DE2052253A1 - 2-hydroxy-3-carboxy-naphthaldehyde-1 - in high yield from a bis (naphthylideneimino)methane - Google Patents
2-hydroxy-3-carboxy-naphthaldehyde-1 - in high yield from a bis (naphthylideneimino)methaneInfo
- Publication number
- DE2052253A1 DE2052253A1 DE19702052253 DE2052253A DE2052253A1 DE 2052253 A1 DE2052253 A1 DE 2052253A1 DE 19702052253 DE19702052253 DE 19702052253 DE 2052253 A DE2052253 A DE 2052253A DE 2052253 A1 DE2052253 A1 DE 2052253A1
- Authority
- DE
- Germany
- Prior art keywords
- hydroxy
- naphthaldehyde
- carboxy
- acid
- parts
- 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
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000004312 hexamethylene tetramine Substances 0.000 claims abstract description 15
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims description 19
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 abstract description 8
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 8
- 150000001735 carboxylic acids Chemical class 0.000 abstract description 3
- 239000000975 dye Substances 0.000 abstract description 2
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 abstract 1
- 208000000655 Distemper Diseases 0.000 abstract 1
- 239000000976 ink Substances 0.000 abstract 1
- 239000004922 lacquer Substances 0.000 abstract 1
- 229960004011 methenamine Drugs 0.000 abstract 1
- 239000003973 paint Substances 0.000 abstract 1
- 229920003023 plastic Polymers 0.000 abstract 1
- 239000004033 plastic Substances 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- 239000002253 acid Substances 0.000 description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- LPRBZICETYEWOZ-UHFFFAOYSA-N 4-formyl-3-hydroxynaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C(C=O)=C(O)C(C(=O)O)=CC2=C1 LPRBZICETYEWOZ-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000012362 glacial acetic acid Substances 0.000 description 9
- 239000013067 intermediate product Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
- 238000007013 Reimer-Tiemann formylation reaction Methods 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- -1 aromatic hydroxy compounds Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920002866 paraformaldehyde Polymers 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- OTJFQRMIRKXXRS-UHFFFAOYSA-N (hydroxymethylamino)methanol Chemical class OCNCO OTJFQRMIRKXXRS-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KAGRCSIJBVBXLY-UHFFFAOYSA-N 1-(aminomethyl)naphthalen-2-ol Chemical compound C1=CC=C2C(CN)=C(O)C=CC2=C1 KAGRCSIJBVBXLY-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- NWAYBGZOQHXONN-UHFFFAOYSA-N B(O)(O)O.C(C)OC(C)O Chemical compound B(O)(O)O.C(C)OC(C)O NWAYBGZOQHXONN-UHFFFAOYSA-N 0.000 description 1
- 101100387923 Caenorhabditis elegans dos-1 gene Proteins 0.000 description 1
- MMOXZBCLCQITDF-UHFFFAOYSA-N N,N-diethyl-m-toluamide Chemical compound CCN(CC)C(=O)C1=CC=CC(C)=C1 MMOXZBCLCQITDF-UHFFFAOYSA-N 0.000 description 1
- 241000681032 Neobarbella comes Species 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- ITBPIKUGMIZTJR-UHFFFAOYSA-N [bis(hydroxymethyl)amino]methanol Chemical compound OCN(CO)CO ITBPIKUGMIZTJR-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- PEEKVIHQOHJITP-UHFFFAOYSA-N boric acid;propane-1,2,3-triol Chemical compound OB(O)O.OCC(O)CO PEEKVIHQOHJITP-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/30—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing —CHO groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B55/00—Azomethine dyes
- C09B55/005—Disazomethine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702052253 DE2052253A1 (en) | 1970-10-24 | 1970-10-24 | 2-hydroxy-3-carboxy-naphthaldehyde-1 - in high yield from a bis (naphthylideneimino)methane |
| CH491071A CH558413A (de) | 1970-04-27 | 1971-04-05 | Verfahren zur herstellung eines dis-azomethins. |
| US00137072A US3839434A (en) | 1970-04-27 | 1971-04-23 | Amidine substituted naphthalene carboxylic acid |
| GB1132271*[A GB1341462A (en) | 1970-04-27 | 1971-04-26 | Azomethine useful for the production of 2-hydroxy-3-caboxy- naphthaldehyde 1 |
| FR7114976A FR2090791A5 (enExample) | 1970-04-27 | 1971-04-27 | |
| CS7355A CS165362B2 (enExample) | 1970-10-24 | 1971-10-20 | |
| SU1707495A SU437306A3 (ru) | 1970-10-24 | 1971-10-20 | Способ получения дисазометинового пигмента |
| NL7114521A NL7114521A (enExample) | 1970-10-24 | 1971-10-21 | |
| DK514471A DK133386C (da) | 1970-10-24 | 1971-10-22 | Disazomethinpigmenter til anvendelse ved farvning af lakker trykfarver og formstoffer og en fremgangsmade til fremstillingaf sadanne pigmenter |
| BE774306A BE774306A (fr) | 1970-10-24 | 1971-10-22 | Pigments bisazomethiniques |
| ES396313A ES396313A1 (es) | 1970-10-24 | 1971-10-23 | Procedimiento para la obtencion de 2-hidroxi-3-carboxi-naf-taldehido-(1). |
| BR7135/71A BR7107135D0 (pt) | 1970-10-24 | 1971-10-25 | Processo para fabricacao de um pigmento de disazometria |
| AU34936/71A AU456447B2 (en) | 1970-10-24 | 1971-10-25 | Disazomethine pigments |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702052253 DE2052253A1 (en) | 1970-10-24 | 1970-10-24 | 2-hydroxy-3-carboxy-naphthaldehyde-1 - in high yield from a bis (naphthylideneimino)methane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2052253A1 true DE2052253A1 (en) | 1972-06-15 |
Family
ID=5786025
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702052253 Pending DE2052253A1 (en) | 1970-04-27 | 1970-10-24 | 2-hydroxy-3-carboxy-naphthaldehyde-1 - in high yield from a bis (naphthylideneimino)methane |
Country Status (6)
| Country | Link |
|---|---|
| BR (1) | BR7107135D0 (enExample) |
| CS (1) | CS165362B2 (enExample) |
| DE (1) | DE2052253A1 (enExample) |
| ES (1) | ES396313A1 (enExample) |
| NL (1) | NL7114521A (enExample) |
| SU (1) | SU437306A3 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2319614A1 (fr) * | 1975-07-30 | 1977-02-25 | Hoechst Ag | Nouveaux hydroxy-2 naphtaldehydes-1, leur preparation et leur utilisation dans la preparation de colorants azomethiniques |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MD4174C1 (ro) * | 2011-10-25 | 2013-01-31 | Институт Химии Академии Наук Молдовы | Derivaţi tiosemicarbazonici ai acidului 4-formil-3-hidroxi-2-naftoic cu proprietăţi antibacteriene |
-
1970
- 1970-10-24 DE DE19702052253 patent/DE2052253A1/de active Pending
-
1971
- 1971-10-20 CS CS7355A patent/CS165362B2/cs unknown
- 1971-10-20 SU SU1707495A patent/SU437306A3/ru active
- 1971-10-21 NL NL7114521A patent/NL7114521A/xx unknown
- 1971-10-23 ES ES396313A patent/ES396313A1/es not_active Expired
- 1971-10-25 BR BR7135/71A patent/BR7107135D0/pt unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2319614A1 (fr) * | 1975-07-30 | 1977-02-25 | Hoechst Ag | Nouveaux hydroxy-2 naphtaldehydes-1, leur preparation et leur utilisation dans la preparation de colorants azomethiniques |
Also Published As
| Publication number | Publication date |
|---|---|
| SU437306A3 (ru) | 1974-07-25 |
| CS165362B2 (enExample) | 1975-12-22 |
| ES396313A1 (es) | 1974-05-01 |
| BR7107135D0 (pt) | 1973-05-31 |
| NL7114521A (enExample) | 1972-04-26 |
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