DE1266902B - Verfahren zur Herstellung von Sulfonen der Anthrachinonreihe - Google Patents
Verfahren zur Herstellung von Sulfonen der AnthrachinonreiheInfo
- Publication number
- DE1266902B DE1266902B DEF39601A DEF0039601A DE1266902B DE 1266902 B DE1266902 B DE 1266902B DE F39601 A DEF39601 A DE F39601A DE F0039601 A DEF0039601 A DE F0039601A DE 1266902 B DE1266902 B DE 1266902B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- weight
- amino
- sulfones
- anthraquinone
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 11
- 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 title claims description 5
- 150000004056 anthraquinones Chemical class 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000003457 sulfones Chemical class 0.000 title claims description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
- -1 alkaline earth metal salts Chemical class 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 150000003455 sulfinic acids Chemical class 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical class 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000975 dye Substances 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 239000000835 fiber Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- UWIVVFQECQYHOB-UHFFFAOYSA-M sodium;ethanesulfinate Chemical compound [Na+].CCS([O-])=O UWIVVFQECQYHOB-UHFFFAOYSA-M 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- JSJKTONNBRIWSY-UHFFFAOYSA-N 1-amino-4-anilino-2-chloroanthracene-9,10-dione Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(Cl)C=C1NC1=CC=CC=C1 JSJKTONNBRIWSY-UHFFFAOYSA-N 0.000 description 1
- MGLMEXNNLSDBAT-UHFFFAOYSA-N CCCCS(C(C=C(C(C(C1=CC=CC=C11)=O)=C2C1=O)NC1=CC=CC=C1)=C2N)(=O)=O Chemical compound CCCCS(C(C=C(C(C(C1=CC=CC=C11)=O)=C2C1=O)NC1=CC=CC=C1)=C2N)(=O)=O MGLMEXNNLSDBAT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 description 1
- KDHDCVKVBASPRN-UHFFFAOYSA-N NC1=C(C=C(C=2C(C3=CC=CC=C3C(C1=2)=O)=O)NC1=CC=CC=C1)S(=O)(=O)CC Chemical compound NC1=C(C=C(C=2C(C3=CC=CC=C3C(C1=2)=O)=O)NC1=CC=CC=C1)S(=O)(=O)CC KDHDCVKVBASPRN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000221535 Pucciniales Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- AYZPQYKSJYAQRS-UHFFFAOYSA-M potassium;butane-1-sulfinate Chemical compound [K+].CCCCS([O-])=O AYZPQYKSJYAQRS-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ORFSSYGWXNGVFB-UHFFFAOYSA-N sodium 4-amino-6-[[4-[4-[(8-amino-1-hydroxy-5,7-disulfonaphthalen-2-yl)diazenyl]-3-methoxyphenyl]-2-methoxyphenyl]diazenyl]-5-hydroxynaphthalene-1,3-disulfonic acid Chemical compound COC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C3)C(=CC(=C4N)S(=O)(=O)O)S(=O)(=O)O)O)OC)N=NC5=C(C6=C(C=C5)C(=CC(=C6N)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] ORFSSYGWXNGVFB-UHFFFAOYSA-N 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- KFZUDNZQQCWGKF-UHFFFAOYSA-M sodium;4-methylbenzenesulfinate Chemical compound [Na+].CC1=CC=C(S([O-])=O)C=C1 KFZUDNZQQCWGKF-UHFFFAOYSA-M 0.000 description 1
- CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 0.000 description 1
- LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE647171D BE647171A (enrdf_load_stackoverflow) | 1963-04-27 | ||
| DEF39601A DE1266902B (de) | 1963-04-27 | 1963-04-27 | Verfahren zur Herstellung von Sulfonen der Anthrachinonreihe |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF39601A DE1266902B (de) | 1963-04-27 | 1963-04-27 | Verfahren zur Herstellung von Sulfonen der Anthrachinonreihe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1266902B true DE1266902B (de) | 1968-04-25 |
Family
ID=7097845
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF39601A Pending DE1266902B (de) | 1963-04-27 | 1963-04-27 | Verfahren zur Herstellung von Sulfonen der Anthrachinonreihe |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE647171A (enrdf_load_stackoverflow) |
| DE (1) | DE1266902B (enrdf_load_stackoverflow) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE611983A (enrdf_load_stackoverflow) * | 1960-12-24 | |||
| US2995584A (en) * | 1958-12-02 | 1961-08-08 | American Cyanamid Co | Anthraquinonyl sulfones and production thereof |
-
0
- BE BE647171D patent/BE647171A/xx unknown
-
1963
- 1963-04-27 DE DEF39601A patent/DE1266902B/de active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2995584A (en) * | 1958-12-02 | 1961-08-08 | American Cyanamid Co | Anthraquinonyl sulfones and production thereof |
| BE611983A (enrdf_load_stackoverflow) * | 1960-12-24 |
Also Published As
| Publication number | Publication date |
|---|---|
| BE647171A (enrdf_load_stackoverflow) |
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