CN104326894A - Preparation method of 1, 4-dihydroxy-phenyl ketone - Google Patents
Preparation method of 1, 4-dihydroxy-phenyl ketone Download PDFInfo
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- CN104326894A CN104326894A CN201410681230.9A CN201410681230A CN104326894A CN 104326894 A CN104326894 A CN 104326894A CN 201410681230 A CN201410681230 A CN 201410681230A CN 104326894 A CN104326894 A CN 104326894A
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- Prior art keywords
- phenyl ketone
- dihydroxyl
- preparation
- nitrae
- isosorbide
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- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- SQBSRWJVBVTJDF-UHFFFAOYSA-N bis(1,4-dihydroxycyclohexa-2,4-dien-1-yl)methanone Chemical compound OC1(CC=C(C=C1)O)C(=O)C1(CC=C(C=C1)O)O SQBSRWJVBVTJDF-UHFFFAOYSA-N 0.000 title abstract 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims abstract description 41
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims abstract description 40
- 239000011592 zinc chloride Substances 0.000 claims abstract description 20
- 235000005074 zinc chloride Nutrition 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 14
- 150000004671 saturated fatty acids Chemical class 0.000 claims abstract description 11
- 238000005917 acylation reaction Methods 0.000 claims abstract description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 8
- 239000013078 crystal Substances 0.000 claims description 8
- 238000010828 elution Methods 0.000 claims description 7
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 235000003441 saturated fatty acids Nutrition 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 239000012074 organic phase Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 11
- 239000006227 byproduct Substances 0.000 abstract description 5
- 239000003054 catalyst Substances 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- 230000009466 transformation Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- -1 alkyl ketone Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000007516 brønsted-lowry acids Chemical class 0.000 description 1
- 150000007528 brønsted-lowry bases Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000002196 fatty nitriles Chemical class 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000002087 whitening effect Effects 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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- 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
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- 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
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a preparation method of 1, 4-dihydroxy-phenyl ketone. In an organic medium, anhydrous zinc chloride is taken as a catalyst, and resorcinol and saturated fatty acid are subjected to acylation reaction at the temperature of 80-140 DEG C to prepare a target product, namely 1, 4-dihydroxy-phenyl ketone. The preparation method of 1, 4-dihydroxy-phenyl ketone provided by the invention is simple in process flow, few in byproducts and high in yield, the catalyst is easy to recycle, and the preparation method is suitable for industrial production.
Description
Technical field
The present invention relates to technical field of organic synthesis, particularly, the present invention relates to a kind of preparation method of Isosorbide-5-Nitrae-dihydroxyl-phenyl ketone.
Background technology
Isosorbide-5-Nitrae-dihydroxyl-phenyl ketone is important medication chemistry, the daily use chemicals intermediate of a class, and its purposes is very extensive, and its structure is shown below, and the R in formula is CnH2n+1, n:1,2,3 ...Isosorbide-5-Nitrae-dihydroxyl-phenyl ketone can as the intermediate preparing cosmetics preservative, cosmetic active substances intermediate, and its derived product can as whitening agent, have anti-ageing, brighten, the effect such as antibacterial.
At present, about the document of Isosorbide-5-Nitrae-dihydroxyl-phenyl ketone synthetic method is less, the method being applicable to producing is then less.
1; the synthesis of 4-dihydroxyl-phenyl ketone is generally obtained through F-K reaction (F-C reaction) by Resorcinol; by Resorcinol, lipid acid (or its acyl chlorides or ester) acylations under the catalysis of Lewis acid, conventional Lewis acid catalyst has zinc chloride, tin tetrachloride, titanium tetrachloride, aluminum chloride etc.
The twenties in last century, J.Am.Chem.Soc., 1921,43 (2), preparation 1 when being catalyzer, solvent-free participation that the documents such as 348-360, U.S. US1649672, Canadian Patent CA272351 report respectively with Zinc Chloride Anhydrous, the method of 4-dihydroxyl-phenyl ketone, but all easily cause a large amount of by product or a large amount of unreacted phenomenon of raw material Resorcinol.Nineteen twenty-six, the method for J.Am.Chem.Soc., 48,2206-12 report take Zinc Chloride Anhydrous as catalyzer, fatty-acid ethyl ester prepares Isosorbide-5-Nitrae-dihydroxyl-phenyl ketone for acylting agent, but the method raw material is unconverted in a large number, and transformation efficiency is only 60%.
In addition; also has report (Journal of the Chemical Society; Perkin Transactions 1:Organic and Bio-Organic Chemistry (1972-1999); (12); 2894-900) take fatty nitrile as acylting agent; under triflic acid catalyzes, prepare the method for alkyl ketone, its feedstock fat nitrile and catalyzer trifluoromethanesulfonic acid all somewhat expensive, be not economic production method.
As can be seen here, the method for producing Isosorbide-5-Nitrae-dihydroxyl-phenyl ketone is not at present very desirable, or by product is many, or feed stock conversion is low, or severe reaction conditions, operational requirement are high, and yield is low, high expensive.
Summary of the invention
For the problems referred to above that Isosorbide-5-Nitrae-dihydroxyl-phenyl ketone synthetic method exists, the object of the present invention is to provide a kind of operate simple and easy, transformation efficiency is high, the preparation method of the Isosorbide-5-Nitrae-dihydroxyl-phenyl ketone of efficient economy, and can realize catalyst recovery recycling.
Technical problem to be solved by this invention is achieved by the following technical programs:
A preparation method for Isosorbide-5-Nitrae-dihydroxyl-phenyl ketone, comprises the steps:
1) at toluene, in dimethylbenzene or cyclohexane medium, take Zinc Chloride Anhydrous as catalyzer, Resorcinol and saturated fatty acid carry out acylation reaction at 80-140 DEG C;
2), after the cooling of question response product, lower floor's zinc chloride is separated;
3) by after organic phase acid elution, with alkali dose;
4) aqueous phase extracted acidizing crystal, filters, washs, obtained target product thing Isosorbide-5-Nitrae-dihydroxyl-phenyl ketone;
Described saturated fatty acid preferably from C2 ~ C10 linear saturated fatty acids, more preferably C3 ~ C5 linear saturated fatty acids.
Described Resorcinol and the mol ratio of saturated fatty acid preferably 0.5 ~ 2.5:1.
F-C acylation reaction adopts acyl chlorides or acid anhydrides to be acylating agent usually, and carries out in aprotic polar solvent.The inventive method adopts saturated fatty acid to be acylating agent, under Zinc Chloride Anhydrous katalysis, carries out acylations in higher temperature of reaction, to improve reaction conversion ratio.Acylation reaction temperature controls to carry out between 80 ~ 140 DEG C, preferably 80 ~ 120 DEG C.It is too slow that temperature crosses low reaction, and transformation efficiency is on the low side; Temperature is too high, and by product increases, and is unfavorable for the purifies and separates of object.
Described toluene, the consumption of dimethylbenzene or hexanaphthene is 1-15 times of Resorcinol quality, and preferred 3-5 doubly.
Described Zinc Chloride Anhydrous consumption is 1 ~ 5 times of Resorcinol quality.
Step 2) the catalyzer zinc chloride that is separated can recycling, need not through special process, loss is few.
Step 3) in, usually adopt inorganic bronsted lowry acids and bases bronsted lowry conventional in industrial production to carry out washing and extracting.As in a particular embodiment, acid elution adopts 6M hydrochloric acid, the sodium hydroxide solution of extraction employing 10%.
Step 4) in, during acidizing crystal, pH value is adjusted to 3-5.
Obtained Isosorbide-5-Nitrae-dihydroxyl-phenyl ketone can also adopt the method for aqueous ethanolic solution recrystallization to purify.In described aqueous ethanolic solution, the massfraction of ethanol is 20-35%, preferred 25-35%.Compare with tetracol phenixin with benzene (US1649672, CA272351), the present invention uses aqueous ethanolic solution for crystallizing system, environmental friendliness and yield is higher.
The inventive method is passed through the existing improvement preparing Isosorbide-5-Nitrae-dihydroxyl-phenyl ketone technique, and achieve the Efficient Conversion of raw material, the efficient recovery of catalyzer and utilization, production process is environmentally friendly.The preparation method of Resorcinol alkyl ketone of the present invention, technological process is simple, and by product is few, and yield is high, and catalyzer is easy to be recycled, is a kind of method of applicable suitability for industrialized production.
Embodiment
Below in conjunction with embodiment, the present invention will be described in detail, and embodiment is only the preferred embodiment of the present invention, is not limitation of the invention.
Embodiment one
By the butanic acid of 9.9g, 21mL toluene, 10g Zinc Chloride Anhydrous adds in the flask of 50mL, immerse in 100 DEG C of preheated oil baths, be stirred to constant temperature, add the Resorcinol of 6.05g, stir 30min, be warming up to 110 DEG C, continue reaction 5h, be cooled to 0 ~ 5 DEG C, separate lower floor's zinc chloride (with butanic acid, a small amount of Resorcinol and product), toluene layer is through 6M salt acid elution 1 ~ 2 time, after the abundant extraction of sodium hydroxide (20mL*5) of 10%, aqueous phase extracted concentrated hydrochloric acid adjust ph about 3.0, separate out a large amount of solid, be cooled to 5 ~ 10 DEG C, suction filtration, washing, the aqueous ethanolic solution recrystallization of 37.5%, obtain yellow needle-like crystals 7.8g, product yield is 79% (in Resorcinol).
Embodiment two
By the n Propanoic acid of 10.45g, 32mL hexanaphthene, 6.05g Resorcinol, 10g Zinc Chloride Anhydrous adds in the flask of 100mL, immerse in preheated oil bath, backflow band water reaction 6h, be cooled to 0 ~ 5 DEG C, separate lower floor's zinc chloride (with n Propanoic acid, a small amount of Resorcinol and product), organic layer is through 6M salt acid elution 1 ~ 2 time, after the abundant extraction of sodium hydroxide (20mL*5) of 10%, aqueous phase extracted concentrated hydrochloric acid adjust ph about 3.0, separate out a large amount of solid, be cooled to 5 ~ 10 DEG C, suction filtration, washing, the aqueous ethanolic solution recrystallization of 35%, obtain yellow needle-like crystals 7.1g, product yield is 77%.
Embodiment three
By the n-caproic acid of 9.74g, 35mL dimethylbenzene, 10g Zinc Chloride Anhydrous adds in the flask of 100mL, immerse in 100 DEG C of preheated oil baths, be stirred to constant temperature, add the Resorcinol of 6.05g, stir 30min, be warming up to 120 DEG C, continue reaction 5.5h, be cooled to 0 ~ 5 DEG C, separate lower floor's zinc chloride (with n-caproic acid, a small amount of Resorcinol and product), dimethylbenzene layer is through 6M salt acid elution 1 ~ 2 time, the sodium hydroxide (20mL*5) of 10% fully extracts, aqueous phase extracted concentrated hydrochloric acid adjust ph about 3, separate out a large amount of solid, be cooled to 5 ~ 10 DEG C, suction filtration, washing, the aqueous ethanolic solution recrystallization of 39%, obtain yellow needle-like crystals 8.9g, product yield is 76%.
Embodiment four
By the butanic acid of 9.9g, 70mL dimethylbenzene, 10g Zinc Chloride Anhydrous adds in the flask of 250mL, immerse in 100 DEG C of preheated oil baths, be stirred to constant temperature, add the Resorcinol of 6.05g, stir 30min, be warming up to 140 DEG C, continue reaction 4.0h, be cooled to 0 ~ 5 DEG C, separate lower floor's zinc chloride, dimethylbenzene layer is through 6M salt acid elution 1 ~ 2 time, the sodium hydroxide of 10% fully extracts, aqueous phase extracted concentrated hydrochloric acid adjust ph about 4.0, separate out a large amount of solid, be cooled to 5 ~ 10 DEG C, suction filtration, washing, the aqueous ethanolic solution recrystallization of 50%, obtain yellow needle-like crystals 7.5g, product yield is 76%.
The above embodiment only have expressed embodiments of the present invention; it describes comparatively concrete and detailed; but therefore can not be interpreted as the restriction to the scope of the claims of the present invention; in every case the technical scheme adopting the form of equivalent replacement or equivalent transformation to obtain, all should drop within protection scope of the present invention.
Claims (8)
1. a preparation method for Isosorbide-5-Nitrae-dihydroxyl-phenyl ketone, comprises the steps:
Step (1): at toluene, in dimethylbenzene or cyclohexane medium, take Zinc Chloride Anhydrous as catalyzer, Resorcinol and saturated fatty acid carry out acylation reaction at 80-140 DEG C;
Step (2): after the cooling of question response product, separate lower floor's zinc chloride;
Step (3): after organic phase acid elution, with alkali dose;
Step (4): aqueous phase extracted acidizing crystal, filters, washs, obtained target product thing Isosorbide-5-Nitrae-dihydroxyl-phenyl ketone;
Described saturated fatty acid is selected from C2 ~ C10 linear saturated fatty acids.
2. the preparation method of Isosorbide-5-Nitrae-dihydroxyl-phenyl ketone according to claim 1, is characterized in that: described Resorcinol and the mol ratio of saturated fatty acid are (0.5 ~ 2.5): 1.
3. the preparation method of Isosorbide-5-Nitrae-dihydroxyl-phenyl ketone according to claim 1, is characterized in that: described acylation reaction temperature is 80 ~ 120 DEG C.
4. the preparation method of Isosorbide-5-Nitrae-dihydroxyl-phenyl ketone according to claim 1, is characterized in that: described toluene, and the consumption of dimethylbenzene or hexanaphthene is 1 ~ 15 times of Resorcinol quality.
5. the preparation method of Isosorbide-5-Nitrae-dihydroxyl-phenyl ketone according to claim 1, is characterized in that: described Zinc Chloride Anhydrous consumption is 0.5 ~ 3.5 times of Resorcinol quality.
6. the preparation method of Isosorbide-5-Nitrae-dihydroxyl-phenyl ketone according to claim 1, is characterized in that: step 4) in, during acidizing crystal, pH value is adjusted to 3-5.
7. the preparation method of Isosorbide-5-Nitrae-dihydroxyl-phenyl ketone according to claim 1, is characterized in that: described method also comprises obtained object aqueous ethanolic solution recrystallization.
8. the preparation method of Isosorbide-5-Nitrae-dihydroxyl-phenyl ketone according to claim 7, is characterized in that: in described aqueous ethanolic solution, the massfraction of ethanol is 20%-35%.
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| CN201410681230.9A CN104326894A (en) | 2014-11-24 | 2014-11-24 | Preparation method of 1, 4-dihydroxy-phenyl ketone |
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| CN201410681230.9A CN104326894A (en) | 2014-11-24 | 2014-11-24 | Preparation method of 1, 4-dihydroxy-phenyl ketone |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5621146A (en) * | 1994-12-07 | 1997-04-15 | Kuraray Co., Ltd. | Process for producing 2,4-dihydroxyacetophenone |
| CN103159608A (en) * | 2011-12-14 | 2013-06-19 | 南京华狮化工有限公司 | A method for preparing resorcinol alkyl ketones |
-
2014
- 2014-11-24 CN CN201410681230.9A patent/CN104326894A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5621146A (en) * | 1994-12-07 | 1997-04-15 | Kuraray Co., Ltd. | Process for producing 2,4-dihydroxyacetophenone |
| CN103159608A (en) * | 2011-12-14 | 2013-06-19 | 南京华狮化工有限公司 | A method for preparing resorcinol alkyl ketones |
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Application publication date: 20150204 |