CS241843B1 - Způsob výroby 2,5-dihydroxybenzenswltoaanu vápenatého - Google Patents
Způsob výroby 2,5-dihydroxybenzenswltoaanu vápenatého Download PDFInfo
- Publication number
- CS241843B1 CS241843B1 CS848343A CS834384A CS241843B1 CS 241843 B1 CS241843 B1 CS 241843B1 CS 848343 A CS848343 A CS 848343A CS 834384 A CS834384 A CS 834384A CS 241843 B1 CS241843 B1 CS 241843B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- calcium
- benzoquinone
- reaction
- dihydroxybenzenesulphonate
- hydroxysulfonate
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- QGNBTYAQAPLTMX-UHFFFAOYSA-L calcium dobesilate Chemical compound [Ca+2].OC1=CC=C(O)C(S([O-])(=O)=O)=C1.OC1=CC=C(O)C(S([O-])(=O)=O)=C1 QGNBTYAQAPLTMX-UHFFFAOYSA-L 0.000 title abstract description 9
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims abstract description 38
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 229940005561 1,4-benzoquinone Drugs 0.000 claims abstract description 19
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000011575 calcium Substances 0.000 claims abstract description 19
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 19
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 4
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 4
- -1 bisulfite aldehydes Chemical class 0.000 claims abstract description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 19
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 6
- LVGQIQHJMRUCRM-UHFFFAOYSA-L calcium bisulfite Chemical compound [Ca+2].OS([O-])=O.OS([O-])=O LVGQIQHJMRUCRM-UHFFFAOYSA-L 0.000 claims description 6
- 235000010260 calcium hydrogen sulphite Nutrition 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 238000007259 addition reaction Methods 0.000 claims description 2
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 239000003595 mist Substances 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 abstract description 7
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 239000010410 layer Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 5
- 239000000292 calcium oxide Substances 0.000 description 5
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- IKQCSJBQLWJEPU-UHFFFAOYSA-N 2,5-dihydroxybenzenesulfonic acid Chemical compound OC1=CC=C(O)C(S(O)(=O)=O)=C1 IKQCSJBQLWJEPU-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- WHQOKFZWSDOTQP-UHFFFAOYSA-N 2,3-dihydroxypropyl 4-aminobenzoate Chemical compound NC1=CC=C(C(=O)OCC(O)CO)C=C1 WHQOKFZWSDOTQP-UHFFFAOYSA-N 0.000 description 2
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- GBAOBIBJACZTNA-UHFFFAOYSA-L calcium sulfite Chemical compound [Ca+2].[O-]S([O-])=O GBAOBIBJACZTNA-UHFFFAOYSA-L 0.000 description 2
- 235000010261 calcium sulphite Nutrition 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 229960004337 hydroquinone Drugs 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- NJRDOBDVQJCHPD-UHFFFAOYSA-L calcium;2-hydroxypropane-2-sulfonate Chemical compound [Ca+2].CC(C)(O)S([O-])(=O)=O.CC(C)(O)S([O-])(=O)=O NJRDOBDVQJCHPD-UHFFFAOYSA-L 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000383 hazardous chemical Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- VKDSBABHIXQFKH-UHFFFAOYSA-M potassium;4-hydroxy-3-sulfophenolate Chemical compound [K+].OC1=CC=C(O)C(S([O-])(=O)=O)=C1 VKDSBABHIXQFKH-UHFFFAOYSA-M 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- KICVIQZBYBXLQD-UHFFFAOYSA-M sodium;2,5-dihydroxybenzenesulfonate Chemical compound [Na+].OC1=CC=C(O)C(S([O-])(=O)=O)=C1 KICVIQZBYBXLQD-UHFFFAOYSA-M 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- DGQOCLATAPFASR-UHFFFAOYSA-N tetrahydroxy-1,4-benzoquinone Chemical compound OC1=C(O)C(=O)C(O)=C(O)C1=O DGQOCLATAPFASR-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
2,5-Dihydroxybenzensulifonan vápenatý se
připravuje reakcí adičních sloučenin ketonů
nebo aldehydů s hydrogensiřičitanem
vápenatým a 1,4-benzochinonu. Reakce se
provádí v homogenní nebo heterogenní fá
zi, přičemž 1,4-benzochinon je s výhodou
rozpuštěn v chlorovaných alifatických uhlovodících
nebo v alkylesterech ailkamových
kyselin. 2,5-Dihydroxybenzensul'fonan vápenatý
se používá jako venofarmakum
Claims (4)
1. Způsob výroby 2,5-dihydrobenzensulfonanu vápenatého z 1,4-benzochinonu, vyznačující se tím, že na 1,4-benzochinon se pří pH 1,5 a.ž 9 v rozmezí teplot —15 až -j- 100 °C působí za přítomnosti vody 1-hydroxysulfonanem vápenatým, přičemž výchozí karbonylová sloučenina pro uvedený 1-bydroxysulfonan vápenatý má teplotu varu do 220 °C a je schopna adičně reagovat s hydrogensiřičitanem vápenatým ina karbonylové skupině, a 2,5-dihydroxyibenzensulTonan vápenatý se z reakční směsi izoluje.
2. Způsob podle bodu 1, vyznačující se tím, že se reakce provádí v heterogení fázi v prostředí chlorovaných alifatických uhlovodíků o počtu atomů mlhlíku Ci až C4 nebo alkylesterů alikanových (kyselím o počtu atomů uhlíku Ci až C4 a teplotě varu do 180 °C a vody.
3. Způsob podle bodu 1, vyznačující se tím, že na 1,4-benzochinon se působí 2-hydroxy-2-propamsulfonanem vápenatým za teploty —6 až + 5 °C.
4. Způsob podle bodu 1, vyznačující se tím, že se reakce provádí při pH 4 až 6, za přítomnosti uhličitanu vápenatého.
Severografia, n. p., závod 7, Most
Cena 2,40 Kčs
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS848343A CS241843B1 (cs) | 1984-11-05 | 1984-11-05 | Způsob výroby 2,5-dihydroxybenzenswltoaanu vápenatého |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS848343A CS241843B1 (cs) | 1984-11-05 | 1984-11-05 | Způsob výroby 2,5-dihydroxybenzenswltoaanu vápenatého |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS834384A1 CS834384A1 (en) | 1985-08-15 |
| CS241843B1 true CS241843B1 (cs) | 1986-04-17 |
Family
ID=5433849
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS848343A CS241843B1 (cs) | 1984-11-05 | 1984-11-05 | Způsob výroby 2,5-dihydroxybenzenswltoaanu vápenatého |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS241843B1 (cs) |
-
1984
- 1984-11-05 CS CS848343A patent/CS241843B1/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS834384A1 (en) | 1985-08-15 |
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