GB441457A - Organic condensation products and their manufacture - Google Patents

Organic condensation products and their manufacture

Info

Publication number
GB441457A
GB441457A GB11427/34A GB1142734A GB441457A GB 441457 A GB441457 A GB 441457A GB 11427/34 A GB11427/34 A GB 11427/34A GB 1142734 A GB1142734 A GB 1142734A GB 441457 A GB441457 A GB 441457A
Authority
GB
United Kingdom
Prior art keywords
yield
product
monovinylacetylene
products
mercaptan
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB11427/34A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to GB11427/34A priority Critical patent/GB441457A/en
Publication of GB441457A publication Critical patent/GB441457A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
    • C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/18—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by addition of thiols to unsaturated compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Addition products are obtained by the reaction of compounds containing an alcoholic hydroxy group, or aliphatic or aromatic mercaptans, with hydrocarbons containing conjugated unsaturated linkages, one at least of which is an acetylenic linkage. Specified hydrocarbons are mono- and di-vinylacetylene. The hydroxy compounds treated may be primary, secondary or tertiary monohydric alcohols or their substitution products, such as aminoalcohols, or polyhydric alcohols or derivatives thereof such as partly esterified polyhydric alcohols and esters of hydroxy acids; specified hydroxy compounds are methanol, ethanol, isopropanol, n-butanol, tertiary butanol, benzyl alcohol, cyclohexanol, ethylene glycol and its monomethyl ether, diethylene glycol, glycerol, dimethyldimethylolmethane, monoethylin, monobenzylin, mannitol, sugars, starch and cellulose. Specified mercaptans are thiocresols, benzyl mercaptan, n-butyl mercaptan, diethylthiocarbinol, cyclohexyl mercaptan, mono- and di-thioglycols, and thioglycollic acid. The reaction of an alcohol ROH with monovinylacetylene is believed to yield first a diolefinic ether CH2 : C : CHCH2OR, which is then converted into an acetylenic ether CH3C­CCH2OR; the reaction with divinylacetylene is believed to yield a triolefinic ether CH3CH : C : C(OR) CH : CH2; in each case, addition products from two mols. of alcohol and one of hydrocarbon are also obtainable. The products are useful as perfume ingredients, solvents, insecticide ingredients, and plasticizers; the mercaptan addition products are useful as "rubber chemicals." In the examples: (1) methanol containing p dissolved sodium is heated with monovinylacetylene to yield a product of the probable formula CH3C­CCH2OCH3, which yields methyl n-butyl ether on reduction; (2) ethanol and monovinylacetylene, reacted as in example 1, yield a similar product which gives ethyl n-butyl ether on reduction; (3) butanol and monovinylacetylene are reacted as in example 1 to yield a product of unstated constitution; (4) benzyl alcohol and monovinylacetylene are reacted as in example 1 to yield an addition product and a resinous by-product; (5) ethylene glycol and monovinylacetylene are reacted as in example 1 to yield an equimolecular addition product and a resinous by-product; (6) cyclohexanol or (example 7) ethylene glycol monomethyl ether or (example 8) isopropanol, or (example 9) tertiary butanol is reacted with monovinylacetylene as in example 1; addition products of unspecified constitution are obtained; (10) methanol containing sodium methylate is heated with divinylacetylene to yield methoxy - 4 - hexatriene - 2 : 3 : 5; (11) methanol and divinylacetylene are reacted as in example 10, but for a longer time; an addition product from two mols. of alcohol and one of hydrocarbon is obtained, as well as the product of example 10; (12) a mixture of p - thiocresol and monovinylacetylene is irradiated with an electric lamp to yield products of the probable formul CH3C6H4SCH2CH2C­CH, (CH3C6H4SH)2C4H4, and (CH3C6H4SH)3C4H4; (13) a mixture of benzyl mercaptan and monovinylacetylene is irradiated with artificial light to yield a product of the formula C6H5CH2SH.C4H4 and other products of higher boiling point; (14) a mixture of p-thiocresol and divinylacetylene is allowed to stand; a product of the formula <FORM:0441457/IV/1> is obtained.ALSO:Products useful as "rubber chemicals" are obtained by the reaction of aliphatic or aromatic mercaptans with hydrocarbons containing conjugated unsaturated linkages, one at least of which is an acetylenic linkage. Specified mercaptans are thiocresols, benzyl mercaptan, n-butyl mercaptan, diethylthiocarbinol, cyclohexyl mercaptan, mono- and di-thioglycols, and thioglycollic acid. Examples are given in which (1) p-thiocresol and monovinylacetylene yield products of the probable formul CH3C6H4SCH2CH2C= CH,(CH3C6H4SH)2C4H4, and (CH3C6H4SH)3C4H4; (2) benzyl mercaptan and monovinylacetylene yield a product of the formula C6H5CH2SHC4H4; (3) p-thiocresol and divinylacetylene yield a product of the formula CH3C6H4SCH2CH2C= CCH2CH2SC6H4CH3.
GB11427/34A 1934-04-16 1934-04-16 Organic condensation products and their manufacture Expired GB441457A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB11427/34A GB441457A (en) 1934-04-16 1934-04-16 Organic condensation products and their manufacture

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB11427/34A GB441457A (en) 1934-04-16 1934-04-16 Organic condensation products and their manufacture

Publications (1)

Publication Number Publication Date
GB441457A true GB441457A (en) 1936-01-20

Family

ID=9986029

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11427/34A Expired GB441457A (en) 1934-04-16 1934-04-16 Organic condensation products and their manufacture

Country Status (1)

Country Link
GB (1) GB441457A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2570697A1 (en) * 1984-09-25 1986-03-28 Elf Aquitaine NOVEL HYDROXY-THIA ALKENES, PROCESS FOR THEIR PREPARATION AND APPLICATIONS

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2570697A1 (en) * 1984-09-25 1986-03-28 Elf Aquitaine NOVEL HYDROXY-THIA ALKENES, PROCESS FOR THEIR PREPARATION AND APPLICATIONS
EP0176438A1 (en) * 1984-09-25 1986-04-02 Societe Nationale Elf Aquitaine Hydroxy-thia-alcanes, process for their preparation and their uses
US4847420A (en) * 1984-09-25 1989-07-11 Societe Nationale Elf Aquitaine New hydroxy-thia-alkenes, and processes for their preparation and use

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