CN103922894A - Preparation method of isopentenol - Google Patents
Preparation method of isopentenol Download PDFInfo
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- CN103922894A CN103922894A CN201410185588.2A CN201410185588A CN103922894A CN 103922894 A CN103922894 A CN 103922894A CN 201410185588 A CN201410185588 A CN 201410185588A CN 103922894 A CN103922894 A CN 103922894A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
- C07C29/095—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 organic acids
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Abstract
The invention discloses a preparation method of isopentenol. The method comprises the following steps: slowly adding isoprene into a system consisting of an organic carboxylic acid and corresponding salt, wherein the Ka value of the system is greater than 10<-4> relative to water; continuously stirring at room temperature till reaction is completed, and extracting and separating out isoamylene chloroacetate; and adding a strongly basic alcohol-water solution into isoamylene chloroacetate to carry out hydrolysis at room temperature, and after reaction is completed, extracting and separating impurities to obtain isoamyl alcohol. The preparation method can be carried out at normal temperature and normal pressure. Compared with industrially common synthetic method of isoamyl alcohol by a hydrogen chloride method, the method does not need high temperature and high pressure, is short in the process flow, mild in the reaction condition, and is improved in terms of safety and stability.
Description
Technical field
The present invention relates to the synthetic field of chemical feedstocks, relate in particular to a kind of preparation method of prenol.
Technical background
Prenol, chemical name is 3-M2BOL (3-methyl-2-butene-1-ol), is colourless transparent liquid, flash-point 43
oc, density 0.848 g/cm
3, boiling point 140
oc, its solubleness in water is 170 g/L (20
oc), relative molecular weight is 86.13.It,, at the industrial raw material 3,3-dimethyl-4-pentenoic acid methyl ester that is mainly used in synthetic chrysanthemum ester insecticide, also can be used as spices synthesis material.
The synthetic route of prenol mainly contains acetone method, iso-butylene method and isoprene method, wherein acetone method employing acetylene is raw material, cost is high, operational path is long, product yield is low, need take precious metal as catalyzer carries out shortening, further strengthened production cost, the industrial synthetic prenol of acetone method of progressively eliminating.Iso-butylene method is that to take polyoxymethylene and iso-butylene be raw material, under Sodium phosphate dibasic catalytic condition, reaction generates the mixture of 3-methyl-3-butene-1-alcohol and 3-M2BOL (prenol), wherein 3-methyl-3-butene-1-alcohol Ba ∕ carbon is that under catalyst action, transposition becomes 3-M2BOL (prenol), this legal system is large for primary isoamyl alcohol facility investment, severe reaction conditions, production cost is also higher.
China's ethylene industry is very ripe, and petrochemical industry development is swift and violent, C
5the sustainable growth of by product output, isoprene output is very considerable.So Devoting Major Efforts To Developing be take isoprene and is prepared the new technology route of prenol as raw material, has stronger practicality and huge potentiality.
In prior art, isoprene legal system is to take isoprene as raw material for prenol, with the synthetic chloroisoamylene of hydrogen chloride gas catalysis addition, its isomer obtains chloro-3 methyl-2-butenes of 1-through catalysis, add aqueous sodium acetate solution, uniform stirring, temperature of reaction is controlled at 100 ~ 110
oc, the reaction times is 3 ~ 4 h, obtains isopentene acetic ester, adds 30%NaOH solution, reflux is hydrolyzed 3 h, extracting and separating underpressure distillation, collecting 52 ~ 58 ℃/2.7kPa cut is prenol.Each reaction process is as follows:
The method advantage is that reaction process is stable, and sodium acetate is recyclable, and total yield of products is higher, and raw material sources are abundant, and production cost is low, with the obvious advantage.But isoprene boiling point is low, to carry out in gas phase with HCl catalytic addition reaction, technological operation is wayward, and steam toxicity is larger, and the HCl using is very big to equipment corrosion, and reaction mechanism is longer, complex operation, severe reaction conditions, facility investment is large.
Summary of the invention:
The preparation method who the object of this invention is to provide a kind of prenol, the present invention adopts organic acid and the synthetic isopentene ester of isoprene direct reaction of certain strength of acid, the latter is hydrolyzed and obtains prenol, compared with prior art, obviously shortened technical process, avoid the corrosion of hydrogenchloride to conversion unit, reduced equipment investment and maintenance.
The preparation method of prenol of the present invention, comprises the following steps:
A, at K
avalue is greater than 10 with respect to water
-4organic carboxyl acid and the system that forms of corresponding salt in slowly add isoprene, under room temperature, be constantly stirred to and react completely, extracting and separating goes out prenyl chloride for acetic ester;
The system that described organic carboxyl acid and corresponding salt thereof form is divided into two kinds of situations, a kind of for organic acid be liquid, directly use organic acid to coordinate its organic acid salt compositional system: the second is that organic acid is solid, except organic acid and its organic acid salt, add dehydrated alcohol or methyl alcohol compositional system, add-on is so that whole system is liquid; Preferably, dehydrated alcohol or methyl alcohol add-on are the saturated or near saturated solution of organic acid.
B, at prenyl chloride, add alkaline alcohol solution in for acetic ester, be at room temperature hydrolyzed, after reacting completely, extracting and separating is removed impurity, obtains prenol.
In described steps A, extracting and separating goes out prenyl chloride and refers to for acetic ester: the mixed solution that with weightmeasurement ratio is 8-15% sodium chloride aqueous solution and hexane carries out extracting and separating as extraction liquid, obtain prenyl chloride for the hexane solution of acetic ester, this for hexane solution saturated sodium bicarbonate solution, saturated nacl aqueous solution successively each washing once after, add anhydrous magnesium sulfate to remove moisture, hexane is sloughed in underpressure distillation, collect prenyl chloride for acetic ester cut, obtain.
After reacting completely in described step B, extracting and separating removal impurity refers to: after hydrolysis finishes, add extraction liquid, isolate organic layer and wash with saturated sodium-chloride, and anhydrous magnesium sulfate drying, organic solvent is sloughed in decompression, obtains prenol; Described extraction liquid is the saturated sodium-chloride water solution of 80-120 weight part, and pentane, ether equivalent mixed liquor with 40-80 weight part, mix composition.
Described K
avalue is greater than 10 with respect to water
-4organic carboxyl acid and the system of corresponding salt in, the molar ratio of organic carboxyl acid and corresponding salt thereof is 15 ~ 23:0.3 ~ 0.5.
Described isoprene and the mol ratio of organic carboxyl acid are 1:15 ~ 23.
Preferably, the molar ratio of described isoprene, organic carboxyl acid and corresponding salt thereof is 1.0:19 ~ 21:0.35 ~ 0.45.
Described alkaline alcohol solution refers to the alcohol solution that pH is 12-14.
Preferably, described alkaline alcohol solution refers to the methanol aqueous solution that pH is the sodium hydroxide of 13-14.
Described organic carboxyl acid is chloracetic acid, oxalic acid.
The corresponding salt of described organic carboxyl acid is an alkali metal salt of chloracetic acid, oxalic acid.
Preferably, described organic carboxyl acid and corresponding salt thereof are Monochloro Acetic Acid, dichloro acetic acid, trichoroacetic acid(TCA) and corresponding sodium salt or sylvite thereof.
The present invention adopts isoprene and the direct catalysis addition of organic carboxyl acid, synthesizes isopentene acetic ester, prepares the technique of prenol through basic hydrolysis, and its committed step is the synthetic isopentene acetic ester of catalysis addition
Wherein RCOOH is that its acidity is organic carboxyl acid, more than its intensity is medium, and K
avalue (with respect to water) requires to be greater than 10
-4, as Mono Chloro Acetic Acid (Ka=1.4 * 10
-3), dichloro acetic acid (Ka=5 * 10
-2), trichoroacetic acid(TCA) (Ka=2.2 * 10
-1), best is dichloro acetic acid.
For example adopt dichloro acetic acid sodium catalyst dichloro acetic acid to react with isoprene and generate isopentene dichloro acetic acid ester, isopentene dichloro acetic acid ester obtains target product prenol through hydrolysis reaction, while by-product dichloroacetate sodium, the latter can be used as catalyst recirculation and uses.Concrete reaction process is as follows:
。
Catalyzer: adopt the corresponding sodium salt of organic carboxyl acid of reaction raw materials, best is dichloroacetate sodium.
Solvent: addition reaction adopts excessive chloracetic acid, is the addition reaction raw material solvent of holding concurrently, or is the saturated or near saturated solution that solvent is made solid organic acid with dehydrated alcohol or methyl alcohol.Hydrolysis reaction adopts the strong basicity methanol-water solution of sodium hydroxide, the methanol-water solution of the sodium hydroxide that for example pH is 12-13.
The present invention generates isopentene ester by isoprene and carboxylic acid direct addition, then through the synthetic prenol of saponification reaction.The organic carboxyl acid Ka value (with respect to water) that can use in the present invention is greater than 10
-4, chloracetic acid for example, wherein dichloro acetic acid is a kind of ideal reactant.This reaction requires isoprene slowly to join in organic carboxyl acid, thus synthetic isopentene ester, and if add excessive velocities, isoprene will polymerization reaction take place, greatly reduces the reaction preference of isoprene.Esterification can be carried out at normal temperatures, and reaction needed is added organic catalyst, and sodium salt corresponding to carboxylic acid of participating in reaction have good catalytic effect, and reaction yield is higher.Especially take sodium chloroacetate as catalyzer, catalytic activity is good, and selectivity is higher, and catalyzer is recyclable to be reused.Product isopentene ester is under the alkaline condition of inorganic strong alkali alcohol solution, and reaction generates prenol.
The invention has the beneficial effects as follows:
The present invention is directed to the synthetic prenol technique of isoprene method in prior art and carried out larger improvement, can one-step synthesis isopentene ester, then by alkaline condition catalyzed reaction, generate prenol, avoided the corrosion to equipment of the hydrogen chloride gas that uses in original technique, reduce equipment investment; Reduced temperature of reaction simultaneously, at room temperature can carry out; And synthesis technique flow process shortens greatly, by four steps of prior art processes, foreshorten to two steps.Preparation method's reaction conditions provided by the invention is gentle, has improved safety and stability.
Embodiment
In order better to understand the present invention, below in conjunction with embodiment, further to set forth, these cases should not be construed as limitation of the present invention.
Embodiment 1
The Mono Chloro Acetic Acid that is 250 mmoles by 23.6g joins in 7g methyl alcohol, mixes, and makes Mono Chloro Acetic Acid methanol solution; Under room temperature, the sodium chloroacetate that is 5.01 mmoles by 583mg joins in Mono Chloro Acetic Acid methanol solution, be stirred to completely and dissolve, with the speed of 0.01 milliliter of per minute, slowly add 1.25 milliliters in the isoprene of 12.5 mmoles, isoprene: Mono Chloro Acetic Acid: sodium chloroacetate mol ratio=1:20:0.4, within approximately 130 minutes, drip off, then react 10 minutes.Add extraction liquid to carry out extracting and separating, described extraction liquid is 175 milliliters of weightmeasurement ratios sodium chloride aqueous solution that is 8% and the mixed solution of 125 milliliters of hexanes, after extraction, obtain and contain prenyl chloride acetic ester mixed solution, mixed solution respectively washs once successively with saturated sodium bicarbonate solution, the saturated nacl aqueous solution of 100 milliliters respectively.Add anhydrous magnesium sulfate to remove after moisture, hexane is sloughed in underpressure distillation, collects prenyl chloride acetic ester cut.In prenyl chloride acetic ester, add the mixing solutions by 10ml methyl alcohol and 0.3 milliliter of 0. 4mol/L aqueous sodium hydroxide solution, making pH is 12, reaction 2 hours is hydrolyzed, utilize 80 milliliters of saturated sodium-chloride water solutions, 40 milliliters of pentanes: the equal-volume mixed solution of ether mixes the extraction liquid of composition, extracts organic layer, organic layer is washed with 70 milliliters of saturated sodium-chlorides, anhydrous magnesium sulfate drying, organic solvent is sloughed in decompression, obtains prenol 439mg, yield 40.8%.
Embodiment 2
Under room temperature, the dichloroacetate sodium that is 5.0 mmoles by 755mg joins in the dichloro acetic acid that 19.6ml is 237.5 mmoles, be stirred to completely and dissolve, with the speed of 0.02 milliliter of per minute, slowly add 1.25 milliliters in the isoprene of 12.5 mmoles, isoprene: dichloro acetic acid: dichloroacetate sodium mol ratio=1:19:0.4, within approximately 130 minutes, drip off, then react 10 minutes.Add extraction liquid to carry out extracting and separating, described extraction liquid is 175 milliliters of weightmeasurement ratios sodium chloride aqueous solution that is 15% and the mixed solution of 125 milliliters of hexanes, after extraction, obtain and contain isopentene dichloro acetic acid ester mixed solution, mixed solution respectively washs once successively with saturated sodium bicarbonate solution, the saturated nacl aqueous solution of 125 milliliters respectively.Add anhydrous magnesium sulfate to remove after moisture, hexane is sloughed in underpressure distillation, collects isopentene dichloro acetic acid ester cut.In isopentene dichloro acetic acid ester, add the mixing solutions by 10ml methyl alcohol and 1.1 milliliters of 10mol/L aqueous sodium hydroxide solutions, making pH is 14, reaction 2 hours is hydrolyzed, utilize 120 milliliters of saturated sodium-chloride water solutions, 80 milliliters of pentanes: the equal-volume mixed solution of ether mixes the extraction liquid of composition, extracts organic layer, organic layer is washed with 80 milliliters of saturated sodium-chlorides, anhydrous magnesium sulfate drying, organic solvent is sloughed in decompression, obtains prenol 733mg, yield 68.1%.
Embodiment 3
The trichoroacetic acid(TCA) that is 187.5 mmoles by 30.6g joins in 2g methyl alcohol, mixes, and makes trichoroacetic acid(TCA) methanol solution; Under room temperature, the sodium trichloroacetate that is 3.75 mmoles by 695mg joins in trichoroacetic acid(TCA) methanol solution, be stirred to completely and dissolve, speed with 0.015 milliliter of per minute slowly adds in 1.25 milliliters of (12.5 mmole) isoprene, isoprene: trichoroacetic acid(TCA): sodium trichloroacetate mol ratio=1:15:0.3, within approximately 130 minutes, drip off, then react 10 minutes.Add extraction liquid to carry out extracting and separating, described extraction liquid is 170 milliliters of weightmeasurement ratios sodium chloride aqueous solution that is 10% and the mixed solution of 125 milliliters of hexanes, after extraction, obtain and contain isopentene trichloroacetic esters mixed solution, mixed solution respectively washs once successively with saturated sodium bicarbonate solution, the saturated nacl aqueous solution of 120 milliliters respectively.Add anhydrous magnesium sulfate to remove after moisture, hexane is sloughed in underpressure distillation, collects isopentene trichloroacetic esters cut.In isopentene trichloroacetic esters, add the mixing solutions by 10ml methyl alcohol and 1.2 milliliter of 0. 1mol/L aqueous sodium hydroxide solution, making pH is 12, reaction 2 hours is hydrolyzed, utilize 100 milliliters of saturated sodium-chloride water solutions, 65 milliliters of pentanes: the extraction liquid that the equal-volume mixed solution of ether mixes composition adds extraction liquid, extracts organic layer, organic layer is washed with 70 milliliters of saturated sodium-chlorides, anhydrous magnesium sulfate drying, organic solvent is sloughed in decompression, obtains prenol 548mg, yield 50.9%.
Embodiment 4
The Mono Chloro Acetic Acid that is 288 mmoles by 27.2g joins in 8g methyl alcohol, mixes, and makes Mono Chloro Acetic Acid methanol solution; Under room temperature, the sodium chloroacetate that is 6.25 mmoles by 728mg joins in Mono Chloro Acetic Acid methanol solution, be stirred to completely and dissolve, slowly add 1.25 milliliters in the isoprene of 12.5 mmoles, isoprene: Mono Chloro Acetic Acid: sodium chloroacetate mol ratio=1:23:0.5, add speed identical with embodiment 1, reaction times and product separation, with reference to embodiment 1, are collected prenyl chloride acetic ester cut.In prenyl chloride acetic ester, add the mixing solutions by 10ml methyl alcohol and 2.3 milliliters of 5mol/L aqueous sodium hydroxide solutions, making pH is 13.9, the reaction 2 hours that is hydrolyzed, and separating step, with embodiment 1, obtains prenol 454mg, yield 42.2%.
Embodiment 5
The oxalic acid that is 187.5 mmoles by 16.9g joins in 7g dehydrated alcohol, mixes, and makes oxalic acid ethanol solution; Under room temperature, the oxalic acid potassium that is 3.75 mmoles by 690mg joins in oxalic acid dehydrated alcohol alcoholic solution, be stirred to completely and dissolve, slowly add 1.25 milliliters of i.e. isoprene of 12.5 mmoles, isoprene: oxalic acid: oxalic acid potassium mol ratio=1:15:0.3, add speed identical with embodiment 2, reaction times and product separation, with reference to embodiment 2, are collected isopentene oxalic acid ester cut.In isopentene oxalic acid ester, add the mixing solutions by 10ml methyl alcohol and 1.5 milliliters of 6mol/L potassium hydroxide aqueous solutions, making pH is 13.6, the reaction 2 hours that is hydrolyzed, and separating step, with embodiment 2, obtains prenol 677mg, yield 62.9%.
Embodiment 6
The trichoroacetic acid(TCA) that is 225 mmoles by 36.7g joins in 2g methyl alcohol, mixes, and makes trichoroacetic acid(TCA) methanol solution; Under room temperature, the sodium trichloroacetate that is 6.25 mmoles by 1159mg joins in trichoroacetic acid(TCA) methanol solution, be stirred to completely and dissolve, slowly add 1.25 milliliters of i.e. isoprene of 12.5 mmoles, isoprene: trichoroacetic acid(TCA): sodium trichloroacetate mol ratio=1:18:0.5, add speed identical with embodiment 3, reaction times and product separation, with reference to embodiment 3, are collected isopentene trichloroacetic esters cut.In isopentene trichloroacetic esters, add the mixing solutions by 10ml methyl alcohol and 1.0 milliliters of 0.2mol/L aqueous sodium hydroxide solutions, making pH is 12, the reaction 2 hours that is hydrolyzed, and separating step, with embodiment 3, obtains prenol 580mg, yield 53.9%.
Embodiment 7
Under room temperature, the dichloro acetic acid potassium that is 6.26 mmoles by 1043mg joins in the dichloro acetic acid that 23.7ml is 288 mmoles, be stirred to completely and dissolve, slowly add 1.25 milliliters of i.e. isoprene of 12.5 mmoles, isoprene: dichloro acetic acid: dichloro acetic acid potassium mol ratio=1:23:0.5, add speed identical with embodiment 2, reaction times and product separation, with reference to embodiment 2, are collected isopentene dichloro acetic acid ester cut.In isopentene dichloro acetic acid ester, add the mixing solutions by 10ml methyl alcohol and 2.5 milliliters of 6mol/L aqueous sodium hydroxide solutions, making pH is 13.8, the reaction 2 hours that is hydrolyzed, and separating step, with embodiment 2, obtains prenol 722mg, yield 67.1%.
Embodiment 8
The trichoroacetic acid(TCA) that is 212 mmoles by 34.7g joins in 2g methyl alcohol, mixes, and makes trichoroacetic acid(TCA) methanol solution; Under room temperature, the sodium trichloroacetate that is 5.0 mmoles by 927mg joins in trichoroacetic acid(TCA) methyl alcohol, be stirred to completely and dissolve, slowly add 1.25 milliliters of i.e. isoprene of 12.5 mmoles, isoprene: trichoroacetic acid(TCA): sodium trichloroacetate mol ratio=1:17:0.4, add speed identical with embodiment 3, reaction times and product separation, with reference to embodiment 3, are collected isopentene trichloroacetic esters cut.In isopentene trichloroacetic esters, add the mixing solutions by 10ml methyl alcohol and 2.5 milliliters of 4mol/L aqueous sodium hydroxide solutions, making pH is 13.4, the reaction 2 hours that is hydrolyzed, and separating step, with embodiment 3, obtains prenol 591mg, yield 54.9%.
Claims (11)
1. a preparation method for prenol, is characterized in that comprising the following steps:
A, at K
avalue is greater than 10 with respect to water
-4organic carboxyl acid and the system that forms of corresponding salt in slowly add isoprene, under room temperature, be constantly stirred to and react completely, extracting and separating goes out prenyl chloride for acetic ester;
The system that described organic carboxyl acid and corresponding salt thereof form is divided into two kinds of situations: the first is that organic acid is liquid, directly uses organic acid to coordinate its organic acid salt compositional system; The second is that organic acid is solid, except organic acid and its organic acid salt, adds dehydrated alcohol or methyl alcohol compositional system, and add-on is so that whole system is liquid;
B, at prenyl chloride, add alkaline alcohol solution in for acetic ester, be at room temperature hydrolyzed, after reacting completely, extracting and separating is removed impurity, obtains prenol.
2. the preparation method of prenol as claimed in claim 1, it is characterized in that: in described steps A, extracting and separating goes out prenyl chloride and refers to for acetic ester: the sodium chloride aqueous solution that is 8-15% with weightmeasurement ratio and the mixed solution of hexane carry out extracting and separating as extraction liquid, obtain prenyl chloride for the hexane solution of acetic ester, this for hexane solution saturated sodium bicarbonate solution, saturated nacl aqueous solution successively each washing once after, add anhydrous magnesium sulfate to remove moisture, hexane is sloughed in underpressure distillation, collect prenyl chloride for acetic ester cut, obtain.
3. the preparation method of prenol as claimed in claim 1, it is characterized in that: after reacting completely in described step B, extracting and separating removal impurity refers to: after hydrolysis finishes, add extraction liquid, isolating organic layer washes with saturated sodium-chloride, anhydrous magnesium sulfate drying, organic solvent is sloughed in decompression, obtains prenol;
Described extraction liquid is the saturated sodium-chloride water solution of 80-120 weight part, and pentane, ether equivalent mixed liquor with 40-80 weight part, mix composition.
4. the preparation method of prenol as claimed in claim 1, is characterized in that:
Described K
avalue is greater than 10 with respect to water
-4organic carboxyl acid and the system of corresponding salt in, the molar ratio of organic carboxyl acid and corresponding salt thereof is 15 ~ 23:0.3 ~ 0.5.
5. the preparation method of prenol as claimed in claim 4, is characterized in that: described isoprene and the mol ratio of organic carboxyl acid are 1:15 ~ 23.
6. the preparation method of prenol as claimed in claim 5, is characterized in that: the molar ratio of described isoprene, organic carboxyl acid and corresponding salt thereof is 1:19 ~ 21:0.35 ~ 0.45.
7. the preparation method of prenol as claimed in claim 1, is characterized in that: described alkaline alcohol solution refers to the alcohol solution that pH is 12-14.
8. the preparation method of prenol as claimed in claim 7, is characterized in that: described alkaline alcohol solution refers to the methanol aqueous solution that pH is the sodium hydroxide of 13-14.
9. the preparation method of prenol according to claim 1, is characterized in that: described organic carboxyl acid is chloracetic acid, oxalic acid.
10. the preparation method of prenol according to claim 9, is characterized in that: the corresponding salt of described organic carboxyl acid is an alkali metal salt of chloracetic acid, oxalic acid.
The preparation method of 11. prenols according to claim 10, is characterized in that: described organic carboxyl acid and corresponding salt thereof are Monochloro Acetic Acid, dichloro acetic acid, trichoroacetic acid(TCA) and corresponding sodium salt or sylvite thereof.
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| CN201410185588.2A CN103922894A (en) | 2014-05-05 | 2014-05-05 | Preparation method of isopentenol |
| CN201410303251.7A CN104086370A (en) | 2014-05-05 | 2014-06-30 | Preparation method of isopentenol |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US5872277A (en) * | 1997-03-10 | 1999-02-16 | Loyola University Of Chicago | Methods for preparing prenyl alcohol |
| US6278016B1 (en) * | 1999-12-09 | 2001-08-21 | Loyola University Of Chicago | Methods for conversion of isoprene to prenyl alcohol and related compounds |
| CN103333065B (en) * | 2013-07-24 | 2015-07-22 | 上海派尔科化工材料有限公司 | Method for continuously producing acetic acid isopentenyl ester |
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Application publication date: 20140716 |