CN108929206A - A method of the activation bromo- 1,1- dimethoxy-ethane of 2- - Google Patents
A method of the activation bromo- 1,1- dimethoxy-ethane of 2- Download PDFInfo
- Publication number
- CN108929206A CN108929206A CN201810751991.5A CN201810751991A CN108929206A CN 108929206 A CN108929206 A CN 108929206A CN 201810751991 A CN201810751991 A CN 201810751991A CN 108929206 A CN108929206 A CN 108929206A
- Authority
- CN
- China
- Prior art keywords
- ethane
- bromo
- dimethoxy
- activation
- bicarbonate powder
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 22
- QXBPRWJNNUHXPQ-UHFFFAOYSA-N 1-bromo-1,1-dimethoxyethane Chemical compound COC(C)(Br)OC QXBPRWJNNUHXPQ-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 230000004913 activation Effects 0.000 title claims abstract description 16
- XHXKMTAWMZESFU-UHFFFAOYSA-M silver;hydrogen carbonate Chemical compound [Ag+].OC([O-])=O XHXKMTAWMZESFU-UHFFFAOYSA-M 0.000 claims abstract description 20
- 239000000843 powder Substances 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 13
- 238000004821 distillation Methods 0.000 claims abstract description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 10
- 239000000243 solution Substances 0.000 claims abstract description 9
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 238000001035 drying Methods 0.000 claims abstract description 6
- FUSFWUFSEJXMRQ-UHFFFAOYSA-N 2-bromo-1,1-dimethoxyethane Chemical compound COC(CBr)OC FUSFWUFSEJXMRQ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000007864 aqueous solution Substances 0.000 claims abstract description 5
- 238000002156 mixing Methods 0.000 claims abstract description 5
- 238000000926 separation method Methods 0.000 claims abstract description 5
- 235000011121 sodium hydroxide Nutrition 0.000 claims abstract description 5
- 238000005406 washing Methods 0.000 claims abstract description 5
- 230000009257 reactivity Effects 0.000 claims abstract description 4
- 238000010992 reflux Methods 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 230000003213 activating effect Effects 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract description 4
- 229940006460 bromide ion Drugs 0.000 abstract description 4
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 239000003814 drug Substances 0.000 description 23
- 239000000047 product Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- -1 dibromo compound Chemical class 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/50—Preparation of compounds having groups by reactions producing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/58—Separation; Purification; Stabilisation; Use of additives
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 of bromo- 1,1- dimethoxy-ethane of activation 2-, and suitable bromine, vinyl acetate, solution mixing are sequentially added in reactive tank；The whipping step 1 at a temperature of 55 DEG C) addition of a certain proportion of alcohol-water mixture is refined；Heating, distillation；It is filtered by circulation filter, and silver bicarbonate powder is added；It is washed with sodium hydrate aqueous solution；After washing after sample separation, drying, finished product 2- bromo- 1,1- dimethoxy-ethane can be obtained；Silver bicarbonate powder 0.1g-0.5g is added again, show that reactivity height does not allow bromo- 1, the 1- dimethoxy-ethane of labile finished product 2-.The present invention makes bromo- 1, the 1- dimethoxy-ethane of finished product 2- become active, it is not easy to decompose by adding silver bicarbonate powder to remove extra bromide ion.
Description
Technical field
The present invention relates to medicine intermediate field more particularly to a kind of methods of bromo- 1, the 1- dimethoxy-ethane of activation 2-.
Background technique
Our times bromine resource main application is broadly divided into: medicine and medicine intermediate 19%, fire retardant 32%, oilfield additive
11%, pesticide and pesticide intermediate 12%, dye and dye intermediate 5%, water treatment agent 6%, Chemicals for Photograph and rubber additive
10%, other 5%.Medicine and medicine intermediate industry need nearly 60 kinds of the product of bromine.Needing bromine amount the year of pharmaceuticals industry at present is 1.6 ten thousand
Ton or so, with the raising and progress of industrial technology, market can be gradually expanded, and the medicine intermediate for consuming bromine has biggish hair
Exhibition, currently, medicine intermediate is some chemical products or industrial chemicals required for pharmaceutical synthesis, the conjunction of many chemicals
At the medicine intermediate for depending on high-quality, in order to obtain the medicine intermediate of high quality, the synthesis technology of medicine intermediate is wide
It is concerned.
But brominated medicine intermediate has micro decomposition, and after decomposition, activity is reduced, using effect is influenced,
For industrially scalable, the characteristics of above method, all makes mass production by certain restriction, is unfavorable for industrializing.It is based on
This, it is necessary to develop bromo- 1, the 1- dimethoxy-ethane of the high 2- of reactivity.
Summary of the invention
It is an object of the invention to overcome problem above of the existing technology, a kind of bromo- 1,1- diformazan of activation 2- is provided
The method of oxygroup ethane, by adding silver bicarbonate powder during production bromo- 1, the 1- dimethoxy-ethane of medicine intermediate 2-
Extra bromide ion is removed, so that it is become active, it is not easy to decompose.
To realize above-mentioned technical purpose and the technique effect, the invention is realized by the following technical scheme:
A method of the activation bromo- 1,1- dimethoxy-ethane of 2-, specific preparation step are as follows:
1. sequentially adding suitable bromine, vinyl acetate in reactive tank, solution mixing；
2. being stirred at a temperature of 55 DEG C, turn on agitator, the addition of a certain proportion of alcohol-water mixture is refined；
3. being washed with sodium hydrate aqueous solution；
It is heated at 105~140 DEG C, distillation；
4. steam passes through the filter device circulating filtration of 0.1g-0.5g/ cubic centimetres of silver bicarbonate powder of addition；
5. low water 2- bromo- 1,1- dimethoxy-ethane can be obtained after sample separation, drying after washing；
6. it is 0.1-0.5g/100kg that the amount of silver bicarbonate powder, which is added, in low bromo- 1, the 1- dimethoxy-ethane of water 2-, activation is obtained
Property height does not allow the bromo- 1,1- dimethoxy-ethane of labile finished product 2-.
Preferably, in the step 3) heating distillation the step of can replace with reflux after distill, reflux when
Between be set as 0.2-1h, the time of distillation is set as 1h-2h.
Preferably, the boiling point of the step 1), step 2, step 3) step 4) is arranged at 148-150 °C (lit.).
Preferably, the molar ratio of bromine and vinyl acetate in the step 1 is 1:2.
Preferably, the step 1) neutralization procedure 2) in alcoholization at least react 8h.
Preferably, the circulation filter include the crawler belt being arranged on assembly line, filter screen and be located at flowing water
Feed bin above line is filled with silver bicarbonate powder in the feed bin.
Preferably, the step 1) carries out in order to step 7).
Preferably, the ratio of the alcohol-water mixture in the step 2 accounts for the ratio 1:1.2 of solution in step 1.
The beneficial effects of the present invention are:
1. bromination process not waste of energy, solves and generate more dibromo compound and be difficult to separating-purifying, the problems such as yield is low,
Less by-product and reduced waste, operation of the present invention is more simple, and reaction condition is milder.Especially yield larger amplitude
Degree ground improves, and production cost reduces, and is suitble to industrialized production, is suitble to industrialized production；
2. the technical solution is cooperateed with by the synthesis of the use of suitable reactions substrate and activator, auxiliary agent and facilitation effect, from
And purpose product can be obtained with high yield, purification of products is easy, in organic synthesis especially medicine intermediate synthesis technical field
It has a good application prospect and industrial production potential；
3. yield reaches 90% or more；
4. making finished product become active, it is not easy to decompose by adding silver bicarbonate powder to remove extra bromide ion.
The above description is only an overview of the technical scheme of the present invention, in order to better understand the technical means of the present invention,
And can be implemented in accordance with the contents of the specification, with presently preferred embodiments of the present invention and attached drawing is cooperated to be described in detail below.This hair
Bright specific embodiment is shown in detail by following embodiment and its attached drawing.
Detailed description of the invention
The drawings described herein are used to provide a further understanding of the present invention, constitutes part of this application, this hair
Bright illustrative embodiments and their description are used to explain the present invention, and are not constituted improper limitations of the present invention.In the accompanying drawings:
Fig. 1 is structural schematic diagram of the present invention.
Specific embodiment
The invention will be further described with reference to the accompanying drawing:
Shown in referring to Fig.1, a kind of method of bromo- 1, the 1- dimethoxy-ethane of activation 2-, specific preparation step are as follows:
1. sequentially adding suitable bromine, vinyl acetate in reactive tank, solution mixing；
2. the whipping step 1 at a temperature of 55 DEG C), turn on agitator refines the addition of a certain proportion of alcohol-water mixture；
3. being washed with sodium hydrate aqueous solution；
4. being heated at 105~140 DEG C, distillation；
5. steam passes through the filter device circulating filtration of 0.1g-0.5g/ cubic centimetres of silver bicarbonate powder of addition；
6. low water 2- bromo- 1,1- dimethoxy-ethane can be obtained after sample separation, drying after washing；
7. it is 0.1-0.5g/100kg that the amount of silver bicarbonate powder, which is added, in low bromo- 1, the 1- dimethoxy-ethane of water 2-, activation is obtained
Property height does not allow the bromo- 1,1- dimethoxy-ethane of labile finished product 2-.
Preferably, the step of distillation is heated in the step 3) is distilled after capable of replacing with reflux, the time of reflux
It is set as 0.2-1h, the time of distillation is set as 1h-2h.
Preferably, the boiling point of the step 1), step 2, step 3) step 4) is arranged at 148-150 °C (lit.).
Preferably, the molar ratio of bromine and vinyl acetate in the step 1 is 1:2.
Preferably, the step 1) neutralization procedure 2) in alcoholization at least react 8h.
Preferably, the circulation filter include the crawler belt being arranged on assembly line, filter screen and be located at flowing water
Feed bin above line is filled with silver bicarbonate powder in the feed bin.
Preferably, the step 1) carries out in order to step 7).
Preferably, the ratio of the alcohol-water mixture in the step 2 accounts for the ratio 1:1.2 of solution in step 1).
Specific embodiment 1:
Bromine, vinyl acetate, solution mixing are sequentially added in reactive tank；The whipping step 1 at a temperature of 55 DEG C), turn on agitator,
The addition of a certain proportion of alcohol-water mixture is refined；It is heated at 105~140 DEG C, distillation；Pass through circulation filter mistake
Filter, and silver bicarbonate powder 0.1g-0.5g is added；It is washed with sodium hydrate aqueous solution；After washing after sample separation, drying,
The bromo- 1,1- dimethoxy-ethane of finished product 2- can be obtained；
Silver bicarbonate powder 0.1g-0.5g is added again, show that reactivity height does not allow bromo- 1, the 1- dimethoxy of labile finished product 2-
Base ethane.
In the present invention because after pure medicine intermediate 2- bromo- 1,1- dimethoxy-ethane placement a period of time, meeting
Micro decomposition, after decomposition, the activity for being equivalent to bromo- 1, the 1- dimethoxy-ethane of medicine intermediate 2- is reduced, at this point, passing through
Add silver bicarbonate powder, increases its activity, should be the very high medicine intermediate of purity, and what is actually come out is not pure
Medicine intermediate, have micro silver bicarbonate powder, because containing silver bicarbonate, medicine intermediate inside medicine intermediate
The bromo- 1,1- dimethoxy-ethane of 2- just becomes active.
Because having added silver bicarbonate powder inside bromo- 1, the 1- dimethoxy-ethane of medicine intermediate 2-, once generate bromine from
Son will be carbonated the absorption of hydrogen silver, become silver bromide, precipitate.
The purpose of the present invention is mainly the bromide ion for removing unreacted and finishing, the carbonic acid added after separating drying steps
Hydrogen silver powder is to decompose medicine intermediate during preventing storage, guarantees bromo- 1, the 1- dimethoxy-ethane of medicine intermediate 2-
Activity.
The above description is merely a specific embodiment, but scope of protection of the present invention is not limited thereto, any
Those familiar with the art in the technical scope disclosed by the present invention, can easily think of the change or the replacement, and should all contain
Lid is within protection scope of the present invention.Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.
Claims (8)
1. a kind of method for activating the bromo- 1,1- dimethoxy-ethane of 2-, it is characterised in that: specific preparation step are as follows:
1) suitable bromine, vinyl acetate, solution mixing are sequentially added in reactive tank；
The whipping step 1 at a temperature of 55 DEG C), turn on agitator refines the addition of a certain proportion of alcohol-water mixture；
It is washed with sodium hydrate aqueous solution；
It is heated at 105~140 DEG C, distillation；
The filter device circulating filtration that steam passes through 0.1g-0.5g/ cubic centimetres of silver bicarbonate powder of addition；
After washing after sample separation, drying, low water 2- bromo- 1,1- dimethoxy-ethane can be obtained；
It is 0.1-0.5g/100kg that the amount of silver bicarbonate powder, which is added, in low bromo- 1, the 1- dimethoxy-ethane of water 2-, obtains reactivity
Height does not allow the bromo- 1,1- dimethoxy-ethane of labile finished product 2-.
2. a kind of method of bromo- 1,1- dimethoxy-ethane of activation 2- according to claim 1, it is characterised in that: described
The step of distillation is heated in step 3) is distilled after capable of replacing with reflux, and the time of reflux is set as 0.2-1h, distillation when
Between be set as 1h-2h.
3. a kind of method of bromo- 1,1- dimethoxy-ethane of activation 2- according to claim 1, it is characterised in that: described
The boiling point setting of step 1), step 2, step 3) step 4) is at 148-150 °C (lit.).
4. a kind of method of bromo- 1,1- dimethoxy-ethane of activation 2- according to claim 1, it is characterised in that: described
The molar ratio of bromine and vinyl acetate in step 1 is 1:2.
5. a kind of method of bromo- 1,1- dimethoxy-ethane of activation 2- according to claim 1, it is characterised in that: described
Step 1) neutralization procedure 2) in alcoholization at least react 8h.
6. a kind of method of bromo- 1,1- dimethoxy-ethane of activation 2- according to claim 1, it is characterised in that: described
Circulation filter includes the crawler belt being arranged on assembly line, filter screen and the feed bin above assembly line, the feed bin
Inside it is filled with silver bicarbonate powder.
7. a kind of method of bromo- 1,1- dimethoxy-ethane of activation 2- according to claim 1, it is characterised in that: described
Step 1) carries out in order to step 7).
8. a kind of method of bromo- 1,1- dimethoxy-ethane of activation 2- according to claim 1, it is characterised in that: described
The ratio of alcohol-water mixture in step 2 accounts for the ratio 1:1.2 of solution in step 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810751991.5A CN108929206A (en) | 2018-07-10 | 2018-07-10 | A method of the activation bromo- 1,1- dimethoxy-ethane of 2- |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810751991.5A CN108929206A (en) | 2018-07-10 | 2018-07-10 | A method of the activation bromo- 1,1- dimethoxy-ethane of 2- |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN108929206A true CN108929206A (en) | 2018-12-04 |
Family
ID=64446944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810751991.5A Pending CN108929206A (en) | 2018-07-10 | 2018-07-10 | A method of the activation bromo- 1,1- dimethoxy-ethane of 2- |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108929206A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112047818A (en) * | 2019-06-06 | 2020-12-08 | 石家庄欧特佳化工有限公司 | Green method for preparing chloroacetaldehyde dialkyl acetal from vinyl acetate |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2146016B (en) * | 1983-09-06 | 1986-10-29 | Ciba Geigy Ag | Method for the preparation of haloacetals and halodioxolanes |
| US4851567A (en) * | 1988-01-16 | 1989-07-25 | Bayer Aktiengesellschaft | N,N'-bis(5-isocyanatonaphthyl)urea, a process for its production, and its use |
-
2018
- 2018-07-10 CN CN201810751991.5A patent/CN108929206A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2146016B (en) * | 1983-09-06 | 1986-10-29 | Ciba Geigy Ag | Method for the preparation of haloacetals and halodioxolanes |
| US4851567A (en) * | 1988-01-16 | 1989-07-25 | Bayer Aktiengesellschaft | N,N'-bis(5-isocyanatonaphthyl)urea, a process for its production, and its use |
Non-Patent Citations (2)
| Title |
|---|
| PAUL Z. BEDOUKIAN: "Synthesis of bromoacetals", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》 * |
| 金嵇煜等: "2，2-二甲氧基乙胺的制备", 《精细化工中间体》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112047818A (en) * | 2019-06-06 | 2020-12-08 | 石家庄欧特佳化工有限公司 | Green method for preparing chloroacetaldehyde dialkyl acetal from vinyl acetate |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107033107A (en) | A kind of method for preparing epoxychloropropane | |
| CN112645793B (en) | Process system and method for producing trans-1-chloro-3, 3-trifluoropropene | |
| CN105859571A (en) | Method for producing glycine by mixed solvent method | |
| DE69818091T2 (en) | PROCESS FOR THE PREPARATION OF DERIVATIVES OF BROMMETHYL-BIPHENYL COMPOUNDS | |
| CN101613363B (en) | Preparation process of hexamethyldisilazane | |
| CN103896808A (en) | Method of preparing azodiisobutyronitrile | |
| CN108929206A (en) | A method of the activation bromo- 1,1- dimethoxy-ethane of 2- | |
| JP2019523243A5 (en) | ||
| CN106892792A (en) | A kind of method for continuously synthesizing and its synthesis device of 3,4 2 chlorobenzotrifluoride | |
| CN106699591A (en) | Clean production process of glycine and co-produced ammonium chloride | |
| CN104592044B (en) | The low temperature synthetic method of 2,6-Dichloro-4-nitroaniline | |
| CN105348052B (en) | The synthesis technology of 2- propoxyl group chloroethanes | |
| CN108203392A (en) | A kind of process for cleanly preparing of glycine in coproduction with ammonium chloride | |
| CN105693510A (en) | Preparation method of ethyl 6,8-dichlorocaprylate | |
| CN100500631C (en) | The preparation method of 3-trifluoromethylbenzoic acid | |
| CN106699522A (en) | Production process of high-quality trimethyl orthoacetate | |
| DE102004060627A1 (en) | Process for the continuous production of amino groups carrying silicon compounds | |
| CN101250565A (en) | Method for preparing 1,2-epoxycyclohexane by lipase catalyzed oxidation of cyclohexene | |
| CN108997091A (en) | A kind of method of silver bicarbonate activation 2- Bromoethyl phenyl ether | |
| CN105330520A (en) | Method for synthesizing tetrabromobisphenol A bis(2,3-dibromopropyl) ether in water phase | |
| TW201806915A (en) | Preparation system and preparation method of aromatic derivative | |
| CN106673978B (en) | 3,5- Dichloro-2-pentanone is continuously synthesizing to method | |
| CN107445793A (en) | A kind of distillation and separation method of benzene chloride production | |
| CN105294392B (en) | To the preparation method of benzyl dichloride | |
| CN111018728A (en) | A kind of method and device for preparing 3-chloro-alanine hydrochloride with water as auxiliary agent |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20181204 |