CN113149939A - Method for preparing alkenyl succinic anhydride by tubular reactor - Google Patents
Method for preparing alkenyl succinic anhydride by tubular reactor Download PDFInfo
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- CN113149939A CN113149939A CN202110161217.0A CN202110161217A CN113149939A CN 113149939 A CN113149939 A CN 113149939A CN 202110161217 A CN202110161217 A CN 202110161217A CN 113149939 A CN113149939 A CN 113149939A
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- tubular reactor
- alkenyl succinic
- succinic anhydride
- maleic anhydride
- anhydride
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
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- 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
- Y02P20/584—Recycling of catalysts
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Abstract
The invention discloses a method for preparing alkenyl succinic anhydride by a tubular reactor, which comprises the following steps of carrying out hot melting on maleic anhydride in a melting tank to obtain a maleic anhydride hot melt; respectively pumping the maleic anhydride hot melt and the internal olefin into the tubular reactor simultaneously through two metering delivery pumps; reacting in a tubular reactor at 220-280 deg.C under 0.3-0.8 Mpa for 1-8 min; transferring the material to a purification device for crude product refining after reaction to obtain the alkenyl succinic anhydride. The invention greatly shortens the reaction time by adopting the new process of the tubular reactor; the method has the advantages that the high reaction efficiency can be achieved without adding a solid catalyst in the preparation process of the tubular reactor, the subsequent catalyst recovery process is saved, the reaction time is greatly shortened, and the continuous and safe production is realized; the tubular reactor reduces the equipment requirement, is easy to operate, and reduces the occupied area and investment.
Description
Technical Field
The invention relates to the technical field of compound synthesis, in particular to a method for preparing alkenyl succinic anhydride by using a tubular reactor.
Background
Alkenyl succinic anhydride (ASA for short) is a basic raw material widely used in light industry and fine chemical industry, is widely applied to lubricating oil, waterproof agent, hardener, drying agent and preservative, and is particularly applied to the field of papermaking production by using a reactive sizing agent, so that the tensile strength, waterproof performance, whiteness, opacity and wear resistance of paper can be greatly improved, and the chemical environment in the papermaking process can be improved. The liquid is oily amber liquid at normal temperature, is formed by connecting unsaturated olefin skeletons with succinic anhydride, and has a molecular structure containing two hydrophobic groups and a reactive anhydride group.
ASA is usually prepared by olefin and maleic anhydride at a higher temperature through a tank reactor, and the method of dropwise adding is adopted, the reaction speed is strictly controlled, the reaction time is long, the batch operation is realized, and the production period is longer; in addition, maleic anhydride and olefin are easy to polymerize, oxidize and decompose to generate a large amount of byproducts, so that the yield is low, and the refined tar substrate is difficult to treat; in the preparation process, a solid catalyst needs to be added to promote the reaction, the catalyst is expensive, and needs to be recycled, so that the cost is high.
Disclosure of Invention
In view of the defects of the prior art, the invention aims to provide a method for preparing alkenyl succinic anhydride by using a tubular reactor, which solves the problems of long reaction time, low yield and the like of alkenyl succinic anhydride synthesis in the prior art.
The purpose of the invention is realized by the following technical scheme:
a tubular reactor process for preparing alkenyl succinic anhydride comprising the steps of:
step 1) carrying out hot melting on maleic anhydride in a melting tank to obtain a maleic anhydride hot melt;
step 2) pumping the maleic anhydride hot melt and the internal olefin obtained in the step 1 into a tubular reactor simultaneously through two metering delivery pumps;
step 3) reacting in a tubular reactor at 220-280 ℃ and 0.3-0.8 MPa for 1-8 min;
and 4) transferring the material after the reaction to a purification device for refining a crude product to obtain the alkenyl succinic anhydride.
Further, the molar ratio of the maleic anhydride to the internal olefin is 1-2: 1.
Further, the internal olefin is CnH2n, and n is one or more of 12-22.
Furthermore, the material of the tubular reactor is silicon carbide, stainless steel or hastelloy.
Further, the inner diameter of the pipeline of the tubular reactor is 1mm-50 mm.
The invention has the outstanding effects that:
the method for preparing alkenyl succinic anhydride by using the tubular reactor replaces the traditional kettle-type dripping process condition, and greatly shortens the reaction time by adopting the new process of the tubular reactor; the tubular reactor has extremely high heat and mass transfer efficiency, the traditional dropwise addition reaction needs to add a catalyst to accelerate the reaction, and the tubular reactor can achieve higher reaction efficiency without adding a solid catalyst in the preparation process, thereby saving the subsequent catalyst recovery process, greatly shortening the reaction time and realizing the continuous and safe production; the tubular reactor reduces the equipment requirement, is easy to operate, and reduces the occupied area and investment.
The following detailed description of the embodiments of the present invention is provided in connection with the examples to facilitate understanding and understanding of the technical solutions of the present invention.
Detailed Description
The process of the present invention is illustrated below by means of specific examples, but the present invention is not limited thereto. The experimental methods described in the following examples are all conventional methods unless otherwise specified; the reagents and materials are commercially available, unless otherwise specified.
Example 1
The tubular reactor process of this example for preparing alkenyl succinic anhydride comprises the following steps:
step 1) carrying out hot melting on maleic anhydride in a melting tank to obtain a maleic anhydride hot melt, wherein the hot melting temperature is 75 ℃;
step 2) pumping the maleic anhydride hot melt obtained in the step 1 and the internal olefin mixed with the hexadecane and the octadecane into a tubular reactor simultaneously through two metering delivery pumps, wherein the molar ratio of the maleic anhydride to the internal olefin mixed with the hexadecane and the octadecane is 1: 1;
step 3) reacting in a tubular reactor at 220 ℃ and 0.8Mpa for 1 min;
and 4) transferring the material after the reaction to a purification device for refining a crude product to obtain the alkenyl succinic anhydride.
Wherein, the tubular reactor model is: VTRWSS 05; the material of the tubular reactor is 316L stainless steel; the internal diameter of the tube of the tubular reactor was 1 mm.
Example 2
The tubular reactor process of this example for preparing alkenyl succinic anhydride comprises the following steps:
step 1) carrying out hot melting on maleic anhydride in a melting tank to obtain a maleic anhydride hot melt, wherein the hot melting temperature is 75 ℃;
step 2) pumping the maleic anhydride hot melt obtained in the step 1 and the carbon dodecainternal olefin into a tubular reactor simultaneously through two metering delivery pumps, wherein the molar ratio of the maleic anhydride to the carbon dodecainternal olefin is 2: 1;
step 3) reacting in a tubular reactor at the reaction temperature of 280 ℃ and the pressure of 0.5Mpa for 3 min;
and 4) transferring the material after the reaction to a purification device for refining a crude product to obtain the alkenyl succinic anhydride.
Wherein, the tubular reactor model is: VTRWSS 05; the tubular reactor is made of hastelloy; the internal diameter of the tube of the tubular reactor was 50 mm.
Example 3
The tubular reactor process of this example for preparing alkenyl succinic anhydride comprises the following steps:
step 1) carrying out hot melting on maleic anhydride in a melting tank to obtain a maleic anhydride hot melt, wherein the hot melting temperature is 75 ℃;
step 2) pumping the maleic anhydride hot melt obtained in the step 1 and the carbon twenty-carbon dodecaolefin mixture into a tubular reactor simultaneously through two metering delivery pumps, wherein the molar ratio of the maleic anhydride to the carbon twenty-carbon dodecaolefin mixture is 1.5: 1;
step 3) reacting in a tubular reactor at 260 ℃ and 0.3Mpa for 5 min;
and 4) transferring the material after the reaction to a purification device for refining a crude product to obtain the alkenyl succinic anhydride.
Wherein, the tubular reactor model is: VTRWSS 05; the material of the tubular reactor is silicon carbide; the internal diameter of the tube reactor was 30 mm.
Example 4
The tubular reactor process of this example for preparing alkenyl succinic anhydride comprises the following steps:
step 1) carrying out hot melting on maleic anhydride in a melting tank to obtain a maleic anhydride hot melt, wherein the hot melting temperature is 75 ℃;
step 2) pumping the maleic anhydride hot melt and the hexadecane internal olefin obtained in the step 1 into a tubular reactor simultaneously through two metering delivery pumps, wherein the molar ratio of the maleic anhydride to the hexadecane internal olefin is 2: 1;
step 3) reacting in a tubular reactor at 250 ℃ and 0.5Mpa for 8 min;
and 4) transferring the material after the reaction to a purification device for refining a crude product to obtain the alkenyl succinic anhydride.
Wherein, the tubular reactor model is: VTRWSS 05; the material of the tubular reactor is 316L stainless steel; the internal diameter of the tube of the tubular reactor was 10 mm.
Comparative example:
a method of synthesizing alkenyl succinic anhydride of this comparative example, comprising the steps of:
step 1) placing 98g of maleic anhydride in a constant pressure funnel, winding a hot water heat tracing pipe outside the constant pressure funnel, and carrying out hot melting on the maleic anhydride, wherein the temperature of the hot water is 75 ℃ to obtain a maleic anhydride hot melt;
step 2) adding 250g of internal olefin mixed by sixteen carbon and eighteen carbon and 2g of solid catalyst into a four-neck flask together, setting the reaction temperature to be 250 ℃, and beginning to dropwise add for 5 hours;
and 3) after the reaction, precipitating and filtering a product to remove the catalyst, and purifying by reduced pressure distillation to obtain alkenyl succinic anhydride which is oily thick amber liquid with the yield of 45%.
Performance test experiments:
water absorption value of hand sheet pattern
Yield: based on the amount of maleic anhydride charged
Density: full-automatic desk type density proportion instrument
Viscosity: viscometer, model Brookfield, DV-II + Pro, 62 spindle; and (3) constant-temperature water bath: 25 +/-0.5 deg.C, 0-100 deg.C, and division value of 0.1 deg.C.
The results of the measurements are shown in the following table:
| name (R) | Yield/% | Density/g/cm3 | Viscosity/cps | Appearance of the product |
| Example 1 | 75.6 | 0.927 | 141 | Amber transparent liquid |
| Example 2 | 78.4 | 0.954 | 150 | Amber transparent liquid |
| Example 3 | 82.5 | 0.976 | 153 | Amber transparent liquid |
| Example 4 | 80.2 | 0.931 | 145 | Amber transparent liquid |
| Comparative example | 74.23 | 0.953 | 134 | Amber transparent liquid |
The detection and application effect prove that all indexes of the ASA prepared by the method are within the range of standard requirements, and the application effect is not different from that of the product prepared by the original process.
The invention has various embodiments, and all technical solutions formed by adopting equivalent transformation or equivalent transformation are within the protection scope of the invention.
Claims (5)
1. A tubular reactor process for preparing alkenyl succinic anhydride, comprising the steps of:
step 1) carrying out hot melting on maleic anhydride in a melting tank to obtain a maleic anhydride hot melt;
step 2) pumping the maleic anhydride hot melt and the internal olefin obtained in the step 1 into a tubular reactor simultaneously through two metering delivery pumps;
step 3) reacting in a tubular reactor at 220-280 ℃ and 0.3-0.8 MPa for 1-8 min;
and 4) transferring the material after the reaction to a purification device for refining a crude product to obtain the alkenyl succinic anhydride.
2. The method for preparing alkenyl succinic anhydride by using the tubular reactor as claimed in claim 1, wherein: the molar ratio of the maleic anhydride to the internal olefin is 1-2: 1.
3. The method for preparing alkenyl succinic anhydride by using the tubular reactor as claimed in claim 1, wherein: the internal olefin is CnH2n, and n is one or more of 12-22.
4. The method for preparing alkenyl succinic anhydride by using the tubular reactor as claimed in claim 1, wherein: the tubular reactor is made of silicon carbide, stainless steel or hastelloy.
5. The method for preparing alkenyl succinic anhydride by using the tubular reactor as claimed in claim 1, wherein: the inner diameter of the pipeline of the tubular reactor is 1mm-50 mm.
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| CN202110161217.0A CN113149939A (en) | 2021-02-05 | 2021-02-05 | Method for preparing alkenyl succinic anhydride by tubular reactor |
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| CN202110161217.0A CN113149939A (en) | 2021-02-05 | 2021-02-05 | Method for preparing alkenyl succinic anhydride by tubular reactor |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113666888A (en) * | 2021-09-23 | 2021-11-19 | 上海昶法新材料有限公司 | Method for preparing methyl morpholine oxide by adopting tubular reactor |
Citations (9)
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|---|---|---|---|---|
| US4581464A (en) * | 1984-12-24 | 1986-04-08 | Monsanto Company | Preparation of alkenyl succinic anhydrides |
| US4599432A (en) * | 1983-11-25 | 1986-07-08 | Mitsubishi Chemical Industries Ltd. | Process for preparing a composition containing an alkenyl succinic anhydride |
| US4761488A (en) * | 1987-11-13 | 1988-08-02 | Shell Oil Company | Reaction of olefins with maleic anhydride |
| CN1609092A (en) * | 2003-10-23 | 2005-04-27 | 魏素芬 | Prepn process of high purity alkenyl succinic anhydride |
| CN101309890A (en) * | 2005-11-18 | 2008-11-19 | 巴斯夫欧洲公司 | Alkenylsuccinic anhydrides formed from oligomers of c4-to c8-olefins and maleic anhydride, processes for their preparation and their use |
| CN102015671A (en) * | 2008-04-29 | 2011-04-13 | 阿克佐诺贝尔股份有限公司 | Paper sizing additives, their preparation process, and their use |
| CN105924415A (en) * | 2016-04-07 | 2016-09-07 | 辽宁石油化工大学 | Method for producing alkenyl succinic anhydride |
| CN107849463A (en) * | 2015-06-12 | 2018-03-27 | 芬兰国家技术研究中心股份公司 | Method and apparatus and compound for producing compound and application thereof |
| EP3549937A1 (en) * | 2018-04-05 | 2019-10-09 | Karl-Heinz Elsässer | Process for the continuous preparation of c16-asa (hexadecene succinic anhydride) and/or c18-asa (octadecene succinic anhydride) |
-
2021
- 2021-02-05 CN CN202110161217.0A patent/CN113149939A/en active Pending
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4599432A (en) * | 1983-11-25 | 1986-07-08 | Mitsubishi Chemical Industries Ltd. | Process for preparing a composition containing an alkenyl succinic anhydride |
| US4581464A (en) * | 1984-12-24 | 1986-04-08 | Monsanto Company | Preparation of alkenyl succinic anhydrides |
| US4761488A (en) * | 1987-11-13 | 1988-08-02 | Shell Oil Company | Reaction of olefins with maleic anhydride |
| CN1609092A (en) * | 2003-10-23 | 2005-04-27 | 魏素芬 | Prepn process of high purity alkenyl succinic anhydride |
| CN101309890A (en) * | 2005-11-18 | 2008-11-19 | 巴斯夫欧洲公司 | Alkenylsuccinic anhydrides formed from oligomers of c4-to c8-olefins and maleic anhydride, processes for their preparation and their use |
| CN102015671A (en) * | 2008-04-29 | 2011-04-13 | 阿克佐诺贝尔股份有限公司 | Paper sizing additives, their preparation process, and their use |
| CN107849463A (en) * | 2015-06-12 | 2018-03-27 | 芬兰国家技术研究中心股份公司 | Method and apparatus and compound for producing compound and application thereof |
| CN105924415A (en) * | 2016-04-07 | 2016-09-07 | 辽宁石油化工大学 | Method for producing alkenyl succinic anhydride |
| EP3549937A1 (en) * | 2018-04-05 | 2019-10-09 | Karl-Heinz Elsässer | Process for the continuous preparation of c16-asa (hexadecene succinic anhydride) and/or c18-asa (octadecene succinic anhydride) |
Non-Patent Citations (1)
| Title |
|---|
| 王绍宇等: "烯基琥珀酸酐(ASA)的合成及异构体分离的研究", 《合成材料老化与应用》, vol. 44, no. 2, pages 83 - 85 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113666888A (en) * | 2021-09-23 | 2021-11-19 | 上海昶法新材料有限公司 | Method for preparing methyl morpholine oxide by adopting tubular reactor |
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