CN1323771A - Method for preparing 1-bromo-3-methyl-2-butene - Google Patents
Method for preparing 1-bromo-3-methyl-2-butene Download PDFInfo
- Publication number
- CN1323771A CN1323771A CN 00112272 CN00112272A CN1323771A CN 1323771 A CN1323771 A CN 1323771A CN 00112272 CN00112272 CN 00112272 CN 00112272 A CN00112272 A CN 00112272A CN 1323771 A CN1323771 A CN 1323771A
- Authority
- CN
- China
- Prior art keywords
- bromo
- methyl
- butene
- isoprene
- hydrogen bromide
- 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.)
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- LOYZVRIHVZEDMW-UHFFFAOYSA-N 1-bromo-3-methylbut-2-ene Chemical compound CC(C)=CCBr LOYZVRIHVZEDMW-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 title description 6
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims abstract description 34
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims abstract description 13
- 150000004820 halides Chemical class 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 5
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims description 4
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 claims description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 238000004821 distillation Methods 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- YXZFFTJAHVMMLF-UHFFFAOYSA-N 1-bromo-3-methylbutane Chemical compound CC(C)CCBr YXZFFTJAHVMMLF-UHFFFAOYSA-N 0.000 description 1
- -1 3-bromo-2-methyl-1-butene alkene Chemical class 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000002977 biomimetic material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The 1-bromo-3-methyl-2-butene is prepared by reacting isoprene with hydrobromic acid (20-54% concentration) or hydrogen bromide gas at-20-30 deg.C, and adding cuprous halide as catalyst to obtain 1-bromo-3-methyl-2-butene.
Description
The present invention relates to the preparation method of 1-bromo-3-methyl-2-butene.
1-bromo-3-methyl-2-butene is a kind of broad-spectrum fine-chemical intermediate, be mainly used in fields such as medication chemistry, biomimetic material, the preparation method of 1-bromo-3-methyl-2-butene is not seen relevant report, general synthetic this compounds adopts method (" basic organic chemistry " Xing Qiyi, Xu Ruiqiu, the Zhou Zheng chief editor of diene and halogenide addition, Higher Education Publishing House published in 198 0), 1,3-divinyl and hydrogenchloride addition get 1,4 affixture 1-chloro-2-butylene and 1,2 affixture 3-chloro-1-butylene, product characteristics is similar, is difficult to separate single product.Similar reaction can take place in isoprene and hydrogen bromide, generates 1,4 affixture 1-bromo-3-methyl-2-butene, 1,2 affixture 3-bromo-2-methyl-1-butene alkene and two molecule affixtures 1,3-two bromo-3-methyl-butane.Because product is more, be difficult to separate and purify, influence is used.
The purpose of this invention is to provide a kind of method that highly selective, high-level efficiency easy and simple to handle, that raw material is cheap are produced 1-bromo-3-methyl-2-butene that has.
It is the addition raw material that the present invention adopts Hydrogen bromide or bromize hydrogen gas.Hydrogen bromide concentration is 20-54% (mass ratio), and the ratio of Hydrogen bromide and isoprene can be selected 0.5-3 for use: 1 (same under the mole ratio), and preferred proportion is 1-2: 1; When adopting bromize hydrogen gas and isoprene addition, the ratio of hydrogen bromide and isoprene is 0.4-1.5: 1, and preferable ratio is 0.7-1.2: 1.
It is catalyzer that the present invention can adopt cuprous halide, and typically selecting cuprous bromide for use is catalyzer, and its consumption is 0-5% (with the mass ratio of isoprene), (the adding of catalyzer can both not produce 1-bromo-3-methyl-2-butene).
The temperature that the present invention adopts changes in a big way, and generally at-20-30 ℃, wherein optimum temps is-5-5 ℃.
But the present invention finishes within a short period of time, and its process can adopt chromatogram tracking.
Below by embodiment the present invention is further specified.
Embodiment 1: install agitator, thermometer, prolong in the 1000ml reactor, drop into 136g (content is 99%) isoprene, be chilled to-5 ℃, Dropwise 5 609 (content is 54%) Hydrogen bromide, drip process temperature and be controlled at 0-5 ℃, dropwise, 1 hour sampling analysis of insulation reaction, isoprene containing 8.2%, 1-bromo-3-methyl-2-butene 84.4%, tell Hydrogen bromide, 59-61 ℃/60mmHg cut is collected in underpressure distillation, gets 1-bromo-3-methyl-2-butene 256.3g, content g 7%, yield 84%.
Embodiment 2, press embodiment 1 same operation, add the 6g cuprous bromide, get 1-bromo-3-methyl-2-butene 270g, content 96.7%, yield 88.2%.
Embodiment 3: in 500ml four-hole reactor, and device agitator, thermometer, prolong, airway; Add the 68g isoprene, be chilled to-10 ℃, begin to feed bromize hydrogen gas; In venting process, temperature control-5-0 ℃, common people's bromize hydrogen gas 88g, sampling analysis, isoprene containing 5.6%, 1-bromo-3-methyl-2-butene 80%, underpressure distillation gets 1-bromo-3-methyl-2-butene 127.3g, content 95.3%, yield 82.1%.
Embodiment 4: presses embodiment 3 same operation, adds the 6g cuprous bromide, and sampling analysis, isoprene containing 7.2%, 1-bromo-3-methyl-2-butene 84%, underpressure distillation gets 1-bromo-3-methyl-2-butene 132.1g, content 97.4%, yield 87%.
Claims (5)
1. the preparation method of a 1-bromo-3-methyl-2-butene is characterized in that:
Raw material is isoprene and Hydrogen bromide (concentration is 20-54%) or bromize hydrogen gas.
Temperature of reaction is :-20-30 ℃.
Catalyzer is: cuprous halide (the adding of catalyzer can both not produce 1-bromo-3-methyl-2-butene).
2. according to the preparation method of right 1 described 1-bromo-3-methyl-2-butene, it is characterized in that the ratio of raw material is:
Hydrogen bromide: isoprene is 0.5: 1-3: 1 (same under the mole ratio).
Hydrogen bromide: isoprene is 0.4: 1-1.5: 1
3. according to the preparation method of claim 1 and 2 described 1-bromo-3-methyl-2-butenes, it is characterized in that the optimum proportion of raw material is:
Hydrogen bromide: isoprene is 1: 1-2: 1
Hydrogen bromide: isoprene is 0.7: 1-1.2: 1
4. the preparation method of 1-bromo-3-methyl-2-butene according to claim 1 is characterized in that the catalyzer cuprous halide can adopt cuprous bromide etc., and its consumption is 0-5% (with the isoprene mass ratio).
5. the preparation method of 1-bromo-3-methyl-2-butene according to claim 1 is characterized in that reacting optimum temps and is-5-5 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 00112272 CN1323771A (en) | 2000-05-15 | 2000-05-15 | Method for preparing 1-bromo-3-methyl-2-butene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 00112272 CN1323771A (en) | 2000-05-15 | 2000-05-15 | Method for preparing 1-bromo-3-methyl-2-butene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1323771A true CN1323771A (en) | 2001-11-28 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 00112272 Pending CN1323771A (en) | 2000-05-15 | 2000-05-15 | Method for preparing 1-bromo-3-methyl-2-butene |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1323771A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109020783A (en) * | 2018-07-18 | 2018-12-18 | 浙江师范大学 | The preparation method of the bromo- 2- butylene-1,4-diol of one kind (E) -2,3- two |
-
2000
- 2000-05-15 CN CN 00112272 patent/CN1323771A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109020783A (en) * | 2018-07-18 | 2018-12-18 | 浙江师范大学 | The preparation method of the bromo- 2- butylene-1,4-diol of one kind (E) -2,3- two |
| CN109020783B (en) * | 2018-07-18 | 2020-04-28 | 浙江师范大学 | A kind of preparation method of (E)-2,3-dibromo-2-butene-1,4-diol |
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