CN116969815B - Hydroquinone purifying and dehydrating method - Google Patents
Hydroquinone purifying and dehydrating method Download PDFInfo
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- CN116969815B CN116969815B CN202311240784.0A CN202311240784A CN116969815B CN 116969815 B CN116969815 B CN 116969815B CN 202311240784 A CN202311240784 A CN 202311240784A CN 116969815 B CN116969815 B CN 116969815B
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- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 title claims abstract description 155
- 238000000034 method Methods 0.000 title claims abstract description 35
- 239000012535 impurity Substances 0.000 claims abstract description 62
- 238000000605 extraction Methods 0.000 claims abstract description 44
- 239000011347 resin Substances 0.000 claims abstract description 39
- 229920005989 resin Polymers 0.000 claims abstract description 39
- 239000002184 metal Substances 0.000 claims abstract description 35
- 238000001179 sorption measurement Methods 0.000 claims abstract description 32
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims abstract description 30
- 229960003638 dopamine Drugs 0.000 claims abstract description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000001914 filtration Methods 0.000 claims abstract description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 21
- 239000003456 ion exchange resin Substances 0.000 claims description 21
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 21
- 229920000193 polymethacrylate Polymers 0.000 claims description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 239000012982 microporous membrane Substances 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- -1 dicyclopentadienyl acrylate Chemical compound 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 8
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
- 238000001035 drying Methods 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
- 229920002292 Nylon 6 Polymers 0.000 claims description 3
- 239000004695 Polyether sulfone Substances 0.000 claims description 3
- 239000004743 Polypropylene Substances 0.000 claims description 3
- 229920002492 poly(sulfone) Polymers 0.000 claims description 3
- 229920006393 polyether sulfone Polymers 0.000 claims description 3
- 229920001155 polypropylene Polymers 0.000 claims description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- 239000004677 Nylon Substances 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 229920001778 nylon Polymers 0.000 claims description 2
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052755 nonmetal Inorganic materials 0.000 claims 1
- 150000002500 ions Chemical class 0.000 abstract description 8
- IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 abstract description 6
- 230000008901 benefit Effects 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 4
- 238000009776 industrial production Methods 0.000 abstract description 3
- 238000007670 refining Methods 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000001728 nano-filtration Methods 0.000 description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 238000001694 spray drying Methods 0.000 description 4
- 238000005265 energy consumption Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000001471 micro-filtration Methods 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 229940079877 pyrogallol Drugs 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- 241000234282 Allium Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- NOAAXTYBJHDTFV-UHFFFAOYSA-N CC(C(C1(C(O)=CC=C(CCN)C1)O)=O)=C Chemical compound CC(C(C1(C(O)=CC=C(CCN)C1)O)=O)=C NOAAXTYBJHDTFV-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000023556 desulfurization Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- LUCXVPAZUDVVBT-UHFFFAOYSA-N methyl-[3-(2-methylphenoxy)-3-phenylpropyl]azanium;chloride Chemical compound Cl.C=1C=CC=CC=1C(CCNC)OC1=CC=CC=C1C LUCXVPAZUDVVBT-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- AMLFJZRZIOZGPW-UHFFFAOYSA-N prop-1-en-1-amine Chemical group CC=CN AMLFJZRZIOZGPW-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000010057 rubber processing Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing 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
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
-
- 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/265—Synthetic macromolecular compounds modified or post-treated polymers
-
- 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
- C07C37/72—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by liquid-liquid 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
- C07C37/82—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by solid-liquid treatment; by chemisorption
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the technical field of hydroquinone refining, and discloses a hydroquinone purifying and dehydrating method; the method adopts a method combining secondary filtration and tertiary countercurrent extraction to purify and dehydrate hydroquinone; in the dicyclopentadienyl/dopamine-based/adsorption resin, amino and phenolic hydroxyl in dicyclopentadienyl and dopamine-based can form coordination bonds with ions or ion groups in metal impurities; in the adsorption process, coordination bonds in the dicyclopentadienyl/dopamine group/adsorption resin can form stable complexes with ions or ion groups in the metal impurities, so that the metal impurities are adsorbed on the resin; the coordination can improve the adsorption effect of the adsorption resin on metal impurities, thereby improving the adsorption capacity and the adsorption rate; the hydroquinone purifying and dehydrating method has the advantages of high extraction efficiency, high product purity, low water content and the like, and is suitable for industrial production.
Description
Technical Field
The invention relates to the technical field of hydroquinone refining, in particular to a hydroquinone purifying and dehydrating method.
Background
Hydroquinone, also known as hydroquinone, is an important raw material, auxiliary agent and intermediate for rubber, medicine, dye, pesticide and fine chemical industry. The black-white developer, the green onion wake dye and the azo dye, the auxiliary solvent of the synthetic gas desulfurization process, the rubber processing anti-aging agent and the polymerization inhibitor, the stabilizer and the antioxidant for food and paint are mainly used for preparing photographic films. In addition, can also be used as petroleum anticoagulant, synthetic ammonia catalyst, etc.
Chinese patent CN101479224B: relates to a preparation method of purified hydroquinone and molding thereof. The invention is useful for obtaining purified hydroquinone from a starting compound that contains mainly hydroquinone with a small amount of impurities, including resorcinol and pyrogallol. The invention is also used to obtain hydroquinone in an easy-to-process form. The inventive method (which starts from the raw hydroquinone containing the above impurities) is characterized in that: it comprises a distillative purification step which can remove resorcinol and pyrogallol, followed by a step of shaping the purified hydroquinone.
Chinese patent CN114534281B: the utility model discloses a hydroquinone spray drying device and method, relate to hydroquinone spray drying field, the easy absorption of a large amount of hydroquinone white crystallization of barrel inner wall when having solved current hydroquinone spray drying device and using, do not clear up for a long time can lead to the hydroquinone output efficiency to reduce and influence barrel life's problem, including barrel and shake device, fixedly connected with air heating device on the barrel, set up the device groove in the barrel, device inslot fixedly connected with elasticity inner bag, this hydroquinone spray drying device, through setting up air heating device and shake device, be convenient for through air heating device's drive, drive shake device operation, thereby make elasticity inner bag carry out moderate reciprocal shake, firstly will the white crystallization of hydroquinone absorbed on the elasticity inner bag shakes off, secondly can make through the shake of elasticity inner bag atomizing hydroquinone in the elasticity inner bag fully contacts with high temperature air.
Chinese patent CN116283509a: the production method of the electronic chemical hydroquinone comprises a dissolving step, a microfiltration step, an anion and cation removal step, a flash evaporation separation step or a rectification separation step, a nanofiltration step, a crystallization step and a drying step, wherein the dissolving step is to dissolve industrial-grade hydroquinone by adopting a reagent to obtain a hydroquinone solution; the flash evaporation separation step is to separate components from the hydroquinone solution obtained after the nanofiltration step through a flash evaporation tank; the rectification separation step is to separate components of the hydroquinone solution before the nanofiltration step through a first rectification tower and a second rectification tower; crystallizing the hydroquinone solution obtained after the flash separation step or the hydroquinone solution obtained after nanofiltration by a crystallizer; the drying step is to dry the hydroquinone product after the crystallization step; a heating step is also included. The product has high purity and low impurity content, and can meet the highest standard SEMIC12 (G4) of electronic chemicals and the high-purity hydroquinone required above.
In the prior art, most of the purification and dehydration technologies of hydroquinone adopt distillation or rectification methods, and the problems of high hydroquinone heat-sensitive loss, low separation yield, high energy consumption and the like in the separation process generally exist. Therefore, development of a low-product-loss, energy-saving and efficient hydroquinone purification and dehydration method is needed.
Disclosure of Invention
The invention aims to provide a method for purifying and dehydrating hydroquinone, which adopts a method combining secondary filtration and tertiary countercurrent extraction, can reduce energy consumption, reduce the thermosensitive loss of hydroquinone, improve the economic benefit of the device and is suitable for industrial production.
The aim of the invention is achieved by the following technical scheme:
a hydroquinone purifying and dehydrating method comprises the following operation steps:
s1: sending the crude hydroquinone to a primary filter and a secondary filter to remove part of metal impurities, nonmetallic impurities and organic impurities; the primary filter adopts ion exchange resin with the aperture of 0.3-0.6 mm; the ion exchange resin is metal impurity adsorption resin; the preparation method comprises the following steps:
adding 100-150 parts by weight of primary amino polymethacrylate resin, 3-7 parts by weight of dicyclopentadienyl acrylate, 1-4 parts by weight of 3-methacryloyl dopamine, 2-5 parts by weight of tetramethylguanidine, 500-1000 parts by weight of DMF (dimethyl formamide), mixing at 40-50 ℃ for 100-150 minutes, filtering, and drying to obtain metal impurity adsorption resin;
s2: sending the filtered hydroquinone into an extraction tower A, an extraction tower B and an extraction tower C filled with an extracting agent, and carrying out three-stage countercurrent extraction to further remove metal impurities, nonmetallic impurities, organic impurities and water to obtain the hydroquinone.
Preferably, the primary amino polymethacrylate resin is an acrylic ion exchange resin produced by Zhejiang light control industries, inc., and is one of the model EA104F, EA109F, EA F.
Preferably, the secondary filter adopts one or more of polypropylene microporous membrane, nylon 6 microporous membrane, nylon microporous membrane, polysulfone microporous membrane and polyether sulfone microporous membrane with the aperture of 0.1-0.5 mu m.
Preferably, in the step S1, the extractant is one or more of benzene, ethyl acetate, isopropyl ether, butyl acetate, trimethyl phosphate, and acetophenone.
Preferably, in the step S1, the extraction temperature of the three-stage countercurrent extraction is 20-40 ℃.
Preferably, in the step S1, the mass ratio of the extractant to the hydroquinone is 1:0.8-3.
The principle of the invention is as follows:
the metal impurity adsorption resin adopts primary amino polymethacrylate resin to respectively carry out amino-propylene addition reaction with dicyclopentenyl acrylic ester and 3-methacryloyl dopamine to obtain dicyclopentenyl/dopamine group/adsorption resin.
Compared with the prior art, the hydroquinone purifying and dehydrating method has the following remarkable effects:
1. in the dicyclopentadienyl/dopamine-based/adsorption resin, amino and phenolic hydroxyl in dicyclopentadienyl and dopamine-based can form coordination bonds with ions or ion groups in metal impurities; in the adsorption process, coordination bonds in the dicyclopentadienyl/dopamine group/adsorption resin can form stable complexes with ions or ion groups in the metal impurities, so that the metal impurities are adsorbed on the resin; the coordination can improve the adsorption effect of the adsorption resin on the metal impurities, and the formation of coordination bonds can increase the interaction force between the adsorption resin and the metal impurities, so that the adsorption capacity and the adsorption rate are improved;
2. the invention adopts a method combining secondary filtration and tertiary countercurrent extraction to purify and dehydrate hydroquinone, thereby reducing energy consumption, reducing hydroquinone heat-sensitive loss and improving economic benefit of the device;
3. the hydroquinone purifying and dehydrating method has the advantages of high extraction efficiency, high product purity, low water content and the like;
4. the hydroquinone purifying and dehydrating method has the advantages of simple process, easy operation, small investment and suitability for industrial production.
Detailed Description
The invention is further illustrated by the following examples:
example 1
The hydroquinone purifying and dewatering process includes the following steps:
s1: sending the crude hydroquinone to a primary filter and a secondary filter to remove part of metal impurities, nonmetallic impurities and organic impurities;
s2: sending the filtered hydroquinone into an extraction tower A, an extraction tower B and an extraction tower C filled with an extracting agent, and carrying out three-stage countercurrent extraction to further remove metal impurities, nonmetallic impurities, organic impurities and water to obtain the hydroquinone.
The primary filter adopts ion exchange resin with the aperture of 0.3 mm.
The ion exchange resin is metal impurity adsorption resin; the preparation method comprises the following steps:
100kg of primary amino polymethacrylate resin, 3kg of dicyclopentenyl acrylic ester, 1kg of 3-methyl acrylamide dopamine, 2kg of tetramethylguanidine and 500kg of DMF are added into a reaction kettle, and the mixture is stirred for 100 minutes at 40 ℃, filtered and dried to obtain the metal impurity adsorption resin.
The primary amino polymethacrylate resin is acrylic acid ion exchange resin produced by Zhejiang light-striving industry Co., ltd, and the model is EA104F.
The secondary filter adopts a polypropylene microporous membrane with the pore diameter of 0.1 mu m.
The extractant is benzene.
The extraction temperature is 20 ℃.
The mass ratio of the extractant to the hydroquinone is 1:0.8.
example 2
The hydroquinone purifying and dewatering process includes the following steps:
s1: sending the crude hydroquinone to a primary filter and a secondary filter to remove part of metal impurities, nonmetallic impurities and organic impurities;
s2: sending the filtered hydroquinone into an extraction tower A, an extraction tower B and an extraction tower C filled with an extracting agent, and carrying out three-stage countercurrent extraction to further remove metal impurities, nonmetallic impurities, organic impurities and water to obtain the hydroquinone.
The primary filter adopts ion exchange resin with the aperture of 0.4 mm.
The ion exchange resin is metal impurity adsorption resin; the preparation method comprises the following steps:
110kg of primary amino polymethacrylate resin, 4kg of dicyclopentenyl acrylic ester, 2kg of 3-methyl acrylamide dopamine, 3kg of tetramethylguanidine and 600kg of DMF are added into a reaction kettle, and the mixture is stirred for 110 minutes at 45 ℃, filtered and dried to obtain the metal impurity adsorption resin.
The primary amino polymethacrylate resin is an acrylic acid ion exchange resin produced by Zhejiang light-striving industry Co., ltd, and the model is EA109F.
The secondary filter adopts a nylon 6 microporous membrane with the aperture of 0.2 mu m.
The extraction tower A, the extraction tower B and the extraction tower C are filled with an extractant, and the extractant is ethyl acetate.
The extraction temperature is 25 ℃.
The mass ratio of the extractant to the hydroquinone is 1:1.5.
example 3
The hydroquinone purifying and dewatering process includes the following steps:
s1: sending the crude hydroquinone to a primary filter and a secondary filter to remove part of metal impurities, nonmetallic impurities and organic impurities;
s2: sending the filtered hydroquinone into an extraction tower A, an extraction tower B and an extraction tower C filled with an extracting agent, and carrying out three-stage countercurrent extraction to further remove metal impurities, nonmetallic impurities, organic impurities and water to obtain the hydroquinone.
The primary filter adopts ion exchange resin with the aperture of 0.5 mm.
The ion exchange resin is metal impurity adsorption resin; the preparation method comprises the following steps:
140kg of primary amino polymethacrylate resin, 6kg of dicyclopentenyl acrylic ester, 3kg of 3-methyl acrylamide dopamine, 4kg of tetramethylguanidine, 900kg of DMF (dimethyl formamide) and 45 ℃ are added into a reaction kettle, and the mixture is stirred for 140 minutes, filtered and dried to obtain the metal impurity adsorption resin.
The primary amino polymethacrylate resin is an acrylic acid ion exchange resin produced by Zhejiang light-striving industry Co., ltd, and the model is EA109F.
The secondary filter adopts a polysulfone microfiltration membrane with the pore diameter of 0.4 mu m.
And the extraction tower A, the extraction tower B and the extraction tower C are filled with an extractant, and the extractant is isopropyl ether.
The extraction temperature is 35 ℃.
The mass ratio of the extractant to the hydroquinone is 1:2.5.
example 4
The hydroquinone purifying and dewatering process includes the following steps:
s1: sending the crude hydroquinone to a primary filter and a secondary filter to remove part of metal impurities, nonmetallic impurities and organic impurities;
s2: sending the filtered hydroquinone into an extraction tower A, an extraction tower B and an extraction tower C filled with an extracting agent, and carrying out three-stage countercurrent extraction to further remove metal impurities, nonmetallic impurities, organic impurities and water to obtain the hydroquinone.
The primary filter adopts ion exchange resin with the aperture of 0.6 mm.
The ion exchange resin is metal impurity adsorption resin; the preparation method comprises the following steps:
150kg of primary amino polymethacrylate resin, 7kg of dicyclopentenyl acrylic ester, 4kg of 3-methacryloyl dopamine, 5kg of tetramethylguanidine and 1000kg of DMF are added into a reaction kettle, and the mixture is stirred for 150 minutes at 50 ℃, filtered and dried to obtain the metal impurity adsorption resin.
The primary amino polymethacrylate resin is acrylic acid ion exchange resin produced by Zhejiang light-striving industry Co., ltd, and the model is EA115F.
The secondary filter adopts a polyether sulfone microfiltration membrane with the pore diameter of 0.5 mu m.
And extracting agents are filled in the extracting tower A, the extracting tower B and the extracting tower C, and the extracting agents are acetophenone.
The extraction temperature is 40 ℃.
The mass ratio of the extractant to the hydroquinone is 1:3.
comparative example 1
The procedure of example 1 was followed except that no primary amine-based polymethacrylate resin was added during the preparation of the ion exchange resin.
Comparative example 2
The procedure of example 1 was followed except that dicyclopentenyl acrylate was not added during the preparation of the ion exchange resin.
Comparative example 3
3-Methacryldopamine was not added during the preparation of the ion exchange resin, otherwise the same as in example 1.
The hydroquinone purified and dehydrated in the above examples and comparative examples was evaluated by the following test method:
the water content is detected by adopting a 851 coulomb method card type water analyzer; metal ion detection was performed using agilent ICP-MS/MS 8900.
Table 1 test results
Through the data analysis of the above examples and comparative examples, the dicyclopentenyl/dopamine-based/adsorption resin of the present invention can improve the adsorption effect of the adsorption resin on metal impurities; the hydroquinone purifying and dehydrating method has the advantages of high extraction efficiency, high product purity, low water content and the like.
The above examples are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above examples, and any other changes, modifications, substitutions, combinations, and simplifications that do not depart from the spirit and principle of the present invention should be made in the equivalent manner, and the embodiments are included in the protection scope of the present invention.
Claims (4)
1. A method for purifying and dehydrating hydroquinone is characterized in that: the operation steps are as follows:
s1: sending the crude hydroquinone to a primary filter and a secondary filter to remove part of metal impurities, nonmetallic impurities and organic impurities; the primary filter adopts ion exchange resin with the aperture of 0.3-0.6 mm; the ion exchange resin is metal impurity adsorption resin; the preparation method comprises the following steps:
adding 100-150 parts by weight of primary amino polymethacrylate resin, 3-7 parts by weight of dicyclopentadienyl acrylate, 1-4 parts by weight of 3-methacryloyl dopamine, 2-5 parts by weight of tetramethylguanidine, 500-1000 parts by weight of DMF (dimethyl formamide), mixing at 40-50 ℃ for 100-150 minutes, filtering, and drying to obtain metal impurity adsorption resin; the primary amino polymethacrylate resin is acrylic acid ion exchange resin produced by Zhejiang light-striving industry Co., ltd, and the model is one of EA104F, EA109F, EA F;
s2: sending the filtered hydroquinone into an extraction tower A, an extraction tower B and an extraction tower C filled with an extracting agent, performing three-stage countercurrent extraction, and further removing metal impurities, non-metal impurities, organic impurities and water to obtain the hydroquinone, wherein the extracting agent is one or more of benzene, ethyl acetate, isopropyl ether, butyl acetate, trimethyl phosphate and acetophenone.
2. A process for purifying and dehydrating hydroquinone according to claim 1, characterized in that: the secondary filter adopts one or more of polypropylene microporous membrane, nylon 6 microporous membrane, nylon microporous membrane, polysulfone microporous membrane and polyether sulfone microporous membrane with the aperture of 0.1-0.5 mu m.
3. A process for purifying and dehydrating hydroquinone according to claim 1, characterized in that: in the step S2, the extraction temperature of the three-stage countercurrent extraction is 20-40 ℃.
4. A process for purifying and dehydrating hydroquinone according to claim 1, characterized in that: in the step S2, the mass ratio of the extractant to the hydroquinone is 1:0.8-3.
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| CN116283509A (en) * | 2023-03-31 | 2023-06-23 | 北京袭明科技有限公司 | Production method of electronic chemical hydroquinone |
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| GB811519A (en) * | 1956-06-29 | 1959-04-08 | Ilford Ltd | Improvements in or relating to the production of hydroquinone |
| US4119791A (en) * | 1977-09-14 | 1978-10-10 | The Goodyear Tire & Rubber Company | Aqueous recovery of hydroquinone |
| CN101479224A (en) * | 2006-06-29 | 2009-07-08 | 罗地亚管理公司 | Method for preparing purified hydroquinone and forming same |
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| CN116283509A (en) * | 2023-03-31 | 2023-06-23 | 北京袭明科技有限公司 | Production method of electronic chemical hydroquinone |
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