CN108586516A - A kind of preparation method of carbamate groups alkoxy silane and isocyanate alkoxysilane - Google Patents
A kind of preparation method of carbamate groups alkoxy silane and isocyanate alkoxysilane Download PDFInfo
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- CN108586516A CN108586516A CN201810587039.6A CN201810587039A CN108586516A CN 108586516 A CN108586516 A CN 108586516A CN 201810587039 A CN201810587039 A CN 201810587039A CN 108586516 A CN108586516 A CN 108586516A
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- Prior art keywords
- alkoxy silane
- preparation
- carbamate groups
- chloropropyl
- silane
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
- C07F7/121—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20
- C07F7/127—Preparation or treatment not provided for in C07F7/14, C07F7/16 or C07F7/20 by reactions not affecting the linkages to the silicon atom
Abstract
This application involves a kind of preparation method of carbamate groups alkoxy silane and a kind of preparation methods of isocyanate alkoxysilane.Specifically, the application uses environment-protecting and non-poisonous raw material carbamate and chloropropyl alkoxy silane synthesis of carbamates base alkoxy silane first, then carbamate groups alkoxy silane is cracked in a mild condition, obtains isocyanate alkoxysilane.The advantageous effect of the application is that synthesis route is simple, belongs to green clean manufacturing mode.Raw material carbamate is non-toxic organic compound, is easy to transport and store, No leakage.This reaction condition is mild, and reaction process is corrosion-free to equipment, environmentally safe.It is generated without solid and other wastes in cracking process, it is easily operated.
Description
Technical field
This application involves organic compound synthesis technical fields, and specifically, this application involves a kind of carbamate groups
The preparation method of alkoxy silane and isocyanate alkoxysilane.
Background technology
Isocyanate alkoxysilane is mainly used in silane fluid sealant and modified polyurethane resin.It is passed in isocyanates
In the synthesis technology of system, phosgenation uses more.It is early both at home and abroad to have been reported that, prepare isocyanide using aminated compounds and phosgene reaction
Acid esters.However phosgenation technical sophistication, raw material severe toxicity generate a large amount of eroding chemical, such as HCl, chlorine etc., to environment dirt
Dye is serious.With being increasingly enhanced for environmental requirement, exploitation non-phosgene becomes the very important direction of chemical field.
China Patent Publication No. is that the patent document of CN1631893A discloses a kind of preparation method, using amino silane and
Carbonic ester is raw material, and the mixture of the silylorganocarbamate containing silicon substrate is generated under basic catalyst effect, is neutralized with acid laggard
Row filtering, finally carries out rectification under vacuum cracking at a temperature of 100-200 DEG C to filtrate, and isocyanate group alkoxyl silicone is made
Alkane.
China Patent Publication No. is that the patent document of CN 101161657A discloses another preparation method, with amido silicon
Alkane is raw material with carbonyl dimidazoles, under the action of catalyst, isocynate silane coupling agent is made in organic solvent.
China Patent Publication No. is that the patent No. of CN101307067A discloses a kind of preparation method, with carbamate groups
Alkoxy silane is raw material, and after adjustment pH is 0-7, normal pressure thermal cracking is obtained containing alcohol, amino at a temperature of 300-500 DEG C
The mixture of formic acid ester group alkoxy silane and isocyanate alkoxysilane, then said mixture is evaporated under reduced pressure simultaneously
Fraction is collected, isocyanate alkoxysilane is obtained.
In above-mentioned synthetic method, first method generates solid salt waste, and second method uses expensive carbonyl two
The cracking temperature of imidazoles, the third method is excessively high.For this purpose, this field is mild there is still a need for a kind of environmental protection, reaction condition is developed
The method of synthesizing isocyanate base alkoxy silane.
Invention content
A kind of preparation method for being designed to provide carbamate groups alkoxy silane of the application and a kind of isocyanic acid
The preparation method of ester group alkoxy silane, to solve above-mentioned the problems of the prior art.Specifically, the application uses first
Environment-protecting and non-poisonous raw material carbamate and chloropropyl alkoxy silane synthesis of carbamates base alkoxy silane, then in temperature
Carbamate groups alkoxy silane is cracked under the conditions of, obtains isocyanate alkoxysilane.
To achieve the goals above, the application provides following technical proposals.
In the first aspect, the application provides a kind of preparation method of carbamate groups alkoxy silane, the method
At a temperature of being included in 90-150 DEG C, so that carbamate is reacted the predetermined time with chloropropyl alkoxy silane, obtained after purification
Colourless or light yellow clarifying liquid body carbamate groups alkoxy silane.
In a kind of embodiment of first aspect, the carbamate has by being tied shown in the following general formula (I)
Structure:
Wherein, R1For saturated alkyl group, carbon chain lengths C1-C6。
In a kind of embodiment of first aspect, the chloropropyl alkoxy silane, which has, passes through the following general formula (II) institute
The structure shown:
Cl-(CH2)3-SiX(3-a)R2 a
Logical formula (II),
Wherein, R2It is saturated alkyl, carbon chain lengths C1-C6;The integer that a is 0 to 3;X is saturation alkoxy base,
Carbon chain lengths are C1-C6。
In a kind of embodiment of first aspect, the carbamate groups alkoxy silane, which has, passes through the following general formula
(III) structure shown in:
Wherein, R1For saturated alkyl group, carbon chain lengths C1-C6;R2It is saturated alkyl, carbon chain lengths C1-C6;a
For 0 to 3 integer;X is saturation alkoxy base, carbon chain lengths C1-C6。
In a kind of embodiment of first aspect, the carbamate is methyl carbamate or urethane
Ester.
In a kind of embodiment of first aspect, the chloropropyl alkoxy silane be r-chloropropyl trimethoxyl silane,
One kind in chloropropyl triethoxysilane, chloropropylmethyldimethoxysilane and chloropropyl ethyl diethoxy silane.
In a kind of embodiment of first aspect, the carbamate is reacted with the chloropropyl alkoxy silane
It is carried out in anhydrous or low moisture (biodiversity content is less than 0.1%) environment.
In a kind of embodiment of first aspect, chloropropyl alkoxy silane is added dropwise by constant pressure funnel.
In a kind of embodiment of first aspect, the molar ratio of the carbamate and chloropropyl alkoxy silane is
1∶10-10∶1。
In second aspect, the application provides a kind of preparation method of isocyanate alkoxysilane, the method packet
It includes under the action of catalyst, at a temperature of 100-200 DEG C, to passing through carbamate groups alkoxy as described in relation to the first aspect
Carbamate groups alkoxy silane prepared by the preparation method of silane is evaporated under reduced pressure, and isocyanate group alkoxy is obtained
Silane.
In a kind of embodiment of second aspect, in vacuum distillation process, vacuum degree 0-100mmHg.
In a kind of embodiment of second aspect, vacuum distillation used catalyst is metal or metal oxide, organic
One kind in sulfonate or silicon class compound.
In a kind of embodiment of second aspect, the metallic catalyst includes iron powder, zinc powder or glass putty.
Compared with prior art, the advantageous effect of the application is that the process route of the application is simple, belongs to green cleaning
The mode of production.Raw material carbamate is non-toxic organic compound, is easy to transport and store, No leakage.This reaction condition temperature
With reaction process is corrosion-free to equipment, environmentally safe.It is generated without solid and other wastes in cracking process, it is easily operated.
Description of the drawings
Fig. 1 shows the infared spectrum of the isocyanate group propyl trimethoxy silicane according to embodiment 1.
Fig. 2 shows the infared spectrum of the isocyanate group propyl-triethoxysilicane according to embodiment 2.
Specific implementation mode
Unless otherwise indicated, from context cues or belong to the convention of the prior art, otherwise number all in the application
It is all based on weight with percentage, and test and characterizing method used is all synchronous with the submission date of the application.It is being applicable in
In the case of, any patent, patent application or disclosure involved in the application are fully incorporated in this as reference, and its
Patent families of equal value are also introduced into as reference, disclosed by these special documents about the synthetic technology in this field, product
With the definition of fabrication design, polymer, comonomer, initiator or catalyst etc..If the specific art disclosed in the prior art
Defining for language is inconsistent with any definition provided herein, then term provided herein of being subject to defines.
Digital scope in the application is approximation, therefore unless otherwise stated, it may include the number other than range
Value.Numberical range include with the increased all numerical value from lower limiting value to upper limit value of 1 unit, condition be any lower value with
There are the intervals of at least two unit between arbitrary high value.For example, if compositional, physics or other property (such as molecules
Amount, melt index (MI) etc.) it is 100 to 1000, it is meant that clearly list all single numbers, such as 100,101,102 etc., with
And all subranges, such as 100 to 166,155 to 170,198 to 200 etc..For comprising less than 1 numerical value or comprising big
In the range of 1 score (such as 1.1,1.5 etc.), then suitably regard 1 unit as 0.0001,0.001,0.01 or 0.1.
For including the range of the units less than 10 (such as 1 to 5), usually regarding 1 unit as 0.1., these are only intended to table
The specific example of the content reached, and all possible combination of the numerical value between cited minimum and peak is all recognized
In this application for clear record.Numberical range in the application particularly provides various comonomers in acrylate copolymer
In content, content of the various components in photoetching compositions, temperature and these components when acrylic ester synthesizing it is each
Kind feature and property.
About chemical compound in use, unless explicitly stated otherwise, otherwise odd number includes all isomeric forms, otherwise also
So (for example, " hexane " either individually or collectively includes whole isomers of hexane).In addition, unless explicitly stated otherwise, otherwise using "
One ", the noun that " one kind " or " being somebody's turn to do " is described also includes its plural form.
Term " includes " that " including ", " having " and their derivative are not excluded for any other component, step or mistake
The presence of journey, and whether disclose in this application with these other components, step or process unrelated.To eliminate any query,
Unless expressly stated, otherwise all using term " including ", " including " in the application, or the composition of " having " can include to appoint
What additional additive, auxiliary material or compound.On the contrary, in addition to necessary to operating characteristics those, term " substantially by ...
Composition " excludes any other component, step or process except the hereinafter described range of any term.Term " by ...
Composition " does not include any component, step or the process for not specifically describing or listing.Unless expressly stated, otherwise term " or " refer to
The separate member listed or any combination thereof.
In a specific embodiment, the present invention proposes a kind of new process of synthesizing isocyanate base alkoxy silane
Method.The method is free from environmental pollution, belongs to a kind of clean preparation method.
The cardinal principle of the method for the invention is as follows:
The method is broadly divided into two steps:(a) using carbamate and chloropropyl alkoxy silane as raw material, under certain temperature
The mixture of carbamate groups alkoxy silane and carbamate hydrochloride is obtained by the reaction, filtering salinity obtains colourless or shallow
Yellow clarified solution body carbamate groups alkoxy silane.(b) under the action of catalyst, decompression essence is carried out to above-mentioned supernatant liquid
It evaporates, obtains product isocyanate alkoxysilane.
Reaction equation is as follows:
In above formula (a) (b):R1For saturated alkyl group, carbon chain lengths C1-C6;R2It is saturated alkyl, carbon chain lengths
For C1-C6;A is 0-3 integers;X is saturation alkoxy base, carbon chain lengths C1-C6。
Carbamate described in above-mentioned steps (a) is one kind in methyl carbamate, urethanes.
Chloropropyl alkoxy silane described in above-mentioned steps (a) is r-chloropropyl trimethoxyl silane, three ethoxy of chloropropyl
One kind in base silane, chloropropylmethyldimethoxysilane and chloropropyl ethyl diethoxy silane.
Chloropropyl alkoxy silane meets water facile hydrolysis in above-mentioned steps (a), so carbamate and chloropropyl alkoxy
The reaction of silane need to be maintained at an anhydrous or low moisture environment (≤0.1%).
Chloropropyl alkoxy silane selection constant pressure funnel is added dropwise in above-mentioned steps (a), time for adding 1-3h.
The molar ratio of carbamate and chloropropyl alkoxy silane described in above-mentioned steps (a) is 1: 10-10: 1.Instead
It is 90-150 DEG C to answer temperature, reaction time 1-10h.
Vacuum distillation condition described in above-mentioned steps (b) is:100-200 DEG C of temperature, vacuum degree 0-100mmHg.
Vacuum distillation used catalyst described in above-mentioned steps (b) is metal or metal oxide (iron powder, zinc powder, tin
Class), one kind in organic sulfonate or silicon class compound.
Embodiment
Below in conjunction with embodiment, the invention will be further described
Embodiment 1
Methyl carbamate 75g is weighed, is added to thermometer, condenser pipe, the low liquid funnel of constant pressure and churned mechanically
In four-hole boiling flask, it is heated to 60 DEG C of meltings.It is passed through inert gas at this temperature, r-chloropropyl trimethoxyl silane 198g is added dropwise,
Time for adding about 2h.After being added dropwise, it is warming up to 120 DEG C of heat preservation 3h.Cooling and control mixing speed, will be in obtained mixture
Solid salt is removed by filtration, and obtains clear filtrate, and using iron powder as catalyst, rectification under vacuum is collected 120 DEG C/20mmHg and evaporated
Divide 155g.By infrared spectrum analysis, as shown in Figure 1, there is strong and point absorption peak at 2210-2276cm-1, show to synthesize
Isocyanate group propyl trimethoxy silicane.
Embodiment 2
Methyl carbamate 150g is weighed, is added to thermometer, condenser pipe, the low liquid funnel of constant pressure and churned mechanically
In four-hole boiling flask, it is heated to 60 DEG C of meltings.It is passed through inert gas at this temperature, chloropropyl triethoxysilane 99g, drop is added dropwise
About 1.5h between added-time.After being added dropwise, it is warming up to 120 DEG C of heat preservation 3h.Cooling and control mixing speed, will be in obtained mixture
Solid salt is removed by filtration, and obtains clear filtrate, and using zinc powder as catalyst, rectification under vacuum is collected 130 DEG C/20mmHg and evaporated
Divide 70g.By infrared spectrum analysis, as shown in Fig. 2, there is strong and point absorption peak at 2210-2276cm-1, show synthesis
Isocyanate group propyl-triethoxysilicane.
Embodiment 3
Urethanes 30g is weighed, is added to thermometer, condenser pipe, the low liquid funnel of constant pressure and churned mechanically
In four-hole boiling flask, it is heated to 60 DEG C of meltings.It is passed through inert gas at this temperature, r-chloropropyl trimethoxyl silane 162g is added dropwise,
Time for adding about 2h.After being added dropwise, it is warming up to 120 DEG C of heat preservation 3h.Cooling and control mixing speed, will be in obtained mixture
Solid salt is removed by filtration, and obtains clear filtrate, and using iron powder as catalyst, rectification under vacuum is collected 120 DEG C/20mmHg and evaporated
Divide 140g.It is as a result similar to Example 1 by infrared spectrum analysis, there is strong and point absorption peak at 2210-2276cm-1,
Show to have synthesized isocyanate group propyl trimethoxy silicane.
The above-mentioned description to embodiment is that this Shen can be understood and applied for the ease of those skilled in the art
Please.Person skilled in the art obviously easily can make various modifications to these embodiments, and described herein
General Principle is applied in other embodiments without paying performing creative labour.Therefore, the application is not limited to implementation here
Example, those skilled in the art make according to herein disclosed content in the case where not departing from the application scope and spirit
It improves and changes within all scope of the present application.
Claims (10)
1. a kind of preparation method of carbamate groups alkoxy silane, the method includes at a temperature of 90-150 DEG C, making
Carbamate reacts the predetermined time with chloropropyl alkoxy silane, and colourless or light yellow clarifying liquid body amino first is obtained after purification
Perester radical alkoxy silane.
2. the preparation method of carbamate groups alkoxy silane as described in claim 1, which is characterized in that the amino first
Acid esters has through structure shown in the following general formula (I):
Wherein, R1For saturated alkyl group, carbon chain lengths C1-C6;And/or
The chloropropyl alkoxy silane has through structure shown in the following general formula (II):
Cl-(CH2)3-SiX(3-a)R2 aLogical formula (II),
Wherein, R2It is saturated alkyl, carbon chain lengths C1-C6;The integer that a is 0 to 3;X is saturation alkoxy base, carbochain
Length is C1-C6;And/or
The carbamate groups alkoxy silane has through structure shown in the following general formula (III):
Wherein, R1For saturated alkyl group, carbon chain lengths C1-C6;R2It is saturated alkyl, carbon chain lengths C1-C6;A arrives for 0
3 integer;X is saturation alkoxy base, carbon chain lengths C1-C6。
3. the preparation method of carbamate groups alkoxy silane as described in claim 1, which is characterized in that the amino first
Acid esters is methyl carbamate or urethanes.
4. the preparation method of carbamate groups alkoxy silane as described in claim 1, which is characterized in that the chloropropyl
Alkoxy silane is r-chloropropyl trimethoxyl silane, chloropropyl triethoxysilane, chloropropylmethyldimethoxysilane and chlorine
One kind in ethyl diethoxy silane.
5. the preparation method of carbamate groups alkoxy silane as described in claim 1, which is characterized in that the amino first
Acid esters is carried out with reacting for the chloropropyl alkoxy silane in low moisture environment.
6. the preparation method of carbamate groups alkoxy silane as described in claim 1, which is characterized in that chloropropyl alcoxyl
Base silane is added dropwise by constant pressure funnel.
7. the preparation method of carbamate groups alkoxy silane as described in claim 1, which is characterized in that the amino first
The molar ratio of acid esters and chloropropyl alkoxy silane is 1: 10-10: 1.
8. a kind of preparation method of isocyanate alkoxysilane, the method includes under the action of catalyst, in 100-200
At a temperature of DEG C, to the preparation method by the carbamate groups alkoxy silane as described in any one of claim 1-7
Prepared carbamate groups alkoxy silane is evaporated under reduced pressure, and isocyanate alkoxysilane is obtained.
9. the preparation method of isocyanate alkoxysilane as claimed in claim 8, which is characterized in that be evaporated under reduced pressure
Cheng Zhong, vacuum degree 0-100mmHg.
10. the preparation method of isocyanate alkoxysilane as claimed in claim 8, which is characterized in that vacuum distillation institute
It is one kind in metal or metal oxide, organic sulfonate or silicon class compound with catalyst.
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Cited By (2)
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CN113292591A (en) * | 2021-06-23 | 2021-08-24 | 唐山三孚新材料有限公司 | Synthesis method and application of 1, 3-bis (isocyanatoalkyl) -1,1,3, 3-tetramethyldisiloxane |
CN115353668A (en) * | 2022-07-28 | 2022-11-18 | 广西新晶科技有限公司 | Halogen-free smoke-suppression type flame retardant and preparation method thereof |
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