CN114478199A - Method for producing nonyl phenol - Google Patents
Method for producing nonyl phenol Download PDFInfo
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- CN114478199A CN114478199A CN202210326247.7A CN202210326247A CN114478199A CN 114478199 A CN114478199 A CN 114478199A CN 202210326247 A CN202210326247 A CN 202210326247A CN 114478199 A CN114478199 A CN 114478199A
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- Prior art keywords
- mixture
- phenol
- temperature
- mixer
- nonene
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- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 title claims abstract description 35
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 21
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 50
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000000463 material Substances 0.000 claims abstract description 29
- 238000005580 one pot reaction Methods 0.000 claims abstract description 10
- 239000002994 raw material Substances 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 48
- 238000005804 alkylation reaction Methods 0.000 claims description 16
- 239000011347 resin Substances 0.000 claims description 10
- 229920005989 resin Polymers 0.000 claims description 10
- 230000029936 alkylation Effects 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 125000002091 cationic group Chemical group 0.000 claims description 8
- 239000010409 thin film Substances 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 3
- 238000005265 energy consumption Methods 0.000 abstract description 5
- 239000006227 byproduct Substances 0.000 abstract description 2
- -1 phenol nonene Chemical compound 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000002957 persistent organic pollutant Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for producing nonyl phenol, which comprises the following steps: inputting phenol and nonene into a mixer according to the proportion of 3.2-4:1.4, and circulating the mixed raw materials by using a pump machine to fully and uniformly mix the phenol and the nonene. In the method, because the reaction is exothermic, the reacted materials are continuously input into the mixer in proportion and mixed with the phenol nonene to absorb the reaction heat of the materials, the reaction heat can be better utilized to improve the temperature of the materials in the mixing tank, the energy consumption is more effectively reduced, the whole production process is continuously carried out, only one-step reaction is needed, the energy consumption is low, the byproducts are less, the quality is good, and the production efficiency is high.
Description
Technical Field
The invention relates to the technical field of compound preparation, in particular to a method for producing nonyl phenol.
Background
Nonyl phenol is an important fine chemical raw material and intermediate, is colorless or light yellow liquid at normal temperature, has slight phenol smell, is insoluble in water and is soluble in acetone. The method is mainly used for producing surfactants, and is also used in the fields of antioxidants, textile printing and dyeing auxiliaries, lubricating oil additives, pesticide emulsifiers, resin modifiers, resins, rubber stabilizers and the like. Nonyl phenol is an organic pollutant and is called "sperm killer".
The existing nonyl phenol is often complex in production process, various materials are often added in the production process for preparation, the energy consumption is high, the product is less, and more other additional products are contained.
Disclosure of Invention
Based on the technical problems in the background art, the invention provides a method for producing nonyl phenol.
The invention provides a method for producing nonyl phenol, which comprises the following steps:
step one, mixing uniformly: inputting phenol and nonene into a mixer according to the proportion of 3.2-4:1.4, and circulating the mixed raw materials by using a pump machine to fully and uniformly mix the phenol and the nonene;
step two, preheating treatment: after phenol and nonene are uniformly mixed in proportion, the mixture is subjected to preheating treatment, the temperature of the mixture is raised to the range of 98 +/-2 ℃ by using related heating equipment, phenol and nonene are continuously input into a mixer during the preheating treatment, the mixture is conveyed by a pump and subjected to circulating reflux mixing, and the next treatment is carried out when the preheating temperature is stabilized at 98 +/-2 ℃.
Step three: and (3) alkylation reaction treatment: after the preheating temperature of the mixture is stable, inputting the mixture into a reactor filled with a cationic resin catalyst, performing alkylation one-step reaction when the mixture enters the reactor, returning part of the reacted materials to the mixer, separating light and heavy components of the reacted materials by a thin film evaporator, circulating the light components to the mixer, removing phenol from the heavy components by a dephenolizing rectifying tower, and separating high-purity nonylphenol from the dephenolized crude nonylphenol by a finished product rectifying tower.
2. The method for producing nonyl phenol of claim 1, wherein in step one, the mixed raw materials are circulated by a pump, so that phenol and nonene are mixed uniformly.
3. The method of claim 1, wherein the mixture is preheated by raising the temperature to 50-55 ℃, continuing the preliminary preheating, raising the preheating temperature to 98 ± 2 ℃, and controlling the preheating temperature to 98 ± 2 ℃ in the second step.
4. The method for producing nonylphenol as claimed in claim 1, wherein in step three, after the preheating temperature of the mixture is stabilized during the alkylation reaction, the mixture is fed into a reactor containing a cationic resin catalyst, and when the mixture is fed into the reactor, the alkylation one-step reaction is carried out, part of the reacted material is fed back into the mixer and mixed with the material in the mixer, the temperature of the material in the mixer is raised by the reaction heat, the other part of the reacted material is fed into a thin film evaporator to carry out light and heavy component separation, the temperature is controlled to be between 170 ℃ and 180 ℃, the light component is still circulated into the mixer, the heavy component is fed into a dephenolizing rectification column to carry out dephenolization, the dephenolizing temperature is controlled to be between 180 ℃ and +/-5 ℃, the dephenolizing crude nonylphenol is fed into a finished product rectification column to separate high-purity nonylphenol, and the finished product rectification temperature is controlled to be about 200 ℃.
Preferably, in the first step, the mixed raw materials are pumped by a pump to be circulated, so that the phenol and the nonene are fully and uniformly mixed.
Preferably, in the second step, before the mixture is preheated, the mixture is preheated primarily, the preheating is carried out by raising the temperature to be in the range of 50-55 ℃, and after the primary preheating is continued, the preheating temperature is raised to be within the range of 98 plus or minus 2 ℃, and the preheating temperature is controlled to be in the range of 98 plus or minus 2 ℃.
Preferably, in the third step, after the preheating temperature of the mixture is stable in the alkylation reaction, the mixture is input into a reactor filled with a cationic resin catalyst, when the mixture enters the reactor, the alkylation one-step reaction is carried out, part of the reacted materials returns to the mixer to be mixed with the materials in the mixer, the temperature of the materials in the mixer is increased by using reaction heat, the other part of the materials enters a film evaporator to be subjected to light and heavy component separation, the temperature is controlled to be 170-180 ℃, the light components are still circulated into the mixer, the heavy components enter a dephenolization rectifying tower to be dephenolized, the dephenolization temperature is controlled to be 180 +/-5 ℃, the dephenolized crude nonylphenol enters a finished product rectifying tower to be separated into high-purity nonylphenol, the finished product rectifying temperature is controlled to be about 200 ℃, and the nonylphenol is obtained and input into a storage tank.
The invention has the beneficial effects that:
in the preparation method, because the reaction is exothermic, the reacted materials are continuously input into the mixer in proportion and mixed with the phenol nonene to absorb the reaction heat of the materials, the reaction heat can be better utilized to improve the temperature of the materials in the mixing tank, the energy consumption is more effectively reduced, the whole production process is continuously carried out, only one-step reaction is needed, the energy consumption is low, the by-products are less, the quality is good, and the production efficiency is high.
Drawings
FIG. 1 is a schematic flow structure diagram of a method for producing nonyl phenol.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments.
Example 1, referring to fig. 1, a method for producing nonylphenol comprising the steps of:
step one, mixing uniformly: inputting phenol and nonene into a mixer according to the proportion of 3.2-4:1.4, and circulating the mixed raw materials by using a pump machine to fully and uniformly mix the phenol and the nonene;
step two, preheating treatment: after phenol and nonene are uniformly mixed in proportion, the mixture is subjected to preheating treatment, the temperature of the mixture is raised to the range of 98 +/-2 ℃ by using related heating equipment, phenol and nonene are continuously input into a mixer during the preheating treatment, the mixture is conveyed by a pump and subjected to circulating reflux mixing, and the next treatment is carried out when the preheating temperature is stabilized at 98 +/-2 ℃.
Step three: and (3) alkylation reaction treatment: after the preheating temperature of the mixture is stable, inputting the mixture into a reactor filled with a cationic resin catalyst, performing alkylation one-step reaction when the mixture enters the reactor, returning part of the reacted materials to the mixer, separating light and heavy components of the reacted materials by a thin film evaporator, circulating the light components to the mixer, removing phenol from the heavy components by a dephenolizing rectifying tower, and separating high-purity nonylphenol from the dephenolized crude nonylphenol by a finished product rectifying tower.
Example 2, referring to fig. 1, a method for producing nonylphenol comprising the steps of:
step one, mixing uniformly: inputting phenol and nonene into a mixer according to the proportion of 3.2-4:1.4, and circulating the mixed raw materials by using a pump machine to fully and uniformly mix the phenol and the nonene;
step two, preheating treatment: after phenol and nonene are uniformly mixed in proportion, the mixture is subjected to preheating treatment, the temperature of the mixture is raised to the range of 98 +/-2 ℃ by using related heating equipment, phenol and nonene are continuously input into a mixer during the preheating treatment, the mixture is conveyed by a pump and subjected to circulating reflux mixing, and the next treatment is carried out when the preheating temperature is stabilized at 98 +/-2 ℃.
Step three: and (3) alkylation reaction treatment: after the preheating temperature of the mixture is stable, inputting the mixture into a reactor filled with a cationic resin catalyst, performing alkylation one-step reaction when the mixture enters the reactor, returning part of the reacted materials to the mixer, separating light and heavy components of the reacted materials by a thin film evaporator, circulating the light components to the mixer, removing phenol from the heavy components by a dephenolizing rectifying tower, and separating high-purity nonylphenol from the dephenolized crude nonylphenol by a finished product rectifying tower.
Example 3, referring to fig. 1, a method for producing nonylphenol comprising the steps of:
step one, mixing uniformly: inputting phenol and nonene into a mixer according to the proportion of 3.2-4:1.4, and circulating the mixed raw materials by using a pump machine to fully and uniformly mix the phenol and the nonene;
step two, preheating treatment: after phenol and nonene are uniformly mixed in proportion, the mixture is subjected to preheating treatment, the temperature of the mixture is raised to the range of 98 +/-2 ℃ by using related heating equipment, phenol and nonene are continuously input into a mixer during the preheating treatment, the mixture is conveyed by a pump and subjected to circulating reflux mixing, and the next treatment is carried out when the preheating temperature is stabilized at 98 +/-2 ℃.
Step three: and (3) alkylation reaction treatment: after the preheating temperature of the mixture is stable, inputting the mixture into a reactor filled with a cationic resin catalyst, performing alkylation one-step reaction when the mixture enters the reactor, returning part of the reacted materials to the mixer, separating light and heavy components of the reacted materials by a thin film evaporator, circulating the light components to the mixer, removing phenol from the heavy components by a dephenolizing rectifying tower, and separating high-purity nonylphenol from the dephenolized crude nonylphenol by a finished product rectifying tower.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.
Claims (4)
1. A method for producing nonyl phenol is characterized by comprising the following steps:
step one, mixing uniformly: inputting phenol and nonene into a mixer according to the proportion of 3.2-4:1.4, and circulating the mixed raw materials by using a pump machine to fully and uniformly mix the phenol and the nonene;
step two, preheating treatment: after phenol and nonene are uniformly mixed in proportion, the mixture is subjected to preheating treatment, the temperature of the mixture is raised to the range of 98 +/-2 ℃ by using related heating equipment, phenol and nonene are continuously input into a mixer during the preheating treatment, the mixture is conveyed by a pump and subjected to circulating reflux mixing, and the next treatment is carried out when the preheating temperature is stabilized at 98 +/-2 ℃.
Step three: and (3) alkylation reaction treatment: after the preheating temperature of the mixture is stable, inputting the mixture into a reactor filled with a cationic resin catalyst, performing alkylation one-step reaction when the mixture enters the reactor, returning part of the reacted materials to the mixer, separating light and heavy components of the reacted materials by a thin film evaporator, circulating the light components to the mixer, removing phenol from the heavy components by a dephenolizing rectifying tower, and separating high-purity nonylphenol from the dephenolized crude nonylphenol by a finished product rectifying tower.
2. The method for producing nonyl phenol of claim 1, wherein in step one, the mixed raw materials are circulated by a pump, so that phenol and nonene are mixed uniformly.
3. The method of claim 1, wherein the mixture is preheated by raising the temperature to 50-55 ℃, continuing the preliminary preheating, raising the preheating temperature to 98 ± 2 ℃, and controlling the preheating temperature to 98 ± 2 ℃ in the second step.
4. The method for producing nonylphenol as claimed in claim 1, wherein in step three, after the preheating temperature of the mixture is stabilized during the alkylation reaction, the mixture is fed into a reactor containing a cationic resin catalyst, and when the mixture is fed into the reactor, the alkylation one-step reaction is carried out, part of the reacted material is fed back into the mixer and mixed with the material in the mixer, the temperature of the material in the mixer is raised by the reaction heat, the other part of the reacted material is fed into a thin film evaporator to carry out light and heavy component separation, the temperature is controlled to be between 170 ℃ and 180 ℃, the light component is still circulated into the mixer, the heavy component is fed into a dephenolizing rectification column to carry out dephenolization, the dephenolizing temperature is controlled to be between 180 ℃ and +/-5 ℃, the dephenolizing crude nonylphenol is fed into a finished product rectification column to separate high-purity nonylphenol, and the finished product rectification temperature is controlled to be about 200 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210326247.7A CN114478199A (en) | 2022-03-30 | 2022-03-30 | Method for producing nonyl phenol |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210326247.7A CN114478199A (en) | 2022-03-30 | 2022-03-30 | Method for producing nonyl phenol |
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| CN114478199A true CN114478199A (en) | 2022-05-13 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210326247.7A Pending CN114478199A (en) | 2022-03-30 | 2022-03-30 | Method for producing nonyl phenol |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4168390A (en) * | 1973-09-14 | 1979-09-18 | Chemische Werke Huls A.G. | Process for continuous alkylation of phenol using ion exchange resins |
| CN1185426A (en) * | 1996-01-25 | 1998-06-24 | 中国石油化工总公司 | Process for preparing alkylphenol |
| CN104387239A (en) * | 2014-11-25 | 2015-03-04 | 江苏凌飞科技股份有限公司 | Method for increasing content of para-nonylphenol in nonylphenol product |
-
2022
- 2022-03-30 CN CN202210326247.7A patent/CN114478199A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4168390A (en) * | 1973-09-14 | 1979-09-18 | Chemische Werke Huls A.G. | Process for continuous alkylation of phenol using ion exchange resins |
| CN1185426A (en) * | 1996-01-25 | 1998-06-24 | 中国石油化工总公司 | Process for preparing alkylphenol |
| CN104387239A (en) * | 2014-11-25 | 2015-03-04 | 江苏凌飞科技股份有限公司 | Method for increasing content of para-nonylphenol in nonylphenol product |
Non-Patent Citations (2)
| Title |
|---|
| 张文昕等: "壬基酚生产工艺条件研究", 《精细化工》, vol. 17, no. 9, pages 503 - 504 * |
| 黄振军: "壬基酚装置扩能改造研究", 《中国优秀博硕士学位论文全文数据库（硕士）工程科技Ⅰ辑》, no. 12, pages 016 - 14 * |
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