CN116874355A - Method for reducing chromaticity of phenol/bisphenol A product - Google Patents
Method for reducing chromaticity of phenol/bisphenol A product Download PDFInfo
- Publication number
- CN116874355A CN116874355A CN202310748689.5A CN202310748689A CN116874355A CN 116874355 A CN116874355 A CN 116874355A CN 202310748689 A CN202310748689 A CN 202310748689A CN 116874355 A CN116874355 A CN 116874355A
- Authority
- CN
- China
- Prior art keywords
- product
- bisphenol
- phenol
- solution
- reducing
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 title claims abstract description 82
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 58
- 238000000034 method Methods 0.000 title claims abstract description 50
- 230000001603 reducing effect Effects 0.000 title claims abstract description 24
- 239000000047 product Substances 0.000 claims abstract description 147
- 239000012535 impurity Substances 0.000 claims abstract description 17
- 238000011282 treatment Methods 0.000 claims abstract description 17
- 229920000728 polyester Polymers 0.000 claims abstract description 13
- CLBRCZAHAHECKY-UHFFFAOYSA-N [Co].[Pt] Chemical compound [Co].[Pt] CLBRCZAHAHECKY-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000004737 colorimetric analysis Methods 0.000 claims abstract description 12
- 239000006227 byproduct Substances 0.000 claims abstract description 11
- 238000003756 stirring Methods 0.000 claims description 48
- 238000005406 washing Methods 0.000 claims description 47
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 38
- 239000012074 organic phase Substances 0.000 claims description 34
- 239000012071 phase Substances 0.000 claims description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 29
- 239000000126 substance Substances 0.000 claims description 25
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 24
- 238000010438 heat treatment Methods 0.000 claims description 22
- 239000008367 deionised water Substances 0.000 claims description 20
- 229910021641 deionized water Inorganic materials 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
- 239000003513 alkali Substances 0.000 claims description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 229930192627 Naphthoquinone Natural products 0.000 claims description 7
- BQPNUOYXSVUVMY-UHFFFAOYSA-N [4-[2-(4-diphenoxyphosphoryloxyphenyl)propan-2-yl]phenyl] diphenyl phosphate Chemical group C=1C=C(OP(=O)(OC=2C=CC=CC=2)OC=2C=CC=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 BQPNUOYXSVUVMY-UHFFFAOYSA-N 0.000 claims description 7
- 239000003638 chemical reducing agent Substances 0.000 claims description 7
- 238000001704 evaporation Methods 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- 150000002791 naphthoquinones Chemical class 0.000 claims description 7
- 230000007935 neutral effect Effects 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- 230000001590 oxidative effect Effects 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000012279 sodium borohydride Substances 0.000 claims description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 5
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000007259 addition reaction Methods 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 230000001105 regulatory effect Effects 0.000 claims description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 2
- 229920000402 bisphenol A polycarbonate polymer Polymers 0.000 claims description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 21
- 239000002994 raw material Substances 0.000 abstract description 9
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 76
- 239000002904 solvent Substances 0.000 description 12
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
- 238000005516 engineering process Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000006722 reduction reaction Methods 0.000 description 8
- 238000000926 separation method Methods 0.000 description 8
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 6
- 239000012467 final product Substances 0.000 description 6
- 239000011259 mixed solution Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 238000005809 transesterification reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 3
- 238000004042 decolorization Methods 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000011144 upstream manufacturing Methods 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 238000012696 Interfacial polycondensation Methods 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- BHIIGRBMZRSDRI-UHFFFAOYSA-N [chloro(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(Cl)OC1=CC=CC=C1 BHIIGRBMZRSDRI-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- -1 tetrachloro bisphosphonate Chemical compound 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LVFZOJGIHKBSNG-UHFFFAOYSA-N OP(OCl)(OCl)=O.OP(OCl)(OCl)=O Chemical compound OP(OCl)(OCl)=O.OP(OCl)(OCl)=O LVFZOJGIHKBSNG-UHFFFAOYSA-N 0.000 description 1
- 239000012327 Ruthenium complex Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- WGMBWDBRVAKMOO-UHFFFAOYSA-L disodium;4-[2-(4-oxidophenyl)propan-2-yl]phenolate Chemical compound [Na+].[Na+].C=1C=C([O-])C=CC=1C(C)(C)C1=CC=C([O-])C=C1 WGMBWDBRVAKMOO-UHFFFAOYSA-L 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000008236 heating water Substances 0.000 description 1
- 229910001701 hydrotalcite Inorganic materials 0.000 description 1
- 229960001545 hydrotalcite Drugs 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000011369 optimal treatment Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
- 239000002699 waste material Substances 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
- C07C37/01—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
- C07C37/055—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 the substituted group being bound to oxygen, e.g. ether group
- C07C37/0555—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 the substituted group being bound to oxygen, e.g. ether group being esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- 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
-
- 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
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 method for reducing chromaticity of phenol/bisphenol A products, which aims at the problem of higher chromaticity of products caused by higher content of colored impurities such as byproducts, industrial raw materials and the like in the existing phenol and bisphenol A downstream products; the final chromaticity of the final treatment product obtained by the invention can be judged by a platinum-cobalt colorimetric method, and the final chromaticity of the treated product is reduced to 0-20 ℃; the invention can be applied to most high polyester products to meet the requirements of low chromaticity and high purity of the products, has the advantages of low treatment cost, mild reaction condition, environmental friendliness and the like, and is a relatively excellent technical method for reducing the chromaticity of the products reported at present.
Description
Technical Field
The invention belongs to the field of polyester research, and particularly relates to a method for reducing chromaticity in a product taking phenol/bisphenol A as a raw material.
Background
Phenol and bisphenol a are widely used as important chemical raw materials in various fields such as biology, medicine, pesticide, materials and the like. The phenol can be used for producing phenolic resin, caprolactam, aniline, salicylic acid, synthetic rubber, synthetic fiber and the like, and can be also used for synthesizing bisphenol A, wherein bisphenol A is mainly formed by dehydration condensation of excessive phenol and acetone under the action of an acid catalyst in industrial production, and the bisphenol A can be used as a downstream product of phenol to further synthesize various polymer downstream products such as polycarbonate, epoxy resin, polysulfone resin, polyphenyl ether resin and the like, so as to synthesize high polymers and synthetic resin. Among these high polymer products using phenol and bisphenol A as raw materials, chromaticity is one of the very important indicators for judging the quality of the products, and the quality of the chromaticity directly affects the purity of the products.
The reason for the darker color of the downstream products of phenol and bisphenol A is mainly derived from the fact that bisphenol A produces a plurality of darker byproducts, such as benzoquinone, hydroquinone, quinone hydroquinone, catechol, and triphenols, in the synthesis process, and the darker color of the products represents higher content of byproducts and impurities in the products. Taking benzoquinone as an example, patent CN104030890 mentions that a water-soluble ruthenium complex is used as a catalyst, and the colorless hydroquinone is obtained by catalytic hydrogenation reduction of p-benzoquinone, but the factors such as higher catalyst cost and more severe reaction conditions are not considered. In the patent CN103570506, it is proposed to use a two-step method to oxidize and reflux phenol under the catalysis of hydrotalcite to collect terephthalquinone, and then to perform a reduction reaction on terephthalquinone and sodium metabisulfite to obtain colorless hydroquinone, but the problems of complex process flow, low conversion rate and the like are not considered, and complete decolorization cannot be achieved. Patent CN104557470 proposes that the oxidation slurry containing p-benzoquinone is sufficiently reacted with a sulfur-based reducing agent to obtain colorless hydroquinone, but the color of the sulfur-based reducing agent itself is not considered, and extraction and separation in the system are difficult, which affects the chromaticity of the original product.
Therefore, how to reduce the chromaticity of downstream products of phenol and bisphenol A is an important process in chemical synthesis, and the finally obtained products can be put into production and application after being refined and purified. For example, the traditional production method of bisphenol A in early stage is sulfuric acid method, mainly uses 73-74% sulfuric acid as catalyst, and has many problems of more colored byproducts, high material consumption ration, high labor intensity, difficult three-waste multiprocessing and the like. The bisphenol A hydrochloric acid process is to heat phenol, acetone and hydrochloric acid gas to react and then to obtain the adduct of phenol and bisphenol A through cold crystallization, and has the problems of long process flow, high equipment investment, long reaction time, high equipment corrosion resistance requirement and the like.
The conventional refining and purifying methods of bisphenol A downstream products comprise an adduct purifying method, a solvent extracting method, a recrystallization method and the like, for example, in patent CN108083987B, a mixed solution of toluene and water is heated and dissolved in crude bisphenol A, active bentonite is added, the mixture is stirred and filtered, an organic phase is separated, and the organic phase is concentrated and crystallized after being treated by macroporous adsorption resin to obtain ultra-high purity bisphenol A. In CN1717380 it is proposed to add phenol and a bisphenol-rich organic phase to an adduct crystallizer to form a crystalline adduct of phenol and bisphenol a. U.S. Pat. No.3326986 proposes the use of a chloride solvent to remove the isomeric dihydric phenols from the crystals by mixing the crude bisphenol A with water under heating to disperse it into an aqueous phase and a liquid organic phase. U.S. patent No.4740635 proposes heating a mixture of water and crude bisphenol a to melt, cooling it in an adiabatic environment by depressurizing it, and increasing its purity by washing the crystals multiple times. The method is mostly used for refining and removing raw phenol and other byproducts of phenols in the process flow of preparing bisphenol A from phenol, but unfortunately, the method has the problems of high energy consumption, environmental pollution and the like, the actual yield of bisphenol A and the yield optimization problem of bisphenol A in actual production are not considered while high-quality bisphenol A is obtained, and the method is only used for removing phenol substances in bisphenol A and upstream products thereof, and has no good removing effect on bisphenol A and other quinone substances in downstream products.
We have proposed a technique for reducing the colour of downstream products of phenol and bisphenol a which comprises the effect of removing bisphenol a and its upstream products as mentioned in the above patent, whilst also meeting the need for removal of other quinone species present in the synthesis of polyester from the downstream products of bisphenol a. Compared with the prior art, the method is only aimed at removing single phenolic substances, the method is more focused on removing the entirety of most phenolic colored impurities in operation, optimizes the operation flow, aims at removing various colored impurities possibly existing in the product more systematically, and can simultaneously take multiple times of removal of the phenolic substances in upstream and downstream products, so that the method has wide application scene and strong applicability. The invention mainly forms a complete set of product chromaticity treatment technology through the precise and efficient combination design of various operations such as solvent dissolution, chemical reaction, standing separation, physical adsorption and the like, not only the arrangement and combination of simple unit operations, but also the precise chemical reaction and effective reaction step design according to the colored substances actually existing in the product, and aims to reduce the problem of higher product chromaticity of raw materials or byproducts, such as color development and the like, caused by incomplete reaction in the product.
Disclosure of Invention
Aiming at the problem of higher product chromaticity caused by higher content of colored impurities such as byproducts, industrial raw materials and the like in the existing phenol and bisphenol A downstream products, the invention provides a technology capable of effectively reducing chromaticity, and the purposes of removing impurities, reducing product chromaticity and improving product purity are finally achieved mainly through various operations such as solvent dissolution, chemical reaction, standing separation, physical adsorption and the like.
The technical scheme of the invention is as follows:
a method for reducing the color of a phenol/bisphenol a product comprising the steps of:
(1) Dissolving the high polyester product by an organic solvent to obtain a product solution;
the organic solvent is selected from toluene, ethanol or acetone, preferably toluene; toluene is low in price and low in toxicity, most of polyester products can be effectively dissolved at normal temperature, and a product phase and a water phase can be effectively layered in the subsequent water washing operation, so that the separation is convenient; the high polyester product is effectively dissolved by the organic solvent, and the viscosity of the high polyester product is reduced so that the high polyester product is more easily subjected to decolorization reaction;
(2) Adding NaOH into the product solution in the step (1), and sufficiently stirring and alkali washing to enable bisphenol A and by-product phenol which are not completely reacted in the product to react with NaOH to generate soluble salts (sodium phenolate and bisphenol A sodium salt);
preferably, the alkaline washing operation is carried out at 0-80 ℃;
(3) Adding deionized water into the solution treated in the step (2), stirring and washing, separating an organic phase from a water phase by standing, and repeating the washing operation until the pH of the organic phase is neutral;
the water washing operation can be carried out at the temperature of 0-80 ℃, and the solubility of soluble salts and unreacted NaOH can be improved by heating the water washing;
(4) Adding hydrochloric acid into the solution treated in the step (3), and fully stirring to enable the color-developed benzoquinone and naphthoquinone substances in the product to undergo an addition reaction with the hydrochloric acid to generate phenolic substances; the reaction operation can be carried out at 0-80 ℃;
or, firstly, regulating the pH value of the solution treated in the step (3) to 1, and then adding a reducing agent to completely reduce the developed benzoquinone and naphthoquinone substances in the product into phenolic substances; the reducing agent is selected from hydrazine hydrate, sodium borohydride, potassium borohydride, sodium hydrosulfite, sodium bisulphite and the like, preferably sodium borohydride, and can be removed through water phase separation after full reduction reaction due to high solubility in water phase; during the reduction reaction, the reflux can be carried out under the protection of nitrogen atmosphere, so that the phenol obtained by reduction can be effectively prevented from being rapidly oxidized in the air;
or, adding an oxidant into the solution treated in the step (3) to completely oxidize the developed benzoquinone and naphthoquinone substances in the product into carboxylic acid substances; the oxidant is selected from H 2 O 2 、KMnO 4 、O 3 And the like, hydrogen peroxide is preferred, and residual impurities in the product solution do not influence the subsequent operation after the full oxidation reaction;
(5) Adding deionized water into the solution treated in the step (4), stirring and washing, separating an organic phase from a water phase by standing, and repeating the washing operation until the pH of the organic phase is neutral;
the water washing operation can be performed at 0-80deg.C, the solubility of phenols or carboxylic acids is improved by heating water washing, and the added chemical agent is removed;
(6) Adding NaOH into the solution treated in the step (5), and fully stirring and alkali washing;
(7) Adding deionized water into the solution treated in the step (6), stirring and washing, separating an organic phase from a water phase by standing, and repeating the washing operation until the pH of the organic phase is neutral;
the water washing operation can be carried out at the temperature of 0-80 ℃, and the solubility of soluble salts and unreacted NaOH can be improved by heating the water washing;
(8) Adding active carbon into the solution treated in the step (7), adsorbing insoluble impurities, and filtering to remove the active carbon and the insoluble impurities;
(9) Heating, stirring and evaporating the solution treated in the step (8) to dryness to obtain a final treatment product;
heating, stirring and evaporating to dryness can be performed under the oil bath condition of 80-120 ℃.
In the present invention, the high polyester-based products such as: bisphenol a-bis (diphenyl phosphate) (BDP), a typical downstream product of bisphenol a and phenol, is produced by a process that comprises three main steps, respectively: reacting phosphorus oxychloride with bisphenol A to obtain bisphenol A tetrachloro bisphosphonate, and then capping with phenol to obtain a final product BDP; after phosphorus oxychloride reacts with phenol to obtain diphenyl phosphoryl chloride, the diphenyl phosphoryl chloride reacts with bisphenol A to obtain BDP; carrying out end capping reaction on bisphenol A tetrachloro bisphosphate by using sodium phenolate to obtain BDP;
the high polyester products are also for example: bisphenol A polycarbonate, its main production process includes interfacial polycondensation phosgene method, traditional melt transesterification method and non-phosgene melt transesterification method; wherein, the interfacial polycondensation phosgene method is to react phosgene with sodium hydroxide aqueous solution of bisphenol A to generate micromolecular polycarbonate, and then further polycondensate into macromolecule; in the traditional melt transesterification method, phosgene and phenol are reacted to generate diphenyl carbonate, and the diphenyl carbonate is reacted with bisphenol A to generate polycarbonate; the non-phosgene melt transesterification method is to synthesize the polycarbonate with phenol by taking dimethyl carbonate as a raw material; the main byproduct obtained by transesterification and polycondensation in the reaction is phenol.
The final chromaticity of the final treatment product obtained by the invention can be judged by a platinum-cobalt colorimetric method, and the final chromaticity of the treated product is reduced to 0-20 ℃.
The technical principle of the invention is as follows:
the invention designs a technology for reducing chromaticity in phenol and bisphenol A and other phenol compound products. The complete product chromaticity treatment technology is formed mainly through the precise and efficient combination design of various operations such as solvent dissolution, chemical reaction, standing separation, physical adsorption and the like. According to the invention, the color materials actually existing in the product are subjected to accurate chemical reaction and effective reaction step design, so that the problem of high chromaticity of the product, such as raw material or byproduct color development and the like, caused by incomplete reaction in the product is solved.
The series connection of the operation steps defined by the invention has the unique limitation, has strict requirements on the arrangement of the operation sequences, firstly, selects a proper solvent according to the physical properties of specific products, and increases the dispersity of the solvent on the basis of not changing the properties of the original products so as to fully carry out subsequent reactions; secondly, chemically reacting phenolic substances with alkali through alkali washing, and removing soluble salts through the solubility of the phenolic substances; then further removing benzoquinone and naphthoquinone substances through addition reaction to generate phenols by acid washing, or fully reducing the quinone substances to the phenols by a reducing agent, or completely oxidizing the quinone substances to carboxylic acid substances by an oxidizing agent, wherein the step is an optimal treatment method which is selected practically aiming at impurities which are needed to be removed in the final product; finally, the phenol which has not been completely removed in the preceding step and which is newly formed in the reaction is sufficiently removed by alkali washing again. The operation is strictly arranged according to the operation steps, has strong pertinence to the removed colored impurities, and has universality and high efficiency compared with the existing single impurity treatment technology, thus having good application prospect.
The invention has the beneficial effects that:
according to the invention, through integrating, improving and optimizing the existing color removal technology, different chromaticity treatment technologies are regulated to aim at specific colored impurities without influencing the original product shape, unnecessary colored impurities can be directionally removed through the optimized combination of multiple processes, and on the basis of serial operation steps of the invention, single operation steps in the treatment process of the invention can be optimized through actual conditions, but the integral serial sequence of the treatment process cannot be changed. The chromaticity in the phenol products can be reduced to the greatest extent through the perfecting treatment of multiple processes, and impurities in the phenol products can be selectively removed, so that the optimal operation treatment required by the actual target products is achieved.
The invention can be applied to most high polyester products to meet the requirements of low chromaticity and high purity of the products. The technology used by the invention has the advantages of low treatment cost, low and easily available raw materials, mild reaction conditions, environmental friendliness and the like, and is a relatively excellent technical method for reducing the chromaticity of the product reported at present.
Detailed Description
The invention will be further illustrated by the following specific examples, although the scope of the invention is not limited thereto.
Example 1
This embodiment provides a technique for reducing the color of downstream products of phenol and bisphenol a, comprising the following steps:
(1) 30mL of bisphenol A bis (diphenyl phosphate) (BDP) is weighed as a bisphenol A downstream product in a 100mL beaker, a sample to be detected is detected to be a BDP product with the chromaticity of 90 degrees by a platinum cobalt colorimetric method, 30mL of toluene is poured into the BDP product as a solvent, and the BDP product is stirred at normal temperature until two phases are uniform.
(2) And (3) adding 40mL of NaOH solution with the concentration of 0.5g/100mL into the product solution of the step (1), fully stirring and washing with alkali, stirring for 1h at the normal temperature of 500r/min, standing until two phases are layered, and separating to obtain an organic phase.
(3) Adding 60mL of deionized water into the solution treated in the step (2), heating, stirring and washing for 30min at 80 ℃, standing until two phases are layered, separating to obtain an organic phase, and repeating the above operation for a plurality of times until the pH value in the product solution is reduced to 7.
(4) 2mL of 37wt.% HCl solution and 58mL of deionized water are added to the product solution of (3), the mixture is stirred for 1h at a speed of 500r/min at normal temperature, the mixture is stood until two phases are separated, and an organic phase is obtained by separation.
(5) Adding 60mL of deionized water into the solution treated in the step (4), heating, stirring and washing for 30min at 80 ℃, standing until two phases are layered, separating to obtain an organic phase, and repeating the above operation for a plurality of times until the pH value in the product solution is raised to 7.
(6) And (3) repeating the operation (2) and (3) on the product solution in the step (5) to wash the product solution once by alkali.
(7) Adding 0.5g of active carbon particles into the product solution of (6), and stirring and reacting for 1h at normal temperature and 500 r/min. The activated carbon particles are separated from the solution by filtration.
(8) And (3) heating and stirring the product solution treated in the step (7) at 80 ℃, evaporating the white mixed solution to be colorless and transparent, and detecting by a platinum-cobalt colorimetric method at the moment to obtain a final product with the chromaticity lower than 20 ℃.
Comparative example 1
This example proposes a technique for reducing the colour of the downstream products of phenol and bisphenol a, which differs from example 1 in that the pickling and alkaline washing operations in steps (2), (4) are exchanged, the specific steps being as follows:
(1) 30mL of bisphenol A bis (diphenyl phosphate) (BDP) is weighed as a bisphenol A downstream product in a 100mL beaker, a sample to be detected is detected to be a BDP product with the chromaticity of 90 degrees by a platinum cobalt colorimetric method, 30mL of toluene is poured into the BDP product as a solvent, and the BDP product is stirred at normal temperature until two phases are uniform.
(2) 2mL of 37wt.% HCl solution and 58mL of deionized water are added to the product solution of (1), the mixture is stirred for 1h at a speed of 500r/min at normal temperature, the mixture is left to stand until two phases are separated, and an organic phase is obtained by separation.
(3) Adding 60mL of deionized water into the solution treated in the step (2), heating, stirring and washing for 30min at 80 ℃, standing until two phases are layered, separating to obtain an organic phase, and repeating the above operation for a plurality of times until the pH value in the product solution is reduced to 7.
(4) And (3) adding 40mL of NaOH solution with the concentration of 0.5g/100mL into the product solution of the step (3), fully stirring and washing with alkali, stirring for 1h at the normal temperature of 500r/min, standing until two phases are layered, and separating to obtain an organic phase.
(5) Adding 60mL of deionized water into the solution treated in the step (4), heating, stirring and washing for 30min at 80 ℃, standing until two phases are layered, separating to obtain an organic phase, and repeating the above operation for a plurality of times until the pH value in the product solution is raised to 7.
(6) Adding 0.5g of active carbon particles into the product solution in the step (5), and stirring and reacting for 1h at the normal temperature of 500 r/min. The activated carbon particles are separated from the solution by filtration.
(7) And (3) heating and stirring the product solution treated in the step (6) at 80 ℃, wherein the product is a light yellow mixed solution, is evaporated to dryness and is light yellow transparent colloidal liquid, and the chromaticity of the product is 70 ℃ at the moment through detection by a platinum-cobalt colorimetric method, so that a good chromaticity reducing effect is not formed.
Example 2
This embodiment provides a technique for reducing the color of downstream products of phenol and bisphenol a, comprising the following steps:
(1) 30mL of bisphenol A bis (diphenyl phosphate) (BDP) was weighed as a bisphenol A downstream product in a 100mL beaker, 30mL of toluene was poured as a solvent, and the mixture was stirred at room temperature until the two phases were uniform.
(2) And (3) adding 40mL of NaOH solution with the concentration of 0.5g/100mL into the product solution of the step (1), fully stirring and washing with alkali, stirring for 1h at the normal temperature of 500r/min, standing until two phases are layered, and separating to obtain an organic phase.
(3) Adding 60mL of deionized water into the solution treated in the step (2), heating, stirring and washing for 30min at 80 ℃, standing until two phases are layered, separating to obtain an organic phase, and repeating the above operation for a plurality of times until the pH value in the product solution is reduced to 7.
(4) To the product solution of (3) was added 60mL of deionized water, and the pH was adjusted to 1 by adding HCl solution to the aqueous phase.
(5) And (3) adding 0.36g of sodium borohydride solid into the product solution in the step (4), flushing a sufficient amount of nitrogen, sealing, and stirring at normal temperature for reaction for 3 hours at 500 r/min.
(6) Adding 60mL of deionized water into the solution after the treatment in the step (5), heating, stirring and washing for 30min at 80 ℃, standing until two phases are layered, separating to obtain an organic phase, and repeating the above operation for a plurality of times until the sodium borohydride is completely washed off and the pH value is 7.
(7) And (3) repeating the operation (2) and (3) on the product solution in the step (6) to wash the product solution once by alkali.
(8) Adding 0.5g of active carbon particles into the product solution of (7), and stirring and reacting for 1h at normal temperature and 500 r/min. The activated carbon particles are separated from the solution by filtration.
(9) And (3) heating and stirring the product solution treated in the step (8) at 80 ℃, evaporating the white mixed solution to be transparent, and detecting by a platinum-cobalt colorimetric method at the moment to obtain a final product with the chromaticity lower than 20 ℃.
Comparative example 2
This comparative example is basically the same as example 2, except that:
and (3) deleting the repeated alkaline washing process in the step (7), keeping the rest operation steps unchanged, and after a single reduction step, regenerating a large amount of phenolic substances due to full reduction reaction, so that the treated product solution still presents a yellow transparent state, and determining the chromaticity of the treated product solution to be 95 ℃ through a platinum-cobalt colorimetric method.
Example 3
This embodiment provides a technique for reducing the color of downstream products of phenol and bisphenol a, comprising the following steps:
(1) 30mL of bisphenol A bis (diphenyl phosphate) (BDP) was weighed as a bisphenol A downstream product in a 100mL beaker, 30mL of toluene was poured as a solvent, and the mixture was stirred at room temperature until the two phases were uniform.
(2) And (3) adding 40mL of NaOH solution with the concentration of 0.5g/100mL into the product solution of the step (1), fully stirring and washing with alkali, stirring for 1h at the normal temperature of 500r/min, standing until two phases are layered, and separating to obtain an organic phase.
(3) Adding 60mL of deionized water into the solution treated in the step (2), heating, stirring and washing for 30min at 80 ℃, standing until two phases are layered, separating to obtain an organic phase, and repeating the above operation for a plurality of times until the pH value in the product solution is reduced to 7.
(4) To the product solution of (3) was added 60mL of deionized water, and the pH was adjusted to 1 by adding HCl solution to the aqueous phase.
(5) And (3) adding 0.36g of sodium dithionite solid into the product solution in the step (4), flushing a sufficient amount of nitrogen, sealing, and stirring at normal temperature for reaction for 3 hours at 500 r/min.
(6) Adding 60mL of deionized water into the solution after the treatment in the step (5), heating, stirring and washing for 30min at 80 ℃, standing until two phases are layered, separating to obtain an organic phase, and repeating the above operation for a plurality of times until the sodium dithionite is completely washed off and the pH value is 7.
(7) And (3) repeating the operation (2) and (3) on the product solution in the step (6) to wash the product solution once by alkali.
(8) Adding 0.5g of active carbon particles into the product solution of (7), and stirring and reacting for 1h at normal temperature and 500 r/min. The activated carbon particles are separated from the solution by filtration.
(9) And (3) heating and stirring the product solution treated in the step (8) at 80 ℃, evaporating the white mixed solution to be transparent, and detecting by a platinum-cobalt colorimetric method at the moment to obtain a final product with the chromaticity lower than 20 ℃.
Comparative example 3
This comparative example is basically the same as example 2, except that:
the operation sequence of the reduction in the step (5) is changed with that of the alkaline washing operation in the step (2), and the rest operation steps are kept unchanged, so that experimental results show that as the adjustment of the acidic pH is not carried out first, sodium dithionite reacts with phenol in the product to generate a large amount of benzenediol and benzoquinone, the evaporated solution is in a yellow turbid state, the platinum-cobalt colorimetric method is difficult to measure in the turbid state, and the original clear and transparent product state is destroyed.
Example 4
This embodiment provides a technique for reducing the color of downstream products of phenol and bisphenol a, comprising the following steps:
(1) 30mL of bisphenol A bis (diphenyl phosphate) (BDP) was weighed into a beaker as 100mL of bisphenol A downstream product, 30mL of toluene was poured in as solvent, and stirred at room temperature until the two phases were uniform.
(2) And (3) adding 40mL of NaOH solution with the concentration of 0.5g/100mL into the product solution of the step (1), fully stirring and washing with alkali, stirring for 1h at the normal temperature of 500r/min, standing until two phases are layered, and separating to obtain an organic phase.
(3) Adding 60mL of deionized water into the solution after the treatment in the step (2), heating, stirring and washing for 30min at 80 ℃, standing until two phases are layered, separating to obtain an organic phase, and repeating the above operation for a plurality of times until the pH value in the product solution is reduced to 7.
(4) 1mL of H was added to the product solution of (3) 2 O 2 Oxidant, stirring for 2h at normal temperature of 500r/min, and standing to twoThe phases are separated and the organic phase is obtained by separation.
(5) Adding 60mL of deionized water into the solution treated in the step (4), heating, stirring and washing at 80 ℃ for 30min, standing until two phases are layered, separating to obtain an organic phase, and repeating the above operation for H for a plurality of times 2 O 2 Completely washing off.
(6) And (3) repeating the operation (2) and (3) on the product solution in the step (5) to wash the product solution once by alkali.
(7) Adding 0.5g of active carbon particles into the product solution of (6), and stirring and reacting for 1h at normal temperature and 500 r/min. The activated carbon particles are separated from the solution by filtration.
(8) And (3) heating and stirring the product solution treated in the step (7) at 80 ℃, evaporating the white mixed solution to be colorless and transparent, and detecting by a platinum-cobalt colorimetric method at the moment to obtain a final product with the chromaticity lower than 20 ℃.
Claims (6)
1. A method for reducing the color of a phenol/bisphenol a product comprising the steps of:
(1) Dissolving the high polyester product by an organic solvent to obtain a product solution;
(2) Adding NaOH into the product solution in the step (1), and fully stirring and alkali washing to enable bisphenol A and byproduct phenol which are not completely reacted in the product to react with NaOH to generate soluble salt;
(3) Adding deionized water into the solution treated in the step (2), stirring and washing, separating an organic phase from a water phase by standing, and repeating the washing operation until the pH of the organic phase is neutral;
(4) Adding hydrochloric acid into the solution treated in the step (3), and fully stirring to enable the color-developed benzoquinone and naphthoquinone substances in the product to undergo an addition reaction with the hydrochloric acid to generate phenolic substances;
or, firstly, regulating the pH value of the solution treated in the step (3) to 1, and then adding a reducing agent to completely reduce the developed benzoquinone and naphthoquinone substances in the product into phenolic substances;
or, adding an oxidant into the solution treated in the step (3) to completely oxidize the developed benzoquinone and naphthoquinone substances in the product into carboxylic acid substances;
(5) Adding deionized water into the solution treated in the step (4), stirring and washing, separating an organic phase from a water phase by standing, and repeating the washing operation until the pH of the organic phase is neutral;
(6) Adding NaOH into the solution treated in the step (5), and fully stirring and alkali washing;
(7) Adding deionized water into the solution treated in the step (6), stirring and washing, separating an organic phase from a water phase by standing, and repeating the washing operation until the pH of the organic phase is neutral;
(8) Adding active carbon into the solution treated in the step (7), adsorbing insoluble impurities, and filtering to remove the active carbon and the insoluble impurities;
(9) And (3) heating, stirring and evaporating the solution treated in the step (8) to dryness to obtain a final treatment product.
2. The method for reducing the color of a phenol/bisphenol a product of claim 1, wherein the organic solvent is selected from the group consisting of toluene, ethanol and acetone in step (1).
3. The method for reducing the color of a phenol/bisphenol a product of claim 1, wherein in step (4), the reducing agent is selected from the group consisting of hydrazine hydrate, sodium borohydride, potassium borohydride, sodium dithionite and sodium bisulfite.
4. The method for reducing the color of a phenol/bisphenol A product of claim 1 wherein in step (4) the oxidizing agent is selected from the group consisting of H 2 O 2 、KMnO 4 Or O 3 。
5. The method of reducing the color of a phenol/bisphenol a product of claim 1 wherein the high polyester product is bisphenol a-bis (diphenyl phosphate) or bisphenol a polycarbonate.
6. The method for reducing the color of a phenol/bisphenol a product of claim 1, wherein the final treated product is judged to have a final color by a platinum cobalt colorimetry method, and the final color of the treated product is reduced to 0-20 degrees.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310748689.5A CN116874355A (en) | 2023-06-25 | 2023-06-25 | Method for reducing chromaticity of phenol/bisphenol A product |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310748689.5A CN116874355A (en) | 2023-06-25 | 2023-06-25 | Method for reducing chromaticity of phenol/bisphenol A product |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116874355A true CN116874355A (en) | 2023-10-13 |
Family
ID=88265300
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310748689.5A Pending CN116874355A (en) | 2023-06-25 | 2023-06-25 | Method for reducing chromaticity of phenol/bisphenol A product |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116874355A (en) |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0420523A (en) * | 1990-05-16 | 1992-01-24 | Nippon G Ii Plast Kk | Production of polycarbonate |
| CN1145352A (en) * | 1995-08-14 | 1997-03-19 | 拜尔公司 | Process for purification of bisphenol |
| CN106496264A (en) * | 2016-09-27 | 2017-03-15 | 浙江万盛股份有限公司 | A kind of bisphenol-A is double（Diphenyl phosphoester）Continuous preparation method |
| JP2020152650A (en) * | 2019-03-18 | 2020-09-24 | 三菱ケミカル株式会社 | Method for producing bisphenol, and method for producing polycarbonate resin |
| CN114292293A (en) * | 2021-12-30 | 2022-04-08 | 山东旭锐新材有限公司 | Washing process for BDP industrial production |
| WO2022121245A1 (en) * | 2020-12-07 | 2022-06-16 | 浙江万盛股份有限公司 | Continuous industrial production method for high-purity bisphenol a-bis(diphenyl phosphate) |
| JP2022103564A (en) * | 2020-12-28 | 2022-07-08 | 三菱ケミカル株式会社 | Method for producing bisphenol a, and method for producing polycarbonate resin |
| CN115028659A (en) * | 2022-07-14 | 2022-09-09 | 宿迁联盛科技股份有限公司 | Bisphenol A-bis (diphenyl phosphate) and preparation process thereof |
| JP2023006817A (en) * | 2021-06-30 | 2023-01-18 | 三菱ケミカル株式会社 | Method for producing bisphenol and method for producing polycarbonate resin |
-
2023
- 2023-06-25 CN CN202310748689.5A patent/CN116874355A/en active Pending
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0420523A (en) * | 1990-05-16 | 1992-01-24 | Nippon G Ii Plast Kk | Production of polycarbonate |
| CN1145352A (en) * | 1995-08-14 | 1997-03-19 | 拜尔公司 | Process for purification of bisphenol |
| CN106496264A (en) * | 2016-09-27 | 2017-03-15 | 浙江万盛股份有限公司 | A kind of bisphenol-A is double（Diphenyl phosphoester）Continuous preparation method |
| JP2020152650A (en) * | 2019-03-18 | 2020-09-24 | 三菱ケミカル株式会社 | Method for producing bisphenol, and method for producing polycarbonate resin |
| WO2022121245A1 (en) * | 2020-12-07 | 2022-06-16 | 浙江万盛股份有限公司 | Continuous industrial production method for high-purity bisphenol a-bis(diphenyl phosphate) |
| JP2022103564A (en) * | 2020-12-28 | 2022-07-08 | 三菱ケミカル株式会社 | Method for producing bisphenol a, and method for producing polycarbonate resin |
| JP2023006817A (en) * | 2021-06-30 | 2023-01-18 | 三菱ケミカル株式会社 | Method for producing bisphenol and method for producing polycarbonate resin |
| CN114292293A (en) * | 2021-12-30 | 2022-04-08 | 山东旭锐新材有限公司 | Washing process for BDP industrial production |
| CN115028659A (en) * | 2022-07-14 | 2022-09-09 | 宿迁联盛科技股份有限公司 | Bisphenol A-bis (diphenyl phosphate) and preparation process thereof |
Non-Patent Citations (1)
| Title |
|---|
| 张蓓: ""磷酸酯类成核剂NA-11、阻燃剂BDP和RDP的合成研究"", 中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑, no. 4, 15 April 2009 (2009-04-15), pages 016 - 148 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN108101850B (en) | Method for improving quality of 5-acetoacetylaminobenzimidazolone | |
| JP5030472B2 (en) | Manufacturing method and manufacturing equipment of high purity bisphenol A | |
| CN104592063A (en) | Environment-friendly production process of H acid | |
| CN110467552B (en) | Synthesis method of bisphenol S | |
| CN104693081B (en) | Method for refining bisphenol S by using mixed solvent | |
| CN111233644B (en) | Synthesis and extraction method of adamantanone | |
| KR20010085545A (en) | Process for recovering catalyst transition metals from salt-containing reaction mixtures | |
| CN116874355A (en) | Method for reducing chromaticity of phenol/bisphenol A product | |
| CN111825532A (en) | Preparation method of 4-hydroxybiphenyl | |
| CN111620761A (en) | Synthesis method of 2, 6-dihydroxytoluene | |
| CN109665995B (en) | Refining method of caprolactam crude product and preparation method of caprolactam | |
| CN114605276A (en) | Preparation method of glycine | |
| CN113248356B (en) | Industrial production method of 4-hydroxy-1-indanone | |
| CN108658901A (en) | A kind of method for optical resolution of DL- pantolactones | |
| CN109456172B (en) | Method for purifying dodecanedioic acid in water phase | |
| CN107827821B (en) | Continuous flow clean production process of pyrazolone series products | |
| CN107915343B (en) | Process wastewater treatment process in production process of pyrazolone series products | |
| KR100425646B1 (en) | Method of preparing 4,4'-biphenol | |
| CN113461511B (en) | Preparation method of 1, 4-naphthalenedicarboxylic acid | |
| CN111087373A (en) | Method for preparing vitamin C by acid method | |
| JPS6136A (en) | Production of 2,6-di-tert.-butylphenol | |
| CN113683495B (en) | Method for preparing 4,4' -dihydroxybenzophenone | |
| CN115650889B (en) | Synthesis method of high-purity low-chroma 4, 4' -dihydroxydiphenyl sulfone | |
| CN108752180B (en) | Method for preparing 1-chloroanthraquinone by direct chlorination of photocatalytic chlorine | |
| JP2002187862A (en) | Tetramethylbisphenol f, method for producing the same and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |