CN114524708B - Method for preparing n-butanol from ethanol - Google Patents
Method for preparing n-butanol from ethanol Download PDFInfo
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- CN114524708B CN114524708B CN202011320029.XA CN202011320029A CN114524708B CN 114524708 B CN114524708 B CN 114524708B CN 202011320029 A CN202011320029 A CN 202011320029A CN 114524708 B CN114524708 B CN 114524708B
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- ethanol
- butanol
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- iridium complex
- alkali
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 74
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 title claims abstract description 66
- 238000000034 method Methods 0.000 title claims abstract description 11
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 15
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003513 alkali Substances 0.000 claims abstract description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 150000001450 anions Chemical class 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 230000035484 reaction time Effects 0.000 claims description 10
- 239000003446 ligand Substances 0.000 claims description 9
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 4
- -1 tetrafluoroborate Chemical compound 0.000 claims description 4
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 2
- 239000000920 calcium hydroxide Substances 0.000 claims description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 2
- 239000000347 magnesium hydroxide Substances 0.000 claims description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 5
- 238000007869 Guerbet synthesis reaction Methods 0.000 abstract description 4
- 239000002904 solvent Substances 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 2
- 239000000654 additive Substances 0.000 abstract 2
- 230000000996 additive effect Effects 0.000 abstract 2
- 239000000295 fuel oil Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 description 8
- 239000007789 gas Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 2
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 description 1
- 229910020366 ClO 4 Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000002816 fuel additive Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/32—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups
- C07C29/34—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups by condensation involving hydroxy groups or the mineral ester groups derived therefrom, e.g. Guerbet reaction
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/184—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine mixed aromatic/aliphatic ring systems, e.g. indoline
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0225—Complexes comprising pentahapto-cyclopentadienyl analogues
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/827—Iridium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a method for preparing n-butanol from ethanol. The preparation method comprises the following steps: the iridium complex and alkali are weighed and dissolved in ethanol, and n-butanol is prepared through Guerbet reaction of the ethanol. The n-butanol reported by the invention has wide application, can be used as a solvent and a synthetic raw material in various fields of modern chemical industry, can be used as an additive of fuel oil, and has more advantages than an ethanol additive.
Description
Technical Field
The invention belongs to the technical field of organic chemistry, and in particular relates to a method for preparing n-butanol from ethanol
Background
N-butanol is an important chemical product, and is mainly used for preparing n-butyl plasticizers, and also used as raw materials for preparing butyraldehyde, butyric acid, butylamine, butyl lactate and the like. N-butanol may also be added to gasoline as a fuel additive.
In recent years, a method for preparing n-butanol directly from ethanol through a Guerbet reaction in one step has been receiving attention. At present, the homogeneous catalyst with highest activity is a Picer type Ru and Mn type catalyst, and the structural formula isBoth catalysts exhibit high activity for catalyzing the reaction of ethanol to n-butanol, with Mn complexes having catalyst conversion numbers as high as 114120 (J.Am.chem. Soc.2016,138,9077; J.Am.chem. Soc.2017,139, 11941). However, the ligand synthesis for Mn complexes is complex, and the phosphine ligand groups contained therein are sensitive to water and air, increasing the operational difficulty of the reaction and the cost of the catalyst. Thus, it is particularly important to develop a catalyst that is stable to water and air.
Disclosure of Invention
Aiming at the problems of the existing synthesis of n-butanol by taking ethanol as a raw material: ligand synthesis of homogeneous catalysts is complex and sensitive to air and water. The invention provides a method for preparing n-butanol by taking a high-activity iridium complex as a catalyst (TON > 10000) and ethanol as a raw material and a solvent, wherein the ligand and the iridium complex are stable to water and air.
The method for preparing n-butanol from ethanol takes ethanol as a raw material, and adopts Guerbet reaction with a metallic iridium complex as a catalyst, and specifically comprises the following steps:
specifically, an iridium complex and alkali are added into ethanol, and the structural formula (formula 1) of iridium complex cations is as follows:
formula 1, L is a bidentate ligand; the structural formula of the bidentate ligand L is as follows: R 1 is H, or R 1 is a F, cl, br, CF 3、Me、OMe、OH、NH2 or NMe 2 substituent on the phenyl ring; n=0, 1, 2, 3, 4,5,6, 7, 8, 9 or 10. The iridium complex anions are: one or more of trifluoromethane sulfonate (OTf), chloride (Cl), bromide (Br), sulfate (SO 4), tetrafluoroborate (BF 4), nitrate (NO 3), hexafluorophosphate (PF 6), perchlorate (ClO 4), p-toluenesulfonate (OTs), bis (trifluoromethane sulfonyl) imide (NTf 2), trifluoroacetate (TFA) or acetate (OAc). The amount of iridium complex is 0.01-10gL -1; the concentration of the alkali is 0.01-100gL -1. The optimal amount of iridium complex is 0.5-5gL -1; the optimum concentration of base is 2-20gL -1. The inert gas and/or nitrogen pressure is 0.1-3.0Mpa; the reaction temperature is 100-180 ℃, and the reaction time is as follows: 0.5-100h. The alkali is one or a combination of several of potassium hydroxide, sodium hydroxide, calcium hydroxide, magnesium hydroxide, sodium ethoxide, sodium tert-butoxide and potassium tert-butoxide.
The beneficial effects of the invention are as follows: the iridium complex has low dosage, high stability of the complex and ligand, high catalytic activity and reduced production cost. The Guerbet reaction for preparing n-butanol by ethanol is realized in ethanol, and the problem of additional separation and purification caused by using other solvents is avoided.
Detailed Description
The present invention will be further described with reference to specific examples, but the scope of the present invention is not limited to the examples, and if those skilled in the art make some insubstantial improvements and modifications in the present invention based on the above description, it is still within the scope of the present invention.
Example 1
Preparing n-butanol from ethanol: 0.4mg of Ir complex (formula 1, wherein R1 is NMe 2 and the anion is Cl) was weighed out, 3.0mL of ethanol was weighed out, and 30mg of potassium hydroxide was weighed out. The nitrogen pressure of the system was 10bar, the temperature was 140℃and the reaction time was 6h. After the reaction, the product n-butanol was analyzed in the gas phase, TON (catalyst conversion) =3302, and the yield was 5.1%.
Example 2
Preparing n-butanol from ethanol: 0.4mg of Ir complex (represented by formula 1, R1 is CF 3, and the anion is Cl) was weighed out, 3.0mL of ethanol was weighed out, and 30mg of potassium hydroxide was weighed out. The nitrogen pressure of the system is 20bar, the temperature is 150 ℃, and the reaction time is 6h. After the reaction, the product n-butanol was analyzed in a gas phase, ton=4480, and the yield was 6.9%.
Example 3
Preparing n-butanol from ethanol: 0.2mg of Ir complex (formula 1, wherein R1 is H and the anion is OTf) was weighed out, 3.0mL of ethanol was weighed out, and 30mg of potassium hydroxide was weighed out. The nitrogen pressure of the system is 10bar, the temperature is 150 ℃ and the reaction time is 22h. After the reaction, the product n-butanol was analyzed in a gas phase, ton= 15861, and the yield was 2.4%.
Example 4
Preparing n-butanol from ethanol: 0.7mg of Ir complex (formula 1, n=3, anion is Cl) was weighed out, 3.0mL of ethanol was weighed out, and 23mg of sodium ethoxide was weighed out. The nitrogen pressure of the system is 10bar, the temperature is 160 ℃, and the reaction time is 110h. After the reaction, n-butanol was analyzed in a gas phase, ton= 38233, and the yield was 5.8%.
Example 5
Preparing n-butanol from ethanol: 0.7mg of Ir complex (formula 1, n=3, anion is Cl) was weighed out, 3.0mL of ethanol was weighed out, and 23mg of sodium ethoxide was weighed out. The nitrogen pressure of the system is 10bar, the temperature is 160 ℃, and the reaction time is 110h. After the reaction, the product n-butanol was analyzed in a gas phase, and the yield was 7.8%.
Example 6
Preparing n-butanol from ethanol: 7mg of Ir complex (formula 1, n=4, the anion is Cl) was weighed out, 30mL of ethanol was weighed out, and 230mg of sodium ethoxide was weighed out. The nitrogen pressure of the system is 20bar, the temperature is 160 ℃, and the reaction time is 110h. After the reaction, the product n-butanol was analyzed in a gas phase, and the yield was 8.4%.
Example 7
Preparing n-butanol from ethanol: 0.4mg of Ir complex (formula 1, n=6, anion is Cl) was weighed out, 3.0mL of ethanol was weighed out, and 23mg of sodium ethoxide was weighed out. The nitrogen pressure of the system is 10bar, the temperature is 160 ℃, and the reaction time is 24h. After the reaction, the product n-butanol was analyzed in a gas phase, and the yield was 2.8%.
Example 8
Preparing n-butanol from ethanol: 1.0mg of Ir complex (formula 1, n=3, anion is SO 4) was weighed out, 3.0mL of ethanol was weighed out, and 46mg of sodium ethoxide was weighed out. The nitrogen pressure of the system is 20bar, the temperature is 160 ℃, and the reaction time is 48h. After the reaction, the product n-butanol was analyzed in a gas phase, and the yield was 6.4%.
Claims (4)
1. A method for preparing n-butanol from ethanol is characterized by comprising the following steps: specifically, an iridium complex and alkali are added into ethanol, and the structural formula of iridium complex cations is as follows: Formula 1, L is a bidentate ligand;
the structural formula of the bidentate ligand L is as follows: or/> R 1 is H, F, cl, br, me, OMe, OH, NH 2 or NMe 2 substituent; n=3, 4, 5,6, 7, 8, 9 or 10; in the reaction system, the pressure of inert gas and/or nitrogen is 0.1-3.0 Mpa; the reaction temperature is 100-180 ℃, and the reaction time is as follows: 0.5-100 h; the alkali is one or the combination of more of potassium hydroxide, sodium hydroxide, calcium hydroxide, magnesium hydroxide, sodium ethoxide, sodium tert-butoxide and potassium tert-butoxide.
2. The method for preparing n-butanol from ethanol according to claim 1, wherein:
wherein the amount of iridium complex is 0.01-10 gL -1; the concentration of the alkali is 0.01-100 gL -1.
3. The method for preparing n-butanol from ethanol according to claim 1, wherein:
Wherein the amount of iridium complex is 0.5-5 gL -1; the concentration of the alkali is 2-20 gL -1.
4. The method for preparing n-butanol from ethanol according to claim 1, wherein: the iridium complex anions are: one or more of trifluoromethane sulfonate, chloride, bromide, sulfate, tetrafluoroborate, nitrate, hexafluorophosphate, perchlorate, p-toluenesulfonate, bis (trifluoromethane sulfonyl) imide, trifluoroacetate or acetate.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106810431A (en) * | 2015-11-30 | 2017-06-09 | 中国科学院大连化学物理研究所 | The method of complex of iridium catalytic hydrogenation 5 hydroxymethyl furfural 1- hydroxyl -2,5- acetyl butyryls |
| WO2019193079A1 (en) * | 2018-04-05 | 2019-10-10 | Alma Mater Studiorum - Universita' Di Bologna | Improved process for the transformation of primary aliphatic alcohols into higher aliphatic alcohols |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US9902673B2 (en) * | 2015-07-16 | 2018-02-27 | The University Of Rochester | Methods for producing butanol |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106810431A (en) * | 2015-11-30 | 2017-06-09 | 中国科学院大连化学物理研究所 | The method of complex of iridium catalytic hydrogenation 5 hydroxymethyl furfural 1- hydroxyl -2,5- acetyl butyryls |
| WO2019193079A1 (en) * | 2018-04-05 | 2019-10-10 | Alma Mater Studiorum - Universita' Di Bologna | Improved process for the transformation of primary aliphatic alcohols into higher aliphatic alcohols |
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