CS197992B1 - Process for preparing bromsulphophthaleines - Google Patents
Process for preparing bromsulphophthaleines Download PDFInfo
- Publication number
- CS197992B1 CS197992B1 CS524978A CS524978A CS197992B1 CS 197992 B1 CS197992 B1 CS 197992B1 CS 524978 A CS524978 A CS 524978A CS 524978 A CS524978 A CS 524978A CS 197992 B1 CS197992 B1 CS 197992B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- bromine
- acetic acid
- glacial acetic
- bromination
- chlorine
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 229960000583 acetic acid Drugs 0.000 claims description 9
- 239000012362 glacial acetic acid Substances 0.000 claims description 9
- 230000031709 bromination Effects 0.000 claims description 8
- 238000005893 bromination reaction Methods 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 3
- 238000007664 blowing Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
- PRZSXZWFJHEZBJ-UHFFFAOYSA-N thymol blue Chemical compound C1=C(O)C(C(C)C)=CC(C2(C3=CC=CC=C3S(=O)(=O)O2)C=2C(=CC(O)=C(C(C)C)C=2)C)=C1C PRZSXZWFJHEZBJ-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Vynález se týká způsobu výroby dibrom a tetrabromsulfoftaleinů, sloučenin, používaných jako analytické indikátory.The invention relates to a process for the preparation of dibromo and tetrabromosulfophthaleins, compounds used as analytical indicators.
Brómované sulfoftaleiny se doposud připravují bromaci příslušných sulfoftaleinů bromem v molárnim poměru nebo nadbytku v přostředí ledové kyseliny octové nebo absolutního alkoholu (Chrzaszczewski , Kosinski M.: Zes. II., Nauki Mat.-Przyrod. No 3, 145-57 (1957); Freas R., Provine E.A.: 3.Am.Chem.Soc. 50, 2014 (1928); Lemingar 0.: Chsm. průmysl 5/30 str. 10 (1955); Lubs H.A., Acree S.F.: 3.Am.Chem.Soc. 38, 2772 (1916). Lze je též připravit bromaci příslušných sulfoftaleinů bromnanem sodným ve vodném prostředí (SSSR pat.Brominated sulfophthaleins have so far been prepared by bromination of the corresponding sulfophthaleins with bromine in a molar ratio or excess in a glacial acetic acid or absolute alcohol medium (Chrzaszczewski, Kosinski M .: Zes. II., Nauki Mat.-Przyrod. No 3, 145-57 (1957); Freas R., Provine EA: 3rd Am.Chem.Soc., 50, 2014 (1928), Lemingar 0: Chemical Industry 5/30 p.10 (1955), Lubs HA, Acree SF: 3rd Am.Chem Soc. 38, 2772 (1916) It is also possible to prepare bromination of the corresponding sulfophthaleins with sodium hypobromite in an aqueous medium (USSR Pat.
127 154).127 154).
Brom je látka drahá a jeho dostupnost je omezena. Při bromaci sulfoftaleinů je ho * třeba značné množstvi, jednak na vlastni bromaci látky, jednak na vznik vedlejšího produktu - bromovodlku. Tuto nevýhodu způsobu bromace snižuje způsob popsaný ve vynálezu 3eho podstata spočívá v tom, že se bromace sulfoftaleinů bromem v prostředí ledové kyseliny octové nebo alkoholu provádí tak, že se bromovodik při reakci oxiduje chlorem na brom, který se dále zúčaetSuje reakce. Tim ee na bromaci spotřebuje pouze část dřivé potřebného množství bromu. Pro přípravu dibromsulfoftaleinů je výhodné použit molórní poměr sulfoftalein : brom : chlor 1 : 1 až 1,5 : 0,5 až 1 e pro tetrabromeulfofteleiny 1 : 2 až 3 : 1 až 3.Bromine is expensive and its availability is limited. In the bromination of sulfophthaleins, a considerable amount is required, both for the actual bromination of the substance and for the formation of the by-product - hydrogen bromide. This disadvantage of the bromination process is reduced by the process described in the invention. The principle is that bromination of sulfophthaleins with bromine in glacial acetic acid or alcohol is carried out by oxidizing the hydrogen bromide with chlorine to bromine in the reaction, which further utilizes the reaction. Thus, the bromination consumes only a portion of the prior bromine required. For the preparation of dibromosulfophthaleins, it is preferable to use a molar ratio of sulfophthalein: bromine: chlorine of 1: 1 to 1.5: 0.5 to 1 e for tetrabromeulfophthalines of 1: 2 to 3: 1 to 3.
197 992197 992
Přiklad 1Example 1
Přloravi sj^.o^tetnbroBifenoliulřoftfllolnu □o třihrdlé baňky o obsahu 250 ml opatřené michadlem, teploměrem, dělicí nálevkou a trubici pro vháněni chloru se vnese 10,6 g (0,03 mol) fenolové červeně a 30 ml ledové kyseliny octové. Potom se při teplotě 20 až 35 °C za mícháni přlkape roztok 12,8 g (0,08 mol) bromu v 5 ml ledové kyseliny octové. Po přidáni bromu ee reakčnl směs míchá 15 minut a potom ee do ni ze míchání při teplotě do 50 °C vhání chlor v celkovém množství 4,2 g (0,06 mol). Potom ee reakčnl směe vyhřeje na 80 °C a při této teplotě ee míchá 30 minut. Po ochlazeni na 30 °C se vyloučené barvivo odsaje, promyje na filtru 10 ml ledové kyseliny octové a 10 ml ledové vody.Transfer to a 250 ml three-necked 250 ml three-necked flask equipped with a stirrer, thermometer, separating funnel and chlorine blowing tube and add 10.6 g (0.03 mol) of phenolic red and 30 ml of glacial acetic acid. A solution of 12.8 g (0.08 mol) of bromine in 5 ml of glacial acetic acid was then added dropwise with stirring at 20-35 ° C. After addition of bromine, the reaction mixture was stirred for 15 minutes and then chlorine was blown into the mixture from stirring at a temperature of up to 50 ° C in a total amount of 4.2 g (0.06 mol). The reaction mixture was then heated to 80 ° C and stirred at 80 ° C for 30 minutes. After cooling to 30 ° C, the precipitated dye is filtered off with suction, washed on a filter with 10 ml of glacial acetic acid and 10 ml of ice water.
Výtěžek 78 % teorie.Yield: 78%.
Přiklad 2Example 2
Příprava 3,3'-dibromthymolaulfoftaleinuPreparation of 3,3'-dibromothymolaulfophthalein
Do třihrdlé baňky o obsahu 750 ml, opatřené michadlem, teploměřem, dělicí nálevkou a trubici pro vháněni chloru se vnese 150 g (0,3 mol) thymolové modři a 300 ml ledové kyseliny octové. Potom ee při teplotě 20 až 35 °C přlkape za mícháni roztok bromu, připravený z 64 g (0,4 mol) bromu a 50 ml ledové kyseliny octové. Po přidání roztoku bromu ee reakčnl směs míchá 10 minut a potom se do ni při teplotě do 50 °C vhání celkem 14,2 g (0,2 mol) chloru. Potom se reakčnl směe vyhřeje na 60 °C a při této teplotě se míchá 1 hodinu. Po ochlazeni na 15 až 20 °C se odfiltruje vyloučené barvivo a promyje se na filtru 200'ml ledové kyseliny octové.A 750 ml three-necked flask equipped with a stirrer, a thermometer, a separating funnel and a chlorine blowing tube was charged with 150 g (0.3 mol) of thymol blue and 300 ml of glacial acetic acid. A solution of bromine prepared from 64 g (0.4 mol) of bromine and 50 ml of glacial acetic acid was added dropwise with stirring at 20-35 ° C. After addition of the bromine solution, the reaction mixture was stirred for 10 minutes and then a total of 14.2 g (0.2 mol) of chlorine was introduced into the mixture at a temperature below 50 ° C. The reaction mixture was then heated to 60 ° C and stirred at this temperature for 1 hour. After cooling to 15-20 ° C, the precipitated dye is filtered off and washed on the filter with 200 ml of glacial acetic acid.
Výtěžek 139 g (172 % teorie).Yield 139 g (172% of theory).
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS524978A CS197992B1 (en) | 1978-08-11 | 1978-08-11 | Process for preparing bromsulphophthaleines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS524978A CS197992B1 (en) | 1978-08-11 | 1978-08-11 | Process for preparing bromsulphophthaleines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS197992B1 true CS197992B1 (en) | 1980-05-30 |
Family
ID=5397017
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS524978A CS197992B1 (en) | 1978-08-11 | 1978-08-11 | Process for preparing bromsulphophthaleines |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS197992B1 (en) |
-
1978
- 1978-08-11 CS CS524978A patent/CS197992B1/en unknown
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