CN113651776B - Purifying agent for aldehyde impurity-containing compound and application thereof - Google Patents
Purifying agent for aldehyde impurity-containing compound and application thereof Download PDFInfo
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Abstract
The invention provides a purifying agent of a compound containing aldehyde impurities and application thereof. The purifying agent comprises alkali metal borohydride and hydrazine hydrate, wherein the mole percentages of the alkali metal borohydride and the hydrazine hydrate are 2-20% and 80-98%, respectively. The purifying agent is added in the rectification and purification process of the crude propylene oxide or the crude isopentenol containing 50-1000 ppm of aldehyde impurities, so that the content of the aldehyde impurities can be reduced to below 20ppm, and the problems of low efficiency in removing the impurity aldehydes in the crude propylene oxide or the crude isopentenol and limited purity of the obtained product in the prior art are solved. The purifying agent provided by the invention has high impurity removing efficiency and is convenient to apply.
Description
Technical Field
The invention belongs to the field of purifying agents, and particularly relates to a purifying agent for a compound containing aldehyde impurities and application thereof.
Background
Propylene oxide is a third largest propylene derivative next to polypropylene and acrylonitrile, is a very important basic organic chemical raw material, and is mainly used for producing polyether polyol and further producing polyurethane. Propylene oxide can also be used for preparing nonionic surfactant, allyl alcohol, propylene glycol, synthetic glycerol, etc. Propylene oxide derived fine chemicals are used in almost all industrial sectors and daily life. Although the reaction for directly oxidizing propylene and hydrogen peroxide to produce propylene oxide has high raw material conversion rate and product propylene oxide selectivity, a large amount of solvents (such as methanol), water and excessive propylene exist in the reaction process, so that small amounts of aldehyde, ether, ester and ketone impurities are generated in the product besides the target product propylene oxide. Propylene oxide is mainly used for preparing polyether polyols, and the polyether polyols thus prepared are used as raw materials for producing polyurethane foams. Propylene oxide for these applications must meet stringent purity requirements, where aldehydes must be below 100ppm. For a few applications, it is even necessary to reduce the aldehyde impurity content to 20ppm or less, however, the boiling point of impurities such as acetaldehyde is similar to that of propylene oxide, so that it is difficult to separate them from propylene oxide by ordinary distillation.
A number of patents disclose a process for purifying propylene oxide, and publication US 3881996 discloses a process for purifying propylene oxide using a multistage distillation which is capable of purifying less than 10ppm of aldehydes, but the distillation process is very energy intensive. Patent publication No. CN 101298443B discloses a process for purifying crude propylene oxide containing methanol and acetaldehyde by continuous operation of extractive distillation by adding an unsubstituted NH containing solvent to the distillation column above the point of feed of the crude propylene oxide in addition to an extraction solvent which reduces the volatility of the methanol 2 A compound capable of reacting with acetaldehyde, thereby obtaining purified propylene oxide containing less than 100ppm of methanol and less than 100ppm of acetaldehyde, but less than 20ppm of acetaldehyde. For most applications, it is desirable that the aldehyde impurity level in propylene oxide be less than 100ppm, and for a few applications it is desirable to reduce the aldehyde impurity level in propylene oxide to below 20ppm. Therefore, the development of an efficient and convenient method for removing aldehyde impurities in propylene oxide has important significance.
The isopentenol, namely 3-methyl-2-buten-1-ol, is an important organic synthesis intermediate, has wide application in the fields of pesticides, synthetic fragrances and the like, has wider and wider application range along with the continuous deep process of the isopentenol synthesis, and greatly increases the demand, so that the isopentenol synthesis process has important significance in the research of the isopentenol synthesis technology. The traditional method for producing the isopentenol comprises an isoprene method, wherein isoprene is used as a raw material, and the isoprene is prepared through a plurality of steps of oxidation, acetification, saponification and the like, and has the advantages of long process route, low product selectivity and serious environmental pollution. In recent years, isopentenol is prepared from isobutene and formaldehyde, the method is simple in process and low in pollution, 3-methyl-3-buten-1-ol is obtained by condensing isobutene and formaldehyde, isopentenol is obtained by isomerization, isopentenol is produced in the isomerization reaction process, the boiling point of isopentenol is similar to that of isopentenol and is azeotropic, the quality of isopentenol is seriously affected by the existence of isopentenol, and therefore, the content of isopentenol is required to be reduced by a simple and effective method.
Disclosure of Invention
The invention solves the problems of low efficiency in removing impurity aldehydes in crude propylene oxide or crude isopentenol and limited purity of the obtained product in the prior art. In order to solve the technical problems, the invention provides a purifying agent for a compound containing aldehyde impurities and application thereof. The preparation of the purifying agent is simple and cheap, and the purifying agent has excellent effect of removing impurity aldehydes in crude propylene oxide or crude isopentenol.
Specifically, the invention provides the following technical scheme:
in one aspect, the present invention provides a purifying agent for a compound containing an aldehyde impurity, characterized in that the purifying agent comprises an alkali metal borohydride and hydrazine hydrate.
Preferably, the purifying agent for aldehyde impurity-containing compounds of the present invention is characterized in that the molar percentage of the borohydride of alkali metal in the purifying agent is 2 to 20%, more preferably 5 to 15%.
Preferably, the purifying agent of the compound containing aldehyde impurities is characterized in that the molar percentage of hydrazine hydrate in the purifying agent is 80-98%. More preferably 85 to 95%.
Preferably, the purifying agent of the compound containing aldehyde impurities is characterized in that the borohydride of the alkali metal is one or a combination of two of sodium borohydride and potassium borohydride.
On the other hand, the invention also provides a method for purifying the compound containing the aldehyde impurities, which is characterized in that the compound containing the aldehyde impurities and the purifying agent are added into a rectifying tower to carry out rectification, and the top fraction is collected to obtain the compound with the aldehyde impurity content lower than 20ppm.
Preferably, the purification method of the compound containing aldehyde impurities is characterized in that the compound is propylene oxide or 1, 2-butylene oxide, preferably propylene oxide; the aldehyde impurities are one or more of formaldehyde, acetaldehyde and propionaldehyde.
Preferably, the method for purifying the compound containing the aldehyde impurity is characterized in that the compound is isopentenyl alcohol, and the aldehyde impurity is isopentenyl aldehyde.
Preferably, the purification method of the compound containing the aldehyde impurity is characterized in that the content of the aldehyde impurity in the compound is 50-1000 ppm.
Preferably, the purification method of the compound containing aldehyde impurities according to the present invention is characterized in that the molar ratio of the purifying agent to the aldehyde impurities is (1-2): 1.
preferably, the purification method of the compound containing aldehyde impurities is characterized in that propylene oxide is prepared by reacting propylene with hydrogen peroxide, and more preferably 1, 2-butylene oxide is prepared by reacting 1-butylene with hydrogen peroxide.
Preferably, the purification method of the compound containing aldehyde impurities is characterized in that the isopentenol is prepared by isomerism reaction of 3-methyl-3-butene-1-ol.
In another aspect, the invention also provides the use of the purifying agent according to any of the above in the purification of compounds containing aldehyde impurities.
In another aspect, the invention also provides the use of the purification agent of any one of the above in the field of purification agents.
The beneficial effects of the invention include: the purifying agent provided by the invention is simple to prepare and convenient to apply; the purifying agent provided by the invention has high aldehyde removal rate, and can reduce the aldehyde impurity content to below 20 ppm; the purifying agent provided by the invention can be applied to the purification process of propylene oxide and also can be applied to the purification of isopentenol.
Detailed Description
The invention provides a purifying agent for aldehyde impurity-containing compound and application thereof, which solves the problems of low removing efficiency of impurity aldehydes in crude propylene oxide or crude isopentenol and limited purity of the obtained product in the prior art, wherein the purifying agent comprises alkali metal borohydride and hydrazine hydrate, and the mole percentages of the alkali metal borohydride and the hydrazine hydrate in the purifying agent are respectively 2-20% and 80-98%. The purification agent is added in the rectification and purification process of crude propylene oxide or crude isopentenol containing 50-1000 ppm of aldehyde impurities, so that the aldehyde impurities content can be reduced to below 20ppm.
The reagents used in the examples of the present invention are shown in Table 1 below. The materials used in the examples were selected from any commercially available reagents or industrial products unless otherwise specified.
TABLE 1
| Reagents/apparatus | Purity/model | Manufacturer' s |
| Silica sol | Silicon oxide content of 30+ -1% | QINGDAO HAIYANG CHEMICAL Co.,Ltd. |
| Sesbania powder | ＞98％ | Heterocyanine powder Co.Ltd |
| Hydrazine hydrate | ＞98％ | Alatine |
| Sodium borohydride | ＞98％ | Ala (Ala)Butyl |
| Potassium borohydride | ＞98％ | Alatine |
| Propylene | ＞99％ | Large Lian Yong Feng gas Limited |
| Hydrogen peroxide | H 2 O 2 The purity is 30 to 50 percent | Daliansheng chemical industry |
| Methanol | ＞99％ | Dalianxinmu chemical Co., ltd |
| Strip extruder | Model DJ40 | ZIBO LINZI HAICHANG MACHINERY Co.,Ltd. |
The titanium-silicon molecular sieve used as the catalyst for the reaction of propylene and hydrogen peroxide is self-made or commercially available, and the relative crystallinity of the titanium-silicon molecular sieve is more than 95 percent. For a better explanation of the present invention, the process of preparing the titanium silicalite molecular sieve is stated, but is not limited to the titanium silicalite molecular sieve prepared by the method described below.
The preparation method of the titanium-silicon molecular sieve TS-1 comprises the following steps: the silica sol is used as a silicon source, tetrabutyl titanate is used as a titanium source, tetrapropylammonium bromide is used as a template agent, and the mass ratio of the silica sol to the tetrabutyl titanate to the tetrapropylammonium bromide is 91.5:4:4.5, crystallizing the raw materials at 150-200 ℃ for 12-48h, filtering, washing to neutrality, drying at 100 ℃ and roasting at 500 ℃ for 4h to obtain the titanium-silicon molecular sieve TS-1 raw powder. Mixing raw powder and sesbania powder uniformly, adding silicasol, mixing uniformly, extruding strips by a strip extruder, drying the formed sample at 100 ℃ for 12 hours, and roasting at 500 ℃ for 4 hours to obtain the strip titanium-silicon molecular sieve TS-1, wherein the mass ratio of the sesbania powder to the raw powder to the silicasol is 1:16.5:82.5.
The laboratory rectification column used in this example was a packed rectification column packed with a glass spring, the rectification column height was 80cm and the diameter was 3cm, the rectification was carried out under normal pressure or reduced pressure, and the materials were separated by reflux at their respective boiling points.
The present invention will be described in detail with reference to specific examples. The technical means used in the present invention are all methods known to those skilled in the art unless specifically stated otherwise. The embodiments should be considered as illustrative, and not limiting, the scope of the invention being limited only by the claims. Various changes or modifications to the materials ingredients and amounts used in these embodiments will be apparent to those skilled in the art without departing from the spirit and scope of the invention.
Example 1 preparation of propylene oxide containing aldehyde impurities
Continuously introducing raw materials of propylene, hydrogen peroxide and solvent methanol into a fixed bed reaction device filled with titanium silicalite molecular sieve from bottom to top. Raw materials of propylene, hydrogen peroxide and solvent methanol are mixed according to a mole ratio of 3:1:6, the reaction temperature of the fixed bed is 50 ℃ and the reaction pressure is 3.0MPa. The product at the outlet of the reactor contains unreacted raw material propylene, solvent methanol, product propylene oxide, methyl formate, acetone, acetaldehyde and other impurities. The product passes through the top of a packed rectifying tower, unreacted raw material propylene is firstly separated, then crude propylene oxide product containing acetaldehyde impurities is separated from the top of the tower, and the content of acetaldehyde in the crude propylene oxide is obtained by gas chromatography quantitative analysis.
EXAMPLE 2 purification of crude propylene oxide
2kg of the crude propylene oxide obtained in example 1 was weighed and fed into a rectifying apparatus, 0.0433g of sodium borohydride and 1.089g of hydrazine hydrate were added to carry out rectification, and an overhead fraction was collected and quantitatively analyzed by gas chromatography, wherein the acetaldehyde content in the purified propylene oxide was 12ppm.
EXAMPLE 3 purification of crude propylene oxide
2kg of the crude propylene oxide obtained in example 1 was weighed and fed into a rectifying apparatus, 0.0520g of sodium borohydride and 1.307g of hydrazine hydrate were added to carry out rectification, and the overhead fraction was collected and quantitatively analyzed by gas chromatography, wherein the acetaldehyde content in the purified propylene oxide was 10ppm.
EXAMPLE 4 purification of crude propylene oxide
2kg of the crude propylene oxide obtained in example 1 was weighed and fed into a rectifying apparatus, 0.0693g of sodium borohydride and 1.055g of hydrazine hydrate were added to carry out rectification, and the overhead fraction was collected and quantitatively analyzed by gas chromatography, wherein the acetaldehyde content in the purified propylene oxide was 10ppm.
EXAMPLE 5 purification of crude propylene oxide
2kg of the crude propylene oxide obtained in example 1 was weighed and fed into a rectifying apparatus, 0.0173g of sodium borohydride and 1.123g of hydrazine hydrate were added to carry out rectification, and the overhead fraction was collected and quantitatively analyzed by gas chromatography, whereby the acetaldehyde content in the purified propylene oxide was 15ppm.
EXAMPLE 6 purification of crude propylene oxide
2kg of the crude propylene oxide obtained in example 1 was weighed and fed into a rectifying device, 0.0618g of potassium borohydride and 1.089g of hydrazine hydrate were added to conduct rectification, the overhead fraction was collected, and the purified propylene oxide had an acetaldehyde content of 11ppm by means of quantitative analysis by gas chromatography.
EXAMPLE 7 preparation of propylene oxide containing aldehyde impurities
Continuously introducing raw materials of propylene, hydrogen peroxide and solvent methanol into a fixed bed reaction device filled with titanium silicalite molecular sieve from bottom to top. Raw materials of propylene, hydrogen peroxide and solvent methanol are mixed according to a mole ratio of 3:1:4.5, the fixed bed reaction temperature is 40 ℃ and the reaction pressure is 3.0MPa. The product at the outlet of the reactor contains unreacted raw material propylene, solvent methanol, product propylene oxide, methyl formate, acetone, acetaldehyde and other impurities. The unreacted raw material propylene is firstly separated from the product through the top of the rectifying tower, then the crude propylene oxide product containing acetaldehyde impurities is separated from the top of the rectifying tower, and the content of acetaldehyde in the crude propylene oxide is 166ppm by using gas chromatography quantitative analysis.
EXAMPLE 8 purification of crude propylene oxide
2kg of the crude propylene oxide obtained in example 7 was weighed and fed into a rectifying apparatus, 0.0142g of sodium borohydride and 0.359g of hydrazine hydrate were added, and rectification was carried out, and the overhead fraction was collected and quantitatively analyzed by gas chromatography, whereby the acetaldehyde content in the purified propylene oxide was 9ppm.
EXAMPLE 9 preparation of isopentenol containing aldehyde impurity
Weighing 2kg of raw material 3-methyl-3-butene-1-ol, 4kg of methanol and 40g of sodium methoxide; the three materials are uniformly mixed, after the methanol for the reaction tube is pressurized to 12mpa, the material starts to be fed, the mixed material is fed by a plunger pump, and the flow rate is as follows: 70g/h, controlling the reaction temperature to 190 ℃, controlling the reaction pressure to 12mpa, collecting the reaction liquid, rectifying the obtained reaction liquid to obtain the isopentenyl alcohol, wherein the purity of the product is more than 99%, and quantitatively analyzing by gas chromatography to obtain that the content of the isopentenyl aldehyde in the crude isopentenyl alcohol is 336ppm.
EXAMPLE 10 purification of crude isopentenol
2kg of the crude prenol obtained in example 9 was weighed and fed into a rectifying device, 0.0363g of sodium borohydride and 0.432g of hydrazine hydrate were added, and the mixture was subjected to reduced pressure rectification, and the overhead fraction was collected, and quantitatively analyzed by gas chromatography, wherein the content of prenal in the purified prenol was 18ppm.
EXAMPLE 11 purification of crude isopentenol
2kg of the crude prenol obtained in example 9 was weighed and fed into a rectifying apparatus, 0.0681g of sodium borohydride and 0.511g of hydrazine hydrate were added, and the mixture was subjected to reduced pressure rectification, and the overhead fraction was collected, and quantitatively analyzed by gas chromatography, whereby the content of prenal in the purified prenol was 14ppm.
EXAMPLE 12 purification of crude propylene oxide
2kg of the crude propylene oxide obtained in example 1 was weighed and fed into a rectifying apparatus, 0.0086g of sodium borohydride was added, 1.134g of hydrazine hydrate was added, the mixture was rectified, and the overhead fraction was collected and quantitatively analyzed by gas chromatography, wherein the acetaldehyde content in the purified propylene oxide was 33ppm.
EXAMPLE 13 purification of crude isopentenol
2kg of the crude prenol obtained in example 9 was weighed and fed into a rectifying apparatus, 0.0036g of sodium borohydride was added, 0.475g of hydrazine hydrate was added, and the mixture was subjected to reduced pressure rectification, and the overhead fraction was collected, and quantitatively analyzed by gas chromatography, wherein the content of prenal in the purified prenol was 87ppm.
EXAMPLE 14 purification of crude propylene oxide
2kg of the crude propylene oxide obtained in example 1 was weighed and fed into a rectifying apparatus, 0.216g of sodium borohydride was added, 0.859g of hydrazine hydrate was added, the mixture was rectified, and the overhead fraction was collected and quantitatively analyzed by gas chromatography, wherein the acetaldehyde content in the purified propylene oxide was 10ppm.
The mole percent of sodium borohydride in the purifying agent in the example 14 is 25.1%, and the content of acetaldehyde in the purified epoxypropane is 10ppm; in example 3, the molar percentage of sodium borohydride in the purifying agent was 5.1%, and the acetaldehyde content of the purified propylene oxide was 10ppm.
EXAMPLE 15 purification of crude isopentenol
2kg of the crude prenol obtained in example 9 was weighed and fed into a rectifying device, 0.0906g of sodium borohydride was added, 0.360g of hydrazine hydrate was added, and the mixture was subjected to reduced pressure rectification, and the overhead fraction was collected, and quantitatively analyzed by gas chromatography, wherein the content of prenal in the purified prenol was 13ppm.
The molar percentage of sodium borohydride in the purifying agent in the above example 15 was 25.3%, and the content of isopentenyl aldehyde in the purified isopentenyl alcohol was 13ppm; the molar percentage of sodium borohydride in the purifying agent in example 11 was 15.3%, and the content of isopentenyl aldehyde in the purified isopentenyl alcohol was 14ppm.
Comparative example 1
2kg of the crude propylene oxide obtained in example 1 was weighed and fed into a rectifying apparatus, 1.146g of hydrazine hydrate was added, rectification was carried out, the overhead fraction was collected, and quantitative analysis was carried out by gas chromatography, whereby the acetaldehyde content in the purified propylene oxide was 67ppm.
Comparative example 2
2kg of the crude prenol obtained in example 9 was weighed and fed into a rectifying device, 0.601g of hydrazine hydrate was added, and the mixture was subjected to reduced pressure rectification, and the overhead fraction was collected, and quantitatively analyzed by gas chromatography, whereby the content of prenyl aldehyde in the purified prenol was 102ppm.
The above comparative examples 1 and 2 use only hydrazine hydrate as the purifying agent, and the purifying effect of using only hydrazine hydrate is significantly reduced as compared with examples 1 to 11. The content of acetaldehyde in the propylene oxide after purification in comparative example 1 was 67ppm, and the content of isopentenyl aldehyde in the isopentenol after purification in comparative example 2 was 102ppm, both higher than 20ppm.
The above-mentioned embodiments are merely for illustrating the technical concept and features of the present invention, and are not intended to limit the scope of the present invention to those skilled in the art to understand the present invention and implement the same. All equivalent changes or modifications made in accordance with the spirit of the present invention should be construed to be included in the scope of the present invention.
Claims (12)
1. The purification method of the compound containing the aldehyde impurities is characterized in that the compound containing the aldehyde impurities and a purifying agent are added into a rectifying tower to carry out rectification, and the top fraction is collected to obtain the compound with the aldehyde impurity content lower than 20 ppm; wherein the purifying agent comprises alkali metal borohydride and hydrazine hydrate, and the mole percentage of the alkali metal borohydride in the purifying agent is 2-20%;
wherein the compound is propylene oxide or 1, 2-butylene oxide; the aldehyde impurities are one or more of formaldehyde, acetaldehyde and propionaldehyde.
2. The purification method of the compound containing the aldehyde impurities is characterized in that the compound containing the aldehyde impurities and a purifying agent are added into a rectifying tower to carry out rectification, and the top fraction is collected to obtain the compound with the aldehyde impurity content lower than 20 ppm; wherein the purifying agent comprises alkali metal borohydride and hydrazine hydrate, and the mole percentage of the alkali metal borohydride in the purifying agent is 2-20%;
wherein the compound is isopentenyl alcohol, and the aldehyde impurity is isopentenyl aldehyde.
3. The method for purifying an aldehyde impurity-containing compound according to claim 1 or 2, wherein the molar percentage of the borohydride of an alkali metal in the purifying agent is 5 to 15%.
4. The method for purifying an aldehyde impurity-containing compound according to claim 1 or 2, wherein the hydrazine hydrate is contained in the purifying agent in a molar percentage of 80 to 98%.
5. A method for purifying a compound containing an aldehyde impurity as set forth in claim 3,
the mol percentage of the hydrazine hydrate in the purifying agent is 85% -95%.
6. The method for purifying an aldehyde impurity-containing compound according to claim 1 or 2, wherein the borohydride of an alkali metal is one or a combination of sodium borohydride and potassium borohydride.
7. The method for purifying an aldehyde impurity-containing compound according to claim 1 or 2, wherein the aldehyde impurity-containing compound is contained in an amount of 50 to 1000ppm.
8. The method for purifying an aldehyde impurity-containing compound according to claim 1 or 2, wherein the molar ratio of the purifying agent to the aldehyde impurity is (1 to 2): 1.
9. the method for purifying a compound containing an aldehyde impurity as claimed in claim 6,
the mole ratio of the purifying agent to the aldehyde impurities is (1-2): 1.
10. the method for purifying an aldehyde impurity-containing compound according to claim 1,
the propylene oxide is prepared by the reaction of propylene and hydrogen peroxide.
11. The method for purifying an aldehyde impurity-containing compound according to claim 1, wherein the 1, 2-epoxybutane is produced by reacting 1-butene with hydrogen peroxide.
12. The method for purifying an aldehyde impurity-containing compound according to claim 2, wherein the isopentenol is produced by isomerising 3-methyl-3-buten-1-ol.
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| CN104478771A (en) * | 2014-11-26 | 2015-04-01 | 东南大学 | Purification method of hindered-phenol efficient antioxidant |
| CN106397366B (en) * | 2015-08-03 | 2019-06-11 | 中国石油化工股份有限公司 | The purification process of propylene oxide |
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| CN101011661A (en) * | 2006-12-20 | 2007-08-08 | 中国日用化学工业研究院 | Catalyst for preparing fatty primary amine by fatty nitrile hydrogenation and application thereof |
| CN102491929A (en) * | 2011-12-08 | 2012-06-13 | 贵州省中国科学院天然产物化学重点实验室 | 1-hydroxy-2-ketopyrrolidine compound and preparation method and application thereof |
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| CN103341643A (en) * | 2013-07-26 | 2013-10-09 | 武汉理工大学 | Preparation method of composite reducing agent liquid phase for conductive composite particles coated with silver shell layers |
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