CN113880696A - Separation and purification method of m-cresol and p-cresol - Google Patents

Separation and purification method of m-cresol and p-cresol Download PDF

Info

Publication number
CN113880696A
CN113880696A CN202111175795.6A CN202111175795A CN113880696A CN 113880696 A CN113880696 A CN 113880696A CN 202111175795 A CN202111175795 A CN 202111175795A CN 113880696 A CN113880696 A CN 113880696A
Authority
CN
China
Prior art keywords
cresol
tower
gas
reaction
liquid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN202111175795.6A
Other languages
Chinese (zh)
Inventor
王乃超
王胜利
雷绍奇
闫丙辰
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shaanxi Wanhui Nengju Technology Co ltd
Original Assignee
Shaanxi Wanhui Nengju Technology Co ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shaanxi Wanhui Nengju Technology Co ltd filed Critical Shaanxi Wanhui Nengju Technology Co ltd
Priority to CN202111175795.6A priority Critical patent/CN113880696A/en
Publication of CN113880696A publication Critical patent/CN113880696A/en
Pending legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/685Processes comprising at least two steps in series
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/70Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/70Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
    • C07C37/74Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/70Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
    • C07C37/82Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by solid-liquid treatment; by chemisorption
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C37/00Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
    • C07C37/68Purification; separation; Use of additives, e.g. for stabilisation
    • C07C37/86Purification; separation; Use of additives, e.g. for stabilisation by treatment giving rise to a chemical modification

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention belongs to the technical field of separation and purification of chemical products, and particularly relates to a separation and purification method of m-cresol and p-cresol, which comprises the following steps: 1) adding meta-para-mixed phenol and a liquid acid catalyst into an alkylation reaction container at one time, introducing the meta-para-mixed phenol and the liquid acid catalyst into a gas-liquid reaction tower from a liquid inlet pipe when the temperature rises to 60 ℃, simultaneously introducing isobutene gas into the gas-liquid reaction tower from a gas inlet pipe, and contacting the meta-para-mixed phenol and the liquid acid catalyst to perform alkylation reaction; 2) introducing the obtained alkylation product into a catalyst adsorption tower, a light component removal tower and a rectifying tower in sequence, and rectifying and collecting fractions with different temperatures; 3) and respectively placing the target fractions into a dealkylation reaction vessel, and adding a dealkylation catalyst for reaction to obtain a final product. The method utilizes the gas-liquid reaction tower to realize the alkylation reaction of the alkylating agent and the mixed m-cresol and p-cresol, so that the isobutene can be fully contacted with the atomized raw material, the conversion rate of the mixed phenol and the utilization rate of the isobutene are improved, and the problems of high energy consumption and potential safety hazard caused by liquefying the alkylating agent are effectively avoided.

Description

Separation and purification method of m-cresol and p-cresol
Technical Field
The invention belongs to the technical field of separation and purification of chemical products, and particularly relates to a separation and purification method of m-cresol and p-cresol.
Background
Cresol is an organic chemical intermediate with a wide range of uses. Wherein, the paracresol can be used in the industrial departments of pesticide, dye, plastic, medicine, and the like. M-cresol is an important raw material for synthesizing organic intermediates, and has important application in color film developers, synthetic resins, adhesives and the like. Therefore, the high-purity m-cresol and p-cresol have good market prospect and great development potential, and have extremely important influence on the development of economy and chemical industry in China. However, although the separation of m-cresol and p-cresol by alkylation process has been done in China, the method still has many defects, and industrial production cannot be realized. Therefore, the realization of the industrialization of m-cresol and p-cresol is very important at present. At present, the domestic technology for separating m-cresol and p-cresol mostly adopts an intermittent reaction kettle, and high-purity isobutene and mixed m-cresol and p-cresol are subjected to gas-phase alkylation reaction to obtain an alkylation product, and then the high-purity m-cresol and p-cresol are obtained through separation.
Patent specification CN106810422A discloses a method for separating m-cresol and p-cresol by liquid phase alkylation. The method utilizes a new process that the isobutene mixed gas and the m-cresol and p-cresol mixture are subjected to alkylation reaction and separation in a fixed bed reactor under the liquid phase state at the same time to obtain the m-cresol and the p-cresol, and the pure m-cresol and p-cresol are obtained by taking the isobutene mixed gas as an alkylating agent and the m-cresol and p-cresol mixture as raw materials through liquid phase alkylation reaction and separation. The method overcomes the defects of low utilization rate of an alkylating agent and serious environmental pollution in the gas-phase alkylation reaction in the prior art, and simultaneously overcomes the defect of high production cost caused by using high-purity isobutene as the alkylating agent in the gas-phase alkylation reaction.
However, the method for separating m-cresol and p-cresol by alkylation still has the defects that the method consumes more energy for liquefying isobutene, so that the integral separation and purification cost is higher, and the potential safety hazard is increased due to high pressure.
Disclosure of Invention
The invention aims to overcome the problems in the prior art and provide a method for separating and purifying m-cresol and p-cresol.
In order to achieve the technical purpose and achieve the technical effect, the invention is realized by the following technical scheme:
a method for separating and purifying m-cresol and p-cresol comprises the following steps:
1) adding the m-p-cresol and the liquid acid catalyst into an alkylation reaction container at one time, starting stirring and heating, introducing the mixture into a gas-liquid reaction tower from a liquid inlet pipe when the temperature rises to 60 ℃, simultaneously introducing isobutene gas into the gas-liquid reaction tower from a gas inlet pipe, contacting the isobutene gas with the atomized m-p-cresol and the liquid acid catalyst for alkylation reaction, and circularly and continuously introducing the isobutene gas for reaction until all m-p-cresol in the raw materials is converted into an alkylation product;
2) introducing the obtained alkylation product into a catalyst adsorption tower, adsorbing and removing the catalyst by the catalyst adsorption tower, feeding the feed liquid passing through the catalyst adsorption tower into a light component removal tower, and removing dissolved isobutene by the light component removal tower; transferring the bottom material of the light component removal tower to a rectifying tower, heating and rectifying the rectifying tower under the pressure condition of 5-15kPa, collecting fractions with different temperatures, wherein the working temperature of the rectifying tower is 150-;
3) and respectively placing the target fraction into a dealkylation reaction vessel, adding a dealkylation catalyst, heating and stirring, heating to 120-150 ℃, maintaining for 5-7 hours, and then finishing the reaction to obtain the final product, namely the p-cresol or the m-cresol.
Further, in the method for separating and purifying m-cresol and p-cresol as described above, in step 1), the liquid acid catalyst is benzenesulfonic acid or a benzenesulfonic acid homologue.
Further, in the method for separating and purifying m-cresol and p-cresol as described above, in the step 1), the internal environment of the gas-liquid reaction tower is preheated to 60 ℃ before the raw material is introduced into the gas-liquid reaction tower.
Further, in the method for separating and purifying m-cresol and p-cresol as described above, in the step 1), the temperature of the reaction system of the gas-liquid reaction tower is kept below 90 ℃ during the alkylation reaction.
Further, in the method for separating and purifying m-cresol and p-cresol as described above, in the step 1), the gas inlet pipe of the gas-liquid reaction tower maintains a slight negative pressure capable of inhibiting the formation of oligomers due to the self-polymerization of isobutylene gas during the alkylation reaction.
Further, in the method for separating and purifying m-cresol and p-cresol as described above, in step 1), the alkylation product is a substituted derivative: 2, 6-di-tert-butyl-p-cresol and 4, 6-di-tert-butyl-m-cresol.
Further, in the method for separating and purifying m-cresol and p-cresol as described above, in the step 2), the adsorption tower is periodically desorbed by water, and then the liquid acid catalyst is recovered by concentration.
Further, in the method for separating and purifying m-cresol and p-cresol, in the step 2), the working pressure of the lightness-removing tower is 5-15kPa, and the working temperature is less than or equal to 150 ℃.
Further, in the method for separating and purifying m-cresol and p-cresol, step 2), 2, 6-di-tert-butyl-p-cresol and 4, 6-di-tert-butyl-m-cresol with high purity can be obtained at the top of the rectifying tower.
Further, in the method for separating and purifying m-cresol and p-cresol as described above, in step 3), the dealkylation catalyst is methyl benzenesulfonic acid or a mesoporous molecular sieve catalyst.
The invention has the beneficial effects that:
the invention utilizes the gas-liquid reaction tower to realize the alkylation reaction of the alkylating agent and the mixed m-cresol and p-cresol, so that the isobutene can be fully contacted with the atomized raw material, the contact area of the isobutene and the atomized raw material is increased, the conversion rate of the mixed phenol and the utilization rate of the isobutene are improved, and the problems of high energy consumption and potential safety hazard caused by liquefying the alkylating agent are effectively avoided.
Of course, it is not necessary for any one product that embodies the invention to achieve all of the above advantages simultaneously.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The liquid acid catalyst is benzenesulfonic acid or its homologue.
The dealkylation catalyst is methyl benzene sulfonic acid or mesoporous molecular sieve catalyst.
The following embodiments are relevant to the present invention:
example 1
A method for separating and purifying m-cresol and p-cresol is characterized by comprising the following steps:
1) adding meta-para-phenol and a liquid acid catalyst into an alkylation reaction container at one time, starting stirring and heating, introducing the mixture into a gas-liquid reaction tower from a liquid inlet pipe when the temperature rises to 60 ℃, simultaneously introducing isobutene gas into the gas-liquid reaction tower from a gas inlet pipe, and preheating the internal environment of the gas-liquid reaction tower to 60 ℃ before introducing raw materials. In the alkylation reaction process, the temperature of the reaction system of the gas-liquid reaction tower is kept below 90 ℃, and the gas inlet pipe of the gas-liquid reaction tower maintains a slight negative pressure capable of inhibiting the isobutene gas from self-polymerizing to form oligomers. The isobutene gas contacts the atomized meta-para-phenol and the liquid acid catalyst to carry out alkylation reaction, and the isobutene gas is circularly and continuously introduced for reaction until all the meta-para-cresol in the raw material is converted into an alkylation product; the alkylation product is a substituted derivative: 2, 6-di-tert-butyl-p-cresol and 4, 6-di-tert-butyl-m-cresol;
2) introducing the obtained alkylation product into a catalyst adsorption tower, adsorbing and removing the catalyst by the catalyst adsorption tower, desorbing by using water periodically by the adsorption tower, and concentrating and recovering the liquid acid catalyst.
The feed liquid passing through the catalyst adsorption tower enters a light component removal tower, and dissolved isobutene is removed by the light component removal tower; the working pressure of the lightness-removing tower is 10kPa, and the working temperature is less than or equal to 150 ℃.
Transferring the bottom material of the light component removal tower to a rectifying tower, heating and rectifying the rectifying tower under the pressure condition of 10kPa, collecting fractions with different temperatures, wherein the working temperature of the rectifying tower is 150-; 2, 6-di-tert-butyl-p-cresol and 4, 6-di-tert-butyl-m-cresol with high purity can be obtained at the top of the rectifying tower;
3) and respectively placing the target fractions into a dealkylation reaction vessel, adding a dealkylation catalyst, heating and stirring, heating to 130 ℃, maintaining for 6 hours, and finishing the reaction to obtain the final product, namely the p-cresol or the m-cresol.
Example 2
A method for separating and purifying m-cresol and p-cresol is characterized by comprising the following steps:
1) adding meta-para-phenol and a liquid acid catalyst into an alkylation reaction container at one time, starting stirring and heating, introducing the mixture into a gas-liquid reaction tower from a liquid inlet pipe when the temperature rises to 60 ℃, simultaneously introducing isobutene gas into the gas-liquid reaction tower from a gas inlet pipe, and preheating the internal environment of the gas-liquid reaction tower to 60 ℃ before introducing raw materials. In the alkylation reaction process, the temperature of the reaction system of the gas-liquid reaction tower is kept below 90 ℃, and the gas inlet pipe of the gas-liquid reaction tower maintains a slight negative pressure capable of inhibiting the isobutene gas from self-polymerizing to form oligomers. The isobutene gas contacts the atomized meta-para-phenol and the liquid acid catalyst to carry out alkylation reaction, and the isobutene gas is circularly and continuously introduced for reaction until all the meta-para-cresol in the raw material is converted into an alkylation product; the alkylation product is a substituted derivative: 2, 6-di-tert-butyl-p-cresol and 4, 6-di-tert-butyl-m-cresol;
2) introducing the obtained alkylation product into a catalyst adsorption tower, adsorbing and removing the catalyst by the catalyst adsorption tower, desorbing by using water periodically by the adsorption tower, and concentrating and recovering the liquid acid catalyst.
The feed liquid passing through the catalyst adsorption tower enters a light component removal tower, and dissolved isobutene is removed by the light component removal tower; the working pressure of the lightness-removing tower is 5kPa, and the working temperature is less than or equal to 150 ℃.
Transferring the bottom material of the light component removal tower to a rectifying tower, heating and rectifying the rectifying tower under the pressure condition of 5kPa, collecting fractions with different temperatures, wherein the working temperature of the rectifying tower is 150-; 2, 6-di-tert-butyl-p-cresol and 4, 6-di-tert-butyl-m-cresol with high purity can be obtained at the top of the rectifying tower;
3) and respectively placing the target fractions into a dealkylation reaction vessel, adding a dealkylation catalyst, heating and stirring, heating to 120 ℃, maintaining for 5-7 hours, and finishing the reaction to obtain the final product, namely the p-cresol or the m-cresol.
Example 2
A method for separating and purifying m-cresol and p-cresol is characterized by comprising the following steps:
1) adding meta-para-phenol and a liquid acid catalyst into an alkylation reaction container at one time, starting stirring and heating, introducing the mixture into a gas-liquid reaction tower from a liquid inlet pipe when the temperature rises to 60 ℃, simultaneously introducing isobutene gas into the gas-liquid reaction tower from a gas inlet pipe, and preheating the internal environment of the gas-liquid reaction tower to 60 ℃ before introducing raw materials. In the alkylation reaction process, the temperature of the reaction system of the gas-liquid reaction tower is kept below 90 ℃, and the gas inlet pipe of the gas-liquid reaction tower maintains a slight negative pressure capable of inhibiting the isobutene gas from self-polymerizing to form oligomers. The isobutene gas contacts the atomized meta-para-phenol and the liquid acid catalyst to carry out alkylation reaction, and the isobutene gas is circularly and continuously introduced for reaction until all the meta-para-cresol in the raw material is converted into an alkylation product; the alkylation product is a substituted derivative: 2, 6-di-tert-butyl-p-cresol and 4, 6-di-tert-butyl-m-cresol;
2) introducing the obtained alkylation product into a catalyst adsorption tower, adsorbing and removing the catalyst by the catalyst adsorption tower, desorbing by using water periodically by the adsorption tower, and concentrating and recovering the liquid acid catalyst.
The feed liquid passing through the catalyst adsorption tower enters a light component removal tower, and dissolved isobutene is removed by the light component removal tower; the working pressure of the lightness-removing tower is 15kPa, and the working temperature is less than or equal to 150 ℃.
Transferring the bottom material of the light component removal tower to a rectifying tower, heating and rectifying the rectifying tower under the pressure condition of 15kPa, collecting fractions with different temperatures, wherein the working temperature of the rectifying tower is 150-; 2, 6-di-tert-butyl-p-cresol and 4, 6-di-tert-butyl-m-cresol with high purity can be obtained at the top of the rectifying tower;
3) and respectively placing the target fractions into a dealkylation reaction vessel, adding a dealkylation catalyst, heating and stirring, heating to 150 ℃, maintaining for 7 hours, and finishing the reaction to obtain the final product, namely the p-cresol or the m-cresol.
The preferred embodiments of the invention disclosed above are intended to be illustrative only. The preferred embodiments are not intended to be exhaustive or to limit the invention to the precise embodiments disclosed. Obviously, many modifications and variations are possible in light of the above teaching. The embodiments were chosen and described in order to best explain the principles of the invention and the practical application, to thereby enable others skilled in the art to best utilize the invention. The invention is limited only by the claims and their full scope and equivalents.

Claims (10)

1. A method for separating and purifying m-cresol and p-cresol is characterized by comprising the following steps:
1) adding the m-p-cresol and the liquid acid catalyst into an alkylation reaction container at one time, starting stirring and heating, introducing the mixture into a gas-liquid reaction tower from a liquid inlet pipe when the temperature rises to 60 ℃, simultaneously introducing isobutene gas into the gas-liquid reaction tower from a gas inlet pipe, contacting the isobutene gas with the atomized m-p-cresol and the liquid acid catalyst for alkylation reaction, and circularly and continuously introducing the isobutene gas for reaction until all m-p-cresol in the raw materials is converted into an alkylation product;
2) introducing the obtained alkylation product into a catalyst adsorption tower, adsorbing and removing the catalyst by the catalyst adsorption tower, feeding the feed liquid passing through the catalyst adsorption tower into a light component removal tower, and removing dissolved isobutene by the light component removal tower; transferring the bottom material of the light component removal tower to a rectifying tower, heating and rectifying the rectifying tower under the pressure condition of 5-15kPa, collecting fractions with different temperatures, wherein the working temperature of the rectifying tower is 150-;
3) and respectively placing the target fraction into a dealkylation reaction vessel, adding a dealkylation catalyst, heating and stirring, heating to 120-150 ℃, maintaining for 5-7 hours, and then finishing the reaction to obtain the final product, namely the p-cresol or the m-cresol.
2. The method for separating and purifying m-cresol and p-cresol as claimed in claim 1, wherein the purification step comprises the following steps: in the step 1), the liquid acid catalyst is benzene sulfonic acid or benzene sulfonic acid homologues.
3. The method for separating and purifying m-cresol and p-cresol as claimed in claim 1, wherein the purification step comprises the following steps: in the step 1), the internal environment of the gas-liquid reaction tower is preheated to 60 ℃ before the raw materials are introduced.
4. The method for separating and purifying m-cresol and p-cresol as claimed in claim 1, wherein the purification step comprises the following steps: in the step 1), in the alkylation reaction process, the temperature of a reaction system of the gas-liquid reaction tower is kept below 90 ℃.
5. The method for separating and purifying m-cresol and p-cresol as claimed in claim 1, wherein the purification step comprises the following steps: in the step 1), in the alkylation reaction process, the gas inlet pipe of the gas-liquid reaction tower maintains a slight negative pressure capable of inhibiting the isobutene gas from self-polymerizing to form oligomers.
6. The method for separating and purifying m-cresol and p-cresol as claimed in claim 1, wherein the purification step comprises the following steps: in step 1), the alkylation product is a substituted derivative: 2, 6-di-tert-butyl-p-cresol and 4, 6-di-tert-butyl-m-cresol.
7. The method for separating and purifying m-cresol and p-cresol as claimed in claim 1, wherein the purification step comprises the following steps: in the step 2), the adsorption tower is used for desorption by water periodically, and then the liquid acid catalyst is recovered by concentration.
8. The method for separating and purifying m-cresol and p-cresol as claimed in claim 1, wherein the purification step comprises the following steps: in the step 2), the working pressure of the lightness-removing tower is 5-15kPa, and the working temperature is less than or equal to 150 ℃.
9. The method for separating and purifying m-cresol and p-cresol as claimed in claim 1, wherein the purification step comprises the following steps: in the step 2), high-purity 2, 6-di-tert-butyl-p-cresol and 4, 6-di-tert-butyl-m-cresol can be obtained at the top of the rectifying tower.
10. The method for separating and purifying m-cresol and p-cresol as claimed in claim 1, wherein the purification step comprises the following steps: in the step 3), the dealkylation catalyst is methyl benzenesulfonic acid or a mesoporous molecular sieve catalyst.
CN202111175795.6A 2021-10-09 2021-10-09 Separation and purification method of m-cresol and p-cresol Pending CN113880696A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202111175795.6A CN113880696A (en) 2021-10-09 2021-10-09 Separation and purification method of m-cresol and p-cresol

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202111175795.6A CN113880696A (en) 2021-10-09 2021-10-09 Separation and purification method of m-cresol and p-cresol

Publications (1)

Publication Number Publication Date
CN113880696A true CN113880696A (en) 2022-01-04

Family

ID=79005734

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202111175795.6A Pending CN113880696A (en) 2021-10-09 2021-10-09 Separation and purification method of m-cresol and p-cresol

Country Status (1)

Country Link
CN (1) CN113880696A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024108895A1 (en) * 2022-11-23 2024-05-30 江苏迈达新材料股份有限公司 Recycling and reusing method for heavy alkylphenol

Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1313270A (en) * 2000-03-13 2001-09-19 锦州石化天元集团公司 Process for preparing 2,6-di-tear-butyl p-cresol
CN101353293A (en) * 2008-07-16 2009-01-28 天津天大天海化工新技术有限公司 Method for producing 2-tertiary butyl-p-cresol and 6-tertiary butyl-m-cresol
CN101857529A (en) * 2010-06-07 2010-10-13 吴鸿宾 Method for preparing chemical intermediates by using mixed o/m/p-cresol
CN101863742A (en) * 2010-06-07 2010-10-20 吴鸿宾 Separation method of m-cresol and p-cresol mixture
CN102311318A (en) * 2010-06-29 2012-01-11 如皋市金陵化工有限公司 Processing technique of 2,6-ditbutyl-4-methylphenol
CN102898281A (en) * 2012-11-06 2013-01-30 孙浩翔 Method for co-producing 2, 6-butylated hydroxytoluene and m-cresol as well 6-tertiry butyl m-cresol by utilizing cresol mixture
CN103212438A (en) * 2013-05-02 2013-07-24 天津北洋国精科技股份有限公司 Catalyst for alkylation separation of m-cresol and p-cresol and separation method
CN104474731A (en) * 2014-11-27 2015-04-01 天津天大天海化工新技术有限公司 Reactive distillation column and method for reactive distillation and pyrolysis of alkylphenol
CN104496758A (en) * 2014-12-02 2015-04-08 安徽海华科技股份有限公司 M-cresol and p-cresol alkylated continuous reaction method
CN106810422A (en) * 2017-01-16 2017-06-09 河北工业大学 A kind of method that liquid-phase alkylation method separates M-and P-cresols
CN108250048A (en) * 2016-12-29 2018-07-06 湖南长岭石化科技开发有限公司 A kind of method for detaching metacresol and paracresol and a kind of hydrocarbylation process and a kind of cleavage method
CN111393266A (en) * 2020-02-21 2020-07-10 江苏迈达新材料股份有限公司 BHT alkylation tail gas isobutene recovery process
CN111960925A (en) * 2020-07-23 2020-11-20 安徽海华科技有限公司 Preparation method of 2, 6-di-tert-butyl-p-cresol

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1313270A (en) * 2000-03-13 2001-09-19 锦州石化天元集团公司 Process for preparing 2,6-di-tear-butyl p-cresol
CN101353293A (en) * 2008-07-16 2009-01-28 天津天大天海化工新技术有限公司 Method for producing 2-tertiary butyl-p-cresol and 6-tertiary butyl-m-cresol
CN101857529A (en) * 2010-06-07 2010-10-13 吴鸿宾 Method for preparing chemical intermediates by using mixed o/m/p-cresol
CN101863742A (en) * 2010-06-07 2010-10-20 吴鸿宾 Separation method of m-cresol and p-cresol mixture
CN102311318A (en) * 2010-06-29 2012-01-11 如皋市金陵化工有限公司 Processing technique of 2,6-ditbutyl-4-methylphenol
CN102898281A (en) * 2012-11-06 2013-01-30 孙浩翔 Method for co-producing 2, 6-butylated hydroxytoluene and m-cresol as well 6-tertiry butyl m-cresol by utilizing cresol mixture
CN103212438A (en) * 2013-05-02 2013-07-24 天津北洋国精科技股份有限公司 Catalyst for alkylation separation of m-cresol and p-cresol and separation method
CN104474731A (en) * 2014-11-27 2015-04-01 天津天大天海化工新技术有限公司 Reactive distillation column and method for reactive distillation and pyrolysis of alkylphenol
CN104496758A (en) * 2014-12-02 2015-04-08 安徽海华科技股份有限公司 M-cresol and p-cresol alkylated continuous reaction method
CN108250048A (en) * 2016-12-29 2018-07-06 湖南长岭石化科技开发有限公司 A kind of method for detaching metacresol and paracresol and a kind of hydrocarbylation process and a kind of cleavage method
CN106810422A (en) * 2017-01-16 2017-06-09 河北工业大学 A kind of method that liquid-phase alkylation method separates M-and P-cresols
CN111393266A (en) * 2020-02-21 2020-07-10 江苏迈达新材料股份有限公司 BHT alkylation tail gas isobutene recovery process
CN111960925A (en) * 2020-07-23 2020-11-20 安徽海华科技有限公司 Preparation method of 2, 6-di-tert-butyl-p-cresol

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024108895A1 (en) * 2022-11-23 2024-05-30 江苏迈达新材料股份有限公司 Recycling and reusing method for heavy alkylphenol

Similar Documents

Publication Publication Date Title
CN106810422A (en) A kind of method that liquid-phase alkylation method separates M-and P-cresols
CN101429288A (en) Method for treating process liquid generated in production process of polyphenylene sulfide
US11667597B2 (en) Method for linkage recovery of organic acid in aqueous organic acid solution
CN111039832A (en) Method for producing taurine and method for removing impurities from reaction system for preparing taurine
CN102276483A (en) Production method of oamino pheylmethyl ether
CN102898281A (en) Method for co-producing 2, 6-butylated hydroxytoluene and m-cresol as well 6-tertiry butyl m-cresol by utilizing cresol mixture
CN113880696A (en) Separation and purification method of m-cresol and p-cresol
CN101121709B (en) Primary concentration and purification method for trioxymethylene after synthesizing
CN113120925B (en) Method for recovering iodide from isophorone cracking material
CN108947774B (en) Method and device for separating isopropanol
CN108640844B (en) Method for recovering triethylamine from industrial wastewater
CN110613946A (en) Backpack reaction rectification equipment for synthesizing diethyl oxalate and process thereof
CN114213217A (en) Production method and application of p-phenylphenol
WO2013004026A1 (en) Process for preparing ethanolamine hydrochloride and co-product ethanolamine
CN110668956B (en) Method for desalting and purifying water phase through water washing extraction in RT base production process
CN104119225A (en) New technology for producing ethyl acetate through reactive distillation by taking mixed ionic liquid as catalyst
CN113698278B (en) Method for extracting 3, 5-xylenol from 3, 5-xylenol/m-p-ethylphenol
CN109665995B (en) Refining method of caprolactam crude product and preparation method of caprolactam
CN109336728A (en) A kind of process for effectively purifying of 1,2,4,5- durene
CN111072437A (en) Method for preparing isobutene by catalytic cracking of tert-butyl methyl phenol
CN111909004A (en) Method for separating m-cresol from p-cresol
CN101343230B (en) 2,4-dinitrophenol inhibitor purification process
CN111517962B (en) Preparation method of amine anti-aging agent
CN114405053A (en) Method for crystallizing manganese sulfate solution based on ethanol method
CN110372521A (en) A method of the stripping recycling pentanediamine from the water phase containing pentanediamine

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
RJ01 Rejection of invention patent application after publication

Application publication date: 20220104

RJ01 Rejection of invention patent application after publication