CS202264B1 - Disulphoderivatives of 9,10-dihydro-9,10-et hanoanthracenes and process for preparing thereof - Google Patents
Disulphoderivatives of 9,10-dihydro-9,10-et hanoanthracenes and process for preparing thereof Download PDFInfo
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- CS202264B1 CS202264B1 CS407578A CS407578A CS202264B1 CS 202264 B1 CS202264 B1 CS 202264B1 CS 407578 A CS407578 A CS 407578A CS 407578 A CS407578 A CS 407578A CS 202264 B1 CS202264 B1 CS 202264B1
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- barium
- dihydro
- sodium
- calcium
- potassium
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- 238000004519 manufacturing process Methods 0.000 title 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
- 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 claims description 10
- 239000011734 sodium Substances 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 8
- 239000011575 calcium Substances 0.000 claims description 8
- 229910052791 calcium Inorganic materials 0.000 claims description 8
- 238000006277 sulfonation reaction Methods 0.000 claims description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 7
- 229910052788 barium Inorganic materials 0.000 claims description 7
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000011591 potassium Substances 0.000 claims description 7
- 229910052700 potassium Inorganic materials 0.000 claims description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
- VPPCQVCZKDIGGG-UHFFFAOYSA-N dibenzobicyclo[2.2.2]octadiene Chemical class C12=CC=CC=C2C2CCC1C1=CC=CC=C12 VPPCQVCZKDIGGG-UHFFFAOYSA-N 0.000 claims description 6
- 239000011777 magnesium Substances 0.000 claims description 6
- 229910052749 magnesium Inorganic materials 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- -1 NH 4 Chemical compound 0.000 claims description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 150000008064 anhydrides Chemical group 0.000 claims description 3
- 150000002823 nitrates Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 17
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 10
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical class [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 159000000009 barium salts Chemical class 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000003841 chloride salts Chemical class 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- 239000001175 calcium sulphate Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical class [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 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
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Vynález se týká disulfoderivátů 9,10-dihydro9>10-ethanoanthracenů a způsobu jejich přípravy spočívající v sulfonaci 9,I0-dihydro-9,10-ethanoanthracenů případně v přítomnosti organických rozpouštědel.The present invention relates to disulfoderivatives of 9,10-dihydro-9,10-ethanoanthracenes and a process for their preparation comprising the sulfonation of 9,10-dihydro-9,10-ethanoanthracenes optionally in the presence of organic solvents.
Disulfoderiváty 9,10-dihydro-9,10-ethanoan-thracenů nebyly dosud v dostupné literatuře popsány.Disulfoderivatives of 9,10-dihydro-9,10-ethanoanthracenes have not been described in the available literature yet.
Předmětem tohoto vynálezu jsou disulfoderiváty 9,10-dihydro-9,I0-ethanoanthracenů obec. vzorce IThe present invention provides disulfoderivatives of 9,10-dihydro-9,10-ethanoanthracenes. of formula I
kde R| a R2 značí — COOR;„ přičemž R;t je vodík, alkyl s počtem uhlíku I až 4 nebo sodík, draslík, skupina NH4, vápník, baryum, hořčík anebo R, a R2 spolu tvoří anhydridické seskupení — CO> n where R | and R 2 represents - COOR; "Wherein R 1 is hydrogen, alkyl of 1 to 4 carbon or sodium, potassium, NH 4 , calcium, barium, magnesium or R 2, and R 2 together form an anhydride moiety - CO> n
-CO? a R4 je vodík nebo sodík, draslík, skupina NH4, vápník, baryum, hořčík a připravují se tak, že se na sloučeniny obecného vzorce II-What ? and R 4 is hydrogen or sodium, potassium, NH 4 , calcium, barium, magnesium, and are prepared by the formation of compounds of formula II
kde R, a R2 má výše uvedený význam působí známými sulfonačními činidly případně v přítomnosti kyseliny octové, acetanhydridu, benzonitrilu, cyklohexanonu anebo směsí těchto látek, popřípadě se na vzniklé sulfokyseliny působí neutralizačními činidly anebo uhličitany, chloridy, dusičnany a octany sodnými, draselnými, amonnými, vápenatými, barnatými nebo hořečnatými.wherein R 1 and R 2 are as defined above with known sulfonating agents optionally in the presence of acetic acid, acetic anhydride, benzonitrile, cyclohexanone or mixtures thereof, optionally treated with neutralizing agents or with carbonates, chlorides, nitrates and sodium, potassium acetates, ammonium, calcium, barium or magnesium.
Nové sloučeniny mohou sloužit jako polotovary v chemii dehtových barviv a jako povrchově aktivní látky.The novel compounds can serve as blanks in tar chemistry and as surfactants.
Sloučeniny obecného vzorce II se získají známým způsobem z anthracenu reakcí s kyselinou maleinovou, fumarovou, maleinanhydridem anebo estery uvedených kyselin.The compounds of formula II are obtained in known manner from anthracene by reaction with maleic acid, fumaric acid, maleic anhydride and / or esters of said acids.
Vlastní sulfonace sloučenin vzorce II lze provádět tak, že se zvolený antracenový adukt smísí s kyselinou sírovou případně oleem. Rychlost disulfonace je závislá na koncentraci kyseliny sirové či olea a reakční teplotě; při použití zředěnějši kyseliny sírové je třeba vyšších teplot a delší reakční doby, zatímco koncentrovanější kyseliny sírové či oleum umožňují snížit teplotu a zkrátit dobu sulfonace.The actual sulfonation of the compounds of the formula II can be carried out by mixing the selected anthracene adduct with sulfuric acid or oleum. The rate of disulfonation is dependent on the concentration of sulfuric acid or oleum and the reaction temperature; when dilute sulfuric acid is used, higher temperatures and longer reaction times are required, while more concentrated sulfuric acid or oleum makes it possible to lower the temperature and shorten the sulfonation time.
Volba poměru mezi použitou kyselinou sírovou či oleem a zvolenou sloučeninou vzorce II je do značné míry ovlivněna její rozpustností; v každém případě je však třeba, aby na 1 mol aduktu II připadly 2 ekvivalenty sulfonačního činidla. Zpravidla je výhodné volit technicky únosný nadbytek sulfonačního činidla, v němž se adukt II během sulfonace zcela rozpustí. Při sulfonaci není rozhodující zdali se přidává organická látka do sulfonačniho činidla či obráceně.The choice of the ratio between the sulfuric acid or oleic acid used and the selected compound of formula II is largely influenced by its solubility; however, in each case, 2 equivalents of sulfonating agent must be added per mole of adduct II. As a rule, it is preferable to select a technically acceptable excess of the sulfonating agent in which the adduct II completely dissolves during sulfonation. In sulfonation, it is not critical whether the organic substance is added to the sulfonating agent or vice versa.
Jiná varianta sulfonace spočívá v tom, že se látky obecného vzorce II smísí s organickým rozpouštědlem jako např. kyselinou octovou, acetanhydridem, benzonitrilem, cyklohexanonem anebo směsí těchto látek a ke směsi se přidá zvolené sulfonační činidlo jako kyselina sírová nebo oleum, anebo se do směsi uvádí kysličník sírový či směs jeho par s inertními plyny či parami. I v tomto uspořádání sulfonace je možný obrácený postup, kdy se směs látek vzorce II s rozpouštědlem přivádí do sulfonačního činidla.Another variant of the sulfonation consists in mixing the compounds of the formula II with an organic solvent such as acetic acid, acetic anhydride, benzonitrile, cyclohexanone or a mixture thereof and adding the selected sulfonating agent such as sulfuric acid or oleum or to the mixture discloses sulfur trioxide or a mixture of its vapors with inert gases or vapors. Even in this sulfonation arrangement, a reverse process is possible in which a mixture of the compounds of formula II with a solvent is fed to the sulfonating agent.
Vznikající disulfokyseliny 9,10-dihydro-9,10-ethanoanthracenů obec. vzorce I (kde Me značí vodíkf se řadí k velmi silným kyselinám a vyznačují se značnou rozpustností ve vodě; jejich sodné, draselné, amonné, vápenaté, barnaté a horečnaté soli lze snadno připravit buď působením neutralizačních činidel na sulfokyseliny, anebo konversí kyselin chloridy, dusičnany, octany, fosforečnany, mravenčany, citrany apod. V technické praxi lze postupovat např. tak, že se zředěná reakční směs, obsahující zbytkovou kyselinu sírovou, parciálně neutralizuje přídavkem kysličníků či uhličitanů vápenatých či barnatých na pH 3 až 4 odfiltruje se síran vápenatý resp. barnatý a odpařením filtrátů se získají vápenaté či barnaté sulfonany. Při přípravě sodných, draselných či amonných solí lze přídavkem příslušných hydroxidů či uhličitanů snadno zneutralizovat obsažené suifoskupiny již při pH 3 až 4 a odpařením získat pevné sulfonany.Emerging disulfo acids of 9,10-dihydro-9,10-ethanoanthracenes village. Formula I (where Me is hydrogen) is a very strong acid and is highly water-soluble; its sodium, potassium, ammonium, calcium, barium and magnesium salts can be easily prepared either by treating the sulfo acids with neutralizing agents or by converting the acids with chlorides, nitrates , acetates, phosphates, formates, citrates, etc. In technical practice, for example, the diluted reaction mixture containing residual sulfuric acid is partially neutralized by the addition of calcium or barium carbonates or carbonates to a pH of 3 to 4 to filter out the calcium sulphate resp. In the preparation of sodium, potassium or ammonium salts, it is possible to easily neutralize the contained sulfo groups already at pH 3-4 by adding the appropriate hydroxides or carbonates, and by evaporation to obtain solid sulfonates.
Příklad IExample I
13,8 g aduktu připraveného z anthracenu a meleinanhydridu se přidá do 49,0 g 100 % kyseliny sírové (monohydrátu), za míchání se zahřeje na 80 C a na této teplotě udržuje po dobu 15 min. Reakční směs se ochladí na 20 C a zředí nalitím na 65 g ledu. Přidá se 200 ml vody, roztok zahřeje na 80 C a zneutralizuje 94,0 g uhličitanu barnatého. Odfiltruje se vyloučený síran barnatý, promyje 200 ml horké vody, filtráty se spojí s přídavkem 12,0 g kaleinované sody se zkonvertuje barnatá sůl sulfokyselin na sodnou; vyloučený uhličitan barnatý se odfiltruje, promyje 20 ml vody a spojené filtráty odpaří na vodní bázi do sucha. Získá se 29,0 g disulfonanů sodných13.8 g of an adduct prepared from anthracene and melein anhydride are added to 49.0 g of 100% sulfuric acid (monohydrate), heated to 80 ° C with stirring and held at this temperature for 15 min. The reaction mixture was cooled to 20 ° C and diluted by pouring onto 65 g of ice. 200 ml of water are added, the solution is heated to 80 DEG C. and neutralized with 94.0 g of barium carbonate. The precipitated barium sulphate is filtered off, washed with 200 ml of hot water, the filtrates combined with the addition of 12.0 g of kaleinized soda and the barium salt of the sulfo acids is converted to sodium; the precipitated barium carbonate is filtered off, washed with 20 ml of water and the combined filtrates are evaporated to dryness on a water basis. 29.0 g of sodium disulfonates are obtained
V případě, že se po odfiltrování síranu barnatého odpaří filtrát k suchu, získá se barnatá sůl disulfoderivátu.If the filtrate is evaporated to dryness after filtering the barium sulfate, the barium salt of the disulfoderivative is obtained.
Přiklad 2Example 2
27,6 g aduktu připraveného z maleinanhydridu a anthracenu se rozpustí ve 300 ml ac^tanhydridu při 70 °C a při této teplotě se přidá po kapkách27.6 g of an adduct prepared from maleic anhydride and anthracene are dissolved in 300 ml of acetic anhydride at 70 ° C and added dropwise at this temperature
19,6 g monohydrátu a při 80 až 90 °C se udržuje po dobu 15 min. Reakční směs se ochladí na 20 °C a podrobí analýze.19.6 g of monohydrate and held at 80-90 ° C for 15 min. The reaction mixture was cooled to 20 ° C and subjected to analysis.
Chromatografickou analýzou byla ve vzorku prokázána disulfokyselinaChromatographic analysis showed a disulfoacid in the sample
Příklad 3Example 3
17,5 g aduktu připraveného z antracenu a diethylesteru kyseliny fumarové se přidá do 49,0 g 100% kyseliny sírové, načež se dále postupuje jako u př. I.17.5 g of an adduct prepared from anthracene and diethyl fumarate are added to 49.0 g of 100% sulfuric acid, followed by the procedure of Example I.
Získá se 26,7 g dvojsodné soli vzorce26.7 g of the disodium salt of the formula are obtained
C00CtH,C00C t H,
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS407578A CS202264B1 (en) | 1978-06-21 | 1978-06-21 | Disulphoderivatives of 9,10-dihydro-9,10-et hanoanthracenes and process for preparing thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS407578A CS202264B1 (en) | 1978-06-21 | 1978-06-21 | Disulphoderivatives of 9,10-dihydro-9,10-et hanoanthracenes and process for preparing thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS202264B1 true CS202264B1 (en) | 1980-12-31 |
Family
ID=5382687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS407578A CS202264B1 (en) | 1978-06-21 | 1978-06-21 | Disulphoderivatives of 9,10-dihydro-9,10-et hanoanthracenes and process for preparing thereof |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS202264B1 (en) |
-
1978
- 1978-06-21 CS CS407578A patent/CS202264B1/en unknown
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