CN101033177A - Method of synthesizing 2-ethoxy-phenol - Google Patents
Method of synthesizing 2-ethoxy-phenol Download PDFInfo
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- CN101033177A CN101033177A CN 200710021424 CN200710021424A CN101033177A CN 101033177 A CN101033177 A CN 101033177A CN 200710021424 CN200710021424 CN 200710021424 CN 200710021424 A CN200710021424 A CN 200710021424A CN 101033177 A CN101033177 A CN 101033177A
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- ethoxy
- pyrocatechol
- phenol
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- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims abstract description 13
- MOEFFSWKSMRFRQ-UHFFFAOYSA-N 2-ethoxyphenol Chemical compound CCOC1=CC=CC=C1O MOEFFSWKSMRFRQ-UHFFFAOYSA-N 0.000 title claims description 41
- 238000006243 chemical reaction Methods 0.000 claims abstract description 59
- 239000003054 catalyst Substances 0.000 claims abstract description 39
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000002994 raw material Substances 0.000 claims abstract description 30
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims abstract description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 5
- 229910002651 NO3 Inorganic materials 0.000 claims abstract description 5
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 5
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 5
- 229910052804 chromium Inorganic materials 0.000 claims abstract description 5
- 229910052802 copper Inorganic materials 0.000 claims abstract description 5
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 5
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 5
- 150000003624 transition metals Chemical class 0.000 claims abstract description 5
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 5
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 112
- PHFQLYPOURZARY-UHFFFAOYSA-N chromium trinitrate Chemical group [Cr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PHFQLYPOURZARY-UHFFFAOYSA-N 0.000 claims description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 6
- 239000002808 molecular sieve Substances 0.000 claims description 5
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 5
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 239000004411 aluminium Substances 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052728 basic metal Inorganic materials 0.000 claims description 4
- 150000003818 basic metals Chemical class 0.000 claims description 4
- 239000011651 chromium Substances 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 229910052742 iron Inorganic materials 0.000 claims description 4
- -1 plumbous Chemical compound 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 3
- 239000002253 acid Substances 0.000 abstract 2
- 230000001131 transforming effect Effects 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 229910052593 corundum Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052745 lead Inorganic materials 0.000 abstract 1
- 229910001845 yogo sapphire Inorganic materials 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 28
- 230000009466 transformation Effects 0.000 description 26
- 238000011156 evaluation Methods 0.000 description 24
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XTVVROIMIGLXTD-UHFFFAOYSA-N copper(II) nitrate Chemical compound [Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O XTVVROIMIGLXTD-UHFFFAOYSA-N 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 239000011133 lead Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 235000010333 potassium nitrate Nutrition 0.000 description 3
- 239000004323 potassium nitrate Substances 0.000 description 3
- 230000002152 alkylating effect Effects 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 2
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000007036 catalytic synthesis reaction Methods 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- MVFCKEFYUDZOCX-UHFFFAOYSA-N iron(2+);dinitrate Chemical compound [Fe+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O MVFCKEFYUDZOCX-UHFFFAOYSA-N 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- RLJMLMKIBZAXJO-UHFFFAOYSA-N lead nitrate Chemical compound [O-][N+](=O)O[Pb]O[N+]([O-])=O RLJMLMKIBZAXJO-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
- 239000011654 magnesium acetate Substances 0.000 description 1
- 235000011285 magnesium acetate Nutrition 0.000 description 1
- 229940069446 magnesium acetate Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000007715 potassium iodide Nutrition 0.000 description 1
- 229960004839 potassium iodide Drugs 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
This invention relates to a method for synthesizing phthal eather by solid-gas reaction in continuous flow of diatol and oxophenic acid, in which, alkali metal, alkaline earth or transition metal such as nitrate, carbonate, aectic acetate or halid of Ni, Pb, Zn, Cu, Al and Cr are taken as the active components and active Al2O3, active carbon or NaY molecular screen as the carrier to form a load catalyst used in synthesizing phthal eather in a given experiment condition, which can get good transforming rate of raw material and selectivity of aimed products, in which, the transforming rate of oxophenic acid can reach to 100% and the selectivity of phthal eather can reach to 91%.
Description
Technical field
The present invention relates to the method for a kind of synthesizing 2-ethoxy-phenol among the organic chemical industry, provide the method for a kind of environmental friendliness, low pollution, efficient synthesizing 2-ethoxy-phenol specifically.
Background technology
2-ethoxy-phenol is important fine-chemical intermediate, is widely used in the synthetic of medicine, spices and dyestuff, and especially the industry of vanirone is synthetic.At present, the method for producing 2-ethoxy-phenol adopts homogeneous phase, interrupter method to carry out more, and monobromethane, monochloroethane are main ethylization reagent.These ethylization reagent have stronger toxicity and corrodibility, need numerous and diverse operation to handle.In addition, the waste liquid that produces in the reaction process and not the ethylization reagent serious environment pollution of complete reaction.For fear of these shortcomings, we have carried out gas-solid phase catalytic synthesis, adopt non-toxicity and non-corrosive diethyl carbonate and pyrocatechol reaction synthesizing 2-ethoxy-phenol.Diethyl carbonate (Diethyl Carbonate, vehicle economy C) is the important substance in the carbonic ether, and molecular formula is C
5H
10O
3, structural formula is (C
2H
5O)
2C=O, DEC are the colourless liquid that peat-reek is arranged at normal temperatures, contain ethyl, oxyethyl group, carbonyl and carbonyl oxyethyl group in the molecular structure of DEC, can with reactions such as alcohol, phenol, amine, ester, be important organic synthesis intermediate, have very high industrial value.Even diethyl carbonate is discharged in the environment, also only can slowly resolve into non-toxic and non-pollution ethanol and carbonic acid gas.The chemical of USEPA is with reference to pointing out: diethyl carbonate (CAS#105-58-8) is not also found environmental problem in existing resource of information.
Summary of the invention
Purpose of the present invention just provides the method for a kind of environmental friendliness, low pollution, efficient synthesizing 2-ethoxy-phenol.Be exactly specifically with the green chemical diethyl carbonate be alkylating reagent with pyrocatechol at gas-solid one-step synthesis in the continuous flow reaction unit mutually.Catalyzer of the present invention is that nitrate, carbonate, acetate, oxyhydroxide or the halogenide with basic metal, alkaline-earth metal or transition metal such as nickel, lead, zinc, copper, aluminium, iron, chromium is active ingredient, is the loaded catalyst of carrier with activated alumina, gac or NaY molecular sieve.
Purpose of the present invention realizes according to following proposal:
The method for preparing the synthesizing 2-ethoxy-phenol loaded catalyst is: at first nitrate, carbonate, acetate, oxyhydroxide or the halogenide with basic metal, alkaline-earth metal or transition metal such as nickel, lead, zinc, copper, aluminium, iron, chromium is made into the solution identical with carrier bulk, activated alumina, gac or NaY molecular sieve with certain particle size (20～80 order) under condition of stirring add wherein, put into vacuum drier flood after 12～24 hours take out 120～150 ℃ dry 4～10 hours down, standby.
Above-mentioned preparation loaded catalyst is that active ingredient is better with the chromium nitrate effect.
Above-mentioned loaded catalyst charge capacity is 1%～20% of a catalyst quality, and is wherein better with 15% effect.
Building-up reactions is carried out on continuous fixed bed reactor, and temperature of reaction is 250～380 ℃, and is wherein better with 330 ℃ of following effects.The mol ratio of raw material pyrocatechol and diethyl carbonate is 1: 2.5～1: 6, and is wherein better with 1: 4 effect.
The present invention compared with prior art advantage is the raw material low toxicity, and Preparation of Catalyst is simple, easily row, and selectivity and transformation efficiency are all higher, and product postprocessing is convenient.Use the green chemical diethyl carbonate as alkylating reagent and pyrocatechol at gas-solid synthesizing 2-ethoxy-phenol in the continuous flow reaction unit mutually, wherein the pyrocatechol transformation efficiency can reach 100%, the 2-ethoxy-phenol selectivity is up to 91%.
Embodiment
The negative supported catalyst of synthesizing 2-ethoxy-phenol prepares as follows in following examples:
At first nitrate, carbonate, acetate, oxyhydroxide or the halogenide with basic metal, alkaline-earth metal or transition metal such as nickel, lead, zinc, copper, aluminium, iron, chromium is made into the solution identical with carrier bulk, and the loaded catalyst charge capacity is 1%～20% of a catalyst quality.Under condition of stirring, the activated alumina of certain particle size (20～80 order), gac or NaY molecular sieve are added wherein, put into vacuum drier flood take out after 12～24 hours 120～150 ℃ dry 4～10 hours down, standby.
Embodiment 1
With 15% activated alumina load saltpetre is that catalyzer carries out the catalyst activity evaluation on continuous fixed bed reactor, reaction conditions is as follows: 350 ℃ of temperature of reaction, proportioning raw materials (pyrocatechol: diethyl carbonate=1: 6), inlet amount 3mL/h, the pyrocatechol transformation efficiency is 94.3%, and the 2-ethoxy-phenol selectivity is 61.6%.
Embodiment 2
With 1% activated alumina load saltpetre is that catalyzer carries out the catalyst activity evaluation on continuous fixed bed reactor, reaction conditions is as follows: 350 ℃ of temperature of reaction, proportioning raw materials (pyrocatechol: diethyl carbonate=1: 6), inlet amount 3mL/h, the pyrocatechol transformation efficiency is 44.6%, and the 2-ethoxy-phenol selectivity is 81.4%.
Embodiment 3
With 20% activated alumina load saltpetre is that catalyzer carries out the catalyst activity evaluation on continuous fixed bed reactor, reaction conditions is as follows: 350 ℃ of temperature of reaction, proportioning raw materials (pyrocatechol: diethyl carbonate=1: 6), inlet amount 3mL/h, the pyrocatechol transformation efficiency is 100%, and the 2-ethoxy-phenol selectivity is 54.3%.
Embodiment 4
With 15% activated alumina load potassium acetate is that catalyzer carries out the catalyst activity evaluation on continuous fixed bed reactor, reaction conditions is as follows: 350 ℃ of temperature of reaction, proportioning raw materials (pyrocatechol: diethyl carbonate=1: 4), inlet amount 3mL/h, the pyrocatechol transformation efficiency is 87.4%, and the 2-ethoxy-phenol selectivity is 71.9%.
Embodiment 5
With 15% activated alumina load salt of wormwood is that catalyzer carries out the catalyst activity evaluation on continuous fixed bed reactor, reaction conditions is as follows: 350 ℃ of temperature of reaction, proportioning raw materials (pyrocatechol: diethyl carbonate=1: 4), inlet amount 3mL/h, the pyrocatechol transformation efficiency is 79.4%, and the 2-ethoxy-phenol selectivity is 70.2%.
Embodiment 6
With 15% activated alumina load hydrogen potassium oxide is that catalyzer carries out the catalyst activity evaluation on continuous fixed bed reactor, reaction conditions is as follows: 350 ℃ of temperature of reaction, proportioning raw materials (pyrocatechol: diethyl carbonate=1: 4), inlet amount 3mL/h, the pyrocatechol transformation efficiency is 40.2%, and the 2-ethoxy-phenol selectivity is 79.0%.
Embodiment 7
With 15% activated alumina load aluminum chloride is that catalyzer carries out the catalyst activity evaluation on continuous fixed bed reactor, reaction conditions is as follows: 330 ℃ of temperature of reaction, proportioning raw materials (pyrocatechol: diethyl carbonate=1: 4), inlet amount 3mL/h, the pyrocatechol transformation efficiency is 100%, and the 2-ethoxy-phenol selectivity is 61.9%.
Embodiment 8
With 15% activated alumina load zinc chloride is that catalyzer carries out the catalyst activity evaluation on continuous fixed bed reactor, reaction conditions is as follows: 330 ℃ of temperature of reaction, proportioning raw materials (pyrocatechol: diethyl carbonate=1: 4), inlet amount 3mL/h, the pyrocatechol transformation efficiency is 100%, and the 2-ethoxy-phenol selectivity is 75.3%.
Embodiment 9
With 15% activated alumina load potassiumiodide is that catalyzer carries out the catalyst activity evaluation on continuous fixed bed reactor, reaction conditions is as follows: 350 ℃ of temperature of reaction, proportioning raw materials (pyrocatechol: diethyl carbonate=1: 4), inlet amount 3mL/h, the pyrocatechol transformation efficiency is 100%, and the 2-ethoxy-phenol selectivity is 50.5%.
Embodiment 10
With 15% activated alumina load nickelous nitrate is that catalyzer carries out the catalyst activity evaluation on continuous fixed bed reactor, reaction conditions is as follows: 330 ℃ of temperature of reaction, proportioning raw materials (pyrocatechol: diethyl carbonate=1: 4), inlet amount 3mL/h, the pyrocatechol transformation efficiency is 82.4%, and the 2-ethoxy-phenol selectivity is 83.6%.
Embodiment 11
With 15% activated alumina load lead nitrate is that catalyzer carries out the catalyst activity evaluation on continuous fixed bed reactor, reaction conditions is as follows: 330 ℃ of temperature of reaction, proportioning raw materials (pyrocatechol: diethyl carbonate=1: 4), inlet amount 3mL/h, the pyrocatechol transformation efficiency is 75.8%, and the 2-ethoxy-phenol selectivity is 84.9%.
Embodiment 12
With 15% activated alumina load lead acetate is that catalyzer carries out the catalyst activity evaluation on continuous fixed bed reactor, reaction conditions is as follows: 330 ℃ of temperature of reaction, proportioning raw materials (pyrocatechol: diethyl carbonate=1: 4), inlet amount 3mL/h, the pyrocatechol transformation efficiency is 80.6%, and the 2-ethoxy-phenol selectivity is 86.5%.
Embodiment 13
With 15% activated alumina load zinc nitrate is that catalyzer carries out the catalyst activity evaluation on continuous fixed bed reactor, reaction conditions is as follows: 330 ℃ of temperature of reaction, proportioning raw materials (pyrocatechol: diethyl carbonate=1: 4), inlet amount 3mL/h, the pyrocatechol transformation efficiency is 100%, and the 2-ethoxy-phenol selectivity is 79.7%.
Embodiment 14
With 15% activated alumina load zinc acetate is that catalyzer carries out the catalyst activity evaluation on continuous fixed bed reactor, reaction conditions is as follows: 350 ℃ of temperature of reaction, proportioning raw materials (pyrocatechol: diethyl carbonate=1: 4), inlet amount 3mL/h, the pyrocatechol transformation efficiency is 100%, and the 2-ethoxy-phenol selectivity is 58.7%.
Embodiment 15
With 15% activated alumina load cupric nitrate is that catalyzer carries out the catalyst activity evaluation on continuous fixed bed reactor, reaction conditions is as follows: 330 ℃ of temperature of reaction, proportioning raw materials (pyrocatechol: diethyl carbonate=1: 4), inlet amount 3mL/h, the pyrocatechol transformation efficiency is 54%, and the 2-ethoxy-phenol selectivity is 74.9%.
Embodiment 16
With 15% activated alumina load iron nitrate is that catalyzer carries out the catalyst activity evaluation on continuous fixed bed reactor, reaction conditions is as follows: 330 ℃ of temperature of reaction, proportioning raw materials (pyrocatechol: diethyl carbonate=1: 4), inlet amount 3mL/h, the pyrocatechol transformation efficiency is 100%, and the 2-ethoxy-phenol selectivity is 76.4%.
Embodiment 17
With 15% activated alumina load magnesium nitrate is that catalyzer carries out the catalyst activity evaluation on continuous fixed bed reactor, reaction conditions is as follows: 330 ℃ of temperature of reaction, proportioning raw materials (pyrocatechol: diethyl carbonate=1: 4), inlet amount 3mL/h, the pyrocatechol transformation efficiency is 100%, and the 2-ethoxy-phenol selectivity is 64%.
Embodiment 18
With 15% activated alumina load chromium nitrate is that catalyzer carries out the catalyst activity evaluation on continuous fixed bed reactor, reaction conditions is as follows: 330 ℃ of temperature of reaction, proportioning raw materials (pyrocatechol: diethyl carbonate=1: 4), inlet amount 3mL/h, the pyrocatechol transformation efficiency is 100%, and the 2-ethoxy-phenol selectivity is 91%.
Embodiment 19
With 15% activated alumina load chromium nitrate is that catalyzer carries out the catalyst activity evaluation on continuous fixed bed reactor, reaction conditions is as follows: 300 ℃ of temperature of reaction, proportioning raw materials (pyrocatechol: diethyl carbonate=1: 4), inlet amount 3mL/h, the pyrocatechol transformation efficiency is 94.2%, and the 2-ethoxy-phenol selectivity is 87.1%.
Embodiment 20
With 15% activated alumina load chromium nitrate is that catalyzer carries out the catalyst activity evaluation on continuous fixed bed reactor, reaction conditions is as follows: 380 ℃ of temperature of reaction, proportioning raw materials (pyrocatechol: diethyl carbonate=1: 4), inlet amount 3mL/h, the pyrocatechol transformation efficiency is 100%, and the 2-ethoxy-phenol selectivity is 82.5%.
Embodiment 21
With 15% activated alumina load chromium nitrate is that catalyzer carries out the catalyst activity evaluation on continuous fixed bed reactor, reaction conditions is as follows: 250 ℃ of temperature of reaction, proportioning raw materials (pyrocatechol: diethyl carbonate=1: 4), inlet amount 3mL/h, the pyrocatechol transformation efficiency is 79.3%, and the 2-ethoxy-phenol selectivity is 86.4%.
Embodiment 22
With 15% activated alumina load chromium nitrate is that catalyzer carries out the catalyst activity evaluation on continuous fixed bed reactor, reaction conditions is as follows: 330 ℃ of temperature of reaction, proportioning raw materials (pyrocatechol: diethyl carbonate=1: 2.5), inlet amount 3mL/h, the pyrocatechol transformation efficiency is 91%, and the 2-ethoxy-phenol selectivity is 84.5%.
Embodiment 23
With 15% activated carbon loaded magnesium acetate is that catalyzer carries out the catalyst activity evaluation on continuous fixed bed reactor, reaction conditions is as follows: 350 ℃ of temperature of reaction, proportioning raw materials (pyrocatechol: diethyl carbonate=1: 6), inlet amount 3mL/h, the pyrocatechol transformation efficiency is 89.7%, and the 2-ethoxy-phenol selectivity is 77.3%.
Embodiment 24
With the molecular sieve carried potassium acetate of 15%NaY is that catalyzer carries out the catalyst activity evaluation on continuous fixed bed reactor, reaction conditions is as follows: 350 ℃ of temperature of reaction, proportioning raw materials (pyrocatechol: diethyl carbonate=1: 6), inlet amount 3mL/h, the pyrocatechol transformation efficiency is 59.6%, and the 2-ethoxy-phenol selectivity is 73.9%.
Claims (5)
1, a kind of method of synthesizing 2-ethoxy-phenol, it is characterized in that raw materials used be diethyl carbonate and pyrocatechol, used catalyzer is with basic metal, alkaline-earth metal or transition metal such as nickel, plumbous, zinc, copper, aluminium, iron, the nitrate of chromium, carbonate, acetate, oxyhydroxide or halogenide are active ingredient, with activated alumina, gac or NaY molecular sieve are the loaded catalyst of carrier, the charge capacity of active ingredient is 1%～20% of a catalyst quality in the used loaded catalyst, temperature of reaction is 250～380 ℃, and the mol ratio of raw material pyrocatechol and diethyl carbonate is 1: 2.5～1: 6.
2, the method for a kind of synthesizing 2-ethoxy-phenol as claimed in claim 1, the active ingredient that it is characterized in that used loaded catalyst is a chromium nitrate.
3, the method for a kind of synthesizing 2-ethoxy-phenol as claimed in claim 1, the charge capacity that it is characterized in that active ingredient in the used loaded catalyst is 15%.
4, the method for a kind of synthesizing 2-ethoxy-phenol as claimed in claim 1 is characterized in that temperature of reaction is under 330 ℃.
5, the method for a kind of synthesizing 2-ethoxy-phenol as claimed in claim 1, the mol ratio that it is characterized in that raw material pyrocatechol and diethyl carbonate is 1: 4.
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|---|---|---|---|
| CNB2007100214246A CN100567240C (en) | 2007-04-11 | 2007-04-11 | A kind of method of synthesizing 2-ethoxy-phenol |
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|---|---|---|---|
| CNB2007100214246A CN100567240C (en) | 2007-04-11 | 2007-04-11 | A kind of method of synthesizing 2-ethoxy-phenol |
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| Publication Number | Publication Date |
|---|---|
| CN101033177A true CN101033177A (en) | 2007-09-12 |
| CN100567240C CN100567240C (en) | 2009-12-09 |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107814691A (en) * | 2017-11-01 | 2018-03-20 | 贝利化学（张家港）有限公司 | A kind of method for synthesizing guaethol |
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| CN111187148B (en) * | 2020-02-24 | 2022-08-09 | 上海大学 | Method for simultaneously preparing o-hydroxy phenetole and 1, 3-benzodioxole-2-one |
| CN111187148A (en) * | 2020-02-24 | 2020-05-22 | 上海大学 | Method for simultaneously preparing o-hydroxy phenetole and 1, 3-benzodioxole-2-one |
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| CN113509947A (en) * | 2021-07-21 | 2021-10-19 | 陕西煤业化工技术研究院有限责任公司 | Catalyst for synthesizing p-methyl anisole and preparation method and application thereof |
| CN113509947B (en) * | 2021-07-21 | 2023-09-26 | 陕西煤业化工技术研究院有限责任公司 | Catalyst for synthesizing p-methylanisole as well as preparation method and application thereof |
| CN114369012A (en) * | 2022-01-04 | 2022-04-19 | 万华化学集团股份有限公司 | Preparation method of 2- (2-hydroxyethoxy) phenol |
| CN114369012B (en) * | 2022-01-04 | 2023-05-30 | 万华化学集团股份有限公司 | Preparation method of 2- (2-hydroxyethoxy) phenol |
| CN115197052A (en) * | 2022-07-29 | 2022-10-18 | 常州大学 | Method for synthesizing o-hydroxy phenetole by hydroxyapatite catalysis |
| CN115197052B (en) * | 2022-07-29 | 2023-11-03 | 常州大学 | Method for synthesizing o-hydroxyphenylethyl ether by catalyzing hydroxyapatite |
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