CN100391920C - Method for producing substituted benzyl alcohol by continuous process and its apparatus - Google Patents
Method for producing substituted benzyl alcohol by continuous process and its apparatus Download PDFInfo
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- CN100391920C CN100391920C CNB2005100406139A CN200510040613A CN100391920C CN 100391920 C CN100391920 C CN 100391920C CN B2005100406139 A CNB2005100406139 A CN B2005100406139A CN 200510040613 A CN200510040613 A CN 200510040613A CN 100391920 C CN100391920 C CN 100391920C
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Abstract
The present invention discloses a method and a device for continuously producing substituted benzyl alcohol. In the method, substituted benzyl halide is mixed with water, and mixtures and water vapor parallelly pass through a trickle-bed reactor for continuous hydrolyzation and separation to produce the substituted benzyl alcohol. The device is the trickle-bed reactor which comprises a mixer, a reactor, a condenser, a heat exchanger, an extracting reactor, an evaporator and a rectifying tower. The method has the advantages of low cost, high product quality, environmental protection, continuous production, etc.; the device has the advantages of simple structure and convenient operation.
Description
Technical field
The present invention relates to the production method of substituted benzyl alcohol, particularly relate to a kind of method of producing substituted benzyl alcohol by continuous process, the invention still further relates to the device of this method of employing.
Background technology
Substituted benzyl alcohol is used as intermediate, the medicated premix of multi-usage solvent, Minute Organic Synthesis and is used to prepare the compound with pharmaceutical active and agricultural chemical activity, is well known to a person skilled in the art.For example halogeno-benzyl alcohol is as the synthetic intermediate of pyrethroid.
Benzyl halide hydrolysis reaction under the alkali effect prepares benzyl alcohol, extensively is seen in disclosed document, as Kirk-OthmerEncyclopedia of Chemical Technology, 5th ed., Jonh Weily ﹠amp; Sons, Inc., New York, 2001.Vol.6, pp.323～334.The processing method of being produced benzyl alcohol by benzyl chloride mainly contains two classes, and a class is a direct method, and the benzyl halide direct hydrolysis obtains benzyl alcohol; Another kind of is indirect method, and benzyl halide is converted into benzyl ester earlier, and hydrolysis or alcoholysis benzyl ester obtain benzyl alcohol again.Direct method such as US4474993 disclose the continuous processing method of benzyl chloride basic hydrolysis, and US5670029, US5728897 and US5750801 disclose separating and the continuous processing method of the alkali-free of hydrolysis benzyl chloride, solvent-free technology, reaction mixture.Indirect method such as US4283565 disclose the first system of benzyl halide manthanoate, afterwards alcohol solves the technology of benzyl alcohol.Can obtain multiple benzyl ester easily from other technology approach, the ester hydrolysis can obtain the high purity benzyl alcohol, as the disclosed method of US5883290, US6057482, US6326521B2 and US20010014762.Such benzyl ester hydrolysis process has superiority in all many-sides than indirect method.Therefore, direct method is worth further research and development.As a large amount of alkali of the continuous basic hydrolysis arts demand of the benzyl chloride of US4474993 consumption, produce salt and waste water.As US5670029, US5728897 and the disclosed benzyl chloride hydrolysis process of US5750801, its remarkable advantage is a single step reaction, and is solvent-free, alkali-free, and yield height, benzyl chloride recycle and reclaim hydrogenchloride.Obviously, because the structure diversity of substituted benzyl halogen and the extensive use of corresponding substituted benzyl alcohol thereof, hope can realize being produced by substituted benzyl halogen direct, the easy and eco-friendly processing method of substituted benzyl alcohol.
Summary of the invention
The purpose of this invention is to provide a kind of continuous processing and produce the method for substituted benzyl alcohol by the benzyl halide direct hydrolysis.
The objective of the invention is to realize by following measures:
A kind of method of continuous production substituted benzyl alcohol, this method is mixed substituted benzyl halogen with water, mixture and water vapor are parallel by trickle-bed reactor, continuous hydrolysis with separate, produce substituted benzyl alcohol;
Wherein, substituted benzyl halogen is suc as formula shown in (I), and substituted benzyl alcohol is suc as formula shown in (II):
Here, k represents an integer of 1～2, l represents an integer of 0～5, m represents an integer of 0～5, n represents an integer of 0～4, (k+l+m+n) be an integer of 2～6, the substituting group that R represents is bromine, trifluoromethyl, itrile group, nitro, amide group, alkoxyl group or aryloxy, and X represents Cl, Br or I.
Described method, wherein substituted benzyl halogen is suc as formula shown in (III), and substituted benzyl alcohol is suc as formula shown in (IV):
Here, k, l, m, X are identical with above-mentioned definition.
Described method, wherein substituted benzyl halogen is shown in formula V, and substituted benzyl alcohol is suc as formula shown in (VI):
Here, k, l, n, R, X are identical with above-mentioned definition.
Described method, wherein substituted benzyl halogen is suc as formula shown in (VII), and substituted benzyl alcohol is suc as formula shown in (VIII):
Here, k, l, identical with above-mentioned definition.
Described method, wherein substituted benzyl halogen is suc as formula shown in (IX), and substituted benzyl alcohol is suc as formula shown in (X):
Here, l, X are identical with the definition in the claim 1; Further, l is 1,2 or 3, and X is a chlorine.
Hydrolytic process does not have other material to make solvent, do not use in alkali neutralization or the part and acidic by-products, do not add catalyzer, reaction mixture mainly is substituted benzyl alcohol, hydrogen halide, a small amount of dibenzyl ether and unconverted raw material, the mixture phase-splitting of reaction, organic phase mainly is a substituted benzyl alcohol, water mainly is a haloid acid, purified product reclaims haloid acid.
Substituted benzyl halogen of the present invention (I) raw material can obtain Industrial products.
Temperature of reaction is controlled at 40～220 ℃, is preferably 80～180 ℃, is preferably 120～150 ℃ especially; The reaction pressure scope is 0～5 MPa, is preferably 0～3 MPa, is preferably 0～1 MPa especially; The water yield is 1～40 times of substituted benzyl halogen amount by volume, is preferably 1～15 times, is preferably 1～5 times especially.
The reaction process characteristics are:
(1) the parallel trickle-bed reactor that passes through of raw material substituted benzyl halogen and water vapor;
(2) filler in the trickle-bed reactor is an inert fill material;
(3) the hydrolysis reaction product is by extracting and separating water and organic phase, and water is to contain the haloid acid aqueous solution, and organic phase is to contain substituted benzyl halogen, substituted benzyl alcohol, disubstituted benzyl ether mixed solution;
(4) organic phase can obtain thick substituted benzyl alcohol by underpressure distillation;
(5) thick substituted benzyl alcohol is through one-level rectifying, can obtain unreacting material substituted benzyl halogen, the pure and mild impurity disubstituted benzyl of substituted benzyl ether simultaneously, recyclable the re-using of raw material substituted benzyl halogen, the aqueous solution that contains the haloid acid of lower concentration further concentrates the aqueous solution that can obtain dense haloid acid.
The extraction agent that adopts is the organic solvent of 1-9 carbon, and these organic solvents are benzene, toluene, ethylbenzene, dimethylbenzene, methylene dichloride, chloroform, ethylene dichloride, trichloroethane.
The device of utilization aforesaid method is a trickle-bed reactor, comprises mixing tank, reactor, condenser, interchanger, extraction reactor, vaporizer and rectifying tower.
Wherein, mixing tank, reactor, condenser, interchanger, extraction reactor, the order of connection of vaporizer and rectifying tower is: mixer outlet links to each other with reactor one end entrance, reactor outlet links to each other with condenser inlet, condensator outlet links to each other with the extraction reactor inlet, extraction reactor one brings out mouth and links to each other with evaporator inlet, the other end outlet is used to discharge isolating water, vaporizer one brings out mouth and links to each other with the rectifying tower inlet, the other end outlet is used to discharge isolating extraction agent, the rectifying tower outlet is divided into the top, the middle part, outlet at bottom, interchanger connects condenser and mixing tank.
With reference to Figure of description reaction process of the present invention is described in detail:
Raw material substituted benzyl halogen 1 and water after the Hybrid Heating to 80 ℃, are added from reactor R top inlet by pump in mixing tank M continuously, and the two volume ratio scope preferably 1～15, is preferably in 1～5 1～40.Reactor temperature is controlled at 40～220 ℃, preferred 80-180 ℃, is preferably in 120-150 ℃.Reactor R is the tubular type isothermal reactor, the inner inert filler (as Raschig ring, granulated glass sphere etc.) of filling.Reactor R aspect ratio is 1: 2-1: 9, be preferably 1: 2-1: and 4, pressure-controlling is at 0.1-0.5MPa (slightly pressure).Raw material substituted benzyl halogen 1 evenly is sprayed on the filler by the sparger at reactor R top, feeds water vapor 2 from another inlet of reactor head simultaneously, passes through reactor with substituted benzyl halogen 1 and stream.Raw material substituted benzyl halogen 1 distributes on the inert filler in reactor in liquid mode, forms the form of trickle bed, has increased mass transfer area, has improved mass-transfer efficiency; Raw water steam 2 contacts with substituted benzyl halogen 1 with gaseous state, finishes hydrolysis reaction.The air speed of raw material substituted benzyl halogen 1 is 0.1-0.5h
-1, be preferably in 0.2-0.3h
-1, the air speed of water vapor 2 is 0.2-1.0h
-1, be preferably in 0.4-0.8h
-1
After coming out from reactor R, reaction mixture 3 enters condenser L, and refrigerative reaction mixture 4 enters extraction reactor E.In extraction reactor E, the organic solvent (as benzene, toluene, ethylbenzene, vinylbenzene, methylene dichloride, chloroform, ethylene dichloride, trichloroethane etc.) that adds 1-9 carbon extracts as extraction agent 11.After continuous extraction, bring out mouthful isolating water 9 of recovery from one; Organic phase 5 enters vaporizer V from another outlet, and holding temperature steams extraction agent 11 between 90-100 ℃, brings out a mouthful recovery through one and uses.The crude product 6 (including the substituted benzyl alcohol of 85-90%, the raw material substituted benzyl halogen of 0.1-5%, the by product of 0.5-6%, as two ethers) of bottom, evaporation back oily liquids enters into rectifying tower D through another outlet.In order to reduce heat energy consumption, can the heat transferred mixing tank M of condenser L be heated raw material by heat exchanger T.
In rectifying tower D, control pressure is at 1.20-1.40kPa, preferred 1.33kPa, the raw material substituted benzyl halogen 8 of top discharge for reclaiming, in the middle part temperature is 110-120 ℃, and overhead product is the substituted benzyl alcohol 10 of purity＞99.99%, and the bottom is high boiling impurity two ethers 7.Bottom temp is controlled at 100-200 ℃, preferably is controlled at 150-200 ℃.The operate continuously flow control is at 0.15-0.9kgh
-1, be preferably in 0.3-0.7kgh
-1
After the water 9 (containing haloid acid) that comes out enters concentration tank and concentrates, can obtain dense haloid acid from extraction reactor.In order further to guarantee the safety of emission gases, can pass through an absorption tower again, with remaining acid gas absorption, obtain rare haloid acid, after further concentrating, reclaim again, the water that concentrates out turns back to steam oven and reuses.
Beneficial effect of the present invention:
Preparing the benzyl alcohol method continuously with the benzyl chloride of US5750801 compares, present method has improved the mass transfer of reaction by trickle-bed reactor, make one step of reaction transformation efficiency reach more than 70～80%, the highlyest can reach 95%, reduced the difficulty of later separation, continuous rectification can change one-level into, product purity＞99.99% by three grades.
The distinguishing feature of method of the present invention is to adopt successive reaction and separating technology, do not use alkaline matter, reduced resource consumption and waste discharge, the haloid acid of generation is through separating and concentrating, renewable use has embodied Atom economy and eco-friendly process characteristic.
The advantage that adopts the reaction of gas and liquid flowing trickle bed be the gas-liquid flow pattern near plug flow, back-mixing is little, just can reach high conversion in single reactor; The liquid film on inert support surface is very thin, and the resistance to mass transfer that gas phase vapor transmission liquid film is diffused into catalyst surface is little; Simultaneously, adopt and flow to operation down, the possibility of no liquid flooding, the vapor phase stream dynamic resistance is little, and the vapor-phase reactant dividing potential drop is even in whole reactor, can reduce the energy consumption of gas delivery.
The substituted benzyl alcohol of multiple structure can be used as intermediate, the medicated premix of multi-usage solvent, Minute Organic Synthesis and is used to prepare compound with pharmaceutical active and agricultural chemical activity etc.
Description of drawings
Fig. 1 is that the present invention prepares the substituted benzyl alcohol schema continuously.
Wherein 1 represents raw material substituted benzyl halogen, 2 expression water vapors, 3 expression reaction mixtures, 4 expression refrigerative reaction mixtures, 5 expression organic phases, 6 expression crude products, by products such as 7 expression disubstituted benzyl ethers, the substituted benzyl halogen that 8 expressions are reclaimed, 9 expression waters (including haloid acid), 10 expression product substituted benzyl alcohols, 11 expression extraction agents.
M represents mixing tank, and R represents reactor, and L represents condenser, and T represents interchanger, and E represents extraction reactor, and V represents vaporizer, and D represents rectifying tower.
Embodiment
The invention will be further elaborated below in conjunction with Figure of description, so that understand the present invention better.Yet, those skilled in the art will readily understand that the described concrete material proportion of embodiment, processing condition and result thereof only are used to illustrate the present invention, and should also can not limit the present invention described in detail in claims.
General tubular trickle bed reactor design can be with reference to " Perry chemical engineering handbook (Perry ' s ChemicalEngineerings Handbook, McGraw Hill N.Y., 6th Ed.1984), Continuous Heat exchange and the design of continuous extraction process are with reference to " Liv Ullmann chemical industry complete works, unit operation " (Ullmann ' s Encyclopedia of Ing.Chem.UnitOperations II Vol.B3 pp6-31).
Embodiment 1:
Raw material substituted benzyl chlorine 1 and water after the Hybrid Heating to 80 ℃, are added from reactor R top by pump in mixing tank M continuously, and the volume ratio of substituted benzyl halogen and water is 1: 15.Reactor temperature is controlled at 120-150 ℃.Reactor R is the tubular type isothermal reactor, the inner inert filler (as granulated glass sphere) of filling.The reactor aspect ratio is 1: 3, and pressure-controlling is at 0.4MPa.Raw material substituted benzyl chlorine 1 sparger by reactor R top (being used for material is evenly distributed on filler) evenly is sprayed at filler, feeds water vapor 2 from reactor head simultaneously, passes through reactor with substituted benzyl chlorine 1 and stream.Raw material substituted benzyl chlorine 1 distributes on the inert filler in reactor in liquid mode, forms the form of trickle bed, has increased mass transfer area, has improved mass-transfer efficiency; Raw water steam 2 contacts with substituted benzyl halogen 1 with gaseous state, finishes hydrolysis reaction.The air speed of raw material substituted benzyl chlorine 1 (chemical industry Essential Terms) is 0.3h
-1, the air speed of water vapor 2 is 0.8h
-1
After coming out from reactor R, reaction mixture 3 enters condenser L, and refrigerative reaction mixture 4 enters extraction reactor E.In extraction reactor E, add toluene and extract as extraction agent 11.After continuous extraction, reclaim water 9; Organic phase 5 enters vaporizer V, and holding temperature steams extraction agent 11 between 90-100 ℃, reclaims and uses.The crude product 6 (including the substituted benzyl alcohol of 85-90%, the raw material substituted benzyl chlorine of 0.1-5%, the by product of 0.5-6%, as two ethers) of bottom, evaporation back oily liquids enters into rectifying tower D.In order to reduce heat energy consumption, can the heat transferred mixing tank M of condenser L be heated raw material by heat exchanger T.
In rectifying tower D, control pressure is at 1.33kPa, and the raw material substituted benzyl halogen 8 of top discharge for reclaiming is 110-120 ℃ in the middle part temperature, and overhead product is the substituted benzyl alcohol 10 of purity＞99.99%, and the bottom is high boiling impurity two ethers 7.Bottom temp is controlled at 180 ℃.Operate continuously flow (rectifying tower continuously feeding flow) is controlled at 0.5kgh
-1
The water 9 that comes out from extraction reactor (dilute hydrochloric acid that contains 2-7%) enters the hydrochloric acid concentration tank.After further concentrating, can obtain the concentrated hydrochloric acid that concentration is 30-37%.In order further to guarantee the safety of emission gases, can pass through an absorption tower again, with remaining HCl gas absorption, obtain the dilute hydrochloric acid of 1-5%, after further concentrating, can obtain the concentrated hydrochloric acid that concentration is 30-37%.The water that concentrates out turns back to steam oven and reuses.
Raw material substituted benzyl bromides 1 and water after the Hybrid Heating to 80 ℃, are added from reactor R top by pump in mixing tank M continuously, and the volume ratio of substituted benzyl halogen and water is 1: 5.Reactor temperature is controlled at 160-180 ℃.Reactor R is the tubular type isothermal reactor, the inner inert filler (as Raschig ring) of filling.The reactor aspect ratio is 1: 7, and pressure-controlling is at 0.2MPa.Raw material substituted benzyl bromides 1 evenly is sprayed on the filler by the sparger at reactor R top, feeds water vapor 2 from reactor head simultaneously, passes through reactor R with substituted benzyl bromides 1 and stream.Raw material substituted benzyl bromides 1 distributes on the inert filler in reactor in liquid mode, forms the form of trickle bed, has increased mass transfer area, has improved mass-transfer efficiency; Raw water steam 2 contacts with substituted benzyl bromides 1 with gaseous state, finishes hydrolysis reaction.The air speed of raw material substituted benzyl bromides 1 is 0.2h
-1, the air speed of water vapor 2 is 0.4h
-1
After coming out from reactor R, reaction mixture 3 enters condenser L, and refrigerative reaction mixture 4 enters extraction reactor E.In extraction reactor E, add chloroform and extract as extraction agent 11.After continuous extraction, reclaim water 9; Organic phase 5 enters vaporizer V, and holding temperature steams extraction agent 11 between 90-100 ℃, reclaims and uses.The crude product 6 (including the substituted benzyl alcohol of 85-90%, the raw material substituted benzyl halogen of 0.1-5%, the by product of 0.5-6%, as two ethers) of bottom, evaporation back oily liquids enters into rectifying tower D.In order to reduce heat energy consumption, can the heat transferred mixing tank M of condenser L be heated raw material by heat exchanger T.
In rectifying tower D, control pressure is at 1.33kPa, and the raw material substituted benzyl halogen 8 of top discharge for reclaiming is 110-120 ℃ in the middle part temperature, and overhead product is the substituted benzyl alcohol 10 of purity＞99.99%, and the bottom is high boiling impurity two ethers 7.Bottom temp is controlled at 150 ℃, and the operate continuously flow control is at 0.6-0.7kgh
-1
The water 9 that comes out from extraction reactor (hydrogen bromide that contains 2-7%) enters concentration tank.After further concentrating, can obtain the hydrogen bromide that concentration is 30-37%.The water that concentrates out turns back to steam oven and reuses.
The hydrolysis of embodiment 3:2-chlorobenzyl chloride prepares 2-chloro benzyl alcohol
With reference to the method (NM parameter is with embodiment 1) of embodiment 1,2-chlorobenzyl chloride and water (volume ratio 1: 1) are heated to 80 ℃, mix, by volume pump with air speed 0.2h
-1Enter into trickle-bed reactor, reactor R controlled temperature is 130-135 ℃, and pressure is 0.15MPa.Load Raschig ring in the reactor R, volume is 1L.Feed water vapor from reactor R top, air speed is 0.6h
-1By the oil phase behind the reactor R bed (being organic phase) after measured as can be known, contain 86% substituted benzyl alcohol, 4% dibenzyl ether and 10% contain 2.6% aqueous hydrochloric acid.
Reactant is cooled to 30 ℃ by condenser L, adds among the continuous extraction jar E, and extraction agent toluene adding speed is 0.2Lh
-1After the extracting and separating, water is a dilute hydrochloric acid solution, and organic phase enters retort V.
Keep vacuum 3330Pa in retort V, temperature is 50 ℃, removes extraction agent toluene continuously, and the residue oil phase enters rectifying tower D.
In rectifying tower D, keeping bottom temp is 175 ℃, carries out rectifying, and the rectifying tower middle part is the substituted benzyl alcohol of purity＞99.99%, and the top is the substituted benzyl halogen of 40-50%, and the bottom is an impurity disubstituted benzyl ether.
Claims (15)
1. the method for a continuous production substituted benzyl alcohol is characterized in that substituted benzyl halogen is mixed with water, and mixture and water vapor are parallel by the trickle bed reaction unit, continuous hydrolysis with separate, produce substituted benzyl alcohol;
Wherein, substituted benzyl halogen is suc as formula shown in (I), and substituted benzyl alcohol is suc as formula shown in (II):
Here, k represents an integer of 1～2, l represents an integer of 0～5, m represents an integer of 0～5, n represents an integer of 0～4, (k+l+m+n) be an integer of 2～6, the substituting group that R represents is bromine, trifluoromethyl, itrile group, nitro, amide group, alkoxyl group or aryloxy, and X represents Cl, Br or I.
2. method according to claim 1 is characterized in that substituted benzyl halogen suc as formula shown in (III), and substituted benzyl alcohol is suc as formula shown in (IV):
Here, k, l, m, X are identical with the definition in the claim 1.
3. method according to claim 1 is characterized in that substituted benzyl halogen shown in formula V, and substituted benzyl alcohol is suc as formula shown in (VI):
Here, k, l, n, R, X are identical with the definition in the claim 1.
4. method according to claim 1 is characterized in that substituted benzyl halogen suc as formula shown in (VII), and substituted benzyl alcohol is suc as formula shown in (VIII):
Here, k, l, X are identical with the definition in the claim 1.
5. method according to claim 4 is characterized in that substituted benzyl halogen suc as formula shown in (IX), and substituted benzyl alcohol is suc as formula shown in (X):
Here, l, X are identical with the definition in the claim 1.
6. method according to claim 5 is characterized in that 1 is 1,2 or 3, and X is a chlorine.
7. method according to claim 1 is characterized in that temperature of reaction is 40～220 ℃; Reaction pressure 0～5 MPa; The water yield is 1～40 times of substituted benzyl halogen amount by volume.
8. method according to claim 7 is characterized in that temperature of reaction is 80～180 ℃; Reaction pressure is 0～3 MPa; The water yield is 1～15 times of substituted benzyl halogen amount by volume.
9. method according to claim 8 is characterized in that temperature of reaction is 120～150 ℃; Reaction pressure is 0～1 MPa; The water yield is 1～5 times of substituted benzyl halogen amount by volume.
10. method according to claim 1 is characterized in that reclaiming the haloid acid in the mixed reaction product.
11. method according to claim 1 is characterized in that:
(1) raw material substituted benzyl halogen and water vapor are parallel by the trickle bed reaction unit;
(2) filler in the trickle bed reaction unit is an inert fill material;
(3) the hydrolysis reaction product is by extracting and separating water and organic phase, and water is to contain the haloid acid aqueous solution, and organic phase is to contain substituted benzyl halogen, substituted benzyl alcohol, disubstituted benzyl ether mixed solution;
(4) organic phase can obtain thick substituted benzyl alcohol by underpressure distillation;
(5) thick substituted benzyl alcohol is through one-level rectifying, can obtain unreacting material substituted benzyl halogen, the pure and mild impurity disubstituted benzyl of substituted benzyl ether simultaneously, recyclable the re-using of raw material substituted benzyl halogen, the aqueous solution that contains the haloid acid of lower concentration further concentrates the aqueous solution that can obtain dense haloid acid.
12. method according to claim 11 is characterized in that extraction agent is the organic solvent of 1-9 carbon, these organic solvents are benzene, toluene, ethylbenzene, dimethylbenzene, methylene dichloride, chloroform, ethylene dichloride, trichloroethane.
13., it is characterized in that the trickle bed reaction unit comprises mixing tank, reactor, condenser, interchanger, extraction reactor, vaporizer and rectifying tower according to the method for the described continuous production substituted benzyl alcohol of claim 1.
14. adopt the device of the described method of claim 1, it is characterized in that this device is the trickle bed reaction unit, comprises mixing tank, reactor, condenser, interchanger, extraction reactor, vaporizer and rectifying tower.
15. device according to claim 14, it is characterized in that mixing tank, reactor, condenser, interchanger, extraction reactor, the order of connection of vaporizer and rectifying tower is: mixer outlet links to each other with reactor one end entrance, reactor outlet links to each other with condenser inlet, condensator outlet links to each other with the extraction reactor inlet, extraction reactor one brings out mouth and links to each other with evaporator inlet, the other end outlet is used to discharge isolating water, vaporizer one brings out mouth and links to each other with the rectifying tower inlet, the other end outlet is used to discharge isolating extraction agent, the rectifying tower outlet is divided into the top, the middle part, outlet at bottom, interchanger connects condenser and mixing tank.
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| CN103588622B (en) * | 2013-11-29 | 2015-09-02 | 上海多纶化工有限公司 | The method of continuous hydrolysis Reactive Synthesis 2-methallyl alcohol |
| CN104645898A (en) * | 2015-03-17 | 2015-05-27 | 华北电力大学 | Trickle-bed reaction device and process for synthetic gas methanation |
| CN109810002A (en) * | 2019-02-14 | 2019-05-28 | 安徽泰格生物技术股份有限公司 | A kind of method that useless bromobenzyl prepares benzylamine |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US575081A (en) * | 1897-01-12 | Samuel turner | ||
| US5670029A (en) * | 1995-10-10 | 1997-09-23 | Bayer Aktiengesellschaft | Process for the separation of a mixture of benzyl chloride, benzyl alcohol, dibenzyl ether and aqueous hydrochloric acid |
| US5728897A (en) * | 1995-06-06 | 1998-03-17 | Bayer Aktiengesellschaft | Process for the preparation of benzyl alcohol |
-
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US575081A (en) * | 1897-01-12 | Samuel turner | ||
| US5728897A (en) * | 1995-06-06 | 1998-03-17 | Bayer Aktiengesellschaft | Process for the preparation of benzyl alcohol |
| US5670029A (en) * | 1995-10-10 | 1997-09-23 | Bayer Aktiengesellschaft | Process for the separation of a mixture of benzyl chloride, benzyl alcohol, dibenzyl ether and aqueous hydrochloric acid |
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