CN107029692A - A kind of preparation method of ester exchange synthesizing diphenyl carbonate CNT Quito phase catalyst - Google Patents
A kind of preparation method of ester exchange synthesizing diphenyl carbonate CNT Quito phase catalyst Download PDFInfo
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- CN107029692A CN107029692A CN201610044541.3A CN201610044541A CN107029692A CN 107029692 A CN107029692 A CN 107029692A CN 201610044541 A CN201610044541 A CN 201610044541A CN 107029692 A CN107029692 A CN 107029692A
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- 239000003054 catalyst Substances 0.000 title claims abstract description 34
- 150000002148 esters Chemical group 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000004408 titanium dioxide Substances 0.000 claims abstract description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 13
- 235000011114 ammonium hydroxide Nutrition 0.000 claims abstract description 12
- 239000000654 additive Substances 0.000 claims abstract description 5
- 230000000996 additive effect Effects 0.000 claims abstract description 5
- 238000001914 filtration Methods 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 8
- 239000002243 precursor Substances 0.000 claims description 8
- 229910010413 TiO 2 Inorganic materials 0.000 claims description 7
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- FPCJKVGGYOAWIZ-UHFFFAOYSA-N butan-1-ol;titanium Chemical group [Ti].CCCCO.CCCCO.CCCCO.CCCCO FPCJKVGGYOAWIZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- 229910052719 titanium Inorganic materials 0.000 claims description 4
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 claims description 4
- -1 Isopropyl ester Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229910000349 titanium oxysulfate Inorganic materials 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- 239000002071 nanotube Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 41
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 15
- 239000002041 carbon nanotube Substances 0.000 abstract description 9
- 229910021393 carbon nanotube Inorganic materials 0.000 abstract description 9
- 238000011084 recovery Methods 0.000 abstract description 6
- 238000000926 separation method Methods 0.000 abstract description 4
- NHZZUJIRMHDTKR-UHFFFAOYSA-N carbonic acid;toluene Chemical compound OC(O)=O.CC1=CC=CC=C1 NHZZUJIRMHDTKR-UHFFFAOYSA-N 0.000 abstract description 3
- 238000005119 centrifugation Methods 0.000 abstract description 2
- 239000006185 dispersion Substances 0.000 abstract 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 14
- 230000003197 catalytic effect Effects 0.000 description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- 206010013786 Dry skin Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 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 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000007172 homogeneous catalysis Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 2
- 238000005832 oxidative carbonylation reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 231100000004 severe toxicity Toxicity 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- QNLVXLJTOLHAMA-UHFFFAOYSA-N N=NC=NN.N=NC=NN.C(O)(O)=O Chemical compound N=NC=NN.N=NC=NN.C(O)(O)=O QNLVXLJTOLHAMA-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- DWNAQMUDCDVSLT-UHFFFAOYSA-N diphenyl phthalate Chemical compound C=1C=CC=C(C(=O)OC=2C=CC=CC=2)C=1C(=O)OC1=CC=CC=C1 DWNAQMUDCDVSLT-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000007667 floating Methods 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 238000000703 high-speed centrifugation Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/18—Carbon
- B01J21/185—Carbon nanotubes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
- B01J35/396—Distribution of the active metal ingredient
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nanotechnology (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of preparation method of ester exchange synthesizing diphenyl carbonate with CNT Quito phase catalyst.The catalyst is using CNT as carrier, and titanium dioxide is active component；Prepared by additive of ammoniacal liquor.The technical scheme that the present invention is provided can make active component titania support carbon nano tube surface high degree of dispersion, the catalyst for titanium dioxide loaded on carbon nano tube of preparation, 49% phenol conversion and 49% ester exchange total recovery (methyl benzol carbonate and diphenyl carbonate total recovery), and preferably reusability can be reached.Particularly it is easy to separate from reaction system, separation and recovery can be realized, it is easy to scale application through filtering or short time centrifugation with autodeposition after completion of the reaction.
Description
Technical field
The present invention relates to a kind of preparation method of ester exchange synthesizing diphenyl carbonate with CNT Quito phase catalyst, specifically relate to
And the preparation side of a kind of dimethyl carbonate and phenol ester exchange synthesizing diphenyl carbonate catalyst for titanium dioxide loaded on carbon nano tube
Method.
Background technology
Diphenyl carbonate is a kind of important green chemical industry intermediate, is widely used in fine chemistry industry, medicine, agricultural chemicals and high score
The fields such as sub- material, the phosgene and bisphenol-A that can particularly substitute severe toxicity passes through the excellent poly- carbonic acid of melt transesterification synthesis performance
Ester.The synthetic method of diphenyl carbonate mainly has phosgenation, oxidative carbonylation and ester-interchange method.Phosgenation is due to raw material severe toxicity
And by-product hydrochloric acid has severe corrosive, the requirement of environmental protection is not met, is just gradually eliminated.Oxidative carbonylation is due to using
Expensive catalyst, catalytic efficiency is not high, and selectivity is relatively low, there is not yet industrialization report.Ester-interchange method cost of material,
Product yield, process safety in terms of environmental protection with having advantage, it is considered to be most potential green syt carbonic acid two
The method of phenyl ester.
At present, the ester exchange reaction of dimethyl carbonate and phenol reactant diphenyl carbonate synthesis uses organic titanium and organotin mostly
Class homogeneous catalysis system.The activity of homogeneous catalysis system is higher, but its separation and recovery difficulty with reactant mixture.In addition,
Organic titanium and organic tin compound are very sensitive to minor amount of water present in air and raw material, so as to limit their application.
Therefore, the heterogeneous catalytic system of this reaction is conducted extensive research both at home and abroad, such as metal oxide (Tong D S, et al.
J Mol Catal A：Chem, 2007,268：120-126), houghite (Mei F M, et al.Organic Process Research
＆development, 2004,8 (3)：372-275), heteropoly compound (CN191423476), molecular sieve (CN101412674)
And supported catalyst system (CN101254460).However, the above-mentioned heterogeneous catalytic system of document report exist catalytic activity compared with
Low, by-products content is higher, repeat performance is poor or the problems such as severe reaction conditions.
In recent years, Chen Tong etc. (CN102050740) is prepared for catalyst for titanium dioxide loaded on carbon nano tube, finds it to carbon
The ester exchange reaction of dimethyl phthalate and phenol has higher catalytic activity and selectivity, and shows preferable reusability.
However, the catalyst for titanium dioxide loaded on carbon nano tube that preparation is directly hydrolyzed with water easily forms stable hang with reactant
Floating body system, after completion of the reaction, it is necessary to which by prolonged high speed centrifugation, the separation of catalyst could be realized.
The content of the invention
The present invention is intended to provide a kind of dimethyl carbonate and phenol ester exchange synthesizing diphenyl carbonate CNT base heterogeneous catalysis
The preparation method of agent, make the catalyst of preparation have under relatively mild liquid-phase reaction condition high catalytic activity, high selectivity and
Good reusability, and be easy to separate from reaction system.
The concrete technical scheme of the present invention：Using CNT as carrier, titanium dioxide is active component, and ammoniacal liquor is additive system
It is standby.
The preparation method of CNT Quito of the present invention phase catalyst is as follows：
(1) it is CNT and ammoniacal liquor is scattered in ethanol；
(2) TiO 2 precursor is slowly added to, and is sufficiently stirred for making TiO 2 precursor slowly hydrolyze completely；
(3) through filtering or centrifuging, solids is after fully washing, in 100-300 DEG C of drying；
The volume ratio 3: 1000-10: 1000 of the ammoniacal liquor and ethanol, ammonia concn is 25-28%；
The TiO 2 precursor is butyl titanate, tetraethyl titanate, tetraisopropyl titanate, tetraphenyl titanate, tetrachloro
Change the one or more in titanium, titanyl sulfate.
The content of titanium dioxide is the 5-60% of titanium dioxide loaded on carbon nano tube gross mass in the catalyst；
The invention has the characteristics that：
(1) it is additive that the present invention adds ammoniacal liquor in preparation process, active component titanium dioxide is highly dispersed at carbon nanometer
Pipe carrier surface.
(2) catalyst for titanium dioxide loaded on carbon nano tube prepared by the present invention is synthesized for dimethyl carbonate with the ester exchange of phenol
The reaction of diphenyl carbonate, has high phenol conversion, high ester exchange selectivity and good under relatively mild liquid-phase reaction condition
Good reusability.49% phenol conversion and 49% ester exchange total recovery (methyl benzol carbonate and carbon can be achieved
Diphenyl phthalate total recovery).
(3) after the completion of ester exchange reaction, it is easy to after catalyst for titanium dioxide loaded on carbon nano tube reaction prepared by the present invention from anti-
Answer in system and separate, separation can be achieved, it is easy to scale application through filtering or short time centrifugation with autodeposition.
Embodiment
The present invention is further illustrated below by embodiment, but the implementation of the present invention is not limited to following examples：
Embodiment 1
1.2g CNT and 0.8ml concentration are dispersed in 180ml ethanol for 25-28% ammoniacal liquor agent.In lasting stirring
Under the conditions of, the 20ml ethanol solutions for containing 1.5ml butyl titanates are slowly added dropwise into the above-mentioned solution containing CNT.After
Continuous stirring reaction, makes tetrabutyl titanate hydrolysis complete.After the completion of reaction, through filtering, washing is obtained in 200 DEG C of dry 3h
To catalyst.
The catalyst that embodiment 2 is prepared with embodiment 1 carries out the ester exchange reaction of dimethyl carbonate and phenol
(1) in airway tube and thermometer, constant pressure funnel and there-necked flask equipped with rectifying column is connected with, embodiment is added
0.4 gram of 1 catalyst；
(2) it is passed through under nitrogen, adds 15 grams of phenol；
(3) when being heated to 176 DEG C, start that dimethyl carbonate is added dropwise, the total amount for adding dimethyl carbonate is 13.5ml.From
Start dropwise addition DMC and start timing, react 9.0 hours, methanol and dimethyl carbonate are constantly steamed by rectifying column in course of reaction
Mixed fraction；
(4) reaction solution of mixed fraction and methyl benzol carbonate containing principal product and diphenyl carbonate uses Shimadzu GC-14B types
Chromatographic, with correction normalizing standard measure.Reaction result is shown in Table 1.
Embodiment 3
The preparation process be the same as Example 1 of catalyst, but butyl titanate is replaced as TiO 2 precursor using titanium tetrachloride.System
Standby catalyst is used for the ester exchange reaction of dimethyl carbonate and phenol, and reaction condition is same as Example 2.Reaction result is shown in
Table 1.
Embodiment 4
The preparation process be the same as Example 1 of catalyst, but butyl titanate is replaced as TiO 2 precursor using titanyl sulfate.System
Standby catalyst is used for the ester exchange reaction of dimethyl carbonate and phenol, and reaction condition is same as Example 2.Reaction result is shown in
Table 1.
Embodiment 5
Catalyst prepared by embodiment 1 is used for the ester exchange reaction of dimethyl carbonate and phenol, except the reaction time is extended for
13.0 hours, other reaction condition be the same as Examples 2.Reaction result is shown in Table 1.
Embodiment 6
By the reacted catalyst of embodiment 2, cleaned with dimethyl carbonate, 200 DEG C of dryings are used further to the carbonic acid of next batch
The ester exchange reaction of dimethyl ester and phenol, reaction condition is same as Example 2.Realizing the circulation of catalyst as stated above makes
With the reaction result after recycling 4 times is shown in Table 1.
Comparative example 1
The preparation process be the same as Example 1 of catalyst, but ammoniacal liquor is replaced with deionized water.The catalyst of preparation is used for carbonic acid diformazan
The ester exchange reaction of ester and phenol, reaction condition is same as Example 2.Reaction result is shown in Table 1.
Comparative example 2
By the reacted catalyst of comparative example 1, cleaned with dimethyl carbonate, 200 DEG C of dryings are used further to the carbonic acid of next batch
The ester exchange reaction of dimethyl ester and phenol, reaction condition is same as Example 2.Reaction result is shown in Table 1.
Table 1
It was found from the result in table 1：The catalyst for titanium dioxide loaded on carbon nano tube prepared by additive of ammoniacal liquor is to carbonic acid two
The ester exchange reaction of methyl esters and phenol has high catalytic activity, high selectivity and preferable reusability；Replace existing with ammoniacal liquor
There is the deionized water used in technology, the activity and reusability of the catalyst of preparation are more preferably especially easily separated.
Claims (3)
1. a kind of ester exchange synthesizing diphenyl carbonate preparation method of CNT Quito phase catalyst, the catalysis
Agent is using CNT as carrier, and titanium dioxide is active component, it is characterised in that using ammoniacal liquor as additive,
Prepare in accordance with the following steps：
(1) CNT and ammoniacal liquor is scattered in ethanol, ammonia concn is 25-28%；
(2) titanium precursors are slowly added to, and are sufficiently stirred for making TiO 2 precursor slowly hydrolyze completely；
(3) through filtering or centrifuging, solids is after fully washing, in 100-300 DEG C of drying.
2. according to the method described in claim 1, it is characterised in that the content of titanium dioxide is carbon in catalyst
The 5-60% of nano tube supported titanium dioxide gross mass.
3. according to the method described in claim 1, it is characterised in that the volume ratio 3 of the ammoniacal liquor and ethanol:
1000-10∶1000；TiO 2 precursor can be butyl titanate, tetraethyl titanate, metatitanic acid four
Isopropyl ester, tetraphenyl titanate, titanium tetrachloride and titanyl sulfate.
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Cited By (2)
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| CN109675621A (en) * | 2017-10-19 | 2019-04-26 | 中国石油化工股份有限公司 | Composite catalyst preparation and application for diphenyl carbonate preparation |
| CN110642718A (en) * | 2019-09-06 | 2020-01-03 | 湖北三宁碳磷基新材料产业技术研究院有限公司 | Heterogeneous catalyst for synthesizing diphenyl carbonate and preparation method thereof |
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