CN113563155A - Bromopropylene synthesis method - Google Patents
Bromopropylene synthesis method Download PDFInfo
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- CN113563155A CN113563155A CN202110851429.1A CN202110851429A CN113563155A CN 113563155 A CN113563155 A CN 113563155A CN 202110851429 A CN202110851429 A CN 202110851429A CN 113563155 A CN113563155 A CN 113563155A
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- reaction kettle
- bromopropene
- gas
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- NNQDMQVWOWCVEM-UHFFFAOYSA-N 1-bromoprop-1-ene Chemical group CC=CBr NNQDMQVWOWCVEM-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 238000001308 synthesis method Methods 0.000 title claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 88
- 239000003513 alkali Substances 0.000 claims abstract description 40
- 239000007788 liquid Substances 0.000 claims abstract description 38
- 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
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 25
- 239000002994 raw material Substances 0.000 claims abstract description 22
- 238000005406 washing Methods 0.000 claims abstract description 19
- 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
- 239000000047 product Substances 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 25
- 238000003860 storage Methods 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 11
- 230000002194 synthesizing effect Effects 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
- 238000007599 discharging Methods 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 230000035484 reaction time Effects 0.000 abstract description 5
- 239000002351 wastewater Substances 0.000 abstract description 5
- 230000008569 process Effects 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 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
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 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
- 238000007792 addition Methods 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000013067 intermediate product 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
- 239000002304 perfume Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Images
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
Abstract
The application discloses a bromopropylene synthesis method, which comprises the following steps: 1) adding a liquid raw material into a reaction kettle; the liquid raw material contains allyl alcohol liquid; 2) introducing reaction gas into a reaction kettle, and continuously stirring the 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 in the step 2) is finished, standing and layering the intermediate reaction liquid I formed in the step 2); after standing and layering, releasing hydrobromic acid at the bottom to obtain intermediate reaction liquid II; 4) adding alkali liquor into the reaction kettle, performing alkali washing on the intermediate reaction liquid II obtained after the step 3), and obtaining intermediate reaction liquid III after alkali washing. The bromopropene synthesis method disclosed by the invention can effectively reduce the reaction time and the generation amount of wastewater, and the produced bromopropene product has high purity.
Description
Technical Field
The invention relates to a bromopropylene synthesis method, and belongs to the field of chemical production.
Background
Bromopropylene, an organic compound, has an unpleasant pungent odor, is mainly used for organic synthesis, is used as an intermediate of resin and perfume, and has certain harm to the environment. In the conventional art, methods for producing bromopropene include allyl alcohol bromination and propene bromination. In the allyl alcohol bromination process, hydrobromic acid is charged into a reaction tank, and sulfuric acid and allyl alcohol are added while stirring. Heating and refluxing for 2h, distilling the distillate when heating to 8 deg.C, and collecting the distillate at 68-73 deg.C. After washing, dehydrating with anhydrous sodium sulfate, and filtering to obtain allyl bromide. In the propylene bromination method, hydrobromic acid and allyl alcohol are mixed and then react. The production process of the two methods has long reaction time and the purity of the produced product is lower; the product obtained by the reaction needs to be rectified and purified, and the purity of the rectified product is low, so that the high-purity bromopropylene product is difficult to produce. And a certain amount of wastewater is generated when hydrobromic acid and allyl alcohol are mixed for production, and the generated wastewater is more.
Disclosure of Invention
The invention provides a bromopropene synthesis method, which is used for synthesizing a bromopropene product by a simple method, can effectively reduce the reaction time and the generation amount of waste water, and the produced bromopropene product has high purity.
The technical scheme adopted by the invention is that the bromopropylene synthesis method comprises the following steps:
1) adding a liquid raw material into a reaction kettle; the liquid raw material contains allyl alcohol liquid;
2) introducing reaction gas into a reaction kettle, and continuously stirring the 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 in the step 2) is finished, standing and layering the intermediate reaction liquid I formed in the step 2); after standing and layering, releasing hydrobromic acid at the bottom to obtain intermediate reaction liquid II;
4) adding alkali liquor into the reaction kettle, performing alkali washing on the intermediate reaction liquid II obtained after the step 3), and obtaining intermediate reaction liquid III after the alkali washing;
5) naturally settling the intermediate reaction liquid III obtained after the alkali 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 bromopropylene finished product; transferring the bromopropylene finished product to a bromopropylene finished product tank for storage.
Preferably, in the above bromopropene synthesis method, in the step 2), the reaction is finished when WAB in the liquid in the reaction kettle is greater than or equal to 99%.
Preferably, in the bromopropene synthesis method, in the step 2), the reaction gas introduced into the reaction kettle comprises hydrogen bromide gas and excess hydrogen, and the concentration of the hydrogen bromide gas in the reaction gas is greater than or equal to 90%; in the step 2), the reaction gas is introduced into the reaction kettle at a speed of 15-17m3/h。
Preferably, in 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 percent; the liquid raw materials are metered into the reaction kettle at one time.
Optimally, in the bromopropylene synthesis method, in the step 2), 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 between 0.01 and 0.03MPa, the reaction temperature is between 25 and 35 ℃, and the stirring speed is 140 r/min.
Preferably, in the above method for synthesizing bromopropylene, in step 1) and 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.
preferably, in the bromopropylene synthesis method, when standing and layering are performed in the step 3), standing is performed for 30min, and the standing can be stopped after the solution is completely layered.
Preferably, in the bromopropylene 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 added into the reaction kettle is as follows: adding 1Kg of alkali liquor into the reaction kettle per 150L of the reaction kettle; 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 liquid is 1: 125.
Preferably, in the bromopropene synthesis method, in the step 6), the lower material is dried by a molecular sieve dryer at normal temperature, and the moisture content of the dried bromopropene finished product is less than or equal to 1000 ppm.
The application has the advantages that:
in the technical scheme of this application, use hydrogen bromide gas and allyl alcohol liquid to react synthetic bromopropene, use hydrobromic acid among the prior art, the product yield in the method reaction of this application is high (the yield is about 95%), can effectual reduction reaction time, improvement production efficiency. And because the reaction time is reduced, the energy consumption can be reduced, and the reaction cost is further reduced. The synthesis method does not need rectification in the production process, reduces the use amount of the rectified steam and reduces the energy consumption. No wastewater is generated in the synthesis process, the pollution is reduced, and the cost for the later-stage wastewater treatment can be reduced. The purity of the bromopropylene 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 better.
Drawings
FIG. 1 is a flow diagram of a bromopropene synthesis process in the present application.
Detailed Description
The technical features of the present invention will be further explained with reference to the accompanying drawings and specific embodiments.
Example 1:
as shown in the figure, the invention is a bromopropene synthesis method, which comprises the following steps:
step 1) adding liquid raw materials into a reaction kettle in one-time metering mode; the liquid raw material contains an 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 the reaction kettle at a speed of 16m3The 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 the liquid raw materials in the reaction kettle until the reaction is finished to obtain an intermediate reaction solution 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 130 r/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 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.
step 3) after the reaction in the step 2) is finished, standing and layering the intermediate reaction liquid I formed in the step 2); after standing and layering, releasing hydrobromic acid at the bottom to obtain intermediate reaction liquid 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, performing alkali washing on the intermediate reaction liquid II obtained after the step 3), and obtaining intermediate reaction liquid III after alkali washing;
the concentration of the alkali liquor added into the reaction kettle is 32 percent; the weight of alkali liquor in the reaction kettle is as follows: adding 1Kg of alkali liquor into the reaction kettle per 150L of the reaction kettle; 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 liquid is 1: 125.
Step 5) naturally settling the intermediate reaction liquid III obtained after the alkali washing in the step 4), transferring a lower material obtained after settling into a semi-finished product storage tank, and discharging an upper alkali liquor obtained after settling into an alkali liquor storage tank;
step 6) adding the lower material transferred to 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 bromopropylene is 999.9ppm to obtain a bromopropylene finished product; transferring the bromopropylene finished product to a bromopropylene finished product tank for storage.
The step 1) and the step 2) are reaction processes, mainly refer to hydrogen bromide gas after impurity removal and allyl alcohol, react under certain reaction temperature, the apparatus for accomplishing the process mainly includes: a glass lining reaction kettle and a material transferring pump.
Step 3), step 4) and step 5) are alkaline washing processes, which mainly means that after the allyl bromide produced after the reaction is separated from the acid phase, the allyl bromide is washed, and the acid contained in the allyl bromide is subjected to neutralization reaction with liquid alkali, so that the allyl bromide is in a stable process. The equipment for completing the process mainly comprises: a glass lining reaction kettle, a material transferring pump and an intermediate product storage tank (glass lining).
And step 6) is a drying process, which mainly refers to a process that the allyl bromide product containing certain moisture meets the moisture requirement of the product after being dried. The equipment for completing the process mainly comprises: drying tower, material transferring pump and other equipment.
The reaction data in the embodiment is the optimal reaction data of the application, the production of the finished bromopropylene product is carried out under the condition, the lower production loss and production energy consumption can be ensured under the condition of ensuring the quality of the finished bromopropylene product, and the comprehensive economic benefit is higher than that of other embodiments.
Example 2
This example differs from example 1 in that:
the reaction was completed when the WAB concentration in the liquid in the reaction tank was 99.4%.
The concentration of hydrogen bromide gas in the reaction gas is 92%; in step 2), the reaction gas is introduced into the reaction vessel at a rate of 15m3/h。
The concentration of the allyl alcohol liquid in the liquid raw materials 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 120 r/min. The water content of the dried bromopropylene finished product was 999.8 ppm.
Example 3
This example differs from examples 1 and 2 in that: the reaction was complete when the WAB in the liquid in the kettle was 99.7%.
The concentration of hydrogen bromide gas in the reaction gas is 94%; in step 2), the reaction gas was introduced into the reactor at a rate of 17m3H is used as the reference value. The concentration of the allyl alcohol liquid in the liquid raw materials 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 140 r/min. The water content of the dried bromopropylene finished product is 999 ppm.
It is to be understood that the above description is not intended to limit the present invention, and the present invention is not limited to the above examples, and those skilled in the art should understand that they can make various changes, modifications, additions and substitutions within the spirit and scope of the present invention.
Claims (9)
1. A bromopropylene synthesis method is characterized in that: the method comprises the following steps:
1) adding a liquid raw material into a reaction kettle; the liquid raw material contains allyl alcohol liquid;
2) introducing reaction gas into a reaction kettle, and continuously stirring the 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 in the step 2) is finished, standing and layering the intermediate reaction liquid I formed in the step 2); after standing and layering, releasing hydrobromic acid at the bottom to obtain intermediate reaction liquid II;
4) adding alkali liquor into the reaction kettle, performing alkali washing on the intermediate reaction liquid II obtained after the step 3), and obtaining intermediate reaction liquid III after the alkali washing;
5) naturally settling the intermediate reaction liquid III obtained after the alkali 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 bromopropylene finished product; transferring the bromopropylene finished product to a bromopropylene finished product tank for storage.
2. The method for synthesizing bromopropene according to claim 1, wherein: in the step 2), the reaction is finished when WAB in the liquid in the reaction kettle is more than or equal to 99%.
3. The method for synthesizing bromopropene according to claim 1, wherein: in the step 2), introducing reaction gas into the reaction kettle, wherein the concentration of the hydrogen bromide gas in the reaction gas is more than or equal to 90 percent, and the reaction gas comprises hydrogen bromide gas and excessive hydrogen; in the 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, wherein: the concentration of the allyl alcohol liquid in the liquid raw materials 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, wherein: in the step 2), continuously introducing reaction gas into the reaction kettle; in the reaction process of the step 2), the pressure in the reaction kettle is kept between 0.01 and 0.03MPa, the reaction temperature is between 25 and 35 ℃, and the stirring speed is 140 r/min.
6. The method for synthesizing bromopropene according to claim 1, wherein: 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.
7. the method for synthesizing bromopropene according to claim 1, wherein: and (3) when standing and layering are carried out in the step 3), standing for 30min, and stopping standing after the solution is completely layered.
8. The method for synthesizing bromopropene according to claim 1, wherein: 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 added into the reaction kettle is as follows: adding 1Kg of alkali liquor into the reaction kettle per 150L of the reaction kettle; 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 liquid is 1: 125.
9. The method for synthesizing bromopropene according to claim 1, wherein: and 6), drying the lower material at normal temperature by using a molecular sieve dryer, wherein the moisture content of the dried bromopropylene finished product is less than or equal to 1000 ppm.
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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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Citations (5)
| 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 |
| US20100234653A1 (en) * | 2009-03-12 | 2010-09-16 | Chemtura Corporation | Processes for making 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 |
-
2021
- 2021-07-27 CN CN202110851429.1A patent/CN113563155B/en active Active
Patent Citations (5)
| 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 |
| US20100234653A1 (en) * | 2009-03-12 | 2010-09-16 | Chemtura Corporation | Processes for making 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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