GB788725A - New compounds of selenium and process for making them - Google Patents

New compounds of selenium and process for making them

Info

Publication number
GB788725A
GB788725A GB19243/54A GB1924354A GB788725A GB 788725 A GB788725 A GB 788725A GB 19243/54 A GB19243/54 A GB 19243/54A GB 1924354 A GB1924354 A GB 1924354A GB 788725 A GB788725 A GB 788725A
Authority
GB
United Kingdom
Prior art keywords
give
anthraquinone
reacted
acetate
group
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
GB19243/54A
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.)
BASF Schweiz AG
Original Assignee
Ciba AG
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 Ciba AG filed Critical Ciba AG
Publication of GB788725A publication Critical patent/GB788725A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C391/00Compounds containing selenium
    • C07C391/02Compounds containing selenium having selenium atoms bound to carbon atoms of six-membered aromatic rings
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/007Seleno-anthraquinones

Landscapes

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

Abstract

The invention comprises selenium compounds of the formula A-Se-R, in which A represents an aromatic residue and R one of the radicals <FORM:0788725/IV (b)/1> in which both X1's, together with the -C-C-group, represent a cycloalkyl radical, X2 represents a phenyl radical or an alkyl group, X3 and X4 each represents an alkyl group, both X5's, together with the -C-C-group, represent a pyrane radical, and Y represents an acyl group or a hydroxyl group, and also a method of making such compounds by reacting a compound of the formula: A-Se-O-Acyl with an unsaturated organic compound and, if desired, a resulting compound containing an O-acyl group is reacted with a hydrolysing agent, or carboxylic acid may be split off to give an unsaturated compound. A may be a vattable residue, e.g. an anthraquinone residue, attached to selenium in a -position, and may contain alkoxy groups. The products dye or print cellulose acetate, or nylon. Unsaturated compounds specified are ethylene, vinyl acetate, allyl bromide, isobutylene, butadiene, styrene, 1 - methyl - 2 - phenylethylene, 1 - methyl - 1-phenyl-ethylene, cyclohexene, dihydropyrane. The compounds of the formula A-Se-O-Acyl may be prepared (1) from compounds of the formula A-Se-O-Alkyl by reaction with the acid from which the acyl residue is derived, or (2) from a compound A-Se-Halogen and a salt of said acid. In examples, anthraquinone - 1 - selenenic acid methyl ester is boiled with glacial acetic acid to give anthraquinone-1-selenenyl acetate which is reacted with (1) cyclohexene, to give 1-(21-acetoxy - cyclohexylselenyl) - anthraquinone, which is hydrolysed with alcoholic potash to remove the hydroxy group, (2) styrene, to give 21 - acetoxy - 21 - phenyl - ethylselenyl - anthraquinone, (3) vinyl acetate, to give an ethylidene diacetate, (4) 1-methyl-1-phenylethylene, (5) isobutylene, (6) ethylene, (7) dihydropyrane, (8) butadiene-1,3. Also in examples, (9) 1-methoxyanthraquinone - 4 - selenenyl bromide is reacted with acetic acid to give 1-methoxyanthraquinone - 4 - selenenyl acetate which is reacted with cyclohexene, (10) 1-hydroxyanthraquinone-4-selenenyl acetate is reacted with vinyl acetate, (11) 1-nitrobenzene-2-selenenyl acetate is reacted with vinyl acetate to give a compound of the formula: <FORM:0788725/IV (b)/2> A dyeing example is given.ALSO:The invention comprises selenium compounds of the formula A-Se-R, in which A represents an aromatic residue and R one of the radicals: <FORM:0788725/IV (b)/1> in which both X1's, together with the -C-C-group, represent a cycloalkyl radical, X2 represents a phenyl radical or an alkyl group, X3 and X4 each represents an alkyl group, both X'5s, together with the -C=C- group represent a pyrane radical, and Y represents an acyl group or an hydroxyl group, and also a method of making such compounds by reacting a compound of the formula: A-Se-O-Acyl with an unsaturated organic compound and, if desired, a resulting compound containing an O-acyl group is reacted with a hydrolysing agent, or carboxylic acid may be split off to give an unsaturated compound. A may be a vattable residue, e.g. an anthraquinone residue, attached to selenium in a -position and may contain alkoxy groups. The products dye or print cellulose acetate, or nylon. Unsaturated compounds specified are ethylene, vinyl acetate, allyl bromide, isobutylene, butadiene, styrene, 1 - methyl - 2 - phenylethylene, 1 - methyl - 1-phenyl-ethylene, cyclohexene, dihydropyrane. The compounds of the formula A-Se-O-Acyl may be prepared (1) from compounds of the formula A-Se-O-Alkyl by reaction with the acid from which the acyl residue is derived, or (2) from a compound A-Se-Halogen and a salt of said acid. In examples, anthraquinone-1-selenenic acid methyl ester is boiled with glacial acetic acid to give anthraquinone-1-selenenyl acetate which is reacted with (1) cyclohexene, to give 1 - (21 - acetoxycyclohexylselenyl) - anthraquinone, which is hydrolysed with alcoholic potash to remove the hydroxy group; (2) styrene, to give 21-acetoxy-21 - phenyl - ethylselenyl - anthraquinone; (3) vinyl acetate, to give an ethylidene diacetate; (4) 1 - methyl - 1 - phenylethylene; (5) isobutylene; (6) ethylene; (7) dihydropyrane; (8) butadiene-1.3. Also in examples: (9) 1-methoxyanthraquinone - 4 - selenenyl bromide is reacted with acetic acid to give 1-methoxy-anthraquinone - 4 - selenenyl acetate which is reacted with cyclohexene; (10) 1-hydroxy-anthraquinone - 4 - selenenyl acetate is reacted with vinyl acetate; (11) 1-nitrobenzene-2-selenenyl acetate is reacted with vinyl acetate to give a compound of the formula: <FORM:0788725/IV (b)/2> A dyeing example is given.
GB19243/54A 1953-07-01 1954-06-30 New compounds of selenium and process for making them Expired GB788725A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH788725X 1953-07-01

Publications (1)

Publication Number Publication Date
GB788725A true GB788725A (en) 1958-01-08

Family

ID=4536795

Family Applications (1)

Application Number Title Priority Date Filing Date
GB19243/54A Expired GB788725A (en) 1953-07-01 1954-06-30 New compounds of selenium and process for making them

Country Status (4)

Country Link
CH (1) CH322623A (en)
DE (1) DE1015447B (en)
FR (1) FR1103317A (en)
GB (1) GB788725A (en)

Also Published As

Publication number Publication date
FR1103317A (en) 1955-11-02
CH322623A (en) 1957-06-30
DE1015447B (en) 1957-09-12

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