CN112979435A - Tetrabromo ether and preparation method and application thereof - Google Patents
Tetrabromo ether and preparation method and application thereof Download PDFInfo
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- CN112979435A CN112979435A CN202110216884.4A CN202110216884A CN112979435A CN 112979435 A CN112979435 A CN 112979435A CN 202110216884 A CN202110216884 A CN 202110216884A CN 112979435 A CN112979435 A CN 112979435A
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- tetrabromobisphenol
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- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title abstract description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 69
- 239000002904 solvent Substances 0.000 claims abstract description 30
- 238000006266 etherification reaction Methods 0.000 claims abstract description 26
- 235000011121 sodium hydroxide Nutrition 0.000 claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- OWXJKYNZGFSVRC-NSCUHMNNSA-N (e)-1-chloroprop-1-ene Chemical compound C\C=C\Cl OWXJKYNZGFSVRC-NSCUHMNNSA-N 0.000 claims abstract description 15
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 claims abstract description 15
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000001035 drying Methods 0.000 claims abstract description 15
- 239000007788 liquid Substances 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 13
- 239000011259 mixed solution Substances 0.000 claims abstract description 13
- 239000002994 raw material Substances 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 11
- 238000001914 filtration Methods 0.000 claims abstract description 11
- JHJUYGMZIWDHMO-UHFFFAOYSA-N 2,6-dibromo-4-(3,5-dibromo-4-hydroxyphenyl)sulfonylphenol Chemical compound C1=C(Br)C(O)=C(Br)C=C1S(=O)(=O)C1=CC(Br)=C(O)C(Br)=C1 JHJUYGMZIWDHMO-UHFFFAOYSA-N 0.000 claims abstract description 9
- OJPSFJLSZZTSDF-UHFFFAOYSA-N 3-ethoxyprop-1-ene Chemical compound CCOCC=C OJPSFJLSZZTSDF-UHFFFAOYSA-N 0.000 claims abstract description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003513 alkali Substances 0.000 claims abstract description 4
- 239000000706 filtrate Substances 0.000 claims description 12
- 239000003063 flame retardant Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000003912 environmental pollution Methods 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 238000005457 optimization Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 238000004811 liquid chromatography Methods 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- 238000004064 recycling Methods 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 230000001737 promoting effect Effects 0.000 description 5
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- CMQUQOHNANGDOR-UHFFFAOYSA-N 2,3-dibromo-4-(2,4-dibromo-5-hydroxyphenyl)phenol Chemical compound BrC1=C(Br)C(O)=CC=C1C1=CC(O)=C(Br)C=C1Br CMQUQOHNANGDOR-UHFFFAOYSA-N 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000004794 expanded polystyrene Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the technical field of tetrabromoether preparation, and discloses tetrabromoether, a preparation method and application thereof, wherein the preparation method comprises the following steps: s1, taking tetrabromobisphenol A or tetrabromobisphenol S as a raw material, adding the raw material into a solvent formed by ethyl allyl ether or methyl tert-butyl ether, and dissolving to obtain a mixed solution; s2, sequentially adding caustic soda flakes and water into the mixed solution, and reacting to generate monosodium salt; s3, chloropropene is used as an etherification reagent, and the etherification reagent is added into the generated liquid in the step S2; s4, dropwise adding liquid caustic soda into the mixed liquor obtained in the step S3 to adjust the pH of the mixed liquor to 7-8, and then carrying out etherification reaction; s5, after the reaction of the step S4, crystallizing, filtering and drying to obtain target tetrabromoether; in conclusion, the method replaces the traditional solvent with the ether solvent, and adopts a mode of adding alkali in batches to carry out optimization reaction, thereby effectively achieving the effects of reducing environmental pollution, improving purity and reducing cost.
Description
Technical Field
The invention belongs to the technical field of preparation of tetrabromoether, and particularly relates to tetrabromoether, and a preparation method and application thereof.
Background
The tetrabromoether is an important reaction type flame retardant, is also a flame retardant crosslinking agent for synthesizing high polymer materials, and is mainly used for flame retardance of expanded polystyrene, unsaturated polyester, expanded polyurethane, ABS and the like. It can also be used as an intermediate for synthesizing other flame retardants, for example, the octabromoether can be prepared by further bromination as an intermediate.
At present, ethanol or methanol is mostly adopted as a solvent when the synthesis of the tetrabromoether is carried out industrially, and the problems of higher manufacturing cost and serious environmental pollution exist.
Disclosure of Invention
In view of the above, in order to solve the problems in the background art, the present invention aims to provide a tetrabromoether, and a preparation method and applications thereof.
In order to achieve the purpose, the invention provides the following technical scheme:
a preparation method of tetrabromoether comprises the following steps:
s1, taking tetrabromobisphenol A or tetrabromobisphenol S as a raw material, adding the raw material into a solvent formed by ethyl allyl ether or methyl tert-butyl ether, and dissolving to obtain a mixed solution;
s2, sequentially adding caustic soda flakes and water into the mixed solution, and reacting to generate monosodium salt;
s3, chloropropene is used as an etherification reagent, and the etherification reagent is added into the generated liquid in the step S2;
s4, dropwise adding liquid caustic soda into the mixed liquor obtained in the step S3 to adjust the pH of the mixed liquor to 7-8, then carrying out etherification reaction, and adjusting the pH of the reaction liquor to 7 after the etherification reaction;
s5, after the adjustment of the step S4, crystallizing, filtering and drying to obtain the target tetrabromoether.
Preferably, in the step S1, the ratio of 37-42: 200-230, the mixing of the raw material and the solvent is carried out.
Preferably, in the step S2, the ratio of 37-42: 120-150: mixing the raw material, water and flake caustic soda in a mass ratio of 6.5-6.7.
Preferably, in the step S3, the ratio of 3.1: 1, and after the temperature of the generated liquid in the step S2 is raised to 40-50 ℃, dropwise adding the chloropropene.
Preferably, in step S4, the liquid alkali is added dropwise, and the temperature of the mixed solution is raised to 50 to 60 ℃ to start the etherification reaction, wherein the etherification reaction time is 5 to 7 hours.
Preferably, in step S5, the drying is performed by hot water circulation double cone drying, and the drying temperature is 70-95 ℃.
Preferably, when the filtration in step S5 is performed, the solvent in the filtrate is recycled.
Tetrabromo ether is prepared from tetrabromo bisphenol A or tetrabromo bisphenol S serving as a raw material by the method disclosed above.
The application of the tetrabromoether prepared by the method disclosed above in preparing octabromoether or a flame retardant is disclosed.
Compared with the prior art, the invention has the following beneficial effects:
in the invention, an ether solvent composed of ethyl allyl ether or methyl tert-butyl ether is used as a reaction solvent to replace a methanol or ethanol solvent in the traditional preparation process; particularly, on the premise of preparing equivalent amount of the tetrabromoether, the consumption of the ether solvent is greatly lower than that of the alcohol solvent, so that the method can effectively reduce the solvent consumption, thereby effectively reducing the cost, and can recycle the reacted ether solvent, thereby further having the effect of reducing the environmental pollution. In addition, in the invention, the overall preparation process is further optimized by adding alkali in batches, so that the effect of improving the purity of the tetrabromoether prepared by the invention is achieved.
Detailed Description
The technical solutions in the embodiments of the present invention are 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. It is noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of example embodiments according to the present application. 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
S1, adding 68mL of ethyl allyl ether solution and 40g of tetrabromobisphenol A into a four-necked flask provided with a constant-pressure dropping funnel, an electric stirrer and a thermometer, and uniformly stirring by using the electric stirrer to dissolve the tetrabromobisphenol A to obtain a mixed solution;
s2, sequentially adding 3.2g of flake caustic soda (sodium hydroxide) and 80mL of water into a four-neck flask, uniformly stirring by using an electric stirrer, and reacting to generate monosodium salt;
s3, heating the resultant liquid obtained in the step S2 to 40 ℃, and then, dropwise adding 12.8g of chloropropene into the four-neck flask through a constant-pressure dropping funnel, wherein the chloropropene is used as an etherification reagent;
s4, after the dropwise addition is finished, slowly dropwise adding 3.2g of flake caustic soda and 80ml of aqueous solution into the four-neck flask through a constant-pressure dropping funnel, controlling the pH value to be 7-8, heating the solution to 50-60 ℃, and preserving heat for 5 hours to carry out etherification reaction;
s5, promoting the solution adjusted in the step S4 to crystallize by combining a elutriation technology with an epoxy curing agent accelerant BDMA, filtering after crystallization, recycling the filtrate to recycle the solvent in the filtrate, and drying the filter residue at the temperature of 60 ℃ to obtain the target tetrabromoether.
In this example, the amount of ethyl allyl ether solution consumed in the first reaction obtained after recovery was 10%, the total yield of tetrabromoether was 98%, and the purity by liquid chromatography was 99.4%.
Example 2
S1, adding 70mL of methyl tert-butyl ether solution and 40g of tetrabromobisphenol A into a four-necked flask provided with a constant-pressure dropping funnel, an electric stirrer and a thermometer, and uniformly stirring by the electric stirrer to dissolve the tetrabromobisphenol A to obtain a mixed solution;
s2, sequentially adding 3.1g of caustic soda flakes (sodium hydroxide) and 100mL of water into a four-neck flask, uniformly stirring by using an electric stirrer, and reacting to generate monosodium salt;
s3, heating the resultant liquid obtained in the step S2 to 43 ℃, and then dropwise adding 12.5g of chloropropene into the four-neck flask through a constant-pressure dropping funnel, wherein the chloropropene is used as an etherification reagent;
s4, after the dropwise addition is finished, slowly dropwise adding 3.1g of caustic soda flakes and 100ml of aqueous solution into the four-neck flask through a constant-pressure dropping funnel, controlling the pH value to be 7.3, heating the solution to 50-60 ℃, and preserving heat for 5 hours to carry out etherification reaction;
s5, promoting the solution adjusted in the step S4 to crystallize by a mode of combining a elutriation technology with an epoxy curing agent accelerant BDMA, filtering after crystallization, recycling the filtrate to recycle the solvent in the filtrate, and drying the filter residue at the temperature of 65 ℃ to obtain the target tetrabromoether.
In this example, the amount of methyl t-butyl ether solution consumed in the recovery of the one-shot reaction was 10.9%, the total yield of tetrabromoether was 91%, and the purity by liquid chromatography was 97%.
Example 3
S1, adding 73mL of ethyl allyl ether solution and 40g of tetrabromobisphenol A into a four-necked flask provided with a constant-pressure dropping funnel, an electric stirrer and a thermometer, and uniformly stirring by using the electric stirrer to dissolve the tetrabromobisphenol A to obtain a mixed solution;
s2, sequentially adding 3.3g of flake caustic soda (sodium hydroxide) and 125mL of water into a four-neck flask, uniformly stirring by using an electric stirrer, and reacting to generate monosodium salt;
s3, heating the resultant liquid obtained in the step S2 to 45 ℃, and then, dropwise adding 12.3g of chloropropene into the four-neck flask through a constant-pressure dropping funnel, wherein the chloropropene is used as an etherification reagent;
s4, after the dropwise addition is finished, slowly dropwise adding 3.2g of flake caustic soda and 125ml of aqueous solution into the four-neck flask through a constant-pressure dropping funnel, controlling the pH value to be 7.3, heating the solution to 50-60 ℃, and preserving heat for 5 hours to carry out etherification reaction;
s5, promoting the solution adjusted in the step S4 to crystallize by a mode of combining a elutriation technology with an epoxy curing agent accelerant BDMA, filtering after crystallization, recycling the filtrate to recycle the solvent in the filtrate, and drying the filter residue at the temperature of 65 ℃ to obtain the target tetrabromoether.
In this example, the amount of methyl t-butyl ether solution consumed in the recovery of the one-shot reaction was 10.3%, the total yield of tetrabromoether was 90%, and the purity by liquid chromatography was 93%.
Example 4
S1, adding 75mL of methyl tert-butyl ether solution and 40g of tetrabromobisphenol S into a four-necked flask provided with a constant-pressure dropping funnel, an electric stirrer and a thermometer, and uniformly stirring by the electric stirrer to dissolve tetrabromobisphenol A to obtain a mixed solution;
s2, sequentially adding 3.4g of caustic soda flakes (sodium hydroxide) and 150mL of water into a four-neck flask, uniformly stirring by using an electric stirrer, and reacting to generate monosodium salt;
s3, heating the resultant liquid obtained in the step S2 to 47 ℃, and then, dropwise adding 14g of chloropropene into the four-neck flask through a constant-pressure dropping funnel, wherein the chloropropene is used as an etherification reagent;
s4, after the dropwise addition is finished, slowly dropwise adding 3.4g of caustic soda flakes and 150ml of aqueous solution into the four-neck flask through a constant-pressure dropping funnel, controlling the pH value to be 7.7, heating the solution to 50-60 ℃, and preserving heat for 6.3 hours to carry out etherification reaction;
s5, promoting the solution adjusted in the step S4 to crystallize by combining a elutriation technology with an epoxy curing agent accelerant BDMA, filtering after crystallization, recycling the filtrate to recover the solvent in the filtrate for recycling, and drying the filter residue at the temperature of 68 ℃ to obtain the target tetrabromoether.
In this example, the amount of methyl t-butyl ether solution consumed in the recovery of the one-shot reaction was 11.1%, the total yield of tetrabromoether was 89%, and the purity by liquid chromatography was 90%.
Example 5
S1, adding 80mL of ethyl allyl ether solution and 40g of tetrabromobisphenol S into a four-necked flask provided with a constant-pressure dropping funnel, an electric stirrer and a thermometer, and uniformly stirring by using the electric stirrer to dissolve tetrabromobisphenol A to obtain a mixed solution;
s2, sequentially adding 3.5g of caustic soda flakes (sodium hydroxide) and 160mL of water into a four-neck flask, uniformly stirring by using an electric stirrer, and reacting to generate monosodium salt;
s3, heating the generated liquid in the step S2 to 50 ℃, and then dropping 16g of chloropropene into the four-neck flask through a constant-pressure dropping funnel, wherein the chloropropene is used as an etherification reagent;
s4, after the dropwise addition is finished, slowly dropwise adding 3.4g of caustic soda flakes and 160ml of aqueous solution into the four-neck flask through a constant-pressure dropping funnel, controlling the pH value to be 8, heating the solution to 50-60 ℃, and preserving the temperature for 5 hours to carry out etherification reaction;
s5, promoting the solution adjusted in the step S4 to crystallize by a mode of combining a elutriation technology with an epoxy curing agent accelerant BDMA, filtering after crystallization, recycling the filtrate to recycle the solvent in the filtrate, and drying the filter residue at the temperature of 75 ℃ to obtain the target tetrabromoether.
In this example, the amount of ethyl allyl ether solution consumed in the first reaction obtained after recovery was 10%, the total yield of tetrabromoether was 96%, and the purity by liquid chromatography was 98.3%.
Comparative example
Tetrabromobisphenol A or tetrabromobisphenol S is taken as a raw material, methanol or ethanol is taken as a solvent, and the tetrabromobisphenol A or tetrabromobisphenol S is subjected to etherification reaction, crystallization, filtration and drying to obtain the tetrabromobisphenol. In this comparative example, the amount of methanol or ethanol solvent consumed in the primary reaction obtained after recovery was 89%, the total yield of tetrabromoether was 89.7%, and the purity by liquid chromatography was 90.3%.
In conclusion, based on the examples 1 to 5 provided by the present invention, it can be seen that the tetrabromoether prepared by the method of the present invention has the advantages of low solvent consumption and high purity compared with the tetrabromoether prepared by the conventional process; therefore, the production cost can be effectively reduced, and the environmental pollution can be reduced.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (9)
1. A preparation method of tetrabromoether is characterized by comprising the following steps:
s1, taking tetrabromobisphenol A or tetrabromobisphenol S as a raw material, adding the raw material into a solvent formed by ethyl allyl ether or methyl tert-butyl ether, and dissolving to obtain a mixed solution;
s2, sequentially adding caustic soda flakes and water into the mixed solution, and reacting to generate monosodium salt;
s3, chloropropene is used as an etherification reagent, and the etherification reagent is added into the generated liquid in the step S2;
s4, dropwise adding liquid caustic soda into the mixed liquor obtained in the step S3 to adjust the pH of the mixed liquor to 7-8, then carrying out etherification reaction, and adjusting the pH of the reaction liquor to 7 after the etherification reaction;
s5, after the adjustment of the step S4, crystallizing, filtering and drying to obtain the target tetrabromoether.
2. The method of claim 1, wherein the reaction is carried out in the presence of a solvent selected from the group consisting of: in the step S1, at 37-42: 200-230, the mixing of the raw material and the solvent is carried out.
3. The method of claim 1, wherein the reaction is carried out in the presence of a solvent selected from the group consisting of: in the steps S2, S3, at 37-42: 120-150: mixing the raw material, water and flake caustic soda in a mass ratio of 6.5-6.7.
4. The method of claim 1, wherein the reaction is carried out in the presence of a solvent selected from the group consisting of: in the step S3, the ratio of 3.1: 1, and after the temperature of the generated liquid in the step S2 is raised to 40-50 ℃, dropwise adding the chloropropene.
5. The method of claim 1, wherein the reaction is carried out in the presence of a solvent selected from the group consisting of: in the step S4, the liquid alkali is added dropwise, and the temperature of the mixed solution is raised to 50 to 60 ℃ to start the etherification reaction, wherein the etherification reaction time is 5 to 7 hours.
6. The method of claim 1, wherein the reaction is carried out in the presence of a solvent selected from the group consisting of: in the step S5, the drying is performed by hot water circulation double cone drying, and the drying temperature is 70-95 ℃.
7. The method of claim 1, wherein the reaction is carried out in the presence of a solvent selected from the group consisting of: when the filtration in step S5 is performed, the solvent in the filtrate can be recycled after being recovered.
8. Tetrabromoether, characterized in that it is prepared from tetrabromobisphenol A or tetrabromobisphenol S by the process according to any of claims 1 to 7.
9. Use of a tetrabromoether as claimed in claim 8 in the preparation of octabromoether or flame retardants.
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