CN105418565B - A kind of production method of tetrabromophthalic anhydride - Google Patents
A kind of production method of tetrabromophthalic anhydride Download PDFInfo
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- CN105418565B CN105418565B CN201510895658.8A CN201510895658A CN105418565B CN 105418565 B CN105418565 B CN 105418565B CN 201510895658 A CN201510895658 A CN 201510895658A CN 105418565 B CN105418565 B CN 105418565B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/89—Benzo [c] furans; Hydrogenated benzo [c] furans with two oxygen atoms directly attached in positions 1 and 3
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Abstract
The invention belongs to chemical field, is related to fine chemistry industry organic synthesis, more particularly to a kind of production method of tetrabromophthalic anhydride.Comprise the following steps：Oleum is added in reaction kettle, weak lewis acid catalyst stirring is added after adding phthalic anhydride dissolving, the mode divided three sections of temperature programmings and add reactant three times is reacted, and the filter cake for filtering gained is added in sodium hydrate aqueous solution, add activated carbon stirring, filtering；Filtrate adds in aqueous hydrochloric acid solution and is acidified, and is extracted with organic solvent after cooling, under vacuum distills organic solvent, high temperature dehydration.Multistep reaction with the prior art is compared, and present invention process product appearance color is pure white, sulfate radical content is low, sterling purity is high, and product purity is high, and impurity content is low, high income.
Description
Technical field
The invention belongs to chemical field, is related to fine chemistry industry organic synthesis, more particularly to a kind of producer of tetrabromophthalic anhydride
Method.
Background technology
Tetrabromophthalic anhydride is a kind of important fine chemistry industry organic synthesis material, as additive flame retardant and three two White-jade-worn-on-belt of oxidation
Coordinate, for polystyrene, polypropylene, polyethylene and ABG resins, and can be used for other engineering plastics and synthetic material, may be used also
Synthesis for other fine chemicals.It is how to produce in place of the difficult point of tetrabromophthalic anhydride production with brominated amount height, adds
Dosage is few, good flame retardation effect, and has higher degree of unsaturation, existing high crosslink density, light, heat endurance number and fabulous
Heat resistance, also with mechanical performance, the product of electrical insulation capability.And how to accomplish that production process and product toxicity are low, pollute
Environment is small.Tetrabromophthalic anhydride tool has been widely used, and can not only be used for preferable reactive flame retardant, can also be used as additive flame retardant
Agent.Tetrabromophthalic anhydride can be used for the fields such as polyester, unsaturated polyester (UP), epoxy resin as reactive flame retardant.Existing tetrabromophthalic anhydride
The product colour of production is mostly yellow, and sulfate radical content is high, and product purity is low, seriously constrains tetrabromophthalic anhydride in engineering plastics
Etc. the application in industry.
The content of the invention
The present invention is in view of the shortcomings of the prior art, provide a kind of production method of new tetrabromophthalic anhydride.In order to reach above-mentioned mesh
, the technical scheme is that：
A kind of production method of tetrabromophthalic anhydride, comprises the following steps：
(1) 50% oleum is added in reaction kettle, adds after phthalic anhydride is stirred to phthalic anhydride all dissolving and add weak Louis
This acid catalyst, continues stirring to being uniformly mixed, obtains mixture a；
(2) mode divided the mixture a in step (1) to three sections of temperature programmings and add reactant three times is reacted,
First segment warming temperature is 30-50 DEG C, and the quality for adding bromine is the 50-60% of phthalic anhydride；Second segment warming temperature is 60-70
DEG C, the quality for adding bromine is the 50-60% of phthalic anhydride；3rd section of warming temperature is 80-120 DEG C, and the quality for adding bromine is benzene
The 40-60% of acid anhydride, adds tetrabromophthalic anhydride crystal seed, it is phthalic anhydride quality that tetrabromophthalic anhydride crystal seed, which adds quality, before adding bromine at the 3rd section
5-10%；Reaction end obtains mixture b；
(3) the mixture b in step (2) is cooled down and filtered, the filter cake for filtering gained is added to 25-35% sodium hydroxides
In aqueous solution, adjust 80-85 DEG C of temperature and adjust pH value to 8-9, then add activated carbon and stir to being mixed
Thing c；
(4) the mixture c in step (3) is filtered；Filtrate is added in 30-35% aqueous hydrochloric acid solutions, adjusts the temperature to 93-
96 DEG C and adjust pH value and be acidified to 0-1, mixture d is obtained after cooling；
(5) the mixture d in step (4) is extracted with organic solvent, obtains four bromophthalic acid crude product e；
(6) four bromophthalic acid crude product e in step (5) are under vacuum distilled organic solvent, then
High temperature dehydration, obtains phenyl tetrabromide acid anhydride f.
Preferably, 50% oleum and phthalic anhydride mass ratio are (5-8) in step (1)：1.
It is at least one in butter of tin, titanium tetrachloride, antimony trichloride as weak lewis acid in the preferred step (1)
Kind, the weak lewis acid catalyst adds the 1-5% that quality accounts for phthalic anhydride.
Preferably, when the first segment reaction time is 4-6 small in the step (2), the second segment reaction time is small for 4-5
When, when the 3rd section of reaction time is 5-6 small.
Preferably, it is 50-60 DEG C that temperature is filtered in the step (3), activated carbon adds the 5- that quality accounts for phthalic anhydride quality
10%.
Preferably, the organic solvent in the step (5) is ethyl acetate, acetone, at least one of butanone, matter is added
Measure to add 5-10 times of phthalic anhydride quality.
Preferably, in the step (6) under vacuum by organic solvent distill vacuum be 0.09-
0.095MPa, vapo(u)rizing temperature are 100-120 DEG C.
Preferably, the temperature of step (6) the high temperature dehydration is 150-200 DEG C.
Compared with prior art, the advantages and positive effects of the present invention are, present invention production phenyl tetrabromide acid anhydride, first by benzene
Acid anhydride is dissolved in 50% oleum, under the action of catalyst, the sectional temperature-controlled bromination reaction in reaction solution, by reaction mass into
Salt, decoloration, acidifying, extraction, distillation, dehydration obtain product.Multistep reaction with the prior art is compared, outside present invention process product
Sight color is pure white, sulfate radical content is low, sterling purity is high, and product purity is high, and impurity content is low, high income.Present invention production
Product yield reaches more than 95%, and purity reaches more than 98.5%, effectively increases the quality of product.Product of the present invention has brominated
The characteristics of amount is high, additive amount is few, good flame retardation effect, and there is higher degree of unsaturation, existing high crosslink density, light, heat are steady
Qualitative number and fabulous heat resistance, also with mechanical performance, electrical insulation capability.Toxicity is low, free from environmental pollution.This product by using extensively
On the way, preferable reactive flame retardant is can not only be used for, can also be used as additive flame retardant.
Embodiment
To better understand the objects, features and advantages of the present invention, with reference to specific embodiment pair
The present invention is described further.It should be noted that in the case where there is no conflict, the spy in embodiments herein and embodiment
Sign can be mutually combined.
Many details are elaborated in the following description to facilitate a thorough understanding of the present invention, still, the present invention may be used also
With using implementing different from other modes described here, therefore, the present invention is not limited to the specific of specification is described below
The limitation of embodiment.
Embodiment 1, the present embodiment provides a kind of tetrabromophthalic anhydride production method.50% oleum 50g is added first anti-
Answer in kettle, add after phthalic anhydride 10g is stirred to phthalic anhydride all dissolving and add stannic chloride catalyst 0.1g, it is equal to mixing to continue stirring
Even, the mode then divided three sections of temperature programmings and add reactant three times is reacted, and first segment warming temperature is 30 DEG C, is added
The quality of bromine is 5g, when the reaction time is 4 small；Second segment warming temperature is 60 DEG C, and the quality for adding bromine is 5g, during reaction
Between for 4 it is small when；3rd section of warming temperature is 80 DEG C, and the quality for adding bromine is the 4g of phthalic anhydride, the reaction time for 5 it is small when, the
Tetrabromophthalic anhydride crystal seed is first added before three sections of addition bromines, it is 0.5g that tetrabromophthalic anhydride crystal seed, which adds quality,；It is cooled to after reaction
50 DEG C and filter.Suction filtration device used in the present invention is using quartz material, and 25*25's crosses filter block seamless combination, its bore phase
When in the sieves of 120 mesh, material transfering device is by 2m enamel pipelines, nitrogen air intake is equipped with pipeline, by being passed through nitrogen
Gas prevents the generation of inner pipeline plug plug phenomenon.The filter cake for filtering gained is added in 25% sodium hydrate aqueous solution, adjusts temperature
And pH value is adjusted to 8, then add activated carbon 0.5g and stir to being uniformly mixed, filtrate is added into 30% hydrochloric acid water after filtering by 80 DEG C
In solution, adjust the temperature to 93 DEG C and adjust pH value and be acidified to 0.1, ethyl acetate 50g is added after being cooled to room temperature and is carried out
Extraction, obtains four bromophthalic acid crude products.Then by acetic acid under conditions of vacuum is 0.09MPa, temperature is 100 DEG C
Ethyl ester distills, and then carries out high temperature dehydration at 150 DEG C, obtains phenyl tetrabromide acid anhydride finished product.
Embodiment 2, the present embodiment provides a kind of tetrabromophthalic anhydride production method.50% oleum 80g is added first anti-
Answer in kettle, add after phthalic anhydride 10g is stirred to phthalic anhydride all dissolving and add TiCl 4 catalyst 0.5g, it is equal to mixing to continue stirring
Even, the mode then divided three sections of temperature programmings and add reactant three times is reacted, and first segment warming temperature is 50 DEG C, is added
The quality of bromine is 6g, when the reaction time is 6 small；Second segment warming temperature is 70 DEG C, and the quality for adding bromine is 6g, during reaction
Between for 5 it is small when；3rd section of warming temperature is 120 DEG C, and the quality for adding bromine is the 6g of phthalic anhydride, the reaction time for 6 it is small when, the
Tetrabromophthalic anhydride crystal seed is first added before three sections of addition bromines, it is 1g that tetrabromophthalic anhydride crystal seed, which adds quality,；60 are cooled to after reaction
DEG C and filter, the Suction filtration device used in the present invention is using quartz material, and 25*25's crosses filter block seamless combination, its bore is suitable
In the sieves of 120 mesh, material transfering device is by 2m enamel pipelines, nitrogen air intake is equipped with pipeline, by being passed through nitrogen
Prevent the generation of inner pipeline plug plug phenomenon.The filter cake for filtering gained is added in 35% sodium hydrate aqueous solution, adjusts temperature 85
DEG C and adjust pH value to 9, then add activated carbon 1g and stir to being uniformly mixed, filtrate is added into 35% aqueous hydrochloric acid solution after filtering
In, adjust the temperature to 96 DEG C and adjust pH value and be acidified to 1, acetone 100g is added after being cooled to room temperature and is extracted, is obtained
Four bromophthalic acid crude products.Then acetone is distilled under conditions of vacuum is 0.095MPa, temperature is 120 DEG C, so
High temperature dehydration is carried out at 200 DEG C afterwards, obtains phenyl tetrabromide acid anhydride finished product.
Embodiment 3, the present embodiment provides a kind of tetrabromophthalic anhydride production method.50% oleum 60g is added first anti-
Answer in kettle, add after phthalic anhydride 10g is stirred to phthalic anhydride all dissolving and add antimony trichloride catalyst 0.3g, it is equal to mixing to continue stirring
Even, the mode then divided three sections of temperature programmings and add reactant three times is reacted, and first segment warming temperature is 40 DEG C, is added
The quality of bromine is 5.5g, when the reaction time is 4.5 small；Second segment warming temperature is 68 DEG C, and the quality for adding bromine is 5.2g,
When reaction time is 4.4 small；3rd section of warming temperature is 105 DEG C, and the quality for adding bromine is the 4.9g of phthalic anhydride, and the reaction time is
5.5 it is small when, first add tetrabromophthalic anhydride crystal seed before adding bromine at the 3rd section, it is 0.8g that tetrabromophthalic anhydride crystal seed, which adds quality,；Reaction
After be cooled to 55 DEG C and filter, the Suction filtration device used in the present invention is using quartz material, and 25*25's crosses the seamless knot of filter block
Closing, for its bore equivalent to the sieves of 120 mesh, material transfering device is by 2m enamel pipelines, and nitrogen air intake is equipped with pipeline,
The generation of inner pipeline plug plug phenomenon is prevented by being passed through nitrogen.The filter cake for filtering gained is added to 30% sodium hydrate aqueous solution
In, adjust 82 DEG C of temperature and adjust pH value to 8.2, then add activated carbon 0.6g and stir to being uniformly mixed, by filtrate after filtering
Add in 33% aqueous hydrochloric acid solution, adjust the temperature to 95 DEG C and adjust pH value and be acidified to 0.6, fourth is added after being cooled to room temperature
Ketone 80g is extracted, and obtains four bromophthalic acid crude products.Then in the bar that vacuum is 0.093MPa, temperature is 110 DEG C
Butanone is distilled under part, then high temperature dehydration is carried out at 165 DEG C, obtains phenyl tetrabromide acid anhydride finished product.
Embodiment 4, the present embodiment provides a kind of tetrabromophthalic anhydride production method.50% oleum 75g is added first anti-
Answer in kettle, add after phthalic anhydride 10g is stirred to phthalic anhydride all dissolving and add stannic chloride catalyst 0.3g, it is equal to mixing to continue stirring
Even, the mode then divided three sections of temperature programmings and add reactant three times is reacted, and first segment warming temperature is 35 DEG C, is added
The quality of bromine is 5.6g, when the reaction time is 4 small；Second segment warming temperature is 66 DEG C, and the quality for adding bromine is 5.8g, instead
When being 4 small between seasonable；3rd section of warming temperature is 92 DEG C, and the quality for adding bromine is the 5.5g of phthalic anhydride, and the reaction time is small for 4
When, tetrabromophthalic anhydride crystal seed is first added before adding bromine at the 3rd section, it is 0.8g that tetrabromophthalic anhydride crystal seed, which adds quality,；After reaction
It is cooled to 50 DEG C and filters, the Suction filtration device used in the present invention is using quartz material, and 25*25's crosses filter block seamless combination, its
For bore equivalent to the sieves of 120 mesh, material transfering device is by 2m enamel pipelines, is equipped with nitrogen air intake at pipeline, passes through
Being passed through nitrogen prevents the generation of inner pipeline plug plug phenomenon.The filter cake for filtering gained is added in 30% sodium hydrate aqueous solution, is adjusted
85 DEG C of temperature of section simultaneously adjusts pH value to 8.5, then adds activated carbon 0.8g and stirs to being uniformly mixed, adds filtrate after filtering
In 35% aqueous hydrochloric acid solution, adjust the temperature to 95 DEG C and adjust pH value and be acidified to 0, butanone 100g is added after being cooled to room temperature
Extracted, obtain four bromophthalic acid crude products.Then under conditions of vacuum is 0.095MPa, temperature is 110 DEG C
Butanone is distilled, then high temperature dehydration is carried out at 180 DEG C, obtains phenyl tetrabromide acid anhydride finished product.
It is as shown in the table to the tetrabromophthalic anhydride finished product detection result that is obtained in each embodiment：
The above described is only a preferred embodiment of the present invention, being not the limitation for making other forms to the present invention, appoint
What those skilled in the art changed or be modified as possibly also with the technology contents of the disclosure above equivalent variations etc.
Effect embodiment is applied to other fields, but every without departing from technical solution of the present invention content, the technical spirit according to the present invention
Any simple modification, equivalent variations and the remodeling made to above example, still fall within the protection domain of technical solution of the present invention.
Claims (8)
1. a kind of production method of tetrabromophthalic anhydride, it is characterised in that comprise the following steps：
(1) 50% oleum is added in reaction kettle, adds after phthalic anhydride is stirred to phthalic anhydride all dissolving and add weak lewis acid
Catalyst, continues stirring to being uniformly mixed, obtains mixture a；
(2) mode divided the mixture a in step (1) to three sections of temperature programmings and add reactant three times is reacted, and first
Section warming temperature is 30-50 DEG C, and the quality for adding bromine is the 50-60% of phthalic anhydride；Second segment warming temperature is 60-70 DEG C, is added
The quality for entering bromine is the 50-60% of phthalic anhydride；3rd section of warming temperature is 80-120 DEG C, and the quality for adding bromine is phthalic anhydride
40-60%, adds tetrabromophthalic anhydride crystal seed, it is phthalic anhydride quality that the tetrabromophthalic anhydride crystal seed, which adds quality, before adding bromine at the 3rd section
5-10%；Reaction end obtains mixture b；
(3) the mixture b in step (2) is cooled down and filtered, filtering the filter cake of gained, to be added to 25-35% sodium hydroxides water-soluble
In liquid, adjust 80-85 DEG C of temperature and adjust pH values to 8-9, then add activated carbon and stir to being uniformly mixed and obtain mixture c；
(4) the mixture c in step (3) is filtered；Filtrate is added in 30-35% aqueous hydrochloric acid solutions, adjusts the temperature to 93-96 DEG C
And adjust pH values and be acidified to 0-1, mixture d is obtained after cooling；
(5) the mixture d in step (4) is extracted with organic solvent, obtains four bromophthalic acid crude product e；
(6) four bromophthalic acid crude product e in step (5) are under vacuum distilled organic solvent, then high temperature
Dehydration, obtains phenyl tetrabromide acid anhydride f.
2. the production method of a kind of tetrabromophthalic anhydride according to claim 1, it is characterised in that 50% in the step (1)
Oleum and phthalic anhydride mass ratio are (5-8)：1.
A kind of 3. production method of tetrabromophthalic anhydride according to claim 1, it is characterised in that step (1) the Zhong Ruo roads
Lewis acid is at least one of butter of tin, titanium tetrachloride, antimony trichloride, and the weak lewis acid catalyst adds quality and accounts for
The 1-5% of phthalic anhydride.
4. the production method of a kind of tetrabromophthalic anhydride according to claim 1, it is characterised in that first in the step (2)
When the section reaction time is 4-6 small, when the second segment reaction time is 4-5 small, when the 3rd section of reaction time is 5-6 small.
5. the production method of a kind of tetrabromophthalic anhydride according to claim 1, it is characterised in that filtered in the step (3)
Temperature is 50-60 DEG C, and activated carbon adds the 5-10% that quality accounts for phthalic anhydride quality.
A kind of 6. production method of tetrabromophthalic anhydride according to claim 1, it is characterised in that having in the step (5)
Solvent is ethyl acetate, acetone, at least one of butanone, adds quality to add 5-10 times of phthalic anhydride quality.
7. the production method of a kind of tetrabromophthalic anhydride according to claim 1, it is characterised in that true in the step (6)
By the vacuum that organic solvent distills be 0.09-0.095MPa under empty condition, vapo(u)rizing temperature is 100-120 DEG C.
A kind of 8. production method of tetrabromophthalic anhydride according to claim 1, it is characterised in that step (6) high temperature
The temperature of dehydration is 150-200 DEG C.
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|---|---|---|---|---|
| US5288879A (en) * | 1992-09-28 | 1994-02-22 | Ethyl Corporation | Tetrahalophthalic anhydride process |
| IL115814A (en) * | 1995-10-30 | 1999-03-12 | Bromine Compounds Ltd | Purification of 4-bromophthalic anhydride |
| CN102924361A (en) * | 2012-11-07 | 2013-02-13 | 山东润科化工股份有限公司 | Synthetic method for N,N-Ethylene-Bis(bromophthalimide) |
-
2015
- 2015-12-07 CN CN201510895658.8A patent/CN105418565B/en active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5288879A (en) * | 1992-09-28 | 1994-02-22 | Ethyl Corporation | Tetrahalophthalic anhydride process |
| IL115814A (en) * | 1995-10-30 | 1999-03-12 | Bromine Compounds Ltd | Purification of 4-bromophthalic anhydride |
| CN102924361A (en) * | 2012-11-07 | 2013-02-13 | 山东润科化工股份有限公司 | Synthetic method for N,N-Ethylene-Bis(bromophthalimide) |
Non-Patent Citations (2)
| Title |
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| I2-AlCl3催化合成四溴苯酐的工艺研究;熊鹰等;《精细化工中间体》;200610;第36卷(第5期);57-59，66 * |
| 四溴苯酐合成新方法研究;刘展鹏等;《化学试剂》;2005;第27卷(第1期);44-46 * |
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