CN104557478A - Method for preparing tert-butyl ether - Google Patents
Method for preparing tert-butyl ether Download PDFInfo
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- CN104557478A CN104557478A CN201310497033.7A CN201310497033A CN104557478A CN 104557478 A CN104557478 A CN 104557478A CN 201310497033 A CN201310497033 A CN 201310497033A CN 104557478 A CN104557478 A CN 104557478A
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- reaction
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- butylene
- ethylene glycol
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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
- C07C41/05—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
Abstract
The invention discloses a method for preparing tert-butyl ether, belongs to the field of organic chemical industry, and particularly relates to a method for preparing ethylene glycol tert-butyl ether in the presence of a catalyst. The method is characterized by comprising the following specific steps: mixing isobutylene containing 30-90% by mass of inert gas with ethylene glycol, introducing a mixture into a continuous distributed control reaction assembly for reaction, performing flash evaporation on a light component after the continuous reaction, and performing refinement and separation on a reaction product, wherein the continuous distributed control reaction assembly consists of three fixed bed reactors continuously connected in series, the fixed bed reactors are a reactor I (4), a reactor II (7) and a reactor III (11) respectively, different reaction conditions are required in the fixed bed reactors, and same or different solid catalysts are arranged in the fixed bed reactors. According to the method, ethylene glycol tert-butyl ether generated by mixing ethylene glycol with isobutylene according to a relatively low molar ratio is relatively high in selectivity which reaches more than 90%, and isobutylene is relatively high in conversion rate.
Description
Technical field
Produce a method for tertbutyl ether, genus organic chemical industry field, is specifically related to a kind of ethylene glycol and refinery C four is raw material, prepares the method for ethylene glycol tertbutyl ether under catalyzer existence condition.
Background technology
Ethylene glycol tertbutyl ether has many-sided advantages such as flash-point is high, nonflammable, toxicity is low, important industrial solvent and the intermediate of chemosynthesis, owing to containing ehter bond and hydroxyl in its molecule, with the performance of its excellence, be widely used as the industries such as Water-based surface coating, rocket engine fuel deicing agent, brake fluid, ink, dyestuff, medicine, spices and clean-out system, also can be used as the basal liquid of automobile industry synthesis brake fluid.
The method for making of gylcol ether has following methods usually:
1. ethylene glycol sodium and Organohalogen compounds reaction method: ethylene glycol sodium and tertiary butyl chloride react, generating glycol tertbutyl ether and sodium-chlor, this method, in reaction process, produces a large amount of solid product sodium-chlor, is restricted in process discharge process.
2. aliphatic epoxy compound and alcohols reaction method: oxyethane and the trimethyl carbinol carry out etherification reaction, obtains corresponding ethylene glycol tertbutyl ether and a small amount of diethylene glycol ethers and triglycol ether.This reaction in the absence of catalyst, is carried out at high temperature under high pressure, and adopt temperature to be generally 200 ~ 250 DEG C, pressure is 2.5 ~ 5 MPa.If in the presence of a catalyst, temperature of reaction and pressure reduce greatly.Industrial production is generally carried out in the presence of a catalyst, as at BF
3, A1C1
3, there is lower reaction in NaOH, temperature of reaction is 100 ~ 250 DEG C, pressure 0 ~ 4 MPa.This method is batch tank reaction, and pressure is higher, requires higher accordingly to equipment material.
3. ethylene glycol and the trimethyl carbinol are when mineral acid makees catalyzer, generating glycol ethers.The selectivity of this method to ethylene glycol mono-tert-butyl ether is poor, generates a part of water simultaneously, together with it is dissolved in catalyzer, defines part spent acid, adds a difficult problem for environmental protection treatment.
ethylene glycol and isobutene reaction method etc.
Chinese patent CN1065656A describes a kind of preparation method of diglycol monotertiary butyl ether, glycol ether and cracking C
4cut divinyl raffinate, as reaction raw materials, makees catalyzer with Macroporous strongly acid cation exchange resin, temperature 40 ~ 85 DEG C, and pressure 1.0 ~ 3.0 MPa, alfin mol ratio 1.0 ~ 3.0, liquid feeding air speed 0.5 ~ 3.0h
-1, under the condition that linear velocity is 180 ~ 350 lis ms/h, continue through fixed-bed reactor and carry out reaction generation diglycol monotertiary butyl ether, isobutene conversion 80 ~ 85%, the selectivity 90 ~ 97% of diglycol monotertiary butyl ether.Due to abundant raw material source, cheap, but it is lower significantly to reduce production cost isobutene conversion.
Chinese patent CN1230535A inscribes the synthesis technique that you bebeerilene rate ling relates to ethylene glycol mono-tert-butyl ether, this technique with ethylene glycol and iso-butylene for raw material, under the existence of strong acid cation exchange resin catalyst, in temperature 45 ~ 55 DEG C, react under pressure 0.8 ~ 2.0MPa condition, wherein reaction product component loops enters reactor feed, and internal circulating load is 55 ~ 65 % of total reactor inlet amount by weight percentage.Although this patent isobutene conversion is higher, the transformation efficiency of ethylene glycol is lower, and the selectivity of ethylene glycol mono-tert-butyl ether is poor.
In sum, prior art has the following disadvantages: (1) preparative separation complex process, seriously polluted; (3) still reaction is higher to pressure requirements, requires harsh accordingly to the material of equipment; (3) utilization ratio of ethylene glycol is lower; (4) selectivity of ethylene glycol mono-tert-butyl ether is poor.
Summary of the invention
The technical problem to be solved in the present invention is: overcome the deficiencies in the prior art, provides that a kind of ethylene glycol utilization ratio is high, ethylene glycol mono-tert-butyl ether selectivity is good, a kind of eco-friendly method of producing tertbutyl ether.
The technical solution adopted for the present invention to solve the technical problems is: the method for this production tertbutyl ether, it is characterized in that, concrete technology step is: be pass into continuous sub-control reaction component after the iso-butylene of 30% ~ 90% rare gas element mixes with ethylene glycol to react by being mixed with mass percentage content, continuous sub-control reaction component is three fixed-bed reactor of connecting continuously, be respectively a reactor, No. two reactors, No. three reactors, be respectively different reaction conditionss in three fixed-bed reactor and identical or different solid catalyst is housed, after successive reaction, flash distillation is carried out to light constituent, again refining spearation is carried out to reaction product,
Wherein, the operational condition of a reactor is: temperature of reaction 50 ~ 80 DEG C; Reaction pressure 1 ~ 3.0MPa; Alfin mol ratio (15 ~ 6): 1; Air speed 1.2 ~ 5.5h
-1;
The operational condition of No. two reactors is: temperature of reaction 45 ~ 65 DEG C; Reaction pressure 1 ~ 2.5MPa; Supplementary iso-butylene makes alfin mol ratio (10 ~ 2): 1; Air speed 0.9 ~ 4.5h
-1;
The operational condition of No. three reactors is: temperature of reaction 35 ~ 55 DEG C; Reaction pressure 1 ~ 2.0MPa; Supplementary iso-butylene makes alfin mol ratio (4 ~ 0.5): 1; Air speed 1.5 ~ 4h
-1.
Preferably, the operational condition of a described reactor is: temperature of reaction 55 ~ 70 DEG C; Reaction pressure 1.4 ~ 2MPa; Alfin mol ratio (10 ~ 7): 1; Air speed 1.0 ~ 2h
-1.
Preferably, the operational condition of No. two described reactors is: temperature of reaction 45 ~ 55 DEG C; Reaction pressure 1.2 ~ 1.7MPa; Alfin mol ratio (5 ~ 2): 1; Air speed 1.3 ~ 3.5h
-1.
Preferably, the operational condition of No. three described reactors is: temperature of reaction preferably 40 ~ 45 DEG C; Reaction pressure 1 ~ 1.5 MPa; Alfin mol ratio (3 ~ 1): 1; Air speed 1.8 ~ 3.5h
-1.
Described solid catalyst is solid super acid catalyst, resin catalyst, heteropolyacid catalyst or molecular sieve catalyst.The cation exchange resin catalyst of preferred sulfonic acid series macropore.
Described rare gas element is N
2, CO
2, methane, ethane, propane, Trimethylmethane, butane, 1-butylene, two or more arbitrary proportion mixture a kind of in 2-butylene and pentane.
The mass percent of described rare gas element in iso-butylene gas mixture is 55% ~ 85%.
Described continuous sub-control reaction component is specially: comprise a reactor of connecting successively, No. two reactors, No. three reactors, flashing tower, treating towers; A reactor head has ethylene glycol, isobutylene feed mouth, and a reactor and No. two reactors, No. two reactors and No. three reactors, No. three series pipe last times between reactor and flashing tower are parallel with the first voltage controlling component, the second voltage controlling component, the 3rd voltage controlling component; Series pipe after the first voltage controlling component, the second voltage controlling component has the first iso-butylene material-feeding port and the second iso-butylene material-feeding port.
Offering of iso-butylene material-feeding port, accurately can control material ratio in continuous cascade reaction, improves the transformation efficiency of raw material.
The present invention adopts solid catalyst, refinery C four and ethylene glycol are successively reacted by three fixed-bed reactor controlling different condition in proportion, by the selection of the mol ratio of the adjustment of the temperature of reactor and charging, the ethylene glycol of generation is made to have higher selectivity.
Compared with prior art, the beneficial effect that a kind of method of producing tertbutyl ether of the present invention has is: a kind of method of producing tertbutyl ether that the present invention relates to is different from existing halohydrocarbon permutoid reaction, still reaction, fixed bed reaction and other reaction process.The present invention adopts three fixed-bed reactor, by adjusting the temperature of three fixed-bed reactor and ethylene glycol and the mol ratio of iso-butylene in different reactor, can finally make ethylene glycol and iso-butylene under lower mol ratio, the ethylene glycol tertbutyl ether generated has higher selectivity, reach more than 90%, and iso-butylene has higher transformation efficiency, the transformation efficiency of iso-butylene reaches more than 92%.
Accompanying drawing explanation
Fig. 1 is generating glycol list tertiary butyl ether process schematic flow sheet.
Wherein: 1, ethylene glycol, isobutylene feed mouth 2, oil bath entrance 3, oil bath outlet 4, a reactor 5, first voltage controlling component 6, first iso-butylene material-feeding port 7, No. two reactors 8, second voltage controlling component 9, treating tower 10, second iso-butylene material-feeding port 11, No. three reactors 12, 3rd voltage controlling component 13, flashing tower 14, after reaction, carbon four exports 15, the tertiary butyl ether reaction mixture 16 of ethylene glycol, ethylene glycol mono-tert-butyl ether outlet 17, isolate exports.
Fig. 1 is a kind of most preferred embodiment producing the method for tertbutyl ether of the present invention, and below in conjunction with accompanying drawing 1, the present invention will be further described.
Embodiment
With reference to accompanying drawing 1: a kind of method equipment therefor producing tertbutyl ether of the present invention comprises a reactor 4, No. two reactors 7, No. three reactors 11, flashing tower 13, the treating towers 9 of connecting successively; Reactor 4 top has ethylene glycol, isobutylene feed mouth 1, reactor 4 and No. two reactors 7, No. two reactors 7 and the series pipe last time of No. 11, three, No. three reactors between reactor 11 and flashing tower 13 to be parallel with the first voltage controlling component 5, second voltage controlling component 8, the 3rd voltage controlling component 13; Series pipe after the first voltage controlling component 5, second voltage controlling component 8 has the first iso-butylene material-feeding port 6 and the second iso-butylene material-feeding port 10.All oil bath is set with outside a reactor 4, No. two reactors 7 and No. three reactors 11
Be described further a kind of method of producing tertbutyl ether of the present invention below in conjunction with specific embodiment, wherein embodiment 1 is most preferred embodiment.Wherein in each embodiment, control reaction pressure 1 ~ 3.0MPa in a reactor; Air speed 1.2 ~ 5.5h
-1; Reaction pressure 1 ~ 2.5MPa in No. two reactors; Air speed 0.9 ~ 4.5h
-1; Reaction pressure 1 ~ 2.0MPa in No. three reactors; Air speed 1.5 ~ 4h
-1.
Embodiment 1 ~ 8
The chemical pure ethylene glycol of 99% of metering and mixed c 4 (iso-butylene mass content 27.16%) are injected with ram pump respectively resin catalyst is housed, first fixed bed pre-reactor that temperature controls at 60 ~ 65 DEG C, then reaction product and the mixed c 4 metering infusion added are entered to be equipped with resin catalyst, second fixed-bed reactor that temperature controls at 45 ~ 50 DEG C, further reaction product and the mixed c 4 metering infusion added are entered to be equipped with resin catalyst, temperature control
Built in the 3rd fixed-bed reactor of 38 ~ 42 DEG C, the length 1500m of fixed-bed reactor, the internal diameter 8mm of reactor, the loadings butt 100ml of catalyzer, test-results sees the above table 1.
table 1 resin does the reaction result of catalyzer
Note: inlet amount refers to the inlet amount of ethylene glycol, unit is g/h.Mol ratio refers to the mol ratio of ethylene glycol and iso-butylene, and selectivity refers to the selectivity of ethylene glycol mono-tert-butyl ether, and transformation efficiency refers to the transformation efficiency of iso-butylene.Other caption is identical therewith.
Embodiment 9 ~ 12
Compare with embodiment 1 ~ 8, only change the content (57.95%) of iso-butylene in mixed c 4, the condition of fixed-bed reactor and other condition constant, test-results is in table 2.
the reaction result of table 2, the concentration of change iso-butylene in mixed c 4
。
Comparative example 13 ~ 18
Compare with embodiment 1 ~ 8, with fixed-bed reactor, other condition is constant, and test-results is in table 3.
table 3, resin do the reaction result of catalyzer at a reactor
。
Embodiment 18 ~ 20
The chemical pure ethylene glycol of 99% of metering and mixed c 4 (iso-butylene mass content 27%) are injected with ram pump respectively molecular sieve catalyst is housed, temperature controls at 60 ~ 65 DEG C, first fixed bed pre-reactor of reaction pressure 1.5MPa; Then reaction product and the mixed c 4 metering infusion added are entered to be equipped with molecular sieve catalyst, temperature controls at 45 ~ 50 DEG C, second fixed-bed reactor (alcohol iso-butylene mol ratio 3:1) of reaction pressure 1.5MPa; Again further reaction product and the mixed c 4 metering infusion added are entered to be equipped with molecular sieve catalyst, temperature controls at 38 ~ 42 DEG C, the 3rd fixed-bed reactor of reaction pressure 1.5MPa.The length 1500m of fixed-bed reactor, the internal diameter 8mm of reactor, the loadings butt 100ml of catalyzer, test-results is in table 4.
table 4, molecular sieve do the reaction result of catalyzer
Can find out that the selectivity of reactant under multiple reactor different treatment condition and transformation efficiency all improve a lot from embodiment and comparative example.Under single reactor condition, the selectivity of reactant and low conversion rate, waste raw material, and increase cost, quality product is low, needs more process to meet production requirement.
The above is only preferred embodiment of the present invention, and be not restriction the present invention being made to other form, any those skilled in the art may utilize the technology contents of above-mentioned announcement to be changed or be modified as the Equivalent embodiments of equivalent variations.But everyly do not depart from technical solution of the present invention content, any simple modification, equivalent variations and the remodeling done above embodiment according to technical spirit of the present invention, still belong to the protection domain of technical solution of the present invention.
Claims (8)
1. produce the method for tertbutyl ether for one kind, it is characterized in that, concrete technology step is: be pass into continuous sub-control reaction component after the iso-butylene of 30% ~ 90% rare gas element mixes with ethylene glycol to react by being mixed with mass percentage content, continuous sub-control reaction component is three fixed-bed reactor of connecting continuously, be respectively a reactor (4), No. two reactors (7), No. three reactors (11), be respectively different reaction conditionss in three fixed-bed reactor and identical or different solid catalyst is housed, after successive reaction, flash distillation is carried out to light constituent, again refining spearation is carried out to reaction product,
Wherein, the operational condition of a reactor (4) is: temperature of reaction 50 ~ 80 DEG C; Reaction pressure 1 ~ 3.0MPa; Alfin mol ratio (15 ~ 6): 1; Air speed 1.2 ~ 5.5h
-1;
The operational condition of No. two reactors (7) is: temperature of reaction 45 ~ 65 DEG C; Reaction pressure 1 ~ 2.5MPa; Supplementary iso-butylene makes alfin mol ratio (10 ~ 2): 1; Air speed 0.9 ~ 4.5h
-1;
The operational condition of No. three reactors (11) is: temperature of reaction 35 ~ 55 DEG C; Reaction pressure 1 ~ 2.0MPa; Supplementary iso-butylene makes alfin mol ratio (4 ~ 0.5): 1; Air speed 1.5 ~ 4h
-1.
2. a kind of method of producing tertbutyl ether according to claim 1, is characterized in that: the operational condition of a described reactor (4) is: temperature of reaction 55 ~ 70 DEG C; Reaction pressure 1.4 ~ 2MPa; Alfin mol ratio (10 ~ 7): 1; Air speed 1.0 ~ 2h
-1.
3. a kind of method of producing tertbutyl ether according to claim 1, is characterized in that: the operational condition of No. two described reactors (7) is: temperature of reaction 45 ~ 55 DEG C; Reaction pressure 1.2 ~ 1.7MPa; Alfin mol ratio (5 ~ 2): 1; Air speed 1.3 ~ 3.5h
-1.
4. a kind of method of producing tertbutyl ether according to claim 1, is characterized in that: the operational condition of No. three described reactors (11) is: temperature of reaction preferably 40 ~ 45 DEG C; Reaction pressure 1 ~ 1.5 MPa; Alfin mol ratio (3 ~ 1): 1; Air speed 1.8 ~ 3.5h
-1.
5. a kind of method of producing tertbutyl ether according to claim 1, is characterized in that: described solid catalyst is solid super acid catalyst, resin catalyst, heteropolyacid catalyst or molecular sieve catalyst.
6. a kind of method of producing tertbutyl ether according to claim 1, is characterized in that: described rare gas element is N
2, CO
2, methane, ethane, propane, Trimethylmethane, butane, 1-butylene, two or more arbitrary proportion mixture a kind of in 2-butylene and pentane.
7. a kind of method of producing tertbutyl ether according to claim 1, is characterized in that: the mass percent of described rare gas element in iso-butylene gas mixture is 55% ~ 85%.
8. a kind of method of producing tertbutyl ether according to claim 1, is characterized in that: described continuous sub-control reaction component is specially: comprise the reactor (4) connected successively, No. two reactors (7), No. three reactors (11), flashing tower (13), treating tower (9); Ethylene glycol, isobutylene feed mouth (1) are arranged at reactor (4) top, and a reactor (4) and No. two reactors (7), No. two reactors (7) and No. three reactors (11), series pipe last time between No. three reactors (11) and flashing tower (13) are parallel with the first voltage controlling component (5), the second voltage controlling component (8), the 3rd voltage controlling component (12); Series pipe after the first voltage controlling component (5), the second voltage controlling component (8) has the first iso-butylene material-feeding port (6) and the second iso-butylene material-feeding port (10).
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105061160A (en) * | 2015-07-22 | 2015-11-18 | 珠海飞扬新材料股份有限公司 | Diol tertiary butyl ether production method |
| CN106748668A (en) * | 2016-11-15 | 2017-05-31 | 潍坊康顺化工有限公司 | Ethylene glycol tertbutyl ether and its production technology |
| CN108002987A (en) * | 2016-10-28 | 2018-05-08 | 中国石油化工股份有限公司 | Two-step method prepares the method and system of glycerine alkyl ether |
| CN108083990A (en) * | 2016-11-21 | 2018-05-29 | 中国石油化工股份有限公司 | Two-step method prepares the method and system of glycerine alkyl ether |
| CN108503514A (en) * | 2018-03-09 | 2018-09-07 | 深圳市前海博扬研究院有限公司 | A kind of preparation method and applications of glycerine tertbutyl ether |
| CN110240950A (en) * | 2019-07-10 | 2019-09-17 | 深圳市前海博扬研究院有限公司 | Methanol gasoline additive, preparation method and the methanol gasoline containing the additive |
| CN113461495A (en) * | 2020-03-30 | 2021-10-01 | 中国石油化工股份有限公司 | Method for improving selectivity of ethylene glycol mono-tert-butyl ether and ethylene glycol mono-tert-butyl ether |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105061160A (en) * | 2015-07-22 | 2015-11-18 | 珠海飞扬新材料股份有限公司 | Diol tertiary butyl ether production method |
| CN108002987A (en) * | 2016-10-28 | 2018-05-08 | 中国石油化工股份有限公司 | Two-step method prepares the method and system of glycerine alkyl ether |
| CN106748668A (en) * | 2016-11-15 | 2017-05-31 | 潍坊康顺化工有限公司 | Ethylene glycol tertbutyl ether and its production technology |
| CN108083990A (en) * | 2016-11-21 | 2018-05-29 | 中国石油化工股份有限公司 | Two-step method prepares the method and system of glycerine alkyl ether |
| CN108083990B (en) * | 2016-11-21 | 2021-06-11 | 中国石油化工股份有限公司 | Method and system for preparing glycerin alkyl ether by two-step method |
| CN108503514A (en) * | 2018-03-09 | 2018-09-07 | 深圳市前海博扬研究院有限公司 | A kind of preparation method and applications of glycerine tertbutyl ether |
| CN110240950A (en) * | 2019-07-10 | 2019-09-17 | 深圳市前海博扬研究院有限公司 | Methanol gasoline additive, preparation method and the methanol gasoline containing the additive |
| CN113461495A (en) * | 2020-03-30 | 2021-10-01 | 中国石油化工股份有限公司 | Method for improving selectivity of ethylene glycol mono-tert-butyl ether and ethylene glycol mono-tert-butyl ether |
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Application publication date: 20150429 |