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/2008/09", 
        "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": "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": "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": "Robert 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": "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": "sg:pub.10.1007/bf02639909", 
        "sameAs": [
          "https://app.dimensions.ai/details/publication/pub.1035202646", 
          "https://doi.org/10.1007/bf02639909"
        ], 
        "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"
      }
    ], 
    "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": "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", 
        "publisher": "Wiley", 
        "type": "Periodical"
      }, 
      {
        "issueNumber": "5", 
        "type": "PublicationIssue"
      }, 
      {
        "type": "PublicationVolume", 
        "volumeNumber": "35"
      }
    ], 
    "keywords": [
      "mercaptoacetic acid", 
      "methyl linoleate", 
      "infrared spectra", 
      "reaction products", 
      "formation of adducts", 
      "catalytic quantities", 
      "functional groups", 
      "characteristic absorption", 
      "dicarboxylic acids", 
      "equimolar quantities", 
      "dimethyl ester", 
      "ethylenic bond", 
      "large excess", 
      "long chain acids", 
      "trimethyl ester", 
      "tricarboxylic acid", 
      "bonds", 
      "reaction", 
      "chemical characteristics", 
      "chain acids", 
      "esters", 
      "azelaic acid", 
      "acid", 
      "conjugation", 
      "linoleate", 
      "products", 
      "catalyst", 
      "spectra", 
      "ozonolysis", 
      "isomerization", 
      "thetrans", 
      "adducts", 
      "thecis", 
      "compounds", 
      "peroxide", 
      "diene conjugation", 
      "identical wavelength", 
      "absorption", 
      "linoleic acid", 
      "formation", 
      "temperature", 
      "addition", 
      "band", 
      "excess", 
      "high degree", 
      "wavelength", 
      "quantity", 
      "erratic rate", 
      "vibration", 
      "group", 
      "degree", 
      "characteristics", 
      "use", 
      "rate", 
      "rise", 
      "sulfur-containing reaction products", 
      "unreacted ethylenic bonds", 
      "unreacted methyl linoleate"
    ], 
    "name": "The reaction of mercaptoacetic acid with methyl linoleate and linoleic acid", 
    "pagination": "225-230", 
    "productId": [
      {
        "name": "dimensions_id", 
        "type": "PropertyValue", 
        "value": [
          "pub.1000167948"
        ]
      }, 
      {
        "name": "doi", 
        "type": "PropertyValue", 
        "value": [
          "10.1007/bf02639831"
        ]
      }
    ], 
    "sameAs": [
      "https://doi.org/10.1007/bf02639831", 
      "https://app.dimensions.ai/details/publication/pub.1000167948"
    ], 
    "sdDataset": "articles", 
    "sdDatePublished": "2022-01-01T18:42", 
    "sdLicense": "https://scigraph.springernature.com/explorer/license/", 
    "sdPublisher": {
      "name": "Springer Nature - SN SciGraph project", 
      "type": "Organization"
    }, 
    "sdSource": "s3://com-springernature-scigraph/baseset/20220101/entities/gbq_results/article/article_72.jsonl", 
    "type": "ScholarlyArticle", 
    "url": "https://doi.org/10.1007/bf02639831"
  }
]
 

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.

138 TRIPLES      22 PREDICATES      86 URIs      76 LITERALS      6 BLANK NODES

Subject Predicate Object
1 sg:pub.10.1007/bf02639831 schema:about anzsrc-for:09
2 anzsrc-for:0904
3 schema:author Nfed2cd83a66b478cae7e77275de1fabd
4 schema:citation sg:pub.10.1007/bf02612064
5 sg:pub.10.1007/bf02639909
6 schema:datePublished 1958-05
7 schema:datePublishedReg 1958-05-01
8 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.
9 schema:genre article
10 schema:inLanguage en
11 schema:isAccessibleForFree false
12 schema:isPartOf N0cbda78738174709b08f6a6e3bd38fa7
13 Nc2996a688b1c48a7ac0bd3b2ecae45f8
14 sg:journal.1082739
15 schema:keywords absorption
16 acid
17 addition
18 adducts
19 azelaic acid
20 band
21 bonds
22 catalyst
23 catalytic quantities
24 chain acids
25 characteristic absorption
26 characteristics
27 chemical characteristics
28 compounds
29 conjugation
30 degree
31 dicarboxylic acids
32 diene conjugation
33 dimethyl ester
34 equimolar quantities
35 erratic rate
36 esters
37 ethylenic bond
38 excess
39 formation
40 formation of adducts
41 functional groups
42 group
43 high degree
44 identical wavelength
45 infrared spectra
46 isomerization
47 large excess
48 linoleate
49 linoleic acid
50 long chain acids
51 mercaptoacetic acid
52 methyl linoleate
53 ozonolysis
54 peroxide
55 products
56 quantity
57 rate
58 reaction
59 reaction products
60 rise
61 spectra
62 sulfur-containing reaction products
63 temperature
64 thecis
65 thetrans
66 tricarboxylic acid
67 trimethyl ester
68 unreacted ethylenic bonds
69 unreacted methyl linoleate
70 use
71 vibration
72 wavelength
73 schema:name The reaction of mercaptoacetic acid with methyl linoleate and linoleic acid
74 schema:pagination 225-230
75 schema:productId N51abc4960a714d5eaf2adf19acf0229a
76 Ne37ed37fdd574600a42f9a199b27a254
77 schema:sameAs https://app.dimensions.ai/details/publication/pub.1000167948
78 https://doi.org/10.1007/bf02639831
79 schema:sdDatePublished 2022-01-01T18:42
80 schema:sdLicense https://scigraph.springernature.com/explorer/license/
81 schema:sdPublisher Nccb5064778a24d44b3f5815ed006f4ce
82 schema:url https://doi.org/10.1007/bf02639831
83 sgo:license sg:explorer/license/
84 sgo:sdDataset articles
85 rdf:type schema:ScholarlyArticle
86 N0cbda78738174709b08f6a6e3bd38fa7 schema:volumeNumber 35
87 rdf:type schema:PublicationVolume
88 N30ed0b5cd72143be8c8da28f32415983 rdf:first sg:person.014534547341.82
89 rdf:rest Na2e49ab82eac47b4859b1b1df0ed73c4
90 N51abc4960a714d5eaf2adf19acf0229a schema:name dimensions_id
91 schema:value pub.1000167948
92 rdf:type schema:PropertyValue
93 Na2e49ab82eac47b4859b1b1df0ed73c4 rdf:first sg:person.062220774.21
94 rdf:rest rdf:nil
95 Nc2996a688b1c48a7ac0bd3b2ecae45f8 schema:issueNumber 5
96 rdf:type schema:PublicationIssue
97 Nccb5064778a24d44b3f5815ed006f4ce schema:name Springer Nature - SN SciGraph project
98 rdf:type schema:Organization
99 Ne37ed37fdd574600a42f9a199b27a254 schema:name doi
100 schema:value 10.1007/bf02639831
101 rdf:type schema:PropertyValue
102 Nfed2cd83a66b478cae7e77275de1fabd rdf:first sg:person.07443054053.51
103 rdf:rest N30ed0b5cd72143be8c8da28f32415983
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.014534547341.82 schema:affiliation grid-institutes:grid.507314.4
116 schema:familyName O'Connor
117 schema:givenName Robert T.
118 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.014534547341.82
119 rdf:type schema:Person
120 sg:person.062220774.21 schema:affiliation grid-institutes:grid.507314.4
121 schema:familyName Goldblatt
122 schema:givenName Leo A.
123 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.062220774.21
124 rdf:type schema:Person
125 sg:person.07443054053.51 schema:affiliation grid-institutes:grid.507314.4
126 schema:familyName Fore
127 schema:givenName Sara P.
128 schema:sameAs https://app.dimensions.ai/discover/publication?and_facet_researcher=ur.07443054053.51
129 rdf:type schema:Person
130 sg:pub.10.1007/bf02612064 schema:sameAs https://app.dimensions.ai/details/publication/pub.1022164594
131 https://doi.org/10.1007/bf02612064
132 rdf:type schema:CreativeWork
133 sg:pub.10.1007/bf02639909 schema:sameAs https://app.dimensions.ai/details/publication/pub.1035202646
134 https://doi.org/10.1007/bf02639909
135 rdf:type schema:CreativeWork
136 grid-institutes:grid.507314.4 schema:alternateName Southern Regional Research Laboratory, New Orleans, Louisiana
137 schema:name Southern Regional Research Laboratory, New Orleans, Louisiana
138 rdf:type schema:Organization
 




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


...