JPH0825952B2 - ６−ヒドロキシ−２−ナフトンの製造法 - Google Patents
６−ヒドロキシ−２−ナフトンの製造法Info
- Publication number
- JPH0825952B2 JPH0825952B2 JP62126074A JP12607487A JPH0825952B2 JP H0825952 B2 JPH0825952 B2 JP H0825952B2 JP 62126074 A JP62126074 A JP 62126074A JP 12607487 A JP12607487 A JP 12607487A JP H0825952 B2 JPH0825952 B2 JP H0825952B2
- Authority
- JP
- Japan
- Prior art keywords
- hydroxy
- naphthyl
- naphthone
- ester
- reaction
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 25
- AXVULUJQJBQWEC-UHFFFAOYSA-N 6-hydroxy-1h-naphthalen-2-one Chemical compound C1C(=O)C=CC2=CC(O)=CC=C21 AXVULUJQJBQWEC-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 38
- -1 2-naphthyl carboxylate ester Chemical class 0.000 claims abstract description 26
- RJNPPEUAJCEUPV-UHFFFAOYSA-N naphthalen-2-yl acetate Chemical compound C1=CC=CC2=CC(OC(=O)C)=CC=C21 RJNPPEUAJCEUPV-UHFFFAOYSA-N 0.000 claims abstract description 24
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000654 additive Substances 0.000 claims abstract description 7
- 230000000996 additive effect Effects 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 6
- 125000004959 2,6-naphthylene group Chemical group [H]C1=C([H])C2=C([H])C([*:1])=C([H])C([H])=C2C([H])=C1[*:2] 0.000 claims description 4
- BEIIYTIDGSZGDA-UHFFFAOYSA-N 2-hydroxy-1-naphthalen-1-ylethanone Chemical class C1=CC=C2C(C(=O)CO)=CC=CC2=C1 BEIIYTIDGSZGDA-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 12
- 150000008064 anhydrides Chemical class 0.000 abstract description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 229950011260 betanaphthol Drugs 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 230000008707 rearrangement Effects 0.000 description 4
- 238000005618 Fries rearrangement reaction Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- VUMVUNBFPQHMII-UHFFFAOYSA-N 1-hydroxy-1h-naphthalen-2-one Chemical compound C1=CC=C2C(O)C(=O)C=CC2=C1 VUMVUNBFPQHMII-UHFFFAOYSA-N 0.000 description 2
- GEYCYCTZOOCRJL-UHFFFAOYSA-N 2-hydroxy-2h-naphthalen-1-one Chemical class C1=CC=C2C(=O)C(O)C=CC2=C1 GEYCYCTZOOCRJL-UHFFFAOYSA-N 0.000 description 2
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- BHJHPYFAYGAPLS-UHFFFAOYSA-N Guaicyl acetate Chemical compound COC1=CC=CC=C1OC(C)=O BHJHPYFAYGAPLS-UHFFFAOYSA-N 0.000 description 2
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- KVMXEPJRCAPKJL-UHFFFAOYSA-N naphthalen-2-yl propanoate Chemical compound C1=CC=CC2=CC(OC(=O)CC)=CC=C21 KVMXEPJRCAPKJL-UHFFFAOYSA-N 0.000 description 2
- 150000004780 naphthols Chemical class 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229940049953 phenylacetate Drugs 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- VUIOUIWZVKVFCI-UHFFFAOYSA-N 1-(2-hydroxynaphthalen-1-yl)ethanone Chemical compound C1=CC=C2C(C(=O)C)=C(O)C=CC2=C1 VUIOUIWZVKVFCI-UHFFFAOYSA-N 0.000 description 1
- OTXGVXYCMIJUGJ-UHFFFAOYSA-N 1-acetyloxynaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C(OC(=O)C)=C(C(O)=O)C=CC2=C1 OTXGVXYCMIJUGJ-UHFFFAOYSA-N 0.000 description 1
- HHEPNSXKXOXNQV-UHFFFAOYSA-N 1-naphthalen-1-ylbutan-1-one Chemical compound C1=CC=C2C(C(=O)CCC)=CC=CC2=C1 HHEPNSXKXOXNQV-UHFFFAOYSA-N 0.000 description 1
- GXXXUZIRGXYDFP-UHFFFAOYSA-M 2-(4-methylphenyl)acetate Chemical compound CC1=CC=C(CC([O-])=O)C=C1 GXXXUZIRGXYDFP-UHFFFAOYSA-M 0.000 description 1
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical compound OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 description 1
- KCWQXDQUKLJUEU-UHFFFAOYSA-N 2-naphthyl butyrate Chemical compound C1=CC=CC2=CC(OC(=O)CCC)=CC=C21 KCWQXDQUKLJUEU-UHFFFAOYSA-N 0.000 description 1
- RZPFVRFSYMUDJO-UHFFFAOYSA-N 2h-naphthalen-1-one Chemical class C1=CC=C2C(=O)CC=CC2=C1 RZPFVRFSYMUDJO-UHFFFAOYSA-N 0.000 description 1
- 229940073735 4-hydroxy acetophenone Drugs 0.000 description 1
- QSDSWPOSISCSSI-UHFFFAOYSA-N 7-chloronaphthalen-2-ol Chemical compound C1=CC(Cl)=CC2=CC(O)=CC=C21 QSDSWPOSISCSSI-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010027626 Milia Diseases 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000005354 acylalkyl group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- OTGAHJPFNKQGAE-UHFFFAOYSA-N cresatin Chemical compound CC(=O)OC1=CC=CC(C)=C1 OTGAHJPFNKQGAE-UHFFFAOYSA-N 0.000 description 1
- 229960000862 cresatin Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US870062 | 1986-06-03 | ||
| US06/870,062 US4675449A (en) | 1986-06-03 | 1986-06-03 | Process for producing 6-hydroxy-2-naphthones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62286948A JPS62286948A (ja) | 1987-12-12 |
| JPH0825952B2 true JPH0825952B2 (ja) | 1996-03-13 |
Family
ID=25354724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62126074A Expired - Lifetime JPH0825952B2 (ja) | 1986-06-03 | 1987-05-25 | ６−ヒドロキシ−２−ナフトンの製造法 |
Country Status (8)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5087769A (en) * | 1990-09-26 | 1992-02-11 | Hoechst Celanese Corporation | Preparation of 6-substituted-2-vinylnaphthalene |
| JP2009079024A (ja) * | 2007-09-27 | 2009-04-16 | Air Water Inc | ２−ナフトール誘導体の製造方法 |
| JP5157839B2 (ja) * | 2008-11-12 | 2013-03-06 | 三菱瓦斯化学株式会社 | 新規ナフトール化合物とその製造方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2763691A (en) * | 1952-08-21 | 1956-09-18 | Eastman Kodak Co | Process for production of 2,4,5-trihydroxyacetophenone |
| US2833825A (en) * | 1954-03-22 | 1958-05-06 | California Research Corp | Preparation of acylphenols |
| US3403183A (en) * | 1966-12-16 | 1968-09-24 | Koppers Co Inc | Production of benzophenones |
| DE2616986A1 (de) * | 1976-04-17 | 1977-10-27 | Bayer Ag | Verfahren zur herstellung von hydroxyketonen |
| GB8315610D0 (en) * | 1983-06-07 | 1983-07-13 | Ici Plc | Chemical process |
| GB8315612D0 (en) * | 1983-06-07 | 1983-07-13 | Ici Plc | Chemical process |
| US4607125A (en) * | 1985-04-08 | 1986-08-19 | Celanese Corporation | Process for producing hydroxy aromatic ketones |
| CA1257291A (en) * | 1984-10-17 | 1989-07-11 | Harold R. Gerberich | Process for producing aromatic diols and their ester and ether derivatives |
| US4593125A (en) * | 1985-03-13 | 1986-06-03 | Celanese Corporation | Acylation of naphthalenes |
-
1986
- 1986-06-03 US US06/870,062 patent/US4675449A/en not_active Expired - Lifetime
-
1987
- 1987-05-25 JP JP62126074A patent/JPH0825952B2/ja not_active Expired - Lifetime
- 1987-05-27 CA CA000538124A patent/CA1271780A/en not_active Expired - Fee Related
- 1987-06-02 DE DE8787304851T patent/DE3778821D1/de not_active Expired - Fee Related
- 1987-06-02 EP EP87304851A patent/EP0264168B1/en not_active Expired - Lifetime
- 1987-06-02 ES ES198787304851T patent/ES2032443T3/es not_active Expired - Lifetime
- 1987-06-02 AT AT87304851T patent/ATE75715T1/de not_active IP Right Cessation
-
1992
- 1992-05-07 GR GR910402233T patent/GR3004506T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE3778821D1 (de) | 1992-06-11 |
| ATE75715T1 (de) | 1992-05-15 |
| US4675449A (en) | 1987-06-23 |
| EP0264168A3 (en) | 1988-09-07 |
| CA1271780A (en) | 1990-07-17 |
| GR3004506T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-04-28 |
| ES2032443T3 (es) | 1993-02-16 |
| EP0264168B1 (en) | 1992-05-06 |
| EP0264168A2 (en) | 1988-04-20 |
| JPS62286948A (ja) | 1987-12-12 |
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