CN115322085B - Purification process for phenol acetone - Google Patents
Purification process for phenol acetone Download PDFInfo
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- CN115322085B CN115322085B CN202210799252.XA CN202210799252A CN115322085B CN 115322085 B CN115322085 B CN 115322085B CN 202210799252 A CN202210799252 A CN 202210799252A CN 115322085 B CN115322085 B CN 115322085B
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- 238000000746 purification Methods 0.000 title claims abstract description 25
- XDTRNDKYILNOAP-UHFFFAOYSA-N phenol;propan-2-one Chemical compound CC(C)=O.OC1=CC=CC=C1 XDTRNDKYILNOAP-UHFFFAOYSA-N 0.000 title claims abstract description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 172
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 88
- 239000007791 liquid phase Substances 0.000 claims abstract description 43
- 238000006243 chemical reaction Methods 0.000 claims abstract description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 239000011347 resin Substances 0.000 claims abstract description 11
- 229920005989 resin Polymers 0.000 claims abstract description 11
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 8
- 239000000047 product Substances 0.000 claims description 27
- 238000004523 catalytic cracking Methods 0.000 claims description 23
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 13
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical group CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 239000012670 alkaline solution Substances 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 8
- 239000006227 byproduct Substances 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012074 organic phase Substances 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 claims description 2
- 229940031826 phenolate Drugs 0.000 claims description 2
- 238000004064 recycling Methods 0.000 claims description 2
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 2
- 239000000463 material Substances 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 239000003513 alkali Substances 0.000 abstract description 8
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 22
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 20
- 239000003054 catalyst Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- -1 fluoroalkyl acrylate Chemical compound 0.000 description 9
- 238000007670 refining Methods 0.000 description 9
- 238000011084 recovery Methods 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006482 condensation reaction Methods 0.000 description 5
- 230000003068 static effect Effects 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 4
- 238000003421 catalytic decomposition reaction Methods 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- 238000007599 discharging Methods 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- MRIZMKJLUDDMHF-UHFFFAOYSA-N cumene;hydrogen peroxide Chemical compound OO.CC(C)C1=CC=CC=C1 MRIZMKJLUDDMHF-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DEQJNIVTRAWAMD-UHFFFAOYSA-N 1,1,2,4,4,4-hexafluorobutyl prop-2-enoate Chemical group FC(F)(F)CC(F)C(F)(F)OC(=O)C=C DEQJNIVTRAWAMD-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- JESIHYIJKKUWIS-UHFFFAOYSA-N 1-(4-Methylphenyl)ethanol Chemical compound CC(O)C1=CC=C(C)C=C1 JESIHYIJKKUWIS-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
-
- 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
- C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. cumene hydroperoxide
-
- 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
- C07C37/86—Purification; separation; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/85—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a purification process for phenol acetone, which belongs to the technical field of chemical synthesis, wherein a decomposed mixture enters a crude acetone tower, water is added, and a first liquid phase collected at the bottom of the crude acetone tower is collected; the first distillate component at the top of the crude acetone tower enters a refined acetone tower, alkali liquor is mixed, and a collected and purified acetone product is extracted from the lateral line at the upper part of the refined acetone tower; the first liquid phase enters a first fractionating tower, a first light component is collected at the top of the first fractionating tower, and tertiary amine is mixed with a second liquid phase collected at the bottom of the first fractionating tower to obtain a third liquid phase; the third liquid phase enters a crude phenol tower, a crude phenol product is extracted from the side line of the upper part of the crude phenol tower, the second light component is collected at the top of the crude phenol tower, the crude phenol component enters a second fractionating tower after passing through a resin reaction bed, the third light component is collected at the top of the second fractionating tower, the product extracted from the side line of the upper part of the second fractionating tower is a refined phenol product, and the first light component, the second light component and the third light component are recycled.
Description
Technical Field
The invention relates to the technical field of chemical synthesis, in particular to a purification process for phenol acetone.
Background
The production method of phenol comprises the following steps: the raw material cumene is oxidized into Cumene Hydroperoxide (CHP), and phenol and acetone are obtained by acid-catalyzed decomposition of the CHP under acidic conditions. In the oxidation reaction, due to the fact that the cumene hydroperoxide HAs poor thermal stability and can be automatically decomposed after being heated, side reactions are more, phenol and acetone are used as main components in acid decomposition products, a small amount of Hydroxyacetone (HA) is also contained in the decomposition products, the hydroxyacetone is colorless liquid, the boiling point is 145-146 ℃, the boiling point of phenol is 181.9 ℃, the boiling point of the two compounds is different by 37 ℃, the hydroxyacetone can be removed theoretically through fractional distillation, however, polar interaction exists between the hydroxyacetone and the phenol, and the hydroxyacetone is difficult to remove by adopting a common fractional distillation method.
Phenol is an important raw material in polycarbonate reaction, which requires high purity phenol, residual hydroxyacetone affects the purity of phenol, and in the prior art, CN 108602743B discloses a method of introducing 9 to 11 wt% of water into a crude product and reducing hydroxyacetone in phenol by using an azeotrope forming method, but the method requires an increased reboiling device, increases the amount of water, and also increases the subsequent wastewater treatment and device maintenance costs.
Disclosure of Invention
In order to solve the technical problems, the invention adopts the following technical scheme: the invention provides a purification process for phenol acetone, which comprises the following steps:
s1, acid catalytic decomposition: introducing the concentrated cumene hydroperoxide into a catalytic cracking reaction column, contacting with a catalyst in the catalytic cracking reaction column, performing catalytic cracking on the cumene hydroperoxide by the catalyst in the catalytic cracking reaction column to generate a mixture of phenol and acetone as a main product, discharging the mixture through the catalytic cracking reaction column, and separating and purifying;
preferably, the catalyst is one of a resin catalyst and a proton acid catalyst, and the resin catalyst specifically comprises: adopting a macroporous styrene ion exchange resin polymerization production process, adding (methyl) fluoroalkyl acrylate monomer and phenol to participate in polymerization, and then preparing the catalyst by sulfonation; the (methyl) acrylic acid fluoroalkyl ester monomer is hexafluorobutyl acrylate, dodecafluoroheptyl acrylate or tridecyl fluorooctyl acrylate; the protonic acid catalyst is sulfuric acid.
The hydrogen peroxide cumene is extremely easy to be converted into phenol and acetone under the catalysis of protonic acid or resin catalyst, the catalytic reaction is exothermic, the reaction rate is accelerated due to the temperature rise in the reaction process, the reaction temperature is increased, side reaction products are increased, for example, the reaction of the hydrogen peroxide cumene and the cumene generates dimethylbenzyl alcohol, the yield of the hydrogen peroxide cumene is influenced by acetophenone and methane, the subsequent purification reaction is also unfavorable, the temperature control of the reaction is important, and the catalytic cracking reaction is carried out at 70-90 ℃ and the reaction pressure is 70-95 kPa.
S2, the catalytic cracking reaction catalyzed by the protonic acid also comprises a neutralization step, and the catalytic reaction under the catalysis of the protonic acid needs to be neutralized in advance to reduce corrosion of acid on a reaction device and product loss for the subsequent reaction to be smoothly carried out; specifically, the mixed solution and the secondary amine neutralizer enter a first static mixer and are mixed until the pH value of a mixture system is 6-7; the secondary amine is one or more of diethylamine and piperidine.
S3, separating and purifying: s2, the mixture obtained in the step S1 enters a crude acetone tower, water is added, a first distillate component at the top of the crude acetone tower enters a refined acetone tower, and a first liquid phase at the bottom of the crude acetone tower is collected for purifying phenol; the first distillate component enters a refined acetone tower, alkaline solution is injected into the tower from the middle part of the refined acetone tower, aldehyde compounds in crude acetone are removed by condensation reaction, refining of acetone is achieved, the second distillate component at the top of the refined acetone tower is a purified acetone product, the fifth liquid phase at the bottom of the refined acetone tower is separated into liquid, the organic phase is distilled again to recover light components such as isopropylbenzene and the like and is used as a raw material, the alkaline solution is one or more of phenolate alkali solution, organic alkali or alkali metal hydroxide solution, the concentration of the alkaline solution is 1mol/L, the adding mass ratio of the alkaline solution is 0.1-0.3, and the adding mass ratio of water is 0.1-0.25. Preferably, the third distilled component collected from the upper side line of the refined acetone tower is transferred to the lower part of the refined acetone tower, enters the refined acetone tower from the lower side line and participates in the refining cycle again.
S4, a first liquid phase collected at the bottom of the crude acetone tower enters a first fractionating tower, cumene, alpha-methylstyrene and other first light components are collected at the top of the first fractionating tower, a second liquid phase collected at the bottom of the first fractionating tower, mixed tertiary amine enters a second static mixer to obtain a third liquid phase, the obtained third liquid phase enters the crude phenol tower, crude phenol products are collected at the upper side line of the crude phenol tower, a second light component is collected at the top of the crude phenol tower, residues collected at the bottom of the crude phenol tower are heavy components, heavy components enter a residue stripping tower and are removed as net residue byproducts, the crude phenol components collected at the upper side line of the crude phenol tower enter a second fractionating tower after passing through a resin reaction bed, the third light component remained in phenol is collected at the top of the second fractionating tower, refined phenol products are collected at the upper side line of the second fractionating tower, the fourth liquid phase at the bottom of the second fractionating tower enters the crude acetone tower to participate in circulation again, and the first, the first light components, the second light components and the third light components at the top of the first fractionating tower and the second fractionating tower are subjected to merging and alkaline washing and removing the residual phenol, and the acidic resin is recycled by the resin reaction bed.
In the experiment, in the step S4, the hydroxyacetone in the purified phenol is not obviously reduced under the condition of adding primary amine, the hydroxyacetone in the purified phenol is reduced under the condition of adding secondary amine as alkali, but the final aldehyde impurity is improved, the net result is that the purification of the phenol is unfavorable, the hydroxyacetone in the final product is obviously reduced under the condition of adding tertiary amine, and the treatment is simple, preferably, the tertiary amine is one or more of diisopropylethylamine, pyridine, tripropylamine, N-methylpiperidine and N, N-dimethylcyclohexylamine, and the mass adding ratio of the tertiary amine is 0.8-1.1.
The invention has the beneficial effects that: 1. according to the method, alkali liquor is introduced in the acetone refining process, and volatile aldehyde compounds are condensed with part of acetone by utilizing condensation reaction and are converted into substances which are not volatile, so that separation of the aldehyde compounds is realized, and refining and purifying of the acetone are realized; 2. in the invention, organic alkali is introduced in the purification process of phenol, and is mutually dissolved with a reaction system, so that the pH value of the reaction system is regulated; 3. the invention avoids generating aldehyde substances in the phenol refining process, and simultaneously, the hydroxyketone compounds in the phenol are greatly reduced, thereby realizing further purification and refining of the phenol; 4. the invention reduces the water consumption, reduces the post-treatment cost and reduces the maintenance cost of equipment.
Drawings
In order to more clearly illustrate the embodiments of the invention or the technical solutions in the prior art, the drawings that are required in the embodiments or the description of the prior art will be briefly described, it being obvious that the drawings in the following description are only some embodiments of the invention, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
Fig. 1 is a schematic diagram of a working flow of a purification process for phenol acetone according to an embodiment of the present invention.
Detailed Description
The following description of the embodiments of the present invention will be made clearly and fully with reference to the accompanying drawings, in which it is evident that the embodiments described are only some, but not all embodiments of the invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1:
the invention discloses a purification process for phenol acetone, which comprises the following steps of:
(1) Acid catalytic decomposition: introducing the concentrated cumene hydroperoxide into a catalytic cracking reaction column, contacting with a catalyst in the catalytic cracking reaction column, performing catalytic cracking on the cumene hydroperoxide by the catalyst in the catalytic cracking reaction column to generate a mixture of phenol and acetone as a main product, discharging the mixture through the catalytic cracking reaction column, and separating and purifying;
(2) And (3) separating and purifying: the mixture in the step (1) enters a crude acetone tower, water is added, the adding amount mass ratio of the water is 0.1, the water is favorable for volatilizing volatile components, a first distillate component at the top of the crude acetone tower is collected and sent into a refined acetone tower, meanwhile, phenol saline-alkali solution with the concentration of 1mol/L is injected into the tower from the middle part of the refined acetone tower, the phenol saline-alkali solution can be sodium phenolate, the adding mass ratio of the sodium phenolate is 0.3, the fractionation is carried out, aldehyde compounds in the crude acetone are removed by utilizing condensation reaction, the refining of the acetone is realized, a second distillate component at the top of the refined acetone tower is a purified acetone product, and a fifth liquid phase collected at the bottom of the refined acetone tower is distilled again for recovering light components such as isopropylbenzene; collecting a first liquid phase at the bottom of the crude acetone column for purification of phenol;
(3) The method comprises the steps that a first liquid phase at the bottom of a crude acetone tower enters a first fractionating tower, cumene, alpha-methylstyrene and other first light components are collected at the top of the first fractionating tower, a second liquid phase collected at the bottom of the first fractionating tower, mixed diisopropylethylamine enters a second static mixer, the mass addition ratio of diisopropylethylamine is 0.85, a third liquid phase is obtained, the third liquid phase enters the crude phenol tower, a crude phenol product is collected at the upper side of the crude phenol tower, a second light component is collected at the top of the crude phenol tower, residues collected at the bottom are heavy components, the heavy components enter a residue stripping tower and are removed as net residue byproducts, the crude phenol component collected at the upper side of the crude phenol tower enters a second fractionating tower after passing through a resin reaction bed, the third light component remained in phenol is collected at the top of the second fractionating tower, the refined phenol product is collected at the upper side of the second fractionating tower, the fourth liquid phase at the bottom of the third liquid phase is recycled into the acetone tower, the first light component, the second light component and the third light component at the top of the crude phenol tower are subjected to recycling, and the obtained after the residual phenol is subjected to alkaline removal, and the obtained residual phenol is recycled, and the purity is recovered: 99.35wt% and acetone product purity of 99.93wt%.
Example 2:
the invention discloses a purification process for phenol acetone, which comprises the following steps of:
(1) Acid catalytic decomposition: introducing the concentrated cumene hydroperoxide into a catalytic cracking reaction column, contacting with a catalyst in the catalytic cracking reaction column, performing catalytic cracking on the cumene hydroperoxide by the catalyst in the catalytic cracking reaction column to generate a mixture of phenol and acetone as a main product, discharging the mixture through the catalytic cracking reaction column, and separating and purifying;
(2) And (3) separating and purifying: the mixture in the step (1) enters a crude acetone tower, water is added, the adding amount mass ratio of the water is 0.15, the water is favorable for volatilizing volatile components, a first distillate component at the top of the crude acetone tower is collected and sent into a refined acetone tower, the first distillate component enters the refined acetone tower, caustic soda solution with the concentration of 1mol/L is injected into the tower from the middle part of the refined acetone tower, the adding mass ratio of caustic soda is 0.2, the fractionation is carried out, aldehyde compounds in the crude acetone are removed by utilizing condensation reaction, the refining of the acetone is realized, a second distillate component at the top of the refined acetone tower is a purified acetone product, and a fifth liquid phase collected at the bottom of the refined acetone tower is distilled again for recovering light components such as isopropylbenzene; collecting a first liquid phase at the bottom of the crude acetone column for purification of phenol;
(3) The method comprises the steps that a first liquid phase at the bottom of a crude acetone tower enters a first fractionating tower, cumene, alpha-methylstyrene and other first light components are collected at the top of the first fractionating tower, a second liquid phase collected at the bottom of the first fractionating tower, mixed pyridine enters a second static mixer, the mass addition ratio of pyridine is 0.92, a third liquid phase is obtained, the obtained third liquid phase enters the crude phenol tower, a crude phenol product is extracted from the upper side line of the crude phenol tower, a second light component is collected at the top of the crude phenol tower, residues collected at the bottom of the crude phenol tower are heavy components, the heavy components enter a residue stripping tower and are removed as clean residue byproducts, the crude phenol component extracted from the upper side line of the crude phenol tower enters a second fractionating tower after passing through a resin reaction bed, the third light component remained in phenol is collected at the top of the second fractionating tower, the upper side line of the second fractionating tower is extracted into a refined phenol product, the fourth liquid phase at the bottom of the second fractionating tower is recycled, the first light component, the second light component and the third light component at the top of the crude phenol tower undergo residual phenol and alkaline washing, and the obtained purity is recycled: 99.29wt% and the purity of the acetone product was 99.89wt%.
Example 3:
the invention discloses a purification process for phenol acetone, which comprises the following steps of:
(1) Acid catalytic decomposition: introducing the concentrated cumene hydroperoxide into a catalytic cracking reaction column, contacting with a catalyst in the catalytic cracking reaction column, performing catalytic cracking on the cumene hydroperoxide by the catalyst in the catalytic cracking reaction column to generate a mixture of phenol and acetone as a main product, discharging the mixture through the catalytic cracking reaction column, and separating and purifying;
(2) And (3) separating and purifying: the mixture in the step (1) enters a crude acetone tower, water is added, the adding amount mass ratio of the water is 0.25, the water is favorable for volatilizing volatile components, a first distillate component at the top of the crude acetone tower is collected and sent into a refined acetone tower, the first distillate component enters the refined acetone tower, sodium methoxide solution with the concentration of 1mol/L is injected into the tower from the middle part of the refined acetone tower, the adding mass ratio of sodium methoxide is 0.11, the fractionation is carried out, aldehyde compounds in the crude acetone are removed by utilizing condensation reaction, the refining of the acetone is realized, a second distillate component at the top of the refined acetone tower is a purified acetone product, and a fifth liquid phase collected at the bottom of the refined acetone tower is distilled again for recovering light components such as isopropylbenzene; collecting a first liquid phase at the bottom of the crude acetone column for purification of phenol;
(3) The method comprises the steps that a first liquid phase collected at the bottom of a crude acetone tower enters a first fractionating tower, cumene, alpha-methylstyrene and other first light components are collected at the top of the first fractionating tower, a second liquid phase collected at the bottom of the first fractionating tower, mixed N-methylpiperidine enters a second static mixer, the mass addition ratio of N-methylpiperidine is 1.1, a third liquid phase is obtained, the obtained third liquid phase enters a crude phenol tower, a crude phenol product is collected at the upper side of the crude phenol tower, a second light component is collected at the top of the crude phenol tower, residues collected at the bottom of the crude phenol tower are heavy components, the heavy components enter a residue stripping tower and are removed as net residue byproducts, the crude phenol component collected at the upper side of the crude phenol tower enters a second fractionating tower after passing through a resin reaction bed, the residual third light component in phenol is collected at the top of the second fractionating tower, a refined phenol product is collected at the upper side of the second fractionating tower, a fourth liquid phase at the bottom of the crude phenol tower is recovered, the first light components, the second light components and the third light components are subjected to alkaline recovery, and the obtained after the recovery of the crude phenol is subjected to alkaline recovery and the recovery, the recovery is subjected to the alkaline recovery and the recovery is subjected to the recovery of the purity: 99.15wt% and acetone product purity of 99.91wt%.
It will be apparent to those skilled in the art that various modifications and variations can be made to the present invention without departing from the spirit or scope of the invention. Thus, it is intended that the present invention also include such modifications and alterations insofar as they come within the scope of the appended claims or the equivalents thereof.
Claims (5)
1. A purification process for phenol and acetone is characterized by comprising the steps of purifying a mixture of phenol and acetone as a main product of cumene hydroperoxide through catalytic cracking reaction;
the purification of the acetone comprises the following steps: the mixture enters a crude acetone tower, water is added, and a first liquid phase collected at the bottom of the crude acetone tower is collected; the first distillate component at the top of the crude acetone tower enters a refined acetone tower, alkaline solution is injected into the refined acetone tower from the middle part of the refined acetone tower, and the second distillate component extracted from the lateral line at the upper part of the refined acetone tower is a purified acetone product;
the purification of phenol comprises: the first liquid phase collected at the bottom of the crude acetone tower enters a first fractionating tower, the top of the first fractionating tower collects a first light component, and the second liquid phase collected at the bottom of the first fractionating tower is mixed with tertiary amine to obtain a third liquid phase; the third liquid phase enters a crude phenol tower, a crude phenol product is extracted from the upper side line of the crude phenol tower, a second light component is collected at the top of the crude phenol tower, the crude phenol component enters a second fractionating tower after passing through a resin reaction bed, a third light component is collected at the top of the second fractionating tower, the product extracted from the upper side line of the second fractionating tower is a refined phenol product, and the first light component, the second light component and the third light component are recycled;
the concentration of the alkaline solution is 1mol/L, the adding mass ratio of the alkaline solution is 0.1-0.3, and the adding mass ratio of the water is 0.1-0.25;
the tertiary amine is diisopropylethylamine, pyridine, tripropylamine,N-methylpiperidine,N,N-one or more of dimethylcyclohexylamine;
the mass adding ratio of the tertiary amine is 0.8-1.1.
2. The purification process for phenol acetone of claim 1, wherein said acetone purification further comprises: and collecting a fifth liquid phase as a collection material at the bottom of the refined acetone tower, separating the fifth liquid phase, and distilling an organic phase to recover raw materials.
3. The purification process for phenol acetone according to claim 1 wherein said alkaline solution is one or more of a phenolate lye, an organic base or an alkali metal hydroxide solution.
4. A purification process for phenol acetone as defined in claim 1 wherein the residue collected at the bottom of said crude phenol column is a heavies which is fed to a residue stripper for removal as a net residue byproduct.
5. The purification process for phenol acetone of claim 1, wherein said purification of phenol further comprises: and collecting a fourth liquid phase at the bottom of the second fractionating tower, and recycling the fourth liquid phase into the crude acetone tower to participate in circulation again.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000086559A (en) * | 1998-09-11 | 2000-03-28 | Mitsubishi Chemicals Corp | Production of purified phenol |
| WO2005005357A1 (en) * | 2003-07-04 | 2005-01-20 | Ineos Phenol Gmbh & Co. Kg | Process for the preparation of phenolic compounds, for separating phenol from cleavage product mixtures, and an apparatus |
| JP2007269647A (en) * | 2006-03-30 | 2007-10-18 | Mitsubishi Chemicals Corp | METHOD FOR PURIFYING alpha-METHYLSTYRENE |
| WO2018088846A1 (en) * | 2016-11-14 | 2018-05-17 | 주식회사 엘지화학 | Method for purifying phenol |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE10060503A1 (en) * | 2000-12-06 | 2002-06-20 | Phenolchemie Gmbh & Co Kg | Method and device for the distillative workup of cleavage product mixtures which are obtained when alkylaryl hydroperoxides are cleaved |
| ES2545585T3 (en) * | 2007-12-20 | 2015-09-14 | Borealis Technology Oy | Phenol treatment |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000086559A (en) * | 1998-09-11 | 2000-03-28 | Mitsubishi Chemicals Corp | Production of purified phenol |
| WO2005005357A1 (en) * | 2003-07-04 | 2005-01-20 | Ineos Phenol Gmbh & Co. Kg | Process for the preparation of phenolic compounds, for separating phenol from cleavage product mixtures, and an apparatus |
| JP2007269647A (en) * | 2006-03-30 | 2007-10-18 | Mitsubishi Chemicals Corp | METHOD FOR PURIFYING alpha-METHYLSTYRENE |
| WO2018088846A1 (en) * | 2016-11-14 | 2018-05-17 | 주식회사 엘지화학 | Method for purifying phenol |
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