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GB743302A - Acrylamides - Google Patents

Acrylamides

Info

Publication number
GB743302A
GB743302A GB28331/53A GB2833153A GB743302A GB 743302 A GB743302 A GB 743302A GB 28331/53 A GB28331/53 A GB 28331/53A GB 2833153 A GB2833153 A GB 2833153A GB 743302 A GB743302 A GB 743302A
Authority
GB
United Kingdom
Prior art keywords
hydracrylamide
hydracrylyl
hydracylamide
thoria
pyrrolidine
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
GB28331/53A
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.)
Celanese Corp
Original Assignee
Celanese Corp
Celanese Corp of America
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 Celanese Corp, Celanese Corp of America filed Critical Celanese Corp
Publication of GB743302A publication Critical patent/GB743302A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Catalysts (AREA)

Abstract

N-substituted acrylamides in which the amide nitrogen is connected to an aliphatic, a cycloaliphatic, an aromatic or a heterocyclic substituent by a carbon to nitrogen bond are prepared by dehydrating the corresponding N-substituted hydracylamides by subjecting them to an elevated temperature in the presence of a catalyst comprising thoria and alumina, preferably activated alumina impregnated with thoria. The catalyst may be used in fixed bed or fluidized form. The dehydration is preferably effected in vapour phase at 200 DEG to 400 DEG C., generally under reduced pressure; polymerization inhibitors may be present. The acrylamides are polymerizable and copolymerizable. In examples (1) N-hydracryl-pyrrolidine is distilled under reduced pressure through a column of thoria on activated alumina maintained at 298 DEG to 320 DEG C. yielding N-acrylyl pyrrolidine; (2) crude N-methyl hydracylamide is dehydrated in like manner yielding N-methyl acrylamide; (3) N-phenyl hydroacrylamide containing hydroquinone is treated likewise yielding N-phenyl acrylamide. Numerous other hydracrylamido starting materials are mentioned including N-isoamyl hydracylamide, N,N-di-t-butyl hydracrylamide, N-dodecyl hydracrylamide, N-dicyclohexyl hydracrylamide, N-(o-chlorophenyl) hydracylamide, N-hydracrylyl piperidine, N-hydracrylyl morpholine, N-(a -pyridyl) hydracrylamide, N-(a -thienyl) hydracrylamide, N - (a - thenyl) - hydracrylamide and N-hydracrylyl-carbazole. N - substituted hydracrylamides are prepared by reacting b -propiolactone with a suitable amine in the presence of water at, preferably, -10 DEG to +50 DEG C. The preparation of N-hydracrylyl pyrrolidine, a new compound, is described in detail.
GB28331/53A 1952-10-16 1953-10-14 Acrylamides Expired GB743302A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US743302XA 1952-10-16 1952-10-16

Publications (1)

Publication Number Publication Date
GB743302A true GB743302A (en) 1956-01-11

Family

ID=22118979

Family Applications (1)

Application Number Title Priority Date Filing Date
GB28331/53A Expired GB743302A (en) 1952-10-16 1953-10-14 Acrylamides

Country Status (1)

Country Link
GB (1) GB743302A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1046608B (en) * 1956-11-14 1958-12-18 Basf Ag Process for the production of acrylic acid amide by splitting off alcohol from low molecular weight ª ‰ -alkoxypropionic acid amides
US2957800A (en) * 1956-12-14 1960-10-25 Spencer Chem Co Nematocidal composition comprising amides of dihalopropionic acids
EP0018629A1 (en) * 1979-05-08 1980-11-12 Chemische Fabrik Stockhausen & Cie. Process for the production of N-substituted acryl amides

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1046608B (en) * 1956-11-14 1958-12-18 Basf Ag Process for the production of acrylic acid amide by splitting off alcohol from low molecular weight ª ‰ -alkoxypropionic acid amides
US2957800A (en) * 1956-12-14 1960-10-25 Spencer Chem Co Nematocidal composition comprising amides of dihalopropionic acids
EP0018629A1 (en) * 1979-05-08 1980-11-12 Chemische Fabrik Stockhausen & Cie. Process for the production of N-substituted acryl amides

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