CN112500265A - Preparation method of diphenyl ether - Google Patents
Preparation method of diphenyl ether Download PDFInfo
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- CN112500265A CN112500265A CN202011506361.5A CN202011506361A CN112500265A CN 112500265 A CN112500265 A CN 112500265A CN 202011506361 A CN202011506361 A CN 202011506361A CN 112500265 A CN112500265 A CN 112500265A
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- Prior art keywords
- fixed bed
- bed reactor
- phenol
- reactor
- diphenyl ether
- Prior art date
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- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title abstract description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 45
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 17
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000010457 zeolite Substances 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000395 magnesium oxide Substances 0.000 claims abstract description 10
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000012299 nitrogen atmosphere Substances 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- 239000007788 liquid Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
- 239000000047 product Substances 0.000 description 32
- 239000002994 raw material Substances 0.000 description 25
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- ZCILODAAHLISPY-UHFFFAOYSA-N biphenyl ether Natural products C1=C(CC=C)C(O)=CC(OC=2C(=CC(CC=C)=CC=2)O)=C1 ZCILODAAHLISPY-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000010926 purge Methods 0.000 description 12
- 239000000463 material Substances 0.000 description 9
- 238000007599 discharging Methods 0.000 description 7
- 238000011049 filling Methods 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 238000005086 pumping Methods 0.000 description 7
- 238000004064 recycling Methods 0.000 description 7
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000013589 supplement Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003513 alkali Substances 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical group O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001502 supplementing effect Effects 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a preparation method of diphenyl ether, which adopts a continuous flow fixed bed reactor, wherein phenol contacts with a magnesium oxide/zeolite catalyst filled in the reactor in a nitrogen atmosphere environment and reacts to generate diphenyl ether.
Description
Technical Field
The invention belongs to the technical field of chemical industry, and particularly relates to a preparation method of diphenyl ether.
Background
The diphenyl ether is also called diphenyl ether, is an important chemical intermediate, can be used for producing flame retardant, essence, perfume, dye and the like, can also be used as a high-temperature heat carrier, and has wide application. The traditional biphenyl ether synthesis method is that chlorobenzene and phenol are condensed in caustic soda solution in the presence of copper oxide catalyst to obtain finished products, and the finished products are obtained through alkali washing and distillation refining.
CN102146024A discloses a preparation method of a diphenyl ether, which comprises the steps of generating a salt solution of phenol by using phenol and alkali, refluxing and removing water in a system by using chlorobenzene, and then carrying out U11mann reaction by dropwise adding chlorobenzene in the presence of a catalyst to generate a target compound; in the method, phenol is taken as a raw material and also taken as a solvent, a catalyst is copper sulfate pentahydrate or copper chloride wet material or a mixture of the copper sulfate pentahydrate and the copper chloride wet material, the whole process needs at least 12.5 hours, and the defects of long reaction time and complex process are overcome.
In view of the above, the invention provides the method for preparing the diphenyl ether, which is environment-friendly, simple in production process and low in production cost.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provide the preparation method of the diphenyl ether, which is environment-friendly, simple in production process and low in production cost.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
the invention provides a preparation method of diphenyl ether, which adopts a continuous flow fixed bed reactor, and phenol contacts with a magnesium oxide/zeolite catalyst filled in the reactor in a nitrogen atmosphere environment and reacts to generate diphenyl ether.
In some preferred embodiments of the present invention, the magnesium oxide/zeolite catalyst comprises 60 to 77% by mass of magnesium oxide and 23 to 40% by mass of zeolite.
As some preferred embodiments of the invention, the zeolite is a 4A zeolite.
As some preferred embodiments of the present invention, the phenol is preheated to 80-120 ℃ before entering the fixed bed reactor.
As some preferred embodiments of the present invention, the temperature in the reactor is 300 to 500 ℃ and the pressure is 0.05 to 0.2 MPa.
As some preferred embodiments of the present invention, the residence time of the phenol in the fixed reactor is 5 to 30 seconds.
As some preferred embodiments of the invention, the generated diphenyl ether, water and unreacted raw material phenol are discharged from the fixed bed reactor in a gaseous state, enter a multi-stage condenser to be cooled into liquid, then enter a rectifying still to be rectified and separated, the diphenyl ether is collected, and the unreacted phenol is recycled to the fixed bed reactor.
Adopt the produced beneficial effect of above-mentioned technical scheme to lie in:
the invention takes phenol as raw material, and biphenyl ether is prepared by high-temperature catalytic reaction and rectification separation of a fixed bed reactor.
The invention breaks the bottleneck in the prior art and fills the domestic blank.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention will be described in detail and fully with reference to the following embodiments.
Example 1
Opening a nitrogen purging pipeline and a fixed bed reactor to replace air in the nitrogen purging pipeline, preheating the raw material phenol to 100 ℃, pumping the mixture into a fixed bed reactor by a pump, filling a catalyst of magnesia (68 mass%)/4A zeolite (32 mass%), heating the fixed bed reactor to 400 ℃, controlling the pressure in the reactor to be 0.1MPa, adjusting the nitrogen flow to ensure that the material stays in the fixed bed reactor for 15 seconds, discharging the biphenyl ether, water and unreacted raw material phenol generated by the reaction out of the fixed bed reactor in a gaseous state, feeding the biphenyl ether, the water and the unreacted raw material phenol into a multistage condenser to be cooled into liquid, then the product enters a rectifying still for rectification separation, the collected water is used as circulating water for supplement, the phenol enters a reaction system again for recycling, the finished product enters a finished product large tank, and the purity of the finished product is 99.96 percent and the yield is 18.2 percent after the finished product is analyzed by gas chromatography.
Example 2
Opening a nitrogen purging pipeline and a fixed bed reactor to replace air in the nitrogen purging pipeline, preheating the raw material phenol to 120 ℃, pumping the mixture into a fixed bed reactor by a pump, filling a catalyst of magnesium oxide (60 mass%)/4A zeolite (40 mass%) in the fixed bed reactor, heating the fixed bed reactor to 500 ℃, controlling the pressure level in the reactor to be 0.2MPa, adjusting the nitrogen flow to ensure that the material stays in the fixed bed reactor for 5 seconds, discharging the biphenyl ether, water and unreacted raw material phenol generated by the reaction out of the fixed bed reactor in a gaseous state, feeding the biphenyl ether, the water and the unreacted raw material phenol into a multistage condenser to be cooled into liquid, then the product enters a rectifying still for rectification separation, the collected water is used as circulating water for supplement, the phenol enters a reaction system again for recycling, the finished product enters a finished product large tank, and the purity of the finished product is 99.98% and the yield is 13.9% after the finished product is analyzed by gas chromatography.
Example 3
Opening a nitrogen purging pipeline and a fixed bed reactor to replace air in the nitrogen purging pipeline, preheating the raw material phenol to 80 ℃, pumping into a fixed bed reactor by a pump, filling a catalyst of 77 mass percent/4A zeolite 23 mass percent in the fixed bed reactor, heating the fixed bed reactor to 300 ℃, controlling the pressure level in the reactor to be 0.05MPa, adjusting the nitrogen flow to ensure that the material stays in the fixed bed reactor for 30 seconds, discharging the biphenyl ether, water and unreacted raw material phenol generated by the reaction out of the fixed bed reactor in a gaseous state, feeding into a multistage condenser to be cooled into liquid, then the product enters a rectifying still for rectification separation, the collected water is used as circulating water for supplement, the phenol enters a reaction system again for recycling, the finished product enters a finished product large tank, and the purity of the finished product is 99.97 percent and the yield is 17.4 percent after the finished product is analyzed by gas chromatography.
Comparative example 1
Opening a nitrogen purging pipeline and a fixed bed reactor to replace air in the fixed bed reactor, preheating raw material phenol to 100 ℃, pumping the raw material phenol into the fixed bed reactor by a pump, filling a 4A zeolite catalyst in the fixed bed reactor, heating the fixed bed reactor to 400 ℃, controlling the pressure level in the reactor to be 0.1MPa, adjusting the flow of nitrogen to ensure that the retention time of the material in the fixed bed reactor is 15 seconds, discharging biphenyl ether, water and unreacted raw material phenol generated by reaction out of the fixed bed reactor in a gaseous state, feeding the biphenyl ether, the water and the unreacted raw material phenol into a multistage condenser to be cooled into liquid, feeding the liquid into a rectifying kettle to be rectified and separated, supplementing the collected water as circulating water, feeding the phenol into a reaction system again for recycling, feeding the finished product into a finished product large tank, analyzing the finished product by gas chromatography, wherein the.
Comparative example 2
Opening a nitrogen purging pipeline and a fixed bed reactor to replace air in the nitrogen purging pipeline, preheating the raw material phenol to 100 ℃, pumping the mixture into a fixed bed reactor by a pump, filling a tungsten oxide (77 mass%)/4A zeolite (23 mass%) catalyst in the fixed bed reactor, heating the fixed bed reactor to 400 ℃, controlling the pressure level in the reactor to be 0.1MPa, adjusting the nitrogen flow to ensure that the material stays in the fixed bed reactor for 15 seconds, discharging the biphenyl ether, water and unreacted raw material phenol generated by the reaction out of the fixed bed reactor in a gaseous state, feeding the biphenyl ether, the water and the unreacted raw material phenol into a multistage condenser to be cooled into liquid, then the product enters a rectifying still for rectification separation, the collected water is used as circulating water for supplement, the phenol enters a reaction system again for recycling, the finished product enters a finished product large tank, and the purity of the finished product is 99.96 percent and the yield is 9.3 percent through gas chromatography analysis.
Comparative example 3
Opening a nitrogen purging pipeline and a fixed bed reactor to replace air in the fixed bed reactor, preheating raw material phenol to 100 ℃, pumping the raw material phenol into the fixed bed reactor by a pump, filling a magnesium oxide catalyst in the fixed bed reactor, heating the fixed bed reactor to 400 ℃, controlling the pressure level in the reactor to be 0.1MPa, adjusting the nitrogen flow to ensure that the retention time of the material in the fixed bed reactor is 15 seconds, discharging biphenyl ether, water and unreacted raw material phenol generated by reaction out of the fixed bed reactor in a gaseous state, feeding the biphenyl ether, the water and the unreacted raw material phenol into a multistage condenser to be cooled into liquid, feeding the liquid into a rectifying kettle to be rectified and separated, supplementing the collected water as circulating water, feeding the phenol into a reaction system again for recycling, feeding the finished product into a finished product large tank, analyzing the finished product by gas chromatography, wherein the purity.
Comparative example 4
Opening a nitrogen purging pipeline and a fixed bed reactor to replace air in the nitrogen purging pipeline, preheating the raw material phenol to 100 ℃, pumping the mixture into a fixed bed reactor by a pump, filling a titanium oxide (77 mass%)/4A zeolite (23 mass%) catalyst in the fixed bed reactor, heating the fixed bed reactor to 400 ℃, controlling the pressure in the reactor to be 0.1MPa, adjusting the nitrogen flow to ensure that the material stays in the fixed bed reactor for 15 seconds, discharging the biphenyl ether, water and unreacted raw material phenol generated by the reaction out of the fixed bed reactor in a gaseous state, feeding the biphenyl ether, the water and the unreacted raw material phenol into a multistage condenser to be cooled into liquid, then the product enters a rectifying still for rectification separation, the collected water is used as circulating water for supplement, the phenol enters a reaction system again for recycling, the finished product enters a finished product large tank, and the purity of the finished product is 99.96 percent and the yield is 7.1 percent after the finished product is analyzed by gas chromatography.
Finally, it should be noted that: the above examples are only intended to illustrate the technical solution of the present invention, but not to limit it; although the present invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some technical features may be equivalently replaced; and such modifications or substitutions do not depart from the spirit and scope of the corresponding technical solutions of the embodiments of the present invention.
Claims (7)
1. A process for producing diphenyl ether, characterized in that a continuous flow fixed bed reactor is used, phenol is brought into contact with a magnesium oxide/zeolite catalyst packed in the reactor in a nitrogen atmosphere and reacted to produce diphenyl ether.
2. The process according to claim 1, wherein the amount of magnesium oxide in the magnesium oxide/zeolite catalyst is 60 to 77% by mass, and the amount of zeolite is 23 to 40% by mass.
3. The process according to claim 1, wherein said zeolite is a 4A zeolite.
4. The process according to claim 1, wherein said phenol is preheated to 80 to 120 ℃ before being fed into the fixed bed reactor.
5. The process according to claim 1, wherein the temperature in the reactor is 300 to 500 ℃ and the pressure in the reactor is 0.05 to 0.2 MPa.
6. The process according to claim 1, wherein the residence time of said phenol in said fixed reactor is 5 to 30 seconds.
7. The process for producing a diphenyl ether according to claim 1, wherein the produced diphenyl ether, water and unreacted raw phenol are discharged from the fixed bed reactor in a gaseous state, and are cooled to a liquid in a multistage condenser, and then the liquid is fed into a rectifying still to be rectified and separated, and the diphenyl ether is collected, and the unreacted phenol is recycled to the fixed bed reactor.
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5288922A (en) * | 1992-07-16 | 1994-02-22 | The Dow Chemical Company | Process of preparing diaryl ethers over a dealuminated zeolite catalyst |
JP2002138062A (en) * | 2000-10-31 | 2002-05-14 | Sumitomo Chem Co Ltd | Method for producing alkyl etherate of naphthol |
CN104364226A (en) * | 2012-05-31 | 2015-02-18 | 陶氏环球技术有限责任公司 | Catalytic dehydration of aryl alcohols to diaryl ethers |
WO2016187773A1 (en) * | 2015-05-25 | 2016-12-01 | 高化学株式会社 | Catalyst for preparing glycol ether and preparation method and application thereof |
CN109277114A (en) * | 2017-07-19 | 2019-01-29 | 中国科学院大连化学物理研究所 | The preparation method of catalyst for etherification and the method for producing methyl phenyl ethers anisole |
-
2020
- 2020-12-18 CN CN202011506361.5A patent/CN112500265B/en active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5288922A (en) * | 1992-07-16 | 1994-02-22 | The Dow Chemical Company | Process of preparing diaryl ethers over a dealuminated zeolite catalyst |
JP2002138062A (en) * | 2000-10-31 | 2002-05-14 | Sumitomo Chem Co Ltd | Method for producing alkyl etherate of naphthol |
CN104364226A (en) * | 2012-05-31 | 2015-02-18 | 陶氏环球技术有限责任公司 | Catalytic dehydration of aryl alcohols to diaryl ethers |
WO2016187773A1 (en) * | 2015-05-25 | 2016-12-01 | 高化学株式会社 | Catalyst for preparing glycol ether and preparation method and application thereof |
CN109277114A (en) * | 2017-07-19 | 2019-01-29 | 中国科学院大连化学物理研究所 | The preparation method of catalyst for etherification and the method for producing methyl phenyl ethers anisole |
Non-Patent Citations (1)
Title |
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黄亮 等: "甲醇脱水制二甲醚催化剂的研究", 《沈阳化工大学学报》 * |
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Address after: 056400 original steel mill, Dongxiang Village, Gengle Town, Shexian County, Handan City, Hebei Province Patentee after: Hebei Jindong Technology Group Co.,Ltd. Country or region after: China Address before: 056400 original steel mill, Dongxiang Village, Gengle Town, Shexian County, Handan City, Hebei Province Patentee before: SHEXIAN JINDONG ECONOMIC AND TRADE CO.,LTD. Country or region before: China |