CN1528727A - Method for condensing ethyl alcohol into n-butyl alcohol - Google Patents
Method for condensing ethyl alcohol into n-butyl alcohol Download PDFInfo
- Publication number
- CN1528727A CN1528727A CNA2003101080274A CN200310108027A CN1528727A CN 1528727 A CN1528727 A CN 1528727A CN A2003101080274 A CNA2003101080274 A CN A2003101080274A CN 200310108027 A CN200310108027 A CN 200310108027A CN 1528727 A CN1528727 A CN 1528727A
- Authority
- CN
- China
- Prior art keywords
- ethanol
- alcohol
- solution
- hours
- butanol
- 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.)
- Granted
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 47
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims abstract description 16
- 235000019441 ethanol Nutrition 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000919 ceramic Substances 0.000 claims abstract description 4
- 238000006482 condensation reaction Methods 0.000 claims abstract description 4
- 229910003158 γ-Al2O3 Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000000243 solution Substances 0.000 claims description 7
- 238000011049 filling Methods 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000011324 bead Substances 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 238000002791 soaking Methods 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 150000003840 hydrochlorides Chemical class 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 150000002823 nitrates Chemical class 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 7
- 239000011049 pearl Substances 0.000 abstract 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- AOPCKOPZYFFEDA-UHFFFAOYSA-N nickel(2+);dinitrate;hexahydrate Chemical compound O.O.O.O.O.O.[Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O AOPCKOPZYFFEDA-UHFFFAOYSA-N 0.000 description 3
- HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 238000007037 hydroformylation reaction Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
- TZYRSLHNPKPEFV-UHFFFAOYSA-N 2-ethyl-1-butanol Chemical compound CCC(CC)CO TZYRSLHNPKPEFV-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 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
- 239000006227 byproduct Substances 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- SXTLQDJHRPXDSB-UHFFFAOYSA-N copper;dinitrate;trihydrate Chemical compound O.O.O.[Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O SXTLQDJHRPXDSB-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a one-step method to condense alcohol into normal butanol, including: 1) dissolve metallic salt in water to prepare a 0.1-2.0 mol/L solution, then add in 20-40g gamma-Al2O3 to dip for 1-3 days, to obtain catalyst and place in tube reactor, fill ceramic pearls from top to bottom, charge hydrogen gas, preserve heat at 150-250 deg.C for 1-2 hours, then reduce at 300-800 deg.C for 3-5 hours; 2) control the reactor temperature at 120-350 deg.C, stop charging hydrogen gas, charge reacting matter alcohol solution, where the alcohol solution's concentration is 70-100%, the charging speed is 10-20mL/h, make condensation reaction at normal pressure and condense to collect the resultant. The normal butanol selectivity in the resultant is higher than 60%, and unreacted alcohol can circulate.
Description
Technical Field
The invention relates to a method for synthesizing n-butanol by ethanol in one step in a gas phase reaction.
Background
The n-butyl alcohol is an important chemical raw material, is mainly used for dibutyl phthalate, aliphatic dibasic acid butyl esters and butyl phosphate plasticizers, is widely used for various plastic and rubber products, and has the n-butyl alcohol yield of more than 200 million tons in the world in 2000. The synthesis method of n-butanol mainly comprises two methods: one method is to synthesize acetaldehyde with ethylene as raw material, condense with aldol, and then hydrogenate to obtain n-butanol, which is gradually replaced by another method, namely hydroformylation of propylene to synthesize butyraldehyde and isobutyraldehyde under the action of catalyst, wherein butanol is obtained after butyraldehyde hydrogenation. The hydroformylation of propylene is divided into high pressure processes operating at high pressures (19.6-34.3MPa) and high isomerization contents (20% -25% of isobutyraldehyde) and low pressure processes in which the catalyst is expensive (rhodium complex) and practical non-rhodium catalysts are under investigation.
Disclosure of Invention
The invention aims to provide a method for condensing ethanol into n-butanol, which has the advantages of low cost, convenient preparation and simple flow.
The method for condensing ethanol into n-butanol is a one-step synthesis method. The reaction formula is as follows:
the method comprises the following specific steps:
1) dissolving metal salt in water to prepare a solution with the concentration of 0.1-2.0 mol/L, and then adding 20-40 g of gamma-Al2O3Soaking for 1-3 days, drying to obtain a catalyst, filling the catalyst into a tubular reactor, filling ceramic beads up and down, introducing hydrogen, preserving the heat at 150-250 ℃ for 1-2 hours, and then reducing at 300-800 ℃ for 3-5 hours;
2) controlling the temperature of the reactor at 120-350 ℃, stopping introducing hydrogen, introducing a reactant ethanol aqueous solution, wherein the concentration of the ethanol aqueous solution is 70-100%, the introduction speed of the ethanol solution is 10-20 mL/h, carrying out condensation reaction at normal pressure, and collecting the product after condensation.
The metal salt can be one or more of nitrates or hydrochlorides of magnesium, cobalt, nickel, palladium and iron. In the step 2), the optimal temperature of the reactor is controlled to be 160-200 ℃.
The main by-products in the reaction are acetaldehyde, a small amount of n-butyl aldehyde, 2-ethyl butanol and n-hexyl alcohol, and most of unreacted ethanol can be recycled.
The method has the advantages of easily obtained raw materials, low cost, simple flow and convenient preparation, the selectivity of the n-butyl alcohol in the product is higher than 60 percent, and the unreacted ethanol after the product is separated can be recycled.
Detailed Description
The invention is further illustrated by the following examples.
Example 1
6.9 g of nickel nitrate hexahydrate are weighed and dissolved in 50ml of water, 34 g of gamma-Al is added after the nickel nitrate hexahydrate is completely dissolved2O3Soaking for 3 days, drying to obtain a catalyst, loading the catalyst into a tubular reactor, filling ceramic beads up and down, introducing hydrogen (80ml/min), heating to 250 ℃, preserving heat for 1 hour,and heating to 500 ℃ for reduction for 4 hours; after the reduction is finished, hydrogen is continuously introduced and cooled to 180 ℃, the introduction of the hydrogen is stopped, and 75 percent ethanol solution with the flow rate of 13.5ml/h is pumped by a liquid sample injection pump. And condensing and collecting a product, wherein the conversion per pass of the ethanol is 17 percent, and the selectivity of the n-butanol is 60 percent.
Example 2
6.1 g of copper nitrate trihydrate and 15.6 g of nickel nitrate hexahydrate are weighed and dissolved in 80ml of water, and 35.3 g of gamma-Al is added after the complete dissolution2O3The catalyst treatment and the condensation reaction were carried out under the same conditions as in example 1, and the reactant was absolute ethanol. The conversion per pass of ethanol was 20% and the n-butanol selectivity was 63%.
Example 3
Weighing 30 g of gamma-Al2O3The immersion contained 0.3 g of Pd2+And 50ml of palladium chloride solution, impregnated for 3 days, dried and placed in a reactor. Introducing hydrogen (80ml/min), heating to 150 ℃, preserving heat for 1 hour, and then heating to 350 ℃ for reduction for 4 hours. After the reduction is finished, the temperature is reduced to 200 ℃, hydrogen is stopped, 75% ethanol solution is introduced, the flow rate is 12ml/h, and products are collected after condensation. The conversion per pass of ethanol was 14% and the selectivity to n-butanol was 78%.
Claims (3)
1. The method for synthesizing the n-butanol by condensing the ethanol is characterized by comprising the following steps of:
1) dissolving metal salt in water to prepare a solution with the concentration of 0.1-2.0 mol/L, and then adding 20-40 g of gamma-Al2O3Soaking for 1-3 days, drying to obtain a catalyst, filling the catalyst into a tubular reactor, filling ceramic beads up and down, introducing hydrogen, preserving the heat at 150-250 ℃ for 1-2 hours, and then reducing at 300-800 ℃ for 3-5 hours;
2) controlling the temperature of the reactor at 120-350 ℃, stopping introducing hydrogen, introducing a reactant ethanol aqueous solution, wherein the concentration of the ethanol aqueous solution is 70-100%, the introduction speed of the ethanol solution is 10-20 mL/h, carrying out condensation reaction at normal pressure, and collecting the product after condensation.
2. The method of condensing ethanol into n-butanol according to claim 1, wherein said metal salt is one or more of nitrates or hydrochlorides of magnesium, cobalt, nickel, palladium and iron.
3. The method for condensing ethanol into n-butanol according to claim 1, wherein the optimal temperature of the reactor in step 2) is controlled to be 160-200 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200310108027 CN1216838C (en) | 2003-10-15 | 2003-10-15 | Method for condensing ethyl alcohol into n-butyl alcohol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200310108027 CN1216838C (en) | 2003-10-15 | 2003-10-15 | Method for condensing ethyl alcohol into n-butyl alcohol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1528727A true CN1528727A (en) | 2004-09-15 |
| CN1216838C CN1216838C (en) | 2005-08-31 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200310108027 Expired - Fee Related CN1216838C (en) | 2003-10-15 | 2003-10-15 | Method for condensing ethyl alcohol into n-butyl alcohol |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1216838C (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101530802B (en) * | 2009-04-16 | 2011-11-30 | 浙江大学 | Bi-component supported catalyst of ethanol condensed n-butanol and a method of preparing thereof |
| CN102666803A (en) * | 2009-10-13 | 2012-09-12 | 道达尔炼油与销售部 | Method for producing distillates by means of catalytic oligomerization of olefins in the presence of oxygenated compounds |
| CN103193593A (en) * | 2013-03-08 | 2013-07-10 | 吉林大学 | Method for preparing n-butanol from ethanol by using hydrothermal technique |
| US8962897B2 (en) | 2012-12-19 | 2015-02-24 | Celanese International Corporation | Catalysts and processes for producing butanol |
| US9018426B1 (en) | 2013-12-19 | 2015-04-28 | Celanese International Corporation | Processes for producing multi-carbon alcohols |
| US9024090B2 (en) | 2012-12-19 | 2015-05-05 | Celanese International Corporation | Catalysts and processes for producing butanol |
| CN104689857A (en) * | 2015-03-26 | 2015-06-10 | 中国科学院青岛生物能源与过程研究所 | Preparing method for nitrogen-doped porous carbon material, catalyst comprising material and application of material |
| CN106076344A (en) * | 2016-06-06 | 2016-11-09 | 浙江工业大学 | Activated carbon supported copper-metal oxide catalyst and preparation method and application thereof |
| CN107983328A (en) * | 2017-12-07 | 2018-05-04 | 中国科学院山西煤炭化学研究所 | A kind of catalyst of alcohol alcohol condensation reaction and its preparation method and application |
| CN109896923A (en) * | 2017-12-07 | 2019-06-18 | 中国科学院大连化学物理研究所 | A kind of method that ethyl alcohol conversion prepares high carbon primary alcohol on bicomponent catalyst |
-
2003
- 2003-10-15 CN CN 200310108027 patent/CN1216838C/en not_active Expired - Fee Related
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101530802B (en) * | 2009-04-16 | 2011-11-30 | 浙江大学 | Bi-component supported catalyst of ethanol condensed n-butanol and a method of preparing thereof |
| CN102666803A (en) * | 2009-10-13 | 2012-09-12 | 道达尔炼油与销售部 | Method for producing distillates by means of catalytic oligomerization of olefins in the presence of oxygenated compounds |
| US9024090B2 (en) | 2012-12-19 | 2015-05-05 | Celanese International Corporation | Catalysts and processes for producing butanol |
| CN104884159A (en) * | 2012-12-19 | 2015-09-02 | 国际人造丝公司 | Catalysts and processes for producing butanol |
| US8962897B2 (en) | 2012-12-19 | 2015-02-24 | Celanese International Corporation | Catalysts and processes for producing butanol |
| CN103193593B (en) * | 2013-03-08 | 2014-07-09 | 吉林大学 | Method for preparing n-butanol from ethanol by using hydrothermal technique |
| CN103193593A (en) * | 2013-03-08 | 2013-07-10 | 吉林大学 | Method for preparing n-butanol from ethanol by using hydrothermal technique |
| US9018426B1 (en) | 2013-12-19 | 2015-04-28 | Celanese International Corporation | Processes for producing multi-carbon alcohols |
| CN104689857A (en) * | 2015-03-26 | 2015-06-10 | 中国科学院青岛生物能源与过程研究所 | Preparing method for nitrogen-doped porous carbon material, catalyst comprising material and application of material |
| CN104689857B (en) * | 2015-03-26 | 2018-10-19 | 中国科学院青岛生物能源与过程研究所 | The preparation method of nitrogen-doped porous carbon material and the catalyst containing the material and purposes |
| CN106076344A (en) * | 2016-06-06 | 2016-11-09 | 浙江工业大学 | Activated carbon supported copper-metal oxide catalyst and preparation method and application thereof |
| CN106076344B (en) * | 2016-06-06 | 2018-08-21 | 浙江工业大学 | Activated carbon supported copper-metal oxide catalyst and preparation method and application thereof |
| CN107983328A (en) * | 2017-12-07 | 2018-05-04 | 中国科学院山西煤炭化学研究所 | A kind of catalyst of alcohol alcohol condensation reaction and its preparation method and application |
| CN109896923A (en) * | 2017-12-07 | 2019-06-18 | 中国科学院大连化学物理研究所 | A kind of method that ethyl alcohol conversion prepares high carbon primary alcohol on bicomponent catalyst |
| CN109896923B (en) * | 2017-12-07 | 2022-10-21 | 中国科学院大连化学物理研究所 | Method for preparing high-carbon primary alcohol by ethanol conversion on bi-component catalyst |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1216838C (en) | 2005-08-31 |
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