CN104276928A - Preparation method of 4,6-bi[1-(4-hydroxypheny)-1-methyl ethyl]-1,3-hydroquinone - Google Patents
Preparation method of 4,6-bi[1-(4-hydroxypheny)-1-methyl ethyl]-1,3-hydroquinone Download PDFInfo
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- CN104276928A CN104276928A CN201410522458.3A CN201410522458A CN104276928A CN 104276928 A CN104276928 A CN 104276928A CN 201410522458 A CN201410522458 A CN 201410522458A CN 104276928 A CN104276928 A CN 104276928A
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- isopropenyl phenol
- mass ratio
- resorcinol
- preparation
- primary catalysts
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- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 239000003054 catalyst Substances 0.000 claims abstract description 47
- WUQYBSRMWWRFQH-UHFFFAOYSA-N 2-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC=C1O WUQYBSRMWWRFQH-UHFFFAOYSA-N 0.000 claims abstract description 31
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000000047 product Substances 0.000 claims abstract description 23
- 239000002131 composite material Substances 0.000 claims abstract description 21
- 239000000706 filtrate Substances 0.000 claims abstract description 14
- 238000002156 mixing Methods 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 238000001704 evaporation Methods 0.000 claims abstract description 9
- 230000008020 evaporation Effects 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 18
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 18
- 238000002425 crystallisation Methods 0.000 claims description 12
- 230000008025 crystallization Effects 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 9
- 229960003280 cupric chloride Drugs 0.000 claims description 9
- 229910052742 iron Inorganic materials 0.000 claims description 9
- 230000001476 alcoholic effect Effects 0.000 claims description 7
- 238000010792 warming Methods 0.000 claims description 7
- VRFOVKLVWVGQCM-UHFFFAOYSA-N 2-[2-(4-hydroxyphenyl)propan-2-yl]benzene-1,3-diol Chemical compound OC=1C=CC=C(O)C=1C(C)(C)C1=CC=C(O)C=C1 VRFOVKLVWVGQCM-UHFFFAOYSA-N 0.000 claims description 6
- 239000004793 Polystyrene Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 229920002223 polystyrene Polymers 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 9
- 239000003513 alkali Substances 0.000 abstract description 5
- 238000000034 method Methods 0.000 abstract description 4
- 238000006386 neutralization reaction Methods 0.000 abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 abstract description 2
- 239000012043 crude product Substances 0.000 abstract 2
- 238000001914 filtration Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- -1 photostabilizer Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 150000005205 dihydroxybenzenes Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
- B01J31/30—Halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/84—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by crystallisation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/005—General concepts, e.g. reviews, relating to methods of using catalyst systems, the concept being defined by a common method or theory, e.g. microwave heating or multiple stereoselectivity
Abstract
The invention relates to a preparation method of 4,6-bi[1-(4-hydroxypheny)-1-methyl ethyl]-1,3-hydroquinone. The method sequentially comprises the following steps: (a) sequentially feeding isopropenyl phenol, resorcinol, and a composite catalyst to a reaction container, evenly mixing, reacting at 30-50 DEG C for 5-8 hours, heating up to 50-70 DEG C and filtering when the mixture is hot, so as to obtain filtrate and filter residues; (b) evaporating the filtrate at 75-90 DEG C and 200-700MPa to remove isopropenyl phenol, so as to obtain a crude product; and (c) dissolving the crude product into an alcohol solvent to crystallize, wherein the mass ratio of the isopropenyl phenol to the resorcinol to the composite catalyst is (20-25) to (8-10) to 1. On one hand, the isopropenyl phenol and the resorcinol are catalyzed by using the composite catalyst, neutralization by using an alkali liquor is omitted after reaction, and the catalyst can be repeatedly utilized, so that the cost is saved; and on the other hand, the isopropenyl phenol is removed by direct evaporation, and the product is refined and does not need to be washed by water, so that the pollution to the environment is reduced.
Description
Technical field
The invention belongs to organic synthesis field, be specifically related to the preparation method of two [1-(4-hydroxy phenyl)-1-the methylethyl]-Resorcinol of a kind of 4,6-.
Background technology
The chemical structural formula of two [1-(4-hydroxy phenyl)-1-the methylethyl]-Resorcinol of 4,6-is
, be very important organic chemistry raw material, they are as macromolecular material intermediate, are applied in the fields such as synthetic epoxy resin, cyanate, polycarbonate, polyarylester and resol widely; As oxidation inhibitor, photostabilizer, softening agent, thermo-stabilizer, fire retardant and being applied in widely in the field such as manufacture and high-performance coating of CD.Research and develop novel bisphenol compound the manufacture of novel material, application and development are had very important significance.The synthetic method of current this dihydroxy-benzene is in nitrogen or in the air by Resorcinol, catalyst mix evenly, is warming up to temperature of reaction dropping and reacts for some time to isopropenyl phenol, react the alkali adding metered amount after terminating and carry out neutralization reaction; After product distillation, recrystallization will be washed.Although the method is simple, easy handling, not only needs in this process again to use alkali to carry out neutralization reaction, add cost; And need, with the cleaning of a large amount of water, to cause sewage more, be unfavorable for environment protection.
Summary of the invention
The present invention seeks to the preparation method in order to overcome 4,6-two [1-(4-hydroxy phenyl)-1-methylethyl]-Resorcinols that the deficiencies in the prior art provide a kind of environmental protection.
For achieving the above object, the technical solution used in the present invention is: the preparation method of two [1-(4-hydroxy phenyl)-1-the methylethyl]-Resorcinol of a kind of 4,6-, comprises the following steps successively:
A () drops into successively isopropenyl phenol, Resorcinol, composite catalyst in reaction vessel, react 5 ~ 8 hours, be then warming up to 50 ~ 70 DEG C of filtered while hot, obtain filtrate and filter residue after mixing at 30 ~ 50 DEG C;
B described filtrate is placed in 200 ~ 700Pa, 75 ~ 90 DEG C of conditions by () under, evaporation removing obtains thick product to isopropenyl phenol;
C described thick product is dissolved in alcoholic solvent and carries out crystallization by ();
The described mass ratio to isopropenyl phenol, Resorcinol and composite catalyst is 20 ~ 25:8 ~ 10:1.
Optimally, it also comprises step (d) step (c) products therefrom is carried out repeatedly crystallization after mixing in 1:2 ~ 4 in mass ratio with alcoholic solvent.
Optimally, in step (a), described filter residue is recycled; In step (b), described isopropenyl phenol to be recycled.
Optimally, described composite catalyst is composited by Primary Catalysts and secondary catalyzer, the mass ratio of described Primary Catalysts and secondary catalyzer is 1:1, and described Primary Catalysts comprises iron(ic) chloride, cupric chloride and alchlor, and described secondary catalyzer is macroporous type polystyrene strong acid positive resin.
Further, the mass ratio that described iron(ic) chloride accounts for described Primary Catalysts is 15 ~ 25%, and the mass ratio that described cupric chloride accounts for described Primary Catalysts is 25 ~ 35%, and the mass ratio that described alchlor accounts for described Primary Catalysts is 45 ~ 60%.
Because technique scheme is used, the present invention compared with prior art has following advantages: the present invention 4, two [1-(4-the hydroxy phenyl)-1-methylethyl]-1 of 6-, the preparation method of 3-dihydroxy-benzene, composite catalyst is used to carry out catalysis to isopropenyl phenol and Resorcinol on the one hand, do not need after the reaction use alkali lye neutralization and catalyzer can reuse, saved cost; Directly isopropenyl phenol is carried out refining by evaporation removing on the other hand again, do not need to use water to rinse product, be conducive to reducing the pollution to environment.
Embodiment
Below will the present invention is described in detail by specific embodiment.
The preparation method of two [1-(4-hydroxy phenyl)-1-the methylethyl]-Resorcinol of the present invention 4,6-, comprises the following steps: comprise the following steps successively successively:
A () drops into successively isopropenyl phenol, Resorcinol, composite catalyst in reaction vessel, react 5 ~ 8 hours at 30 ~ 50 DEG C after mixing, then 50 ~ 70 DEG C of filtered while hot are warming up to, obtain filtrate and filter residue, wherein 20 ~ 25:8 ~ 10:1 is preferably to the mass ratio of isopropenyl phenol, Resorcinol and composite catalyst, and the twice of Resorcinol quality is exceeded to the quality of isopropenyl phenol; Filter residue be composite catalyst can recovery in reaction next time, composite catalyst is conducive to suppressing the carrying out of side reaction, improves productive rate;
B described filtrate is placed in 200 ~ 700Pa, 75 ~ 90 DEG C of conditions by () under, evaporation removing obtains thick product to isopropenyl phenol, and do not need to use alkali lye to neutralize, greatly save cost and reduced the pollution to environment, removing can use rotatory evaporator to carry out to the operation of isopropenyl phenol, can reclaim isopropenyl phenol like this and overlap and be used for reacting next time, cost-saving;
C described thick product is dissolved in alcoholic solvent and carries out crystallization by (), can also refine further this product, such as, the product of gained is carried out repeatedly crystallization after mixing in 1:2 ~ 4 with alcoholic solvent, in mass ratio to improve the purity of final product; Wherein alcoholic solvent is the lower boiling alcohols such as methyl alcohol, ethanol.
Composite catalyst is composited by Primary Catalysts and secondary catalyzer, the mass ratio of described Primary Catalysts and secondary catalyzer is 1:1, described Primary Catalysts comprises iron(ic) chloride, cupric chloride and alchlor, described secondary catalyzer is macroporous type polystyrene strong acid positive resin, the mass ratio that wherein said iron(ic) chloride accounts for described Primary Catalysts is 15 ~ 25%, the mass ratio that described cupric chloride accounts for described Primary Catalysts is 25 ~ 35%, the mass ratio that described alchlor accounts for described Primary Catalysts is 45 ~ 60%, is conducive to suppressing side reaction thus the productive rate improving product.
Embodiment 1
This city embodiment provides a kind of 4,6-preparation method of two [1-(4-hydroxy phenyl)-1-methylethyl]-Resorcinol, comprises the following steps successively:
A () drops into 1200kg successively to isopropenyl phenol, 450kg Resorcinol, 50kg composite catalyst in reaction vessel, react 8 hours at 30 DEG C after mixing, then be warming up to 60 DEG C of filtered while hot, obtain filtrate and filter residue, wherein filter residue is recycled;
B described filtrate is placed in 200Pa, 75 DEG C of conditions by () under, evaporation removing obtains thick product to isopropenyl phenol, wherein recycles isopropenyl phenol;
C described thick product is dissolved in methyl alcohol and carries out crystallization by ();
(d) by step (c) products therefrom and methyl alcohol in mass ratio 1:3 carry out twice crystallization after mixing;
Wherein, 50kg composite catalyst is composited by 25kg Primary Catalysts and the secondary catalyzer of 25kg, and 25kg Primary Catalysts comprises 6.25kg iron(ic) chloride, 8.75kg cupric chloride and 10kg alchlor, and secondary catalyzer is macroporous type polystyrene strong acid positive resin.
Embodiment 2
This city embodiment provides a kind of 4,6-preparation method of two [1-(4-hydroxy phenyl)-1-methylethyl]-Resorcinol, comprises the following steps successively:
A () drops into 1000kg successively to isopropenyl phenol, 400kg Resorcinol, 50kg composite catalyst in reaction vessel, react 5 hours at 50 DEG C after mixing, then be warming up to 50 DEG C of filtered while hot, obtain filtrate and filter residue, wherein filter residue is recycled;
B described filtrate is placed in 500Pa, 80 DEG C of conditions by () under, evaporation removing obtains thick product to isopropenyl phenol, wherein recycles isopropenyl phenol;
C described thick product is dissolved in ethanol and carries out crystallization by ();
(d) by step (c) products therefrom and ethanol in mass ratio 1:2 carry out three crystallizations after mixing;
Wherein, 50kg composite catalyst is composited by 25kg Primary Catalysts and the secondary catalyzer of 25kg, and 25kg Primary Catalysts comprises 3.75kg iron(ic) chloride, 6.25kg cupric chloride and 15kg alchlor, and secondary catalyzer is macroporous type polystyrene strong acid positive resin.
Embodiment 3
This city embodiment provides a kind of 4,6-preparation method of two [1-(4-hydroxy phenyl)-1-methylethyl]-Resorcinol, comprises the following steps successively:
A () drops into 1250kg successively to isopropenyl phenol, 500kg Resorcinol, 50kg composite catalyst in reaction vessel, react 6 hours at 45 DEG C after mixing, then be warming up to 70 DEG C of filtered while hot, obtain filtrate and filter residue, wherein filter residue recycles and reuses;
B described filtrate is placed in 700Pa, 90 DEG C of conditions by () under, evaporation removing obtains thick product to isopropenyl phenol, wherein recycles isopropenyl phenol;
C described thick product is dissolved in methyl alcohol and carries out crystallization by ();
(d) by step (c) products therefrom and ethanol in mass ratio 1:4 carry out five crystallizations after mixing;
Wherein, 50kg composite catalyst is composited by 25kg Primary Catalysts and the secondary catalyzer of 25kg, and 25kg Primary Catalysts comprises 5kg iron(ic) chloride, 7kg cupric chloride and 13kg alchlor, and secondary catalyzer is macroporous type polystyrene strong acid positive resin.
Above-described embodiment is only for illustrating technical conceive of the present invention and feature; its object is to person skilled in the art can be understood content of the present invention and implement according to this; can not limit the scope of the invention with this; all equivalences done according to spirit of the present invention change or modify, and all should be encompassed within protection scope of the present invention.
Claims (5)
1. the preparation method of two [1-(4-hydroxy phenyl)-1-methylethyl]-Resorcinol, is characterized in that, comprise the following steps successively:
A () drops into successively isopropenyl phenol, Resorcinol, composite catalyst in reaction vessel, react 5 ~ 8 hours, be then warming up to 50 ~ 70 DEG C of filtered while hot, obtain filtrate and filter residue after mixing at 30 ~ 50 DEG C;
B described filtrate is placed in 200 ~ 700Pa, 75 ~ 90 DEG C of conditions by () under, evaporation removing obtains thick product to isopropenyl phenol;
C described thick product is dissolved in alcoholic solvent and carries out crystallization by ();
The described mass ratio to isopropenyl phenol, Resorcinol and composite catalyst is 20 ~ 25:8 ~ 10:1.
2. according to claim 14, two [1-(4-the hydroxy phenyl)-1-methylethyl]-1 of 6-, the preparation method of 3-dihydroxy-benzene, is characterized in that: it also comprises step (d) and step (c) products therefrom is carried out repeatedly crystallization after mixing in 1:2 ~ 4 in mass ratio with alcoholic solvent.
3. the preparation method of according to claim 14,6-two [1-(4-hydroxy phenyl)-1-methylethyl]-Resorcinols, it is characterized in that: in step (a), described filter residue is recycled; In step (b), described isopropenyl phenol to be recycled.
4. according to claim 14, two [1-(4-the hydroxy phenyl)-1-methylethyl]-1 of 6-, the preparation method of 3-dihydroxy-benzene, it is characterized in that: described composite catalyst is composited by Primary Catalysts and secondary catalyzer, the mass ratio of described Primary Catalysts and secondary catalyzer is 1:1, described Primary Catalysts comprises iron(ic) chloride, cupric chloride and alchlor, and described secondary catalyzer is macroporous type polystyrene strong acid positive resin.
5. according to claim 44, two [1-(4-the hydroxy phenyl)-1-methylethyl]-1 of 6-, the preparation method of 3-dihydroxy-benzene, it is characterized in that: the mass ratio that described iron(ic) chloride accounts for described Primary Catalysts is 15 ~ 25%, the mass ratio that described cupric chloride accounts for described Primary Catalysts is 25 ~ 35%, and the mass ratio that described alchlor accounts for described Primary Catalysts is 45 ~ 60%.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410522458.3A CN104276928B (en) | 2014-10-08 | 2014-10-08 | The preparation method of two [1-(4-hydroxy phenyl)-1-the methylethyl]-Resorcinol of a kind of 4,6- |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410522458.3A CN104276928B (en) | 2014-10-08 | 2014-10-08 | The preparation method of two [1-(4-hydroxy phenyl)-1-the methylethyl]-Resorcinol of a kind of 4,6- |
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| CN104276928A true CN104276928A (en) | 2015-01-14 |
| CN104276928B CN104276928B (en) | 2016-04-13 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113307725A (en) * | 2021-05-19 | 2021-08-27 | 辽宁靖帆新材料有限公司 | Preparation method of 4, 6-bis [1- (4-hydroxyphenyl) -1-methylethyl ] -1, 3-benzenediol |
| CN113480439A (en) * | 2021-07-21 | 2021-10-08 | 江西同宇新材料有限公司 | Preparation method of aminophenol containing isopropylidene alkane structure |
| CN113620786A (en) * | 2021-05-19 | 2021-11-09 | 辽宁靖帆新材料有限公司 | Method for synthesizing polyhydroxy phenolic compound by acid method |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06116191A (en) * | 1992-10-08 | 1994-04-26 | Mitsui Toatsu Chem Inc | Production of 1,3-dihydroxy-4,6-bis(alpha-methyl-alpha-@(3754/24)4'-hydroxyphenyl)ethyl)benzene |
| JPH0825935B2 (en) * | 1990-10-08 | 1996-03-13 | 三井東圧化学株式会社 | 1,3-Dihydroxy-4,6-bis [α-methyl-α- (4'-hydroxyphenyl) ethyl] benzene and method for producing the same |
| US5744653A (en) * | 1994-02-25 | 1998-04-28 | Mitsui Toatsu Chemicals, Inc. | Method for preparing 1,3-dihydroxy-4,6-bis(α-methyl-α(4'-hydroxyphenyl)ethyl)benzene |
| JP2003098664A (en) * | 2001-09-21 | 2003-04-04 | Mitsui Chemicals Inc | Resin composition, phenolic compound used in the same and method for producing the same |
| CN102875754A (en) * | 2012-09-28 | 2013-01-16 | 北京彤程创展科技有限公司 | Modified resorcinol phenolic resin and preparation method thereof and rubber compound |
-
2014
- 2014-10-08 CN CN201410522458.3A patent/CN104276928B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0825935B2 (en) * | 1990-10-08 | 1996-03-13 | 三井東圧化学株式会社 | 1,3-Dihydroxy-4,6-bis [α-methyl-α- (4'-hydroxyphenyl) ethyl] benzene and method for producing the same |
| JPH06116191A (en) * | 1992-10-08 | 1994-04-26 | Mitsui Toatsu Chem Inc | Production of 1,3-dihydroxy-4,6-bis(alpha-methyl-alpha-@(3754/24)4'-hydroxyphenyl)ethyl)benzene |
| US5744653A (en) * | 1994-02-25 | 1998-04-28 | Mitsui Toatsu Chemicals, Inc. | Method for preparing 1,3-dihydroxy-4,6-bis(α-methyl-α(4'-hydroxyphenyl)ethyl)benzene |
| JP2003098664A (en) * | 2001-09-21 | 2003-04-04 | Mitsui Chemicals Inc | Resin composition, phenolic compound used in the same and method for producing the same |
| CN102875754A (en) * | 2012-09-28 | 2013-01-16 | 北京彤程创展科技有限公司 | Modified resorcinol phenolic resin and preparation method thereof and rubber compound |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113307725A (en) * | 2021-05-19 | 2021-08-27 | 辽宁靖帆新材料有限公司 | Preparation method of 4, 6-bis [1- (4-hydroxyphenyl) -1-methylethyl ] -1, 3-benzenediol |
| CN113620786A (en) * | 2021-05-19 | 2021-11-09 | 辽宁靖帆新材料有限公司 | Method for synthesizing polyhydroxy phenolic compound by acid method |
| CN113480439A (en) * | 2021-07-21 | 2021-10-08 | 江西同宇新材料有限公司 | Preparation method of aminophenol containing isopropylidene alkane structure |
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| Publication number | Publication date |
|---|---|
| CN104276928B (en) | 2016-04-13 |
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