Acetoxylation of methyl oleate with a resin catalyst View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

1967-05

AUTHORS

L. T. Black, R. E. Beal

ABSTRACT

The reaction of methyl oleate with acetic acid in the presence of a reticulated cation exchange resin produces methyl acetoxystearate. Saponification of this compound and subsequent acidification yields hydroxystearic acid. Time, temperature, acetic acid:ester ratio, and resin:ester ratio were examined for their effect on yield of methyl acetoxystearate. A yield of approximately 45% of theory was reached under the best conditions. The cation exchange resin promoted ester inter-change with the formation of oleic acid, acetoxy-stearic acid, and methyl acetate. An estolide polymer was formed, probably by ester inter-change between acetoxylated methyl oleate and oleic acid. Acetoxy esters were separated from unreacted methyl oleate and ester polymers by fractional distillation. Molecular weight and GLC data substantiate the product structure. Several other short-chain carboxylic acids were reacted with methyl oleate but gave lower yields of acyloxylated product than acetic acid. More... »

PAGES

310-312

References to SciGraph publications

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/bf02635622

DOI

http://dx.doi.org/10.1007/bf02635622

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1049874758


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/2008/0303", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Macromolecular and Materials Chemistry", 
        "type": "DefinedTerm"
      }, 
      {
        "id": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/03", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Chemical Sciences", 
        "type": "DefinedTerm"
      }
    ], 
    "author": [
      {
        "affiliation": {
          "alternateName": "Agricultural Research Service", 
          "id": "https://www.grid.ac/institutes/grid.463419.d", 
          "name": [
            "Northern Regional Research Laboratory, Peoria, Illinois"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Black", 
        "givenName": "L. T.", 
        "id": "sg:person.055753157.81", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.055753157.81"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Agricultural Research Service", 
          "id": "https://www.grid.ac/institutes/grid.463419.d", 
          "name": [
            "Northern Regional Research Laboratory, Peoria, Illinois"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Beal", 
        "givenName": "R. E.", 
        "id": "sg:person.010235772665.55", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.010235772665.55"
        ], 
        "type": "Person"
      }
    ], 
    "citation": [
      {
        "id": "sg:pub.10.1007/bf02544759", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1013361451", 
          "https://doi.org/10.1007/bf02544759"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/bf02642125", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1015178397", 
          "https://doi.org/10.1007/bf02642125"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/bf02639829", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1024170674", 
          "https://doi.org/10.1007/bf02639829"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/bf02612490", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1041590686", 
          "https://doi.org/10.1007/bf02612490"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/bf02645783", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1041616503", 
          "https://doi.org/10.1007/bf02645783"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/bf02639611", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1051518318", 
          "https://doi.org/10.1007/bf02639611"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/i360002a016", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1055529709"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/ie50359a024", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1055625214"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/jo01089a007", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056003302"
        ], 
        "type": "CreativeWork"
      }
    ], 
    "datePublished": "1967-05", 
    "datePublishedReg": "1967-05-01", 
    "description": "The reaction of methyl oleate with acetic acid in the presence of a reticulated cation exchange resin produces methyl acetoxystearate. Saponification of this compound and subsequent acidification yields hydroxystearic acid. Time, temperature, acetic acid:ester ratio, and resin:ester ratio were examined for their effect on yield of methyl acetoxystearate. A yield of approximately 45% of theory was reached under the best conditions. The cation exchange resin promoted ester inter-change with the formation of oleic acid, acetoxy-stearic acid, and methyl acetate. An estolide polymer was formed, probably by ester inter-change between acetoxylated methyl oleate and oleic acid. Acetoxy esters were separated from unreacted methyl oleate and ester polymers by fractional distillation. Molecular weight and GLC data substantiate the product structure. Several other short-chain carboxylic acids were reacted with methyl oleate but gave lower yields of acyloxylated product than acetic acid.", 
    "genre": "research_article", 
    "id": "sg:pub.10.1007/bf02635622", 
    "inLanguage": [
      "en"
    ], 
    "isAccessibleForFree": false, 
    "isPartOf": [
      {
        "id": "sg:journal.1082739", 
        "issn": [
          "0003-021X", 
          "1558-9331"
        ], 
        "name": "Journal of the American Oil Chemists' Society", 
        "type": "Periodical"
      }, 
      {
        "issueNumber": "5", 
        "type": "PublicationIssue"
      }, 
      {
        "type": "PublicationVolume", 
        "volumeNumber": "44"
      }
    ], 
    "name": "Acetoxylation of methyl oleate with a resin catalyst", 
    "pagination": "310-312", 
    "productId": [
      {
        "name": "readcube_id", 
        "type": "PropertyValue", 
        "value": [
          "ed96248aae744ccad25ba1c9c14262e86aa8ca54f701bb784f6a1ec2a9c2abfc"
        ]
      }, 
      {
        "name": "doi", 
        "type": "PropertyValue", 
        "value": [
          "10.1007/bf02635622"
        ]
      }, 
      {
        "name": "dimensions_id", 
        "type": "PropertyValue", 
        "value": [
          "pub.1049874758"
        ]
      }
    ], 
    "sameAs": [
      "https://doi.org/10.1007/bf02635622", 
      "https://app.dimensions.ai/details/publication/pub.1049874758"
    ], 
    "sdDataset": "articles", 
    "sdDatePublished": "2019-04-11T01:06", 
    "sdLicense": "https://scigraph.springernature.com/explorer/license/", 
    "sdPublisher": {
      "name": "Springer Nature - SN SciGraph project", 
      "type": "Organization"
    }, 
    "sdSource": "s3://com-uberresearch-data-dimensions-target-20181106-alternative/cleanup/v134/2549eaecd7973599484d7c17b260dba0a4ecb94b/merge/v9/a6c9fde33151104705d4d7ff012ea9563521a3ce/jats-lookup/v90/0000000001_0000000264/records_8697_00000508.jsonl", 
    "type": "ScholarlyArticle", 
    "url": "http://link.springer.com/10.1007%2FBF02635622"
  }
]
 

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/bf02635622'

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/bf02635622'

Turtle is a human-readable linked data format.

curl -H 'Accept: text/turtle' 'https://scigraph.springernature.com/pub.10.1007/bf02635622'

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

curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1007/bf02635622'


 

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

101 TRIPLES      21 PREDICATES      36 URIs      19 LITERALS      7 BLANK NODES

Subject Predicate Object
1 sg:pub.10.1007/bf02635622 schema:about anzsrc-for:03
2 anzsrc-for:0303
3 schema:author N20510ff2012d409fb81934733ff431c2
4 schema:citation sg:pub.10.1007/bf02544759
5 sg:pub.10.1007/bf02612490
6 sg:pub.10.1007/bf02639611
7 sg:pub.10.1007/bf02639829
8 sg:pub.10.1007/bf02642125
9 sg:pub.10.1007/bf02645783
10 https://doi.org/10.1021/i360002a016
11 https://doi.org/10.1021/ie50359a024
12 https://doi.org/10.1021/jo01089a007
13 schema:datePublished 1967-05
14 schema:datePublishedReg 1967-05-01
15 schema:description The reaction of methyl oleate with acetic acid in the presence of a reticulated cation exchange resin produces methyl acetoxystearate. Saponification of this compound and subsequent acidification yields hydroxystearic acid. Time, temperature, acetic acid:ester ratio, and resin:ester ratio were examined for their effect on yield of methyl acetoxystearate. A yield of approximately 45% of theory was reached under the best conditions. The cation exchange resin promoted ester inter-change with the formation of oleic acid, acetoxy-stearic acid, and methyl acetate. An estolide polymer was formed, probably by ester inter-change between acetoxylated methyl oleate and oleic acid. Acetoxy esters were separated from unreacted methyl oleate and ester polymers by fractional distillation. Molecular weight and GLC data substantiate the product structure. Several other short-chain carboxylic acids were reacted with methyl oleate but gave lower yields of acyloxylated product than acetic acid.
16 schema:genre research_article
17 schema:inLanguage en
18 schema:isAccessibleForFree false
19 schema:isPartOf Neddf663c4c75488ab7c1af598e1abf1f
20 Neff4c79855094298adb3f8f1278af705
21 sg:journal.1082739
22 schema:name Acetoxylation of methyl oleate with a resin catalyst
23 schema:pagination 310-312
24 schema:productId N22fc80c219e8436094d3408dd6f4c4b2
25 Nb42a041e558148fdbcfc080dc1262239
26 Nfd43dee8cfbb4d2bbaeb0b984e4b770f
27 schema:sameAs https://app.dimensions.ai/details/publication/pub.1049874758
28 https://doi.org/10.1007/bf02635622
29 schema:sdDatePublished 2019-04-11T01:06
30 schema:sdLicense https://scigraph.springernature.com/explorer/license/
31 schema:sdPublisher N05f2369ca0934cf09b4de0c2e467353a
32 schema:url http://link.springer.com/10.1007%2FBF02635622
33 sgo:license sg:explorer/license/
34 sgo:sdDataset articles
35 rdf:type schema:ScholarlyArticle
36 N05f2369ca0934cf09b4de0c2e467353a schema:name Springer Nature - SN SciGraph project
37 rdf:type schema:Organization
38 N1d842136aa584e8d8c7b8dec9270ae93 rdf:first sg:person.010235772665.55
39 rdf:rest rdf:nil
40 N20510ff2012d409fb81934733ff431c2 rdf:first sg:person.055753157.81
41 rdf:rest N1d842136aa584e8d8c7b8dec9270ae93
42 N22fc80c219e8436094d3408dd6f4c4b2 schema:name doi
43 schema:value 10.1007/bf02635622
44 rdf:type schema:PropertyValue
45 Nb42a041e558148fdbcfc080dc1262239 schema:name readcube_id
46 schema:value ed96248aae744ccad25ba1c9c14262e86aa8ca54f701bb784f6a1ec2a9c2abfc
47 rdf:type schema:PropertyValue
48 Neddf663c4c75488ab7c1af598e1abf1f schema:volumeNumber 44
49 rdf:type schema:PublicationVolume
50 Neff4c79855094298adb3f8f1278af705 schema:issueNumber 5
51 rdf:type schema:PublicationIssue
52 Nfd43dee8cfbb4d2bbaeb0b984e4b770f schema:name dimensions_id
53 schema:value pub.1049874758
54 rdf:type schema:PropertyValue
55 anzsrc-for:03 schema:inDefinedTermSet anzsrc-for:
56 schema:name Chemical Sciences
57 rdf:type schema:DefinedTerm
58 anzsrc-for:0303 schema:inDefinedTermSet anzsrc-for:
59 schema:name Macromolecular and Materials Chemistry
60 rdf:type schema:DefinedTerm
61 sg:journal.1082739 schema:issn 0003-021X
62 1558-9331
63 schema:name Journal of the American Oil Chemists' Society
64 rdf:type schema:Periodical
65 sg:person.010235772665.55 schema:affiliation https://www.grid.ac/institutes/grid.463419.d
66 schema:familyName Beal
67 schema:givenName R. E.
68 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.010235772665.55
69 rdf:type schema:Person
70 sg:person.055753157.81 schema:affiliation https://www.grid.ac/institutes/grid.463419.d
71 schema:familyName Black
72 schema:givenName L. T.
73 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.055753157.81
74 rdf:type schema:Person
75 sg:pub.10.1007/bf02544759 schema:sameAs https://app.dimensions.ai/details/publication/pub.1013361451
76 https://doi.org/10.1007/bf02544759
77 rdf:type schema:CreativeWork
78 sg:pub.10.1007/bf02612490 schema:sameAs https://app.dimensions.ai/details/publication/pub.1041590686
79 https://doi.org/10.1007/bf02612490
80 rdf:type schema:CreativeWork
81 sg:pub.10.1007/bf02639611 schema:sameAs https://app.dimensions.ai/details/publication/pub.1051518318
82 https://doi.org/10.1007/bf02639611
83 rdf:type schema:CreativeWork
84 sg:pub.10.1007/bf02639829 schema:sameAs https://app.dimensions.ai/details/publication/pub.1024170674
85 https://doi.org/10.1007/bf02639829
86 rdf:type schema:CreativeWork
87 sg:pub.10.1007/bf02642125 schema:sameAs https://app.dimensions.ai/details/publication/pub.1015178397
88 https://doi.org/10.1007/bf02642125
89 rdf:type schema:CreativeWork
90 sg:pub.10.1007/bf02645783 schema:sameAs https://app.dimensions.ai/details/publication/pub.1041616503
91 https://doi.org/10.1007/bf02645783
92 rdf:type schema:CreativeWork
93 https://doi.org/10.1021/i360002a016 schema:sameAs https://app.dimensions.ai/details/publication/pub.1055529709
94 rdf:type schema:CreativeWork
95 https://doi.org/10.1021/ie50359a024 schema:sameAs https://app.dimensions.ai/details/publication/pub.1055625214
96 rdf:type schema:CreativeWork
97 https://doi.org/10.1021/jo01089a007 schema:sameAs https://app.dimensions.ai/details/publication/pub.1056003302
98 rdf:type schema:CreativeWork
99 https://www.grid.ac/institutes/grid.463419.d schema:alternateName Agricultural Research Service
100 schema:name Northern Regional Research Laboratory, Peoria, Illinois
101 rdf:type schema:Organization
 




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


...