CA1055939A - Process for preparing diesters of 2,5-dihydroxybenzene sulfonic acid - Google Patents
Process for preparing diesters of 2,5-dihydroxybenzene sulfonic acidInfo
- Publication number
- CA1055939A CA1055939A CA252,259A CA252259A CA1055939A CA 1055939 A CA1055939 A CA 1055939A CA 252259 A CA252259 A CA 252259A CA 1055939 A CA1055939 A CA 1055939A
- Authority
- CA
- Canada
- Prior art keywords
- salt
- sulfonic acid
- butyrate
- phenoxyiso
- chloro
- 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
- IKQCSJBQLWJEPU-UHFFFAOYSA-N 2,5-dihydroxybenzenesulfonic acid Chemical compound OC1=CC=C(O)C(S(O)(=O)=O)=C1 IKQCSJBQLWJEPU-UHFFFAOYSA-N 0.000 title claims description 26
- 150000005690 diesters Chemical class 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical class CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims description 17
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical class CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 claims description 12
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- 125000001664 diethylamino group Chemical class [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 150000002780 morpholines Chemical class 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 5
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims 12
- 239000000126 substance Substances 0.000 claims 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 1
- 150000007514 bases Chemical class 0.000 claims 1
- -1 Amine salts Chemical class 0.000 abstract description 2
- TXCGAZHTZHNUAI-UHFFFAOYSA-N clofibric acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 TXCGAZHTZHNUAI-UHFFFAOYSA-N 0.000 abstract description 2
- CTLTUPWEUCZSIP-UHFFFAOYSA-N 1,4-dihydroxycyclohexa-2,4-diene-1-sulfonic acid Chemical class OC1=CCC(O)(S(O)(=O)=O)C=C1 CTLTUPWEUCZSIP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003315 2-(4-chlorophenoxy)-2-methylpropanoic acid Substances 0.000 abstract 1
- 229950008441 clofibric acid Drugs 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000013078 crystal Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VZYDKJOUEPFKMW-UHFFFAOYSA-N 2,3-dihydroxybenzenesulfonic acid Chemical compound OC1=CC=CC(S(O)(=O)=O)=C1O VZYDKJOUEPFKMW-UHFFFAOYSA-N 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- QAHQHYFLYHVYNX-UHFFFAOYSA-N cyclohexa-1,4-diene-1-sulfonic acid Chemical compound OS(=O)(=O)C1=CCC=CC1 QAHQHYFLYHVYNX-UHFFFAOYSA-N 0.000 description 1
- 238000000326 densiometry Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000007666 subchronic toxicity Effects 0.000 description 1
- 231100000195 subchronic toxicity Toxicity 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- MDYZKJNTKZIUSK-UHFFFAOYSA-N tyloxapol Chemical compound O=C.C1CO1.CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 MDYZKJNTKZIUSK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH633275A CH591438A5 (en)van) | 1975-05-16 | 1975-05-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1055939A true CA1055939A (en) | 1979-06-05 |
Family
ID=4307867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA252,259A Expired CA1055939A (en) | 1975-05-16 | 1976-05-11 | Process for preparing diesters of 2,5-dihydroxybenzene sulfonic acid |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS51148011A (en)van) |
| AU (1) | AU1107276A (en)van) |
| BE (1) | BE838182R (en)van) |
| CA (1) | CA1055939A (en)van) |
| CH (1) | CH591438A5 (en)van) |
| DD (1) | DD125201A6 (en)van) |
| DE (1) | DE2618450A1 (en)van) |
| DK (1) | DK131476A (en)van) |
| FR (1) | FR2310755A2 (en)van) |
| GB (1) | GB1500481A (en)van) |
| NL (1) | NL182050C (en)van) |
| RO (1) | RO72828A (en)van) |
| ZA (1) | ZA76689B (en)van) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH563356A5 (en)van) * | 1972-05-17 | 1975-06-30 | Esteve Dr Lab Del Sa | |
| AR204506A1 (es) * | 1972-05-17 | 1976-02-12 | Esteve Labor Dr | Procedimiento de preparacion de sales de acidos p-dihidroxibencenodisulfonicos |
| CH551956A (fr) * | 1972-05-17 | 1974-07-31 | Esteve Lab Del Dr Sa | Procede pour la preparation de sels de sulfones derivant des acides 2,5-dihydroxybenzenemonosulfonique et 2,5dihydroxybenzenedisulfonique. |
-
1975
- 1975-05-16 CH CH633275A patent/CH591438A5/xx not_active IP Right Cessation
- 1975-12-20 RO RO7584261A patent/RO72828A/ro unknown
-
1976
- 1976-01-20 NL NLAANVRAGE7600527,A patent/NL182050C/xx active Search and Examination
- 1976-01-23 FR FR7601920A patent/FR2310755A2/fr active Granted
- 1976-01-29 GB GB3629/76A patent/GB1500481A/en not_active Expired
- 1976-02-02 BE BE164018A patent/BE838182R/xx not_active IP Right Cessation
- 1976-02-06 ZA ZA760689A patent/ZA76689B/xx unknown
- 1976-02-12 AU AU11072/76A patent/AU1107276A/en not_active Expired
- 1976-03-25 DK DK131476A patent/DK131476A/da unknown
- 1976-04-27 DE DE19762618450 patent/DE2618450A1/de active Granted
- 1976-05-11 CA CA252,259A patent/CA1055939A/en not_active Expired
- 1976-05-14 DD DD192854A patent/DD125201A6/xx unknown
- 1976-05-14 JP JP51054442A patent/JPS51148011A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CH591438A5 (en)van) | 1977-09-15 |
| BE838182R (fr) | 1976-05-28 |
| NL182050B (nl) | 1987-08-03 |
| FR2310755A2 (fr) | 1976-12-10 |
| DE2618450C2 (en)van) | 1987-11-12 |
| JPS51148011A (en) | 1976-12-18 |
| AU1107276A (en) | 1977-08-18 |
| GB1500481A (en) | 1978-02-08 |
| DE2618450A1 (de) | 1976-11-25 |
| FR2310755B2 (en)van) | 1978-11-03 |
| ZA76689B (en) | 1977-09-28 |
| DD125201A6 (en)van) | 1977-04-06 |
| NL182050C (nl) | 1988-01-04 |
| NL7600527A (nl) | 1976-11-18 |
| RO72828A (ro) | 1981-05-30 |
| DK131476A (da) | 1976-11-17 |
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