DE1543520B1 - Verfahren zur Herstellung von Dibromsalicylsaeure - Google Patents
Verfahren zur Herstellung von DibromsalicylsaeureInfo
- Publication number
- DE1543520B1 DE1543520B1 DE19661543520 DE1543520A DE1543520B1 DE 1543520 B1 DE1543520 B1 DE 1543520B1 DE 19661543520 DE19661543520 DE 19661543520 DE 1543520 A DE1543520 A DE 1543520A DE 1543520 B1 DE1543520 B1 DE 1543520B1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- bromine
- reaction
- dioxane
- dibromosalicylic
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 3
- NVWSLNRSPZAQOK-UHFFFAOYSA-N 3,4-dibromo-2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C(Br)=C1O NVWSLNRSPZAQOK-UHFFFAOYSA-N 0.000 title description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 21
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 20
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 10
- 229960004889 salicylic acid Drugs 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- BFBZHSOXKROMBG-UHFFFAOYSA-N 3,5-dibromo-2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC(Br)=CC(Br)=C1O BFBZHSOXKROMBG-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000005893 bromination reaction Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000031709 bromination Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- WACBJMRDDSHLDH-UHFFFAOYSA-N 2-bromooxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OBr WACBJMRDDSHLDH-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- -1 monobromosalicyl Chemical group 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US486200A US3381032A (en) | 1965-09-09 | 1965-09-09 | Preparation of 3, 5-dibromo-salicylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1543520B1 true DE1543520B1 (de) | 1970-12-17 |
Family
ID=23930992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661543520 Pending DE1543520B1 (de) | 1965-09-09 | 1966-06-23 | Verfahren zur Herstellung von Dibromsalicylsaeure |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3381032A (https=) |
| BE (1) | BE686705A (https=) |
| CH (1) | CH468336A (https=) |
| DE (1) | DE1543520B1 (https=) |
| GB (1) | GB1147513A (https=) |
| NL (1) | NL6610859A (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5013866A (en) * | 1989-11-28 | 1991-05-07 | Baxter International Inc. | Pharmaceutical grade 3,5-dibromosalicylic acid and metohd for synthesizing same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3152177A (en) * | 1964-10-06 | Brominatign of salicylanilide |
-
1965
- 1965-09-09 US US486200A patent/US3381032A/en not_active Expired - Lifetime
-
1966
- 1966-06-23 DE DE19661543520 patent/DE1543520B1/de active Pending
- 1966-07-15 CH CH1030266A patent/CH468336A/de unknown
- 1966-08-02 NL NL6610859A patent/NL6610859A/xx unknown
- 1966-09-05 GB GB39543/66A patent/GB1147513A/en not_active Expired
- 1966-09-09 BE BE686705D patent/BE686705A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| CH468336A (de) | 1969-02-15 |
| US3381032A (en) | 1968-04-30 |
| NL6610859A (https=) | 1967-03-10 |
| GB1147513A (en) | 1969-04-02 |
| BE686705A (https=) | 1967-03-09 |
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