Epoxide and cyclic carbonate with diisononyl succinate backbone as phthalate-free plasticizers
[Display omitted] •Epoxidized diisononyl maleate and carbonylated diisononyl tartrate were synthezised.•The synthesis of the cyclic carbonate was scaled up to multi-decagrams.•The performance of the novel materials as phthalate-free plasticizers was tested.•The materials show plasticizing properties...
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| Veröffentlicht in: | Tetrahedron letters 2016-02, Vol.57 (8), p.964-968 |
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| container_title | Tetrahedron letters |
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| creator | Polyakov, Mykola Schäffner, Benjamin Kruse, Daniela Martin, Andreas Köckritz, Angela |
| description | [Display omitted]
•Epoxidized diisononyl maleate and carbonylated diisononyl tartrate were synthezised.•The synthesis of the cyclic carbonate was scaled up to multi-decagrams.•The performance of the novel materials as phthalate-free plasticizers was tested.•The materials show plasticizing properties comparable to phthalate-based plasticizers.
Candidates for new phthalate-free plasticizers are synthesized based on epoxidized diisononyl maleate and carbonylated diisononyl tartrate. Although the carbonation of epoxidized diisononyl maleate with CO2 failed, the cyclic carbonate was synthesized successfully using triphosgene as carbonylation agent of the respective tartrate. The performance of the synthesized materials as plasticizer was analyzed under standard conditions as plastisols. Results showed potential for the epoxidized maleate and carbonylated derivative to be developed into phthalate free-plasticizers. |
| doi_str_mv | 10.1016/j.tetlet.2016.01.069 |
| format | Article |
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•Epoxidized diisononyl maleate and carbonylated diisononyl tartrate were synthezised.•The synthesis of the cyclic carbonate was scaled up to multi-decagrams.•The performance of the novel materials as phthalate-free plasticizers was tested.•The materials show plasticizing properties comparable to phthalate-based plasticizers.
Candidates for new phthalate-free plasticizers are synthesized based on epoxidized diisononyl maleate and carbonylated diisononyl tartrate. Although the carbonation of epoxidized diisononyl maleate with CO2 failed, the cyclic carbonate was synthesized successfully using triphosgene as carbonylation agent of the respective tartrate. The performance of the synthesized materials as plasticizer was analyzed under standard conditions as plastisols. Results showed potential for the epoxidized maleate and carbonylated derivative to be developed into phthalate free-plasticizers.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2016.01.069</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>5-Membered cyclic carbonate ; Carbon dioxide ; Carbonates ; Carbonation ; Carbonyls ; Derivatives ; Epoxidation ; Maleates ; Plasticizer ; Plasticizers ; Triphosgene</subject><ispartof>Tetrahedron letters, 2016-02, Vol.57 (8), p.964-968</ispartof><rights>2016 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c339t-b35831e311c6529d2104f0b4473e093e5176bda1b190260b9bfb81c6f3b43b613</citedby><cites>FETCH-LOGICAL-c339t-b35831e311c6529d2104f0b4473e093e5176bda1b190260b9bfb81c6f3b43b613</cites><orcidid>0000-0003-2208-9993</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tetlet.2016.01.069$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3548,27923,27924,45994</link.rule.ids></links><search><creatorcontrib>Polyakov, Mykola</creatorcontrib><creatorcontrib>Schäffner, Benjamin</creatorcontrib><creatorcontrib>Kruse, Daniela</creatorcontrib><creatorcontrib>Martin, Andreas</creatorcontrib><creatorcontrib>Köckritz, Angela</creatorcontrib><title>Epoxide and cyclic carbonate with diisononyl succinate backbone as phthalate-free plasticizers</title><title>Tetrahedron letters</title><description>[Display omitted]
•Epoxidized diisononyl maleate and carbonylated diisononyl tartrate were synthezised.•The synthesis of the cyclic carbonate was scaled up to multi-decagrams.•The performance of the novel materials as phthalate-free plasticizers was tested.•The materials show plasticizing properties comparable to phthalate-based plasticizers.
Candidates for new phthalate-free plasticizers are synthesized based on epoxidized diisononyl maleate and carbonylated diisononyl tartrate. Although the carbonation of epoxidized diisononyl maleate with CO2 failed, the cyclic carbonate was synthesized successfully using triphosgene as carbonylation agent of the respective tartrate. The performance of the synthesized materials as plasticizer was analyzed under standard conditions as plastisols. Results showed potential for the epoxidized maleate and carbonylated derivative to be developed into phthalate free-plasticizers.</description><subject>5-Membered cyclic carbonate</subject><subject>Carbon dioxide</subject><subject>Carbonates</subject><subject>Carbonation</subject><subject>Carbonyls</subject><subject>Derivatives</subject><subject>Epoxidation</subject><subject>Maleates</subject><subject>Plasticizer</subject><subject>Plasticizers</subject><subject>Triphosgene</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNp9kE1PwzAMhiMEEmPwDzj0yKXFbtquuSChaXxIk7jAlShJXS2ja0uSAePXkzHO-GLZfl_Lfhi7RMgQsLpeZ4FCRyHLY5UBZlCJIzbBesZTXtZ4zCYABaQFcHHKzrxfQ4yqhgl7XYzDl20oUX2TmJ3prEmMcnroVaDk04ZV0ljrh37od13it8bY34lW5i2Kos8n4yqsVBe7aeuIkrFTPlhjv8n5c3bSqs7TxV-espe7xfP8IV0-3T_Ob5ep4VyEVMcrORJHNFWZiyZHKFrQRTHjBIJTibNKNwo1Csgr0EK3uo7aluuC6wr5lF0d9o5ueN-SD3JjvaGuUz0NWy-xBlHloih5lBYHqXGD945aOTq7UW4nEeQep1zLA065xykBZcQZbTcHG8U3Piw56Y2l3lBjHZkgm8H-v-AH8S6BAQ</recordid><startdate>20160224</startdate><enddate>20160224</enddate><creator>Polyakov, Mykola</creator><creator>Schäffner, Benjamin</creator><creator>Kruse, Daniela</creator><creator>Martin, Andreas</creator><creator>Köckritz, Angela</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><orcidid>https://orcid.org/0000-0003-2208-9993</orcidid></search><sort><creationdate>20160224</creationdate><title>Epoxide and cyclic carbonate with diisononyl succinate backbone as phthalate-free plasticizers</title><author>Polyakov, Mykola ; Schäffner, Benjamin ; Kruse, Daniela ; Martin, Andreas ; Köckritz, Angela</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c339t-b35831e311c6529d2104f0b4473e093e5176bda1b190260b9bfb81c6f3b43b613</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>5-Membered cyclic carbonate</topic><topic>Carbon dioxide</topic><topic>Carbonates</topic><topic>Carbonation</topic><topic>Carbonyls</topic><topic>Derivatives</topic><topic>Epoxidation</topic><topic>Maleates</topic><topic>Plasticizer</topic><topic>Plasticizers</topic><topic>Triphosgene</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Polyakov, Mykola</creatorcontrib><creatorcontrib>Schäffner, Benjamin</creatorcontrib><creatorcontrib>Kruse, Daniela</creatorcontrib><creatorcontrib>Martin, Andreas</creatorcontrib><creatorcontrib>Köckritz, Angela</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Polyakov, Mykola</au><au>Schäffner, Benjamin</au><au>Kruse, Daniela</au><au>Martin, Andreas</au><au>Köckritz, Angela</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Epoxide and cyclic carbonate with diisononyl succinate backbone as phthalate-free plasticizers</atitle><jtitle>Tetrahedron letters</jtitle><date>2016-02-24</date><risdate>2016</risdate><volume>57</volume><issue>8</issue><spage>964</spage><epage>968</epage><pages>964-968</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>[Display omitted]
•Epoxidized diisononyl maleate and carbonylated diisononyl tartrate were synthezised.•The synthesis of the cyclic carbonate was scaled up to multi-decagrams.•The performance of the novel materials as phthalate-free plasticizers was tested.•The materials show plasticizing properties comparable to phthalate-based plasticizers.
Candidates for new phthalate-free plasticizers are synthesized based on epoxidized diisononyl maleate and carbonylated diisononyl tartrate. Although the carbonation of epoxidized diisononyl maleate with CO2 failed, the cyclic carbonate was synthesized successfully using triphosgene as carbonylation agent of the respective tartrate. The performance of the synthesized materials as plasticizer was analyzed under standard conditions as plastisols. Results showed potential for the epoxidized maleate and carbonylated derivative to be developed into phthalate free-plasticizers.</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tetlet.2016.01.069</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0003-2208-9993</orcidid></addata></record> |
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| identifier | ISSN: 0040-4039 |
| ispartof | Tetrahedron letters, 2016-02, Vol.57 (8), p.964-968 |
| issn | 0040-4039 1873-3581 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1809629453 |
| source | ScienceDirect Journals (5 years ago - present) |
| subjects | 5-Membered cyclic carbonate Carbon dioxide Carbonates Carbonation Carbonyls Derivatives Epoxidation Maleates Plasticizer Plasticizers Triphosgene |
| title | Epoxide and cyclic carbonate with diisononyl succinate backbone as phthalate-free plasticizers |
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