CN106495977B - A method of Parylene monomeric compound is prepared using micro passage reaction - Google Patents
A method of Parylene monomeric compound is prepared using micro passage reaction Download PDFInfo
- Publication number
- CN106495977B CN106495977B CN201610792280.3A CN201610792280A CN106495977B CN 106495977 B CN106495977 B CN 106495977B CN 201610792280 A CN201610792280 A CN 201610792280A CN 106495977 B CN106495977 B CN 106495977B
- Authority
- CN
- China
- Prior art keywords
- reaction
- compound
- solution
- micro
- micro passage
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of methods for preparing Parylene monomeric compound using micro passage reaction, this method includes preheating, synthetic intermediate, synthetic product, water-oil separating, purifying, Parylene material monomer compound is prepared in continuous micro passage reaction, have the characteristics that at low cost, energy consumption is small, the three wastes are few, it is continuous controllable, without enlarge-effect, it can be simple to wait than amplification according to needs of production.
Description
Technical field
The invention belongs to macromolecule synthesising technology fields, and in particular to a kind of to prepare Parylene list using micro passage reaction
The method of body compound.
Background technique
Parylene, Pai Lalun (Parylene) are a kind of protectiveness high molecular 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 a kind of) unique solids coating in the adopted name of series of polymers and 105D military standard 105D.Parylene uses vacuum
Gas-phase deposition forms protective film, and this film has the characteristics that thickness is uniform, fine and close 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.
Currently, the Parylene material widely commercially applied has Parylene (Parylene N), a poly- chloro pair
Dimethylbenzene (Parylene C), poly- dichloro- paraxylene (Parylene D) and polytetrafluoro are for paraxylene (Parylene F)
Deng their main distinction is the difference of substituent group type or substituent group quantity on molecule, to determine in thermal stability
With the difference in terms of insulation performance.Parylene material is pyrolyzed under vacuum by the monomer paraxylene cyclodimerization body of different structure
And vapor deposition polymerization, at made of Parylene series polymer, common monomer has N-type (paraxylene cyclodimerization body), C
Type (a chloro-p-xylene cyclodimerization body), D type (dichloro-p-xylene cyclodimerization body) and F type (tetrafluoro paraxylene cyclodimerization
Body) etc..
Parylene monomer
The continuous expansion applied in every field with Parylene material, Parylene monomer paraxylene cyclodimerization body class
The synthesis of compound has great importance to the preparation and application of Parylene material.Currently, tradition prepares paraxylene ring two
The method of aggressiveness class compound usually has two classes.It is earliest that one is the Pintsch process cyclizations for directlying adopt paraxylene class substrate
It obtains, temperature needed for this method is higher, generally requires 750 DEG C~1000 DEG C, and there are many side reaction, and yield general 30% is left
It is right；This method energy consumption is high, and yield is low, and applicable substrate is seldom, and the xylene substrate containing substituent group is difficult to use this method
Produce corresponding dimer (Nature, 1949,915；Chemistry Letter, 1990, vol.6,893-896), at present
Use this method to produce paraxylene cyclodimerization body class compound again without enterprise substantially.Relatively conventional production method is now
Hofmann elimination is crossed to obtain.This method, to methylbenzyl quaternary ammonium salt monomer, carries out hofmann elimination by heating
Prepare paraxylene cyclodimerization body.Such method is due to being water-oil phase reaction, it is generally difficult to realize the abundant mixed of reaction system
Splice grafting touching, although reaction temperature lowers significantly, yield offer is not obvious.For problems, after in United States Patent (USP) Shen
There please be open disclose by addition DMSO, U.S. Patent application US4806702 to add crown ether or polyethers in US4532369, and or
Person by add the substances such as promotors or phase transfer catalysis (PTC) such as quaternary ammonium fluoride salt reported in the literature promote the reaction of two-phase system into
Journey improves yield.Although such method is compared with high-temperature cracking method, reaction temperature is substantially reduced, and yield has reached medium level
(highest 75% or so), but its reaction system be typically all the batch production in traditional tank reactor, the production cycle compared with
It is long, to be generally more than 24 hours, cannot achieve continuous production, energy requirements are big, and production efficiency is low；Due to addition in production process
Multiple catalysts, subsequent purification are difficult；Solvent usage amount is big in production, and the three wastes accordingly generated are also very much.
Under Green Development background, a kind of continuous, efficient, energy-saving and environmental protection Parylene monomeric compound producer is developed
Formula is of great significance.
Summary of the invention
For overcome the deficiencies in the prior art, micro passage reaction preparation group is utilized the purpose of the present invention is to provide a kind of
The method of Rayleigh monomeric compound prepares Parylene material monomer compound in continuous micro passage reaction, have it is at low cost,
The features such as energy consumption is small, the three wastes are few, continuous controllable, without enlarge-effect, can be simple to wait than amplification according to needs of production.
To solve the above problems, the technical solution adopted in the present invention is as follows:
A method of Parylene monomeric compound being prepared using micro passage reaction, method includes the following steps:
1) it preheats: the solution of raw material trimethylamine aqueous solution, the compound with structural formula (I) is respectively preheating to reaction temperature
Degree；
Wherein R is one of halogen, p-methyl benzenesulfonic acid base, Loprazolam base, X1、X2、X3、X4For H, F, Cl,
One of Br, I；
2) above-mentioned two kinds of preheated raw materials synthetic intermediate: are squeezed into micro- mix according to reaction feed ratio with metering pump respectively
Clutch enters in the micro passage reaction heated in the insulating box of default reaction temperature after being sufficiently mixed is reacted, and is obtained
The mixed solution of mesosome quaternary ammonium salt；
3) synthetic product: above-mentioned mixed solution passes through metering pump according to reaction feed ratio with preheated strong alkali aqueous solution again
It squeezes into after micro-mixer is sufficiently mixed in the micro passage reaction for entering and being heated in the insulating box of default reaction temperature and carries out instead
It answers, obtains the oil-water mixture containing product；
4) water-oil separating: above-mentioned oil-water mixture takes organic phase through oily water separating equipment point, obtains crude product solution；
5) purify: crude product solution is purified using concentration purification apparatus, obtains product dimethylbenzene cyclodimerization body class monomer.
In the method for the present invention for preparing Parylene monomeric compound using micro passage reaction, as further
Scheme, in step 1), the concentration of trimethylamine is 1-5mol/L in trimethylamine aqueous solution, the compound with structural formula (I) it is molten
The concentration of compound is 1-5mol/L in liquid；It is preheated to 0-80 DEG C of reaction temperature.
In the method for the present invention for preparing Parylene monomeric compound using micro passage reaction, as further
Scheme in step 2), is driven into micro-mixer trimethylamine aqueous solution with the solution of the compound with structural formula (I) according to front three
Reaction feed ratio of the amine with the mass ratio of the material of the compound with structural formula (I) for 1:(0.5-2.0) mixes.
In the method for the present invention for preparing Parylene monomeric compound using micro passage reaction, as further
Scheme, strong alkali aqueous solution is the sodium hydrate aqueous solution of 1~10mol/L in step 3), and preheating temperature is 0~100 DEG C.
In the method for the present invention for preparing Parylene monomeric compound using micro passage reaction, as further
Scheme in step 3), squeezes into the ratio between the amount of substance of reaction feed of the intermediate quaternary ammonium salt and sodium hydroxide in micro-mixer
For 1:(0.5~5).
In the method for the present invention for preparing Parylene monomeric compound using micro passage reaction, as further
In scheme, step 2) and step 3), the internal diameter of the micro passage reaction is 0.1~20mm, 5~25m of length；Insulating box reaction
0~80 DEG C of temperature, raw material stops reaction time 5s-10min in insulating box.
In the method for the present invention for preparing Parylene monomeric compound using micro passage reaction, as further
Scheme, the compound with structural formula (I) are selected from one of following compound:
Compared with prior art, the beneficial effects of the present invention are:
1. the method for the present invention for preparing Parylene monomeric compound using micro passage reaction is continuous micro- logical
The technique that Parylene material monomer compound is prepared in road reactor, the technique compared with current traditional handicraft, have it is at low cost,
The features such as energy consumption is small, the three wastes are few, continuous controllable, without enlarge-effect, can be simple to wait than amplification according to needs of production；
2. the Parylene that the method for the present invention for preparing Parylene monomeric compound using micro passage reaction obtains
Monomeric compound high income, yield can achieve 97% or more.
Invention is further described in detail with reference to the accompanying drawings and detailed description.
Detailed description of the invention
Fig. 1 is the flow chart of the method for the present invention that Parylene monomeric compound is prepared using micro passage reaction.
Specific embodiment
The method of the present invention for preparing Parylene monomeric compound using micro passage reaction, this method include following
Step:
1) it preheats: the solution of raw material trimethylamine aqueous solution, the compound with structural formula (I) is respectively preheating to reaction temperature
Degree；
Wherein R is one of halogen, p-methyl benzenesulfonic acid base, Loprazolam base, X1、X2、X3、X4For H, F, Cl,
One of Br, I；
2) above-mentioned two kinds of preheated raw materials synthetic intermediate: are squeezed into micro- mix according to reaction feed ratio with metering pump respectively
Clutch enters in the micro passage reaction heated in the insulating box of default reaction temperature after being sufficiently mixed is reacted, and is obtained
The mixed solution of mesosome quaternary ammonium salt；
3) synthetic product: above-mentioned mixed solution passes through metering pump according to reaction feed ratio with preheated strong alkali aqueous solution again
It squeezes into after micro-mixer is sufficiently mixed in the micro passage reaction for entering and being heated in the insulating box of default reaction temperature and carries out instead
It answers, obtains the oil-water mixture containing product；
4) water-oil separating: above-mentioned oil-water mixture takes organic phase through oily water separating equipment point, obtains crude product solution；
5) purify: crude product solution is purified using concentration purification apparatus, obtains product dimethylbenzene cyclodimerization body class monomer.
In the method for the present invention for preparing Parylene monomeric compound using micro passage reaction, as further
Scheme, in step 1), the concentration of trimethylamine is 1-5mol/L in trimethylamine aqueous solution, it is preferred that the concentration of trimethylamine is 3mol/
L；The concentration of compound is 1-5mol/L, preferably 3mol/L in the solution of compound with structural formula (I)；It is preheated to anti-
0-80 DEG C of temperature is answered, preferred temperature is 50 DEG C.
In the method for the present invention for preparing Parylene monomeric compound using micro passage reaction, as further
Scheme in step 2), is driven into micro-mixer trimethylamine aqueous solution with the solution of the compound with structural formula (I) according to front three
Reaction feed ratio of the amine with the mass ratio of the material of the compound with structural formula (I) for 1:(0.5-2.0) mixes；Preferably, two
The ratio between amount of substance of charging of person is 1:1.
In the method for the present invention for preparing Parylene monomeric compound using micro passage reaction, as further
Scheme, strong alkali aqueous solution is the sodium hydrate aqueous solution of 1~10mol/L in step 3), and preheating temperature is 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.
In the method for the present invention for preparing Parylene monomeric compound using micro passage reaction, as further
Scheme in step 3), squeezes into the ratio between the amount of substance of reaction feed of the intermediate quaternary ammonium salt and sodium hydroxide in micro-mixer
For 1:(0.5~5)；The ratio between both preferred amount of substance is 1:2.
In the method for the present invention for preparing Parylene monomeric compound using micro passage reaction, as further
In scheme, step 2) and step 3), the internal diameter of the micro passage reaction is 0.1~20mm, 5~25m of length；Insulating box reaction
0~80 DEG C of temperature, raw material stops reaction time 5s-10min in insulating box.Preferably, the internal diameter of the micro passage reaction is
10mm, length 15m.Preferably, 60 DEG C of insulating box reaction temperature, raw material stop reaction time 2min in insulating box.
In the method for the present invention for preparing Parylene monomeric compound using micro passage reaction, as further
Scheme, the compound with structural formula (I) are selected from one of following compound:
It is some embodiments of the present invention below, in the following embodiments, used raw material, reagent and equipment go out
It is the prior art outside particular determination, can be obtained by commercial channel.
Embodiment 1
The method for preparing Parylene monomer [N-type (paraxylene cyclodimerization body)] using micro passage reaction, specific steps
It is as follows:
1) trimethylamine aqueous solution of 3mol/L and 3mol/L respectively preheat bromomethyl benzyl-trimethyl silane solution
To 50 DEG C of reaction temperature；
2) select internal diameter for 10mm, the micro passage reaction of length 15m is reacted, and insulating box reaction temperature 50 is set
DEG C, metering pump is adjusted by trimethylamine aqueous solution and to bromomethyl benzyl-trimethyl according to the amount ratio 1:1 charge ratio of feed material
Solution of silane squeezes into micro-mixer, enters after being sufficiently mixed and carries out first step reaction in micro passage reaction, stops the reaction time
1min obtains the mixed solution of intermediate quaternary ammonium salt；
3) mixed solution for the intermediate quaternary ammonium salt that step 2) obtains and the hydroxide for being preheating to the 6mol/L for reacting 60 DEG C
Two materials, than adjusting metering pump, are squeezed into micro-mixer, sufficiently according to the reaction of the amount ratio 1:2 of feed material by sodium water solution
Enter after mixing and carry out second step reaction in insulating box micro passage reaction, wherein the internal diameter of micro passage reaction is 10mm, length
15m is spent, 60 DEG C of insulating box reaction temperature, reaction time 2min is stopped, obtains the oil-water mixture containing product；
4) oil-water mixture takes organic phase through water-oil separating point, organic to be concentrated into a large amount of solids precipitations, and production is obtained by filtration
Product Parylene N monomer dimethylbenzene cyclodimerization body, yield 97%, HPLC 99.2%.
The reaction equation of embodiment 1 is as follows:
Embodiment 2
The method for preparing Parylene monomer [c-type (a chloro-p-xylene cyclodimerization body)] using micro passage reaction, specifically
Steps are as follows:
1) trimethylamine aqueous solution of 3mol/L and 3mol/L2- is chloro- to chloromethyl benzyl-trimethyl silane solution, respectively
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, 50 DEG C of insulating box reaction temperature are set,
Metering pump is adjusted according to the amount ratio 1:1 charge ratio of feed material, and trimethylamine aqueous solution and 2- is chloro- to chloromethyl benzyl-front three
Base silane solution squeezes into micro-mixer, enters after being sufficiently mixed and carries out first step reaction in micro passage reaction, when stopping reaction
Between 45s, obtain the mixed solution of intermediate quaternary ammonium salt；
3) mixed solution for the intermediate quaternary ammonium salt that step 2) obtains and the hydroxide for being preheating to the 6mol/L for reacting 60 DEG C
Sodium water solution adjusts metering pump according to the amount ratio 1:3 of feed material and two materials is squeezed into micro-mixer, is sufficiently mixed laggard
Enter and carry out second step reaction in insulating box micro passage reaction, wherein the internal diameter of micro passage reaction is 8mm, length 10m, constant temperature
60 DEG C of case reaction temperature, reaction time 1.5min is stopped, the oil-water mixture containing product is obtained；
4) oil-water mixture takes organic phase through water-oil separating point, organic to be concentrated into a large amount of solids precipitations, and production is obtained by filtration
Product Parylene C monomer: a chloro-p-xylene cyclodimerization body, yield 98%, HPLC 99.6%.
The reaction equation of embodiment 2 is as follows:
Embodiment 3
The method for preparing Parylene monomer [D type (dichloro-p-xylene cyclodimerization body)] using micro passage reaction, specifically
Steps are as follows:
1) trimethylamine aqueous solution of 3mol/L and 3mol/L 2,5- bis- is chloro- molten to chloromethyl benzyl-trimethyl silane
Liquid is respectively preheating to 45 DEG C of reaction temperature；
2) select internal diameter for 8mm, the micro passage reaction of length 10m is reacted, 45 DEG C of insulating box reaction temperature are set,
Metering pump is adjusted according to the amount ratio 1:1 charge ratio of feed material, and trimethylamine aqueous solution and 2,5- bis- is chloro- to chloromethyl benzyl-
Trimethyl silane solution squeezes into micro-mixer, enters after being sufficiently mixed and carries out first step reaction in micro passage reaction, stops anti-
45s between seasonable, obtains the mixed solution of intermediate quaternary ammonium salt；
3) mixed solution for the intermediate quaternary ammonium salt that step 2) obtains and the hydroxide for being preheating to the 6mol/L for reacting 55 DEG C
Sodium water solution adjusts metering pump according to the amount ratio 1:2.5 of feed material and two materials is squeezed into micro-mixer, after being sufficiently mixed
Second step reaction is carried out in into insulating box micro passage reaction, wherein the internal diameter of micro passage reaction is 8mm, length 10m, perseverance
55 DEG C of incubator reaction temperature, reaction time 1.5min is stopped, the oil-water mixture containing product is obtained；
4) oil-water mixture takes organic phase through water-oil separating point, organic to be concentrated into a large amount of solids precipitations, and production is obtained by filtration
Product Parylene D monomer: dichloro-p-xylene cyclodimerization body；Yield 98%, HPLC 99.3%.
The reaction equation of embodiment 3 is as follows:
Embodiment 4
The method for preparing Parylene monomer [F type (tetrafluoro paraxylene cyclodimerization body)] using micro passage reaction, specifically
Steps are as follows:
1) by the trimethylamine aqueous solution of 3mol/L and the fluoro- p-methyl benzenesulfonic acid ylmethyl benzyl-three of 3mol/L 2,3,5,6- tetra-
Methyl-monosilane solution is respectively preheating to 60 DEG C of reaction temperature；
2) select internal diameter for 10mm, the micro passage reaction of length 15m is reacted, and insulating box reaction temperature 60 is set
DEG C, metering pump is adjusted according to the amount ratio 1:1 charge ratio of feed material, and trimethylamine aqueous solution and 2,3,5,6- tetra- is fluoro- to toluene
Sulfonomethyl benzyl-trimethyl silane solution squeezes into micro-mixer, enters after being sufficiently mixed and carries out the in micro passage reaction
Single step reaction stops reaction time 90s, obtains the mixed solution of intermediate quaternary ammonium salt；
3) mixed solution for the intermediate quaternary ammonium salt that step 2) obtains and the hydroxide for being preheating to the 6mol/L for reacting 65 DEG C
Sodium water solution adjusts metering pump according to the amount ratio 1:3 of feed material and two materials is squeezed into micro-mixer, is sufficiently mixed laggard
Enter and carry out second step reaction in insulating box micro passage reaction, wherein the internal diameter of micro passage reaction is 8mm, length 15m, constant temperature
65 DEG C of case reaction temperature, reaction time 90s is stopped, the oil-water mixture containing product is obtained；
4) oil-water mixture takes organic phase through water-oil separating point, organic to be concentrated into a large amount of solids precipitations, and production is obtained by filtration
Product Parylene F monomer: tetrafluoro paraxylene cyclodimerization body；Yield 97%, HPLC 99.4%.
The reaction equation of embodiment 4 is as follows:
The above embodiment is only the preferred embodiment of the present invention, and the scope of protection of the present invention is not limited thereto,
The variation and replacement for any unsubstantiality that those skilled in the art is done on the basis of the present invention belong to institute of the present invention
Claimed range.
Claims (7)
1. a kind of method for preparing Parylene monomeric compound using micro passage reaction, which is characterized in that this method include with
Lower step:
1) it preheats: the solution of raw material trimethylamine aqueous solution, the compound with structural formula (I) is respectively preheating to reaction temperature；
Wherein R is one of halogen, p-methyl benzenesulfonic acid base, Loprazolam base, X1、X2、X3、X4For one in H, F, Cl, Br, I
Kind；
2) above-mentioned two kinds of preheated raw materials synthetic intermediate: are squeezed into micro-mixer according to reaction feed ratio with metering pump respectively
Enter in the micro passage reaction heated in the insulating box of default reaction temperature after being sufficiently mixed and reacted, obtains intermediate
The mixed solution of quaternary ammonium salt；
3) synthetic product: above-mentioned mixed solution is squeezed by metering pump according to reaction feed ratio with preheated strong alkali aqueous solution again
Micro-mixer, which enters after being sufficiently mixed in the micro passage reaction heated in the insulating box of default reaction temperature, to be reacted, and is obtained
To the oil-water mixture containing product；
4) water-oil separating: above-mentioned oil-water mixture takes organic phase through oily water separating equipment point, obtains crude product solution；
5) purify: crude product solution is purified using concentration purification apparatus, obtains product dimethylbenzene cyclodimerization body class monomer.
2. the method according to claim 1, wherein in step 1), the concentration of trimethylamine in trimethylamine aqueous solution
For 1-5mol/L, having the concentration of compound in the solution of the compound of structural formula (I) is 1-5mol/L；It is preheated to reaction temperature
0-80℃。
3. according to the method described in claim 2, it is characterized in that, being driven into micro-mixer trimethylamine aqueous solution in step 2)
With the solution of the compound with structural formula (I) according to trimethylamine and the mass ratio of the material of the compound with structural formula (I) is
Reaction feed 1:(0.5-2.0) is than mixing.
4. the method according to claim 1, wherein strong alkali aqueous solution is the hydrogen-oxygen of 1~10mol/L in step 3)
Change sodium water solution, preheating temperature is 0~100 DEG C.
5. the method according to claim 1, wherein squeezing into the intermediate quaternary ammonium in micro-mixer in step 3)
The ratio between amount of substance of reaction feed of salt and sodium hydroxide is 1:(0.5~5).
6. the method according to claim 1, wherein in step 2) and step 3), the micro passage reaction
Internal diameter is 0.1~20mm, 5~25m of length；0~80 DEG C of insulating box reaction temperature, raw material stops reaction time 5s- in insulating box
10min。
7. the method according to claim 1, wherein the compound with structural formula (I) is selected from following compound
One of:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610792280.3A CN106495977B (en) | 2016-08-31 | 2016-08-31 | A method of Parylene monomeric compound is prepared using micro passage reaction |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610792280.3A CN106495977B (en) | 2016-08-31 | 2016-08-31 | A method of Parylene monomeric compound is prepared using micro passage reaction |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106495977A CN106495977A (en) | 2017-03-15 |
| CN106495977B true CN106495977B (en) | 2019-01-08 |
Family
ID=58290226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610792280.3A Active CN106495977B (en) | 2016-08-31 | 2016-08-31 | A method of Parylene monomeric compound is prepared using micro passage reaction |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106495977B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116283482A (en) * | 2017-06-05 | 2023-06-23 | 昆山彰盛奈米科技有限公司 | Preparation method of parylene F |
| 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 |
| CN117776834A (en) * | 2023-12-26 | 2024-03-29 | 深圳方寸达科技有限公司 | Preparation method of parylene material monomer |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
2016
- 2016-08-31 CN CN201610792280.3A patent/CN106495977B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Non-Patent Citations (1)
| Title |
|---|
| Room Temperature Observation of p-Xylylenes by 1H NMR and Evidence for Diradical Intermediates in Their Oligomerization;WalterS.Trahanovsky et al.;《J.Org.Chem.》;20061231;第71卷;1784-1794 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106495977A (en) | 2017-03-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106495977B (en) | A method of Parylene monomeric compound is prepared using micro passage reaction | |
| CN105597561B (en) | A kind of organic silicon sol preparation method and application swung based on pH | |
| CN109678727A (en) | A kind of method of microchannel nitration reaction synthesis 2- ethyl -5- nitroaniline | |
| CN108250435B (en) | Thick oil emulsifying viscosity reducer and application thereof | |
| CN105017118A (en) | Method for preparing 2-methylaziridine by using microchannel reactor | |
| CN103274908A (en) | Bisphenol monomer containing bi-tert-butyl and fluorenyl structure, and preparation method and application thereof | |
| CN107501242B (en) | D-pi-A type dipyrrole fluorescent dye and synthetic method thereof | |
| CN103194501B (en) | Method for synthetizing chiral cyclic alkyl amino acid by amino transferase | |
| CN111004126A (en) | Preparation method of p-nitrophenol sodium salt | |
| TWI807290B (en) | Method for synthesizing oxetane derivative by using microreactor | |
| CN109384725A (en) | A kind of method of microchannel diazo reaction synthesis 3- methyl -6- nitro -1H- indazole | |
| CN109422663B (en) | Method for continuous flow synthesis of quaternary ammonium salt | |
| CN104262127B (en) | Brush-type two fluorine monomer and synthetic method thereof | |
| CN102604101B (en) | Synthesis method for phenyl organosilicon copolymer with uniformly distributed phenyl units | |
| CN101935282A (en) | Synthesis method of 1, 5-dichloro-2-iso propyl-4-nitrobenzene | |
| CN103773079B (en) | The method of Pigment red 177 is prepared in ionic liquid | |
| CN104926696A (en) | Preparation method of N,N-dimethylallyl propanesulfonate | |
| CN103787925B (en) | A kind of methylacryoyloxyethyl-N, the synthetic method of N-dimethyl propylene sulfonate | |
| CN115304745B (en) | Resveratrol and isovanillin based bio-based composite epoxy resin and preparation method thereof | |
| CN214088354U (en) | Preparation system containing 3-amino-2-formamide pyridine structure compound | |
| CN104311455B (en) | A kind of preparation method of 2 acrylamido 2 methyl-prop (alkane) sulfonic acid | |
| CN106631751A (en) | Anti-oxidation type multi-methyl side-chain difluoro monomer and preparation method of monomer | |
| CN113201004B (en) | Method for rapidly preparing cyclopropane derivatives based on microchannel reaction technology | |
| CN107573266A (en) | A kind of synthetic method of 4-hydrazinobenzene-1-sulfonamide hydrochloride | |
| CN209906684U (en) | Semi-continuous production device of 3, 4-dimethylpyrazole phosphate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CP02 | Change in the address of a patent holder |
Address after: 215000 No. 388 Shui Shui Road, Suzhou Industrial Park, Jiangsu Patentee after: SUZHOU YACOO SCIENCE Co.,Ltd. Address before: 215000 Changyang street, Suzhou Industrial Park, Jiangsu, China, No. 415, No. Patentee before: SUZHOU YACOO SCIENCE Co.,Ltd. |
|
| CP02 | Change in the address of a patent holder |