The reaction of mercaptoacetic acid with methyl linoleate and linoleic acid View Full Text


Ontology type: schema:ScholarlyArticle     


Article Info

DATE

1958-05

AUTHORS

Sara P. Fore, Robert T. O'Connor, Leo A. Goldblatt

ABSTRACT

The reaction of mercaptoacetic acid with methyl linoleate and with linoleic acid was investigated. The reaction proceeded at low and erratic rates, with and without catalysts, such as peroxides at various temperatures, but could be accelerated by use of a large excess of mercaptoacetic acid. Addition of 1 mole of mercaptoacetic acid to 1 mole of methyl linoleate resulted in a product containing about 40% of mono-adduct. Ozonolysis of the purified mono-adduct yielded approximately equimolar quantities of caproic and azelaic acids, indicating that addition occurred about equally at the 9,10- and 12,13-ethylenic bonds. The dicarboxylic acid and the dimethyl ester of the mono-adduct and the tricarboxylic acid and trimethyl ester of the di-adduct of linoleic acid and mercaptoacetic acid were prepared, and the infrared spectra and some physical and chemical characteristics of these products were determined. The infrared spectra of the reaction products were obtained and correlated with functional groups which give rise to them. Bands at about 7.8 and 8.8 μ, commonly observed in long chain acids and esters and ascribed to C−O vibrations, are intensified in the sulfur-containing reaction products, suggesting characteristic absorption of C−S compounds at almost identical wavelengths. The formation of adducts was accompanied by a high degree of isomerization of the unreacted ethylenic bonds from thecis to thetrans form both in the mono-adduct and in unreacted methyl linoleate. The methyl linoleate recovered contained about 12% diene conjugation, but catalytic quantities of mercaptoacetic acid were not effective in inducing conjugation. More... »

PAGES

225-230

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/bf02639831

DOI

http://dx.doi.org/10.1007/bf02639831

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1000167948


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/2008/0302", 
        "inDefinedTermSet": "http://purl.org/au-research/vocabulary/anzsrc-for/2008/", 
        "name": "Inorganic 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": [
            "Southern Regional Research Laboratory, New Orleans, Louisiana"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Fore", 
        "givenName": "Sara P.", 
        "id": "sg:person.07443054053.51", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.07443054053.51"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Agricultural Research Service", 
          "id": "https://www.grid.ac/institutes/grid.463419.d", 
          "name": [
            "Southern Regional Research Laboratory, New Orleans, Louisiana"
          ], 
          "type": "Organization"
        }, 
        "familyName": "O'Connor", 
        "givenName": "Robert T.", 
        "id": "sg:person.014534547341.82", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.014534547341.82"
        ], 
        "type": "Person"
      }, 
      {
        "affiliation": {
          "alternateName": "Agricultural Research Service", 
          "id": "https://www.grid.ac/institutes/grid.463419.d", 
          "name": [
            "Southern Regional Research Laboratory, New Orleans, Louisiana"
          ], 
          "type": "Organization"
        }, 
        "familyName": "Goldblatt", 
        "givenName": "Leo A.", 
        "id": "sg:person.062220774.21", 
        "sameAs": [
          "https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.062220774.21"
        ], 
        "type": "Person"
      }
    ], 
    "citation": [
      {
        "id": "https://doi.org/10.1002/cber.19330660904", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1005787873"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/bf02612064", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1022164594", 
          "https://doi.org/10.1007/bf02612064"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "sg:pub.10.1007/bf02639909", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1035202646", 
          "https://doi.org/10.1007/bf02639909"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/ac60046a008", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1055023806"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/ac60063a015", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1055025542"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/ja01162a083", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1055776507"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/ja01559a033", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1055807482"
        ], 
        "type": "CreativeWork"
      }, 
      {
        "id": "https://doi.org/10.1021/jo01159a009", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1056006384"
        ], 
        "type": "CreativeWork"
      }
    ], 
    "datePublished": "1958-05", 
    "datePublishedReg": "1958-05-01", 
    "description": "The reaction of mercaptoacetic acid with methyl linoleate and with linoleic acid was investigated. The reaction proceeded at low and erratic rates, with and without catalysts, such as peroxides at various temperatures, but could be accelerated by use of a large excess of mercaptoacetic acid. Addition of 1 mole of mercaptoacetic acid to 1 mole of methyl linoleate resulted in a product containing about 40% of mono-adduct. Ozonolysis of the purified mono-adduct yielded approximately equimolar quantities of caproic and azelaic acids, indicating that addition occurred about equally at the 9,10- and 12,13-ethylenic bonds. The dicarboxylic acid and the dimethyl ester of the mono-adduct and the tricarboxylic acid and trimethyl ester of the di-adduct of linoleic acid and mercaptoacetic acid were prepared, and the infrared spectra and some physical and chemical characteristics of these products were determined. The infrared spectra of the reaction products were obtained and correlated with functional groups which give rise to them. Bands at about 7.8 and 8.8 \u03bc, commonly observed in long chain acids and esters and ascribed to C\u2212O vibrations, are intensified in the sulfur-containing reaction products, suggesting characteristic absorption of C\u2212S compounds at almost identical wavelengths. The formation of adducts was accompanied by a high degree of isomerization of the unreacted ethylenic bonds from thecis to thetrans form both in the mono-adduct and in unreacted methyl linoleate. The methyl linoleate recovered contained about 12% diene conjugation, but catalytic quantities of mercaptoacetic acid were not effective in inducing conjugation.", 
    "genre": "research_article", 
    "id": "sg:pub.10.1007/bf02639831", 
    "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": "35"
      }
    ], 
    "name": "The reaction of mercaptoacetic acid with methyl linoleate and linoleic acid", 
    "pagination": "225-230", 
    "productId": [
      {
        "name": "readcube_id", 
        "type": "PropertyValue", 
        "value": [
          "00cc360c45f4fdb074daa7acb4550f656a78836ba7cc56bae2e11467ada88764"
        ]
      }, 
      {
        "name": "doi", 
        "type": "PropertyValue", 
        "value": [
          "10.1007/bf02639831"
        ]
      }, 
      {
        "name": "dimensions_id", 
        "type": "PropertyValue", 
        "value": [
          "pub.1000167948"
        ]
      }
    ], 
    "sameAs": [
      "https://doi.org/10.1007/bf02639831", 
      "https://app.dimensions.ai/details/publication/pub.1000167948"
    ], 
    "sdDataset": "articles", 
    "sdDatePublished": "2019-04-10T19:06", 
    "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_8678_00000502.jsonl", 
    "type": "ScholarlyArticle", 
    "url": "http://link.springer.com/10.1007%2FBF02639831"
  }
]
 

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/bf02639831'

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/bf02639831'

Turtle is a human-readable linked data format.

curl -H 'Accept: text/turtle' 'https://scigraph.springernature.com/pub.10.1007/bf02639831'

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

curl -H 'Accept: application/rdf+xml' 'https://scigraph.springernature.com/pub.10.1007/bf02639831'


 

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

101 TRIPLES      21 PREDICATES      35 URIs      19 LITERALS      7 BLANK NODES

Subject Predicate Object
1 sg:pub.10.1007/bf02639831 schema:about anzsrc-for:03
2 anzsrc-for:0302
3 schema:author Needa0c9a07824ea794dd2bc8ba68b169
4 schema:citation sg:pub.10.1007/bf02612064
5 sg:pub.10.1007/bf02639909
6 https://doi.org/10.1002/cber.19330660904
7 https://doi.org/10.1021/ac60046a008
8 https://doi.org/10.1021/ac60063a015
9 https://doi.org/10.1021/ja01162a083
10 https://doi.org/10.1021/ja01559a033
11 https://doi.org/10.1021/jo01159a009
12 schema:datePublished 1958-05
13 schema:datePublishedReg 1958-05-01
14 schema:description The reaction of mercaptoacetic acid with methyl linoleate and with linoleic acid was investigated. The reaction proceeded at low and erratic rates, with and without catalysts, such as peroxides at various temperatures, but could be accelerated by use of a large excess of mercaptoacetic acid. Addition of 1 mole of mercaptoacetic acid to 1 mole of methyl linoleate resulted in a product containing about 40% of mono-adduct. Ozonolysis of the purified mono-adduct yielded approximately equimolar quantities of caproic and azelaic acids, indicating that addition occurred about equally at the 9,10- and 12,13-ethylenic bonds. The dicarboxylic acid and the dimethyl ester of the mono-adduct and the tricarboxylic acid and trimethyl ester of the di-adduct of linoleic acid and mercaptoacetic acid were prepared, and the infrared spectra and some physical and chemical characteristics of these products were determined. The infrared spectra of the reaction products were obtained and correlated with functional groups which give rise to them. Bands at about 7.8 and 8.8 μ, commonly observed in long chain acids and esters and ascribed to C−O vibrations, are intensified in the sulfur-containing reaction products, suggesting characteristic absorption of C−S compounds at almost identical wavelengths. The formation of adducts was accompanied by a high degree of isomerization of the unreacted ethylenic bonds from thecis to thetrans form both in the mono-adduct and in unreacted methyl linoleate. The methyl linoleate recovered contained about 12% diene conjugation, but catalytic quantities of mercaptoacetic acid were not effective in inducing conjugation.
15 schema:genre research_article
16 schema:inLanguage en
17 schema:isAccessibleForFree false
18 schema:isPartOf N2619bf296ed5493aa04dae1e15113b71
19 N638a0c24a7074089aa1cbaa4cd9c2cb7
20 sg:journal.1082739
21 schema:name The reaction of mercaptoacetic acid with methyl linoleate and linoleic acid
22 schema:pagination 225-230
23 schema:productId N19eddccfdf2e464198a2e02d32c219e0
24 Neebf31014c484aa7930c1a2c58781712
25 Nf11fdeee2b0e49828e7429cfd966a2a8
26 schema:sameAs https://app.dimensions.ai/details/publication/pub.1000167948
27 https://doi.org/10.1007/bf02639831
28 schema:sdDatePublished 2019-04-10T19:06
29 schema:sdLicense https://scigraph.springernature.com/explorer/license/
30 schema:sdPublisher N0393ebad70704e22a274b104ddae77ec
31 schema:url http://link.springer.com/10.1007%2FBF02639831
32 sgo:license sg:explorer/license/
33 sgo:sdDataset articles
34 rdf:type schema:ScholarlyArticle
35 N0393ebad70704e22a274b104ddae77ec schema:name Springer Nature - SN SciGraph project
36 rdf:type schema:Organization
37 N19eddccfdf2e464198a2e02d32c219e0 schema:name dimensions_id
38 schema:value pub.1000167948
39 rdf:type schema:PropertyValue
40 N2619bf296ed5493aa04dae1e15113b71 schema:volumeNumber 35
41 rdf:type schema:PublicationVolume
42 N630747c9188b4f23b93b95f9cacb2f05 rdf:first sg:person.014534547341.82
43 rdf:rest Nf67d0acb92634e31a013e5c1917209e5
44 N638a0c24a7074089aa1cbaa4cd9c2cb7 schema:issueNumber 5
45 rdf:type schema:PublicationIssue
46 Neebf31014c484aa7930c1a2c58781712 schema:name doi
47 schema:value 10.1007/bf02639831
48 rdf:type schema:PropertyValue
49 Needa0c9a07824ea794dd2bc8ba68b169 rdf:first sg:person.07443054053.51
50 rdf:rest N630747c9188b4f23b93b95f9cacb2f05
51 Nf11fdeee2b0e49828e7429cfd966a2a8 schema:name readcube_id
52 schema:value 00cc360c45f4fdb074daa7acb4550f656a78836ba7cc56bae2e11467ada88764
53 rdf:type schema:PropertyValue
54 Nf67d0acb92634e31a013e5c1917209e5 rdf:first sg:person.062220774.21
55 rdf:rest rdf:nil
56 anzsrc-for:03 schema:inDefinedTermSet anzsrc-for:
57 schema:name Chemical Sciences
58 rdf:type schema:DefinedTerm
59 anzsrc-for:0302 schema:inDefinedTermSet anzsrc-for:
60 schema:name Inorganic Chemistry
61 rdf:type schema:DefinedTerm
62 sg:journal.1082739 schema:issn 0003-021X
63 1558-9331
64 schema:name Journal of the American Oil Chemists' Society
65 rdf:type schema:Periodical
66 sg:person.014534547341.82 schema:affiliation https://www.grid.ac/institutes/grid.463419.d
67 schema:familyName O'Connor
68 schema:givenName Robert T.
69 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.014534547341.82
70 rdf:type schema:Person
71 sg:person.062220774.21 schema:affiliation https://www.grid.ac/institutes/grid.463419.d
72 schema:familyName Goldblatt
73 schema:givenName Leo A.
74 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.062220774.21
75 rdf:type schema:Person
76 sg:person.07443054053.51 schema:affiliation https://www.grid.ac/institutes/grid.463419.d
77 schema:familyName Fore
78 schema:givenName Sara P.
79 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.07443054053.51
80 rdf:type schema:Person
81 sg:pub.10.1007/bf02612064 schema:sameAs https://app.dimensions.ai/details/publication/pub.1022164594
82 https://doi.org/10.1007/bf02612064
83 rdf:type schema:CreativeWork
84 sg:pub.10.1007/bf02639909 schema:sameAs https://app.dimensions.ai/details/publication/pub.1035202646
85 https://doi.org/10.1007/bf02639909
86 rdf:type schema:CreativeWork
87 https://doi.org/10.1002/cber.19330660904 schema:sameAs https://app.dimensions.ai/details/publication/pub.1005787873
88 rdf:type schema:CreativeWork
89 https://doi.org/10.1021/ac60046a008 schema:sameAs https://app.dimensions.ai/details/publication/pub.1055023806
90 rdf:type schema:CreativeWork
91 https://doi.org/10.1021/ac60063a015 schema:sameAs https://app.dimensions.ai/details/publication/pub.1055025542
92 rdf:type schema:CreativeWork
93 https://doi.org/10.1021/ja01162a083 schema:sameAs https://app.dimensions.ai/details/publication/pub.1055776507
94 rdf:type schema:CreativeWork
95 https://doi.org/10.1021/ja01559a033 schema:sameAs https://app.dimensions.ai/details/publication/pub.1055807482
96 rdf:type schema:CreativeWork
97 https://doi.org/10.1021/jo01159a009 schema:sameAs https://app.dimensions.ai/details/publication/pub.1056006384
98 rdf:type schema:CreativeWork
99 https://www.grid.ac/institutes/grid.463419.d schema:alternateName Agricultural Research Service
100 schema:name Southern Regional Research Laboratory, New Orleans, Louisiana
101 rdf:type schema:Organization
 




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


...