CN106748627A - A kind of method that one kettle way prepares 3,5 dimethyl bromobenzenes - Google Patents
A kind of method that one kettle way prepares 3,5 dimethyl bromobenzenes Download PDFInfo
- Publication number
- CN106748627A CN106748627A CN201610999079.2A CN201610999079A CN106748627A CN 106748627 A CN106748627 A CN 106748627A CN 201610999079 A CN201610999079 A CN 201610999079A CN 106748627 A CN106748627 A CN 106748627A
- Authority
- CN
- China
- Prior art keywords
- added dropwise
- kettle way
- prepares
- reaction
- reaction vessel
- 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 20
- LMFRTSBQRLSJHC-UHFFFAOYSA-N 1-bromo-3,5-dimethylbenzene Chemical class CC1=CC(C)=CC(Br)=C1 LMFRTSBQRLSJHC-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 20
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 11
- 239000012044 organic layer Substances 0.000 claims abstract description 11
- 229960000583 acetic acid Drugs 0.000 claims abstract description 10
- 239000012362 glacial acetic acid Substances 0.000 claims abstract description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims abstract description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 9
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims abstract description 9
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims abstract description 9
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims abstract description 7
- 235000010288 sodium nitrite Nutrition 0.000 claims abstract description 7
- 238000003756 stirring Methods 0.000 claims abstract description 7
- 238000013517 stratification Methods 0.000 claims abstract description 7
- 238000010792 warming Methods 0.000 claims abstract description 7
- 238000005406 washing Methods 0.000 claims abstract description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 238000009413 insulation Methods 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
- 239000002351 wastewater Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000012954 diazonium Substances 0.000 description 8
- 150000001989 diazonium salts Chemical class 0.000 description 8
- UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical compound CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 125000001246 bromo group Chemical group Br* 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- PVFOHMXILQEIHX-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-bromophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Br PVFOHMXILQEIHX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000004317 sodium nitrate Substances 0.000 description 2
- 235000010344 sodium nitrate Nutrition 0.000 description 2
- FUNDREGHVOYMRG-UHFFFAOYSA-N 2,6-dimethylaniline;sulfuric acid Chemical compound OS(O)(=O)=O.CC1=CC=CC(C)=C1N FUNDREGHVOYMRG-UHFFFAOYSA-N 0.000 description 1
- QGLAYJCJLHNIGJ-UHFFFAOYSA-N 4-bromo-2,6-dimethylaniline Chemical class CC1=CC(Br)=CC(C)=C1N QGLAYJCJLHNIGJ-UHFFFAOYSA-N 0.000 description 1
- 241000208340 Araliaceae Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/20—Diazonium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a kind of method that one kettle way prepares 3,5 dimethyl bromobenzenes, it is comprised the following steps：（a）To glacial acetic acid, dimethylaniline is sequentially added in reaction vessel, sulfuric acid solution is then added dropwise, keeping temperature is 30 ~ 40 DEG C and continues that bromine is added dropwise, and continues stirring reaction 0.5 ~ 1 hour；（b）The reaction vessel is placed in ice bath, sodium nitrite solution is added dropwise thereto and keeping temperature is less than 5 DEG C, be incubated after dripping off and placed；（c）Take hypophosphorous acid to be cooled to less than 5 DEG C, add copper sulphate to form mixture, then drop to step（b）The reaction vessel in, be warming up to after dripping off 15 ~ 30 DEG C reaction overnight, stratification；（d）Take organic layer and enter water-filling, saturated sodium bicarbonate solution washing successively.Greatly save equipment investment cumbersome with what operation brought, greatly reduce the yield of waste water, it is more environmentally friendly.
Description
Technical field
The invention belongs to chemical assistant field, and in particular to a kind of method that one kettle way prepares 3,5- dimethyl bromobenzenes.
Background technology
3,5- dimethyl bromobenzenes are a kind of important chemical intermediates.The 3.5- dimethyl bromobenzenes of high-purity can be used for electricity
Sub- chemical field, wide market.It is industrial at present to be mainly by adding raw material 2,6- diformazans in the presence of glacial acetic acid
Base aniline, is then slowly added dropwise certain density sulfuric acid, is allowed to generate 2,6- dimethylaniline sulfate, and continuing stirring makes 2,6-
Dimethylaniline all dissolves, and then at a temperature of 40 DEG C or so, bromine is slowly added dropwise, and after drop finishes, ice bath is cooled to 0 degree.
Bromo-derivative sulfate solid is separated out, centrifugation obtains white crystal（2,6- dimethyl -4- bromanilines）, then in diazotising kettle
In, by above-mentioned bromo-derivative sulfuric acid dissolution, natrium nitrosum is added dropwise and is allowed to diazotising, then recycle deaminizing for diazol anti-
Should, product is reduced to product 3,5- dimethyl bromobenzenes.It is a production workshop section that the technique often walks reaction, and equipment is huge, technique
It is cumbersome, and just put into next technique as raw material after needing to be purified, cause target product yield low, wastewater flow rate
Greatly.
The content of the invention
A kind of one kettle way is provided and prepares 3,5- dimethyl bromobenzenes the invention aims to overcome the deficiencies in the prior art
Method.
To reach above-mentioned purpose, the technical solution adopted by the present invention is：A kind of one kettle way prepares 3,5- dimethyl bromobenzenes
Method, it is comprised the following steps：
（a）To glacial acetic acid, dimethylaniline is sequentially added in reaction vessel, sulfuric acid solution is then added dropwise, keeping temperature is 30 ~ 40
DEG C continue that bromine is added dropwise, continue stirring reaction 0.5 ~ 1 hour；
（b）The reaction vessel is placed in ice bath, sodium nitrite solution is added dropwise thereto and keeping temperature is less than 5 DEG C, drop
Insulation is placed after complete；
（c）Take hypophosphorous acid to be cooled to less than 5 DEG C, add copper sulphate to form mixture, then drop to step（b）The reaction
In container, 15 ~ 30 DEG C of reactions are warming up to after dripping off overnight, stratification；
（d）Take organic layer and enter water-filling, saturated sodium bicarbonate solution washing successively.
Optimally, step（d）In, rectifying is also carried out after being washed with the saturated sodium bicarbonate solution.
Further, step（c）In, the mixture to step is added dropwise（b）Reaction vessel in when, control programming rate
Ensure the nitrogen not slug that produces with deflation speed.
Further, step（c）In, the mass concentration of copper sulphate is 0.1 ~ 0.2% in the mixture.
Further, step（a）In, the mass ratio of the dimethylaniline, glacial acetic acid, sulfuric acid and bromine is 1：2.5~4：
1~1.5：1~1.5；The mass ratio of the dimethylaniline, natrium nitrosum and hypophosphorous acid is 1：0.5~0.8：4~6.
Because above-mentioned technical proposal is used, the present invention has following advantages compared with prior art：One kettle way system of the present invention
The method of standby 3,5- dimethyl bromobenzenes, carries out the reaction of each step successively in a reaction vessel, and centre does not need extra carrying
The operating procedures such as pure, mother liquid recycle, greatly save cumbersome, the process is simple that equipment investment and operation bring；More meaningful
It is by the control of material rate and be that one kettle way is produced, while product yield is substantially increased, to greatly reduce useless
The yield of water, it is more environmentally friendly.
Specific embodiment
The present invention is further described below in conjunction with embodiment.
Embodiment 1
The present embodiment provides a kind of method that one kettle way prepares 3,5- dimethyl bromobenzenes, and it is comprised the following steps：
（a）To sequentially adding 120g glacial acetic acid, 36g 2,6- dimethylanilines in 500ml there-necked flasks（0.3mol）, then it is added dropwise
Sulfuric acid solution（Include the concentrated sulfuric acids of 40g 98% and 100ml water）, keeping temperature is that 40 DEG C of continuation are added dropwise 48g bromines（0.3mol）,
Continue stirring reaction and cause within 0.5 hour that reaction is complete；The rate of addition of above-mentioned sulfuric acid solution and bromine is also existing conventional ginseng
Number, as long as not causing reaction too many fierce and slug；
（b）There-necked flask is placed in ice bath, down to 0 DEG C or so；Sodium nitrite solution is added dropwise thereto（It is sub- containing 20.6g
Sodium nitrate and 60ml water）, keep it in less than 5 DEG C（Note the nitrogen for controlling programming rate and deflation speed to ensure generation not
Slug）, drip off（Ibid）Insulation placement afterwards forms diazonium salt solution；
（c）Take 182g hypophosphorous acid to be cooled to 0 DEG C, add 0.3g copper sulphate to form mixture, then drop to step（b）Reaction
In container（It is added dropwise in diazonium salt solution, state modulator requirement is added dropwise ibid）, 20 DEG C of reactions are warming up to after dripping off overnight,
There is the transparent organic layer of rufous to separate out；Stratification；
（d）Take organic layer and enter water-filling, saturated sodium bicarbonate solution washing successively（Can repeatedly wash respectively）Obtain final product crude product（Measure
Purity is more than 99%）；Then carrying out rectifying obtains colourless transparent liquid, and weight is 52.3g（Yield is 95.13%）, purity is
99.9%。
Embodiment 2
The present embodiment provides a kind of method that one kettle way prepares 3,5- dimethyl bromobenzenes, and it is comprised the following steps：
（a）To sequentially adding 90g glacial acetic acid, 36g 2,6- dimethylanilines in 500ml there-necked flasks（0.3mol）, sulphur is then added dropwise
Acid solution（Include the concentrated sulfuric acids of 36g 98% and 100ml water）, keeping temperature is 30 DEG C and continues dropwise addition 36g bromines, and continuation is stirred anti-
Answer and cause within 1 hour that reaction is complete；The rate of addition of above-mentioned sulfuric acid solution and bromine is also existing conventional parameter, as long as not causing
Reaction is too many fierce and slug；
（b）There-necked flask is placed in ice bath, down to 0 DEG C or so；Sodium nitrite solution is added dropwise thereto（Contain 18g nitrous
Sour sodium and 60ml water）, keep it in less than 5 DEG C（Notice that the nitrogen for controlling programming rate and deflation speed to ensure generation is not rushed
Material）, drip off（Ibid）Insulation placement afterwards forms diazonium salt solution；
（c）Take 144g hypophosphorous acid to be cooled to 5 DEG C, add 0.28g copper sulphate to form mixture, then drop to step（b）It is anti-
In answering container（It is added dropwise in diazonium salt solution, state modulator requirement is added dropwise ibid）, 30 DEG C are warming up to after dripping off and were reacted
At night, there is the transparent organic layer of rufous to separate out；Stratification；
（d）Take organic layer and enter water-filling, saturated sodium bicarbonate solution washing successively（Can repeatedly wash respectively）Obtain final product crude product（Measure
Purity is more than 99%）；Then carrying out rectifying obtains colourless transparent liquid, and weight is 50.3g（Yield is 91.6%）, purity is 99.9%.
Embodiment 3
The present embodiment provides a kind of method that one kettle way prepares 3,5- dimethyl bromobenzenes, and it is comprised the following steps：
（a）To sequentially adding 144g glacial acetic acid, 36g 2,6- dimethylanilines in 500ml there-necked flasks（0.3mol）, then it is added dropwise
Sulfuric acid solution（Include the concentrated sulfuric acids of 54g 98% and 100ml water）, keeping temperature is 30 DEG C and continues dropwise addition 54g bromines, and continuation is stirred
Reaction causes that reaction is complete for 40 minutes；The rate of addition of above-mentioned sulfuric acid solution and bromine is also existing conventional parameter, as long as not
So that reacting too many fierceness and slug；
（b）There-necked flask is placed in ice bath, down to 0 DEG C or so；Sodium nitrite solution is added dropwise thereto（It is sub- containing 28.8g
Sodium nitrate and 60ml water）, keep it in less than 5 DEG C（Note the nitrogen for controlling programming rate and deflation speed to ensure generation not
Slug）, drip off（Ibid）Insulation placement afterwards forms diazonium salt solution；
（c）Take 216g hypophosphorous acid to be cooled to 0 DEG C, add 0.216g copper sulphate to form mixture, then drop to step（b）It is anti-
In answering container（It is added dropwise in diazonium salt solution, state modulator requirement is added dropwise ibid）, 15 DEG C are warming up to after dripping off and were reacted
At night, there is the transparent organic layer of rufous to separate out；Stratification；
（d）Take organic layer and enter water-filling, saturated sodium bicarbonate solution washing successively（Can repeatedly wash respectively）Obtain final product crude product（Measure
Purity is more than 99%）；Then carrying out rectifying obtains colourless transparent liquid, and weight is 51.5g（Yield is 93.8%）, purity is 99.9%.
Comparative example 1
The present embodiment provides the method that one kind prepares 3,5- dimethyl bromobenzenes, and it is comprised the following steps：
（a）To 120 grams of glacial acetic acid, 36 grams of 36 grams of 2,6- dimethylanilines of addition in 500ml there-necked flasks（0.3mol）, then it is added dropwise
Sulfuric acid solution（Include the concentrated sulfuric acids of 40g 98% and 100ml water；It is kept stirring for so that raw material is completely dissolved, in above-described embodiment 1
It is also such）, keeping temperature is that 40 DEG C of continuation are added dropwise 48g bromines（0.3mol）, continue stirring reaction and cause within 0.5 hour to have reacted
Entirely；
（b）There-necked flask is placed in ice bath, down to 0 DEG C or so；Product is fully separated out, be centrifugally separating to obtain white crystal
The mother liquid recycle for bottom reaction；
（c）By step（b）During the white crystal that obtains adds second 500ml there-necked flask, add a small amount of dilute sulfuric acid to cause
Congored test paper becomes blue, and sodium nitrite solution is then added dropwise thereto（Contain 20.6g natrium nitrosums and 60ml water）, keep it
Below 5 DEG C（Noting controlling programming rate and deflation speed ensures the nitrogen that produces not slug）, drip off（Ibid）Insulation afterwards is put
Put to form diazonium salt solution；
（d）Take 182g hypophosphorous acid to be cooled to 0 DEG C, add 0.3g copper sulphate to form mixture, then drop to step（c）Reaction
In container（It is added dropwise in diazonium salt solution, state modulator requirement is added dropwise ibid）, 20 DEG C of reactions are warming up to after dripping off overnight,
There is the transparent organic layer of rufous to separate out；Stratification；
（d）Take organic layer and enter water-filling, saturated sodium bicarbonate solution washing successively（Can repeatedly wash respectively）Obtain final product crude product（Measure
Purity is more than 99%）；Then carrying out rectifying obtains colourless transparent liquid, and weight is 49.67g（Yield is 90.44%）, purity is
99.5%。
The above embodiments merely illustrate the technical concept and features of the present invention, its object is to allow person skilled in the art
Scholar will appreciate that present disclosure and implement according to this that it is not intended to limit the scope of the present invention, all according to the present invention
The equivalent change or modification that Spirit Essence is made, should all be included within the scope of the present invention.
Claims (5)
1. a kind of method that one kettle way prepares 3,5- dimethyl bromobenzenes, it is characterised in that it is comprised the following steps：
（a）To glacial acetic acid, dimethylaniline is sequentially added in reaction vessel, sulfuric acid solution is then added dropwise, keeping temperature is 30 ~ 40
DEG C continue that bromine is added dropwise, continue stirring reaction 0.5 ~ 1 hour；
（b）The reaction vessel is placed in ice bath, sodium nitrite solution is added dropwise thereto and keeping temperature is less than 5 DEG C, drop
Insulation is placed after complete；
（c）Take hypophosphorous acid to be cooled to less than 5 DEG C, add copper sulphate to form mixture, then drop to step（b）The reaction
In container, 15 ~ 30 DEG C of reactions are warming up to after dripping off overnight, stratification；
（d）Take organic layer and enter water-filling, saturated sodium bicarbonate solution washing successively.
2. the method that one kettle way according to claim 1 prepares 3,5- dimethyl bromobenzenes, it is characterised in that：Step（d）In,
Rectifying is also carried out after being washed with the saturated sodium bicarbonate solution.
3. the method that one kettle way according to claim 1 and 2 prepares 3,5- dimethyl bromobenzenes, it is characterised in that：Step（c）
In, the mixture to step is added dropwise（b）Reaction vessel in when, control programming rate and deflation speed ensure produce nitrogen
Not slug.
4. the method that one kettle way according to claim 1 and 2 prepares 3,5- dimethyl bromobenzenes, it is characterised in that：Step（c）
In, the mass concentration of copper sulphate is 0.1 ~ 0.2% in the mixture.
5. the method that one kettle way according to claim 4 prepares 3,5- dimethyl bromobenzenes, it is characterised in that：Step（a）In,
The mass ratio of the dimethylaniline, glacial acetic acid, sulfuric acid and bromine is 1：2.5~4：1~1.5：1~1.5；The dimethylaniline,
The mass ratio of natrium nitrosum and hypophosphorous acid is 1：0.5~0.8：4~6.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610999079.2A CN106748627A (en) | 2016-11-14 | 2016-11-14 | A kind of method that one kettle way prepares 3,5 dimethyl bromobenzenes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610999079.2A CN106748627A (en) | 2016-11-14 | 2016-11-14 | A kind of method that one kettle way prepares 3,5 dimethyl bromobenzenes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106748627A true CN106748627A (en) | 2017-05-31 |
Family
ID=58973531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610999079.2A Pending CN106748627A (en) | 2016-11-14 | 2016-11-14 | A kind of method that one kettle way prepares 3,5 dimethyl bromobenzenes |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106748627A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111908998A (en) * | 2020-08-12 | 2020-11-10 | 中国科学院化学研究所 | A kind of preparation method of monobrominated aromatic hydrocarbon compound |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1286687A (en) * | 1997-11-11 | 2001-03-07 | H·隆德贝克有限公司 | Method for preparation of citalopram |
| CN101190872A (en) * | 2006-12-01 | 2008-06-04 | 吕铁环 | Method for water-phase fluorination production of 2,6-dimethylfluorobenzene |
| CN101279903A (en) * | 2008-05-23 | 2008-10-08 | 浙江理工大学 | A kind of synthetic method of o-hydroxyacetophenone |
| CN101381303A (en) * | 2007-09-06 | 2009-03-11 | 华东理工大学 | The preparation method of 3-fluorophthalic acid |
| CN101492343A (en) * | 2008-12-30 | 2009-07-29 | 中钢集团鞍山热能研究院有限公司 | Process for producing 3,5-dimethyl bromobenzene |
| CN101528034A (en) * | 2006-10-25 | 2009-09-09 | 辛根塔有限公司 | Process for the production of substituted bromobenzenes |
| CN101553481A (en) * | 2006-09-29 | 2009-10-07 | 格吕伦塔尔有限公司 | Substituted sulfonamide derivatives |
| US20100234652A1 (en) * | 2009-03-12 | 2010-09-16 | Bayer Cropscience Ag | Process for Preparing Chloro-and Bromoaromatics |
| CN102079688A (en) * | 2011-01-28 | 2011-06-01 | 内蒙古工业大学 | Method for preparing 2,3-dichlorotoluene |
| CN104045507A (en) * | 2014-05-30 | 2014-09-17 | 安徽华润涂料有限公司 | Production technology for synthesizing p-bromotoluene |
| US20140323537A1 (en) * | 2013-03-14 | 2014-10-30 | Epizyme, Inc. | Arginine methyltransferase inhibitors and uses thereof |
-
2016
- 2016-11-14 CN CN201610999079.2A patent/CN106748627A/en active Pending
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1286687A (en) * | 1997-11-11 | 2001-03-07 | H·隆德贝克有限公司 | Method for preparation of citalopram |
| CN101553481A (en) * | 2006-09-29 | 2009-10-07 | 格吕伦塔尔有限公司 | Substituted sulfonamide derivatives |
| CN101528034A (en) * | 2006-10-25 | 2009-09-09 | 辛根塔有限公司 | Process for the production of substituted bromobenzenes |
| CN101190872A (en) * | 2006-12-01 | 2008-06-04 | 吕铁环 | Method for water-phase fluorination production of 2,6-dimethylfluorobenzene |
| CN101381303A (en) * | 2007-09-06 | 2009-03-11 | 华东理工大学 | The preparation method of 3-fluorophthalic acid |
| CN101279903A (en) * | 2008-05-23 | 2008-10-08 | 浙江理工大学 | A kind of synthetic method of o-hydroxyacetophenone |
| CN101492343A (en) * | 2008-12-30 | 2009-07-29 | 中钢集团鞍山热能研究院有限公司 | Process for producing 3,5-dimethyl bromobenzene |
| US20100234652A1 (en) * | 2009-03-12 | 2010-09-16 | Bayer Cropscience Ag | Process for Preparing Chloro-and Bromoaromatics |
| CN102079688A (en) * | 2011-01-28 | 2011-06-01 | 内蒙古工业大学 | Method for preparing 2,3-dichlorotoluene |
| US20140323537A1 (en) * | 2013-03-14 | 2014-10-30 | Epizyme, Inc. | Arginine methyltransferase inhibitors and uses thereof |
| CN104045507A (en) * | 2014-05-30 | 2014-09-17 | 安徽华润涂料有限公司 | Production technology for synthesizing p-bromotoluene |
Non-Patent Citations (1)
| Title |
|---|
| ZSANETT HERSECZKI ET AL: "Electronic and steric effects of ligands as control elements for rhodium-catalyzed asymmetric hydrogenation", 《TETRAHEDRON: ASYMMETRY》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111908998A (en) * | 2020-08-12 | 2020-11-10 | 中国科学院化学研究所 | A kind of preparation method of monobrominated aromatic hydrocarbon compound |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101648866B (en) | Preparation technology of p-tert-butyl benzoic acid | |
| CN104774165B (en) | A kind of green industrialized preparation method of rubber peptizer DBD | |
| CN101633612A (en) | Device and process for continuously producing 2-ethyl anthracene quinone in channelization way | |
| CN107162946A (en) | The method that continuous reaction rectification synthesizes isooctyl thioglycolate | |
| CN102009954B (en) | A kind of method that ammonium chloride produces hydrogen chloride and ammonia | |
| CN104817443B (en) | Benzoin dimethyl ether synthesis process | |
| CN106279097B (en) | A kind of preparation method of acrylic -1,3- sultones | |
| CN106748627A (en) | A kind of method that one kettle way prepares 3,5 dimethyl bromobenzenes | |
| CN104628605B (en) | A kind of naphthalene continuous catalysis method of sulfonating and device thereof | |
| CN102161639A (en) | Method for synthesizing pyridinium hydroxy propyl sulfobetaine | |
| CN104892809B (en) | A kind of synthetic biodiesel sulfonic acid functionalized polymer catalyst and preparation method thereof | |
| CN106749096A (en) | The preparation method and device of a kind of rubber vulcanization accelerator DZ | |
| CN104945238A (en) | Isocaprylic acid production process | |
| CN102060812A (en) | Method for preparing epoxy fatty acid methyl ester | |
| CN103524450A (en) | Synthetic method for accelerator DZ by using methanol as solvent | |
| CN104892400B (en) | Catalyze and synthesize oxalic acid intermittent reaction and continuous reaction rectification group technology | |
| CN111138268A (en) | Preparation method of 4,4' -biphenyldicarboxylic acid | |
| CN204490770U (en) | A kind of naphthalene continuous catalysis xanthator | |
| CN105419952B (en) | A kind of method of biodiesel synthesis in eutectic system | |
| CN107311950A (en) | A kind of preparation method of cyanuric acid lanthanum | |
| CN202621148U (en) | Gas-phase medium distributing device with stirring jade glass synthetic reaction kettle | |
| CN112624895A (en) | Green synthesis method of 3,4, 5-trifluorobromobenzene | |
| CN104447329A (en) | Preparation method of 2-chloroacetoacetic acid ethyl ester | |
| CN103524454A (en) | Method for producing rubber vulcanization accelerant DZ by solvent method | |
| CN110330443B (en) | Synthetic process of p-chlorophenylhydrazine hydrochloride |
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 | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20170531 |