CN113651776A - Purifying agent for compound containing aldehyde impurities and application thereof - Google Patents
Purifying agent for compound containing aldehyde impurities and application thereof Download PDFInfo
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- C07—ORGANIC CHEMISTRY
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- C07D301/00—Preparation of oxiranes
- C07D301/32—Separation; Purification
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- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/56—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by isomerisation
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- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
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- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
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Abstract
The invention provides a purifying agent for a compound containing aldehyde impurities and application thereof. The purifying agent comprises borohydride and hydrazine hydrate of alkali metal, wherein the molar percentages of the borohydride and the hydrazine hydrate of the alkali metal are respectively 2-20% and 80-98%. The purifying agent is added in the rectification and purification process of the crude epoxy propane or the crude isoamylene alcohol containing 50-1000 ppm of aldehyde impurities, so that the content of the aldehyde impurities can be reduced to be below 20ppm, and the problems of low removal efficiency of the impurity aldehydes in the crude epoxy propane or the crude isoamylene alcohol and limited purity of the obtained product in the prior art are solved. The purifying agent provided by the invention has high impurity removal 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 the third largest propylene derivative second 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. The epoxypropane can also be used for preparing nonionic surfactants, propylene glycol, synthetic glycerol and the like. Propylene oxide-derived fine chemicals are used in almost all sectors of industry and in daily life. Although the reaction for producing propylene oxide by directly oxidizing propylene and hydrogen peroxide has high raw material conversion rate and selectivity of the product propylene oxide, because a large amount of solvent (such as methanol), water and excessive propylene exist in the reaction process, 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 the preparation of polyether polyols, and the polyether polyols thus obtained are in turn used as raw materials for the production of polyurethane foams. Propylene oxide for these applications must meet stringent purity requirements, wherein the aldehydes must all be below 100 ppm. For a few applications, it is even desirable to reduce the aldehyde impurity level to 20ppm or less, however, acetaldehyde and the like have boiling points close to those of propylene oxide, and thus it is difficult to separate them from propylene oxide by conventional distillation.
A number of patents disclose methods for purifying propylene oxide and US 3881996 discloses a method for purifying propylene oxide using multi-stage distillation, which is capable of purifying aldehydes in amounts less than 10ppm, but the distillation process is very energy intensive. Patent publication No. CN 101298443B discloses a process for purifying crude propene oxide containing methanol and acetaldehyde by means of continuously operated extractive distillation, which process comprises feeding an extraction solvent capable of reducing the volatility of methanol to a distillation column containing unsubstituted NH above the feed point of the crude propene oxide2A compound capable of reacting with acetaldehyde to obtain purified propylene oxide containing less than 100ppm methanol and less than 100ppm acetaldehyde, but less than 20ppm acetaldehyde. For most applications, it is desirable that the content of aldehyde impurities in the propylene oxide is less than 100ppm, and for a few applications, it is desirable to subject the propylene oxide to a treatmentThe content of aldehyde impurities in the alkane is reduced to below 20 ppm. Therefore, the development of an efficient and convenient method for removing the aldehyde impurities in the propylene oxide is of great significance.
The isopentenol, also known as 3-methyl-2-buten-1-ol, is an important organic synthesis intermediate, has wide application in the fields of pesticides, synthetic perfumes and the like, has an increasingly wide application range and greatly increases the demand with the continuous deepening of people on the synthesis process of the isopentenol, and therefore has important significance on the research on the synthesis technology of the isopentenol. The traditional method for producing the isopentenol comprises an isoprene method, wherein isoprene is taken as a raw material and is prepared through multiple steps of oxidation, acetification, saponification and the like, the process route is long, the product selectivity is low, and the environmental pollution is serious. In recent years, isobutene and formaldehyde are used as raw materials to prepare the isopentenol, the method is simple in process and low in pollution, isobutene and formaldehyde are condensed to obtain 3-methyl-3-butene-1-ol, the isopentenol is obtained through isomerization, however, in the isomerization reaction process, isopentenal can be generated, the boiling points of the isopentenal and the isopentenol are close and azeotropic, the quality of the isopentenal is seriously influenced by the existence of the isopentenal, and therefore, the content of the isopentenal is required to be reduced through a simple and effective method.
Disclosure of Invention
The invention solves the problems that the removal efficiency of impurity aldehydes in crude propylene oxide or crude isopentenol is low and the purity of the obtained product is limited 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 purifying agent is simple and cheap to prepare, and has excellent effect of removing impurity aldehydes in crude propylene oxide or crude prenol.
Specifically, the invention provides the following technical scheme:
in one aspect, the present invention provides a purification agent for a compound containing an aldehyde impurity, characterized in that the purification agent comprises a borohydride of an alkali metal and hydrazine hydrate.
Preferably, the purifying agent for the compound containing the aldehyde impurity is characterized in that the molar percentage of the alkali metal borohydride in the purifying agent is 2-20%, and more preferably 5-15%.
Preferably, the purifying agent for the compound containing the 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 for the compound containing the 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 for rectification, and the tower top fraction is collected to obtain the compound with the aldehyde impurity content of less than 20 ppm.
Preferably, the method for purifying a compound containing aldehyde impurities according to the present invention 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 a compound containing aldehyde impurities according to the present invention is characterized in that the compound is an isopentenol, and the aldehyde impurities are isopentenal.
Preferably, the method for purifying the compound containing the aldehyde impurities is characterized in that the content of the aldehyde impurities in the compound is 50-1000 ppm.
Preferably, the method for purifying a compound containing an aldehyde impurity according to the present invention is characterized in that the molar ratio of the purifying agent to the aldehyde impurity is (1 to 2): 1.
preferably, the method for purifying the compound containing the aldehyde impurities is characterized in that the propylene oxide is prepared by reacting propylene with hydrogen peroxide, and more preferably, the 1, 2-butylene oxide is prepared by reacting 1-butylene with hydrogen peroxide.
Preferably, the method for purifying a compound containing aldehyde impurities according to the present invention is characterized in that the prenol is obtained by isomerization of 3-methyl-3-buten-1-ol.
In another aspect, the present invention also provides the use of a purification agent as defined in any one of the above for the purification of a compound containing aldehyde impurities.
In another aspect, the present invention further provides the use of any one of the above-mentioned purifying agents in the field of purifying 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 removal rate of aldehydes, and can reduce the content of aldehyde impurities to below 20 ppm; the purifying agent provided by the invention can be applied to the purification process of propylene oxide and can also be applied to the purification of prenol.
Detailed Description
The invention provides a purifying agent of a compound containing aldehyde impurities and application thereof, aiming at solving the problems that in the prior art, the removal efficiency of the aldehyde impurities in crude propylene oxide or crude isopentenol is low and the purity of the obtained product is limited, wherein the purifying agent comprises borohydride and hydrazine hydrate of alkali metal, and the molar percentages of the borohydride and the hydrazine hydrate of the alkali metal in the purifying agent are respectively 2-20% and 80-98%. The purifying 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 content of the aldehyde impurities can be reduced to be below 20 ppm.
The reagents used in the examples of the present invention are shown in table 1 below. Unless otherwise specified, materials used in the examples were selected from any commercially available reagents or industrial products.
TABLE 1
| Reagent/instrument | Purity/type | Manufacturer of the product |
| Silica sol | The content of silicon oxide is 30 plus or minus 1 percent | QINGDAO HAIYANG CHEMICAL Co.,Ltd. |
| Sesbania powder | ＞98％ | Cyanine and sesbania powder Co Ltd of Dongying City |
| Hydrazine hydrate | ＞98％ | Aladdin |
| Sodium borohydride | ＞98％ | Aladdin |
| Potassium borohydride | ＞98％ | Aladdin |
| Propylene (PA) | ＞99％ | Daliangyong Feng gas Co Ltd |
| Hydrogen peroxide solution | H2O2The purity is 30-50% | Chemical industry of Dalianshengjia |
| Methanol | ＞99％ | Dalian Xinmu chemical Co Ltd |
| Strip extruding machine | Model DJ40 | ZIBO LINZI HAICHANG MACHINERY Co.,Ltd. |
The catalyst titanium-silicon molecular sieve used for the reaction of propylene and hydrogen peroxide is selected from self-made or commercially available, and the relative crystallinity of the titanium-silicon molecular sieve is more than 95 percent. For better illustration of the present invention, the preparation of the titanium silicalite molecular sieve is set forth, but is not limited to the titanium silicalite molecular sieve prepared by the following method.
The preparation method of the titanium silicalite TS-1 comprises the following steps: silica sol is used as a silicon source, tetrabutyl titanate is used as a titanium source, tetrapropyl ammonium bromide is used as a template agent, and the mass ratio of the silica sol to the tetrabutyl titanate to the tetrapropyl ammonium bromide is 91.5: 4:4.5, crystallizing the raw materials at the temperature of 150-. And (2) uniformly mixing the raw powder and sesbania powder, adding silica sol, further uniformly mixing, wherein the mass ratio of the sesbania powder to the raw powder to the silica sol is 1:16.5:82.5, extruding the mixture into strips by using a strip extruding machine for molding, drying the molded sample at 100 ℃ for 12 hours, and roasting at 500 ℃ for 4 hours to obtain the strip-shaped titanium-silicon molecular sieve TS-1.
The laboratory rectifying column used in the embodiment is a packing type rectifying column, a glass spring is filled, the height of the rectifying column is 80cm, the diameter of the rectifying column is 3cm, the rectifying is carried out under normal pressure or reduced pressure, and all substances are subjected to reflux separation under respective boiling points.
The present invention will be described in detail with reference to specific examples. Unless otherwise specified, all technical means used in the present invention are well known to those skilled in the art. The embodiments are to be considered as illustrative and not restrictive in character, the spirit and scope of the invention being limited only by the claims. It will be apparent to those skilled in the art that various changes or modifications in the components and amounts of the materials used in these embodiments can be made 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 a solvent methanol into a fixed bed reaction device filled with a titanium silicalite molecular sieve from bottom to top. Raw materials of propylene, hydrogen peroxide and a solvent of methanol are mixed according to a molar ratio of 3: 1: 6, the reaction temperature of a fixed bed is 50 ℃, and the reaction pressure is 3.0 MPa. The outlet product of the reactor contains unreacted raw material propylene, solvent methanol, product propylene oxide and 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 a crude propylene oxide product containing acetaldehyde impurities is separated from the top of the tower, and quantitative analysis of gas chromatography is applied to obtain that the acetaldehyde content in the crude propylene oxide is 504 ppm.
EXAMPLE 2 purification of crude propylene oxide
Weighing 2kg of the crude propylene oxide obtained in example 1, adding the crude propylene oxide into a rectifying device, adding 0.0433g of sodium borohydride and 1.089g of hydrazine hydrate, rectifying, collecting the fraction at the top of the tower, and carrying out quantitative analysis by gas chromatography, wherein the content of acetaldehyde in the purified propylene oxide is 12 ppm.
EXAMPLE 3 purification of crude propylene oxide
Weighing 2kg of the crude propylene oxide obtained in example 1, adding the crude propylene oxide into a rectifying device, adding 0.0520g of sodium borohydride and 1.307g of hydrazine hydrate, rectifying, collecting overhead fraction, and performing quantitative analysis by gas chromatography to obtain the purified propylene oxide containing 10ppm of acetaldehyde.
EXAMPLE 4 purification of crude propylene oxide
Weighing 2kg of the crude propylene oxide obtained in example 1, adding the crude propylene oxide into a rectifying device, adding 0.0693g of sodium borohydride and 1.055g of hydrazine hydrate, rectifying, collecting the fraction at the top of the tower, and performing quantitative analysis by gas chromatography to obtain the purified propylene oxide containing 10ppm of acetaldehyde.
EXAMPLE 5 purification of crude propylene oxide
Weighing 2kg of the crude propylene oxide obtained in example 1, adding the crude propylene oxide into a rectifying device, adding 0.0173g of sodium borohydride and 1.123g of hydrazine hydrate, rectifying, collecting the fraction at the top of the tower, and performing quantitative analysis by using a gas chromatograph to obtain the purified propylene oxide containing 15ppm of acetaldehyde.
EXAMPLE 6 purification of crude propylene oxide
Weighing 2kg of the crude propylene oxide obtained in example 1, adding the crude propylene oxide into a rectifying device, adding 0.0618g of potassium borohydride and 1.089g of hydrazine hydrate, rectifying, collecting overhead fraction, and performing quantitative analysis by gas chromatography to obtain the purified propylene oxide containing 11ppm of acetaldehyde.
Example 7 preparation of propylene oxide containing aldehyde impurities
Continuously introducing raw materials of propylene, hydrogen peroxide and a solvent methanol into a fixed bed reaction device filled with a titanium silicalite molecular sieve from bottom to top. Raw materials of propylene, hydrogen peroxide and solvent methanol are mixed according to a molar ratio of 3: 1: 4.5, the reaction temperature of a fixed bed is 40 ℃, and the reaction pressure is 3.0 MPa. The outlet product of the reactor contains unreacted raw material propylene, solvent methanol, product propylene oxide and 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 a crude propylene oxide product containing acetaldehyde impurities is separated from the top of the rectifying tower, and the acetaldehyde content in the crude propylene oxide is obtained by applying gas chromatography quantitative analysis, wherein the acetaldehyde content is 166 ppm.
EXAMPLE 8 purification of crude propylene oxide
2kg of the crude propylene oxide obtained in example 7 was weighed and added to a rectifying apparatus, and 0.0142g of sodium borohydride and 0.359g of hydrazine hydrate were added to conduct rectification, and a top fraction was collected and quantitatively analyzed by gas chromatography, and the acetaldehyde content in the purified propylene oxide was 9 ppm.
EXAMPLE 9 preparation of prenol containing aldehyde impurities
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 reaction tube is pressurized to 12mpa by using methanol, feeding is started, the mixed materials are fed by adopting a plunger pump, and the flow rate is as follows: 70g/h, controlling the reaction temperature to be 190 ℃, controlling the reaction pressure to be 12mpa, collecting reaction liquid, rectifying the obtained reaction liquid to obtain the isopentenol, wherein the product purity is more than 99%, and the content of the isopentenyl aldehyde in the crude isopentenol is 336ppm by applying gas chromatography quantitative analysis.
EXAMPLE 10 purification of crude prenol
Weighing 2kg of the crude prenol obtained in example 9, adding the crude prenol into a rectifying device, adding 0.0363g of sodium borohydride and 0.432g of hydrazine hydrate, performing reduced pressure rectification, collecting overhead fractions, and performing quantitative analysis by gas chromatography to obtain the purified prenol containing 18ppm of prenylaldehyde.
EXAMPLE 11 purification of crude prenol
Weighing 2kg of the crude prenol obtained in example 9, adding the crude prenol into a rectifying device, adding 0.0681g of sodium borohydride and 0.511g of hydrazine hydrate, performing reduced pressure rectification, collecting overhead fraction, and performing quantitative analysis by gas chromatography to obtain the purified prenylaldehyde content of the prenol of 14 ppm.
EXAMPLE 12 purification of crude propylene oxide
Weighing 2kg of the crude propylene oxide obtained in example 1, adding the crude propylene oxide into a rectifying device, adding 0.0086g of sodium borohydride and 1.134g of hydrazine hydrate, rectifying, collecting the fraction at the top of the tower, and performing quantitative analysis by gas chromatography to obtain the purified propylene oxide containing 33ppm of acetaldehyde.
EXAMPLE 13 purification of crude prenol
Weighing 2kg of the crude prenol obtained in example 9, adding the crude prenol into a rectifying device, adding 0.0036g of sodium borohydride and 0.475g of hydrazine hydrate, performing reduced pressure rectification, collecting overhead fractions, and performing quantitative analysis by gas chromatography to obtain the purified prenol containing 87ppm of prenal.
EXAMPLE 14 purification of crude propylene oxide
Weighing 2kg of the crude propylene oxide obtained in example 1, adding the crude propylene oxide into a rectifying device, adding 0.216g of sodium borohydride and 0.859g of hydrazine hydrate, rectifying, collecting overhead fraction, and performing quantitative analysis by gas chromatography to obtain the purified propylene oxide containing 10ppm of acetaldehyde.
In example 14 above, the mole percentage of sodium borohydride in the purifying agent is 25.1%, and the acetaldehyde content in the purified propylene oxide is 10 ppm; in the above example 3, the molar percentage of sodium borohydride in the purifying agent was 5.1%, and the acetaldehyde content in the purified propylene oxide was 10 ppm.
EXAMPLE 15 purification of crude prenol
Weighing 2kg of the crude prenol obtained in example 9, adding the crude prenol into a rectifying device, adding 0.0906g of sodium borohydride, adding 0.360g of hydrazine hydrate, performing reduced pressure rectification, collecting overhead fraction, and performing quantitative analysis by gas chromatography to obtain the purified prenylaldehyde content of the prenol of 13 ppm.
In the above example 15, the molar percentage of sodium borohydride in the purifying agent is 25.3%, and the content of prenylaldehyde in the purified prenol is 13 ppm; in the above example 11, the molar percentage of sodium borohydride in the purifying agent is 15.3%, and the content of prenylaldehyde in the purified prenol is 14 ppm.
Comparative example 1
2kg of the crude propylene oxide obtained in example 1 was weighed and added to a rectifying apparatus, 1.146g of hydrazine hydrate was added to conduct rectification, and a column top fraction was collected and quantitatively analyzed by gas chromatography, and the acetaldehyde content in the purified propylene oxide was 67 ppm.
Comparative example 2
Weighing 2kg of the crude prenol obtained in example 9, adding the crude prenol into a rectifying device, adding 0.601g of hydrazine hydrate, performing reduced pressure rectification, collecting overhead fractions, and performing quantitative analysis by gas chromatography to obtain purified prenylaldehyde content of 102 ppm.
The above comparative examples 1 and 2 use only hydrazine hydrate as a purification agent, and the purification effect using only hydrazine hydrate is significantly reduced as compared with examples 1 to 11. The content of acetaldehyde in the purified propylene oxide in the comparative example 1 is 67ppm, and the content of prenylaldehyde in the purified prenol in the comparative example 2 is 102ppm, which are both higher than 20 ppm.
The above-mentioned embodiments are only for illustrating the technical idea and features of the present invention, and the purpose of the present invention is to enable those skilled in the art to understand the content of the present invention and implement the present invention, and not to limit the protection scope of the present invention. All equivalent changes and modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.
Claims (13)
1. A purifying agent for a compound containing an aldehyde impurity, characterized in that the purifying agent comprises a borohydride of an alkali metal and hydrazine hydrate.
2. The purifying agent for compounds containing aldehyde impurities according to claim 1, wherein the molar percentage of the alkali metal borohydride in the purifying agent is 2 to 20%, preferably 5 to 15%.
3. The purification agent for a compound containing an aldehyde impurity according to claim 1 or 2, wherein the molar percentage of the hydrazine hydrate in the purification agent is 80 to 98%, preferably 85 to 95%.
4. A purifying agent for a compound containing aldehyde impurities according to any one of claims 1 to 3, wherein the borohydride of the alkali metal is one or a combination of two of sodium borohydride and potassium borohydride.
5. A method for purifying a compound containing aldehyde impurities, which is characterized in that the compound containing aldehyde impurities and the purifying agent of any one of the claims 1 to 4 are added into a rectifying tower for rectification, and a tower top fraction is collected to obtain the compound with the content of the aldehyde impurities lower than 20 ppm.
6. The process according to claim 5, characterized in that said compound is propylene oxide or 1, 2-butylene oxide, preferably propylene oxide; the aldehyde impurities are one or more of formaldehyde, acetaldehyde and propionaldehyde.
7. The method according to claim 5, wherein the compound is an isopentenol and the aldehyde impurity is an isopropenal.
8. The method for purifying a compound containing aldehyde impurities according to any one of claims 5 to 7, wherein the compound contains the aldehyde impurities in an amount of 50 to 1000 ppm.
9. The method for purifying a compound containing aldehyde impurities according to any one of claims 5 to 8, wherein the molar ratio of the purifying agent to the aldehyde impurities is (1 to 2): 1.
10. the method for purifying a compound containing aldehyde impurities according to claim 6, wherein the propylene oxide is prepared by reacting propylene with hydrogen peroxide, and preferably the 1, 2-butylene oxide is prepared by reacting 1-butene with hydrogen peroxide.
11. The method according to claim 7, wherein the prenol is obtained by isomerization of 3-methyl-3-buten-1-ol.
12. Use of a purification agent as claimed in any one of claims 1 to 4 for the purification of compounds containing aldehyde impurities.
13. Use of a purification agent as claimed in any one of claims 1 to 4 in the field of purification agents.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114276216A (en) * | 2022-01-05 | 2022-04-05 | 江苏扬农化工集团有限公司 | Method for removing aldehyde impurities in 1, 3-propylene glycol |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN101298443A (en) * | 2002-11-26 | 2008-11-05 | 德古萨股份公司 | Process for the purification of crude propene oxide |
| 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 |
| CN102911013A (en) * | 2012-11-09 | 2013-02-06 | 凯瑞化工股份有限公司 | Ethylene-glycolrefining method |
| 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 |
| CN103864723A (en) * | 2014-03-18 | 2014-06-18 | 中国石油集团东北炼化工程有限公司吉林设计院 | Technology for purifying epoxypropane |
| CN104478771A (en) * | 2014-11-26 | 2015-04-01 | 东南大学 | Purification method of hindered-phenol efficient antioxidant |
| CN106397366A (en) * | 2015-08-03 | 2017-02-15 | 中国石油化工股份有限公司 | Purifying method for epoxypropane |
-
2021
- 2021-08-06 CN CN202110903837.7A patent/CN113651776B/en active Active
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101298443A (en) * | 2002-11-26 | 2008-11-05 | 德古萨股份公司 | Process for the purification of crude propene oxide |
| 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 |
| CN102911013A (en) * | 2012-11-09 | 2013-02-06 | 凯瑞化工股份有限公司 | Ethylene-glycolrefining method |
| 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 |
| CN103864723A (en) * | 2014-03-18 | 2014-06-18 | 中国石油集团东北炼化工程有限公司吉林设计院 | Technology for purifying epoxypropane |
| CN104478771A (en) * | 2014-11-26 | 2015-04-01 | 东南大学 | Purification method of hindered-phenol efficient antioxidant |
| CN106397366A (en) * | 2015-08-03 | 2017-02-15 | 中国石油化工股份有限公司 | Purifying method for epoxypropane |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114276216A (en) * | 2022-01-05 | 2022-04-05 | 江苏扬农化工集团有限公司 | Method for removing aldehyde impurities in 1, 3-propylene glycol |
| CN114276216B (en) * | 2022-01-05 | 2023-08-01 | 江苏扬农化工集团有限公司 | Method for removing aldehyde impurities in 1, 3-propylene glycol |
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|---|---|
| CN113651776B (en) | 2023-10-17 |
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