CN106748724A - A kind of method for preparing Guerbet acid as raw material with malonate - Google Patents
A kind of method for preparing Guerbet acid as raw material with malonate Download PDFInfo
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- CN106748724A CN106748724A CN201510829265.7A CN201510829265A CN106748724A CN 106748724 A CN106748724 A CN 106748724A CN 201510829265 A CN201510829265 A CN 201510829265A CN 106748724 A CN106748724 A CN 106748724A
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- malonate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C07C51/38—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by decarboxylation
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- Organic Chemistry (AREA)
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- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of method for preparing Guerbet acid as raw material with malonate.The method is：With malonate as raw material, it is alkylated reaction and obtains dialkyl malonate under alkali effect；The foregoing dialkyl malonate for obtaining is hydrolyzed and decarboxylic reaction successively, and Guerbet acid is obtained.The malonate is dimethyl malenate or diethyl malonate.The alkali of the alkylated reaction is selected from one or more in potassium carbonate, NaOH, potassium hydroxide, sodium methoxide, caustic alcohol；The alkylating reagent is the 2-20 alkyl halide of carbon.The present invention uses malonate to prepare Guerbet acid for raw material first, be related to three reactions easily operation, high without HTHP, yield.Alkylated reaction of the present invention, the Guerbet acid main chain and the structure of side chain that can be introduced with flexible modulation, so as to obtain the Guerbet acid of different performance.
Description
Technical field
The present invention relates to the technical field of Guerbet acid preparation technology, and in particular to a kind of with the third two
The method that acid esters prepares Guerbet acid for raw material.
Background technology
Guerbet acid, is a kind of aliphatic acid that alkane of relatively drawing money on credit is carried in carboxylic acid alpha-position.With carbon number phase
With straight chain fatty acid compared with, with colorless and odorless, human body is almost had no adverse effects, freezing point is low,
The features such as excitant is small, in industrial lubricant, metal working fluid, cosmetics, surfactant and auxiliary agent
Etc. aspect have a wide range of applications.
It is prepared by the preparation of Guerbet acid, general oxidation by Guerbet alcohol.Guerbet reaction, be
The reaction of alcohol -ol condensation generation higher alcohols, Guerbet alcohol is both the product of the reaction, is also such alcohol name
The source of title.The title of Guerbet acid is also to go out from this derivative.
CN1266418A Zhong Sha ropes company discloses a kind of heavy metal free and the preparation without soap Guerbet alcohol
Method, product is directly separated by distillation from reactant, without other purge process.CN1436762A
Disclose the preparation method of the Guerbet alcohol of hydroxide and nickel powder mixed catalytic.CN102020533A is public
The Guerbet alcohol preparation method of nano-metal-oxide and highly basic joint catalysis is opened.Above is common
The preparation method of Guerbet alcohol.In the prior art, Ge Er is prepared generally by Guerbet alcohol oxidation
Bert acid.And there is reaction difficulty, corrode big, with serious pollution skill in oxidation reaction in chemical process
Art defect.The other method of Guerbet acid is not prepared by Guerbet alcohol oxidation, there is not yet document
Report.
The content of the invention
It is an object of the present invention to provide a kind of prepare Guerbet acid by raw material of malonate
Method.
The technical scheme that the present invention is used to achieve the above object is as follows：
A kind of to prepare the sour method of Guerbet by raw material of malonate, the method is：With the third two
Acid esters is raw material, and being alkylated reaction under alkali effect obtains dialkyl malonate；Foregoing
To dialkyl malonate be hydrolyzed successively and decarboxylic reaction, be obtained Guerbet acid.
Specific synthetic reaction is referring to following equation 1.
Equation 1
The raw material of the alkylated reaction is malonate (the compound A in equation 1), and this third
Two acid esters can be the R in dimethyl malenate or diethyl malonate, i.e. compound A1
It is methyl or ethyl.Alkali in the alkylated reaction is selected from potassium carbonate, NaOH, hydrogen-oxygen
Change one or more in potassium, sodium methoxide, caustic alcohol；The alkylating reagent is 2-20 carbon
Alkyl halide：Alkyl halide can be alkyl chloride, bromoalkane or idoalkane, and paraffin section is R2With
R3Can be that linear paraffin may also be isoparaffin.
The alkylated reaction, is the step alkylated reaction of an autoclave two, and alkylating reagent can be with identical
Can also be different, to be introduced into two alkyl on malonate methylene (i.e. in compound B
R2And R3).Alkylated reaction solvent for use is selected from methyl alcohol, ethanol, tetrahydrofuran, N, N- diformazans
One kind in base formamide, toluene.The reaction condition of two step alkylated reactions is identical, and each step is equal
It is to add alkali under the conditions of room temperature (i.e. 0-30 DEG C temperature range), is then slowly added into alkylating reagent,
40-150 DEG C is warming up to, is reacted 1-5 hours；Therefore, second step alkylated reaction is needed first
After the completion of step alkylated reaction, cool to room temperature, alkali, Ran Houhuan are added at ambient temperature
Slowly alkylating reagent is added, then is warming up to 40-150 DEG C and reacted.For every step alkylated reaction,
Alkali is 1~2 relative to the molar ratio of malonate:1, alkylating reagent is relative to malonate
Molar ratio is 1~2:1.Alkylated reaction is post-processed：Cooling, removed under reduced pressure solvent is added
In 1mol/L aqueous sulfuric acids and system is 7 or so to pH value, point liquid, organic phase is washed, and is subtracted
Pressure distillation obtains dialkyl malonate (the compound B in equation).
The hydrolysis, can be sour water solution or macromolecule alkali for hydrolysis, acid used selected from sulfuric acid,
One kind in hydrochloric acid, phosphoric acid, acetic acid, or, alkali used is selected from sodium carbonate, potassium carbonate, hydrogen-oxygen
Change the one kind in sodium, potassium hydroxide, the addition of the sour or alkali is dialkyl malonate (change
Compound B) 2-10 times of molar equivalent.Specifically, it is 4mol/L's that can add acid or alkali concn
The aqueous solution.
The hydrolysis uses water as reaction dissolvent, and needs to add a small amount of methyl alcohol or second
Alcohol hydrotropy, methyl alcohol or ethanol are 1/5-1/3 with the volume ratio of water；The hydrolysis, reaction temperature
It it is 50-100 DEG C, the reaction time is 2-12 hours.The post processing of the hydrolysis is：It is cooled to
Room temperature, use in the alkali or aqueous acid of 4mol/L and system to pH value be 1.9 or so, it is quiet
Put, aqueous solution upper strata separates out white solid, filtering, washing, acetone recrystallization obtain final product hydrolysate,
Diacid compounds C.
The decarboxylic reaction is：Diacid compounds C under nitrogen protection, is heated to 110-200 DEG C,
Carbon dioxide is released in reaction, and reaction is stopped when reaction no longer releases gas, that is, Guerbet is obtained
Sour (the compound D in equation 1).
Compared with prior art, beneficial effects of the present invention are as follows：
1, the method present invention firstly discloses Guerbet acid is prepared using malonate is different from
The method of Guerbet alcohol oxidation.
2, the present invention needs not move through oxidation reaction, it is to avoid oxidation reaction is reacted in chemical process
Difficult, big, the with serious pollution technological deficiency of corrosion.
3, alkylated reaction of the present invention, the Guerbet acid main chain that can be introduced with flexible modulation
With the structure of side chain so that obtain different performance Guerbet acid.
4, the present invention prepares be related to three reactions in the method for Guerbet acid, reaction condition all compared with
For gentle, easy to operate without HTHP, yield is high.
5, in many application fields, Guerbet acid needs to obtain milk-toast product, and uses Ge Er
Straight-chain carboxylic acid's impurity of bad smell, purification difficult are typically contained in the product that the oxidation of Bert alcohol is obtained；
And the present invention can remove straight-chain carboxylic acid in two acid phases by recrystallizing, it is ensured that final products are without gas
Taste.
Specific embodiment
Below in conjunction with specific embodiment, the present invention is described in further detail.In following examples
The raw material for being used can be by being commercially available.
Embodiment 1
Under nitrogen protection, by 100g diethyl malonates, 300mL absolute ethyl alcohols input 1000mL
In three neck round bottom flask, at room temperature, 40.5g sodium methoxides are added, then, be slowly added to 102.8g
Bromination of n-butane, adds rear temperature rising reflux, reacts 3h；Room temperature is cooled to, 40.5g first is added
Sodium alkoxide, then, is slowly added to 102.8g bromination of n-butane, temperature rising reflux reaction 3h.Cool to room
Temperature, desolvation, add 1mol/L aqueous sulfuric acids in and system to pH value be 7 or so, organic phase
Washing, vacuum distillation obtain dibutyltin diethyl malonate, 154g (yield 90.6%).
Take 100g dibutyltin diethyl malonates, (NaOH is dense for 550mL sodium hydrate aqueous solutions
It is 4mol/L to spend), 100mL ethanol be added in 1000mL round-bottomed flasks, be heated to reflux 12h,
Room temperature is cooled to, 4mol/L sulphur acid for adjusting pH value to 1.9 or so is added, stood, aqueous solution upper strata
White solid is separated out, filtering, washing, acetone recrystallization obtain final product hydrolysate, dibutyl malonic acid, 75g
(yield 94.4%).
Take in 50g dibutyl malonic acid addition 100mL round-bottomed flasks, under nitrogen protection, be heated to 160 DEG C,
It is reacted to and no longer release gas stopping, cooling obtains final product the acid of ten carbon Guerbets, 38g (yield 95.4%).1H NMR(500MHz,CDCl3) δ=2.34 (CH, 1H, m), 1.62 (CH2,2H,m),1.49(CH2,
2H,m),1.30(CH2,8H,m),0.89(CH3,6H,m)。
Embodiment 2
Under nitrogen protection, by 100g diethyl malonates, 300mL absolute ethyl alcohols input 1000mL
In three neck round bottom flask, at room temperature, 40.5g sodium methoxides are added, then, be slowly added to 102.8g
Bromination of n-butane, adds rear temperature rising reflux, reacts 3h；Room temperature is cooled to, 40.5g first is added
Sodium alkoxide, then, is slowly added to 91.2g chloro n-hexanes, temperature rising reflux reaction 3h.Cool to room
Temperature, desolvation, with system to pH value 7 or so, organic phase water in addition 1mol/L aqueous sulfuric acids
Wash, vacuum distillation obtains 2- butyl -2- hexyl diethyl malonates, 167g (yield 89.1%).
Take 100g 2- butyl -2- hexyls diethyl malonate, 500mL sodium hydrate aqueous solutions
(4mol/L), 100mL ethanol are added in 1000mL round-bottomed flasks, are heated to reflux 12h, drop
Temperature adds 4mol/L sulphur acid for adjusting pH value to 1.9 or so to room temperature, stands, and is chromatographed on the aqueous solution
Go out white solid, filtering, washing, acetone recrystallization obtain final product hydrolysate, 2- butyl -2- hexyl malonic acid,
77g (yield 94.7%).
Take 50g 2- butyl -2- hexyls butylmalonic acid add 100mL round-bottomed flasks in, nitrogen protection under,
170 DEG C are heated to, are reacted to and no longer release gas stopping, cooling obtains final product the acid of 12 carbon Guerbets, 39g
(yield 95.2%).1H NMR(500MHz,CDCl3) δ=2.33 (CH, 1H, m), 1.61 (CH2,2H,
m),1.48(CH2,2H,m),1.29(CH2,12H,m),0.88(CH3,6H,m)。
Embodiment 3
Under nitrogen protection, by 100g diethyl malonates, 300mL absolute ethyl alcohols input 1000mL
In three neck round bottom flask, at room temperature, 40.5g sodium methoxides are added, then, be slowly added to 91.2g chlorine
For n-hexane, rear temperature rising reflux is added, react 3h；Room temperature is cooled to, 40.5g methyl alcohol is added
Sodium, then, is slowly added to 91.2g chloro n-hexanes, temperature rising reflux reaction 3h.Cool to room temperature,
Desolvation, with system to pH value 7 or so in addition 1mol/L aqueous sulfuric acids, organic phase washing,
Vacuum distillation obtains dihexyl diethyl malonate, 184g (yield 89.7%).
Take 100g dihexyls diethyl malonate, 450mL sodium hydrate aqueous solutions (4mol/L),
100mL ethanol is added in 1000mL round-bottomed flasks, is heated to reflux 12h, cools to room temperature,
4mol/L sulphur acid for adjusting pH value to 1.9 or so is added, is stood, aqueous solution upper strata separates out white solid,
Filtering, washing, acetone recrystallization obtain final product hydrolysate, dihexyl malonic acid, 80g (yield 96.5%).
Take in 50g dihexyls butylmalonic acid addition 100mL round-bottomed flasks, under nitrogen protection, be heated to
170 DEG C, it is reacted to and no longer release gas stopping, the acid of 14 carbon Guerbets is obtained final product after cooling, 40g (is produced
Rate 95.4%).1H NMR(500MHz,CDCl3) δ=2.33 (CH, 1H, m), 1.60 (CH2,2H,m),
1.46(CH2,2H,m),1.28(CH2,16H,m),0.87(CH3,6H,m)。
Part preferred embodiment of the invention is above are only, the present invention is not limited in the interior of embodiment
Hold.To those skilled in the art, can in the concept of technical solution of the present invention
To have various change and change, any change and change made, the scope of the present invention it
It is interior.
Claims (10)
1. a kind of to prepare the sour method of Guerbet by raw material of malonate, the method comprises the following steps：
Step 1, with malonate as raw material, under alkali effect being alkylated reaction obtains dialkyl group the third two
Acid esters；
Step 2, the foregoing dialkyl malonate for obtaining is hydrolyzed and decarboxylic reaction successively, and Ge Er is obtained
Bert acid.
It is 2. a kind of as claimed in claim 1 to prepare the sour method of Guerbet by raw material of malonate,
It is characterized in that：The malonate is dimethyl malenate or diethyl malonate.
It is 3. a kind of as claimed in claim 1 to prepare the sour method of Guerbet by raw material of malonate,
It is characterized in that：The alkali of the alkylated reaction is selected from potassium carbonate, NaOH, potassium hydroxide, methyl alcohol
One or more in sodium, caustic alcohol；The alkylating reagent is the 2-20 alkyl halide of carbon.
It is 4. a kind of as claimed in claim 3 to prepare the sour method of Guerbet by raw material of malonate,
It is characterized in that：The alkyl halide is alkyl chloride or bromoalkane or idoalkane, and wherein paraffin section is straight chain
Alkane or isoparaffin.
It is 5. a kind of as claimed in claim 3 to prepare the sour method of Guerbet by raw material of malonate,
It is characterized in that：The alkylated reaction uses the step alkylated reaction of an autoclave two, solvent for use to be selected from first
One kind in alcohol, ethanol, tetrahydrofuran, DMF, toluene, two step alkylated reactions
The alkylating reagent of use is identical or different.
6. a kind of sour as raw material prepares Guerbet with malonate as described in claim any one of 1-5
Method, it is characterised in that the reaction condition of the alkylated reaction is：Added under the conditions of 0-30 DEG C
Alkali, is then slowly added into alkylating reagent, is warming up to 40-150 DEG C, reacts 1-5 hours；Alkali relative to
The molar ratio of malonate is 1~2:1, alkylating reagent is relative to the molar ratio of malonate
1~2:1.
It is 7. a kind of as claimed in claim 1 to prepare the sour method of Guerbet by raw material of malonate,
It is characterized in that：The hydrolysis of the dialkyl malonate is anti-using acid hydrolytic reaction or basic hydrolysis
Should；Acid used is selected from sodium carbonate, carbon selected from the one kind in sulfuric acid, hydrochloric acid, phosphoric acid, acetic acid, alkali used
One kind in sour potassium, NaOH, potassium hydroxide, the acid or alkali addition are dialkyl malonate
2~10 times of molar equivalents.
8. as described in claim 1 or 7 it is a kind of with malonate as raw material prepare Guerbet acid side
Method, it is characterised in that：The hydrolysis uses water as reaction dissolvent, and adds a small amount of methyl alcohol or second
Alcohol hydrotropy, the methyl alcohol or ethanol are 1 with the volume ratio of water:5~1:3.
It is 9. a kind of as claimed in claim 8 to prepare the sour method of Guerbet by raw material of malonate,
It is characterized in that：The reaction temperature of the hydrolysis is 50~100 DEG C, and the reaction time is 2~12 hours；
Reaction is lowered the temperature after terminating, and it is 1.8~2.0 to pH value to add alkali or sour neutralization system, is stood, the aqueous solution
Upper strata separates out white solid, and filtering, washing, acetone recrystallization obtain final product hydrolysate.
It is 10. a kind of as claimed in claim 1 to prepare the sour method of Guerbet by raw material of malonate,
It is characterized in that：The hydrolysate obtained after dialkyl malonate hydrolysis under nitrogen protection, plus
Heat carries out decarboxylic reaction to 110~200 DEG C, and carbon dioxide is released in reaction, is stopped when reaction no longer releases gas
Only react.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108358783A (en) * | 2018-04-13 | 2018-08-03 | 华烁科技股份有限公司 | The preparation method of 3- substituent glutaric acids diester and glutaconate diester |
| CN111269083A (en) * | 2020-02-24 | 2020-06-12 | 珠海市柏瑞医药科技有限公司 | Synthesis method of Guerbet acid |
| CN113563180A (en) * | 2021-07-26 | 2021-10-29 | 广东嘉博制药有限公司 | (E) Preparation method of (E) -4-ene-1, 8-octanedioic acid |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102241582A (en) * | 2010-05-10 | 2011-11-16 | 山东方明药业股份有限公司 | Synthesis technology of sodium valproate |
| CN102267897A (en) * | 2010-08-02 | 2011-12-07 | 重庆兰科化工有限责任公司 | Preparation method of malonate |
| CN102417553A (en) * | 2011-09-29 | 2012-04-18 | 长沙新宇高分子科技有限公司 | Hydroxyalkyl aryl ketone photoinitiator capable of reducing volatile organic compound (VOC) discharge until elimination of VOC discharge |
-
2015
- 2015-11-25 CN CN201510829265.7A patent/CN106748724A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102241582A (en) * | 2010-05-10 | 2011-11-16 | 山东方明药业股份有限公司 | Synthesis technology of sodium valproate |
| CN102267897A (en) * | 2010-08-02 | 2011-12-07 | 重庆兰科化工有限责任公司 | Preparation method of malonate |
| CN102417553A (en) * | 2011-09-29 | 2012-04-18 | 长沙新宇高分子科技有限公司 | Hydroxyalkyl aryl ketone photoinitiator capable of reducing volatile organic compound (VOC) discharge until elimination of VOC discharge |
Non-Patent Citations (1)
| Title |
|---|
| OLEKSANDR POKHOLENKO ET AL: "Lipid oligonucleotide conjugates as responsive nanomaterials for drug delivery", 《JOURNAL OF MATERIAL CHEMISTRY B》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108358783A (en) * | 2018-04-13 | 2018-08-03 | 华烁科技股份有限公司 | The preparation method of 3- substituent glutaric acids diester and glutaconate diester |
| CN108358783B (en) * | 2018-04-13 | 2021-04-06 | 华烁科技股份有限公司 | 3-substituted glutaric diester and preparation method of glutaconic diester |
| CN111269083A (en) * | 2020-02-24 | 2020-06-12 | 珠海市柏瑞医药科技有限公司 | Synthesis method of Guerbet acid |
| CN111269083B (en) * | 2020-02-24 | 2023-08-25 | 珠海市柏瑞医药科技有限公司 | Synthesis method of guerbet acid |
| CN113563180A (en) * | 2021-07-26 | 2021-10-29 | 广东嘉博制药有限公司 | (E) Preparation method of (E) -4-ene-1, 8-octanedioic acid |
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Application publication date: 20170531 |