DE258561C - - Google Patents

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Publication number

DE258561C

DE258561C DENDAT258561D DE258561DA DE258561C DE 258561 C DE258561 C DE 258561C DE NDAT258561 D DENDAT258561 D DE NDAT258561D DE 258561D A DE258561D A DE 258561DA DE 258561 C DE258561 C DE 258561C

Authority

DE

Germany

Prior art keywords

parts

halogen

anthraquinone

ring closure

carried out

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.)

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• 238000000034 method Methods 0.000 claims description 11
• -1 anthraquinone acridones Chemical class 0.000 claims description 4
• 230000031709 bromination Effects 0.000 claims description 4
• 238000005893 bromination reaction Methods 0.000 claims description 4
• 229910052736 halogen Inorganic materials 0.000 claims description 4
• 238000006798 ring closing metathesis reaction Methods 0.000 claims description 4
• PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 3
• 239000003795 chemical substances by application Substances 0.000 claims description 3
• 239000000984 vat dye Substances 0.000 claims description 3
• FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 claims description 2
• NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 claims description 2
• 229940103494 thiosalicylic acid Drugs 0.000 claims description 2
• 150000002367 halogens Chemical class 0.000 claims 3
• RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims 2
• 239000007859 condensation product Substances 0.000 claims 1
• 238000002360 preparation method Methods 0.000 claims 1
• YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims 1
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 10
• 239000000975 dye Substances 0.000 description 7
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
• 229920000742 Cotton Polymers 0.000 description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
• 229910052794 bromium Inorganic materials 0.000 description 4
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
• 238000005660 chlorination reaction Methods 0.000 description 3
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
• QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
• 230000005494 condensation Effects 0.000 description 2
• 238000009833 condensation Methods 0.000 description 2
• 239000000203 mixture Substances 0.000 description 2
• ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
• BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
• 241000131971 Bradyrhizobiaceae Species 0.000 description 1
• RGLYZRRIYJEROG-UHFFFAOYSA-N C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O.C(=O)(O)C1=C(N)C=CC=C1 Chemical class C1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O.C(=O)(O)C1=C(N)C=CC=C1 RGLYZRRIYJEROG-UHFFFAOYSA-N 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
• OAAKZKGKPMPJIF-UHFFFAOYSA-N [Cl].[I] Chemical compound [Cl].[I] OAAKZKGKPMPJIF-UHFFFAOYSA-N 0.000 description 1
• 239000002253 acid Substances 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• GGZQGKZALYVJBJ-UHFFFAOYSA-N anthracene-9,10-dione;thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 GGZQGKZALYVJBJ-UHFFFAOYSA-N 0.000 description 1
• 238000006243 chemical reaction Methods 0.000 description 1
• 229910052801 chlorine Inorganic materials 0.000 description 1
• 239000000460 chlorine Substances 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 238000004043 dyeing Methods 0.000 description 1
• 230000002140 halogenating effect Effects 0.000 description 1
• 230000026030 halogenation Effects 0.000 description 1
• 238000005658 halogenation reaction Methods 0.000 description 1
• 238000010438 heat treatment Methods 0.000 description 1
• 239000000155 melt Substances 0.000 description 1
• 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
• 229940072033 potash Drugs 0.000 description 1
• 235000015320 potassium carbonate Nutrition 0.000 description 1
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
• 239000000843 powder Substances 0.000 description 1
• 239000000126 substance Substances 0.000 description 1

Cited By (1)