LU102403B1 - A method for preparing diol by auto-producing hydrogen and auto-hydrogenating at low temperature - Google Patents
A method for preparing diol by auto-producing hydrogen and auto-hydrogenating at low temperature Download PDFInfo
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- LU102403B1 LU102403B1 LU102403A LU102403A LU102403B1 LU 102403 B1 LU102403 B1 LU 102403B1 LU 102403 A LU102403 A LU 102403A LU 102403 A LU102403 A LU 102403A LU 102403 B1 LU102403 B1 LU 102403B1
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- Luxembourg
- Prior art keywords
- auto
- reaction substrate
- catalyst
- hydrogenating
- producing hydrogen
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 239000001257 hydrogen Substances 0.000 title claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 title claims abstract description 12
- 150000002009 diols Chemical class 0.000 title claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 239000000758 substrate Substances 0.000 claims abstract description 11
- 239000002184 metal Substances 0.000 claims abstract description 7
- 229910052751 metal Inorganic materials 0.000 claims abstract description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 15
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 5
- 239000000600 sorbitol Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 229910015373 AuCo Inorganic materials 0.000 claims description 2
- 229910015371 AuCu Inorganic materials 0.000 claims description 2
- 229910002711 AuNi Inorganic materials 0.000 claims description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
- 229910021118 PdCo Inorganic materials 0.000 claims description 2
- 229910002669 PdNi Inorganic materials 0.000 claims description 2
- 229910002837 PtCo Inorganic materials 0.000 claims description 2
- 229910002836 PtFe Inorganic materials 0.000 claims description 2
- 229910019041 PtMn Inorganic materials 0.000 claims description 2
- 229910002844 PtNi Inorganic materials 0.000 claims description 2
- 229910002849 PtRu Inorganic materials 0.000 claims description 2
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 150000002016 disaccharides Chemical class 0.000 claims description 2
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 2
- 239000000811 xylitol Substances 0.000 claims description 2
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 2
- 229960002675 xylitol Drugs 0.000 claims description 2
- 235000010447 xylitol Nutrition 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- -1 ethylene diol Chemical class 0.000 description 1
- 239000002803 fossil fuel Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000003786 synthesis 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/48—Silver or gold
- B01J23/52—Gold
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/42—Platinum
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/46—Ruthenium, rhodium, osmium or iridium
- B01J23/462—Ruthenium
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
- B01J23/8913—Cobalt and noble metals
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/89—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with noble metals
- B01J23/8926—Copper and noble metals
-
- 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
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
-
- 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
- C07C29/60—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by elimination of -OH groups, e.g. by dehydration
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
The invention discloses a method for preparing diol by auto-producing hydrogen and auto-hydrogenating at low temperature, which comprises the following steps: (1) The molar ratio of metal catalyst to reaction substrate is 1:50 to 1: 200; (2) The operating temperature is 120~240°C; (3) The operating pressure is 80 times of the nitrogen pressure of the standard atmospheric pressure; (4) The mass fraction of the reaction substrate in the solution is 1~55%; (5) The contact time between reaction substrate and catalyst is about 0.5~48 hours; (6) The technological process can be intermittent or continuous. The invention has a simple and convenient preparation process, good preparation effect and high working efficiency.
Description
Description A method for preparing diol by auto-producing hydrogen and auto-hydrogenating at low temperature
TECHNICAL FIELD The invention is related to a method for preparing diol by auto-producing hydrogen and auto-hydrogenating at low temperature.
BACKGROUND Diol is a very important chemical raw material and an important precursor for preparing plastics and other materials. At present, bulk diol products such as 1,2- propanediol and ethylene diol mainly adopt fossil fuels as raw materials, which are processed by dehydrogenation, oxidation and hydrolysis at high temperature. The energy consumption of these products is very high, while the product yield in the process is very low. In additon, it also causes serious pollution to the environment. In recent years, one-step synthesis of dihydric alcohol is available by using biomass as raw material, but its process usually entails high operating temperature and hydrogen pressure. The main problem of the process is that the side effects are very serious due to the harsh operation conditions. At the same time, the use of high-pressure hydrogen poses a great hidden danger to the safety of the process.
SUMMARY The method for preparing diol by auto-producing hydrogen and auto-hydrogenating at low temperature comprises the following steps: 1
1) The reaction substrates are cellulose, disaccharides, sorbitol, xylitol and glycerol, and also include alcohols and acids with 1 to 4 carbons; 2) The molar ratio of metal catalyst to reaction substrate is 1:50 to 1: 200; 3) The operating temperature is 120~240°C; 4) The operating pressure is 80 times of the nitrogen pressure of the standard atmospheric pressure; 5) The mass fraction of the reaction substrate in the solution is 1~55%; 6) The contact time between reaction substrate and catalyst is about 0.5~48 hours; 7) The technological process can be intermittent or continuous; The metal catalysts include monometallic of Pt, Au, Ru, and Pd; As bimetallic catalysts include PtCu, PtNi, PtFe, PtCo, PtMn, PtRu, AuCu, AuCo, AuNi, AuMn, PdCu, PdCo, PdNi, RuCu, RuNi, RuCo, and PdRu.
After adopting the above steps, the invention will have the beneficial effect as follows: The invention has a simple and convenient preparation process, good preparation effect and high working efficiency.
DESCRIPTION OF THE INVENTION In order to make the object, technical scheme and advantages of the present invention clearer, the present invention will be further described in detail with reference to specific 2 examples. It is to be understood that the examples described herein are used only to explain the invention, and are not intended to limit the invention.
1. Experiment of auto-producing hydrogen and auto-hydrogenating of glycerol Table 1. Reaction results of auto-producing hydrogen and auto-hydrogenating of glycerol Conte T nt of Conver Propyle | Ethyle ; Alcoh | Gaseous Catalyzer cataly -sion ne ne | Acids ols | product (°C) 9 zer (g) rate(%) | glycol | glycol me [mue [sw je 0 [mv JT lL I CO LA cr jo fous Jw Ju fm jo [fo] The numbers in brackets represent metal loading, for example, Pt(5)/C: 5w% of Pt content, with C carrier. The reaction conditions: 1g of glycerol, 0.2g of NaOH and H2O are taken as solvent, with the total reaction volume is 50 mL, 10 bar of N as the pressure, and 6h for the reaction time.
2. Experiment of auto-producing hydrogen and auto-hydrogenating of sorbitol Table 2. Reaction results of auto-producing hydrogen and auto-hydrogenating of sorbitol 3
Content Prop Ethvle Gaseo T of Conversio y y Acid | Alcohol us Catalyzer ° lene ne (°C) catalyzer | n rate(%) glyc | glycol Ss s produc (g) ol t CE 160 fous Jw Jao Ju a 0 c so fous Jw au [m Ju foo | co 120 fous Jo fa fa Jie 9 fo so [ons Jw fw Ju f= fo fo | The numbers in brackets represent metal loading, for example, Pt(5)/C: 5w% of Pt content, with C carrier. The reaction conditions: 1g of sorbitol, 0.2g of NaOH and H2O are taken as solvent, with the total reaction volume is 50 mL, 10 bar of N as the pressure, and 6h for the reaction time.
For those skilled in the art, it is obvious that the present invention is not limited to the details of the foregoing exemplary examples, and the present invention can be implemented in other specific forms without departing from the spirit or basic characteristics of the present invention. Therefore, from any point of view, the examples should be regarded as exemplary but not limited. The scope of the present invention is defined by the appended claims rather 4 than the above description, so it is intended to include all changes falling within the meaning and scope of the equivalent elements of the claims in the invention.
It is obvious to those skilled in the art that the present invention is not limited to the details of the above exemplary examples, and that the present invention can be realized in other specific forms without departing from the spirit or basic characteristics of the present invention. Therefore, the examples should be regarded as exemplary and non-limiting from any point of view, and the scope of the present invention is defined by the appended claims rather than the above description, so it is intended to embrace all changes falling within the meaning and range of equivalent elements of the claims.
In addition, it should be understood that although this specification is described according to examples, each embodiment does not contain only one independent technical solution. The description of this specification is only for the sake of clarity, and those skilled in the art should take the specification as a whole. The technical solutions in each embodiment can also be combined appropriately to form other examples that can be understood by those skilled in the art.
Claims (3)
1. The method for preparing diol by auto-producing hydrogen and auto-hydrogenating at low temperature comprises the following steps: 1) the reaction substrates are cellulose, disaccharides, sorbitol, xylitol and glycerol, and also include alcohols and acids with 1 to 4 carbons; 2) the molar ratio of metal catalyst to reaction substrate is 1:50 to 1: 200; 3) the operating temperature is 120~240°C; 4) the operating pressure is 80 times of the nitrogen pressure of the standard atmospheric pressure; 5) the mass fraction of the reaction substrate in the solution is 1~55%; 6) the contact time between reaction substrate and catalyst is about 0.5~48 hours; 7) the technological process can be intermittent or continuous;
2. Method according to claim 1, wherein the metal catalysts include monometallic of Pt, Au, Ru, and Pd; as bimetallic catalysts include PtCu, PtNi, PtFe, PtCo, PtMn, PtRu, AuCu, AuCo, AuNi, AuMn, PdCu, PdCo, PdNi, RuCu, RuNi, RuCo, and PdRu.
3. Method according to claim 2, further comprising the step of preparing the bimetallic catalyst according to the catalyst of claim 2. 6
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU102403A LU102403B1 (en) | 2021-01-12 | 2021-01-12 | A method for preparing diol by auto-producing hydrogen and auto-hydrogenating at low temperature |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU102403A LU102403B1 (en) | 2021-01-12 | 2021-01-12 | A method for preparing diol by auto-producing hydrogen and auto-hydrogenating at low temperature |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU102403B1 true LU102403B1 (en) | 2021-08-03 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU102403A LU102403B1 (en) | 2021-01-12 | 2021-01-12 | A method for preparing diol by auto-producing hydrogen and auto-hydrogenating at low temperature |
Country Status (1)
| Country | Link |
|---|---|
| LU (1) | LU102403B1 (en) |
-
2021
- 2021-01-12 LU LU102403A patent/LU102403B1/en active IP Right Grant
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Effective date: 20210803 |