DE2825246C2 - Herstellung quartaerer Sulfoalkylsalze - Google Patents
Herstellung quartaerer SulfoalkylsalzeInfo
- Publication number
- DE2825246C2 DE2825246C2 DE2825246A DE2825246A DE2825246C2 DE 2825246 C2 DE2825246 C2 DE 2825246C2 DE 2825246 A DE2825246 A DE 2825246A DE 2825246 A DE2825246 A DE 2825246A DE 2825246 C2 DE2825246 C2 DE 2825246C2
- Authority
- DE
- Germany
- Prior art keywords
- quaternary
- salts
- sulfoalkyl
- water
- methyl
- 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
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 125000004964 sulfoalkyl group Chemical group 0.000 title description 7
- 238000000034 method Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 150000002431 hydrogen Chemical class 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- -1 compound Acetic anhydride Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- WQPMYSHJKXVTME-UHFFFAOYSA-N 3-hydroxypropane-1-sulfonic acid Chemical compound OCCCS(O)(=O)=O WQPMYSHJKXVTME-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000008053 sultones Chemical class 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- LZRLJNWXUOYVKN-UHFFFAOYSA-N 1,3-benzoxazole hydrate Chemical compound [OH-].O1C=[NH+]C2=C1C=CC=C2 LZRLJNWXUOYVKN-UHFFFAOYSA-N 0.000 description 1
- WMEPIQQSGOIFIO-UHFFFAOYSA-N 1,3-thiazol-3-ium;hydroxide Chemical compound O.C1=CSC=N1 WMEPIQQSGOIFIO-UHFFFAOYSA-N 0.000 description 1
- RYOLJRRNBRXUCN-UHFFFAOYSA-N 1h-pyrrole;hydrate Chemical compound O.C=1C=CNC=1 RYOLJRRNBRXUCN-UHFFFAOYSA-N 0.000 description 1
- ZZLZXZFVVOXVRG-UHFFFAOYSA-N 2,5,6-trimethyl-1,3-benzothiazole Chemical compound CC1=C(C)C=C2SC(C)=NC2=C1 ZZLZXZFVVOXVRG-UHFFFAOYSA-N 0.000 description 1
- RBDZTYJFIHAYLE-UHFFFAOYSA-M 2-(2-chloroprop-1-enyl)-3-ethyl-1,3-benzothiazol-3-ium;chloride Chemical compound [Cl-].C1=CC=C2[N+](CC)=C(C=C(C)Cl)SC2=C1 RBDZTYJFIHAYLE-UHFFFAOYSA-M 0.000 description 1
- YEGPVWSPNYPPIK-UHFFFAOYSA-N 4-hydroxybutane-1-sulfonic acid Chemical compound OCCCCS(O)(=O)=O YEGPVWSPNYPPIK-UHFFFAOYSA-N 0.000 description 1
- PWMWNNDLYISLDO-UHFFFAOYSA-M OC(CS(=O)(=O)[O-])C.[K+] Chemical compound OC(CS(=O)(=O)[O-])C.[K+] PWMWNNDLYISLDO-UHFFFAOYSA-M 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 235000019992 sake Nutrition 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- CSKVLUWCGPWCQR-UHFFFAOYSA-M sodium;3-hydroxypropane-1-sulfonate Chemical compound [Na+].OCCCS([O-])(=O)=O CSKVLUWCGPWCQR-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D293/00—Heterocyclic compounds containing rings having nitrogen and selenium or nitrogen and tellurium, with or without oxygen or sulfur atoms, as the ring hetero atoms
- C07D293/10—Heterocyclic compounds containing rings having nitrogen and selenium or nitrogen and tellurium, with or without oxygen or sulfur atoms, as the ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D293/12—Selenazoles; Hydrogenated selenazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB24299/77A GB1593082A (en) | 1977-06-10 | 1977-06-10 | Preparation of sulphoalkyl quaternary salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2825246A1 DE2825246A1 (de) | 1978-12-14 |
| DE2825246C2 true DE2825246C2 (de) | 1981-12-10 |
Family
ID=10209501
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2825246A Expired DE2825246C2 (de) | 1977-06-10 | 1978-06-08 | Herstellung quartaerer Sulfoalkylsalze |
Country Status (7)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0222970A1 (de) * | 1985-11-21 | 1987-05-27 | Agfa-Gevaert AG | Sulfoalkylierungsverfahren |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2803493A1 (de) * | 1978-01-27 | 1979-08-02 | Agfa Gevaert Ag | Verfahren zur herstellung von sulfoalkylquartaersalzen |
| DE3010427A1 (de) * | 1980-03-19 | 1981-09-24 | Agfa-Gevaert Ag, 5090 Leverkusen | Verfahren zur herstellung von sulfoalkylquartaersalzen |
| JPS5776335U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1980-10-29 | 1982-05-11 | ||
| DE3118374A1 (de) * | 1981-05-09 | 1982-11-25 | Agfa-Gevaert Ag, 5090 Leverkusen | Verfahren zur herstellung von sulfoalkylquartaersalzen |
| US7214825B2 (en) | 2003-10-17 | 2007-05-08 | Honeywell International Inc. | O-(3-chloropropenyl) hydroxylamine free base |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2503776A (en) * | 1947-03-21 | 1950-04-11 | Eastman Kodak Co | Cyanine dyes containing a sulfohydrocarbon radical |
| US3274204A (en) * | 1960-08-01 | 1966-09-20 | Union Oil Co | Preparation of sulfato-betaine-type compounds |
| US3177210A (en) * | 1962-11-29 | 1965-04-06 | Polaroid Corp | Process for preparing cyanine spectral sensitizing dyes |
| US3522261A (en) * | 1965-10-23 | 1970-07-28 | Ash Stevens Inc | Esters of sulfonic acids containing quaternary ammonium groups and process for the preparation thereof |
| DE2128011A1 (de) * | 1971-06-05 | 1972-12-14 | Cassella Farbwerke Mainkur AG, 6000 Frankfurt-Fechenheim | Neue Sulfonyl verbindungen und Verfahren zu ihrer Herstellung |
-
1977
- 1977-06-10 GB GB24299/77A patent/GB1593082A/en not_active Expired
-
1978
- 1978-05-25 CH CH571478A patent/CH635088A5/de not_active IP Right Cessation
- 1978-05-30 JP JP6396278A patent/JPS545973A/ja active Granted
- 1978-06-05 US US05/912,702 patent/US4287348A/en not_active Expired - Lifetime
- 1978-06-08 DE DE2825246A patent/DE2825246C2/de not_active Expired
- 1978-06-09 FR FR787817375A patent/FR2393797A1/fr active Granted
- 1978-06-09 BE BE188478A patent/BE868003A/xx not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0222970A1 (de) * | 1985-11-21 | 1987-05-27 | Agfa-Gevaert AG | Sulfoalkylierungsverfahren |
Also Published As
| Publication number | Publication date |
|---|---|
| BE868003A (fr) | 1978-12-11 |
| GB1593082A (en) | 1981-07-15 |
| JPS545973A (en) | 1979-01-17 |
| CH635088A5 (de) | 1983-03-15 |
| JPS6225660B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-06-04 |
| DE2825246A1 (de) | 1978-12-14 |
| FR2393797A1 (fr) | 1979-01-05 |
| US4287348A (en) | 1981-09-01 |
| FR2393797B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-10-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: SCHWABE, H., DIPL.-ING. SANDMAIR, K., DIPL.-CHEM. DR.JUR. DR.RER.NAT., PAT.-ANW., 8000 MUENCHEN |
|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: ILFORD LTD., MOBBERLEY, KNUTSFORD, CHESHIRE, GB |
|
| 8339 | Ceased/non-payment of the annual fee |