CN108774116A - A method of preparing phenylene dimethyl ether using iodomethane - Google Patents
A method of preparing phenylene dimethyl ether using iodomethane Download PDFInfo
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- CN108774116A CN108774116A CN201810536697.2A CN201810536697A CN108774116A CN 108774116 A CN108774116 A CN 108774116A CN 201810536697 A CN201810536697 A CN 201810536697A CN 108774116 A CN108774116 A CN 108774116A
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- iodomethane
- dimethyl ether
- phenylene dimethyl
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- potassium
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- 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
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
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- 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
Abstract
The present invention provides a kind of new methods preparing phenylene dimethyl ether using iodomethane, it is related to chemical industry synthesis field, the program includes mainly producing, methylating and distilation step for iodomethane, whole preparation process raw material and product low toxicity or nontoxic, reaction condition is mild, and security risk is small, and reaction yield is high, raw material potassium iodide can be recycled, while the byproduct of special high value is also prepared using iodomethane forming steps, greatly reduce production cost.
Description
Technical field
The present invention relates to chemical industry synthesis fields, refer in particular to a kind of method preparing phenylene dimethyl ether using iodomethane.
Background technology
Phenylene dimethyl ether, as one phenylene dimethyl ether of terephthaldehyde's ether also known as Isosorbide-5-Nitrae, paradimethoxybenzene, hydroquinone dimethyl ether with
And hydrogen ketone dimethyl ether etc., molecular formula is:C8H1002, molecular weight are:138.17, there is aromatic odor, be a kind of relatively conventional
Organic synthesis raw material, be usually used in fragrance, household chemicals, food, flavouring essence for tobacco etc. synthesis and prepare, also act as plastics and
Weather-proof dose of paint and the synthesis of some dyestuffs and medicine intermediate.
The product mainly has dimethyl suflfate normal pressure to methylate to methylate two synthesis technologies with halide pressurization at present
Route, dimethyl suflfate normal pressure route of methylation be using hydroquinone as starting material, in alkaline medium with highly basic at salt after
Replace again with dimethyl suflfate and obtain, the process recovery ratio is higher, and product quality is stablized, and reaction condition is mild, but raw materials used sulphur
Dimethyl phthalate is that hypertoxic product, higher price, and the methyl utilization rate in dimethyl suflfate only have 50%, generation sulfuric acid list first
A remaining methyl is no longer participate in reaction after ester sodium salt, so the unit consumption of dimethyl suflfate is higher, not only increases and is produced into
This, and increase the difficulty of wastewater treatment.
Invention content
The technical problem to be solved by the present invention is to：A kind of novel high income, environmentally protective phenylene dimethyl ether are provided
Synthesis technology.
In order to solve the above-mentioned technical problem, the invention discloses a kind of method preparing phenylene dimethyl ether using iodomethane, tools
Body includes the following steps：
S1, iodomethane are produced, reacted to be made using potassium iodide, methanol/aliphatic methyl ether, tricresyl phosphate kind substance as raw material
Iodomethane；
S2, methylate, using in benzenediol and S1 steps iodomethane and potassium hydroxide as raw material, occur methylation reaction
Formation includes target product phenylene dimethyl ether and the mixed system of potassium iodide；
S3, distillation, methylating to S2 is formed by mixed system and distills, isolated single target product benzene two
Methyl ether and it is circularly used for the potassium iodide that S1 iodomethane is produced.
Further, in the S2 demethylation steps, raw materials used benzenediol, potassium hydroxide and iodomethane three's mass ratio
For 1 ︰, 1.7~2 ︰ 4~5.
Further, in the S2 demethylation steps, reaction temperature is not higher than 30 DEG C, and reaction pressure is normal pressure.
Further, in the S2 demethylation steps, raw material iodomethane is fed by the way of being gradually added dropwise.
Further, in the S3 distilation steps, mixed system is formed by S2 methylation reactions using steam and is carried out
Distillation, until distillate is clarified without material, distillate is cooling, filters, is dry that white solid is target product benzene two
Methyl ether.
Further, in the S1 iodomethane forming steps, using potassium iodide, aliphatic methyl ether and phosphoric acid as raw material, three
Mass ratio be 1 ︰, 0.6~1.6 ︰ 1.2~2.4, wherein the H contained by phosphoric acid itself used3PO4Mass fraction is 85%.
Further, in the S1 iodomethane forming steps, aliphatic methyl ether is 3-MP or 3- methoxies
Base -1- propionic acid.
Further, in the S1 iodomethane forming steps, using potassium iodide, methanol and phosphoric acid as raw material, the quality of three
Than for 1 ︰, 0.2~0.4 ︰ 2~2.4, wherein the H contained by phosphoric acid itself used3PO4Mass fraction is 85%.
Further, further include the refined of byproduct phosphoric acid potassium dihydrogen, the S1 iodomethane forming steps generate product iodine
Methane and potassium dihydrogen phosphate, distillation condensation and separation of iodomethane, remaining reaction product under agitation, in solution of potassium carbonate
With to pH value 8.5~9.0, neutralizer is filtered to remove insoluble matter after being concentrated into 120~124 DEG C, is subsequently cooled to 20 DEG C or less knots
Crystalline substance finally centrifuges, dry byproduct phosphoric acid potassium dihydrogen.
Further, in the S1 iodomethane forming steps, the phosphoric acid is fed by the way of being gradually added dropwise.
The disclosed new method that phenylene dimethyl ether is prepared using iodomethane of this programme, main producing including iodomethane, methyl
Change and distilation step, whole preparation process raw material and product low toxicity or nontoxic, reaction condition is mild, and security risk is small, and
And reaction yield is high, raw material potassium iodide can be recycled, while also prepare special high value using iodomethane forming steps
Byproduct greatly reduces production cost.
Specific implementation mode
To explain the technical content, the achieved purpose and the effect of the present invention in detail, it is explained in detail below in conjunction with embodiment.
Embodiment 1
A kind of preparation method of phenylene dimethyl ether, specific preparation process are as follows：
(1) in mass ratio 1:0.2, by raw material potassium iodide, reactor of the methanol input with part flow arrangement, is warming up to 90 DEG C.
Meanwhile 85% phosphoric acid of 1.2 times of weight of potassium iodide is gradually added dropwise, that is, phosphoric acid can be added in a dropping tank herein, and gradually by phosphorus
Acid, which is added dropwise in reaction system, to be reacted.So that potassium iodide, methanol and phosphoric acid fully react 3h, meanwhile, it is also utilized in reaction
Part flow arrangement separates product iodomethane from reaction system, until there is no distillates to distillate, reaction terminates, and right
Iodomethane distillate is washed, then is dried in vacuo, and the iodomethane that purity is 95% is finally obtained.Iodomethane, which can be used as, to methylate
Reagent and provide methyl for the synthesis of phenylene dimethyl ether.
(2) it is 1 according to mass ratio:2 hydroquinones, potassium hydroxide put into the reactor with part flow arrangement, while being added 1/2
The hexamethylene of volume ratio makees solvent, is warming up to 30 DEG C, and the iodomethane obtained in (1) is then added dropwise, carries out methylation reaction 5h,
It then proceedes to be warming up to 80~90 DEG C to react 1 hour, isolates the water that reaction system is generated using part flow arrangement, wait for water yield
Reaching theoretical water yield can stop reacting.The conversion ratio that phenylene dimethyl ether iodomethane is synthesized using the reaction is higher, and selectivity is good.
(3) the final bottom material of (2) methylation reaction is transferred to distilling apparatus, such as strips rectifying column, utilizes water vapour pair
Bottom material is distilled, and object clarification to be distillated obtains white clumpy solid, warp without coming to an end after material after distillate cooling
Filtration drying gets product phenylene dimethyl ether, can detect its freezing point temperature or other performance parameter.
(4) it will be filtered after surplus material evaporation and concentration in distilling apparatus in step (3), potassium iodide solid can be obtained, and
Obtained potassium iodide can be used as that step (1) iodomethane produces required raw material and circulating repetition uses.
(5) bottom is formed by potassium dihydrogen phosphate after being directed to step (1) reaction, can be molten with potassium carbonate under agitation
Liquid is neutralized to pH value 8.5, and then neutralizer is filtered to remove insoluble matter after being concentrated into 120 DEG C, be finally cooled to 20 DEG C of following crystallization,
Centrifugation, drying can obtain potassium dihydrogen phosphate.And by-product product dipotassium hydrogen phosphate can be used for medical industry, pH adjusting agent, water
Matter inorganic agent, in the phosphorating treatment of metal and be used as electroplating additive.During i.e. prepared by the phenylene dimethyl ether, obtained by corresponding
Byproduct phosphoric acid potassium dihydrogen also great economic value.
Whole preparation process raw material and product low toxicity or nontoxic, reaction condition is mild, and security risk is small, and reaction yield
Height, feedstock circulation use, can prepare the byproduct of special high value, greatly reduce production cost.
Embodiment 2
The present embodiment 2 and embodiment 1 difference lies in, the aliphatic methyl ether of methanol in former step (1) is replaced, so as to
It is used to prepare the intermediate of high value.
In mass ratio 1:0.6, by potassium iodide, reactor of the 3- methoxyl group -1- propionic acid input with part flow arrangement, is warming up to
100 DEG C, then 85% phosphoric acid with potassium iodide weight ratio in 1 ︰ 1.2 is added to by the way of being gradually added dropwise in reactor,
Reaction time 5h, until there is no distillates to distillate end, distillate washing, vacuum drying, it is 98% to obtain iodomethane purity, together
Shi Shuixiang distills out by-product 3- hydroxyl -1- propionic acid through negative pressure rectifying, i.e., during preparing target product phenylene dimethyl ether, also
It can be along with the by-product 3- hydroxyl -1- propionic acid for generating great economic value.Also, it can also be by replacing different aliphatic first
Ether obtains different midbody products.Increase economic benefit caused by this preparation process.
Embodiment 3
A kind of preparation method of phenylene dimethyl ether, specific preparation process are as follows：
(1) in mass ratio 1:0.3, by raw material potassium iodide, reactor of the methanol input with part flow arrangement, is warming up to 90 DEG C.
Meanwhile 85% phosphoric acid of 1.8 times of weight of potassium iodide is gradually added dropwise, that is, phosphoric acid can be added in a dropping tank herein, and gradually by phosphorus
Acid, which is added dropwise in reaction system, to be reacted.So that potassium iodide, methanol and phosphoric acid fully react 4h, meanwhile, it is also utilized in reaction
Part flow arrangement separates product iodomethane from reaction system, until there is no distillates to distillate, reaction terminates, and right
Iodomethane distillate is washed, then is dried in vacuo, and the iodomethane that purity is 96% is finally obtained.Iodomethane, which can be used as, to methylate
Reagent and provide methyl for the synthesis of phenylene dimethyl ether.
(2) it is 1 according to mass ratio:2 hydroquinones, potassium hydroxide put into the reactor with part flow arrangement, while being added 1/2
The hexamethylene of volume ratio makees solvent, is warming up to 30 DEG C, and the iodomethane obtained in (1) is then added dropwise, carries out methylation reaction 5h,
It then proceedes to be warming up to 80~90 DEG C to react 1 hour, isolates the water that reaction system is generated using part flow arrangement, wait for water yield
Reaching theoretical water yield can stop reacting.The conversion ratio that phenylene dimethyl ether iodomethane is synthesized using the reaction is higher, and selectivity is good.
(3) the final bottom material of (2) methylation reaction is transferred to distilling apparatus, such as strips rectifying column, utilizes water vapour pair
Bottom material is distilled, and object clarification to be distillated obtains white clumpy solid, warp without coming to an end after material after distillate cooling
Filtration drying gets product phenylene dimethyl ether, can detect its freezing point temperature or other performance parameter.
(4) it will be filtered after surplus material evaporation and concentration in distilling apparatus in step (3), potassium iodide solid can be obtained, and
Obtained potassium iodide can be used as that step (1) iodomethane produces required raw material and circulating repetition uses.
(5) bottom is formed by potassium dihydrogen phosphate after being directed to step (1) reaction, can be molten with potassium carbonate under agitation
Neutralize pH value 8.7, then neutralizer is filtered to remove insoluble matter after being concentrated into 122 DEG C, be finally cooled to 20 DEG C of following crystallization, from
Heart separation, drying can obtain potassium dihydrogen phosphate.And by-product product dipotassium hydrogen phosphate can be used for medical industry, pH adjusting agent, water quality
Inorganic agent, in the phosphorating treatment of metal and be used as electroplating additive.During i.e. prepared by the phenylene dimethyl ether, correspondence is obtained
Byproduct phosphoric acid potassium dihydrogen also great economic value.
Whole preparation process raw material and product low toxicity or nontoxic, reaction condition is mild, and security risk is small, and reaction yield
Height, feedstock circulation use, can prepare the byproduct of special high value, greatly reduce production cost.
Embodiment 4
The present embodiment 4 and embodiment 3 difference lies in, the aliphatic methyl ether of methanol in former step (1) is replaced, so as to
It is used to prepare the intermediate of high value.
In mass ratio 1.5:1, by potassium iodide, reactor of the 3- methoxyl group -1- propionic acid input with part flow arrangement, is warming up to
100 DEG C, then 85% phosphoric acid with potassium iodide weight ratio in 1 ︰ 2 is added to by the way of being gradually added dropwise in reactor, instead
6h between seasonable, until there is no distillates to distillate end, distillate washing, vacuum drying, it is 98% to obtain iodomethane purity, simultaneously
Water phase distills out by-product 3- hydroxyl -1- propionic acid through negative pressure rectifying and may be used also that is, during preparing target product phenylene dimethyl ether
Along with the by-product 3- hydroxyl -1- propionic acid for generating great economic value.Also, it can also be by replacing different aliphatic methyl ethers
To obtain different midbody products.Increase economic benefit caused by this preparation process.
Embodiment 5
A kind of preparation method of phenylene dimethyl ether, specific preparation process are as follows：
(1) in mass ratio 1:0.4, by raw material potassium iodide, reactor of the methanol input with part flow arrangement, is warming up to 90 DEG C.
Meanwhile 85% phosphoric acid of 2.4 times of weight of potassium iodide is gradually added dropwise, that is, phosphoric acid can be added in a dropping tank herein, and gradually by phosphorus
Acid, which is added dropwise in reaction system, to be reacted.So that potassium iodide, methanol and phosphoric acid fully react 5h, meanwhile, it is also utilized in reaction
Part flow arrangement separates product iodomethane from reaction system, until there is no distillates to distillate, reaction terminates, and right
Iodomethane distillate is washed, then is dried in vacuo, and the iodomethane that purity is 94% is finally obtained.Iodomethane, which can be used as, to methylate
Reagent and provide methyl for the synthesis of phenylene dimethyl ether.
(2) it is 2 according to mass ratio:Benzenediol, potassium hydroxide are put into the reactor with part flow arrangement, while using toluene by 1
Water entrainer is done for being azeotroped off the water for reacting generated, 85 DEG C are warming up to, then by the iodomethane obtained in (1) according to institute
Be added 5 times of weight of potassium iodide reaction system is added by the way of being gradually added dropwise so that benzenediol, potassium hydroxide and iodomethane in
First methylation reaction 8h in system then proceedes to be warming up to 103 DEG C and react 1 hour, reaction system is isolated using part flow arrangement
The water generated waits for that water yield reaches theoretical water yield and can stop reacting.Phenylene dimethyl ether iodomethane is synthesized using the reaction
Conversion ratio is higher, and selectivity is good.
(3) the final bottom material of (2) methylation reaction is transferred to distilling apparatus, such as strips rectifying column, utilizes water vapour pair
Bottom material is distilled, and object clarification to be distillated obtains white clumpy solid, warp without coming to an end after material after distillate cooling
Filtration drying gets product phenylene dimethyl ether, can detect its freezing point temperature or other performance parameter.
(4) it will be filtered after surplus material evaporation and concentration in distilling apparatus in step (3), potassium iodide solid can be obtained, and
Obtained potassium iodide can be used as that step (1) iodomethane produces required raw material and circulating repetition uses.
(5) bottom is formed by potassium dihydrogen phosphate after being directed to step (1) reaction, can be molten with potassium carbonate under agitation
Neutralize pH value 9.0, then neutralizer is filtered to remove insoluble matter after being concentrated into 124 DEG C, be finally cooled to 20 DEG C of following crystallization, from
Heart separation, drying can obtain potassium dihydrogen phosphate.And by-product product dipotassium hydrogen phosphate can be used for medical industry, pH adjusting agent, water quality
Inorganic agent, in the phosphorating treatment of metal and be used as electroplating additive.During i.e. prepared by the phenylene dimethyl ether, correspondence is obtained
Byproduct phosphoric acid potassium dihydrogen also great economic value.
Whole preparation process raw material and product low toxicity or nontoxic, reaction condition is mild, and security risk is small, and reaction yield
Height, feedstock circulation use, can prepare the byproduct of special high value, greatly reduce production cost.
Embodiment 6
The present embodiment 6 and embodiment 5 difference lies in, the aliphatic methyl ether of methanol in former step (1) is replaced, so as to
It is used to prepare the intermediate of high value.
In mass ratio 1.6:1, by potassium iodide, reactor of the 3- methoxyl group -1- propionic acid input with part flow arrangement, is warming up to
100 DEG C, then 85% phosphoric acid with potassium iodide weight ratio in 1 ︰ 2.4 is added to by the way of being gradually added dropwise in reactor,
Reaction time 8h, until there is no distillates to distillate end, distillate washing, vacuum drying, it is 97% to obtain iodomethane purity, together
Shi Shuixiang distills out by-product 3- hydroxyl -1- propionic acid through negative pressure rectifying, i.e., during preparing target product phenylene dimethyl ether, also
It can be along with the by-product 3- hydroxyl -1- propionic acid for generating great economic value.Also, it can also be by replacing different aliphatic first
Ether obtains different midbody products.Increase economic benefit caused by this preparation process.
Example the above is only the implementation of the present invention is not intended to limit the scope of the invention, every to utilize this hair
Equivalent process transformation made by bright specification is applied directly or indirectly in other relevant technical fields, and is similarly included in
In the scope of patent protection of the present invention.
Claims (10)
1. a kind of method preparing phenylene dimethyl ether using iodomethane, which is characterized in that include the following steps：
S1, iodomethane are produced, using potassium iodide, methanol/aliphatic methyl ether, tricresyl phosphate kind substance as raw material, reacted obtained iodine first
Alkane；
S2, methylate, using in benzenediol and S1 steps iodomethane and potassium hydroxide as raw material, occur methylation reaction formed
Include target product phenylene dimethyl ether and the mixed system of potassium iodide；
S3, distillation, methylating to S2 is formed by mixed system and distills, isolated single target product phenylene dimethyl ether
With the potassium iodide for being circularly used for S1 iodomethane and producing.
2. the method for preparing phenylene dimethyl ether using iodomethane as described in claim 1, it is characterised in that：The S2 methylates step
In rapid, raw materials used benzenediol, potassium hydroxide and iodomethane three's mass ratio are 1 ︰, 1.7~2 ︰ 4~5.
3. the method for preparing phenylene dimethyl ether using iodomethane as claimed in claim 2, it is characterised in that：The S2 methylates step
In rapid, reaction temperature is not higher than 30 DEG C, and reaction pressure is normal pressure.
4. the method for preparing phenylene dimethyl ether using iodomethane as claimed in claim 3, it is characterised in that：The S2 methylates step
In rapid, raw material iodomethane is fed by the way of being gradually added dropwise.
5. the method for preparing phenylene dimethyl ether using iodomethane as described in claim 1, it is characterised in that：The S3 distilation steps
In, mixed system is formed by S2 methylation reactions using steam and is distilled, until distillate is clarified without material, is evaporated
Go out object cooling, filters, is dry that white solid is target product phenylene dimethyl ether.
6. the method for preparing phenylene dimethyl ether using iodomethane as described in claim 1, it is characterised in that：The S1 iodomethane systems
It takes in step, using potassium iodide, aliphatic methyl ether and phosphoric acid as raw material, the mass ratio of three is 1 ︰, 0.6~1.6 ︰ 1.2~2.4,
In H contained by phosphoric acid used itself3PO4Mass fraction is 85%.
7. the method for preparing phenylene dimethyl ether using iodomethane as claimed in claim 6, it is characterised in that：The S1 iodomethane systems
It takes in step, aliphatic methyl ether is 3-MP or 3- methoxyl group -1- propionic acid.
8. the method for preparing phenylene dimethyl ether using iodomethane as described in claim 1, it is characterised in that：The S1 iodomethane systems
It takes in step, using potassium iodide, methanol and phosphoric acid as raw material, the mass ratio of three is 1 ︰, 0.2~0.4 ︰ 2~2.4, wherein phosphorus used
H contained by acid itself3PO4Mass fraction is 85%.
9. the method for preparing phenylene dimethyl ether using iodomethane as described in claim 1, it is characterised in that：Further include by-product phosphorus
Acid dihydride potassium it is refined, the S1 iodomethane forming steps generate product iodomethane and potassium dihydrogen phosphate, distillation condensation and separation of
Iodomethane, remaining reaction product under agitation, are neutralized with solution of potassium carbonate to pH value 8.5~9.0, neutralizer is concentrated into
It is filtered to remove insoluble matter after 120~124 DEG C, is subsequently cooled to 20 DEG C of following crystallization, is finally centrifuged, dry by-product phosphorus
Acid dihydride potassium.
10. the method for preparing phenylene dimethyl ether using iodomethane such as claim 6-9 any one of them, it is characterised in that：It is described
In S1 iodomethane forming steps, the phosphoric acid is fed by the way of being gradually added dropwise.
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| CN103011114A (en) * | 2012-12-28 | 2013-04-03 | 贵州金正大生态工程有限公司 | Method of producing monopotassium phosphate |
| CN107698423A (en) * | 2017-09-12 | 2018-02-16 | 沈阳化工大学 | A kind of method for preparing ethylene glycol and by-product halogenated alkane |
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2018
- 2018-05-30 CN CN201810536697.2A patent/CN108774116A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008096239A1 (en) * | 2007-02-07 | 2008-08-14 | Universita' Degli Studi Di Bari | Organic thin film transistors comprising thienyl oligomers and their use as gaseous phase sensors |
| CN103011114A (en) * | 2012-12-28 | 2013-04-03 | 贵州金正大生态工程有限公司 | Method of producing monopotassium phosphate |
| CN107698423A (en) * | 2017-09-12 | 2018-02-16 | 沈阳化工大学 | A kind of method for preparing ethylene glycol and by-product halogenated alkane |
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Application publication date: 20181109 |