CN108069883A - A kind of production technology of 3,3- dimethyl butyraldehydes - Google Patents
A kind of production technology of 3,3- dimethyl butyraldehydes Download PDFInfo
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- CN108069883A CN108069883A CN201711435291.7A CN201711435291A CN108069883A CN 108069883 A CN108069883 A CN 108069883A CN 201711435291 A CN201711435291 A CN 201711435291A CN 108069883 A CN108069883 A CN 108069883A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/24—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfuric acids
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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
- C07C29/12—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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
- C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
- C07C45/38—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a primary hydroxyl group
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Abstract
The invention belongs to chemosynthesis technical fields, and in particular to a kind of production technology of 3,3 dimethyl butyraldehydes.The technique comprises the following steps successively：S1, with the tert-butyl alcohol, ethylene, for raw material, n-hexane is reaction dissolvent, and sulfuric acid catalysis synthesizes 3,3 dimethylbutyl sulfuric esters；S2, under catalyst action, controlled at 30 DEG C ~ 50 DEG C, hydrolysis obtain 3,3 dimethylbutyl alcohol；S3,3,3 dimethyl butyraldehydes are obtained with polymerization inhibitor 701,3,3 dimethylbutyl alcohol of nitrite tert-butyl catalysis oxidation.The production technology is safe and reliable, at low cost, favorable reproducibility and final product purity are high.
Description
Technical field
The invention belongs to chemosynthesis technical fields, and in particular to the production technology of one kind 3,3- dimethyl butyraldehydes.
Background technology
Neotame N-【N- (3,3- dimethylbutyls)-L- α-aspartoyl】- L-phenylalanine 1- methyl esters is the U.S.
A kind of high intensity sweetner of NutraSweet companies exploitation, it has sugariness high, and heat is low, and stability is high, no cariogenicity etc.
Advantage has huge market potential；And the important intermediate that 3,3- dimethyl butyraldehydes are synthesizing neotames (is disclosed in patent
In US5480668 and US5510508), the market price is expensive, therefore need to find one and not only economical but also single-minded prepare among this
The method of body.
The preparation method of 3,3- dimethyl butyraldehydes has much in the prior art, as patent US4175204 is disclosed bromination
Sodium is used together with allyl chloride, and substituted allyl chloride is in the presence of the sodium bromide of catalytic amount with N, N- dimethyl sulfoxide (DMSO) oxygen
Corresponding aldehyde is melted into, this method can generate the dimethyl sulfide of stench, and environmental pollution is serious；In patent US5994593, disclose
It is hydrolyzed with 1,1-, bis- chloro- 3,3- dimethylbutanes and prepares 3,3- dimethyl butyraldehydes, this method needs high temperature, and exists and eliminate instead
Should, alkene is generated, yield is low, and product is miscellaneous；In patent US5905175, disclose with 1- chlorine 3, the preparation of 3- dimethyl butyrates alkoxide
3,3- dimethyl butyraldehydes, this scheme, which equally exists, needs high temperature；It is public in patent US6825384 and patent WO2005082825
It has opened and has prepared 3,3- dimethyl butyraldehydes with the oxidation of 3.3- diformazans butanol, water consumption is bigger than normal, and sewage quantity is big, causes serious pollution to the environment；
In patent EP0391652 and patent EP0374952,3,3- diformazan butyraldehyde are in dichloromethane solution by 3,3- dimethyl butyrate alcohols
Middle to be prepared with row oxidation in the presence of oxalyl chloride, dimethyl sulfoxide (DMSO) and triethylamine, this method is well-known Swern oxidizing process,
The dimethyl sulfide by-product of stench can be generated, is unfavorable for industrializing.
In addition, the method for also having many patent disclosures preparation 3,3- dimethyl butyraldehydes domestic at present, such as patent
Alcohol is hydrolyzed into using chloro- 3, the 3- dimethylbutanes of 1- in CN200910029947, your gold such as expensive silver oxide reused
Belong to oxidation catalysis to prepare, all low there is efficiency in above-mentioned all synthetic methods, of high cost, pollution is big, poor reproducibility,
Be difficult to realize industrialized production deficiency.If CN102295541A discloses the production technology of one kind 3,3- dimethyl butyraldehydes,
Comprise the following steps：It is raw material to take tertiary butyl chloride and vinylacetate, and catalysis prepares chloro- 3, the 3- dimethyl butyrates yl acetates of 1-,
The weight ratio of tertiary butyl chloride and vinylacetate is 1:0.84 ~ 0.93, under catalyst action, control temperature hydrolysis disproportionation 1-
Chloro- 3,3- dimethyl butyrates yl acetate prepares the hydrolysis disproportionated reaction mixture of the dimethyl butyraldehyde Han 3,3-, and it is pure to carry out rectifying
Change, obtain 3,3- dimethyl butyraldehydes, catalyst is alchlor or p-methyl benzenesulfonic acid or ferric trichloride, and hydrolysis disproportionation temperature is
100℃~110℃.Hydrolysis gasification temperature described in the patent is 100 DEG C ~ 110 DEG C, and energy consumption of reaction is higher, and reactant into
This is higher, so as to influence to make overall industrial cost higher.
The content of the invention
In order to solve the technical issues of above-mentioned, the present invention provides the production technology of one kind 3,3- dimethyl butyraldehydes, the party
Method is safe and reliable, at low cost, favorable reproducibility and final product purity are high.
It is an object of the invention to overcome above-mentioned the deficiencies in the prior art, one kind 3,3- dimethyl butyraldehydes are provided
Production technology, the production technology is safe and reliable, at low cost, favorable reproducibility and final product purity are high.
The present invention is achieved by the following technical solution
The production technology of one kind 3,3-, bis- dimethyl butyraldehydes, which is characterized in that comprise the following steps successively：
S1, with the tert-butyl alcohol, ethylene, for raw material, n-hexane is reaction dissolvent, sulfuric acid catalysis synthesis 3,3- dimethylbutyl sulfuric acid
Ester；
S2, under catalyst action, controlled at 30 DEG C ~ 50 DEG C, hydrolysis obtain 3,3- dimethylbutyl alcohol；
S3,3,3- dimethyl butyraldehydes are obtained with polymerization inhibitor 701, nitrite tert-butyl catalysis oxidation 3,3- dimethylbutyl alcohol.
Net reaction is：
。
Polymerization inhibitor 701 also known as high-efficiency polymerization inhibitor ZM-701, chemical name:2,2,6,6- tetramethyl -4- hydroxy piperidine nitrogen oxygen is certainly
By base (TMHPO), molecular formula: C9H18NO2, molecular weight 172.
In the production technology of above-mentioned 3,3- dimethyl butyraldehydes, the mol ratio of the tert-butyl alcohol and ethylene is in the step S1
1:1.0~1.5。
Preferably, in the production technology of above-mentioned 3,3- dimethyl butyraldehydes, the tert-butyl alcohol and ethylene rubs in the step S1
Your proportioning is 1:1.2.
In the production technology of above-mentioned 3,3- dimethyl butyraldehydes, sulfuric acid and tert-butyl alcohol molar ratio are 1.5 in the step S1:
1。
In the production technology of above-mentioned 3,3- dimethyl butyraldehydes, the concentration of sulfuric acid is mass percent in the step S1
Concentration >=98%.
The production technology of above-mentioned 3,3- dimethyl butyraldehydes, the detailed step of the step S1 is first by n-hexane, uncle
Butanol, sulfuric acid are placed in reaction vessel, ethylene are passed through when being cooled to -5 DEG C ~ 5 DEG C, control temperature is in -5 DEG C ~ 5 DEG C insulation reactions
2 synthesize 3,3- dimethylbutyl sulfuric esters when small.
In the production technology of above-mentioned 3,3- dimethyl butyraldehydes, in the step S2, catalyst is sodium hydroxide or hydrogen-oxygen
Change potassium.
In the production technology of above-mentioned 3,3- dimethyl butyraldehydes, in the step S2, hydrolysis time is 1 ~ 2h.
In the production technology of above-mentioned 3,3- dimethyl butyraldehydes, in the step S3, nitrite tert-butyl, polymerization inhibitor 701
It is 0.5 with 3,3- dimethyl butyrate alcohols molar ratio:0.5:1.
In the production technology of above-mentioned 3,3- dimethyl butyraldehydes, in the step S3, using dichloromethane as solvent, polymerization inhibitor
701 and nitrite tert-butyl be catalyst, oxygen is oxygen source, 0.3 ~ 0.5MPa of pressure control room temperature reactions.
In the production technology of 3, the 3- dimethyl butyraldehydes of the present invention, the reaction solution progress rectifying of step S3 can obtain pure
The 3,3- dimethyl butyraldehydes of degree more than 99.5%.
It in the present invention, is refered in particular to Ru non-, all amounts are unit of weight, and all raw material, equipment can be purchased from market
.
Beneficial effects of the present invention are：
（1）The raw material and reaction process that production technology of the present invention uses have larger difference, the tert-butyl alcohol of selection with the prior art
And ethylene raw, it is cheap to be easy to get, it is high income, environmentally protective, production cost can be reduced；Reaction condition is more mild, is not required to
High temperature is wanted, is had no special requirements to production equipment, production security is high, and product purity is high.
（2）In production technology of the present invention, the reaction temperature of step S1 is -5 ~ 5 DEG C, compared to CN00809749 patent conditions more
It is easy to control and be easily achieved, high income.
（3）Using nitrite tert-butyl, polymerization inhibitor 701 in 25 ~ 40 DEG C of catalysis oxidations, it is catalyzed compared to precious metal high-temperature
260 DEG C or more or sodium hypochlorite catalysis oxidation, it is easier to which productive experiment, sewage quantity smaller are environmentally protective.Production technology of the present invention
Reaction condition is more mild, and high temperature is not required in green, has no special requirements to production equipment, and production security is high, product purity,
High income.
Specific embodiment
The present invention is further described with reference to specific embodiment, so that those skilled in the art knows more about
The present invention, but be not intended to limit the present invention.
Embodiment 1
The production technology of one kind 3,3- dimethyl butyraldehydes, specifically includes following steps：
Step 1 inserts 150 kilograms of n-hexanes, 74 kilograms of tert-butyl alcohols, 147 kilograms of sulfuric acid in reaction kettle, opens stirring and cooling
Cycle, when being cooled to -5 DEG C ~ 5 DEG C, then it is interior when 3 is small be passed through 33.6 kilograms of ethylene gas, at -5 DEG C ~ 5 DEG C after ventilation
When insulation reaction 2 is small；
Step 2, after reaction, 50 kilograms of saturation sodium hydroxide solution is squeezed into reaction kettle, 35 DEG C ~ 40 DEG C of temperature control fully stirs
Mix 2 it is small when, point take organic layer, concentration and recovery n-hexane continues to distill to the greatest extent at 70 DEG C ~ 85 DEG C, collects 140 DEG C ~ 145 DEG C and evaporates
Point, obtain colourless liquid 3,95 kilograms of 3- dimethyl butyrate alcohols；Water is mutually cooled to 0 DEG C ~ 5 DEG C, crystallization recycling sodium sulphate.
Step 3, by 3,3- dimethyl butyrate alcohols 95 kilograms insert in reaction kettle, add in 300 kilograms of dichloromethane, catalyst is sub-
4.8 grams of the nitric acid tert-butyl ester, 701 8.0 grams of polymerization inhibitor, are passed through oxygen to pressure 0.4MPa.Be heated to 30 DEG C reaction 10 it is small when, protect
Temperature reaction terminates, heating distillation, collects 40 DEG C ~ 42 DEG C fractions, and dichloromethane is collected in recycling.Continue to heat up, collect 104 DEG C ~ 106
DEG C obtain 92.2 kilograms of 3,3- dimethyl butyraldehydes, product gas phase purity：99.7%, yield 98%.
Embodiment 2
Step 1 inserts 150 kilograms of n-hexanes, 74 kilograms of tert-butyl alcohols, 118 kilograms of sulfuric acid in reaction kettle, opens stirring and cooling
Cycle, when being cooled to -5 DEG C ~ 5 DEG C, then it is interior when 3 is small be passed through 30.8 kilograms of ethylene gas, at -5 DEG C ~ 5 DEG C after ventilation
When insulation reaction 2 is small；
Step 2, after reaction, 45 kilograms of saturation potassium hydroxide solution is squeezed into reaction kettle, 35 DEG C ~ 40 DEG C of temperature control fully stirs
Mix 2 it is small when, point take organic layer, concentration and recovery n-hexane continues to distill to the greatest extent at 70 DEG C ~ 85 DEG C, collects 140 DEG C ~ 145 DEG C and evaporates
Point, obtain colourless liquid 3,94 kilograms of 3- dimethyl butyrate alcohols；Water is mutually cooled to 0 DEG C ~ 5 DEG C, crystallization recycling potassium sulfate.
Step 3,94 kilograms of 3,3- dimethyl butyrate alcohols are inserted in reaction kettle, add in 300 kilograms of dichloromethane, catalyst nitrous
4.6 grams of tert-butyl acrylate, 701 7.8 grams of polymerization inhibitor, are passed through oxygen to pressure 0.4MPa.Be heated to 30 DEG C reaction 10 it is small when, heat preservation
Reaction terminates, heating distillation, collects 40 DEG C ~ 42 DEG C fractions, and dichloromethane is collected in recycling.Continue to heat up, collect 104 DEG C ~ 106 DEG C
Obtain 91.7 kilograms of 3,3- dimethyl butyraldehydes, product gas phase purity：99.6%, yield 98.5%.
Embodiment 3
Step 1 inserts 150 kilograms of n-hexanes, 74 kilograms of tert-butyl alcohols, 115 kilograms of sulfuric acid in reaction kettle, opens stirring and cooling
Cycle, when being cooled to -5 DEG C ~ 5 DEG C, then it is interior when 3 is small be passed through 32 kilograms of ethylene gas, after ventilation -5 DEG C ~ 5 DEG C guarantor
When temperature reaction 2 is small；
Step 2, after reaction, 44 kilograms of saturation sodium hydroxide solution is squeezed into reaction kettle, 35 DEG C ~ 40 DEG C of temperature control fully stirs
Mix 2 it is small when, point take organic layer, concentration and recovery n-hexane continues to distill to the greatest extent at 70 DEG C ~ 85 DEG C, collects 140 DEG C ~ 145 DEG C and evaporates
Point, obtain colourless liquid 3,94.5 kilograms of 3- dimethyl butyrate alcohols；Water is mutually cooled to 0 DEG C ~ 5 DEG C, crystallization recycling sodium sulphate.
Step 3, by 3,3- dimethyl butyrate alcohols 94.5 kilograms insert in reaction kettle, add in 300 kilograms of dichloromethane, catalyst
4.7 grams of nitrite tert-butyl, 701 8.2 grams of polymerization inhibitor, are passed through oxygen to pressure 0.4MPa.Be heated to 30 DEG C reaction 10 it is small when,
Insulation reaction terminates, heating distillation, collects 40 DEG C ~ 42 DEG C fractions, and dichloromethane is collected in recycling.Continue to heat up, 104 DEG C of collection ~
106 DEG C obtain 91.9 kilograms of 3,3- dimethyl butyraldehydes, product gas phase purity：99.7%, yield 98.2%.
Claims (9)
1. one kind 3, the production technology of 3- dimethyl butyraldehydes, which is characterized in that comprise the following steps successively：
S1, with the tert-butyl alcohol, ethylene, for raw material, n-hexane is reaction dissolvent, sulfuric acid catalysis synthesis 3,3- dimethylbutyl sulfuric acid
Ester；
S2, under catalyst action, controlled at 30 DEG C ~ 50 DEG C, hydrolysis obtain 3,3- dimethylbutyl alcohol；
S3,3,3- dimethyl butyraldehydes are obtained with polymerization inhibitor 701, nitrite tert-butyl catalysis oxidation 3,3- dimethylbutyl alcohol.
2. the production technology of 3,3- dimethyl butyraldehydes according to claim 1, which is characterized in that tertiary fourth in the step S1
The mol ratio of alcohol and ethylene is 1:1.0~1.5.
3. the production technology of 3,3- dimethyl butyraldehydes according to claim 3, which is characterized in that tertiary fourth in the step S1
The mol ratio of alcohol and ethylene is 1:1.2.
4. the production technology of 3,3- dimethyl butyraldehydes according to claim 1, which is characterized in that sulfuric acid in the step S1
It is 1.5 with tert-butyl alcohol molar ratio:1.
5. the production technology of 3,3- dimethyl butyraldehydes according to claim 1, which is characterized in that the step S1's is detailed
Step is passed through ethylene when being cooled to -5 DEG C ~ 5 DEG C, controls for n-hexane, the tert-butyl alcohol, sulfuric acid are placed in reaction vessel first
Temperature synthesizes 3,3- dimethylbutyl sulfuric esters when -5 DEG C ~ 5 DEG C insulation reactions 2 are small.
6. the production technology of 3,3- dimethyl butyraldehydes according to claim 1, which is characterized in that in the step S2, urge
Agent is sodium hydroxide or potassium hydroxide.
7. the production technology of 3,3- dimethyl butyraldehydes according to claim 1, which is characterized in that in the step S2, water
The solution time is 1 ~ 2h.
8. the production technology of 3,3- dimethyl butyraldehydes according to claim 1, which is characterized in that sub- in the step S3
The nitric acid tert-butyl ester, polymerization inhibitor 701 and 3,3- dimethyl butyrate alcohols molar ratio are 0.5:0.5:1.
9. the production technology of 3,3- dimethyl butyraldehydes according to claim 1, which is characterized in that in the step S3, with
Dichloromethane be solvent, polymerization inhibitor 701 and nitrite tert-butyl be catalyst, oxygen is oxygen source, pressure control 0.3 ~ 0.5MPa room temperatures
Reaction.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108794312A (en) * | 2018-07-06 | 2018-11-13 | 南通市常海食品添加剂有限公司 | A kind of method of synthesis 3,3- dimethyl butyraldehydes |
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