CN103588622A - Method for synthesizing 2-methallyl alcohol through continuous hydrolysis reaction - Google Patents
Method for synthesizing 2-methallyl alcohol through continuous hydrolysis reaction Download PDFInfo
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- CN103588622A CN103588622A CN201310624595.3A CN201310624595A CN103588622A CN 103588622 A CN103588622 A CN 103588622A CN 201310624595 A CN201310624595 A CN 201310624595A CN 103588622 A CN103588622 A CN 103588622A
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- C07—ORGANIC CHEMISTRY
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- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/12—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids
- C07C29/124—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of esters of mineral acids of halides
Abstract
The present invention relates to a method for synthesizing 2-methallyl alcohol through a continuous hydrolysis reaction. The method comprises: 1, water, an alkali, a phase transfer catalyst and 2-methyl allyl chloride are uniformly mixed in a material preparing container to obtain a raw material mixture; 2, the raw material mixture is continuously input to the tower kettle, and evaporation is performed on the tower kettle to produce 2-methyl allyl chloride steam and the tower bottom liquid, wherein the 2-methyl allyl chloride steam rises and enters a filler bed layer; 3, a reactor circulation material and a product post-treatment material are extracted from the tower kettle, wherein the reactor circulation material is input into the tower top, then descends in the reactor, is subjected to a hydrolysis reaction with the 2-methyl allyl chloride steam at the filler bed layer, and then enters the tower bottom liquid; and 4, the unreacted 2-methyl allyl chloride rises to the tower top, and is extracted out of the reactor in the 2-methyl allyl chloride exhaust gas form, wherein the reactor pressure is 10-100 kPa, and the reactor temperature is 90-100 DEG C.
Description
Technical field
The present invention relates to the method for the synthetic 2-methallyl alcohol of continuous hydrolysis reaction.
Technical background
2-methallyl alcohol (have another name called methylallyl alcohol, 1-hydroxy-2-methyl third rare etc.) is a kind of very important organic intermediate, and autohemagglutination and copolyreaction can occur for itself.Take 2-methallyl alcohol as initiator, can prepare methacrylic acid and ester.In addition, 2-methallyl alcohol can also generate allylic ester with other organic acid.Therefore, 2-methallyl alcohol is widely used in the fields such as polymer monomer and tensio-active agent.
The synthetic method of 2-methallyl alcohol is to take 2-methallyl chloride as raw material the earliest, under alkaline condition, is hydrolyzed and is prepared.Again there are many improved methods on this basis thereafter.
US2072015 proposes 120 ℃, under sodium hydroxide or sodium carbonate catalysis, under 5 normal atmosphere, is hydrolyzed, and this synthetic method needs realization response under condition of high voltage, higher to equipment requirements.
US2323781 adopts the method for the auxiliary salt of wormwood hydrolysis of electrolytic copper, and the method production cost is relatively high, and simultaneous reactions process can produce reluctant copper-containing wastewater.
US2313767 propose tensio-active agent pull open powder sodium naphthasulfonate exist under hydrolysis, this production method need to use price relatively high pull open powder, improved production cost, and target product yield is lower.
CN101759528 adopts water, solid alkali, 2-methallyl chloride and polyoxyethylene glycol is added in reaction vessel successively, then adds backflow, and drips the synthetic 2-methallyl alcohol of method that alkali lye carries out intermittent hydrolysis.The method is periodical operation, and byproduct of reaction diether is high, affects selectivity of product.
Summary of the invention
What the present invention will solve is the low problem of 2-methallyl alcohol selectivity existing in existing batch hydrolysis, the method of the synthetic 2-methallyl alcohol of a kind of continuous hydrolysis reaction is provided, the method production cost is low, and 2-methallyl chloride transformation efficiency is high, and 2-methallyl alcohol selectivity is high.
In order to solve the problems of the technologies described above, technical scheme of the present invention is as follows: the method for the synthetic 2-methallyl alcohol of continuous hydrolysis reaction, described method adopts packing tower reactor, described inside reactor is divided into tower reactor (3), filling batch (4a, 4b) and tower top (5), comprise the steps:
A, in proportion container (1), water, alkali, phase-transfer catalyst and 2-methallyl chloride are mixed and obtain raw mixture;
B, above-mentioned raw materials mixture is inputted to tower reactor (3) and liquid at the bottom of tower reactor evaporation generates 2-methallyl chloride steam and tower continuously; Described 2-methallyl chloride steam rising enters filling batch (4a, 4b);
C, from tower reactor extraction reactor cycles material (7) and product aftertreatment material (8); Described reactor cycles material input tower top (5), then descending in reactor, filling batch (4a, 4b) and 2-methallyl chloride steam be hydrolyzed enter tower after reacting at the bottom of liquid;
D, unreacted 2-methallyl chloride rise to tower top (5), and with the form extraction reactor of 2-methallyl chloride tail gas (6);
Wherein the pressure of reactor is counted 10～100KPa with gauge pressure; The temperature of reactor is 90-100 ℃.
In technique scheme, in step a by quality ratio, 2-methallyl chloride: alkali: water: phase-transfer catalyst is preferably 1:(0.3～0.5): (1～5): (0.001～0.003).
In technique scheme, the alkali described in step a is at least one in sodium hydroxide, potassium hydroxide, salt of wormwood, saleratus, sodium carbonate or sodium bicarbonate preferably.
In technique scheme, the phase-transfer catalyst described in step a comprises at least one in polyoxyethylene glycol, benzyltriethylammoinium chloride, Tetrabutyl amonium bromide, tetrabutylammonium chloride, tri-n-octyl methyl ammonium chloride, glycerol polyethenoxy ether or Dodecyl trimethyl ammonium chloride.Described phase-transfer catalyst more preferably comprises and is selected from polyoxyethylene glycol, benzyltriethylammoinium chloride, Tetrabutyl amonium bromide, tetrabutylammonium chloride, the glycerol polyethenoxy ether that at least one in tri-n-octyl methyl ammonium chloride or Dodecyl trimethyl ammonium chloride and the equal molecule molecular weight of number are 1500～3000, now there is higher 2-methallyl chloride transformation efficiency and the selectivity to 2-methallyl alcohol, more preferably by polyoxyethylene glycol, benzyltriethylammoinium chloride, Tetrabutyl amonium bromide, tetrabutylammonium chloride, at least one in tri-n-octyl methyl ammonium chloride or Dodecyl trimethyl ammonium chloride is 1:(0.05～0.2 with the glycerol polyethenoxy ether that the equal molecule molecular weight of number is 1500～3000 in mass ratio) form.
In technique scheme, after described reactor cycles material input tower top (5), preferably the mode by spray distributes to bed of packings upper surface.
In technique scheme, the 2-methallyl chloride tail gas (6) described in steps d is optional without condensation or through condenser (13) condensation, then preferably by defeated time tower reactor of tail gas recycle pipeline (14) (3).
In technique scheme, the product aftertreatment material (8) described in step c preferably obtains thick product oil phase (11) and waste water phase (12) through product aftertreatment refrigerating work procedure (9), oily water separation operation (10) successively.
In technique scheme, the preferably further drying dehydration of the thick product oil phase (11) obtaining is further purified.
In technique scheme, the waste water phase (12) obtaining is preferably returned to step a reuse after desalination.The mode of desalination adopts those conventional methods of this area, for example, by filtering desalination.
In technique scheme, the filler of described filling batch is preferably screen waviness structured packing, preferably divides two-layerly, is respectively upper strata (4a) and lower floor (4b), preferably establishes redistributor in the middle of levels.
In technique scheme, reactor residence time is preferably 4～35 hours.
The inventive method, owing to adopting continuous hydrolysis technology, has overcome the deficiency of batch technology, and the transformation efficiency of 2-methallyl chloride can reach more than 88%, and the selectivity of 2-methallyl alcohol is greater than to 92%, has obtained good technique effect.
Below in conjunction with accompanying drawing explanation and embodiment, the present invention is described in detail.
Accompanying drawing explanation
Fig. 1 is the technical process that one embodiment of the present invention adopts.
Technical process is: in proportion container (1), water, alkali, phase-transfer catalyst and 2-methallyl chloride are mixed and obtain raw mixture; Above-mentioned raw materials mixture is inputted to tower reactor (3) and liquid at the bottom of tower reactor (3) evaporation generates 2-methallyl chloride steam and tower continuously; Described 2-methallyl chloride steam rising enters filling batch (4a, 4b); From tower reactor extraction reactor cycles material (7) and product aftertreatment material (8); Described reactor cycles material input tower top (5), then descending in reactor, filling batch (4a, 4b) and 2-methallyl chloride steam be hydrolyzed enter tower after reacting at the bottom of liquid; Unreacted 2-methallyl chloride rises to tower top (5), and with the form extraction reactor of 2-methallyl chloride tail gas (6) through condenser (13) condensation by defeated time tower reactor of recovery line (14) (3); After described reactor cycles material input tower top (5), by spray face, to bed of packings, distribute; Product aftertreatment material (8) successively, oily water separation operation (10) cooling through product aftertreatment refrigerating work procedure (9) obtains thick product oil phase (11) and waste water phase (12).The filler of filling batch (4a, 4b) filling batch is screen waviness structured packing, minute two-layer, is respectively upper strata (4a) and lower floor (4b), and redistributor is established in levels centre.
Technical process described in accompanying drawing 1 is not that enforcement sole mode of the present invention is only more excellent embodiment, and those skilled in the art still can implement the present invention without creative work by rational change under instruction of the present invention.Following examples all adopt the technical process shown in accompanying drawing 1.
Embodiment
[embodiment 1]
Reaction conditions is:
Raw mixture forms 2-methallyl chloride by quality ratio: alkali: water: phase-transfer catalyst is 1:0.4:3:0.02; Alkali is sodium hydroxide, and phase-transfer catalyst is Tetrabutyl amonium bromide; The pressure of reactor is counted 60KPa with gauge pressure; The temperature of reactor is 95 ℃; In reactor, the residence time is 18 hours.
Reaction result is:
2-methallyl chloride transformation efficiency is 88.9%;
The selectivity of 2-methallyl alcohol is 94.2%.
[embodiment 2]
Reaction conditions is:
Raw mixture forms 2-methallyl chloride by quality ratio: alkali: water: phase-transfer catalyst is 1:0.3:1:0.001; Alkali is sodium hydroxide, and phase-transfer catalyst is Tetrabutyl amonium bromide; The pressure of reactor is counted 100KPa with gauge pressure; The temperature of reactor is 100 ℃; In reactor, the residence time is 32 hours.
Reaction result is:
2-methallyl chloride transformation efficiency is 90.8%;
The selectivity of 2-methallyl alcohol is 93.2%.
[embodiment 3]
Reaction conditions is:
Raw mixture forms 2-methallyl chloride by quality ratio: alkali: water: phase-transfer catalyst is 1:0.5:5:0.003; Alkali is sodium hydroxide, and phase-transfer catalyst is Tetrabutyl amonium bromide; The pressure of reactor is counted 10KPa with gauge pressure; The temperature of reactor is 90 ℃; In reactor, the residence time is 4 hours.
Reaction result is:
2-methallyl chloride transformation efficiency is 89.3%;
The selectivity of 2-methallyl alcohol is 94.1%.
[embodiment 4]
Reaction conditions is:
Raw mixture forms 2-methallyl chloride by quality ratio: alkali: water: phase-transfer catalyst is 1:0.4:3:0.02; Alkali is sodium hydroxide, and phase-transfer catalyst is PEG600; The pressure of reactor is counted 60KPa with gauge pressure; The temperature of reactor is 95 ℃; In reactor, the residence time is 18 hours.
Reaction result is:
2-methallyl chloride transformation efficiency is 88.5%;
The selectivity of 2-methallyl alcohol is 92.1%.
[embodiment 5]
Reaction conditions is:
Raw mixture forms 2-methallyl chloride by quality ratio: alkali: water: phase-transfer catalyst is 1:0.4:3:0.02; Alkali is sodium hydroxide, and phase-transfer catalyst is benzyltriethylammoinium chloride; The pressure of reactor is counted 60KPa with gauge pressure; The temperature of reactor is 95 ℃; In reactor, the residence time is 18 hours.
Reaction result is:
2-methallyl chloride transformation efficiency is 91.6%;
The selectivity of 2-methallyl alcohol is 92.3%.
[embodiment 6]
Reaction conditions is:
Raw mixture forms 2-methallyl chloride by quality ratio: alkali: water: phase-transfer catalyst is 1:0.4:3:0.02; Alkali is sodium hydroxide, and phase-transfer catalyst is tri-n-octyl methyl ammonium chloride; The pressure of reactor is counted 60KPa with gauge pressure; The temperature of reactor is 95 ℃; In reactor, the residence time is 18 hours.
Reaction result is:
2-methallyl chloride transformation efficiency is 90.2%;
The selectivity of 2-methallyl alcohol is 93.3%.
[embodiment 7]
Reaction conditions is:
Raw mixture forms 2-methallyl chloride by quality ratio: alkali: water: phase-transfer catalyst is 1:0.4:3:0.02; Alkali is sodium hydroxide, and phase-transfer catalyst is Dodecyl trimethyl ammonium chloride; The pressure of reactor is counted 60KPa with gauge pressure; The temperature of reactor is 95 ℃; In reactor, the residence time is 18 hours.
Reaction result is:
2-methallyl chloride transformation efficiency is 90.5%;
The selectivity of 2-methallyl alcohol is 93.0%.
[embodiment 8]
Reaction conditions is:
Raw mixture forms 2-methallyl chloride by quality ratio: alkali: water: phase-transfer catalyst is 1:0.4:3:0.02; Alkali is sodium hydroxide, and phase-transfer catalyst is the composition that glycerol poly(propylene oxide) that Tetrabutyl amonium bromide and number-average molecular weight are 2000 is obtained by mixing for 1:0.05 in mass ratio; The pressure of reactor is counted 60KPa with gauge pressure; The temperature of reactor is 95 ℃; In reactor, the residence time is 18 hours.
Reaction result is:
2-methallyl chloride transformation efficiency is 97.2%;
The selectivity of 2-methallyl alcohol is 97.5%.
[embodiment 9]
Reaction conditions is:
Raw mixture forms 2-methallyl chloride by quality ratio: alkali: water: phase-transfer catalyst is 1:0.4:3:0.02; Alkali is sodium hydroxide, and phase-transfer catalyst is that PEG600 and number-average molecular weight are the composition that 2000 glycerol poly(propylene oxide) is obtained by mixing for 1:0.05 in mass ratio; The pressure of reactor is counted 60KPa with gauge pressure; The temperature of reactor is 95 ℃; In reactor, the residence time is 18 hours.
Reaction result is:
2-methallyl chloride transformation efficiency is 97.5%;
The selectivity of 2-methallyl alcohol is 97.1%.
[embodiment 10]
Reaction conditions is:
Raw mixture forms 2-methallyl chloride by quality ratio: alkali: water: phase-transfer catalyst is 1:0.4:3:0.02; Alkali is sodium hydroxide, and phase-transfer catalyst is that benzyltriethylammoinium chloride and number-average molecular weight are the composition that 2500 glycerol poly(propylene oxide) is obtained by mixing for 1:0.1 in mass ratio; The pressure of reactor is counted 60KPa with gauge pressure; The temperature of reactor is 95 ℃; In reactor, the residence time is 18 hours.
Reaction result is:
2-methallyl chloride transformation efficiency is 97.6%;
The selectivity of 2-methallyl alcohol is 96.3%.
[embodiment 11]
Reaction conditions is:
Raw mixture forms 2-methallyl chloride by quality ratio: alkali: water: phase-transfer catalyst is 1:0.4:3:0.02; Alkali is sodium hydroxide, and phase-transfer catalyst is that tri-n-octyl methyl ammonium chloride and number-average molecular weight are the composition that 3000 glycerol poly(propylene oxide) is obtained by mixing for 1:0.2 in mass ratio; The pressure of reactor is counted 60KPa with gauge pressure; The temperature of reactor is 95 ℃; In reactor, the residence time is 18 hours.
Reaction result is:
2-methallyl chloride transformation efficiency is 97.2%;
The selectivity of 2-methallyl alcohol is 97.1%.
[embodiment 12]
Reaction conditions is:
Raw mixture forms 2-methallyl chloride by quality ratio: alkali: water: phase-transfer catalyst is 1:0.4:3:0.02; Alkali is sodium hydroxide, and phase-transfer catalyst is that Dodecyl trimethyl ammonium chloride and number-average molecular weight are the composition that 1500 glycerol poly(propylene oxide) is obtained by mixing for 1:0.2 in mass ratio; The pressure of reactor is counted 60KPa with gauge pressure; The temperature of reactor is 95 ℃; In reactor, the residence time is 18 hours.
Reaction result is:
2-methallyl chloride transformation efficiency is 97.5%;
The selectivity of 2-methallyl alcohol is 96.6%.
[embodiment 13]
Reaction conditions is:
Raw mixture forms 2-methallyl chloride by quality ratio: alkali: water: phase-transfer catalyst is 1:0.4:3:0.02; Alkali is sodium hydroxide, and phase-transfer catalyst is that number-average molecular weight is 2000 glycerol poly(propylene oxide); The pressure of reactor is counted 60KPa with gauge pressure; The temperature of reactor is 95 ℃; In reactor, the residence time is 18 hours.
Reaction result is:
2-methallyl chloride transformation efficiency is 65.9%;
The selectivity of 2-methallyl alcohol is 79.2%.
Claims (10)
1. the method that 2-methallyl alcohol is synthesized in continuous hydrolysis reaction, described method adopts packing tower reactor, and described inside reactor is divided into tower reactor (3), filling batch (4a, 4b) and tower top (5), comprises the steps:
A, in proportion container (1), water, alkali, phase-transfer catalyst and 2-methallyl chloride are mixed and obtain raw mixture;
B, above-mentioned raw materials mixture is inputted to tower reactor (3) and liquid at the bottom of tower reactor evaporation generates 2-methallyl chloride steam and tower continuously; Described 2-methallyl chloride steam rising enters filling batch (4a, 4b);
C, from tower reactor extraction reactor cycles material (7) and product aftertreatment material (8); Described reactor cycles material input tower top (5), then descending in reactor, filling batch (4a, 4b) and 2-methallyl chloride steam be hydrolyzed enter tower after reacting at the bottom of liquid;
D, unreacted 2-methallyl chloride rise to tower top (5), and with the form extraction reactor of 2-methallyl chloride tail gas (6);
Wherein the pressure of reactor is counted 10～100KPa with gauge pressure; The temperature of reactor is 90-100 ℃.
2. method according to claim 1, is characterized in that in step a by quality ratio 2-methallyl chloride: alkali: water: phase-transfer catalyst is 1:(0.3～0.5): (1～5): (0.001～0.003).
3. method according to claim 1, is characterized in that the alkali described in step a is selected from least one in sodium hydroxide, potassium hydroxide, salt of wormwood, saleratus, sodium carbonate or sodium bicarbonate.
4. method according to claim 1, is characterized in that the phase-transfer catalyst described in step a comprises at least one in polyoxyethylene glycol, benzyltriethylammoinium chloride, Tetrabutyl amonium bromide, tetrabutylammonium chloride, tri-n-octyl methyl ammonium chloride or Dodecyl trimethyl ammonium chloride.
5. method according to claim 1, is characterized in that described in step c after reactor cycles material input tower top (5) that the mode by spray distributes to bed of packings upper surface.
6. method according to claim 1, is characterized in that 2-methallyl chloride tail gas (6) described in steps d is without condensation or through condenser (13) condensation, then by defeated time tower reactor of tail gas recycle pipeline (14) (3).
7. method according to claim 1, is characterized in that the product aftertreatment material (8) described in step c obtains thick product oil phase (11) and waste water phase (12) through product aftertreatment refrigerating work procedure (9), oily water separation operation (10) successively.
8. method according to claim 7, is characterized in that the further drying dehydration of the thick product oil phase (11) obtaining is further purified.
9. method according to claim 8, is characterized in that the waste water phase (12) obtaining returns to step a reuse after desalination.
10. method according to claim 1, is characterized in that the filler of described filling batch is screen waviness structured packing, minute two-layer, is respectively upper strata (4a) and lower floor (4b), and redistributor is established in levels centre.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104341255A (en) * | 2014-09-19 | 2015-02-11 | 江苏省建筑科学研究院有限公司 | Preparation method of unsaturated alcohol |
| CN107235816A (en) * | 2017-05-25 | 2017-10-10 | 温州大学 | A kind of method that halogenated hydrocarbons hydrolysis prepares alcohol |
| CN111170828A (en) * | 2020-01-17 | 2020-05-19 | 浙江大学宁波理工学院 | Method for preparing methallyl alcohol using in situ generated Cu (I) catalyst |
| CN115838327A (en) * | 2022-12-06 | 2023-03-24 | 常州久日化学有限公司 | Alkaline hydrolysis method of photoinitiator 184 |
| CN115838327B (en) * | 2022-12-06 | 2024-05-03 | 湖南久日新材料有限公司 | Alkaline hydrolysis method of photoinitiator 184 |
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| JP2002371023A (en) * | 2001-06-13 | 2002-12-26 | Toagosei Co Ltd | Method for producing (meth)allyl alcohol |
| CN1709845A (en) * | 2005-06-20 | 2005-12-21 | 南京工业大学 | Method for producing substituted benzyl alcohol by continuous process and its apparatus |
| CN101759528A (en) * | 2010-01-12 | 2010-06-30 | 宁波尖锋紫星生物科技有限公司 | Synthesizing method of 2-methallyl alcohol |
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| US5105030A (en) * | 1990-07-06 | 1992-04-14 | Huels Aktiengesellschaft | Method of manufacturing dihydromyrcenol from dihydromyrcenyl chloride |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104341255A (en) * | 2014-09-19 | 2015-02-11 | 江苏省建筑科学研究院有限公司 | Preparation method of unsaturated alcohol |
| CN107235816A (en) * | 2017-05-25 | 2017-10-10 | 温州大学 | A kind of method that halogenated hydrocarbons hydrolysis prepares alcohol |
| CN111170828A (en) * | 2020-01-17 | 2020-05-19 | 浙江大学宁波理工学院 | Method for preparing methallyl alcohol using in situ generated Cu (I) catalyst |
| CN111170828B (en) * | 2020-01-17 | 2023-01-03 | 浙江大学宁波理工学院 | Method for preparing methallyl alcohol using in situ generated Cu (I) catalyst |
| CN115838327A (en) * | 2022-12-06 | 2023-03-24 | 常州久日化学有限公司 | Alkaline hydrolysis method of photoinitiator 184 |
| CN115838327B (en) * | 2022-12-06 | 2024-05-03 | 湖南久日新材料有限公司 | Alkaline hydrolysis method of photoinitiator 184 |
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