The reaction of beta-propiolactone with alpha-and beta-eleostearates and plasticizer properties of derived esters View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

1955-10

AUTHORS

Joan S. Hoffmann, R. T. O'Connor, Frank C. Magne, W. G. Bickford

ABSTRACT

Beta-propiolactone has been employed as the dienophile component in the Diels-Alder reaction withalpha- andbeta-eleostearates, yielding acrylic acid adducts. Catalytic amounts of potassium carbonate were used to induce polymerization ofbeta-propiolac-tone to a polyester and to assist in its pyrolysis to acrylic acid.The ethyl andn-butyl esters of the mixed fatty acids ofalpha-and ofbeta-tung oil, containing about 75% eleostearates, were reacted with the theoretical amount ofbeta-propiolactone at 200°C. for a period of 1.5 hrs. Spectral analyses indicated nearly quantitative conversion of the reactants to the expected Diels-Alder products.The acrylic acid adducts were esterified in their reaction mixtures with the appropriate alcohols to produce the corresponding di-esters. These esters were purified by means of high vacuum distillation.Fractional crystallization of the free acids obtained by saponification of the di-butyl esters of thealpha-eleostearic acid adducts yielded two isomeric dicarboxylic acids, melting at 113°C. and 85°C. These isomers differ only in the position of the carboxyl group on the cyclohexene nucleus of the adduct.The di-ethyl and di-butyl esters of both thealpha-andbeta-eleostearic acid adducts and their hydrogenated derivatives have been intercompared as primary plasticizers for vinyl type resins. The hydrogenated di-esters of thebeta-eleostearic acid adducts were found to be the most effective. More... »

PAGES

533-538

References to SciGraph publications

  • 1953-09. The infrared spectra and the structural relationships between alpha- and beta-eleostearic acids and their maleic anhydride adducts in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1952-06. Determination of the total unsaturation of tung oil by catalytic hydrogenation in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1947-06. The spectrophotometric determination of thealpha andbeta isomers of eleostearic acid in tung oil in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1953-03. Cis, trans isomerism of the eleostearate isomers in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • Identifiers

    URI

    http://scigraph.springernature.com/pub.10.1007/bf02639668

    DOI

    http://dx.doi.org/10.1007/bf02639668

    DIMENSIONS

    https://app.dimensions.ai/details/publication/pub.1001285045


    Indexing Status Check whether this publication has been indexed by Scopus and Web Of Science using the SN Indexing Status Tool
    Incoming Citations Browse incoming citations for this publication using opencitations.net

    JSON-LD is the canonical representation for SciGraph data.

    TIP: You can open this SciGraph record using an external JSON-LD service: JSON-LD Playground Google SDTT

    [
      {
        "@context": "https://springernature.github.io/scigraph/jsonld/sgcontext.json", 
        "about": [
          {
            "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/09", 
            "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
            "name": "Engineering", 
            "type": "DefinedTerm"
          }, 
          {
            "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/0904", 
            "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
            "name": "Chemical Engineering", 
            "type": "DefinedTerm"
          }
        ], 
        "author": [
          {
            "affiliation": {
              "alternateName": "Southern Regional Research Laboratory, New Orleans, Louisiana", 
              "id": "http://www.grid.ac/institutes/grid.507314.4", 
              "name": [
                "Southern Regional Research Laboratory, New Orleans, Louisiana"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Hoffmann", 
            "givenName": "Joan S.", 
            "id": "sg:person.010370476465.17", 
            "sameAs": [
              "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.010370476465.17"
            ], 
            "type": "Person"
          }, 
          {
            "affiliation": {
              "alternateName": "Southern Regional Research Laboratory, New Orleans, Louisiana", 
              "id": "http://www.grid.ac/institutes/grid.507314.4", 
              "name": [
                "Southern Regional Research Laboratory, New Orleans, Louisiana"
              ], 
              "type": "Organization"
            }, 
            "familyName": "O'Connor", 
            "givenName": "R. T.", 
            "id": "sg:person.014534547341.82", 
            "sameAs": [
              "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.014534547341.82"
            ], 
            "type": "Person"
          }, 
          {
            "affiliation": {
              "alternateName": "Southern Regional Research Laboratory, New Orleans, Louisiana", 
              "id": "http://www.grid.ac/institutes/grid.507314.4", 
              "name": [
                "Southern Regional Research Laboratory, New Orleans, Louisiana"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Magne", 
            "givenName": "Frank C.", 
            "id": "sg:person.012476571651.61", 
            "sameAs": [
              "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.012476571651.61"
            ], 
            "type": "Person"
          }, 
          {
            "affiliation": {
              "alternateName": "Southern Regional Research Laboratory, New Orleans, Louisiana", 
              "id": "http://www.grid.ac/institutes/grid.507314.4", 
              "name": [
                "Southern Regional Research Laboratory, New Orleans, Louisiana"
              ], 
              "type": "Organization"
            }, 
            "familyName": "Bickford", 
            "givenName": "W. G.", 
            "id": "sg:person.011212714165.30", 
            "sameAs": [
              "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.011212714165.30"
            ], 
            "type": "Person"
          }
        ], 
        "citation": [
          {
            "id": "sg:pub.10.1007/bf02645650", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1001947948", 
              "https://doi.org/10.1007/bf02645650"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1007/bf02638657", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1034060705", 
              "https://doi.org/10.1007/bf02638657"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1007/bf02593250", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1040135156", 
              "https://doi.org/10.1007/bf02593250"
            ], 
            "type": "CreativeWork"
          }, 
          {
            "id": "sg:pub.10.1007/bf02633774", 
            "sameAs": [
              "https://app.dimensions.ai/details/publication/pub.1024266588", 
              "https://doi.org/10.1007/bf02633774"
            ], 
            "type": "CreativeWork"
          }
        ], 
        "datePublished": "1955-10", 
        "datePublishedReg": "1955-10-01", 
        "description": "Beta-propiolactone has been employed as the dienophile component in the Diels-Alder reaction withalpha- andbeta-eleostearates, yielding acrylic acid adducts. Catalytic amounts of potassium carbonate were used to induce polymerization ofbeta-propiolac-tone to a polyester and to assist in its pyrolysis to acrylic acid.The ethyl andn-butyl esters of the mixed fatty acids ofalpha-and ofbeta-tung oil, containing about 75% eleostearates, were reacted with the theoretical amount ofbeta-propiolactone at 200\u00b0C. for a period of 1.5 hrs. Spectral analyses indicated nearly quantitative conversion of the reactants to the expected Diels-Alder products.The acrylic acid adducts were esterified in their reaction mixtures with the appropriate alcohols to produce the corresponding di-esters. These esters were purified by means of high vacuum distillation.Fractional crystallization of the free acids obtained by saponification of the di-butyl esters of thealpha-eleostearic acid adducts yielded two isomeric dicarboxylic acids, melting at 113\u00b0C. and 85\u00b0C. These isomers differ only in the position of the carboxyl group on the cyclohexene nucleus of the adduct.The di-ethyl and di-butyl esters of both thealpha-andbeta-eleostearic acid adducts and their hydrogenated derivatives have been intercompared as primary plasticizers for vinyl type resins. The hydrogenated di-esters of thebeta-eleostearic acid adducts were found to be the most effective.", 
        "genre": "article", 
        "id": "sg:pub.10.1007/bf02639668", 
        "isAccessibleForFree": false, 
        "isPartOf": [
          {
            "id": "sg:journal.1082739", 
            "issn": [
              "0003-021X", 
              "1558-9331"
            ], 
            "name": "Journal of the American Oil Chemists' Society", 
            "publisher": "Wiley", 
            "type": "Periodical"
          }, 
          {
            "issueNumber": "10", 
            "type": "PublicationIssue"
          }, 
          {
            "type": "PublicationVolume", 
            "volumeNumber": "32"
          }
        ], 
        "keywords": [
          "acid adducts", 
          "acrylic acid", 
          "isomeric dicarboxylic acids", 
          "Diels-Alder reaction", 
          "Diels-Alder products", 
          "high vacuum distillation", 
          "dienophile components", 
          "quantitative conversion", 
          "catalytic amount", 
          "carboxyl groups", 
          "dicarboxylic acid", 
          "appropriate alcohol", 
          "reaction mixture", 
          "type resin", 
          "plasticizer properties", 
          "adducts", 
          "primary plasticizer", 
          "potassium carbonate", 
          "free acid", 
          "vacuum distillation", 
          "theoretical amount", 
          "eleostearate", 
          "esters", 
          "reaction", 
          "acid", 
          "reactants", 
          "isomers", 
          "polyester", 
          "spectral analysis", 
          "propiolactone", 
          "plasticizer", 
          "pyrolysis", 
          "derivatives", 
          "saponification", 
          "carbonate", 
          "crystallization", 
          "resin", 
          "mixture", 
          "conversion", 
          "alcohol", 
          "properties", 
          "amount", 
          "oil", 
          "products", 
          "distillation", 
          "fractional crystallization", 
          "means", 
          "group", 
          "components", 
          "analysis", 
          "position", 
          "alpha", 
          "nucleus", 
          "hr", 
          "period"
        ], 
        "name": "The reaction of beta-propiolactone with alpha-and beta-eleostearates and plasticizer properties of derived esters", 
        "pagination": "533-538", 
        "productId": [
          {
            "name": "dimensions_id", 
            "type": "PropertyValue", 
            "value": [
              "pub.1001285045"
            ]
          }, 
          {
            "name": "doi", 
            "type": "PropertyValue", 
            "value": [
              "10.1007/bf02639668"
            ]
          }
        ], 
        "sameAs": [
          "https://doi.org/10.1007/bf02639668", 
          "https://app.dimensions.ai/details/publication/pub.1001285045"
        ], 
        "sdDataset": "articles", 
        "sdDatePublished": "2022-09-02T16:00", 
        "sdLicense": "https://scigraph.springernature.com/explorer/license/", 
        "sdPublisher": {
          "name": "Springer Nature - SN SciGraph project", 
          "type": "Organization"
        }, 
        "sdSource": "s3://com-springernature-scigraph/baseset/20220902/entities/gbq_results/article/article_71.jsonl", 
        "type": "ScholarlyArticle", 
        "url": "https://doi.org/10.1007/bf02639668"
      }
    ]
     

    Download the RDF metadata as:  json-ld nt turtle xml License info

    HOW TO GET THIS DATA PROGRAMMATICALLY:

    JSON-LD is a popular format for linked data which is fully compatible with JSON.

    curl -H 'Accept: application/ld+json' 'https://scigraph.springernature.com/pub.10.1007/bf02639668'

    N-Triples is a line-based linked data format ideal for batch operations.

    curl -H 'Accept: application/n-triples' 'https://scigraph.springernature.com/pub.10.1007/bf02639668'

    Turtle is a human-readable linked data format.

    curl -H 'Accept: text/turtle' 'https://scigraph.springernature.com/pub.10.1007/bf02639668'

    RDF/XML is a standard XML format for linked data.

    curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1007/bf02639668'


     

    This table displays all metadata directly associated to this object as RDF triples.

    149 TRIPLES      21 PREDICATES      84 URIs      72 LITERALS      6 BLANK NODES

    Subject Predicate Object
    1 sg:pub.10.1007/bf02639668 schema:about anzsrc-for:09
    2 anzsrc-for:0904
    3 schema:author Nc0bb3c4fa8f849e49497fb02352bea50
    4 schema:citation sg:pub.10.1007/bf02593250
    5 sg:pub.10.1007/bf02633774
    6 sg:pub.10.1007/bf02638657
    7 sg:pub.10.1007/bf02645650
    8 schema:datePublished 1955-10
    9 schema:datePublishedReg 1955-10-01
    10 schema:description Beta-propiolactone has been employed as the dienophile component in the Diels-Alder reaction withalpha- andbeta-eleostearates, yielding acrylic acid adducts. Catalytic amounts of potassium carbonate were used to induce polymerization ofbeta-propiolac-tone to a polyester and to assist in its pyrolysis to acrylic acid.The ethyl andn-butyl esters of the mixed fatty acids ofalpha-and ofbeta-tung oil, containing about 75% eleostearates, were reacted with the theoretical amount ofbeta-propiolactone at 200°C. for a period of 1.5 hrs. Spectral analyses indicated nearly quantitative conversion of the reactants to the expected Diels-Alder products.The acrylic acid adducts were esterified in their reaction mixtures with the appropriate alcohols to produce the corresponding di-esters. These esters were purified by means of high vacuum distillation.Fractional crystallization of the free acids obtained by saponification of the di-butyl esters of thealpha-eleostearic acid adducts yielded two isomeric dicarboxylic acids, melting at 113°C. and 85°C. These isomers differ only in the position of the carboxyl group on the cyclohexene nucleus of the adduct.The di-ethyl and di-butyl esters of both thealpha-andbeta-eleostearic acid adducts and their hydrogenated derivatives have been intercompared as primary plasticizers for vinyl type resins. The hydrogenated di-esters of thebeta-eleostearic acid adducts were found to be the most effective.
    11 schema:genre article
    12 schema:isAccessibleForFree false
    13 schema:isPartOf N3f76f2ac526b44a7af5e95f606e2b7ea
    14 Nfc431fb01d704b92ad3095ec6fcee6c5
    15 sg:journal.1082739
    16 schema:keywords Diels-Alder products
    17 Diels-Alder reaction
    18 acid
    19 acid adducts
    20 acrylic acid
    21 adducts
    22 alcohol
    23 alpha
    24 amount
    25 analysis
    26 appropriate alcohol
    27 carbonate
    28 carboxyl groups
    29 catalytic amount
    30 components
    31 conversion
    32 crystallization
    33 derivatives
    34 dicarboxylic acid
    35 dienophile components
    36 distillation
    37 eleostearate
    38 esters
    39 fractional crystallization
    40 free acid
    41 group
    42 high vacuum distillation
    43 hr
    44 isomeric dicarboxylic acids
    45 isomers
    46 means
    47 mixture
    48 nucleus
    49 oil
    50 period
    51 plasticizer
    52 plasticizer properties
    53 polyester
    54 position
    55 potassium carbonate
    56 primary plasticizer
    57 products
    58 properties
    59 propiolactone
    60 pyrolysis
    61 quantitative conversion
    62 reactants
    63 reaction
    64 reaction mixture
    65 resin
    66 saponification
    67 spectral analysis
    68 theoretical amount
    69 type resin
    70 vacuum distillation
    71 schema:name The reaction of beta-propiolactone with alpha-and beta-eleostearates and plasticizer properties of derived esters
    72 schema:pagination 533-538
    73 schema:productId N23ef517e86764a3ab0eb5ffc3a4b5e1b
    74 Ne6745867f8ad49f5a65affc2d164058a
    75 schema:sameAs https://app.dimensions.ai/details/publication/pub.1001285045
    76 https://doi.org/10.1007/bf02639668
    77 schema:sdDatePublished 2022-09-02T16:00
    78 schema:sdLicense https://scigraph.springernature.com/explorer/license/
    79 schema:sdPublisher Nd91d2f480d1745f49596863a4c638fe0
    80 schema:url https://doi.org/10.1007/bf02639668
    81 sgo:license sg:explorer/license/
    82 sgo:sdDataset articles
    83 rdf:type schema:ScholarlyArticle
    84 N23ef517e86764a3ab0eb5ffc3a4b5e1b schema:name doi
    85 schema:value 10.1007/bf02639668
    86 rdf:type schema:PropertyValue
    87 N3e936780bec242839a80a67b005347e9 rdf:first sg:person.012476571651.61
    88 rdf:rest Nae00304a2e2e442b9fd78a3089f3664b
    89 N3ee28c122ebf4feab9d957ba56c79a36 rdf:first sg:person.014534547341.82
    90 rdf:rest N3e936780bec242839a80a67b005347e9
    91 N3f76f2ac526b44a7af5e95f606e2b7ea schema:volumeNumber 32
    92 rdf:type schema:PublicationVolume
    93 Nae00304a2e2e442b9fd78a3089f3664b rdf:first sg:person.011212714165.30
    94 rdf:rest rdf:nil
    95 Nc0bb3c4fa8f849e49497fb02352bea50 rdf:first sg:person.010370476465.17
    96 rdf:rest N3ee28c122ebf4feab9d957ba56c79a36
    97 Nd91d2f480d1745f49596863a4c638fe0 schema:name Springer Nature - SN SciGraph project
    98 rdf:type schema:Organization
    99 Ne6745867f8ad49f5a65affc2d164058a schema:name dimensions_id
    100 schema:value pub.1001285045
    101 rdf:type schema:PropertyValue
    102 Nfc431fb01d704b92ad3095ec6fcee6c5 schema:issueNumber 10
    103 rdf:type schema:PublicationIssue
    104 anzsrc-for:09 schema:inDefinedTermSet anzsrc-for:
    105 schema:name Engineering
    106 rdf:type schema:DefinedTerm
    107 anzsrc-for:0904 schema:inDefinedTermSet anzsrc-for:
    108 schema:name Chemical Engineering
    109 rdf:type schema:DefinedTerm
    110 sg:journal.1082739 schema:issn 0003-021X
    111 1558-9331
    112 schema:name Journal of the American Oil Chemists' Society
    113 schema:publisher Wiley
    114 rdf:type schema:Periodical
    115 sg:person.010370476465.17 schema:affiliation grid-institutes:grid.507314.4
    116 schema:familyName Hoffmann
    117 schema:givenName Joan S.
    118 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.010370476465.17
    119 rdf:type schema:Person
    120 sg:person.011212714165.30 schema:affiliation grid-institutes:grid.507314.4
    121 schema:familyName Bickford
    122 schema:givenName W. G.
    123 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.011212714165.30
    124 rdf:type schema:Person
    125 sg:person.012476571651.61 schema:affiliation grid-institutes:grid.507314.4
    126 schema:familyName Magne
    127 schema:givenName Frank C.
    128 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.012476571651.61
    129 rdf:type schema:Person
    130 sg:person.014534547341.82 schema:affiliation grid-institutes:grid.507314.4
    131 schema:familyName O'Connor
    132 schema:givenName R. T.
    133 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.014534547341.82
    134 rdf:type schema:Person
    135 sg:pub.10.1007/bf02593250 schema:sameAs https://app.dimensions.ai/details/publication/pub.1040135156
    136 https://doi.org/10.1007/bf02593250
    137 rdf:type schema:CreativeWork
    138 sg:pub.10.1007/bf02633774 schema:sameAs https://app.dimensions.ai/details/publication/pub.1024266588
    139 https://doi.org/10.1007/bf02633774
    140 rdf:type schema:CreativeWork
    141 sg:pub.10.1007/bf02638657 schema:sameAs https://app.dimensions.ai/details/publication/pub.1034060705
    142 https://doi.org/10.1007/bf02638657
    143 rdf:type schema:CreativeWork
    144 sg:pub.10.1007/bf02645650 schema:sameAs https://app.dimensions.ai/details/publication/pub.1001947948
    145 https://doi.org/10.1007/bf02645650
    146 rdf:type schema:CreativeWork
    147 grid-institutes:grid.507314.4 schema:alternateName Southern Regional Research Laboratory, New Orleans, Louisiana
    148 schema:name Southern Regional Research Laboratory, New Orleans, Louisiana
    149 rdf:type schema:Organization
     




    Preview window. Press ESC to close (or click here)


    ...