GB2025954A - Anthraquinone Sulphonamides - Google Patents
Anthraquinone Sulphonamides Download PDFInfo
- Publication number
- GB2025954A GB2025954A GB7922526A GB7922526A GB2025954A GB 2025954 A GB2025954 A GB 2025954A GB 7922526 A GB7922526 A GB 7922526A GB 7922526 A GB7922526 A GB 7922526A GB 2025954 A GB2025954 A GB 2025954A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- disulphonamide
- formula
- hydrogen
- bissulpho
- 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.)
- Withdrawn
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- XTSPUZLHSITOOU-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonamide Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)N XTSPUZLHSITOOU-UHFFFAOYSA-N 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 150000001768 cations Chemical group 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 239000000243 solution Substances 0.000 claims description 24
- -1 amine salt Chemical group 0.000 claims description 20
- 239000011734 sodium Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- 239000011591 potassium Chemical group 0.000 claims description 6
- 239000012670 alkaline solution Substances 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 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
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 2
- VEYSRMNMONRAAF-UHFFFAOYSA-N [[9,10-dioxo-6-(sulfomethylsulfamoyl)anthracen-2-yl]sulfonylamino]methanesulfonic acid Chemical compound OS(=O)(=O)CNS(=O)(=O)C1=CC=C2C(=O)C3=CC(S(=O)(=O)NCS(=O)(=O)O)=CC=C3C(=O)C2=C1 VEYSRMNMONRAAF-UHFFFAOYSA-N 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000002738 chelating agent Substances 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 239000003352 sequestering agent Substances 0.000 claims description 2
- 239000004289 sodium hydrogen sulphite Substances 0.000 claims description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- ADSDHMANTIJUDA-UHFFFAOYSA-N [2-ethyl-9,10-dioxo-6-(sulfosulfamoyl)-1h-anthracen-2-yl]sulfonylsulfamic acid Chemical compound O=C1C2=CC(S(=O)(=O)NS(O)(=O)=O)=CC=C2C(=O)C2=C1C=CC(CC)(S(=O)(=O)NS(O)(=O)=O)C2 ADSDHMANTIJUDA-UHFFFAOYSA-N 0.000 claims 1
- GCEBMWJNCKXRPT-UHFFFAOYSA-N [2-ethyl-9,10-dioxo-7-(sulfosulfamoyl)-1h-anthracen-2-yl]sulfonylsulfamic acid Chemical compound O=C1C2=CC=C(S(=O)(=O)NS(O)(=O)=O)C=C2C(=O)C2=C1C=CC(CC)(S(=O)(=O)NS(O)(=O)=O)C2 GCEBMWJNCKXRPT-UHFFFAOYSA-N 0.000 claims 1
- LDVKESHMXMSJKG-UHFFFAOYSA-N [[9,10-dioxo-7-(sulfomethylsulfamoyl)anthracen-2-yl]sulfonylamino]methanesulfonic acid Chemical compound C1=C(S(=O)(=O)NCS(O)(=O)=O)C=C2C(=O)C3=CC(S(=O)(=O)NCS(=O)(=O)O)=CC=C3C(=O)C2=C1 LDVKESHMXMSJKG-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000003595 mist Substances 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- XUIVKWAWICCWIQ-UHFFFAOYSA-M sodium;formaldehyde;hydrogen sulfite Chemical compound [Na+].O=C.OS([O-])=O XUIVKWAWICCWIQ-UHFFFAOYSA-M 0.000 description 4
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000005864 Sulphur Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- CZNYYPMFWGMKRC-UHFFFAOYSA-N 9,10-dioxoanthracene-2,6-disulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C2C(=O)C3=CC(S(=O)(=O)Cl)=CC=C3C(=O)C2=C1 CZNYYPMFWGMKRC-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- GEAXKAYFQVGDRP-UHFFFAOYSA-N [4-butyl-7-[ethyl(sulfo)sulfamoyl]-9,10-dioxoanthracen-2-yl]sulfonyl-ethylsulfamic acid Chemical compound O=C1C2=CC(S(=O)(=O)N(CC)S(O)(=O)=O)=CC=C2C(=O)C2=C1C=C(S(=O)(=O)N(CC)S(O)(=O)=O)C=C2CCCC GEAXKAYFQVGDRP-UHFFFAOYSA-N 0.000 description 2
- OBESRABRARNZJB-UHFFFAOYSA-N aminomethanesulfonic acid Chemical compound NCS(O)(=O)=O OBESRABRARNZJB-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229960003080 taurine Drugs 0.000 description 2
- 150000003682 vanadium compounds Chemical class 0.000 description 2
- NFDDWQLSNMGJSE-UHFFFAOYSA-N (4-butyl-9,10-dioxoanthracen-2-yl)sulfonyl-methylsulfamic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S(=O)(=O)N(C)S(O)(=O)=O)C=C2CCCC NFDDWQLSNMGJSE-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- APLNAFMUEHKRLM-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(3,4,6,7-tetrahydroimidazo[4,5-c]pyridin-5-yl)ethanone Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)N=CN2 APLNAFMUEHKRLM-UHFFFAOYSA-N 0.000 description 1
- PTKWYSNDTXDBIZ-UHFFFAOYSA-N 9,10-dioxoanthracene-1,2-disulfonic acid Chemical class C1=CC=C2C(=O)C3=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C3C(=O)C2=C1 PTKWYSNDTXDBIZ-UHFFFAOYSA-N 0.000 description 1
- JHQAPKCPBJFFGX-UHFFFAOYSA-N 9,10-dioxoanthracene-1,5-disulfonamide Chemical compound O=C1C=2C(S(=O)(=O)N)=CC=CC=2C(=O)C2=C1C=CC=C2S(N)(=O)=O JHQAPKCPBJFFGX-UHFFFAOYSA-N 0.000 description 1
- YCQGWFGTBJAOFM-UHFFFAOYSA-N 9,10-dioxoanthracene-2,7-disulfonamide Chemical compound C1=C(S(N)(=O)=O)C=C2C(=O)C3=CC(S(=O)(=O)N)=CC=C3C(=O)C2=C1 YCQGWFGTBJAOFM-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 229910018828 PO3H2 Inorganic materials 0.000 description 1
- RNVBBVBLEIXMHY-UHFFFAOYSA-N [2-ethyl-9,10-dioxo-5-(sulfosulfamoyl)anthracen-1-yl]sulfonylsulfamic acid Chemical compound O=C1C2=C(S(=O)(=O)NS(O)(=O)=O)C(CC)=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)NS(O)(=O)=O RNVBBVBLEIXMHY-UHFFFAOYSA-N 0.000 description 1
- ZHFDMYBATUMYOC-UHFFFAOYSA-N [2-ethyl-9,10-dioxo-7-(sulfosulfamoyl)anthracen-1-yl]sulfonylsulfamic acid Chemical compound C1=C(S(=O)(=O)NS(O)(=O)=O)C=C2C(=O)C3=C(S(=O)(=O)NS(O)(=O)=O)C(CC)=CC=C3C(=O)C2=C1 ZHFDMYBATUMYOC-UHFFFAOYSA-N 0.000 description 1
- PHWWEJBQHZREMG-UHFFFAOYSA-N [[9,10-dioxo-5-(sulfomethylsulfamoyl)anthracen-2-yl]sulfonylamino]methanesulfonic acid Chemical compound O=C1C2=CC(S(=O)(=O)NCS(=O)(=O)O)=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)NCS(O)(=O)=O PHWWEJBQHZREMG-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- RJKUAIDVEMLKFT-UHFFFAOYSA-N anthracene-9,10-dione;sulfuryl dichloride Chemical class ClS(Cl)(=O)=O.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RJKUAIDVEMLKFT-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- DULSNUJHZMVVDL-UHFFFAOYSA-N azane;formaldehyde;sulfurous acid Chemical compound [NH4+].O=C.OS([O-])=O DULSNUJHZMVVDL-UHFFFAOYSA-N 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- ALVGPPOPGPCDCG-UHFFFAOYSA-M potassium;formaldehyde;hydrogen sulfite Chemical compound [K+].O=C.OS([O-])=O ALVGPPOPGPCDCG-UHFFFAOYSA-M 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- UPDATVKGFTVGQJ-UHFFFAOYSA-N sodium;azane Chemical compound N.[Na+] UPDATVKGFTVGQJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- IHIXIJGXTJIKRB-UHFFFAOYSA-N trisodium vanadate Chemical compound [Na+].[Na+].[Na+].[O-][V]([O-])([O-])=O IHIXIJGXTJIKRB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1493—Selection of liquid materials for use as absorbents
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Compounds having the general formula: <IMAGE> where A is a C1-C4 straight or branched chain alkylene radical, B is a -SC3M, -CO2M, -PO3HM or -PO3M2 grouping, M is hydrogen, or a cation giving a water-soluble derivative, R is hydrogen, a cation giving a water-soluble derivative, or a C1-C4 straight or branched alkyl, R, is hydrogen, methyl or -COOH, and m is 0 or 1 and processes of preparing them.
Description
SPECIFICATION
Chemical Compounds
The present invention relates to novel anthraquinone sulphonamides and to processes of preparing them.
According to the present invention there is provided a compound having the general formula:
where A is a C1-C4 straight or branched chain alkylene radical, B is a -SO3M, -C02M, -P03HM or ~PO3M2 grouping,
M is hydrogen, or a cation giving a water-soluble derivative,
R is hydrogen, a cation giving a water-soluble derivative or
a C1-C4 straight or branched chain alkyl,
R1 is hydrogen, methyl or -COOH. and m is 0 or 1.
Where M or R is a cation giving a water-soluble derivative this is preferably an alkali metal for example sodium or potassium or an unsubstituted or substituted ammonium cation, for example, ammonium or optionally substituted C,--C, alkylammonium, examples of alkyl substituents being methyl, ethyl, propyl, butyl or mono-, di- or tri-hydroxyethyl.
Preferably B is a -SO3M grouping, Rr is hydrogen and M and R are hydrogen, sodium, potassium or ammonium.
More preferably R1 is hydrogen, M and R are hydrogen, sodium, potassium or ammonium and A is a C1-C4 straight chain alkylene radical.
Especially preferred compounds of those where R, is hydrogen, M and R are hydrogen, sodium, potassium or ammonium and A is methylene or ethylene and m is 1.
Non-limiting Examples of the compounds covered by the general formula I are as follows:
Where m=O and R=Rt=H N-Sulphomethylanthraquinone#2-sulphonamide N-Sulpho-2-ethylanthraquinone-2-sulphonamide N-Sulpho-3-propylanthraquinone-2-sulphonamide
N-Sulpho-4-butylanthraquinone-2-sulphonamide N-Sulpho( 1 , 1 -dimethylethyl)anthraquinone-2-sulphonamide
Where m=0, R=C1~C4 alkyl and R=H N-Methyl-sulpho-methylanthraquinone-2-sulphonamide
N-methyl-N-sulpho-2-ethylanthraquinone-2-sulphonamide
N-methyl-N-sulpho-3-propylanthraquinone-2-sulphonamide
N-Methyl-N-sulpho-4-butylanthraquinone-2-sulphonamide
Where m=1, R=R1=H N,N'-Bissu lphomethylanthraquinone-1 ,5-disulphonamide
N,N'-Bissulphomethylanthraquinone-1 ,6-disulphonamide N,N'-Bissulphomethylanthraquinone#1 ,7-disulphonamide N,N'-Bissulphomethylanthraquinone-2,6-disulphonamide N,N'-Bissulphomethylanthraquinone-.2,7-disulphonamide N,N'-Bissulpho-2-ethylanthraquinone-1 ,5-disulphonamide N,N'-Bissulpho.-2-ethylanthraquinone- 1 ,6-disulphonamide
N,N'-Bissulpho-2-ethylanthraquinone-1 ,7-disulphonamide N,N'-Bissulpho#-ethylanthraquinone-2,6-disulphonamide N,N'-Bissulpho-2-ethylanthraquinone-2,7-disulphonamide N,N'-Bissulpho-3-propylanthraquinone- 1 ,5-disulphonamide N,N'-Bissulpho-3-propylanthraquinone- 1 ,6-disulphonamide
N,N'-Bissulpho-3-propylanthraquinone-1 7-disulphonamide N,N'-Bissulpho-3-propylanthraquinone-2,6-disulphonamide N,N'-Bissulpho-3-propylanthraquinone-2,7-disulphonamide N,N'-Bissulpho-4-butylanthraquinone-1 ,5-disulphonamide N,N'-Bissulpho-4-butylanthraquinone-1 ,6-disulphonamide
N,N'-Bissulpho-4-butylanthraquinone-1 ,7-disulphonamide
N,N'-Bissulpho-4-butylanthraquinone-2,6-disulphonamide
N,N'-Bissulpho-4-butylanthraquinone-2,7-disulphonamide N,N'-Bissulpho( 1,1 -dimethylethyl)anthraquinone-2,6-disulphonamide N,N'-Bissulpho( 1 , 1 -dimethylethyl)anthraquinone-2,7-disulphonamide where m=1, Fl=C1-C4 alkyl, R1=H N,N'-Dimethyl-N,N'-bissulphomethylanthraquinone-1 ,5-disulphonamide N,N'-Diethyl-N,N'-bissulphomethylanthraquinone-1 ,6-disulphonamide
N,N'-Dipropyl-N,N'-bissulphomethylanthraquinone-1 ,7-disulphonamide
N,N'-Dimethyl-N,N'-bissulphomethylanthraquinone-2,6-disulphonamide N,N'-Diethyl-N,N'-bissulphomethylanthraquinone-2,7-disulphonamide N,N'-Dimethyl-N,N'-bissulpho-2-ethylanthraquinone- 1,5-disulphonamide
N,N'-Diethyl-N,N'-bissulpho-2-ethylanthraquinone-1 ,6-disulphonamide
N.N'-Dimethyl-N,N'-bissulpho-2-ethylanthraquinone-2,6-disulphonamide N,N'-Diethyl-N,N'-bissulpho-2-ethylanthraquinone-2,7-disulphonamide N,N'-Diethyl-N,N'-bissulpho-3-propylanthraquinone-1 ,6-disulphonamide
N,N'-Dipropyl-N,N'-bissulpho-3-propylanthraquinone-1,7-disulphonamide
N,N'-Dimethyl-N,N'-bissulpho-3-propylanthraquinone-2,6-disulphonamide
N,N'-Diethyl-N,N'-bissulpho-3-propylanthraquinone-2,7-disulphonamide
N,N'-Diethyl-N,N'-bissulpho-4-butylanthraquinone-1,6-disulphonamide
N,N'-Dipropyl-N,N'-bissulpho-4-butylanthraquinone-1,7-disulphonamide N,N'-Dimethyl-N,N'-bissulpho-4-butylanthraquinone-2,6-disulphonamide N,N'-Diethyl-N,N'-bissulpho-4-butylanthraquinone-2,7-disulphonamide or a compound corresponding to any of the above compounds, but where Bis--CO2H N,N'-Diethyl-N,N'-bissulpho-4-butylanthraquinone-2,7-disulphonamide or-PO3H2 instead of --SO,H or any mixture thereof.
Especially preferred compounds are:
N,N'-Bissulphomethylanthraquinone-2,6-disulphonamide
N,N'-Bissulphomethylanthraquinone-2,7-disulphonamide or a mixture of these compounds in any proportion
N,N'-Bissulpho-2-ethylanthraquinone-2,6-disulphonamide
N,N'-Bissulpho-2-ethylanthraquinone-2,7-disulphonamide or a mixture of these compounds in any proportion.
Further Examples of compounds of general formula I include the alkali metal or amine salts of any of the above compounds particularly the sodium, potassium or ammonium salts.
The compounds of formula I where R is H or C1-C4 straight or branched chain alkyl may be prepared by reacting the corresponding anthraquinone sulphonyl halide having the general formula
with a compound having the general formula
where X is halogen, especially chlorine, R2 is H or C1~C4 straight or branched chain alkyl and A, m, B and R1 have their previous significance.
The reaction may conveniently be carried out by adding the compound of formula Ill to a solution of the compound of formula II in a solvent system consisting of aqueous alkali and a water-soluble ether at less than 200C. The reaction time may vary depending on the circumstances but is conveniently from 1 to 12 hours. An example of a water-soluble ether is tetrahydrofuran.
The compound of formula 11 may be prepared by the method described by Kozlev et al., J. Gen.
Chem. Russ 1947, 17, 289.
The compounds of formula I where A is -CH2- may also be prepared by reacting the corresponding anthraquinone sulphonamide having the general formula
with a compound having the general formula
HOCH2B V where m, B, R and R1 have their previous significance.
The reaction may conveniently be carried out by adding a compound of formula IV to a solution of a compound of formula V in water and heating at a temperature up to 10000. The reaction time may vary depending upon the circumstances but is conveniently from 1 to 12 hours. The temperature of the reaction is preferably from 6000 to 800C.
The compound of formula V where B is --SO,Na may conveniently be prepared from formaldehyde and sodium bisulphite in aqueous solution at 800 C. In this case the compound of formula I is normally prepared by adding the compound of formula IV to such a solution.
The compounds of formula IV may be prepared by the method described by Tr. Leningr. Khim
Farmatseut. Inst., 1960, 11,48.
The compounds having the general formula I may be used as intermediates for dyestuff chemicals, agrochemicals or pharmaceuticals.
Also, the removal of hydrogen sulphide as sulphur from gases by the methods described in British
Patent Specification 871,233 and 948,270 may be carried out but using the compounds of formula I in aqueous alkaline solution instead of the anthraquinone disulphonic acids there used, as described in our copending Application No. MA 1738 Div.
This invention also provides an aqueous alkaline solution of a compound of formula I which solution may contain a compound of a metal having at least two valency states for example a vanadium compound and if necessary a chelating or sequestering agent for retaining such metal compounds in solution. Such solutions are suitable for the absorption of hydrogen sulphide and converting it to sulphur. The vanadium compound may be an ortho-, meta-, or pyrovanadate of ammonia or of an alkali metal for example sodium ammonium vanadate or sodium orthovanadate.
Since the presence of chloride ions may lead to corrosion in the treatment plants for the removal of hydrogen sulphide as sulphur the method of preparing the compound of formula I by the reaction of compounds IV and V is advantageous in that it gives a product substantially free from chloride ions.
The following Examples further illustrate the present invention in which the anthraquinone sulphonyl chlorides and sulphonamides are prepared by the literature methods indicated above.
Example 1
76.9 Parts sodium formaldehyde bisulphite and 22.9 parts sodium hydroxide in 300 parts of water are charged into a 3-neck flask equipped with a stirrer, thermometer, condenser and the solution heated to 700. 105 parts of a 1:1 mixture of anthraquinone-2,6/2,7-disulphonamides are added portionwise and the resulting mixture heated at 700 during 3 hours. Evaporation of the resulting solution gives 171.4 parts of the dark brown tetrasodium N,N'-disulphonomethylanthraquinone2,6/2,7-disulphonamides having a melting point of > 3000 and the following analysis: 0,25.9; H, 2.2; N, 4.1; 5, 17.7; Na, 13.2; Cl-,0.1 S0,2-, 16.9% and a water content of 5.4%.
Example 2
4.4. Parts aminomethanesulphonic acid and 1.6 parts sodium hydroxide in 50 parts water and
150 parts tetrahydrofuran are charged into a 4-neck flask equipped with a stirrer, thermometer, condenser and pH electrode. 8 Parts anthraquinone-2,6-disulphonylchloride are added portionwise, the pH being maintained at 11.5 by the addition of 8N sodium hydroxide solution and the temperature at < 20 with ice cooling. Evaporation of the resulting solution gives 14.2 parts mustard coloured disodium N,N'-disulphonomethylanthraquinone-2,6-disulphonamide having melting point > 3000 and the following analysis: C, 24.1;H, 2.0; N, S,15.7; Na,15.8; Cl-,8.0 and S042#, 12.7%.
Example 3
10 Parts taurine and 3.2 parts sodium hydroxide in 100 parts water and 160 parts tetrahydrofuran are charged into a 4-neck flask as in Example 2. 1 6 Parts anthraquinone-2,6disulphonylchloride are added portionwise, the pH maintained at 12.5 with 8N sodium hydroxide solution and the temperature at < 200 with ice cooling. Evaporation of the resulting solution gives 34.5 parts of the brown disodiu m disodium N,N'-disulphonoethylanthraquinone-2,6-disulphonamide having a melting point > 3000 and the following analysis:
C, 30.9; H, 2.6; N, 3.1; S, 16.7; Na, 7.4; Cl-,5.9 and So42-, 7.2%.
Example 4
4 4. Parts aminomethanesulphonic acid and 1.6 parts sodium hydroxide in 250 parts water are
charged into a 4 neck flask as in Example 2. 8 Parts of a 1:1 mixture of anthraquinone-2,6/2,7disulphonylchloride are added portionwise. The pH is maintained at 11.8 with 8N sodium hydroxide solution during 1 5 hours or until a complete solution is obtained. Evaporation of this solution gives the brown tetrasodium N,N'-disulphonomethylanthraquinone-2,6/2,7-disulphonamides having a melting point > 3000 and the following analysis C,21.8; H, 1.7; N, 2.4; S,13.9; Na,19.8; CI-, 10.2 and S042#,21 21.2%.
Example 5
6.2 Parts taurine and 2 parts sodium hydroxide in 50 parts water and 34 parts tetrahydrofuran are charged into a 4-neck flask in Example 2. 10 Parts of a 1:1 mixture of anthraquinone-2,6/2,7disulphonylchlorides are added portionwise, the pH maintained at 13.1 with 8N sodium hydroxide solution and the temperature at < 200 with ice cooling. Evaporation of the resulting solution gives 21.3 parts of the brown-black tetrasodium N,N'-disulphonoethylanthraquinone-2,6/2,7-disulphonamides having a melting point > 3000 and the following analysis:
C, 23.3; H, 2.6; N, 3.1; S, 14.4; Na, 14.7; CI-, 7.9 and S042-, 4.5%.
Example 6
6 Parts glycine and 3.2 parts sodium hydroxide in 100 parts water and 100 parts tetrahydrofuran are charged into a four-neck flask equipped with a stirrer, thermometer, condenser and pH electrode.
16 Parts of a 1:1 mixture of anthraquinone-2,6/2,7-disulphonylchlorides are added portionwise, the pH being maintained at 12.3 by the addition of 8N sodium hydroxide solution and the temperature at < 200 with ice cooling. Evaporation of the resulting solution gives 28.7 parts of the black tetra-sodium N,N'-dicarboxymethylanthraquinone-2,6/2,7-disulphonamides having a melting point of 2500 dec.
Example 7
4 Parts sodium formaldehyde bisulphite and 1.2 parts sodium hydroxide in 20 parts water are treated with 5.6 parts anthraquinone-2,7-disulphonamide as described in Example 1. Evaporation of the resulting solution gives 6.5 parts of the dark brown sodium salts of N,N'disulphonomethylanthraquinone-2,7-disulphonamide having a melting point > 2500 and the following analysis:
C, 16.3; H, 2.3; N, 3.6; S,19.5; Na, 14.4; CI- < 0.1 and S042#, 14.0%.
Example 8
3.7 Parts sodium formaldehyde bisulphite and 1.1 parts sodium hydroxide in 20 parts water are treated with 5 parts anthraquinone-1 ,5-disulphonamide as described in Example 1. Evaporation of the resulting solution gives 6.5 parts of the black sodium salts of N,N'-disulphonomethylanthraquinone1 5-disulphonamide having a melting point > 3000 and the following analysis:
C, 20.2; H, 2.1 ; N, 3.7; S, 18.2; Na, 15.5; CI-, 0.9; S042-, 16.9% and a water content of 8.2%.
Example 9
6.1 Parts sodium formaldehyde bisulphite and 1.8 parts sodium hydroxide in 40 parts water are treated with 8.4 parts of a mixture of anthraquinone-1 ,6/1 ,7-disulphonamides as described in Example 1. Evaporation of the resulting solution gives 1 5.1 parts of the black sodium salts of N,N'disulphonomethylanthraquinone-1 ,6/1 ,7-disulphonamides having a melting point > 3000 and the following analysis:
C, 26.1; H, 2.1; N, 3.6; S, 1 7.99; Na, 13.3; Cl-, 0.4; S042-, 15.9% and a water content of 6.7%.
The use of potassium formaldehyde bisulphite in Examples 1 and 7 ta 9 and potassium hydroxide in Examples 2-6 would provide the corresponding tetrapotassium salts. Similarly, ammonium formaldehyde bisulphite and ammonium hydroxide would provide the tetra-ammonium salts.
We are aware of British Patent No. 465343 but we make no claim to any of the acid amides of the anthraquinone series per se disclosed therein.
Claims (23)
1. A compound having the general formula:
wherein A is a C1-C4 straight or branched chain alkylene radical,
B is a -S03M, -C02M, -P03HM or -P03M2 grouping,
M is hydrogen or a cation giving a water-soluble derivative,
R is hydrogen, a cation giving a water-soluble derivative or a C1-C4 straight or branched chain alkyl
R, is hydrogen, methyl or-CO0H, and m is O or 1.
2. A compound as claimed in claim 1 in which B is a --SO,M grouping, R, is hydrogen and M and
Rare hydrogen, an alkali metal or an unsubstituted or substituted ammonium cation.
3. A compound as claimed in Claim 1 or Claim 2 in which A is a C1-C4 straight chain alkylene radical.
4. A compound as claimed in any of the preceding claims in which A is methylene or ethylene and mist.
5. A compound as claimed in any of the preceding claims in which M and/or R is an alkali metal or amine salt.
6. A compound as claimed in any of the preceding claims in which M and/or R is sodium, potassium or ammonium.
7. N,N'-Bissulphomethylanthraquinone-2,6-disulphonamide.
8. N,N'-Bissulphomethylanthraquinone-2,7-disulphonamide.
9. A mixture of the compounds claimed in claim 7 and claim 8 in any proportion.
10. N,N'-Bissulpho-2-ethylanthraquinone-2,6-disulphonamide.
11. N,N'-Bissulpho-2-ethylanthraquinone-2,7-disulphonamide.
12. A mixture of the compounds claimed in claim 10 and claim 11 in any proportion.
13. A compound as claimed in Claim 1 substantially as described in any of Examples 1 to 9.
14. A process of preparing a compound of formula I defined in claim 1 which comprises reacting an anthraquinone sulphonyl halide having the general formula:
with a compound having the general formula:
where X is halogen, R2 is H or C1-C4 straight or branched chain alkyl, and A, m, B, and R1 are as defined in Claim 1.
15. A process as claimed in claim 14 in which X is chlorine.
1 6. A process of preparing a compound of formula I defined in Claim 1 where A is --CH,,- which comprises reacting an anthraquinone sulphonamide having the general formula
with a compound having the general formula
HOCH2B V wherein m, B, R and R1 are as defined in Claim 1.
17. A process as claimed in Claim 1 6 in which and the compound of formula V is prepared from formaldehyde and sodium bisulphite in aqueous solution at 700 C, the compound of formula IV being added to this solution.
18.A process as claimed in claim 14 substantially as described in any of Examples 2 to 6.
19. A process as claimed in Claim 1 6, substantially as described in any of Examples 1 and 7 to 9.
20. A compound of formula I whenever prepared by a process as claimed in any of Claims 14 to 19.
21. An aqueous alkaline solution of a compound claimed in any of Claims 1 to 13 and 20.
22. An aqueous alkaline solution as claimed in claim 21 containing a compound of a metal having at least two valency states and, if necessary, a chelating or sequestering agent for retaining such metal compounds in solution.
23. An aqueous alkaline solution as claimed in claim 22 in which the compound of a metal having at least two valency states is ortho-, meta-, or pyrovanadate of ammonia or an alkali metal.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7922526A GB2025954A (en) | 1978-07-21 | 1979-06-28 | Anthraquinone Sulphonamides |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7830844 | 1978-07-21 | ||
| GB7922526A GB2025954A (en) | 1978-07-21 | 1979-06-28 | Anthraquinone Sulphonamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB2025954A true GB2025954A (en) | 1980-01-30 |
Family
ID=26268312
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7922526A Withdrawn GB2025954A (en) | 1978-07-21 | 1979-06-28 | Anthraquinone Sulphonamides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2025954A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997000675A1 (en) * | 1995-06-23 | 1997-01-09 | Boonville Limited | Mono- and disulfo-substituted anthraquinones and their use for the treatment of bone matrix disorders |
| WO2002064680A1 (en) * | 2001-02-10 | 2002-08-22 | Clariant Gmbh | Acid pigment dispersants and pigment preparations |
| EA030302B1 (en) * | 2008-11-21 | 2018-07-31 | Форест Лэборетериз Холдингз Лимитед | Anthraquinone dioximes and use thereof |
-
1979
- 1979-06-28 GB GB7922526A patent/GB2025954A/en not_active Withdrawn
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997000675A1 (en) * | 1995-06-23 | 1997-01-09 | Boonville Limited | Mono- and disulfo-substituted anthraquinones and their use for the treatment of bone matrix disorders |
| US5856358A (en) * | 1995-06-23 | 1999-01-05 | Boonville Limited | Mono- and disulfo-substituted anthraquinones and their use for the treatment of bone matrix disorders |
| RU2202534C2 (en) * | 1995-06-23 | 2003-04-20 | Эйч-Ген Би.В. | Mono- and disulfosabstituted anthraquinones and their application for treatment of osseous matrix lesion |
| WO2002064680A1 (en) * | 2001-02-10 | 2002-08-22 | Clariant Gmbh | Acid pigment dispersants and pigment preparations |
| US6918958B2 (en) | 2001-02-10 | 2005-07-19 | Clariant Gmbh | Acid pigment dispersants and pigment preparations |
| EA030302B1 (en) * | 2008-11-21 | 2018-07-31 | Форест Лэборетериз Холдингз Лимитед | Anthraquinone dioximes and use thereof |
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