DE2040643A1 - Verfahren zur Herstellung von Hydroxyphenylessigsaeuren - Google Patents
Verfahren zur Herstellung von HydroxyphenylessigsaeurenInfo
- Publication number
- DE2040643A1 DE2040643A1 DE19702040643 DE2040643A DE2040643A1 DE 2040643 A1 DE2040643 A1 DE 2040643A1 DE 19702040643 DE19702040643 DE 19702040643 DE 2040643 A DE2040643 A DE 2040643A DE 2040643 A1 DE2040643 A1 DE 2040643A1
- Authority
- DE
- Germany
- Prior art keywords
- copper
- acids
- salts
- reaction
- metallic
- 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
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 239000010949 copper Substances 0.000 title claims abstract description 19
- 229910052802 copper Inorganic materials 0.000 title claims abstract description 18
- 150000001879 copper Chemical class 0.000 title claims abstract description 9
- IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical class OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 title claims description 7
- 239000003513 alkali Substances 0.000 title claims description 6
- 239000003054 catalyst Substances 0.000 title description 2
- 125000001475 halogen functional group Chemical group 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims abstract description 11
- 150000007513 acids Chemical class 0.000 claims abstract description 9
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims abstract 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 5
- 229910021592 Copper(II) chloride Inorganic materials 0.000 claims description 3
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical class [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 2
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims 1
- -1 halophenyl acetic acids Chemical class 0.000 abstract description 5
- 235000011054 acetic acid Nutrition 0.000 abstract description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 abstract description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000000843 powder Substances 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 25
- CCVYRRGZDBSHFU-UHFFFAOYSA-N (2-hydroxyphenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1O CCVYRRGZDBSHFU-UHFFFAOYSA-N 0.000 description 17
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- IUJAAIZKRJJZGQ-UHFFFAOYSA-N 2-(2-chlorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1Cl IUJAAIZKRJJZGQ-UHFFFAOYSA-N 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000007127 saponification reaction Methods 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- 239000005749 Copper compound Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000001880 copper compounds Chemical class 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZBQZXTBAGBTUAD-UHFFFAOYSA-N 1,5-dichloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1Cl ZBQZXTBAGBTUAD-UHFFFAOYSA-N 0.000 description 1
- IVEWTCACRDEAOB-UHFFFAOYSA-N 2-(2-methoxyphenyl)acetic acid Chemical compound COC1=CC=CC=C1CC(O)=O IVEWTCACRDEAOB-UHFFFAOYSA-N 0.000 description 1
- KYNNBXCGXUOREX-UHFFFAOYSA-N 2-(3-bromophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1 KYNNBXCGXUOREX-UHFFFAOYSA-N 0.000 description 1
- MGKPFALCNDRSQD-UHFFFAOYSA-N 2-(4-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(F)C=C1 MGKPFALCNDRSQD-UHFFFAOYSA-N 0.000 description 1
- YRNDGUSDBCARGC-UHFFFAOYSA-N 2-methoxyacetophenone Chemical compound COCC(=O)C1=CC=CC=C1 YRNDGUSDBCARGC-UHFFFAOYSA-N 0.000 description 1
- JYJIMEQNTHFXMT-UHFFFAOYSA-N 2-nitro-2-phenylacetic acid Chemical class OC(=O)C([N+]([O-])=O)C1=CC=CC=C1 JYJIMEQNTHFXMT-UHFFFAOYSA-N 0.000 description 1
- RRKMWVISRMWBAL-UHFFFAOYSA-N 3,4-dihydroxy-5-methoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(O)=C1O RRKMWVISRMWBAL-UHFFFAOYSA-N 0.000 description 1
- FBBCSYADXYILEH-UHFFFAOYSA-N 4-hydroxy-3-iodo-5-methoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(I)=C1O FBBCSYADXYILEH-UHFFFAOYSA-N 0.000 description 1
- IPZJPYHEVWLBNH-UHFFFAOYSA-N 5-chloronaphthalen-1-ol Chemical compound C1=CC=C2C(O)=CC=CC2=C1Cl IPZJPYHEVWLBNH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 238000005659 Kindler reaction Methods 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical class OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 150000005204 hydroxybenzenes Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
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)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702040643 DE2040643A1 (de) | 1970-08-17 | 1970-08-17 | Verfahren zur Herstellung von Hydroxyphenylessigsaeuren |
| CH1193871A CH554825A (de) | 1970-08-17 | 1971-08-13 | Verfahren zur herstellung von hydroxyphenylessigsaeuren. |
| SE1035771A SE368001B (OSRAM) | 1970-08-17 | 1971-08-13 | |
| AT710771A AT308079B (de) | 1970-08-17 | 1971-08-13 | Verfahren zur Herstellung von Hydroxyphenylessigsäuren |
| ES394281A ES394281A1 (es) | 1970-08-17 | 1971-08-16 | Procedimiento para la obtencion de acidos hidroxifenilace- ticos. |
| HUBA002628 HU162719B (OSRAM) | 1970-08-17 | 1971-08-17 | |
| BR528671A BR7105286D0 (pt) | 1970-08-17 | 1971-08-17 | Processo para obtencao de acidos hidroxifenilaceticos |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702040643 DE2040643A1 (de) | 1970-08-17 | 1970-08-17 | Verfahren zur Herstellung von Hydroxyphenylessigsaeuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2040643A1 true DE2040643A1 (de) | 1972-02-24 |
Family
ID=5779874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702040643 Pending DE2040643A1 (de) | 1970-08-17 | 1970-08-17 | Verfahren zur Herstellung von Hydroxyphenylessigsaeuren |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT308079B (OSRAM) |
| BR (1) | BR7105286D0 (OSRAM) |
| CH (1) | CH554825A (OSRAM) |
| DE (1) | DE2040643A1 (OSRAM) |
| ES (1) | ES394281A1 (OSRAM) |
| HU (1) | HU162719B (OSRAM) |
| SE (1) | SE368001B (OSRAM) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2401900A1 (fr) * | 1977-08-19 | 1979-03-30 | Oreal | Nouveaux acides (2,5-dihydroxyphenyl) alcanoiques ou leurs sels utiles a titre d'anti-oxydants dans les compositions tinctoriales a base de colorants d'oxydation |
| FR2427820A1 (fr) * | 1978-06-09 | 1980-01-04 | Takeda Chemical Industries Ltd | Produits a base d'acide-phenol pour la prophylaxie et le traitement des fibroses |
| FR2489312A1 (fr) * | 1980-08-29 | 1982-03-05 | Ihara Chemical Ind Co | Procede pour la preparation de derives d'acides hydroxyphenyl aliphatiques et catalyseur utile a cet effet |
| DE4118444A1 (de) * | 1990-06-11 | 1991-12-12 | Ici Plc | Verfahren zur herstellung von (2-hydroxyphenyl)essigsaeure |
| US5167747A (en) * | 1989-02-15 | 1992-12-01 | Kadija Igor V | Apparatus for manufacturing interconnects with fine lines and fine spacing |
-
1970
- 1970-08-17 DE DE19702040643 patent/DE2040643A1/de active Pending
-
1971
- 1971-08-13 SE SE1035771A patent/SE368001B/xx unknown
- 1971-08-13 AT AT710771A patent/AT308079B/de active
- 1971-08-13 CH CH1193871A patent/CH554825A/xx not_active IP Right Cessation
- 1971-08-16 ES ES394281A patent/ES394281A1/es not_active Expired
- 1971-08-17 HU HUBA002628 patent/HU162719B/hu unknown
- 1971-08-17 BR BR528671A patent/BR7105286D0/pt unknown
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2401900A1 (fr) * | 1977-08-19 | 1979-03-30 | Oreal | Nouveaux acides (2,5-dihydroxyphenyl) alcanoiques ou leurs sels utiles a titre d'anti-oxydants dans les compositions tinctoriales a base de colorants d'oxydation |
| FR2427820A1 (fr) * | 1978-06-09 | 1980-01-04 | Takeda Chemical Industries Ltd | Produits a base d'acide-phenol pour la prophylaxie et le traitement des fibroses |
| FR2489312A1 (fr) * | 1980-08-29 | 1982-03-05 | Ihara Chemical Ind Co | Procede pour la preparation de derives d'acides hydroxyphenyl aliphatiques et catalyseur utile a cet effet |
| US5167747A (en) * | 1989-02-15 | 1992-12-01 | Kadija Igor V | Apparatus for manufacturing interconnects with fine lines and fine spacing |
| DE4118444A1 (de) * | 1990-06-11 | 1991-12-12 | Ici Plc | Verfahren zur herstellung von (2-hydroxyphenyl)essigsaeure |
| US5221772A (en) * | 1990-06-11 | 1993-06-22 | Imperial Chemical Industries Plc | Preparation of 2-hydroxyphenyl-acetic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| CH554825A (de) | 1974-10-15 |
| BR7105286D0 (pt) | 1973-05-10 |
| ES394281A1 (es) | 1973-12-16 |
| AT308079B (de) | 1973-06-25 |
| HU162719B (OSRAM) | 1973-04-28 |
| SE368001B (OSRAM) | 1974-06-17 |
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