CN103848724A - Process for producing resorcinol by hydrolyzing m-phenylenediamine - Google Patents
Process for producing resorcinol by hydrolyzing m-phenylenediamine Download PDFInfo
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- CN103848724A CN103848724A CN201410100819.5A CN201410100819A CN103848724A CN 103848724 A CN103848724 A CN 103848724A CN 201410100819 A CN201410100819 A CN 201410100819A CN 103848724 A CN103848724 A CN 103848724A
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- resorcinol
- mphenylenediamine
- hydrolysis
- crude product
- tio
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- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 title claims abstract description 69
- 238000000034 method Methods 0.000 title claims abstract description 24
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 title abstract 4
- 229940018564 m-phenylenediamine Drugs 0.000 title abstract 4
- 230000003301 hydrolyzing effect Effects 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 21
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- 239000012043 crude product Substances 0.000 claims abstract description 13
- 239000000047 product Substances 0.000 claims abstract description 12
- 239000007787 solid Substances 0.000 claims abstract description 11
- 238000010438 heat treatment Methods 0.000 claims abstract description 10
- 239000003930 superacid Substances 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 7
- 238000001914 filtration Methods 0.000 claims abstract description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 10
- 238000004821 distillation Methods 0.000 claims description 10
- 230000007062 hydrolysis Effects 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 229910010413 TiO 2 Inorganic materials 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 3
- 229910006404 SnO 2 Inorganic materials 0.000 claims description 3
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 2
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000000638 solvent extraction Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 abstract description 7
- 239000002351 wastewater Substances 0.000 abstract description 5
- 239000003377 acid catalyst Substances 0.000 abstract description 2
- 229960001755 resorcinol Drugs 0.000 description 22
- 238000003756 stirring Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 238000005485 electric heating Methods 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 238000009413 insulation Methods 0.000 description 5
- UNEATYXSUBPPKP-UHFFFAOYSA-N 1,3-Diisopropylbenzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1 UNEATYXSUBPPKP-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000007500 overflow downdraw method Methods 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
- WOQYSKVUOZYYAR-UHFFFAOYSA-N BNc1cccc(-c2c[bH]2)c1 Chemical compound BNc1cccc(-c2c[bH]2)c1 WOQYSKVUOZYYAR-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000010808 liquid waste Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000011120 plywood Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
Images
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
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/045—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of a group bound to the ring by nitrogen
- C07C37/05—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of a group bound to the ring by nitrogen by substitution of a NH2 group
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a process for producing resorcinol by hydrolyzing m-phenylenediamine, which comprises the following specific steps: 1) adding m-phenylenediamine, an acid catalyst, a solid super acid catalyst and water into a high-pressure hydrolysis reaction kettle in proportion, and uniformly mixing to obtain a mixed reaction solution; 2) heating the reactor to hydrolyze m-phenylenediamine to obtain resorcinol hydrolysis reaction liquid; 3) filtering the hydrolysis reaction liquid, and extracting the hydrolysis reaction liquid by a solvent to obtain a resorcinol crude product; 4) and distilling the resorcinol crude product under reduced pressure to obtain a resorcinol finished product. The invention has the advantages of less pollution, less wastewater discharge, easily controlled process conditions and high product yield.
Description
Technical field
The present invention relates to a kind of preparation technology of Resorcinol, more particularly, the present invention relates to a kind of method of preparing Resorcinol that is hydrolyzed take mphenylenediamine as raw material.
Background technology
Resorcinol is commonly called as resorcin, has another name called Resorcinol, 1,3-dihydroxy-benzene etc.Resorcinol is as a kind of important organic intermediate, in fields such as agricultural chemicals, dyestuff, coating, medicine, plastics, rubber, electronic chemical products, the tamanori wherein used mainly for the preparation of tire cord, use for synthetic rubber tacky resin, Plywood high performance adhesive, synthetic benzophenone UV light absorber, Metha Amino Phenon, as sanitas etc.The route of the synthetic Resorcinol of industrialization at present mainly contains the sulfonated alkali fusion method take benzene as raw material, the oxidation style take m-Diisopropylbenzene as raw material.
1. benzene sulfonated alkali fusion method
2. m-Diisopropylbenzene oxidation style
Sulfonation method is take benzene and sulfuric acid as raw material, technique comprises the steps such as sulfonation, neutralization, alkali fusion and acidifying, the method technique is simple, equipment requirements is not high, but Production Flow Chart is tediously long, consume a large amount of strong acid (as sulfuric acid, hydrochloric acid), highly basic (as sodium hydroxide), produce a large amount of inorganic salt (as sodium sulfate, S-WAT) and waste liquid simultaneously, environmentally friendly degree is low; And oxidation style is first m-Diisopropylbenzene to be oxidized into Dihydroperoxide Diisopropyl Benzene, under acidic conditions, decompose and obtain Resorcinol and by product acetone again, waste water, waste gas that the method produces are all little, pollute also less, cost is also lower, but technical requirements is higher, and oxidation, extraction process is more complicated, be subject to the restriction of m-Diisopropylbenzene raw material, suitability for industrialized production not yet makes a breakthrough so far simultaneously.
Mphenylenediamine hydrolysis process is because raw material sources facility, technical process are short, good environmental protection presents good application prospect, and corresponding, the High Temperature High Pressure of hydrolysis reaction and acidic medium operating mode have proposed higher requirement to reactor material erosion resistance.Solid super acid catalyst has some unique advantages, and as the simple inorganics of one, its preparation is very simple, thereby cost is low; Corrosion-free to equipment, overcome the shortcoming of many liquid acid severe corrosion equipments; Moisture-stable; Separate easily; Regeneration easily, can reuse.
Summary of the invention
The object of the invention provides a kind of technique that Resorcinol is produced in the mphenylenediamine hydrolysis little, cost is low of polluting in order to improve the deficiencies in the prior art.
Technical scheme of the present invention is: mphenylenediamine, acid catalyst, solid super acid catalyst and water are joined in acid-resistant reactor, sealed reactor also heats mixing raw material and makes mphenylenediamine generation hydrolysis reaction and generate Resorcinol, then the material after hydrolysis reaction being completed extracts, then extraction phase solution distillation processing is obtained to Resorcinol finished product.
Concrete technical scheme of the present invention is: the technique that Resorcinol is produced in a kind of mphenylenediamine hydrolysis, its concrete steps are as follows: 1) mphenylenediamine, an acidic catalyst, solid super acid catalyst and water are joined in highly pressured hydrolysis reactor in proportion, mix, obtain mixed reaction solution; 2) reactor heating, makes mphenylenediamine hydrolysis obtain Resorcinol hydrolysis reaction liquid; 3) to hydrolysis reaction liquid after filtration, solvent extraction obtains Resorcinol crude product; 4) underpressure distillation of Resorcinol crude product is obtained to Resorcinol finished product.
Preferably described an acidic catalyst is at least the one in sulfuric acid, phosphoric acid or hydrochloric acid; Solid super acid catalyst is at least SO
4 2-/ TiO
2-L
a2o
3, SO
4 2-/ F
e2o
3, SO
4 2-/ Al
2o
3, SO
4 2-/ TiO
2-SnO
2, SO
4 2-/ ZrO
2-TiO
2, M
oo
3/ TiO
2or SiO
2/ ZrO
2in one.
Preferably the molar ratio of mphenylenediamine, an acidic catalyst is mphenylenediamine: an acidic catalyst (pure)=be 1:(0.15～1.9); In the mixed reaction solution that described mphenylenediamine forms at mphenylenediamine, an acidic catalyst, solid super acid catalyst and water, shared weight ratio is 5～15%; Described solid super acid catalyst shared weight ratio in mixed reaction solution is 1～10%.
Preferred reactor heating and temperature control is at 190 ℃～270 ℃, and pressure-controlling is at 1.8～2.3MPa, and the reaction times is 4～12 hours.
Preferred steps 3) in the solvent of extraction be one or more the mixture in n-butyl acetate, ethyl acetate, propyl carbinol, isopropylcarbinol, ether, diisopropyl ether, glycol dimethyl ether or pimelinketone; Preferred steps 4) in the pressure of Resorcinol crude product underpressure distillation be 1.5～4Kpa.
Concrete reaction equation is as follows:
Beneficial effect:
Adopt the direct catalysis method of mphenylenediamine to produce Resorcinol, pollute few, discharge of wastewater is little, processing condition are easy to control, product yield is high, has not only solved the pollution problem of always perplexing sulfonated alkali fusion method production Resorcinol enterprise, and effectively suppresses the generation of side reaction, the yield that improves Resorcinol, reduces burnt shape deposits yields.Solid super-strong acid can recycling.
Sulfonated alkali fusion method is produced Resorcinol, in production process, consume a large amount of strong acid (as sulfuric acid, hydrochloric acid), highly basic (as sodium hydroxide), produce a large amount of inorganic salt (as sodium sulfate, S-WAT) and waste liquid simultaneously, liquid waste disposal expense is higher, also have larger waste water, environmentally friendly degree is low simultaneously.The waste water that this technique produces is few, has greatly reduced the pollution to environment.
Accompanying drawing explanation
The process flow sheet of Fig. 1 mphenylenediamine hydrolysis method.
Embodiment
Embodiment 1:
In the 5L autoclave of being furnished with stirring (electric heating coil heating), add 216.0g mphenylenediamine, 350.0g hydrochloric acid (concentration 30%), 2200g water, 27.94g SO
4 2-/ ZrO
2-TiO
2, feed temperature is no more than 80 ℃, adds rear stirring 30min, makes mixing of materials even.After airtight, be heated to 200 ℃, pressure is 1.8MPa, and insulation reaction 10 hours cools to 30 ℃ of room temperatures after reaction finishes; Take out reaction solution, filter, use 250.0g extracted with diethyl ether 4 times, steam solvent and obtain crude product 175.0g, content is 95.50%, under 1.8KPa, obtains product 162.0g through distillation, and content is 99.38%.
Embodiment 2:
In the 5L autoclave of being furnished with stirring (electric heating coil heating), add 220.8g mphenylenediamine, 368.0g sulfuric acid (concentration 98%), 2600g water, 354.31g SO
4 2-/ ZrO
2-TiO
2, feed temperature is no more than 80 ℃, adds rear stirring 30min, makes mixing of materials even.After airtight, be heated to 220 ℃, pressure is 2.2MPa, and insulation reaction 8 hours cools to 30 ℃ of room temperatures after reaction finishes; Take out reaction solution, filter, with 400g ethyl acetate extraction 4 times, steam solvent and obtain crude product 185.0g, content is 95.30%, obtains product 178.0g at 2.0KPa through distillation, and content is 99.40%.
Embodiment 3:
In the 5L autoclave of being furnished with stirring (electric heating coil heating), add 426.0g mphenylenediamine, 240.0g hydrochloric acid (concentration 30%), 2600g water, 40.0g SO
4 2-/ TiO
2-SnO
2, feed temperature is no more than 80 ℃, adds rear stirring 30min, makes mixing of materials even.After airtight, be heated to 200 ℃, pressure is 2MPa, and insulation reaction 4 hours cools to 30 ℃ of room temperatures after reaction finishes; Take out reaction solution, filter, with 500g isopropylcarbinol extraction 4 times, steam solvent and obtain crude product 295.0g, content is 95.25%, obtains product 281.0g at 1.9KPa through distillation, and content is 99.50%.
Embodiment 4:
In the 5L autoclave of being furnished with stirring (electric heating coil heating), add 151.8g mphenylenediamine, 184.0g sulfuric acid (concentration 98%), 2600g water, 100.0g SO
4 2-/ Al
2o
3, feed temperature is no more than 80 ℃, adds rear stirring 30min, makes mixing of materials even.After airtight, be heated to 270 ℃, pressure is 1.9MPa, and insulation reaction 5 hours cools to 30 ℃ of room temperatures after reaction finishes; Take out reaction solution, filter, use 300g extracted with diethyl ether 4 times, steam solvent and obtain crude product 113.0g, content is 95.35%, obtains product 95.0g at 2.3KPa through distillation, and content is 99.45%.
Embodiment 5:
In the 5L autoclave of being furnished with stirring (electric heating coil heating), add 450g mphenylenediamine, 110.0g sulfuric acid (concentration 98%), 2400g water, 50.0g SO
4 2-/ Fe
2o
3, feed temperature is no more than 80 ℃, adds rear stirring 30min, makes mixing of materials even.After airtight, be heated to 230 ℃, pressure is 2MPa, and insulation reaction 7 hours cools to 30 ℃ of room temperatures after reaction finishes; Take out reaction solution, filter, with 600g diisopropyl ether extraction 4 times, steam solvent and obtain crude product 390g, content is 95.24%, obtains product 372g at 3.8KPa through distillation, and content is 99.38%.
Claims (6)
1. the technique that Resorcinol is produced in mphenylenediamine hydrolysis, its concrete steps are as follows: 1) mphenylenediamine, an acidic catalyst, solid super acid catalyst and water are joined in highly pressured hydrolysis reactor in proportion, mix, obtain mixed reaction solution; 2) reactor heating, makes mphenylenediamine hydrolysis obtain Resorcinol hydrolysis reaction liquid; 3) to hydrolysis reaction liquid after filtration, solvent extraction obtains Resorcinol crude product; 4) underpressure distillation of Resorcinol crude product is obtained to Resorcinol finished product.
2. technique according to claim 1, is characterized in that: described an acidic catalyst is at least the one in sulfuric acid, phosphoric acid or hydrochloric acid; Solid super acid catalyst is at least SO
4 2-/ TiO
2-La
2o
3, SO
4 2-/ Fe
2o
3, SO
4 2-/ Al
2o
3, SO
4 2-/ TiO
2-SnO
2, SO
4 2-/ ZrO
2-TiO
2, MoO
3/ TiO
2or SiO
2/ ZrO
2in one.
3. technique according to claim 1, is characterized in that: the molar ratio of mphenylenediamine, an acidic catalyst is 1:(0.15～1.9); Described mphenylenediamine shared weight ratio in mixed reaction solution is 5～15%; Described solid super acid catalyst shared weight ratio in mixed reaction solution is 1～10%.
4. technique according to claim 1, is characterized in that: reactor heating and temperature control is at 190 ℃～270 ℃, and pressure-controlling is at 1.8～2.3MPa, and the reaction times is 4～12 hours.
5. technique according to claim 1, is characterized in that: the solvent extracting in step 3) is one or more the mixture in n-butyl acetate, ethyl acetate, propyl carbinol, isopropylcarbinol, ether, diisopropyl ether, glycol dimethyl ether or pimelinketone.
6. technique according to claim 1, is characterized in that: in step 4), the pressure of Resorcinol crude product underpressure distillation is 1.5～4Kpa.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104262109A (en) * | 2014-09-01 | 2015-01-07 | 湖南湘易康制药有限公司 | Synthesis method of resorcinol |
| CN107262150A (en) * | 2017-06-06 | 2017-10-20 | 青岛科技大学 | A kind of preparation method of m-phenylene diamine (MPD) hydrolysis load-type solid acid catalyst |
| CN109422659A (en) * | 2017-08-23 | 2019-03-05 | 中国石油化工股份有限公司 | A kind of method that m-phenylene diamine (MPD) hydrolysis prepares meta-aminophenol |
| CN109516924A (en) * | 2018-11-14 | 2019-03-26 | 南京工业大学 | Method for preparing m-aminophenol by catalyzing resorcinol |
| CN114149306A (en) * | 2021-12-09 | 2022-03-08 | 青岛科技大学 | Synthesis process of resorcinol |
| CN114163311A (en) * | 2020-09-11 | 2022-03-11 | 王兴路 | High-efficiency and clean production method of phenolic compound |
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2014
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|---|---|---|---|---|
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|---|
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104262109A (en) * | 2014-09-01 | 2015-01-07 | 湖南湘易康制药有限公司 | Synthesis method of resorcinol |
| CN107262150A (en) * | 2017-06-06 | 2017-10-20 | 青岛科技大学 | A kind of preparation method of m-phenylene diamine (MPD) hydrolysis load-type solid acid catalyst |
| CN107262150B (en) * | 2017-06-06 | 2018-10-16 | 青岛科技大学 | A kind of preparation method of m-phenylene diamine (MPD) hydrolysis load-type solid acid catalyst |
| CN109422659A (en) * | 2017-08-23 | 2019-03-05 | 中国石油化工股份有限公司 | A kind of method that m-phenylene diamine (MPD) hydrolysis prepares meta-aminophenol |
| CN109422659B (en) * | 2017-08-23 | 2022-02-11 | 中国石油化工股份有限公司 | Method for preparing m-aminophenol by hydrolyzing m-phenylenediamine |
| CN109516924A (en) * | 2018-11-14 | 2019-03-26 | 南京工业大学 | Method for preparing m-aminophenol by catalyzing resorcinol |
| CN114163311A (en) * | 2020-09-11 | 2022-03-11 | 王兴路 | High-efficiency and clean production method of phenolic compound |
| CN114149306A (en) * | 2021-12-09 | 2022-03-08 | 青岛科技大学 | Synthesis process of resorcinol |
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