DE2261984A1 - Verfahren zur herstellung von fluoranverbindungen - Google Patents
Verfahren zur herstellung von fluoranverbindungenInfo
- Publication number
- DE2261984A1 DE2261984A1 DE19722261984 DE2261984A DE2261984A1 DE 2261984 A1 DE2261984 A1 DE 2261984A1 DE 19722261984 DE19722261984 DE 19722261984 DE 2261984 A DE2261984 A DE 2261984A DE 2261984 A1 DE2261984 A1 DE 2261984A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- methyl
- compound
- compounds
- same meaning
- 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
- 238000004519 manufacturing process Methods 0.000 title description 10
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical class F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 25
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 17
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 239000011630 iodine Substances 0.000 claims description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- FWQHNLCNFPYBCA-UHFFFAOYSA-N fluoran Chemical class C12=CC=CC=C2OC2=CC=CC=C2C11OC(=O)C2=CC=CC=C21 FWQHNLCNFPYBCA-UHFFFAOYSA-N 0.000 claims description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000000921 elemental analysis Methods 0.000 description 11
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- CYMPUOGZUXAIMY-UHFFFAOYSA-N 4-methoxy-2-methyl-n-phenylaniline Chemical compound CC1=CC(OC)=CC=C1NC1=CC=CC=C1 CYMPUOGZUXAIMY-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 235000011181 potassium carbonates Nutrition 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- YGLYYWZISFBCPU-UHFFFAOYSA-N 4-ethoxy-2-methyl-n-phenylaniline Chemical compound CC1=CC(OCC)=CC=C1NC1=CC=CC=C1 YGLYYWZISFBCPU-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- FGTYTUFKXYPTML-UHFFFAOYSA-N 2-benzoylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 FGTYTUFKXYPTML-UHFFFAOYSA-N 0.000 description 4
- 125000003047 N-acetyl group Chemical group 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- AYRUKGQCGNNMLA-UHFFFAOYSA-N n-(4-methoxy-2-methylphenyl)acetamide Chemical compound COC1=CC=C(NC(C)=O)C(C)=C1 AYRUKGQCGNNMLA-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- XVAIDCNLVLTVFM-UHFFFAOYSA-N methyl ether of paracetamol Natural products COC1=CC=C(NC(C)=O)C=C1 XVAIDCNLVLTVFM-UHFFFAOYSA-N 0.000 description 3
- 238000001256 steam distillation Methods 0.000 description 3
- YSFLQVNTBBUKEA-UHFFFAOYSA-N 1-bromo-2,4-dimethylbenzene Chemical group CC1=CC=C(Br)C(C)=C1 YSFLQVNTBBUKEA-UHFFFAOYSA-N 0.000 description 2
- WQFYAGVHZYFXDO-UHFFFAOYSA-N 2'-anilino-6'-(diethylamino)-3'-methylspiro[2-benzofuran-3,9'-xanthene]-1-one Chemical compound C=1C(N(CC)CC)=CC=C(C2(C3=CC=CC=C3C(=O)O2)C2=C3)C=1OC2=CC(C)=C3NC1=CC=CC=C1 WQFYAGVHZYFXDO-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- -1 o-carboxyanilino Chemical group 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- LMFRTSBQRLSJHC-UHFFFAOYSA-N 1-bromo-3,5-dimethylbenzene Chemical compound CC1=CC(C)=CC(Br)=C1 LMFRTSBQRLSJHC-UHFFFAOYSA-N 0.000 description 1
- ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 1
- PXWYZLWEKCMTEZ-UHFFFAOYSA-N 1-ethyl-2-nitrobenzene Chemical compound CCC1=CC=CC=C1[N+]([O-])=O PXWYZLWEKCMTEZ-UHFFFAOYSA-N 0.000 description 1
- QXISTPDUYKNPLU-UHFFFAOYSA-N 2-bromo-1,4-dimethylbenzene Chemical group CC1=CC=C(C)C(Br)=C1 QXISTPDUYKNPLU-UHFFFAOYSA-N 0.000 description 1
- XRXMNWGCKISMOH-UHFFFAOYSA-N 2-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Br XRXMNWGCKISMOH-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 102000006835 Lamins Human genes 0.000 description 1
- 108010047294 Lamins Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 210000005053 lamin Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/132—Chemical colour-forming components; Additives or binders therefor
- B41M5/136—Organic colour formers, e.g. leuco dyes
- B41M5/145—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
- B41M5/1455—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring characterised by fluoran compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
- B41M5/323—Organic colour formers, e.g. leuco dyes
- B41M5/327—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
- B41M5/3275—Fluoran compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP46071495A JPS525489B2 (enrdf_load_stackoverflow) | 1971-09-14 | 1971-09-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2261984A1 true DE2261984A1 (de) | 1973-05-24 |
Family
ID=13462288
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722261984 Pending DE2261984A1 (de) | 1971-09-14 | 1972-09-13 | Verfahren zur herstellung von fluoranverbindungen |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS525489B2 (enrdf_load_stackoverflow) |
| AT (1) | AT316510B (enrdf_load_stackoverflow) |
| BE (1) | BE788431A (enrdf_load_stackoverflow) |
| CH (1) | CH569698A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2261984A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2153979A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1409311A (enrdf_load_stackoverflow) |
| IT (1) | IT974636B (enrdf_load_stackoverflow) |
| ZA (1) | ZA726209B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3407369A1 (de) * | 1982-12-27 | 1985-08-29 | Shin Nisso Kako Co., Ltd., Tokio/Tokyo | Chromogenes aufzeichnungsmaterial |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54119294U (enrdf_load_stackoverflow) * | 1978-02-10 | 1979-08-21 | ||
| JPS57193435A (en) * | 1981-05-21 | 1982-11-27 | Nippon Kayaku Co Ltd | Production of diphenylamine |
| JPS6040165A (ja) * | 1983-08-12 | 1985-03-02 | Sumitomo Chem Co Ltd | フルオラン化合物の製造方法 |
| JPS6040164A (ja) * | 1983-08-12 | 1985-03-02 | Sumitomo Chem Co Ltd | フルオラン化合物の製造法 |
| CH654839A5 (de) * | 1983-09-26 | 1986-03-14 | Ciba Geigy Ag | Verfahren zur herstellung von basisch substituierten fluoranverbindungen. |
| CN103086898B (zh) * | 2012-07-11 | 2015-04-08 | 山东道可化学有限公司 | 二苯胺或其环上取代的衍生物的制备方法 |
| CN104058978A (zh) * | 2014-06-04 | 2014-09-24 | 安徽佑骏商品混凝土有限公司 | 一种3-甲氧基二苯胺合成工艺 |
| CN104628585B (zh) * | 2015-02-13 | 2016-08-24 | 山东道可化学有限公司 | 一种二苯胺或其环上取代的衍生物的制备方法 |
-
0
- BE BE788431D patent/BE788431A/xx not_active IP Right Cessation
-
1971
- 1971-09-14 JP JP46071495A patent/JPS525489B2/ja not_active Expired
-
1972
- 1972-09-05 GB GB4105872A patent/GB1409311A/en not_active Expired
- 1972-09-12 ZA ZA726209A patent/ZA726209B/xx unknown
- 1972-09-12 IT IT29085/72A patent/IT974636B/it active
- 1972-09-13 DE DE19722261984 patent/DE2261984A1/de active Pending
- 1972-09-13 FR FR7232359A patent/FR2153979A5/fr not_active Expired
- 1972-09-14 AT AT788072A patent/AT316510B/de not_active IP Right Cessation
- 1972-09-14 CH CH1348372A patent/CH569698A5/xx not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3407369A1 (de) * | 1982-12-27 | 1985-08-29 | Shin Nisso Kako Co., Ltd., Tokio/Tokyo | Chromogenes aufzeichnungsmaterial |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4836132A (enrdf_load_stackoverflow) | 1973-05-28 |
| GB1409311A (en) | 1975-10-08 |
| AU4590772A (en) | 1973-06-14 |
| ZA726209B (en) | 1973-06-27 |
| JPS525489B2 (enrdf_load_stackoverflow) | 1977-02-14 |
| DE2244873B2 (de) | 1976-02-19 |
| DE2244873A1 (de) | 1973-03-22 |
| CH569698A5 (enrdf_load_stackoverflow) | 1975-11-28 |
| IT974636B (it) | 1974-07-10 |
| FR2153979A5 (enrdf_load_stackoverflow) | 1973-05-04 |
| BE788431A (fr) | 1973-01-02 |
| AT316510B (de) | 1974-07-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |