CN109651063A - The preparation method of iso-amylene - Google Patents
The preparation method of iso-amylene Download PDFInfo
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- CN109651063A CN109651063A CN201710935727.2A CN201710935727A CN109651063A CN 109651063 A CN109651063 A CN 109651063A CN 201710935727 A CN201710935727 A CN 201710935727A CN 109651063 A CN109651063 A CN 109651063A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/177—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by selective oligomerisation or polymerisation of at least one compound of the mixture
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/20—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only oxygen atoms as heteroatoms
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- 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
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
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- 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
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
- C07C41/42—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation by distillation
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C7/04—Purification; Separation; Use of additives by distillation
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- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/14—Phosphorus; Compounds thereof
- C07C2527/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- C07C2527/188—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum, tungsten or polonium
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Abstract
The present invention provides a kind of preparation methods of iso-amylene, are related to iso-amylene preparation technical field.The present invention carries out polymerization reaction by catalyst bed with liquid phase according to diolefin and the active difference of monoolefm polymerisations, by coarse isoamylene, makes the diolefin polymerization in coarse isoamylene, and the catalyst is storng-acid cation exchange resin, and mass space velocity is 1~20hr‑1, reaction temperature is 20~60 DEG C, and reaction pressure is 0.3~2.0MPa, to reduce the content for being etherified diolefin in preceding coarse isoamylene raw material, has then obtained the iso-amylene of high-purity by etherificate, rectifying, ether solution and rectifying.Through the invention, existing processing step is simplified, defect of the existing technology is effectively overcomed.
Description
Technical field
The present invention relates to iso-amylene preparation technical fields.
Background technique
Iso-amylene is a kind of important industrial chemicals, for producing pinacoline, and then produce efficient triazole bactericidal agent and
Plant growth regulator, herbicide etc. also serve as many fragrance, pesticide intermediate, it is also possible to make ultraviolet absorbing agent, photograph sense
Luminescent material and concrete dispersing agent etc..
The light dydrocarbon of C 5 fraction or naphtha pyrolysis ethylene by-product that iso-amylene is primarily present in catalytically cracked gasoline evaporates
In part, since, containing the compound very close there are many boiling point, iso-amylene is therefrom separated and is not easy in these light dydrocarbon materials.Mesh
The preceding separation method at most used is tert amyl methyl ether(TAME) cracking process, i.e., C 5 fraction is reacted with methanol generates methyl tert-amyl
Then ether is refining to obtain high-purity methyl tert-amyl ether, then Pintsch process obtains iso-amylene.
Since the diolefin contained in coarse isoamylene easily leads to the inactivation of catalyst for etherification, the prior art such as Chinese patent
CN201210363942.7 etc. is generallyd use plus the method for hydrogen, diene content in raw material is reduced, to improve catalyst for etherification
The cycle of operation.But the alkaline matter that contains of coarse isoamylene and Determination of Trace Sulfur easily lead to the inactivation of selective hydrogenation catalyst, because
This, which adds, the techniques such as washes it is usually necessary to use desulfurizing agent and Purified Water before hydrogen and pre-processes to raw material, is contained with reducing sulphur in raw material
Amount and removing alkaline matter.
In the prior art, selection hydrogenation process not only increases equipment investment, consumes selective hydrogenation catalyst and hydrogen,
And it inevitably increased the loss of coarse isoamylene, while washing repeatedly produces waste water in large quantities, increases at the three wastes
Reason expense.
Summary of the invention
It is an object of the invention to: overcome the deficiencies of the prior art and provide a kind of preparation method of iso-amylene.The present invention
The technical issues of solution is the process conditions for how selecting suitable catalyst and control suitable, will be micro double in coarse isoamylene
Alkene direct polymerization reduces the content of diolefin in coarse isoamylene raw material before being etherified, meets etherification procedure and want to the limitation of raw material
It asks.
The following are the specific technical solutions of the present invention:
A kind of preparation method of iso-amylene, the following steps are included:
1) coarse isoamylene carries out polymerization reaction by catalyst bed with liquid phase, make isoprene in coarse isoamylene,
The diolefin polymerizations such as pentadiene；The catalyst is storng-acid cation exchange resin, and mass space velocity is 1~20hr-1, reaction temperature
Degree is 20~60 DEG C, and reaction pressure is 0.3~2.0MPa；
2) reaction product iso-amylene and methanol are obtained on macropore sulfonic group cation exchange resin catalyst by step 1)
Etherification reaction is carried out, is generated tert amyl methyl ether(TAME) (TAME)；The mass exchange capacity of sulfonic group cation exchange resin be 3.0~
6.0mmol/g, mass space velocity are preferably 3~15hr-1, reaction temperature is preferably 30~70 DEG C, and reaction pressure is preferably 0.3~
1.2MPa；
3) using tert amyl methyl ether(TAME) and other impurities boiling point difference, by rectifying by tert amyl methyl ether(TAME) (TAME)
It is separated with other substances；Tower bottom of rectifying tower temperature is 100~160 DEG C, and tower top temperature is 40~90 DEG C, and reflux ratio is 3~7, tower
Kettle obtains the tert amyl methyl ether(TAME) (TAME) that purity is 98% or more；
4) tert amyl methyl ether(TAME) for obtaining step 3) is anti-by carrying out ether solution equipped with heteropolyacid catalyst bed with gas phase
It answers, tert amyl methyl ether(TAME) is decomposed into iso-amylene and methanol；The mass exchange capacity of catalyst is 3.0~6.0mmol/g, and quality is empty
Speed is 0.5~2.0hr-1, reaction pressure is 0.3~1.5MPa, and reaction temperature is 150~280 DEG C；
5) iso-amylene obtained by step 4) can further progress rectifying, tower bottom of rectifying tower temperature is 70~85 DEG C, tower top
Temperature is 28~35 DEG C, and reflux ratio is 2~10；Tower reactor methanol removal and heavy constituent impurity, tower top obtain iso-amylene product.
Abovementioned steps 1) catalyst, preferably macropore sulfonic group cation exchange resin.
Abovementioned steps 2) described in amount air speed be preferably 5~10hr-1, reaction temperature is preferably 40~50 DEG C, reaction pressure
Preferably 0.5~1.0MPa.
Abovementioned steps 3) bottom temperature is preferably 120~140 DEG C, and tower top temperature is preferably 50~75 DEG C, reflux ratio
Preferably 4~6.
Abovementioned steps 4) described in reaction temperature be preferably 180~230 DEG C, the mass exchange capacity of the heteropoly acid is excellent
It is selected as 4~5.5mmol/g, mass space velocity is preferably 1.0~1.5hr-1, reaction pressure is preferably 0.5~1.0MPa.
Abovementioned steps 5) bottom temperature is preferably 75~80 DEG C, and tower top temperature is preferably 30~32 DEG C, and reflux ratio is excellent
It is selected as 3~5.
The present invention has obtained the iso-amylene of high-purity by micro diolefin polymerization, etherificate, rectifying, ether solution and rectifying,
Key is the process conditions for selecting suitable catalyst and control suitable before coarse isoamylene is reacted with methanol etherification, will be thick different
Micro diolefin direct polymerization in amylene reduces the content of diolefin in coarse isoamylene raw material.
Inventor is found through experiments that, according to diolefin and the active difference of monoolefm polymerisations, the sulphur of bulky grain can be selected
Acidic group cation exchange resin controls suitable process conditions, by the micro diolefin direct polymerization in coarse isoamylene, to meet
Limitation requirement of the etherification procedure to raw material.
The present invention is due to using the technology described above, compared with prior art, other without introducing into reaction system
Substance does not increase additional burden to the purifying of product or purification, and only by the control to polymerization reaction, make etherification reaction
The content of preceding diolefin can be down to 0.3% hereinafter, simplify existing processing step, effectively overcome of the existing technology
Defect.
Detailed description of the invention
Fig. 1 is the preparation method process flow chart of iso-amylene provided in an embodiment of the present invention.
Description of symbols:
Polymer reactor 100, methyltertiarvbutyl ether reactor 200, first rectifying column 300, ether solution reactor 400, Second distillation column
500。
Specific embodiment
Make further specifically below in conjunction with preparation method of the drawings and specific embodiments to iso-amylene provided by the invention
It is bright.It should be noted that the combination of technical characteristic described in following embodiments or technical characteristic is not construed as orphan
Vertical, they can be combined with each other to reach superior technique effect.
It should be noted that structure, ratio, size etc. depicted in this specification institute attached drawing, only to cooperate explanation
The revealed content of book is not limited to invent enforceable restriction item so that those skilled in the art understands and reads
Part, the modification of any structure, the change of proportionate relationship or the adjustment of size are not influencing the effect of invention can be generated and institute's energy
Under the purpose reached, it should all fall in the range of the revealed technology contents of invention can cover.
Technology, method and apparatus known to person of ordinary skill in the relevant may be not discussed in detail, but suitable
In the case of, the technology, method and apparatus should be considered as authorizing part of specification.Institute that is shown here and discussing
Have in example, any occurrence should be construed as merely illustratively, not as limitation.Therefore, exemplary embodiment
Other examples can have different values.
Embodiment
The process flow of embodiment is shown in Figure 1, has obtained height by following technical process using coarse isoamylene as raw material
The iso-amylene product of purity:
Step 1), coarse isoamylene in iso-amylene head tank is with liquid phase by being provided with the polymer reactor of catalyst bed
100, polymerization reaction is carried out in polymer reactor 100, keeps the diolefins such as isoprene, the pentadiene in coarse isoamylene poly-
It closes, the catalyst is macropore sulfonic group cation exchange resin.
Mass space velocity in polymer reactor is 1~20hr-1, corresponding reaction temperature is 20~60 DEG C, corresponding reaction
Pressure is 0.3~2.0MPa.
By the aforementioned control to diolefin polymerization reaction condition, the content of diolefin before etherification reaction can be made to be down to
0.3% or less.
Step 2) obtains reaction product material W1 by step 1), and the iso-amylene and methanol in material W1 are being provided with macropore
Etherification reaction occurs in the methyltertiarvbutyl ether reactor 200 of sulfonic group cation exchange resin catalyst, generates product material W2, material W2
Main component be tert amyl methyl ether(TAME) (TAME).
The mass exchange capacity of sulfonic group cation exchange resin can be 3.0~6.0mmol/g, preferably 4~
5.5mmol/g；Mass space velocity can be 3~15hr-1, preferably 5~10hr-1；Reaction temperature can be 30~70 DEG C, preferably
It is 40~50 DEG C；Reaction pressure can be 0.3~1.2MPa, preferably 0.5~1.0MPa.
Step 3), for the material W2 that step 2) obtains, using the difference of tert amyl methyl ether(TAME) and the boiling point of other impurities,
By material W2 by first rectifying column 300, tert amyl methyl ether(TAME) (TAME) and other substances are separated by rectifying.Tower reactor obtains
Material W3, material W3 are the tert amyl methyl ether(TAME) (TAME) of 98% or more purity.
The bottom temperature of first rectifying column 300 can be 100~160 DEG C, preferably 120~140 DEG C；Tower top temperature can be with
It is 40~90 DEG C, preferably 50~75 DEG C；Reflux ratio can be 3~7, preferably 4~6.
Step 4), the tert amyl methyl ether(TAME) that step 3) is obtained pass through the ether solution equipped with heteropolyacid catalyst bed with gas phase
The reaction of ether solution occurs for reactor 400, gas phase tert amyl methyl ether(TAME), and tert amyl methyl ether(TAME) is decomposed into iso-amylene and methanol, is produced
Object material W4.
The mass exchange capacity of catalyst can be 3.0~6.0mmol/g, preferably 4~5.5mmol/g；Mass space velocity
It can be 0.5~2.0hr-1, preferably 1.0~1.5hr-1；Reaction pressure can be 0.3~1.5MPa, preferably 0.5~
1.0MPa；Reaction temperature can be 150~280 DEG C, preferably 180~230 DEG C.
Step 5), by the material W4 of step 4) by Second distillation column 500, to iso-amylene further progress rectifying；Tower reactor
Methanol removal and heavy constituent impurity, tower top obtain material W5, are high-purity iso-amylene product.
The bottom temperature of Second distillation column 500 can be 70~85 DEG C, preferably 75~80 DEG C；Tower top temperature can be 28
~35 DEG C, preferably 30~32 DEG C；Reflux ratio can be 2~10, preferably 3~5.
Height has been obtained by micro diolefin polymerization, etherificate, rectifying, ether solution and rectification step by above-mentioned process flow
The iso-amylene product of purity.The iso-amylene product can satisfy the requirement of enterprise's production pinacoline (front three benzylacetone).
Claims (10)
1. a kind of preparation method of iso-amylene, it is characterised in that the following steps are included:
1) coarse isoamylene carries out polymerization reaction by catalyst bed with liquid phase, makes the diolefin polymerization in coarse isoamylene；It is described
Catalyst is storng-acid cation exchange resin, and mass space velocity is 1~20hr-1, reaction temperature is 20~60 DEG C, and reaction pressure is
0.3~2.0MPa；
2) reaction product iso-amylene and methanol is obtained on macropore sulfonic group cation exchange resin catalyst by step 1) to carry out
Etherification reaction generates tert amyl methyl ether(TAME)；
3) using tert amyl methyl ether(TAME) and other impurities boiling point difference, by rectifying by tert amyl methyl ether(TAME) and other impurities
Separation, tower reactor obtain the tert amyl methyl ether(TAME) that purity is 98% or more；
4) tert amyl methyl ether(TAME) for obtaining step 3) is with gas phase by carrying out the reaction of ether solution, first equipped with heteropolyacid catalyst bed
Base tert-amyl ether is decomposed into iso-amylene and methanol；
5) rectifying, tower reactor methanol removal and heavy constituent impurity are carried out to the iso-amylene that step 4) obtains, tower top obtains iso-amylene and produces
Product.
2. according to the method described in claim 1, it is characterized by: the catalyst is macropore sulfonic group cation exchange tree
Rouge.
3. according to the method described in claim 1, it is characterized by: abovementioned steps 2) in, sulfonic group cation exchange resin
Mass exchange capacity is 3.0~6.0mmol/g, and mass space velocity is 3~15hr-1, reaction temperature is 30~70 DEG C, and reaction pressure is
0.3~1.2MPa.
4. according to the method described in claim 3, it is characterized by: the mass space velocity is 5~10hr-1；Reaction temperature is
40~50 DEG C；Reaction pressure is 0.5~1.0MPa.
5. according to the method described in claim 1, it is characterized by: abovementioned steps 3) in, the bottom temperature of rectifying column is 100~
160 DEG C, tower top temperature is 40~90 DEG C, and reflux ratio is 3~7.
6. according to the method described in claim 5, tower top temperature is it is characterized by: the bottom temperature is 120~140 DEG C
50~75 DEG C, reflux ratio is 4~6.
7. according to the method described in claim 1, it is characterized by: abovementioned steps 4) in, the mass exchange capacity of catalyst is
3.0~6.0mmol/g, mass space velocity are 0.5~2.0hr-1, reaction pressure is 0.3~1.5MPa, and reaction temperature is 150~280
℃。
8. according to the method described in claim 7, it is characterized by: the mass exchange capacity is 4~5.5mmol/g, quality
Air speed is 1.0~1.5hr-1, reaction pressure is 0.5~1.0MPa, and reaction temperature is 180~230 DEG C.
9. according to the method described in claim 1, it is characterized by: abovementioned steps 5) in, the bottom temperature of rectifying column is 70~
85 DEG C, tower top temperature is 28~35 DEG C, and reflux ratio is 2~10.
10. according to the method described in claim 9, it is characterized by: the bottom temperature be 75~80 DEG C, tower top temperature 30
~32 DEG C, reflux ratio is 3~5.
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2398930A (en) * | 1943-01-23 | 1946-04-23 | Filtrol Corp | Process for separating monomeric diolefins from mixtures of relatively low boiling diolefin and mono-olefin monomers |
| US5300126A (en) * | 1992-10-19 | 1994-04-05 | Mobil Oil Corporation | Process for improving olefin etherification catalyst life |
| CN1117959A (en) * | 1994-08-30 | 1996-03-06 | 中国石化齐鲁石油化工公司 | Etherification reaction process and equipment for light hydrocarbon and fatty alcohol |
| CN1209077A (en) * | 1996-02-12 | 1999-02-24 | 化学研究及许可证公司 | Etherification-hydrogenation process |
| CN102040452A (en) * | 2009-10-26 | 2011-05-04 | 中国石油化工股份有限公司 | Method for preparing isoamylene by using tertiary amyl methyl ether |
| CN103664458A (en) * | 2012-09-25 | 2014-03-26 | 中国石油化工股份有限公司 | Selective hydrogenation method of crude isopentene |
| CN106588550A (en) * | 2015-10-14 | 2017-04-26 | 中国石油化工股份有限公司 | Method for improving content of 2-methyl-2-butylene |
-
2017
- 2017-10-10 CN CN201710935727.2A patent/CN109651063A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2398930A (en) * | 1943-01-23 | 1946-04-23 | Filtrol Corp | Process for separating monomeric diolefins from mixtures of relatively low boiling diolefin and mono-olefin monomers |
| US5300126A (en) * | 1992-10-19 | 1994-04-05 | Mobil Oil Corporation | Process for improving olefin etherification catalyst life |
| CN1117959A (en) * | 1994-08-30 | 1996-03-06 | 中国石化齐鲁石油化工公司 | Etherification reaction process and equipment for light hydrocarbon and fatty alcohol |
| CN1209077A (en) * | 1996-02-12 | 1999-02-24 | 化学研究及许可证公司 | Etherification-hydrogenation process |
| CN102040452A (en) * | 2009-10-26 | 2011-05-04 | 中国石油化工股份有限公司 | Method for preparing isoamylene by using tertiary amyl methyl ether |
| CN103664458A (en) * | 2012-09-25 | 2014-03-26 | 中国石油化工股份有限公司 | Selective hydrogenation method of crude isopentene |
| CN106588550A (en) * | 2015-10-14 | 2017-04-26 | 中国石油化工股份有限公司 | Method for improving content of 2-methyl-2-butylene |
Non-Patent Citations (2)
| Title |
|---|
| 徐泽辉: "异丁烯、异戊烯及其下游产品制备工艺的研究", 《中国博士学位论文全文数据库 工程科技Ⅰ辑》 * |
| 杨忠保等: "异戊烯的生产", 《石油化工》 * |
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