DE2623836C3 - Verfahren zur Herstellung von Quadratsäure - Google Patents
Verfahren zur Herstellung von QuadratsäureInfo
- Publication number
- DE2623836C3 DE2623836C3 DE2623836A DE2623836A DE2623836C3 DE 2623836 C3 DE2623836 C3 DE 2623836C3 DE 2623836 A DE2623836 A DE 2623836A DE 2623836 A DE2623836 A DE 2623836A DE 2623836 C3 DE2623836 C3 DE 2623836C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- sulfuric acid
- squaric acid
- reaction
- squaric
- 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
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 46
- QXFKQCYWJWBUTR-UHFFFAOYSA-N 1,2,3,3,4,4-hexachlorocyclobutene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C1(Cl)Cl QXFKQCYWJWBUTR-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- RWNKSTSCBHKHTB-UHFFFAOYSA-N Hexachloro-1,3-butadiene Chemical compound ClC(Cl)=C(Cl)C(Cl)=C(Cl)Cl RWNKSTSCBHKHTB-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000001035 drying Methods 0.000 description 3
- QVHWOZCZUNPZPW-UHFFFAOYSA-N 1,2,3,3,4,4-hexafluorocyclobutene Chemical compound FC1=C(F)C(F)(F)C1(F)F QVHWOZCZUNPZPW-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000005201 scrubbing Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- HOMLFECIRZETNN-UHFFFAOYSA-N 1,1,2,3,4-pentachloro-4-ethoxybuta-1,3-diene Chemical compound CCOC(Cl)=C(Cl)C(Cl)=C(Cl)Cl HOMLFECIRZETNN-UHFFFAOYSA-N 0.000 description 1
- KAHIKRWJVIBASP-UHFFFAOYSA-N 1,2-dichloro-3,3,4,4-tetrafluorocyclobutene Chemical compound FC1(F)C(Cl)=C(Cl)C1(F)F KAHIKRWJVIBASP-UHFFFAOYSA-N 0.000 description 1
- NWDONRNKYCKRNT-UHFFFAOYSA-N 2,3,4,4-tetrachlorocyclobut-2-en-1-one Chemical compound ClC1=C(Cl)C(Cl)(Cl)C1=O NWDONRNKYCKRNT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
- 235000019392 nitrosyl chloride Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- -1 trichloromorpholinobutadiene Chemical compound 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/707—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups a keto group being part of a three- to five-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/42—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis
- C07C45/43—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis of >CX2 groups, X being halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2623836A DE2623836C3 (de) | 1976-05-28 | 1976-05-28 | Verfahren zur Herstellung von Quadratsäure |
| AU23433/77A AU502227B2 (en) | 1976-05-28 | 1977-03-21 | Process for preparing diketocyclobutenediol |
| FR7714676A FR2352778A1 (fr) | 1976-05-28 | 1977-05-13 | Procede de preparation de la 1,2-dihydroxy-cyclobutene-dione-(3,4) denommee acide quadratique |
| US05/798,546 US4097530A (en) | 1976-05-28 | 1977-05-19 | Process for the production of squaric acid |
| SU772483402A SU645549A3 (ru) | 1976-05-28 | 1977-05-23 | Способ получени 1,2-диоксициклобутендиона-3,4 |
| CA279,130A CA1075717A (en) | 1976-05-28 | 1977-05-25 | Process for the preparation of 1,2-dihydroxycyclobutenedione-(3,4) |
| CS773457A CS193095B2 (en) | 1976-05-28 | 1977-05-25 | Process for preparing 1,2-dihydroxycyclobuten 3,4-dione |
| AT377177A AT349445B (de) | 1976-05-28 | 1977-05-26 | Verfahren zur herstellung von quadratsaeure |
| IT49563/77A IT1079672B (it) | 1976-05-28 | 1977-05-26 | Procedimento per produrre acido quadratico |
| CH651977A CH629469A5 (de) | 1976-05-28 | 1977-05-26 | Verfahren zur herstellung von quadratsaeure. |
| JP6128877A JPS52148046A (en) | 1976-05-28 | 1977-05-27 | Process for manufacture of square acid |
| BE178018A BE855165A (fr) | 1976-05-28 | 1977-05-27 | Procede de production de l'acide quadrique |
| NO771871A NO146278C (no) | 1976-05-28 | 1977-05-27 | Fremgangsmaate til fremstilling av kvadratsyre |
| DD7700199184A DD129774A1 (de) | 1976-05-28 | 1977-05-27 | Verfahren zur herstellung von quadratsaeure |
| DK236677A DK236677A (da) | 1976-05-28 | 1977-05-27 | Fremgangsmade til fremstilling af kvadratsyre |
| NL7705890A NL7705890A (nl) | 1976-05-28 | 1977-05-27 | Werkwijze ter bereiding van quadraatzuur. |
| BR7703445A BR7703445A (pt) | 1976-05-28 | 1977-05-27 | Processo para a preparacao de acido quadratico |
| SE7706262A SE421787B (sv) | 1976-05-28 | 1977-05-27 | Forfarande for framstellning av kvadratsyra |
| GB22451/77A GB1574500A (en) | 1976-05-28 | 1977-05-27 | Process for the production of squaric acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2623836A DE2623836C3 (de) | 1976-05-28 | 1976-05-28 | Verfahren zur Herstellung von Quadratsäure |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2623836A1 DE2623836A1 (de) | 1977-12-01 |
| DE2623836B2 DE2623836B2 (de) | 1978-04-27 |
| DE2623836C3 true DE2623836C3 (de) | 1978-12-21 |
Family
ID=5979159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2623836A Expired DE2623836C3 (de) | 1976-05-28 | 1976-05-28 | Verfahren zur Herstellung von Quadratsäure |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4097530A (enExample) |
| JP (1) | JPS52148046A (enExample) |
| AT (1) | AT349445B (enExample) |
| AU (1) | AU502227B2 (enExample) |
| BE (1) | BE855165A (enExample) |
| BR (1) | BR7703445A (enExample) |
| CA (1) | CA1075717A (enExample) |
| CH (1) | CH629469A5 (enExample) |
| CS (1) | CS193095B2 (enExample) |
| DD (1) | DD129774A1 (enExample) |
| DE (1) | DE2623836C3 (enExample) |
| DK (1) | DK236677A (enExample) |
| FR (1) | FR2352778A1 (enExample) |
| GB (1) | GB1574500A (enExample) |
| IT (1) | IT1079672B (enExample) |
| NL (1) | NL7705890A (enExample) |
| NO (1) | NO146278C (enExample) |
| SE (1) | SE421787B (enExample) |
| SU (1) | SU645549A3 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2810398C2 (de) * | 1978-03-10 | 1983-08-25 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur Herstellung von Tetrachlorcyclobutenon aus Hexachlorcyclobuten |
| DE2824558C3 (de) * | 1978-06-05 | 1981-07-09 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur Herstellung von Quadratsäure |
| DE3314431A1 (de) * | 1983-04-21 | 1984-10-25 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von quadratsaeure |
| US4508803A (en) * | 1983-12-05 | 1985-04-02 | Xerox Corporation | Photoconductive devices containing novel benzyl fluorinated squaraine compositions |
| IE64516B1 (en) * | 1990-02-12 | 1995-08-09 | Lonza Ag | A process for the preparation of quadratic acid |
| IE65907B1 (en) * | 1990-02-26 | 1995-11-29 | Lonza Ag | New 3-hydroxy-2-cyclobuten-1-one salts their preparation and use |
| CA2394847C (en) * | 1999-11-30 | 2007-01-16 | Electric Power Research Institute | Capillary electrophoresis probes and method |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1404928A (fr) * | 1963-08-24 | 1965-07-02 | Huels Chemische Werke Ag | Procédé de préparation du dicéto-cyclobutène-diol |
| DE1253266B (de) * | 1963-08-24 | 1967-11-02 | Huels Chemische Werke Ag | Verfahren zur Herstellung von Dioxocyclobutendiol |
| BE786650A (fr) * | 1971-07-24 | 1973-01-24 | Ercoli Raffaele | Procede de preparation de l'acide squarique |
-
1976
- 1976-05-28 DE DE2623836A patent/DE2623836C3/de not_active Expired
-
1977
- 1977-03-21 AU AU23433/77A patent/AU502227B2/en not_active Expired
- 1977-05-13 FR FR7714676A patent/FR2352778A1/fr active Granted
- 1977-05-19 US US05/798,546 patent/US4097530A/en not_active Expired - Lifetime
- 1977-05-23 SU SU772483402A patent/SU645549A3/ru active
- 1977-05-25 CA CA279,130A patent/CA1075717A/en not_active Expired
- 1977-05-25 CS CS773457A patent/CS193095B2/cs unknown
- 1977-05-26 IT IT49563/77A patent/IT1079672B/it active
- 1977-05-26 AT AT377177A patent/AT349445B/de not_active IP Right Cessation
- 1977-05-26 CH CH651977A patent/CH629469A5/de not_active IP Right Cessation
- 1977-05-27 BE BE178018A patent/BE855165A/xx unknown
- 1977-05-27 NL NL7705890A patent/NL7705890A/xx not_active Application Discontinuation
- 1977-05-27 DK DK236677A patent/DK236677A/da not_active Application Discontinuation
- 1977-05-27 JP JP6128877A patent/JPS52148046A/ja active Pending
- 1977-05-27 NO NO771871A patent/NO146278C/no unknown
- 1977-05-27 DD DD7700199184A patent/DD129774A1/xx unknown
- 1977-05-27 SE SE7706262A patent/SE421787B/xx unknown
- 1977-05-27 GB GB22451/77A patent/GB1574500A/en not_active Expired
- 1977-05-27 BR BR7703445A patent/BR7703445A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU502227B2 (en) | 1979-07-19 |
| BR7703445A (pt) | 1978-02-28 |
| US4097530A (en) | 1978-06-27 |
| NO771871L (no) | 1977-11-29 |
| AU2343377A (en) | 1978-09-28 |
| SE421787B (sv) | 1982-02-01 |
| SE7706262L (sv) | 1977-11-29 |
| CS193095B2 (en) | 1979-09-17 |
| ATA377177A (de) | 1978-09-15 |
| DD129774A1 (de) | 1978-02-08 |
| NO146278C (no) | 1982-09-01 |
| DK236677A (da) | 1977-11-29 |
| JPS52148046A (en) | 1977-12-08 |
| AT349445B (de) | 1979-04-10 |
| BE855165A (fr) | 1977-11-28 |
| CA1075717A (en) | 1980-04-15 |
| CH629469A5 (de) | 1982-04-30 |
| FR2352778B1 (enExample) | 1980-07-25 |
| FR2352778A1 (fr) | 1977-12-23 |
| GB1574500A (en) | 1980-09-10 |
| NL7705890A (nl) | 1977-11-30 |
| SU645549A3 (ru) | 1979-01-30 |
| DE2623836B2 (de) | 1978-04-27 |
| NO146278B (no) | 1982-05-24 |
| DE2623836A1 (de) | 1977-12-01 |
| IT1079672B (it) | 1985-05-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2623836C3 (de) | Verfahren zur Herstellung von Quadratsäure | |
| CH631956A5 (de) | Verfahren zur herstellung von 2,5-dichlorphenol. | |
| DE3308922A1 (de) | Verfahren zur herstellung von fettsaeureestern der ascorbinsaeure | |
| DE2021297A1 (de) | Verfahren zur Herstellung von schwefelhaltigen Phenolen | |
| DE2105014A1 (de) | Verfahren zur Herstellung von Furanonen | |
| DE1643329A1 (de) | Verfahren zur Herstellung von Nitroaminodiarylaethern | |
| DE2237750C2 (de) | Verfahren zur Herstellung von Brenzcatechin | |
| EP0157225B1 (de) | Verfahren zur Herstellung von Benzimidazolyl,-Benzoxazolyl- und Benzthiazolyloxyphenoxypropionsäurederivaten | |
| DE503205C (de) | Verfahren zur Herstellung von Kondensationsprodukten der Anthrachinonreihe | |
| DE2040643A1 (de) | Verfahren zur Herstellung von Hydroxyphenylessigsaeuren | |
| DE2306611C3 (de) | Verfahren zur Herstellung von 1,5und 1,8-Dinitroanthrachinon | |
| EP0037474B1 (de) | Verfahren zur Herstellung von 1-Acetoxy-3-chlor-pentan-4-on | |
| DE3146471C2 (de) | Verfahren zur Herstellung von 1-(3,5-Dimethoxy-4-hydroxyphenyl)-2-(N-methylamino)-ethanol-hydrochlorid | |
| DE2810305C2 (enExample) | ||
| DE953072C (de) | Verfahren zur Herstellung von Naphthalin-2, 6-dicarbonsaeure bzw. von deren Salzen und Derivaten | |
| CH633245A5 (de) | Verfahren zur herstellung von 2,3-dichlor-1-(c1-7)-alkoxybenzolen. | |
| EP0001582B1 (de) | Verfahren zur Herstellung von Bis-triazolylstilbenen | |
| DE2117034A1 (de) | Verfahren zur Herstellung von 2,4,7 Tn mtrofluorenon | |
| DE2824558B2 (de) | Verfahren zur Herstellung von Quadratsäure | |
| DE506442C (de) | Verfahren zur Oxydation von Acylamino-ª‡-naphtholen | |
| EP0057665B1 (de) | Verfahren zur Herstellung von 1-Acylamino-3,4-phthaloyl-acridonen | |
| DE1543960C (de) | Verfahren zur Herstellung von Naphthol mit überwiegendem alpha Naphthol Gehalt durch alkalische Hydrolyse von Monochlor naphthalin | |
| DE1168408B (de) | Verfahren zur Herstellung von ª‰-Methylmercaptopropionaldehyd | |
| DE2513952C2 (de) | Verfahren zur herstellung von monochlorbenzoesaeuren | |
| DE2459233C2 (de) | Verfahren zur Herstellung von Hydrochinon |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: HUELS AG, 4370 MARL, DE |
|
| 8339 | Ceased/non-payment of the annual fee |