CN106495977A - A kind of method that utilization micro passage reaction prepares Parylene monomeric compound - Google Patents
A kind of method that utilization micro passage reaction prepares Parylene monomeric compound Download PDFInfo
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- CN106495977A CN106495977A CN201610792280.3A CN201610792280A CN106495977A CN 106495977 A CN106495977 A CN 106495977A CN 201610792280 A CN201610792280 A CN 201610792280A CN 106495977 A CN106495977 A CN 106495977A
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- 0 C*(C)(C)CC(C1)C(Cl)=CC(CCl)=C1Cl Chemical compound C*(C)(C)CC(C1)C(Cl)=CC(CCl)=C1Cl 0.000 description 1
- IYYRATPIHPKFDZ-UHFFFAOYSA-N C[Si+](C)(C)Cc1ccc(CBr)cc1 Chemical compound C[Si+](C)(C)Cc1ccc(CBr)cc1 IYYRATPIHPKFDZ-UHFFFAOYSA-N 0.000 description 1
- YIRCYEYOTWXQSS-UHFFFAOYSA-N C[SiH](C)CC1C(Cl)=CC(CCl)=CC1 Chemical compound C[SiH](C)CC1C(Cl)=CC(CCl)=CC1 YIRCYEYOTWXQSS-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
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Abstract
The invention discloses a kind of method that utilization micro passage reaction prepares Parylene monomeric compound, the method includes the steps such as preheating, synthetic intermediate, synthetic product, oil-water separation, purification, Parylene material monomer compound is prepared in continuous micro passage reaction, have low cost, energy consumption is little, the three wastes are few, continuously controllable, without enlarge-effect the features such as, can be simple etc. than amplifying according to needs of production.
Description
Technical field
The invention belongs to macromolecule synthesising technology field, and in particular to one kind prepares Parylene list using micro passage reaction
The method of body compound.
Background technology
Parylene, Pai Lalun (Parylene) are a kind of protectiveness macromolecular materials, are the middle 1960s U.S.
A kind of molecular level of Union Carbide Corporation's exploitation applies type coating material, is unique Parylene (poly-P-
Xylylene) the adopted name of series of polymers, and uniquely a kind of solids coating in 105D military standard 105D.Parylene uses vacuum
Gas-phase deposition forms protecting film, and this thin film has the features such as thickness is uniform, densification is pin-free, transparent unstressed, has excellent
Different electrical insulating property and protective.Such product is widely used to electronics industry, bio-medical equipment, historical relic, archives and mark
The protection in this grade field.
At present, the Parylene material that widely commercially applies has Parylene (Parylene N), a poly- chloro pair
Dimethylbenzene (Parylene C), poly- dichloro- xylol (Parylene D) and polytetrafluoro are for xylol (Parylene F)
Deng their difference for differring primarily in that substituent group species or substituent group quantity on molecule, so as to determine in heat stability
With the difference in terms of insulating properties.Parylene material is to be pyrolyzed by the monomer xylol cyclodimerization body of different structure under vacuo
And vapor deposition polymerization is into Parylene series polymer, conventional monomer has N-type (xylol cyclodimerization body), C
Type (a chloro-p-xylene cyclodimerization body), D types (dichloro-p-xylene cyclodimerization body) and F types (tetrafluoro xylol cyclodimerization
Body) etc..
Parylene monomers
With the continuous expansion that Parylene material is applied in every field, Parylene monomer xylol cyclodimerization body class
The synthesis of compound has great importance to the preparation and application of Parylene material.Currently, tradition prepares xylol ring two
The method of aggressiveness class compound generally has two classes.A kind of earliest Pintsch process cyclization for being directly to adopt xylol class substrate
Obtain, the temperature needed for this method is higher, generally require 750 DEG C～1000 DEG C, side reaction is a lot, general 30% left side of yield
Right；The method energy consumption is high, and yield is low, and seldom, the xylene substrate containing substituent group is difficult to use the method applicable substrate
Produce corresponding dimer (Nature, 1949,915；Chemistry Letter, 1990, vol.6,893-896), at present
Substantially xylol cyclodimerization body class compound is produced using the method again without enterprise.Now relatively conventional production method is
Cross hofmann elimination to obtain.The method carries out hofmann elimination by heating to methyl-benzyl quaternary ammonium salt monomer
Prepare xylol cyclodimerization body.Such method is due to being water-oil phase reaction, it is generally difficult to realize the fully mixed of reaction system
Splice grafting is touched, although reaction temperature lowers significantly, but yield offer is not obvious.For problems, after in United States Patent (USP) Shen
There please be open disclosure by interpolation DMSO, U.S. Patent application US4806702 to add crown ether or polyethers in US4532369, and or
Person promotes the reaction of two-phase system to enter by adding the materials such as accelerator or phase transfer catalysis such as the quaternary ammonium fluoride salt of document report
Journey, improves yield.Although compared with high-temperature cracking method, reaction temperature is substantially reduced such method, yield has reached medium level
(highest 75% or so), but its reaction system be typically all batch production in traditional tank reactor, the production cycle compared with
Long, typically will be more than 24 hours, it is impossible to realize continuous production, energy requirements are big, low production efficiency；Due to adding in production process
Multiple catalysts, follow-up refined difficulty；Solvent usage amount is big aborning, and the corresponding three wastes for producing are also a lot.
Under Green Development background, a kind of continuous, efficient, Parylene monomeric compound producer of energy-saving and environmental protection is developed
Formula is significant.
Content of the invention
In order to overcome the deficiencies in the prior art, it is an object of the invention to provide a kind of prepare group using micro passage reaction
The method of Rayleigh monomeric compound, prepares Parylene material monomer compound in continuous micro passage reaction, with low cost,
Energy consumption is little, the three wastes are few, continuously controllable, without enlarge-effect the features such as, simple can be waited than amplifying according to needs of production.
For solving the above problems, the technical solution adopted in the present invention is as follows：
A kind of method that utilization micro passage reaction prepares Parylene monomeric compound, the method are comprised the following steps：
1) preheat：The solution of raw material trimethylamine aqueous solution, the compound with structure formula I is each preheating to reaction temperature
Degree；
Wherein R is halogen, p-methyl benzenesulfonic acid base, the one kind in Loprazolam base, X1、X2、X3、X4For H, F, Cl,
One kind in Br, I；
2) synthetic intermediate：Above-mentioned two kinds of preheated raw materials are squeezed into according to reaction feed ratio with dosing pump respectively micro- mixed
Clutch is entered after being sufficiently mixed is reacted in the micro passage reaction heated in the calorstat of default reaction temperature, in obtaining
The mixed solution of mesosome quaternary ammonium salt；
3) synthetic product：Above-mentioned mixed solution passes through dosing pump again according to reaction feed ratio with preheated strong alkali aqueous solution
Squeezing into enter after micro-mixer is sufficiently mixed is carried out instead in the micro passage reaction heated in the calorstat of default reaction temperature
Should, obtain the oil-water mixture containing product；
4) oil-water separation：Above-mentioned oil-water mixture takes organic faciess through oily water separating equipment point, obtains crude product solution；
5) purification：Crude product solution obtains product dimethylbenzene cyclodimerization body class monomer using concentration purification apparatus purification.
Utilization micro passage reaction of the present invention is prepared in the method for Parylene monomeric compound, as further
Scheme, step 1) in, in trimethylamine aqueous solution the concentration of trimethylamine be 1-5mol/L, the compound with structure formula I molten
In liquid, the concentration of compound is 1-5mol/L；It is preheated to reaction temperature 0-80 DEG C.
Utilization micro passage reaction of the present invention is prepared in the method for Parylene monomeric compound, as further
Scheme, step 2) in, the solution for being driven into micro-mixer trimethylamine aqueous solution with the compound with structure formula I is according to front three
Amine is 1 with the amount ratio of the material of the compound with structure formula I:(0.5-2.0) reaction feed is than mixing.
Utilization micro passage reaction of the present invention is prepared in the method for Parylene monomeric compound, as further
Scheme, step 3) in strong alkali aqueous solution be 1～10mol/L sodium hydrate aqueous solution, preheating temperature be 0～100 DEG C.
Utilization micro passage reaction of the present invention is prepared in the method for Parylene monomeric compound, as further
Scheme, step 3) in, the ratio of the intermediate quaternary ammonium salt squeezed in micro-mixer and the amount of the material of the reaction feed of sodium hydroxide
For 1:(0.5～5).
Utilization micro passage reaction of the present invention is prepared in the method for Parylene monomeric compound, as further
Scheme, step 2) and step 3) in, the internal diameter of the micro passage reaction is 0.1～20mm, 5～25m of length；Calorstat reacts
0～80 DEG C of temperature, raw material stop response time 5s-10min in calorstat.
Utilization micro passage reaction of the present invention is prepared in the method for Parylene monomeric compound, as further
Scheme, the one kind of the compound with structure formula I in following compound：
Compared to existing technology, the beneficial effects of the present invention is：
1. the method that utilization micro passage reaction of the present invention prepares Parylene monomeric compound is continuously micro- logical
The technique for preparing Parylene material monomer compound in road reactor, the technique compared with current traditional handicraft, with low cost,
Energy consumption is little, the three wastes are few, continuously controllable, without enlarge-effect the features such as, simple can be waited than amplifying according to needs of production；
2. utilization micro passage reaction of the present invention prepares the Parylene that the method for Parylene monomeric compound is obtained
Monomeric compound high income, yield can reach more than 97%.
With reference to the accompanying drawings and detailed description the present invention is described in further detail.
Description of the drawings
Fig. 1 is the flow chart of the method that utilization micro passage reaction of the present invention prepares Parylene monomeric compound.
Specific embodiment
The method that utilization micro passage reaction of the present invention prepares Parylene monomeric compound, the method includes following
Step：
1) preheat：The solution of raw material trimethylamine aqueous solution, the compound with structure formula I is each preheating to reaction temperature
Degree；
Wherein R is halogen, p-methyl benzenesulfonic acid base, the one kind in Loprazolam base, X1、X2、X3、X4For H, F, Cl,
One kind in Br, I；
2) synthetic intermediate：Above-mentioned two kinds of preheated raw materials are squeezed into according to reaction feed ratio with dosing pump respectively micro- mixed
Clutch is entered after being sufficiently mixed is reacted in the micro passage reaction heated in the calorstat of default reaction temperature, in obtaining
The mixed solution of mesosome quaternary ammonium salt；
3) synthetic product：Above-mentioned mixed solution passes through dosing pump again according to reaction feed ratio with preheated strong alkali aqueous solution
Squeezing into enter after micro-mixer is sufficiently mixed is carried out instead in the micro passage reaction heated in the calorstat of default reaction temperature
Should, obtain the oil-water mixture containing product；
4) oil-water separation：Above-mentioned oil-water mixture takes organic faciess through oily water separating equipment point, obtains crude product solution；
5) purification：Crude product solution obtains product dimethylbenzene cyclodimerization body class monomer using concentration purification apparatus purification.
Utilization micro passage reaction of the present invention is prepared in the method for Parylene monomeric compound, as further
Scheme, step 1) in, in trimethylamine aqueous solution, the concentration of trimethylamine is 1-5mol/L, it is preferred that the concentration of trimethylamine is 3mol/
L；In the solution of the compound with structure formula I, the concentration of compound is 1-5mol/L, preferably 3mol/L；It is preheated to anti-
Temperature 0-80 DEG C is answered, preferred temperature is 50 DEG C.
Utilization micro passage reaction of the present invention is prepared in the method for Parylene monomeric compound, as further
Scheme, step 2) in, the solution for being driven into micro-mixer trimethylamine aqueous solution with the compound with structure formula I is according to front three
Amine is 1 with the amount ratio of the material of the compound with structure formula I:(0.5-2.0) reaction feed is than mixing；Preferably, two
The ratio of the amount of the material of the charging of person is 1:1.
Utilization micro passage reaction of the present invention is prepared in the method for Parylene monomeric compound, as further
Scheme, step 3) in strong alkali aqueous solution be 1～10mol/L sodium hydrate aqueous solution, preheating temperature be 0～100 DEG C.It is preferred that
, the concentration of sodium hydrate aqueous solution is 6mol/L, and preheating temperature is 60 DEG C.
Utilization micro passage reaction of the present invention is prepared in the method for Parylene monomeric compound, as further
Scheme, step 3) in, the ratio of the intermediate quaternary ammonium salt squeezed in micro-mixer and the amount of the material of the reaction feed of sodium hydroxide
For 1:(0.5～5)；The ratio of the preferably amount of both materials is 1:2.
Utilization micro passage reaction of the present invention is prepared in the method for Parylene monomeric compound, as further
Scheme, step 2) and step 3) in, the internal diameter of the micro passage reaction is 0.1～20mm, 5～25m of length；Calorstat reacts
0～80 DEG C of temperature, raw material stop response time 5s-10min in calorstat.Preferably, the internal diameter of the micro passage reaction is
10mm, length are 15m.Preferably, 60 DEG C of calorstat reaction temperature, raw material stop response time 2min in calorstat.
Utilization micro passage reaction of the present invention is prepared in the method for Parylene monomeric compound, as further
Scheme, the one kind of the compound with structure formula I in following compound：
Some embodiments of the present invention are the following is, in the following embodiments, the raw material, reagent and the equipment that are adopted go out
Prior art is outside particular determination, can be obtained by commercial channel.
Embodiment 1
The method that Parylene monomer [N-type (xylol cyclodimerization body)] is prepared using micro passage reaction, concrete steps
As follows：
1) by the trimethylamine aqueous solution and 3mol/L of 3mol/L to bromomethyl benzyl-trimethyl silane solution, each preheat
Arrive 50 DEG C of reaction temperature；
2) select internal diameter for 10mm, the micro passage reaction of length 15m is reacted, set calorstat reaction temperature 50
DEG C, according to the amount ratio 1 of feed material:1 charge ratio adjusts dosing pump by trimethylamine aqueous solution and to bromomethyl benzyl-trimethyl
Solution of silane squeezes into micro-mixer, and entering after being sufficiently mixed carries out first step reaction in micro passage reaction, stop the response time
1min, obtains the mixed solution of intermediate quaternary ammonium salt；
3) step 2) mixed solution of intermediate quaternary ammonium salt for obtaining and the 6mol/L for being preheating to 60 DEG C of reaction hydroxide
Amount ratio 1 of the sodium water solution according to feed material:Two materials are squeezed into micro-mixer, fully than adjusting dosing pump by 2 reaction
Entering after mixing carries out second step reaction in calorstat micro passage reaction, wherein the internal diameter of micro passage reaction is 10mm, length
Degree 15m, 60 DEG C of calorstat reaction temperature stop response time 2min, obtain the oil-water mixture containing product；
4) oil-water mixture point takes organic faciess through oil-water separation, organic be concentrated into a large amount of solids and separated out, be filtrated to get product
Product Parylene N monomer dimethylbenzene cyclodimerization bodies, yield 97%, HPLC 99.2%.
The reaction equation of embodiment 1 is as follows：
Embodiment 2
The method that Parylene monomer [c-type (a chloro-p-xylene cyclodimerization body)] is prepared using micro passage reaction, specifically
Step is as follows：
1) by chloro- to the trimethylamine aqueous solution and 3mol/L2- of 3mol/L to chloromethyl benzyl-trimethyl silane solution, each
It is preheating to 50 DEG C of reaction temperature；
2) select internal diameter for 8mm, the micro passage reaction of length 10m is reacted, set 50 DEG C of calorstat reaction temperature,
Amount ratio 1 according to feed material:1 charge ratio adjusts dosing pump by chloro- to trimethylamine aqueous solution and 2- to chloromethyl benzyl-front three
Base silane solution squeezes into micro-mixer, and entering after being sufficiently mixed carries out first step reaction in micro passage reaction, when stopping reaction
Between 45s, obtain the mixed solution of intermediate quaternary ammonium salt；
3) step 2) mixed solution of intermediate quaternary ammonium salt for obtaining and the 6mol/L for being preheating to 60 DEG C of reaction hydroxide
Amount ratio 1 of the sodium water solution according to feed material:Two materials are squeezed into micro-mixer by 3 regulation dosing pumps, are sufficiently mixed laggard
Enter, wherein the internal diameter of micro passage reaction be 8mm, length 10m, constant temperature
60 DEG C of case reaction temperature, stops response time 1.5min, obtains the oil-water mixture containing product；
4) oil-water mixture point takes organic faciess through oil-water separation, organic be concentrated into a large amount of solids and separated out, be filtrated to get product
Product Parylene C monomers:One chloro-p-xylene cyclodimerization body, yield 98%, HPLC 99.6%.
The reaction equation of embodiment 2 is as follows：
Embodiment 3
The method that Parylene monomer [D types (dichloro-p-xylene cyclodimerization body)] is prepared using micro passage reaction, specifically
Step is as follows：
1) will be chloro- to the trimethylamine aqueous solution of 3mol/L and 3mol/L 2,5- bis- molten to chloromethyl benzyl-trimethyl silane
Liquid, is each preheating to 45 DEG C of reaction temperature；
2) select internal diameter for 8mm, the micro passage reaction of length 10m is reacted, set 45 DEG C of calorstat reaction temperature,
Amount ratio 1 according to feed material:1 charge ratio adjust dosing pump by chloro- to trimethylamine aqueous solution and 2,5- bis- to chloromethyl benzyl-
Trimethyl silane solution squeezes into micro-mixer, and entering after being sufficiently mixed carries out first step reaction in micro passage reaction, stops anti-
45s between seasonable, obtains the mixed solution of intermediate quaternary ammonium salt；
3) step 2) mixed solution of intermediate quaternary ammonium salt for obtaining and the 6mol/L for being preheating to 55 DEG C of reaction hydroxide
Amount ratio 1 of the sodium water solution according to feed material:Two materials are squeezed into micro-mixer by 2.5 regulation dosing pumps, after being sufficiently mixed
Entering in calorstat micro passage reaction carries out second step reaction, and the wherein internal diameter of micro passage reaction is 8mm, length 10m, permanent
55 DEG C of incubator reaction temperature, stops response time 1.5min, obtains the oil-water mixture containing product；
4) oil-water mixture point takes organic faciess through oil-water separation, organic be concentrated into a large amount of solids and separated out, be filtrated to get product
Product Parylene D monomers:Dichloro-p-xylene cyclodimerization body；Yield 98%, HPLC 99.3%.
The reaction equation of embodiment 3 is as follows：
Embodiment 4
The method that Parylene monomer [F types (tetrafluoro xylol cyclodimerization body)] is prepared using micro passage reaction, specifically
Step is as follows：
1) by tetra- fluoro- p-methyl benzenesulfonic acid ylmethyl benzyl-three of the trimethylamine aqueous solution of 3mol/L and 3mol/L 2,3,5,6-
Methyl-monosilane solution, is each preheating to 60 DEG C of reaction temperature；
2) select internal diameter for 10mm, the micro passage reaction of length 15m is reacted, set calorstat reaction temperature 60
DEG C, according to the amount ratio 1 of feed material:1 charge ratio adjusts dosing pump will be fluoro- to toluene to trimethylamine aqueous solution and 2,3,5,6- tetra-
Sulfonomethyl benzyl-trimethyl silane solution squeezes into micro-mixer, and entering after being sufficiently mixed carries out the in micro passage reaction
Single step reaction, stops response time 90s, obtains the mixed solution of intermediate quaternary ammonium salt；
3) step 2) mixed solution of intermediate quaternary ammonium salt for obtaining and the 6mol/L for being preheating to 65 DEG C of reaction hydroxide
Amount ratio 1 of the sodium water solution according to feed material:Two materials are squeezed into micro-mixer by 3 regulation dosing pumps, are sufficiently mixed laggard
Enter, wherein the internal diameter of micro passage reaction be 8mm, length 15m, constant temperature
65 DEG C of case reaction temperature, stops response time 90s, obtains the oil-water mixture containing product；
4) oil-water mixture point takes organic faciess through oil-water separation, organic be concentrated into a large amount of solids and separated out, be filtrated to get product
Product Parylene F monomers:Tetrafluoro xylol cyclodimerization body；Yield 97%, HPLC 99.4%.
The reaction equation of embodiment 4 is as follows：
Above-mentioned embodiment is only the preferred embodiment of the present invention, it is impossible to limit the scope of protection of the invention with this,
The change of any unsubstantiality that those skilled in the art is done on the basis of the present invention and replacement belong to institute of the present invention
Claimed scope.
Claims (7)
1. a kind of method that utilization micro passage reaction prepares Parylene monomeric compound, it is characterised in that the method include with
Lower step：
1) preheat：The solution of raw material trimethylamine aqueous solution, the compound with structure formula I is each preheating to reaction temperature；
Wherein R is halogen, p-methyl benzenesulfonic acid base, the one kind in Loprazolam base, X1、X2、X3、X4In for H, F, Cl, Br, I
One kind；
2) synthetic intermediate：Above-mentioned two kinds of preheated raw materials are squeezed into micro-mixer with dosing pump according to reaction feed ratio respectively
Enter after being sufficiently mixed and reacted in the micro passage reaction heated in the calorstat of default reaction temperature, obtain intermediate
The mixed solution of quaternary ammonium salt；
3) synthetic product：Above-mentioned mixed solution is squeezed into according to reaction feed ratio by dosing pump with preheated strong alkali aqueous solution again
Micro-mixer is entered after being sufficiently mixed and is reacted in the micro passage reaction heated in the calorstat of default reaction temperature, is obtained
Arrive the oil-water mixture containing product；
4) oil-water separation：Above-mentioned oil-water mixture takes organic faciess through oily water separating equipment point, obtains crude product solution；
5) purification：Crude product solution obtains product dimethylbenzene cyclodimerization body class monomer using concentration purification apparatus purification.
2. method according to claim 1, it is characterised in that step 1) in, the concentration of trimethylamine in trimethylamine aqueous solution
For 1-5mol/L, in the solution of the compound with structure formula I, the concentration of compound is 1-5mol/L；It is preheated to reaction temperature
0-80℃.
3. method according to claim 2, it is characterised in that step 2) in, it is driven into micro-mixer trimethylamine aqueous solution
Amount ratio with the solution of the compound with structure formula I according to trimethylamine with the material of the compound with structure formula I is
1:(0.5-2.0) reaction feed is than mixing.
4. method according to claim 1, it is characterised in that step 3) in strong alkali aqueous solution be 1～10mol/L hydrogen-oxygen
Change sodium water solution, preheating temperature is 0～100 DEG C.
5. method according to claim 1, it is characterised in that step 3) in, the intermediate quaternary ammonium squeezed in micro-mixer
Salt is 1 with the ratio of the amount of the material of the reaction feed of sodium hydroxide:(0.5～5).
6. method according to claim 1, it is characterised in that step 2) and step 3) in, the micro passage reaction
Internal diameter is 0.1～20mm, 5～25m of length；0～80 DEG C of calorstat reaction temperature, raw material stop response time 5s- in calorstat
10min.
7. method according to claim 1, it is characterised in that the compound with structure formula I is selected from following compound
In one kind：
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107216232A (en) * | 2017-06-05 | 2017-09-29 | 昆山彰盛奈米科技有限公司 | A kind of Parylene F preparation method |
| CN108299524A (en) * | 2018-01-09 | 2018-07-20 | 苏州亚科科技股份有限公司 | A kind of preparation method of isopropyl-beta D-thio galactopyranoside intermediate |
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| CN1654449A (en) * | 2005-01-14 | 2005-08-17 | 上海佰伦精细化工有限公司 | Process for preparing dimeric p-xylene |
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| CN1654449A (en) * | 2005-01-14 | 2005-08-17 | 上海佰伦精细化工有限公司 | Process for preparing dimeric p-xylene |
| CN105801848A (en) * | 2016-04-12 | 2016-07-27 | 苏州亚科科技股份有限公司 | Method for preparing polyquaternium-1 by using micro-channel reactor |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107216232A (en) * | 2017-06-05 | 2017-09-29 | 昆山彰盛奈米科技有限公司 | A kind of Parylene F preparation method |
| CN108299524A (en) * | 2018-01-09 | 2018-07-20 | 苏州亚科科技股份有限公司 | A kind of preparation method of isopropyl-beta D-thio galactopyranoside intermediate |
| CN108299524B (en) * | 2018-01-09 | 2021-03-02 | 苏州亚科科技股份有限公司 | Preparation method of isopropyl-beta-D-thiogalactopyranoside intermediate |
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