CN113943207A - Process for synthesizing butanediol by hydrogenation of succinaldehyde - Google Patents
Process for synthesizing butanediol by hydrogenation of succinaldehyde Download PDFInfo
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- CN113943207A CN113943207A CN202111391285.2A CN202111391285A CN113943207A CN 113943207 A CN113943207 A CN 113943207A CN 202111391285 A CN202111391285 A CN 202111391285A CN 113943207 A CN113943207 A CN 113943207A
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- succinaldehyde
- butanediol
- copper
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- 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
- C07C29/136—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 of >C=O containing groups, e.g. —COOH
- C07C29/14—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 of >C=O containing groups, e.g. —COOH of a —CHO group
- C07C29/141—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 of >C=O containing groups, e.g. —COOH of a —CHO group with hydrogen or hydrogen-containing gases
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Abstract
The invention discloses a process for synthesizing butanediol by hydrogenation of succinaldehyde, which comprises the following steps: adding 1, 4-butanedialdehyde into a fixed bed reactor, introducing hydrogen, filling a copper-chromium composite catalyst into the fixed bed, and reacting under the catalytic action of the copper-chromium composite catalyst to obtain the 1, 4-butanediol. Compared with the prior art, the embodiment of the invention has at least the following advantages or beneficial effects: the invention takes the succinaldehyde and the hydrogen as raw materials, takes the copper/chromium as a catalyst, synthesizes the butanediol by the liquid phase hydrogenation of the succinaldehyde, and has the advantages of mild reaction temperature and pressure conditions, high conversion rate of the succinaldehyde and high selectivity of the butanediol.
Description
Technical Field
The invention relates to the technical field of compound preparation, in particular to a process for synthesizing butanediol by hydrogenation of succinaldehyde.
Background
The 1, 4-butanediol is an important basic organic chemical raw material and fine chemical raw material, has wide application, and the derivative of the 1, 4-butanediol is a fine chemical product with high added value and is widely used in the fields of solvents, medicines, polyurethane, fibers, engineering plastics, cosmetics, plasticizers, curing agents, pesticides and the like.
The production method of butanediol includes an alkynal method, a butadiene acetyloxidation method, a dichlorobutene hydrolysis method, an allyl alcohol hydroformylation method, a maleic anhydride hydrogenation method and the like, and currently, an industrial device mainly adopts the alkynal method. However, the alkyne-aldehyde method has the disadvantages of long process flow, high hydrogenation pressure and the like.
Disclosure of Invention
The invention aims to provide a process for synthesizing butanediol by hydrogenation of succinaldehyde, which has the advantages of simple process and mild reaction conditions.
The technical problem to be solved by the invention is realized by adopting the following technical scheme.
The embodiment of the application provides a process for synthesizing butanediol by hydrogenation of succinaldehyde, which comprises the following steps:
adding 1, 4-butanedialdehyde into a fixed bed reactor, introducing hydrogen, filling a copper-chromium composite catalyst into the fixed bed, and reacting under the catalytic action of the copper-chromium composite catalyst to obtain the 1, 4-butanediol.
In some embodiments of the invention, the molar ratio of the hydrogen to the 1, 4-butanedialdehyde is (2.01-2.5): 1.
in some embodiments of the invention, the fixed bed reactor is an adiabatic reactor, and heat generated by the reaction is cooled and taken away by external circulating liquid.
In some embodiments of the invention, the fixed bed reactor is a shell-and-tube isothermal reactor, the 1, 4-butanedialdehyde, the hydrogen and the copper-chromium composite catalyst are in a tube pass, and the reaction heat is vaporized and carried away by a cooling liquid in the shell pass.
In some embodiments of the invention, the reaction pressure is 0.4 to 2.5MPaG, and the reaction temperature is 80 to 250 ℃.
In some embodiments of the invention, the reaction time is 0.5 to 2 hours.
In some embodiments of the invention, the copper-chromium composite catalyst comprises 5-50% of copper oxide and 20-80% of copper chromite.
The reaction equation of the invention is as follows:
OHCCH2CH2CHO+2H2→HOCH2CH2CH2CH2OH
compared with the prior art, the embodiment of the invention has at least the following advantages or beneficial effects:
the invention takes the succinaldehyde and the hydrogen as raw materials, takes the copper/chromium as a catalyst, synthesizes the butanediol by the liquid phase hydrogenation of the succinaldehyde, and has the advantages of mild reaction temperature and pressure conditions, high conversion rate of the succinaldehyde and high selectivity of the butanediol.
The main scheme and the further selection schemes can be freely combined to form a plurality of schemes which are all adopted and claimed by the invention; in the invention, the selection (each non-conflict selection) and other selections can be freely combined. The skilled person in the art can understand that there are many combinations, which are all the technical solutions to be protected by the present invention, according to the prior art and the common general knowledge after understanding the scheme of the present invention, and the technical solutions are not exhaustive herein.
Detailed Description
The following non-limiting examples serve to illustrate the invention.
Example 1
Firstly, filling a copper-chromium composite catalyst in the tube pass of a shell-and-tube constant temperature reactor, and then mixing 1, 4-succinaldehyde and hydrogen according to the weight ratio of 1: 2.01 of the molar ratio, and the copper chromium composite catalyst comprises 5 percent of copper oxide and 80 percent of chromium oxide copper; the reaction pressure is 2.5MPaG, the reaction temperature is 250 ℃, and the reaction time is 0.5 hour to obtain the 1, 4-butanediol. The conversion rate of 1, 4-butanediol is 99%, and the selectivity of 1, 4-butanediol is 99%.
Example 2
Mixing 1, 4-butanedialdehyde and hydrogen according to the weight ratio of 1: 2.5, adding the mixture into a reactor filled with a copper-chromium composite catalyst in an adiabatic manner, wherein the copper-chromium composite catalyst comprises 50% of copper oxide and 20% of copper dichromate tetraoxide; the reaction pressure is 0.4MPaG, the reaction temperature is 80 ℃, the reaction time is 2 hours, and the 1, 4-butanediol is obtained by reaction. The conversion rate of 1, 4-butanediol was 97%, and the selectivity of 1, 4-butanediol was 99.5%.
Example 3
Mixing 1, 4-butanedialdehyde and hydrogen according to the weight ratio of 1: 2.1, adding the mixture into an adiabatic reactor filled with a copper-chromium composite catalyst, wherein the copper-chromium composite catalyst comprises 25 percent of copper oxide and 50 percent of copper dichromate tetraoxide; the reaction pressure is 1.8MPaG, the reaction temperature is 200 ℃, the reaction time is 1 hour, and the 1, 4-butanediol is obtained by the reaction. The conversion rate of 1, 4-butanedialdehyde was 99.5%, and the selectivity of 1, 4-butanediol was 99.5%.
The foregoing basic embodiments of the invention and their various further alternatives can be freely combined to form multiple embodiments, all of which are contemplated and claimed herein. In the scheme of the invention, each selection example can be combined with any other basic example and selection example at will.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.
Claims (7)
1. A process for synthesizing butanediol by hydrogenation of succinaldehyde is characterized by comprising the following steps:
adding 1, 4-butanedialdehyde into a fixed bed reactor, introducing hydrogen, and reacting under the catalytic action of a copper-chromium composite catalyst to obtain 1, 4-butanediol.
2. The process for synthesizing butanediol by hydrogenating succinaldehyde according to claim 1, wherein the molar ratio of the hydrogen to the 1, 4-succinaldehyde is (2.01-2.5): 1.
3. the process for synthesizing butanediol by hydrogenating succinaldehyde according to claim 1, wherein the fixed bed reactor is an adiabatic reactor, and heat generated by the reaction is taken away by cooling an external circulating liquid.
4. The process for synthesizing butanediol by hydrogenation of succinaldehyde according to claim 1, wherein the fixed bed reactor is a shell-and-tube isothermal reactor, the 1, 4-succinaldehyde, the hydrogen and the copper-chromium composite catalyst are in a tube pass, and the reaction heat is removed by vaporization of a cooling liquid in the shell pass.
5. The process for synthesizing butanediol by hydrogenation of succinaldehyde according to claim 1, wherein the reaction pressure is 0.4-2.5 MPaG and the reaction temperature is 80-250 ℃.
6. The process for synthesizing butanediol by hydrogenation of succinaldehyde according to claim 1, wherein the reaction time is 0.5-2 h.
7. The process for synthesizing butanediol by hydrogenation of succinaldehyde according to claim 6, wherein the copper-chromium composite catalyst comprises 5-50% of copper oxide and 20-80% of copper chromite.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111391285.2A CN113943207A (en) | 2021-11-23 | 2021-11-23 | Process for synthesizing butanediol by hydrogenation of succinaldehyde |
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| CN202111391285.2A CN113943207A (en) | 2021-11-23 | 2021-11-23 | Process for synthesizing butanediol by hydrogenation of succinaldehyde |
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Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0431923A2 (en) * | 1989-12-07 | 1991-06-12 | Tonen Corporation | Process for producing 1,4-butanediol and tetrahydrofuran |
| EP0672643A2 (en) * | 1994-03-15 | 1995-09-20 | Chemie Linz Gesellschaft m.b.H. | Hydrogenolytic reduction of an aldehyde to an alcohol in the presence of a monolithic catalyst |
| CN1565728A (en) * | 2003-06-18 | 2005-01-19 | 中国石油天然气股份有限公司 | Catalyst and method for preparing 1,5 pentanediol by hydrogenation of 1,5 dimethyl glutarate |
| CN101225022A (en) * | 2008-02-13 | 2008-07-23 | 上海华谊丙烯酸有限公司 | Method for preparing 1,5-pentadiol by hydrogenation of 1,5-glutaraldehyde |
| CN101270032A (en) * | 2008-04-16 | 2008-09-24 | 上海华谊丙烯酸有限公司 | Method for preparing 1,5-pentanediol |
| CN101774940A (en) * | 2010-01-19 | 2010-07-14 | 浙江大学 | Para-N-(4-hydroxyl-3-methoxy benzyl)-8-methyl-5-nonene amide and method for preparing same |
| CN111393259A (en) * | 2019-01-02 | 2020-07-10 | 南京大学淮安高新技术研究院 | Method for preparing 1, 3-butanediol by catalytic hydrogenation |
| CN112390712A (en) * | 2019-08-14 | 2021-02-23 | 中国科学院青岛生物能源与过程研究所 | Method for preparing 1, 3-butanediol by adopting fixed bed continuous reaction |
| CN113860989A (en) * | 2021-11-08 | 2021-12-31 | 中国天辰工程有限公司 | Synthesis method of 1, 6-hexanediol |
-
2021
- 2021-11-23 CN CN202111391285.2A patent/CN113943207A/en active Pending
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0431923A2 (en) * | 1989-12-07 | 1991-06-12 | Tonen Corporation | Process for producing 1,4-butanediol and tetrahydrofuran |
| EP0672643A2 (en) * | 1994-03-15 | 1995-09-20 | Chemie Linz Gesellschaft m.b.H. | Hydrogenolytic reduction of an aldehyde to an alcohol in the presence of a monolithic catalyst |
| CN1565728A (en) * | 2003-06-18 | 2005-01-19 | 中国石油天然气股份有限公司 | Catalyst and method for preparing 1,5 pentanediol by hydrogenation of 1,5 dimethyl glutarate |
| CN101225022A (en) * | 2008-02-13 | 2008-07-23 | 上海华谊丙烯酸有限公司 | Method for preparing 1,5-pentadiol by hydrogenation of 1,5-glutaraldehyde |
| CN101270032A (en) * | 2008-04-16 | 2008-09-24 | 上海华谊丙烯酸有限公司 | Method for preparing 1,5-pentanediol |
| CN101774940A (en) * | 2010-01-19 | 2010-07-14 | 浙江大学 | Para-N-(4-hydroxyl-3-methoxy benzyl)-8-methyl-5-nonene amide and method for preparing same |
| CN111393259A (en) * | 2019-01-02 | 2020-07-10 | 南京大学淮安高新技术研究院 | Method for preparing 1, 3-butanediol by catalytic hydrogenation |
| CN112390712A (en) * | 2019-08-14 | 2021-02-23 | 中国科学院青岛生物能源与过程研究所 | Method for preparing 1, 3-butanediol by adopting fixed bed continuous reaction |
| CN113860989A (en) * | 2021-11-08 | 2021-12-31 | 中国天辰工程有限公司 | Synthesis method of 1, 6-hexanediol |
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