CN114560751A - Method for producing cis-or trans-1, 3-dichloropropene - Google Patents
Method for producing cis-or trans-1, 3-dichloropropene Download PDFInfo
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- CN114560751A CN114560751A CN202210136390.XA CN202210136390A CN114560751A CN 114560751 A CN114560751 A CN 114560751A CN 202210136390 A CN202210136390 A CN 202210136390A CN 114560751 A CN114560751 A CN 114560751A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/358—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by isomerisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
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- C—CHEMISTRY; METALLURGY
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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Abstract
The invention provides a method for producing cis-or trans-1, 3-dichloropropene, which can carry out mutual conversion of cis-1, 3-dichloropropene and trans-1, 3-dichloropropene without visible light or ultraviolet light by using a catalyst, can freely select the conversion direction according to the actual requirements, has simple equipment without special design, can be used for preparing trans-1, 3-dichloropropene from cis-1, 3-dichloropropene and can also be operated in the reverse direction by using the same equipment, only needs to use a pipeline to control corresponding products to enter a product tank and a raw material tank, has low cost and easy obtainment, can mix a plurality of catalysts without influencing the catalytic effect, can be obtained by recycling waste materials, does not need illumination in a reactor, can be freely designed, can meet the requirement of large-scale production, and the gas phase of the reactor enters the rectifying tower through flash evaporation, can be continuously produced, and is simple and convenient to operate.
Description
Technical Field
The invention relates to the field of chemical intermediate production, in particular to a production method of trans-form or cis-form-1, 3-dichloropropene.
Background
1, 3-dichloropropene is a byproduct in the production of epoxy chloropropane and contains cis-1, 3-dichloropropene and trans-1, 3-dichloropropene isomer in a mixture form, and CN110078584A discloses a process for recovering dichloropropane and dichloropropene from a DD mixed agent.
The cis-1, 3-dichloropropene and the trans-1, 3-dichloropropene have different uses and the price varies with the demand, CN109694308A discloses a method for converting the trans-1, 3-dichloropropene into the cis-1, 3-dichloropropene, and CN111848334A discloses a method for converting the cis-1, 3-dichloropropene into the trans-1, 3-dichloropropene, but the methods all need to be reacted under the conditions of visible light or ultraviolet light. The photocatalysis has the defects that ultraviolet light or visible light is generally required to irradiate the reactor, the reactor needs to be transparent or a light source is arranged inside the reactor, the design of the reactor is greatly limited, and the photocatalysis is difficult to apply to industrial production.
Disclosure of Invention
In order to solve the problems in the background art, the invention provides the following technical scheme:
a process for producing trans-1, 3-dichloropropene comprising the steps of:
s1: mixing cis-1, 3-dichloropropene and a catalyst in a proportioning kettle in proportion;
s2: continuously introducing the mixed raw materials into a kettle type reactor for reaction;
s3: extracting reaction liquid from the top of the kettle reactor through gas phase to a rectifying tower for negative pressure rectification, and supplying heat through a reboiler;
s4: the trans-1, 3-dichloropropene extracted from the side line is condensed by a condenser and enters a product tank, and the cis-1, 3-dichloropropene extracted from the top is condensed and enters a raw material tank.
In S1, the catalyst is C3-C6 brominated alkanes or alkenes.
Further, in S1, the catalyst is selected from one or more of 3-bromopropene, 1, 2, 2-tribromopropane, 1-bromo-1, 5-hexadiene, 1-bromohexene, and 1-bromo-4-methylpentene.
Further, in S1, the weight ratio of the catalyst to cis-1, 3-dichloropropene is from 0.3% to 1.5%.
Further, in S2, the reaction conditions in the tank reactor are: the reaction temperature is 60-80 ℃, and the reaction residence time is 2-4 h; in S3, the bottom temperature of the rectifying tower is 82 ℃, the top temperature of the rectifying tower is 62 ℃, the bottom vacuum degree of the rectifying tower is-0.065 MPa, the top vacuum degree of the rectifying tower is-0.075 MPa, and the reflux ratio of the rectifying tower is 3-6: 1; the feed rate in S2 corresponds to the withdrawal rate in S3.
The invention also provides a production method of cis-1, 3-dichloropropene, which comprises the following steps:
s1: mixing trans-1, 3-dichloropropene and a catalyst in a proportioning kettle in proportion;
s2: continuously introducing the mixed raw materials into a kettle type reactor for reaction;
s3: extracting reaction liquid from the top of the kettle reactor through gas phase to a rectifying tower for negative pressure rectification, and supplying heat through a reboiler;
s4: the trans-1, 3-dichloropropene extracted from the side line is condensed by a condenser and enters a raw material tank, and the cis-1, 3-dichloropropene extracted from the top is condensed and enters a product tank.
In S1, the catalyst is C3-C6 brominated alkanes or alkenes.
Further, in S1, the catalyst is selected from one or more of 3-bromopropene, 1, 2, 2-tribromopropane, 1-bromo-1, 5-hexadiene, 1-bromohexene, and 1-bromo-4-methylpentene.
Further, in S1, the weight ratio of the catalyst to trans-1, 3-dichloropropene is from 0.3% to 1.5%.
Further, in S2, the reaction conditions in the tank reactor are: the reaction temperature is 60-80 ℃, and the reaction residence time is 2-4 h; in S3, the bottom temperature of the rectifying tower is 82 ℃, the top temperature of the rectifying tower is 62 ℃, the bottom vacuum degree of the rectifying tower is-0.065 MPa, the top vacuum degree of the rectifying tower is-0.075 MPa, and the reflux ratio of the rectifying tower is 3-6: 1; the feed rate in S2 corresponds to the withdrawal rate in S3.
The invention has the beneficial effects that:
the invention provides a method for producing cis-or trans-1, 3-dichloropropene, which can carry out mutual conversion of cis-1, 3-dichloropropene and trans-1, 3-dichloropropene without visible light or ultraviolet light by using a catalyst, can freely select the conversion direction according to the actual requirements, has simple equipment without special design, even the same set of equipment can be used for preparing the trans-1, 3-dichloropropene from the cis-1, 3-dichloropropene and also can be used for preparing the cis-1, 3-dichloropropene from the trans-1, 3-dichloropropene, only a pipeline is needed to control corresponding products to enter a product tank and a raw material tank, the catalyst of the technical scheme of the invention has low cost and is easy to obtain, the reactor in the technical scheme of the invention can be freely designed because the reactor does not need illumination, can meet the requirement of mass production, can continuously produce when the gas phase of the reactor enters the rectifying tower through flash evaporation, and is simple and convenient to operate.
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.
Example 1
A process for producing trans-1, 3-dichloropropene comprising the steps of:
s1: raw material cis-1, 3-dichloropropene (with the content of 98%) and catalyst 3-bromopropene are mixed in a blending kettle according to the weight ratio of 1: mixing at a ratio of 0.3%;
s2: the mixed raw materials are continuously fed into a 500L kettle-type reactor at a feeding speed of 75L/h for reaction, the reaction temperature is 60 ℃, and the reaction residence time is 4h (calculated by a feeding coefficient of 0.6);
s3: extracting reaction liquid into a rectifying tower through a gas phase at the top of a kettle type reactor, wherein the operating conditions of the rectifying tower are that the temperature of the tower bottom is 82 ℃, the temperature of the tower top is 62 ℃, the vacuum degree of the tower bottom is-0.065 MPa, the vacuum degree of the tower top is-0.075 MPa, heat is supplied through a reboiler, and the reflux ratio of the rectifying tower is 6: 1;
s4: the trans-1, 3-dichloropropene with the content of 99.1 percent is extracted from the side line and condensed by a condenser, the extracted amount is 21.4L/h and enters a product tank, the cis-1, 3-dichloropropene with the content of 98.4 percent is condensed and then the extracted amount is 53.6L/h and enters a raw material tank.
Example 2
A process for producing trans-1, 3-dichloropropene comprising the steps of:
s1: raw material cis-1, 3-dichloropropene (with the content of 98%) and catalyst 1-bromo-1, 5-hexadiene are added into a blending kettle according to the weight ratio of 1: mixing at a ratio of 0.6%;
s2: the mixed raw materials are continuously fed into a 500L kettle-type reactor at a feeding speed of 100L/h for reaction, the reaction temperature is 65 ℃, and the reaction residence time is 3h (calculated by a feeding coefficient of 0.6);
s3: extracting reaction liquid into a rectifying tower through a gas phase at the top of a kettle type reactor, wherein the operating conditions of the rectifying tower are that the temperature of the tower bottom is 82 ℃, the temperature of the tower top is 62 ℃, the vacuum degree of the tower bottom is-0.065 MPa, the vacuum degree of the tower top is-0.075 MPa, heat is supplied through a reboiler, and the reflux ratio of the rectifying tower is 4: 1;
s4: the trans-1, 3-dichloropropene with the content of 99.2 percent is extracted from the side line and condensed by a condenser, the extracted amount is 39.8L/h, the cis-1, 3-dichloropropene with the content of 98.1 percent is extracted from the top, and the extracted amount is 60.2L/h after condensation and enters a raw material tank.
Example 3
A process for producing trans-1, 3-dichloropropene comprising the steps of:
s1: mixing a raw material cis-1, 3-dichloropropene (with the content of 98%) and a catalyst 1-bromo-1, 5-hexadiene and 1-bromohexene in a blending kettle according to the weight ratio of 1: mixing at a ratio of 1.5%;
s2: the mixed raw materials are continuously fed into a 500L kettle-type reactor at a feeding speed of 150L/h for reaction, the reaction temperature is 80 ℃, and the reaction residence time is 2h (calculated by a feeding coefficient of 0.6);
s3: extracting reaction liquid into a rectifying tower through a gas phase at the top of a kettle type reactor, wherein the operating conditions of the rectifying tower are that the temperature of the tower bottom is 82 ℃, the temperature of the tower top is 62 ℃, the vacuum degree of the tower bottom is-0.065 MPa, the vacuum degree of the tower top is-0.075 MPa, heat is supplied through a reboiler, and the reflux ratio of the rectifying tower is 3: 1;
s4: the trans-1, 3-dichloropropene with the content of 99.0 percent is extracted from the side line and condensed by a condenser, the extracted amount is 68.1L/h and enters a product tank, the cis-1, 3-dichloropropene with the content of 97.8 percent is condensed and then the extracted amount is 81.8L/h and enters a raw material tank.
Example 4
A process for producing cis-1, 3-dichloropropene comprising the steps of:
s1: raw material trans-1, 3-dichloropropene (content 96.7%) and catalyst 1, 2, 2-tribromopropane are added into a blending kettle according to the weight ratio of 1: mixing at a ratio of 0.9%;
s2: the mixed raw materials are continuously introduced into a 500L kettle-type reactor at a feeding speed of 120L/h for reaction, the reaction temperature is 70 ℃, and the reaction residence time is 2.5h (calculated by a feeding coefficient of 0.6);
s3: extracting reaction liquid into a rectifying tower through a gas phase at the top of a kettle type reactor, wherein the operating conditions of the rectifying tower are that the temperature of the tower bottom is 82 ℃, the temperature of the tower top is 62 ℃, the vacuum degree of the tower bottom is-0.065 MPa, the vacuum degree of the tower top is-0.075 MPa, heat is supplied through a reboiler, and the reflux ratio of the rectifying tower is 4: 1;
s4: the trans-1, 3-dichloropropene is extracted from the side line, the content of the trans-1, 3-dichloropropene is 97.3 percent, the trans-1, 3-dichloropropene is condensed by a condenser, the extracted amount is 48.1L/h and enters a raw material tank, the cis-1, 3-dichloropropene is extracted from the top, the content of the cis-1, 3-dichloropropene is 98.6 percent, and the extracted amount is 71.9L/h and enters a product tank after the condensation.
Example 5
A process for producing cis-1, 3-dichloropropene comprising the steps of:
s1: raw material trans-1, 3-dichloropropene (content: 96.7%) and catalyst 1-bromo-4-methylpentene are added into a blending kettle according to the weight ratio of 1: mixing at a ratio of 1.2%;
s2: the mixed raw materials are continuously fed into a 500L kettle-type reactor at a feeding speed of 86L/h for reaction, the reaction temperature is 75 ℃, and the reaction residence time is 3.5h (calculated by a feeding coefficient of 0.6);
s3: extracting reaction liquid into a rectifying tower through a gas phase at the top of a kettle reactor, wherein the operating conditions of the rectifying tower are that the temperature of the tower bottom is 82 ℃, the temperature of the tower top is 62 ℃, the vacuum degree of the tower bottom is-0.065 MPa, the vacuum degree of the tower top is-0.075 MPa, and heat is supplied through a reboiler, and the reflux ratio of the rectifying tower is 5: 1;
s4: the trans-1, 3-dichloropropene with the content of 98.0 percent is extracted from the side line and condensed by a condenser, the extracted amount is 28.7L/h and enters a raw material tank, the cis-1, 3-dichloropropene with the content of 99.0 percent is condensed and then the extracted amount is 57.3L/h and enters a product tank.
Finally, it should be noted that the above-mentioned contents are only used for illustrating the technical solutions of the present invention, and not for limiting the protection scope of the present invention, and that the simple modifications or equivalent substitutions of the technical solutions of the present invention by those of ordinary skill in the art can be made without departing from the spirit and scope of the technical solutions of the present invention.
Claims (10)
1. A method for producing trans-1, 3-dichloropropene is characterized by comprising the following steps: the method comprises the following steps:
s1: mixing cis-1, 3-dichloropropene and a catalyst in a batching kettle according to a proportion;
s2: continuously introducing the mixed raw materials into a kettle type reactor for reaction;
s3: extracting reaction liquid from the top of the kettle reactor through gas phase to a rectifying tower for negative pressure rectification, and supplying heat through a reboiler;
s4: the trans-1, 3-dichloropropene extracted from the side line is condensed by a condenser and enters a product tank, and the cis-1, 3-dichloropropene extracted from the top is condensed and enters a raw material tank.
2. The process according to claim 1 for producing trans-1, 3-dichloropropene, which comprises: in S1, the catalyst is alkyl bromide of C3-C6 and olefin.
3. The process according to claim 2, wherein the polymerization reaction is carried out in the presence of a catalyst selected from the group consisting of: in S1, the catalyst is selected from one or more of 3-bromopropene, 1, 2, 2-tribromopropane, 1-bromo-1, 5-hexadiene, 1-bromohexene and 1-bromo-4-methylpentene.
4. A process for producing trans-1, 3-dichloropropene according to any one of claims 1 to 3, which comprises: in S1, the weight ratio of the catalyst to cis-1, 3-dichloropropene is 0.3% to 1.5%.
5. The process according to claim 5, wherein the polymerization reaction is carried out in the presence of a catalyst selected from the group consisting of: in S2, the reaction conditions in the tank reactor are: the reaction temperature is 60-80 ℃, and the reaction residence time is 2-4 h; in S3, the bottom temperature of the rectifying tower is 82 ℃, the top temperature of the rectifying tower is 62 ℃, the bottom vacuum degree of the rectifying tower is-0.065 MPa, the top vacuum degree of the rectifying tower is-0.075 MPa, and the reflux ratio of the rectifying tower is 3-6: 1; the feed rate in S2 corresponds to the withdrawal rate in S3.
6. A method for producing cis-1, 3-dichloropropene is characterized in that: the method comprises the following steps:
s1: mixing trans-1, 3-dichloropropene and a catalyst in a proportioning kettle in proportion;
s2: continuously introducing the mixed raw materials into a kettle type reactor for reaction;
s3: extracting reaction liquid from the top of the kettle reactor through gas phase to a rectifying tower for negative pressure rectification, and supplying heat through a reboiler;
s4: the trans-1, 3-dichloropropene extracted from the side line is condensed by a condenser and enters a raw material tank, and the cis-1, 3-dichloropropene extracted from the top is condensed and enters a product tank.
7. The process according to claim 1 for producing cis-1, 3-dichloropropene, which comprises: in S1, the catalyst is alkyl bromide of C3-C6 and olefin.
8. The process according to claim 2, wherein: in S1, the catalyst is selected from one or more of 3-bromopropene, 1, 2, 2-tribromopropane, 1-bromo-1, 5-hexadiene, 1-bromohexene and 1-bromo-4-methylpentene.
9. The process according to any one of claims 1 to 3 for producing cis-1, 3-dichloropropene, which comprises: in S1, the weight ratio of the catalyst to trans-1, 3-dichloropropene is 0.3-1.5%.
10. The process according to claim 5, wherein: in S2, the reaction conditions in the tank reactor are: the reaction temperature is 60-80 ℃, and the reaction residence time is 2-4 h; in S3, the bottom temperature of the rectifying tower is 82 ℃, the top temperature of the rectifying tower is 62 ℃, the bottom vacuum degree of the rectifying tower is-0.065 MPa, the top vacuum degree of the rectifying tower is-0.075 MPa, and the reflux ratio of the rectifying tower is 3-6: 1; the feed rate in S2 corresponds to the withdrawal rate in S3.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116440951A (en) * | 2023-06-19 | 2023-07-18 | 山东河清化工科技有限公司 | Cis-trans isomerism catalyst and preparation method and application thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116440951A (en) * | 2023-06-19 | 2023-07-18 | 山东河清化工科技有限公司 | Cis-trans isomerism catalyst and preparation method and application thereof |
| CN116440951B (en) * | 2023-06-19 | 2023-08-11 | 山东河清化工科技有限公司 | Cis-trans isomerism catalyst and preparation method and application thereof |
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