CN106554255A - A kind of preparation method of 2,6 orcin - Google Patents
A kind of preparation method of 2,6 orcin Download PDFInfo
- Publication number
- CN106554255A CN106554255A CN201610963261.2A CN201610963261A CN106554255A CN 106554255 A CN106554255 A CN 106554255A CN 201610963261 A CN201610963261 A CN 201610963261A CN 106554255 A CN106554255 A CN 106554255A
- Authority
- CN
- China
- Prior art keywords
- orcins
- reaction
- preparation
- solid acid
- methanol
- 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.)
- Granted
Links
- 0 C*c(cc(*C)c(O)c1)c1O Chemical compound C*c(cc(*C)c(O)c1)c1O 0.000 description 1
- VSGJHHIAMHUZKF-UHFFFAOYSA-N CC(C(CCC1)=O)C1=O Chemical compound CC(C(CCC1)=O)C1=O VSGJHHIAMHUZKF-UHFFFAOYSA-N 0.000 description 1
- ZTMADXFOCUXMJE-UHFFFAOYSA-N Cc(c(O)ccc1)c1O Chemical compound Cc(c(O)ccc1)c1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 1
- HJSLFCCWAKVHIW-UHFFFAOYSA-N O=C(CCC1)CC1=O Chemical compound O=C(CCC1)CC1=O HJSLFCCWAKVHIW-UHFFFAOYSA-N 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
- C07C37/16—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 condensation involving hydroxy groups of phenols or alcohols or the ether or mineral ester group derived therefrom
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of preparation method of 2,6 orcins, comprises the steps：(1) methylation reaction：With resorcinol as raw material in fixed-bed reactor, with solid acid as catalyst, with a certain amount of methanol as solvent and methylating reagent, methylation reaction is carried out at a certain temperature；(2) distill：By reactant liquor vacuum distillation recovered solvent, the crude product of 2,6 orcins is obtained；(3) purification：The crude product of 2,6 orcins obtains 2,6 orcin highly finished product through recrystallization process.The present invention reduces environmental pollution, reduces cost, simple to operate while improve product quality quality, cleans production, environmental protection, is more suitable for producing in enormous quantities.
Description
Technical field
The invention belongs to technical field of chemical material preparation, concretely relates to the preparation of one kind 2,6- orcins
Method.
Background technology
2,6- orcins have many important physicochemical properties, and which has very important answering in chemical field
With, it is indispensable industrial chemicals, which is applied to synthetic resin, dyeing, pigment, dyestuff, hair dyess, medicine, pesticide, agriculture
With multiple fields such as chemicals, sensitive material and explosives, and as which has good disinfecting and sterilizing functions, in the last few years
By substantial amounts of use in the products such as shampoo, skin care item.
Eighties of last century the eighties, people begin to research 2, and the synthetic method of 6- orcins is up to the present literary
The synthetic method for having reported several 2,6- orcins is offered, predominantly：
1st, with 1,3-propanedicarboxylic acid as initiation material, under the catalysis of Nitrobenzol and aluminum chloride, react with chloroacetic chloride and generate 2-
Be hydrolyzed after methyl isophthalic acid, hydroresorcinol, 2- methyl isophthalic acids, hydroresorcinol and acetic anhydride reaction i.e. synthesising target compound 2 again,
6- orcins, its synthetic route is：
The route is more complicated, needs three-step reaction synthesize target product, and the selectivity of reaction is poor, can produce compared with
Many by-products, are not easy to the separating-purifying of product, and the post processing of reaction is relative complex.The three wastes that reaction is produced also are difficult to locate
Reason, the pollution to environment are more serious.
2nd, with 1, hydroresorcinol is raw material, by CH3I or Mannich reactions introduce methyl in 2- positions and are carrying out dehydrogenation
Synthesize 2,6- orcins, its synthetic route is：
The route will be hydrogenated with and dehydrogenation reaction in building-up process, and the two processes are required to urge using substantial amounts of Pd/C
Agent, and reaction yield is low, product cost is higher.
3rd, hydrogenation reaction is carried out, then in acetate system under high-temperature and high-pressure conditions for raw material with 2,6- dinitrotoluene (DNT)s
Under, catalyst is made with Pd/C, hydrolysis under high-temperature and high-pressure conditions obtains 2,6- orcins, and its synthetic route is：
The route is carried out under acid and high-temperature and high-pressure conditions, and the requirement to equipment is high, the price of the catalyst of employing
It is expensive so that the production cost of product rises, while the purity of the product for preparing is relatively low, be not suitable for industrialized production.
4th, the preparation method with resorcinol as raw material, up to the present, with resorcinol as Material synthesis 2,6- dihydroxies
Base toluene has been subjected to three development：
(1) resorcinol methanol methylation method
, in the presence of ammonium chloride, Jing High Temperature High Pressure direct reaction obtains product for the method resorcinol and methanol.Reaction
Carry out under high temperature, condition of high voltage, especially up to 530 DEG C of reaction temperature, increased difficulty to the type selecting of equipment, and react
Yield is low, and reaction selectivity is poor, and the by-product of production is more, and product is difficult to separate, and is not suitable for the needs of industrialized production.
(2) resorcinol iodomethane methylation method
The method first introduces the tert-butyl group in 4, the 6- positions of resorcinol, then first occurs in the 2- positions of resorcinol with iodomethane
Glycosylation reaction, finally sloughs the tert-butyl group again and obtains product 2,6- orcins.Use in changing the current commercial production of method,
The three-step reaction step of the route belongs to classical reaction, and the yield for often walking product is also higher, but the valency of catalyst iodine methane
Lattice are expensive, and this causes the cost of product to raise, causes the competitiveness of target product not strong.
(3) resorcinol formaldehyde methylation method
The route reaction step is more, and total recovery is relatively low, and generation technique is relative complex, and the big production operation of realityization is more difficult.
The content of the invention
In order to overcome the shortcomings of that prior art is present, the invention provides a kind of new, high-quality, suitable industry metaplasia
The preparation method of the 2,6- orcins of product.This method suitable for resorcinol as raw material, in fixed-bed reactor
Directly methyl is combined to the occasion of 2,6- orcins.
The preparation method of one kind 2,6- orcins, comprises the steps：
(1) methylation reaction：With resorcinol as raw material in fixed-bed reactor, with solid acid as catalyst, with
A certain amount of methanol is solvent and methylating reagent, carries out methylation reaction at a certain temperature；
(2) distill：By reactant liquor vacuum distillation recovered solvent, the crude product of 2,6- orcins is obtained；
(3) purification：The crude product of 2,6- orcins obtains 2,6- orcin highly finished product through recrystallization process.
Preferably, in step (1), described solid acid is SO4 2-/ZrO2-MxOyThe solid acid of type.
Preferably, solid acid is prepared by the following method：
The preparation of (a) materials with hide glue fibril metal loaded material：
The materials with hide glue fibril for taking 15g is placed in three-neck flask and stirs, with formic acid and sulfuric acid mixture liquid adjust pH to 1.8～
2.0,2h is stirred in being placed on water bath with thermostatic control, mixing speed is 180r/min, adds the Zr (SO of 30.0g4)2With it is a certain amount of
Nitrate solution, is stirred at room temperature reaction 4h, rotating speed 350r/min, uses saturation NaHCO3Solution slowly adjust pH to 4.0～
4.1,45 DEG C of constant temperature stirring reactions 8h are warming up to, reaction is filtered after terminating, is repeatedly washed with water, and room temperature aeration-drying is born
Carry the materials with hide glue fibril of metal；
(b)SO4 2-/ZrO2-MxOyThe preparation of solid acid：
The product of above-mentioned preparation is put in Muffle furnace carries out temperature programming heat treatment, will with the heating rate of 10 DEG C/min
Temperature rises to 400,500,600,700,800 DEG C respectively, and cooling after processing 4h obtains fibrous oxide ZrO2-MxOy；To produce again
Thing impregnates the sulfuric acid solution of 2mol/L, and dip time is 8h, dries, then proceed in Muffle furnace after sucking filtration in being put into 105 DEG C of baking ovens,
The constant temperature heat treatment 4h in the case where temperature is for 200,300,400,500,600,700 DEG C, prepares fibrous SO respectively4 2-/ZrO2-
MxOyThe solid acid of type.
Preferably, the solid acid is SO4 2-/ZrO2-Ni2O3Solid acid, SO4 2-/ZrO2-La2O3Solid acid, SO4 2-/
ZrO2-TiO2One kind in solid acid.
Preferably, in step (1), methylation reaction temperature is 300～400 DEG C.
Preferably, in step (1), fixed-bed reactor be one section of long 100mm, internal diameter 4.4mm it is cylindrical stainless
Steel reaction tube.
Preferably, in step (1), methanol is 8～12: 1 with the mass ratio of resorcinol.
Preferably, fixed-bed reactor is entered after methanol, resorcinol mix homogeneously, its charging rate is controlled to
0.40～0.6h-1。
Preferably, in step (3), the solvent that recrystallization is adopted is for Methanol+Water.
Preferably, the preparation method of described 2,6- orcins, comprises the steps：
(1) methylation reaction：By 1.0g solid acid SO4 2-/ZrO2-TiO2Catalyst loads one section of long 100mm, internal diameter
In the cylindrical stainless steel reaction pipe of 4.4mm, rest is filled up with inert quartz sand；By 220g methanol, 22.2g isophthalic two
Phenol mix homogeneously, is 0.50h in methanol air speed with peristaltic pump-1Under conditions of reaction mixture is pumped into into reaction tube, reaction temperature
For 350 DEG C, sampling after product is condensed, is collected；
(2) distill：By reactant liquor vacuum distillation recovered solvent, the crude product of 2,6- orcins is obtained；
(3) purification：The crude product of 2,6- orcins is added carries out recrystallization into 135ml Methanol+Waters, obtains
To 2,6- orcin highly finished product.
The present invention reduces environmental pollution, reduces cost, simple to operate while improve product quality quality, gives birth to product
Product is cleaned, environmental protection, is more suitable for producing in enormous quantities.
Specific embodiment
With reference to specific embodiment, the present invention is described further, but protection scope of the present invention is not limited in
This.
SO4 2-/ZrO2-MxOyThe preparation of solid acid
The preparation of (a) materials with hide glue fibril metal loaded material：
The materials with hide glue fibril for taking 15g is placed in three-neck flask and stirs, with formic acid and sulfuric acid mixture liquid adjust pH to 1.8～
2.0,2h is stirred in being placed on water bath with thermostatic control, mixing speed is 180r/min, adds the Zr (SO of 30.0g4)2With it is a certain amount of
Nitrate solution, is stirred at room temperature reaction 4h, rotating speed 350r/min, uses saturation NaHCO3Solution slowly adjust pH to 4.0～
4.1,45 DEG C of constant temperature stirring reactions 8h are warming up to, reaction is filtered after terminating, is repeatedly washed with water, and room temperature aeration-drying is born
Carry the materials with hide glue fibril of metal；
(b)SO4 2-/ZrO2-MxOyThe preparation of solid acid：
The product of above-mentioned preparation is put in Muffle furnace carries out temperature programming heat treatment, will with the heating rate of 10 DEG C/min
Temperature rises to 400,500,600,700,800 DEG C respectively, and cooling after processing 4h obtains fibrous oxide ZrO2-MxOy；To produce again
Thing impregnates the sulfuric acid solution of 2mol/L, and dip time is 8h, dries, then proceed in Muffle furnace after sucking filtration in being put into 105 DEG C of baking ovens,
The constant temperature heat treatment 4h in the case where temperature is for 200,300,400,500,600,700 DEG C, prepares fibrous SO respectively4 2-/ZrO2-
MxOyThe solid acid of type.
Embodiment 1
Synthetic route of the present invention is as follows：
This reaction adopts fixed bed reaction pattern, by 1.0g homemade solid acid SO4 2-/ZrO2-Ni2O3Catalyst loads one
In segment length 100mm, the cylindrical stainless steel reaction pipe of internal diameter 4.4mm, rest is filled up with inert quartz sand.Reaction is adopted
Following feeding manners, by SURPASS 102S/R-20 types peristaltic pumps by reaction mixture with the continuous pump of suitable charging rate
Enter reaction tube, the condensed rear continuous discharge of product, timing acquiring sample, acquisition time is 5.0min, course of reaction electricity consumption
Heating and temperature controlling device controlling reaction temperature.Specifically course of reaction is：By 220g methanol, 22.0g resorcinol mix homogeneously, with compacted
Dynamic pump is 0.50h in methanol air speed-1Under conditions of feed, reaction temperature be 350 DEG C, product it is condensed after collect sampling；
The reactant liquor vacuum distillation recovered solvent that reaction will be collected after terminating, solvent recovery are finished and obtain 2,6- orcin crude products
26.5g, is added into recrystallization is carried out into 135ml Methanol+Waters, obtains 2,6- orcin highly finished product
15.4g, yield 62.1%, purity 99.35%.
Embodiment 2
This reaction adopts fixed bed reaction pattern, by 1.0g homemade solid acid SO4 2-/ZrO2-La2O3Catalyst loads one
In segment length 100mm, the cylindrical stainless steel reaction pipe of internal diameter 4.4mm, rest is filled up with inert quartz sand.Reaction is adopted
Following feeding manners, by SURPASS 102S/R-20 types peristaltic pumps by reaction mixture with the continuous pump of suitable charging rate
Enter reaction tube, the condensed rear continuous discharge of product, timing acquiring sample, acquisition time is 5.0min, course of reaction electricity consumption
Heating and temperature controlling device controlling reaction temperature.Course of reaction is：By 220g methanol, 22.0g resorcinol mix homogeneously, peristaltic pump is used
It is 0.50h in methanol air speed-1Under conditions of feed, reaction temperature be 350 DEG C, product it is condensed after collect sampling；Reaction
The reactant liquor vacuum distillation recovered solvent that will be collected after end, solvent recovery are finished and obtain 2,6- orcin crude product 26.1g,
It is added into recrystallization is carried out into 135ml Methanol+Waters, obtains 2,6- orcin highly finished product 14.4g, yield
58.1%, purity 99.29%.
Embodiment 3
This reaction adopts fixed bed reaction pattern, by 1.0g homemade solid acid SO4 2-/ZrO2-TiO2Catalyst loads one
In segment length 100mm, the cylindrical stainless steel reaction pipe of internal diameter 4.4mm, rest is filled up with inert quartz sand.Reaction is adopted
Following feeding manners, by SURPASS 102S/R-20 types peristaltic pumps by reaction mixture with the continuous pump of suitable charging rate
Enter reaction tube, the condensed rear continuous discharge of product, timing acquiring sample, acquisition time is 5.0min, course of reaction electricity consumption
Heating and temperature controlling device controlling reaction temperature.Course of reaction is：By 220g methanol, 22.2g resorcinol mix homogeneously, peristaltic pump is used
It is 0.50h in methanol air speed-1Under conditions of feed, reaction temperature be 350 DEG C, product it is condensed after collect sampling；Reaction
The reactant liquor vacuum distillation recovered solvent that will be collected after end, solvent recovery are finished and obtain 2,6- orcin crude product 30.5g,
It is added into recrystallization is carried out into 135ml Methanol+Waters, obtains 2,6- orcin highly finished product 16.4g, yield
66.1%, purity 99.45%.
According to the present invention to homemade different solid acid catalysts using implementing, when with SO4 2-/ZrO2-TiO2As urging
Higher yields, highly purified 2,6- orcins can be obtained during agent.
Embodiment 4
This reaction adopts fixed bed reaction pattern, by 1.0g homemade solid acid SO4 2-/ZrO2-TiO2Catalyst loads one
In segment length 100mm, the cylindrical stainless steel reaction pipe of internal diameter 4.4mm, rest is filled up with inert quartz sand.Reaction is adopted
Following feeding manners, by SURPASS 102S/R-20 types peristaltic pumps by reaction mixture with the continuous pump of suitable charging rate
Enter reaction tube, the condensed rear continuous discharge of product, timing acquiring sample, acquisition time is 5.0min, course of reaction electricity consumption
Heating and temperature controlling device controlling reaction temperature.Course of reaction is：By 220g methanol, 22.2g resorcinol mix homogeneously, peristaltic pump is used
It is 0.60h in methanol air speed-1Under conditions of feed, reaction temperature be 350 DEG C, product it is condensed after collect sampling；Reaction
The reactant liquor vacuum distillation recovered solvent that will be collected after end, solvent recovery are finished and obtain 2,6- orcin crude product 28.5g,
It is added into recrystallization is carried out into 135ml Methanol+Waters, obtains 2,6- orcin highly finished product 15.6g, yield
62.9%, purity 99.3%.
Embodiment 5
This reaction adopts fixed bed reaction pattern, by 1.0g homemade solid acid SO4 2-/ZrO2-TiO2Catalyst loads one
In segment length 100mm, the cylindrical stainless steel reaction pipe of internal diameter 4.4mm, rest is filled up with inert quartz sand.Reaction is adopted
Following feeding manners, by SURPASS 102S/R-20 types peristaltic pumps by reaction mixture with the continuous pump of suitable charging rate
Enter reaction tube, the condensed rear continuous discharge of product, timing acquiring sample, acquisition time is 5.0min, course of reaction electricity consumption
Heating and temperature controlling device controlling reaction temperature.Course of reaction is：By 220g methanol, 22.2g resorcinol mix homogeneously, peristaltic pump is used
It is 0.40h in methanol air speed-1Under conditions of feed, reaction temperature be 350 DEG C, product it is condensed after collect sampling；Reaction
The reactant liquor vacuum distillation recovered solvent that will be collected after end, solvent recovery are finished and obtain 2,6- orcin crude product 29.1g,
It is added into recrystallization is carried out into 135ml Methanol+Waters, obtains 2,6- orcin highly finished product 15.8g, yield
63.7%, purity 99.35%.
Claims (10)
1. one kind 2, the preparation method of 6- orcins, it is characterised in that comprise the steps：
(1) methylation reaction：With resorcinol as raw material in fixed-bed reactor, with solid acid as catalyst, with certain
The methanol of amount is solvent and methylating reagent, carries out methylation reaction at a certain temperature；
(2) distill：By reactant liquor vacuum distillation recovered solvent, the crude product of 2,6- orcins is obtained；
(3) purification：The crude product of 2,6- orcins obtains 2,6- orcin highly finished product through recrystallization process.
2. the preparation method of 2,6- orcins according to claim 1, it is characterised in that：It is in step (1), described
Solid acid is SO4 2-/ZrO2-The solid acid of MxOy types.
3. the preparation method of 2,6- orcins according to claim 2, it is characterised in that：Solid acid passes through following sides
Method is prepared：
The preparation of (a) materials with hide glue fibril metal loaded material：
The materials with hide glue fibril for taking 15g is placed in three-neck flask and stirs, and adjusts pH to 1.8～2.0 with formic acid and sulfuric acid mixture liquid,
2h is stirred in being placed on water bath with thermostatic control, mixing speed is 180r/min, add the Zr (SO of 30.0g4)2With a certain amount of nitric acid
Saline solution, is stirred at room temperature reaction 4h, rotating speed 350r/min, uses saturation NaHCO3Solution slowly adjusts pH to 4.0～4.1,
45 DEG C of constant temperature stirring reactions 8h are warming up to, reaction is filtered after terminating, repeatedly washed with water, and room temperature aeration-drying obtains gold-supported
The materials with hide glue fibril of category；
(b)SO4 2-/ZrO2-The preparation of MxOy solid acids：
The product of above-mentioned preparation is put in Muffle furnace carries out temperature programming heat treatment, with the heating rate of 10 DEG C/min by temperature
400,500,600,700,800 DEG C are risen to respectively, and cooling after processing 4h obtains fibrous oxide ZrO2-MxOy；Again product is soaked
The sulfuric acid solution of stain 2mol/L, dip time are 8h, dry, then proceed in Muffle furnace, respectively after sucking filtration in being put into 105 DEG C of baking ovens
It is constant temperature heat treatment 4h at 200,300,400,500,600,700 DEG C in temperature, prepares fibrous SO4 2-/ZrO2-MxOy types
Solid acid.
4. the preparation method of 2,6- orcins according to claim 3, it is characterised in that：The solid acid is
SO4 2-/ZrO2-Ni2O3Solid acid, SO4 2-/ZrO2--La2O3Solid acid, SO4 2-/ZrO2--TiO2One kind in solid acid.
5. the preparation method of 2,6- orcins according to claim 1, it is characterised in that：In step (1), methylate
Reaction temperature is 300～400 DEG C.
6. the preparation method of 2,6- orcins according to claim 1, it is characterised in that：In step (1), fixed bed
Reaction unit is the cylindrical stainless steel reaction pipe of one section of long 100mm, internal diameter 4.4mm.
7. the preparation method of 2,6- orcins according to claim 1, it is characterised in that：In step (1), methanol with
The mass ratio of resorcinol is 8～12：1.
8. the preparation method of 2,6- orcins according to claim 1, it is characterised in that：Methanol, resorcinol are mixed
Fixed-bed reactor is entered after closing uniformly, its charging rate is controlled to 0.40～0.6h-1。
9. the preparation method of 2,6- orcins according to claim 1, it is characterised in that：In step (3), recrystallization
The solvent for adopting is for Methanol+Water.
10. the preparation method of 2,6- orcins according to claim 4, it is characterised in that comprise the steps：
(1) methylation reaction：By 1.0g solid acid SO4 2-/ZrO2--TiO2Catalyst loads one section of long 100mm, internal diameter 4.4mm
In cylindrical stainless steel reaction pipe, rest is filled up with inert quartz sand；220g methanol, 22.2g resorcinol are mixed
Uniformly, it is 0.50h in methanol air speed with peristaltic pump-1Under conditions of reaction mixture is pumped into into reaction tube, reaction temperature is 350
DEG C, sampling is collected after product is condensed；
(2) distill：By reactant liquor vacuum distillation recovered solvent, the crude product of 2,6- orcins is obtained；
(3) purification：The crude product of 2,6- orcins is added carries out recrystallization into 135ml Methanol+Waters, obtains 2,
6- orcin highly finished product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610963261.2A CN106554255B (en) | 2016-11-04 | 2016-11-04 | A kind of preparation method of 2,6- dihydroxytoluene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610963261.2A CN106554255B (en) | 2016-11-04 | 2016-11-04 | A kind of preparation method of 2,6- dihydroxytoluene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106554255A true CN106554255A (en) | 2017-04-05 |
| CN106554255B CN106554255B (en) | 2019-08-06 |
Family
ID=58444022
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610963261.2A Active CN106554255B (en) | 2016-11-04 | 2016-11-04 | A kind of preparation method of 2,6- dihydroxytoluene |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106554255B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111170958A (en) * | 2019-12-25 | 2020-05-19 | 浙江鼎龙科技有限公司 | Preparation method of hydroxybenzomorph |
| CN116283500A (en) * | 2023-02-13 | 2023-06-23 | 内蒙古源宏精细化工有限公司 | Synthesis method of high-purity 2,6-dihydroxytoluene |
| CN117567249A (en) * | 2023-11-22 | 2024-02-20 | 昂吉(上海)环保新材料科技有限公司 | Preparation method of 2, 6-dihydroxytoluene |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4086281A (en) * | 1975-04-03 | 1978-04-25 | Koppers Company, Inc. | Process for producing mono-substituted alkylresorcinol isomers |
| JPS5488227A (en) * | 1977-12-22 | 1979-07-13 | Seitetsu Kagaku Co Ltd | Preparation of 2,6-dihydrocy-toluene |
| CN102658174A (en) * | 2012-05-04 | 2012-09-12 | 四川大学 | Mesoporous fibrous SO4<2->/MxOy type solid acid catalyst and preparation method thereof |
-
2016
- 2016-11-04 CN CN201610963261.2A patent/CN106554255B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4086281A (en) * | 1975-04-03 | 1978-04-25 | Koppers Company, Inc. | Process for producing mono-substituted alkylresorcinol isomers |
| JPS5488227A (en) * | 1977-12-22 | 1979-07-13 | Seitetsu Kagaku Co Ltd | Preparation of 2,6-dihydrocy-toluene |
| CN102658174A (en) * | 2012-05-04 | 2012-09-12 | 四川大学 | Mesoporous fibrous SO4<2->/MxOy type solid acid catalyst and preparation method thereof |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111170958A (en) * | 2019-12-25 | 2020-05-19 | 浙江鼎龙科技有限公司 | Preparation method of hydroxybenzomorph |
| CN116283500A (en) * | 2023-02-13 | 2023-06-23 | 内蒙古源宏精细化工有限公司 | Synthesis method of high-purity 2,6-dihydroxytoluene |
| CN116283500B (en) * | 2023-02-13 | 2024-05-07 | 内蒙古源宏精细化工有限公司 | Synthesis method of high-purity 2, 6-dihydroxytoluene |
| CN117567249A (en) * | 2023-11-22 | 2024-02-20 | 昂吉(上海)环保新材料科技有限公司 | Preparation method of 2, 6-dihydroxytoluene |
| CN117567249B (en) * | 2023-11-22 | 2024-04-26 | 昂吉(上海)环保新材料科技有限公司 | Preparation method of 2, 6-dihydroxytoluene |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106554255B (en) | 2019-08-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108659213B (en) | Method for preparing polyether carboxylate by adopting micro-flow field reaction technology | |
| CN108863760B (en) | Method for continuously producing glyoxylic acid by using microchannel reactor | |
| CN106748764A (en) | The continuous synthesis system and method for a kind of 4 chloroacetyl acetacetic ester | |
| CN106554255A (en) | A kind of preparation method of 2,6 orcin | |
| CN108794405B (en) | Method for continuously preparing Olaparib intermediate by adopting micro-channel modular reaction device | |
| CN103524343A (en) | Method for synthesizing hydroxy-propyl acrylate | |
| US20210261517A1 (en) | Method for simultaneously preparing 2-ethoxyphenol and 1,3-benzodioxolane-2-one | |
| CN107159217A (en) | A kind of Cu ZnO/SiO2Aeroge bimetallic catalyst and its production and use | |
| CN1193972C (en) | Continuous method for production of cinnamaldehyde and dihydrocinnamaldehyde derivatives | |
| CN104557564B (en) | Preparation method of phenylmethylamine | |
| CN105367431B (en) | 3 N of one kind, the preparation method of N dimethylamino ethyl acrylates | |
| CN103497157B (en) | 2-imidazolidone synthesis method | |
| CN104710402B (en) | Dicyclohexyl crown ether synthesis method | |
| CN111943819A (en) | Method for preparing deca-dialdehyde intermediate | |
| CN107074701B (en) | Process for preparing 2, 3-butanediol | |
| CN107814691B (en) | Method for synthesizing ethylguaiacol | |
| CN107417494B (en) | Method for preparing fatty alcohol by in-situ hydrogenation of fatty acid | |
| CN105820054A (en) | Preparation method of 3-methoxy-2-nitrobenzoate | |
| CN114539030A (en) | Method for preparing 2,2 ' -dihydroxy-3, 3 ', 5,5 ' -tetra-tert-butyl biphenyl by using microchannel reactor | |
| CN101148406A (en) | Method for preparing carboxylic acid ester by using aldehyde, alcohol and oxidizing agent as raw material | |
| CN112679335A (en) | System and method for preparing fatty alcohol polyether carboxylic acid through catalytic oxidation | |
| CN116082140A (en) | Method for preparing isooctanoic acid by isooctanol selective oxidation | |
| CN115093346B (en) | Method for preparing nitrile compound from different substituted cycloalkanone in one step | |
| CN110713442A (en) | Preparation method of o-nitrobenzaldehyde | |
| CN102838569A (en) | Method for synthesizing peach aldehyde by using microreactor device |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CP01 | Change in the name or title of a patent holder | ||
| CP01 | Change in the name or title of a patent holder |
Address after: 311228 Linjiang Industrial Park, Xiaoshan District, Zhejiang, Hangzhou Patentee after: Zhejiang DINGLONG Technology Co.,Ltd. Patentee after: JIANGSU DINGLONG TECHNOLOGY Co.,Ltd. Address before: 311228 Linjiang Industrial Park, Xiaoshan District, Zhejiang, Hangzhou Patentee before: ZHEJIANG DINGLONG TECHNOLOGY Co.,Ltd. Patentee before: JIANGSU DINGLONG TECHNOLOGY Co.,Ltd. |
|
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20230327 Address after: 311228 Linjiang Industrial Park, Xiaoshan District, Zhejiang, Hangzhou Patentee after: Zhejiang DINGLONG Technology Co.,Ltd. Address before: 311228 Linjiang Industrial Park, Xiaoshan District, Zhejiang, Hangzhou Patentee before: Zhejiang DINGLONG Technology Co.,Ltd. Patentee before: JIANGSU DINGLONG TECHNOLOGY Co.,Ltd. |