CN113563155B - Bromopropene synthesis method - Google Patents
Bromopropene synthesis method Download PDFInfo
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- CN113563155B CN113563155B CN202110851429.1A CN202110851429A CN113563155B CN 113563155 B CN113563155 B CN 113563155B CN 202110851429 A CN202110851429 A CN 202110851429A CN 113563155 B CN113563155 B CN 113563155B
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- bromopropene
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- gas
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- NNQDMQVWOWCVEM-UHFFFAOYSA-N 1-bromoprop-1-ene Chemical compound CC=CBr NNQDMQVWOWCVEM-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 238000001308 synthesis method Methods 0.000 title claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 97
- 239000007788 liquid Substances 0.000 claims abstract description 40
- 239000003513 alkali Substances 0.000 claims abstract description 33
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims abstract description 32
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000012495 reaction gas Substances 0.000 claims abstract description 26
- 239000002994 raw material Substances 0.000 claims abstract description 22
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 17
- 238000005406 washing Methods 0.000 claims abstract description 17
- 239000007789 gas Substances 0.000 claims abstract description 14
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims abstract description 14
- 238000003756 stirring Methods 0.000 claims abstract description 10
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000007599 discharging Methods 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 27
- 239000000047 product Substances 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 10
- 238000003860 storage Methods 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 7
- 239000011265 semifinished product Substances 0.000 claims description 6
- 239000002808 molecular sieve Substances 0.000 claims description 5
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 238000004321 preservation Methods 0.000 claims description 3
- 230000002194 synthesizing effect Effects 0.000 claims 8
- 230000032798 delamination Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 10
- 230000035484 reaction time Effects 0.000 abstract description 5
- 239000002351 wastewater Substances 0.000 abstract description 5
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 6
- 230000031709 bromination Effects 0.000 description 4
- 238000005893 bromination reaction Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000004062 sedimentation Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
-
- 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
-
- 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
- C07C17/395—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to a chemical modification of at least one compound
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)
Abstract
The application discloses a bromopropene synthesis method, which comprises the following steps: 1) Adding the liquid raw material into a reaction kettle; the liquid raw material comprises an allyl alcohol liquid; 2) Introducing reaction gas into a reaction kettle, and continuously stirring liquid raw materials in the reaction kettle until the reaction is finished to obtain an intermediate reaction liquid I; the reaction gas contains hydrogen bromide gas; 3) After the reaction of the step 2) is completed, standing and layering the intermediate reaction liquid I formed in the step 2); after standing and layering, discharging hydrobromic acid at the bottom to obtain an intermediate reaction solution II; 4) Adding alkali liquor into the reaction kettle, and performing alkali washing on the intermediate reaction liquid II obtained after the completion of the step 3) to obtain an intermediate reaction liquid III. The bromopropene synthesis method can effectively reduce the reaction time, reduce the production amount of wastewater, and the purity of the produced bromopropene product is high.
Description
Technical Field
The invention relates to a bromopropene synthesis method, and belongs to the field of chemical production.
Background
Bromopropene, an organic compound, has an unpleasant, irritating odor, is mainly used for organic synthesis, is used as an intermediate for resins and fragrances, and is also harmful to the environment. In the conventional process, the method for producing bromopropene includes an allyl alcohol bromination method and a propylene bromination method. In the allyl alcohol bromination method, hydrobromic acid is charged into a reaction tank, and sulfuric acid and allyl alcohol are added with stirring. Heating and refluxing for 2h, heating to 8deg.C, distilling off the distillate, and collecting 68-73deg.C fraction. After washing with water, the mixture is dehydrated by anhydrous sodium sulfate and filtered to obtain allyl bromide. In the propylene bromination method, hydrobromic acid is mixed with allyl alcohol to react. The reaction time in the production process of the two methods is long, and the purity of the produced product is low; the product obtained by the reaction needs to be distilled and purified, the purity of the distilled product is low, and the product of bromopropene with high purity is difficult to produce. And a certain amount of wastewater can be generated by mixing hydrobromic acid and allyl alcohol for production, and more wastewater is produced.
Disclosure of Invention
The invention provides a bromopropene synthesis method, which synthesizes a bromopropene product by adopting a simple method, can effectively reduce the reaction time, reduce the production amount of wastewater, and has high purity of the produced bromopropene product.
The technical scheme adopted by the invention is that the bromopropene synthesis method comprises the following steps:
1) Adding the liquid raw material into a reaction kettle; the liquid raw material comprises an allyl alcohol liquid;
2) Introducing reaction gas into a reaction kettle, and continuously stirring liquid raw materials in the reaction kettle until the reaction is finished to obtain an intermediate reaction liquid I; the reaction gas contains hydrogen bromide gas;
3) After the reaction of the step 2) is completed, standing and layering the intermediate reaction liquid I formed in the step 2); after standing and layering, discharging hydrobromic acid at the bottom to obtain an intermediate reaction solution II;
4) Adding alkali liquor into the reaction kettle, and performing alkali washing on the intermediate reaction liquid II obtained after the completion of the step 3), so as to obtain an intermediate reaction liquid III after alkali washing;
5) Naturally settling the intermediate reaction solution III obtained after the alkaline washing in the step 4), transferring the lower material obtained after settling into a semi-finished product storage tank, and discharging the upper alkali liquor obtained after settling into an alkali liquor storage tank;
6) Adding the lower material transferred into the semi-finished product storage tank in the step 5) into a molecular sieve dryer for drying to obtain a bromopropene finished product; transferring the finished product of the bromopropene into a finished product tank of the bromopropene for preservation.
Preferably, in the above bromopropene synthesis process, in step 2), the reaction is completed when WAB is 99% or more in the liquid in the reaction vessel.
Optimally, in the bromopropene synthesis method, in the step 2), the reaction gas introduced into the reaction kettle comprises hydrogen bromide gas and excessive hydrogen, and the concentration of the hydrogen bromide gas in the reaction gas is more than or equal to 90%; in the step 2), the speed of the reaction gas flowing into the reaction kettle is 15-17m 3 /h。
Optimally, according to the bromopropene synthesis method, the concentration of the allyl alcohol liquid in the liquid raw material added into the reaction kettle in the step 1) is more than or equal to 99.5%; the liquid raw materials are metered into the reaction kettle at one time.
Optimally, in the above bromopropene synthesis method, in step 2), the reaction gas is continuously introduced into the reaction kettle; in the reaction process of the step 2), the pressure in the reaction kettle is kept at 0.01-0.03MPa, the reaction temperature is 25-35 ℃, and the stirring speed is 120-140r/min.
Optimally, in the bromopropene synthesis method, in the step 1) and the step 2), the weight ratio of the total introduced amount of the reaction gas to the added amount of the liquid raw material is 9:5.
optimally, in the bromopropene synthesis method, when standing and layering are carried out in the step 3), standing is carried out for 30min, and standing can be stopped after the solution layering is completed.
Optimally, in the above bromopropene synthesis method, in the step 4), the concentration of the alkali liquor added into the reaction kettle is 30% -35%, and the weight of the alkali liquor in the reaction kettle is as follows: 1Kg of alkali liquor is added into the reaction kettle every 150L of volume; the alkali washing time is 30min, and the PH value of the solution in the reaction kettle is 12 when the alkali washing is stopped; the weight ratio of the alkali liquor to the second reaction solution is 1:125.
Optimally, in the above bromopropene synthesis method, in the step 6), the lower material is dried by a molecular sieve dryer at normal temperature, and the moisture of the finished bromopropene product after drying is less than or equal to 1000ppm.
The application has the advantages that:
in the technical scheme of the application, the bromopropene is synthesized by using the hydrogen bromide gas and the allyl alcohol liquid through reaction, and compared with hydrobromic acid used in the prior art, the method has high product yield (about 95 percent of yield) in the reaction process, can effectively reduce the reaction time and improve the production efficiency. And the reaction time is reduced, so that the energy consumption can be reduced, and the reaction cost is further reduced. The synthetic method does not need rectification in the production process, so that the steam consumption of rectification is reduced, and the energy consumption is reduced. No waste water is generated in the synthesis process, pollution is reduced, and the cost of waste water treatment in the later stage can be reduced. The purity of the bromopropene produced by the method is higher than that of a finished product produced by the existing method, the product quality is high, and the economic benefit is good.
Drawings
Fig. 1 is a flow chart of a bromopropene synthesis process of the present application.
Detailed Description
The technical features of the present invention are further described below with reference to the accompanying drawings and the specific embodiments.
Example 1:
as shown in the figure, the invention discloses a bromopropene synthesis method, which comprises the following steps:
step 1) liquid raw materials are metered into a reaction kettle at one time; the liquid raw material comprises the allyl alcohol liquid, and the concentration of the allyl alcohol liquid in the liquid raw material is 99.5%;
step 2) continuously introducing reaction gas into a reaction kettle, wherein the speed of introducing the reaction gas into the reaction kettle is 16m 3 And/h, the reaction gas comprises hydrogen bromide gas and excessive hydrogen, and the concentration of the hydrogen bromide gas in the reaction gas is 90%;
continuously stirring liquid raw materials in a reaction kettle until the reaction is finished to obtain an intermediate reaction liquid I; in the reaction process, the pressure in the reaction kettle is kept at 0.02MPa, the temperature in the reaction kettle is 30 ℃, and the stirring speed is 130r/min; the reaction gas contains hydrogen bromide gas; the reaction was completed when the WAB in the liquid in the reaction vessel was 99%.
In the steps 1) and 2), the weight ratio of the total amount of the introduced reaction gas to the addition amount of the liquid raw material was 9:5.
step 3) after the reaction of the step 2), standing and layering the intermediate reaction liquid I formed in the step 2); after standing and layering, discharging hydrobromic acid at the bottom to obtain an intermediate reaction solution II; the standing time is 30min, and the standing can be stopped after the solution is completely layered.
Step 4) adding alkali liquor into the reaction kettle, and performing alkali washing on the intermediate reaction liquid II obtained after the completion of the step 3) to obtain an intermediate reaction liquid III;
the concentration of the alkali liquor added into the reaction kettle is 32%; the weight of alkali liquor in the reaction kettle is as follows: 1Kg of alkali liquor is added into the reaction kettle every 150L of volume; the alkali washing time is 30min, and the PH value of the solution in the reaction kettle is 12 when the alkali washing is stopped; the weight ratio of the alkali liquor to the second reaction solution is 1:125.
Step 5) carrying out natural sedimentation on the intermediate reaction liquid III obtained after the alkaline washing in the step 4), transferring the lower material obtained after sedimentation into a semi-finished product storage tank, and discharging the upper alkaline liquid obtained after sedimentation into an alkaline liquid storage tank;
step 6), adding the lower material transferred into the semi-finished product storage tank in the step 5) into a molecular sieve dryer for drying, and stopping drying after the water content in the bromopropene is 999.9ppm to obtain a bromopropene finished product; transferring the finished product of the bromopropene into a finished product tank of the bromopropene for preservation.
Step 1) and step 2) are reaction processes, mainly refer to that hydrogen bromide gas after impurity removal reacts with allyl alcohol at a certain reaction temperature, and equipment for completing the process mainly comprises: glass lining reaction kettle and material transferring pump.
Step 3), step 4) and step 5) are alkaline washing processes, mainly refer to that after allyl bromide produced by the reaction is separated from acid, the allyl bromide is washed, and the acid and liquid alkali contained in the allyl bromide are subjected to neutralization reaction, so that the allyl bromide is in a stable process. The equipment for completing the process mainly comprises: glass lining reaction kettle, material transfer pump, intermediate product storage tank (glass lining).
Step 6) is a drying process, mainly referring to a process that allyl bromide products containing certain moisture meet the moisture requirement of the products after being dried. The equipment for completing the process mainly comprises: drying tower, transfer pump, etc.
The reaction data in the embodiment is the best reaction data of the application, and the production of the finished product of the bromopropene is carried out under the condition, so that lower production loss and lower production energy consumption can be ensured under the condition of ensuring the quality of the finished product of the bromopropene, and the comprehensive economic benefit is higher than that of other embodiments.
Example 2
This embodiment differs from embodiment 1 in that:
the reaction was completed when the WAB concentration in the liquid in the reaction vessel was 99.4%.
The concentration of hydrogen bromide gas in the reaction gas was 92%; in the step 2), the reaction gas is introduced into the reaction kettleIs 15m 3 /h。
The concentration of the allyl alcohol liquid in the liquid raw material added into the reaction kettle in the step 1) is more than or equal to 99.5 percent; in the reaction process of the step 2), the pressure in the reaction kettle is kept at 0.01MPa, the reaction temperature is 25 ℃, and the stirring speed is 120r/min. The moisture of the finished product of the dry bromopropene was 999.8ppm.
Example 3
This embodiment differs from embodiments 1, 2 in that: the reaction was completed when the WAB in the liquid in the reaction vessel was 99.7%.
The concentration of hydrogen bromide gas in the reaction gas was 94%; in the step 2), the velocity of the reaction gas when it was introduced into the reaction vessel was 17m 3 And/h. The concentration of the allyl alcohol liquid in the liquid raw material added into the reaction kettle in the step 1) is more than or equal to 99.5 percent;
in the reaction process of the step 2), the pressure in the reaction kettle is kept at 0.03MPa, the reaction temperature is 35 ℃, and the stirring speed is 140r/min. The moisture of the finished product of the dry bromopropene was 999ppm.
It should be understood that the above description is not intended to limit the invention to the particular embodiments disclosed, but to limit the invention to the particular embodiments disclosed, and that various changes, modifications, additions and substitutions can be made by those skilled in the art without departing from the spirit and scope of the invention.
Claims (9)
1. A bromopropene synthesis method is characterized in that: the method comprises the following steps:
1) Adding the liquid raw material into a reaction kettle; the liquid raw material comprises an allyl alcohol liquid;
2) Introducing reaction gas into a reaction kettle, and continuously stirring liquid raw materials in the reaction kettle until the reaction is finished to obtain an intermediate reaction liquid I; the reaction gas contains hydrogen bromide gas;
3) After the reaction of the step 2) is completed, standing and layering the intermediate reaction liquid I formed in the step 2); after standing and layering, discharging hydrobromic acid at the bottom to obtain an intermediate reaction solution II;
4) Adding alkali liquor into the reaction kettle, and performing alkali washing on the intermediate reaction liquid II obtained after the completion of the step 3), so as to obtain an intermediate reaction liquid III after alkali washing;
5) Naturally settling the intermediate reaction solution III obtained after the alkaline washing in the step 4), transferring the lower material obtained after settling into a semi-finished product storage tank, and discharging the upper alkali liquor obtained after settling into an alkali liquor storage tank;
6) Adding the lower material transferred into the semi-finished product storage tank in the step 5) into a molecular sieve dryer for drying to obtain a bromopropene finished product; transferring the finished bromopropene product into a finished bromopropene tank for preservation;
in the step 2), the reaction gas introduced into the reaction kettle comprises hydrogen bromide gas and excessive hydrogen, and the concentration of the hydrogen bromide gas in the reaction gas is more than or equal to 90%.
2. The method for synthesizing bromopropene according to claim 1, characterized in that: in the step 2), the reaction is finished when WAB in the liquid in the reaction kettle is more than or equal to 99 percent.
3. The method for synthesizing bromopropene according to claim 1, characterized in that: in step 2), the reaction gas is introduced into the reaction kettle at a speed of 15-17m3/h.
4. The method for synthesizing bromopropene according to claim 1, characterized in that: the concentration of the allyl alcohol liquid in the liquid raw material added into the reaction kettle in the step 1) is more than or equal to 99.5 percent; the liquid raw materials are metered into the reaction kettle at one time.
5. The method for synthesizing bromopropene according to claim 1, characterized in that: in the step 2), continuously introducing reaction gas into a reaction kettle; in the reaction process of the step 2), the pressure in the reaction kettle is kept at 0.01-0.03MPa, the reaction temperature is 25-35 ℃, and the stirring speed is 120-140r/min.
6. The method for synthesizing bromopropene according to claim 1, characterized in that: in the steps 1) and 2), the weight ratio of the total amount of the introduced reaction gas to the addition amount of the liquid raw material was 9:5.
7. the method for synthesizing bromopropene according to claim 1, characterized in that: and 3) standing for 30min when the solution is subjected to standing delamination in the step 3), and stopping standing after the solution is completely delaminated.
8. The method for synthesizing bromopropene according to claim 1, characterized in that: in the step 4), the concentration of the alkali liquor added into the reaction kettle is 30% -35%, and the weight of the alkali liquor in the reaction kettle is as follows: 1Kg of alkali liquor is added into the reaction kettle every 150L of volume; the alkali washing time is 30min, and the PH value of the solution in the reaction kettle is 12 when the alkali washing is stopped; the weight ratio of the alkali liquor to the second reaction solution is 1:125.
9. The method for synthesizing bromopropene according to claim 1, characterized in that: in the step 6), the lower material is dried by a molecular sieve dryer at normal temperature, and the moisture of the finished product of the dry bromopropene is less than or equal to 1000ppm.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202110851429.1A CN113563155B (en) | 2021-07-27 | 2021-07-27 | Bromopropene synthesis method |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202110851429.1A CN113563155B (en) | 2021-07-27 | 2021-07-27 | Bromopropene synthesis method |
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| CN113563155B true CN113563155B (en) | 2024-02-13 |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3981938A (en) * | 1974-07-08 | 1976-09-21 | The Dow Chemical Company | Method for producing dry alkyl halides |
| CN102010288A (en) * | 2010-08-20 | 2011-04-13 | 寿光市鲁源盐化有限公司 | Method for producing allyl bromide |
| CN104058926A (en) * | 2014-06-04 | 2014-09-24 | 蚌埠团结日用化学有限公司 | Production technique for synthesizing 1-bromo-3-chloropropane |
| CN107973692A (en) * | 2017-11-24 | 2018-05-01 | 天津大学 | A kind of preparation method of brominated alkanes |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100234653A1 (en) * | 2009-03-12 | 2010-09-16 | Chemtura Corporation | Processes for making alkyl halides |
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- 2021-07-27 CN CN202110851429.1A patent/CN113563155B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3981938A (en) * | 1974-07-08 | 1976-09-21 | The Dow Chemical Company | Method for producing dry alkyl halides |
| CN102010288A (en) * | 2010-08-20 | 2011-04-13 | 寿光市鲁源盐化有限公司 | Method for producing allyl bromide |
| CN104058926A (en) * | 2014-06-04 | 2014-09-24 | 蚌埠团结日用化学有限公司 | Production technique for synthesizing 1-bromo-3-chloropropane |
| CN107973692A (en) * | 2017-11-24 | 2018-05-01 | 天津大学 | A kind of preparation method of brominated alkanes |
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