concentration of the composition is about 0.01 ppm to about 10,000 ppm.
24. The method according to any one of claims 19 to 23, wherein the monomer is selected from the group consisting of methyl methacrylate, acrylic acid, acrylic acid ester, methacrylamide sulfate, acrolein, acrylate, methacrylate, vinyl acetate, acrylonitrile, acrylate, methacrylate, 1,3-butadiene, styrene, isoprene, methacrylic acid, and any combination thereof.
25. The method according to any one of claims 19 to 24, wherein the monomer is selected from the group consisting of methacrylic acid, methyl methacrylate, methacrylamide sulfate, acrylic acid, acrylic acid esters, vinyl acetate, and any combination thereof.