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Features of the acid-catalyzed hydrolysis of mono- and poly(ethylene glycol) methacrylates
[Display omitted] •The resistance of poly(ethylene glycol) methacrylates towards hydrolysis is independent of the ethoxylated chain length.•Nontrivial concentration dependences of the hydrolysis rate are associated with a change in acidity.•Pronounced self-acceleration of hydrolysis with increasing...
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| Published in: | European polymer journal 2018-03, Vol.100, p.18-24 |
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| Main Authors: | , , , |
| Format: | Article |
| Language: | English |
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| cites | cdi_FETCH-LOGICAL-c380t-750f25cb2b2f3b0253b7cb2bf75bbc89e380353dcdf73c1cc9e37fcbbb9011bb3 |
| container_end_page | 24 |
| container_issue | |
| container_start_page | 18 |
| container_title | European polymer journal |
| container_volume | 100 |
| creator | Orekhov, Dmitry V. Kazantsev, Oleg A. Sivokhin, Alexey P. Savinova, Maria V. |
| description | [Display omitted]
•The resistance of poly(ethylene glycol) methacrylates towards hydrolysis is independent of the ethoxylated chain length.•Nontrivial concentration dependences of the hydrolysis rate are associated with a change in acidity.•Pronounced self-acceleration of hydrolysis with increasing conversion is observed when using methacrylic acid as a catalyst.•The hydrolysis kinetics is described by a second order equation.
Hydrolysis of water-soluble industrially important mono- and poly(ethylene glycol) methacrylates catalyzed by sulfuric acid and organic monomeric acids (methacrylic and 2-acrylamido-2-methylpropanesulfonic acid) has been studied in aqueous solutions. Chemical stability of the methacrylates in dilute solutions was found to be independent of the length of ethoxylated fragments. Structurization of the studied solutions and the increase in concentration of hydrogen ions in concentrated solutions of the ethoxylated esters were shown to be the reason for the revealed unusual influence of the initial monomer concentration on the hydrolysis rate. The pronounced self-acceleration effect was observed for the methacrylic acid catalyzed reaction with increase in conversion. |
| doi_str_mv | 10.1016/j.eurpolymj.2018.01.010 |
| format | article |
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•The resistance of poly(ethylene glycol) methacrylates towards hydrolysis is independent of the ethoxylated chain length.•Nontrivial concentration dependences of the hydrolysis rate are associated with a change in acidity.•Pronounced self-acceleration of hydrolysis with increasing conversion is observed when using methacrylic acid as a catalyst.•The hydrolysis kinetics is described by a second order equation.
Hydrolysis of water-soluble industrially important mono- and poly(ethylene glycol) methacrylates catalyzed by sulfuric acid and organic monomeric acids (methacrylic and 2-acrylamido-2-methylpropanesulfonic acid) has been studied in aqueous solutions. Chemical stability of the methacrylates in dilute solutions was found to be independent of the length of ethoxylated fragments. Structurization of the studied solutions and the increase in concentration of hydrogen ions in concentrated solutions of the ethoxylated esters were shown to be the reason for the revealed unusual influence of the initial monomer concentration on the hydrolysis rate. The pronounced self-acceleration effect was observed for the methacrylic acid catalyzed reaction with increase in conversion.</description><identifier>ISSN: 0014-3057</identifier><identifier>EISSN: 1873-1945</identifier><identifier>DOI: 10.1016/j.eurpolymj.2018.01.010</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>2-Acrylamido-2-methylpropanesulfonic acid ; 2-Hydroxyethyl methacrylate ; Acid-catalyzed hydrolysis ; Concentration effect ; Cyclotrons ; Dilution ; Esters ; Hydrogen ions ; Hydrolysis ; Kinetics ; Methacrylic acid ; Organic chemistry ; Poly(ethylene glycol) methacrylates ; Polyethylene glycol ; Structure of a solution ; Sulfuric acid</subject><ispartof>European polymer journal, 2018-03, Vol.100, p.18-24</ispartof><rights>2018 Elsevier Ltd</rights><rights>Copyright Elsevier BV Mar 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c380t-750f25cb2b2f3b0253b7cb2bf75bbc89e380353dcdf73c1cc9e37fcbbb9011bb3</citedby><cites>FETCH-LOGICAL-c380t-750f25cb2b2f3b0253b7cb2bf75bbc89e380353dcdf73c1cc9e37fcbbb9011bb3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Orekhov, Dmitry V.</creatorcontrib><creatorcontrib>Kazantsev, Oleg A.</creatorcontrib><creatorcontrib>Sivokhin, Alexey P.</creatorcontrib><creatorcontrib>Savinova, Maria V.</creatorcontrib><title>Features of the acid-catalyzed hydrolysis of mono- and poly(ethylene glycol) methacrylates</title><title>European polymer journal</title><description>[Display omitted]
•The resistance of poly(ethylene glycol) methacrylates towards hydrolysis is independent of the ethoxylated chain length.•Nontrivial concentration dependences of the hydrolysis rate are associated with a change in acidity.•Pronounced self-acceleration of hydrolysis with increasing conversion is observed when using methacrylic acid as a catalyst.•The hydrolysis kinetics is described by a second order equation.
Hydrolysis of water-soluble industrially important mono- and poly(ethylene glycol) methacrylates catalyzed by sulfuric acid and organic monomeric acids (methacrylic and 2-acrylamido-2-methylpropanesulfonic acid) has been studied in aqueous solutions. Chemical stability of the methacrylates in dilute solutions was found to be independent of the length of ethoxylated fragments. Structurization of the studied solutions and the increase in concentration of hydrogen ions in concentrated solutions of the ethoxylated esters were shown to be the reason for the revealed unusual influence of the initial monomer concentration on the hydrolysis rate. The pronounced self-acceleration effect was observed for the methacrylic acid catalyzed reaction with increase in conversion.</description><subject>2-Acrylamido-2-methylpropanesulfonic acid</subject><subject>2-Hydroxyethyl methacrylate</subject><subject>Acid-catalyzed hydrolysis</subject><subject>Concentration effect</subject><subject>Cyclotrons</subject><subject>Dilution</subject><subject>Esters</subject><subject>Hydrogen ions</subject><subject>Hydrolysis</subject><subject>Kinetics</subject><subject>Methacrylic acid</subject><subject>Organic chemistry</subject><subject>Poly(ethylene glycol) methacrylates</subject><subject>Polyethylene glycol</subject><subject>Structure of a solution</subject><subject>Sulfuric acid</subject><issn>0014-3057</issn><issn>1873-1945</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFUE1LxDAQDaLg-vEbLHjRQ-ukaZvucVlcFRa86MVLSNKp29I2a5IK9debuuJVGBjm8T6YR8gVhYQCLe7aBEe7N93Ut0kKtEyAhoEjsqAlZzFdZvkxWQDQLGaQ81Ny5lwLAJwVbEHeNij9aNFFpo78DiOpmyrW0stu-sIq2k2VDd6u-SH0ZjBxJIcqmgNv0O-mDgeM3rtJm-426gMitZ066dFdkJNadg4vf_c5ed3cv6wf4-3zw9N6tY01K8HHPIc6zbVKVVozBWnOFJ-vmudK6XKJgcVyVumq5kxTrQPCa62UWgKlSrFzcn3w3VvzMaLzojWjHUKkSCEvi6zIOA0sfmBpa5yzWIu9bXppJ0FBzEWKVvwVKeYiBdAwEJSrgxLDE58NWuF0g4PGqrGovahM86_HN_i9grA</recordid><startdate>20180301</startdate><enddate>20180301</enddate><creator>Orekhov, Dmitry V.</creator><creator>Kazantsev, Oleg A.</creator><creator>Sivokhin, Alexey P.</creator><creator>Savinova, Maria V.</creator><general>Elsevier Ltd</general><general>Elsevier BV</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20180301</creationdate><title>Features of the acid-catalyzed hydrolysis of mono- and poly(ethylene glycol) methacrylates</title><author>Orekhov, Dmitry V. ; Kazantsev, Oleg A. ; Sivokhin, Alexey P. ; Savinova, Maria V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c380t-750f25cb2b2f3b0253b7cb2bf75bbc89e380353dcdf73c1cc9e37fcbbb9011bb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>2-Acrylamido-2-methylpropanesulfonic acid</topic><topic>2-Hydroxyethyl methacrylate</topic><topic>Acid-catalyzed hydrolysis</topic><topic>Concentration effect</topic><topic>Cyclotrons</topic><topic>Dilution</topic><topic>Esters</topic><topic>Hydrogen ions</topic><topic>Hydrolysis</topic><topic>Kinetics</topic><topic>Methacrylic acid</topic><topic>Organic chemistry</topic><topic>Poly(ethylene glycol) methacrylates</topic><topic>Polyethylene glycol</topic><topic>Structure of a solution</topic><topic>Sulfuric acid</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Orekhov, Dmitry V.</creatorcontrib><creatorcontrib>Kazantsev, Oleg A.</creatorcontrib><creatorcontrib>Sivokhin, Alexey P.</creatorcontrib><creatorcontrib>Savinova, Maria V.</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>European polymer journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Orekhov, Dmitry V.</au><au>Kazantsev, Oleg A.</au><au>Sivokhin, Alexey P.</au><au>Savinova, Maria V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Features of the acid-catalyzed hydrolysis of mono- and poly(ethylene glycol) methacrylates</atitle><jtitle>European polymer journal</jtitle><date>2018-03-01</date><risdate>2018</risdate><volume>100</volume><spage>18</spage><epage>24</epage><pages>18-24</pages><issn>0014-3057</issn><eissn>1873-1945</eissn><abstract>[Display omitted]
•The resistance of poly(ethylene glycol) methacrylates towards hydrolysis is independent of the ethoxylated chain length.•Nontrivial concentration dependences of the hydrolysis rate are associated with a change in acidity.•Pronounced self-acceleration of hydrolysis with increasing conversion is observed when using methacrylic acid as a catalyst.•The hydrolysis kinetics is described by a second order equation.
Hydrolysis of water-soluble industrially important mono- and poly(ethylene glycol) methacrylates catalyzed by sulfuric acid and organic monomeric acids (methacrylic and 2-acrylamido-2-methylpropanesulfonic acid) has been studied in aqueous solutions. Chemical stability of the methacrylates in dilute solutions was found to be independent of the length of ethoxylated fragments. Structurization of the studied solutions and the increase in concentration of hydrogen ions in concentrated solutions of the ethoxylated esters were shown to be the reason for the revealed unusual influence of the initial monomer concentration on the hydrolysis rate. The pronounced self-acceleration effect was observed for the methacrylic acid catalyzed reaction with increase in conversion.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><doi>10.1016/j.eurpolymj.2018.01.010</doi><tpages>7</tpages></addata></record> |
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| ispartof | European polymer journal, 2018-03, Vol.100, p.18-24 |
| issn | 0014-3057 1873-1945 |
| language | eng |
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| source | ScienceDirect Freedom Collection 2022-2024 |
| subjects | 2-Acrylamido-2-methylpropanesulfonic acid 2-Hydroxyethyl methacrylate Acid-catalyzed hydrolysis Concentration effect Cyclotrons Dilution Esters Hydrogen ions Hydrolysis Kinetics Methacrylic acid Organic chemistry Poly(ethylene glycol) methacrylates Polyethylene glycol Structure of a solution Sulfuric acid |
| title | Features of the acid-catalyzed hydrolysis of mono- and poly(ethylene glycol) methacrylates |
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