CN111138242A - Synthesis method of 2-bromo-4-chloro-1-isopropylbenzene - Google Patents
Synthesis method of 2-bromo-4-chloro-1-isopropylbenzene Download PDFInfo
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- CN111138242A CN111138242A CN201911295976.5A CN201911295976A CN111138242A CN 111138242 A CN111138242 A CN 111138242A CN 201911295976 A CN201911295976 A CN 201911295976A CN 111138242 A CN111138242 A CN 111138242A
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- CN
- China
- Prior art keywords
- chlorotoluene
- reaction
- isopropylbenzene
- bromo
- chloro
- Prior art date
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- BCARRKVCHXVTJE-UHFFFAOYSA-N 2-bromo-4-chloro-1-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(Cl)C=C1Br BCARRKVCHXVTJE-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000001308 synthesis method Methods 0.000 title claims abstract description 23
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 claims abstract description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 238000003756 stirring Methods 0.000 claims abstract description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 10
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 claims abstract description 10
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 238000003860 storage Methods 0.000 claims abstract description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000005485 electric heating Methods 0.000 claims abstract description 5
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 claims description 86
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 64
- 238000000034 method Methods 0.000 claims description 51
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 48
- 238000006243 chemical reaction Methods 0.000 claims description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 36
- 239000007788 liquid Substances 0.000 claims description 25
- IBSQPLPBRSHTTG-UHFFFAOYSA-N 1-chloro-2-methylbenzene Chemical compound CC1=CC=CC=C1Cl IBSQPLPBRSHTTG-UHFFFAOYSA-N 0.000 claims description 24
- 230000002194 synthesizing effect Effects 0.000 claims description 23
- 238000002425 crystallisation Methods 0.000 claims description 20
- 238000005660 chlorination reaction Methods 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 15
- 239000000047 product Substances 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 14
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 14
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 14
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 12
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 238000005804 alkylation reaction Methods 0.000 claims description 8
- 239000007789 gas Substances 0.000 claims description 8
- 239000012153 distilled water Substances 0.000 claims description 7
- 238000005265 energy consumption Methods 0.000 claims description 7
- 238000004880 explosion Methods 0.000 claims description 7
- 239000011552 falling film Substances 0.000 claims description 7
- 230000008014 freezing Effects 0.000 claims description 7
- 238000007710 freezing Methods 0.000 claims description 7
- 239000002808 molecular sieve Substances 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 7
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 7
- 238000001179 sorption measurement Methods 0.000 claims description 7
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 6
- 206010010741 Conjunctivitis Diseases 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- 201000004624 Dermatitis Diseases 0.000 claims description 6
- 229910001209 Low-carbon steel Inorganic materials 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 6
- 230000003444 anaesthetic effect Effects 0.000 claims description 6
- 239000001569 carbon dioxide Substances 0.000 claims description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- 230000029142 excretion Effects 0.000 claims description 6
- 229910052742 iron Inorganic materials 0.000 claims description 6
- 210000004185 liver Anatomy 0.000 claims description 6
- 230000007246 mechanism Effects 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 210000004400 mucous membrane Anatomy 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 6
- 230000001681 protective effect Effects 0.000 claims description 6
- 210000000952 spleen Anatomy 0.000 claims description 6
- 238000009825 accumulation Methods 0.000 claims description 5
- 231100000053 low toxicity Toxicity 0.000 claims description 5
- LGXAANYJEHLUEM-UHFFFAOYSA-N 1,2,3-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1C(C)C LGXAANYJEHLUEM-UHFFFAOYSA-N 0.000 claims description 4
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 claims description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 4
- 230000009471 action Effects 0.000 claims description 4
- 230000029936 alkylation Effects 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 239000006227 byproduct Substances 0.000 claims description 4
- 239000012295 chemical reaction liquid Substances 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 238000001704 evaporation Methods 0.000 claims description 4
- 230000008020 evaporation Effects 0.000 claims description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 238000007086 side reaction Methods 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 239000000575 pesticide Substances 0.000 abstract description 21
- 239000000839 emulsion Substances 0.000 abstract description 11
- 230000000361 pesticidal effect Effects 0.000 abstract description 11
- 238000010189 synthetic method Methods 0.000 abstract description 10
- 238000009333 weeding Methods 0.000 abstract description 6
- 241000238631 Hexapoda Species 0.000 abstract description 4
- 239000004480 active ingredient Substances 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 description 10
- 238000002485 combustion reaction Methods 0.000 description 7
- 238000000926 separation method Methods 0.000 description 5
- 230000009286 beneficial effect Effects 0.000 description 4
- 230000001276 controlling effect Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 241000607479 Yersinia pestis Species 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000006273 synthetic pesticide Substances 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- -1 amide compounds Chemical class 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000004503 fine granule Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000002316 fumigant Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003750 molluscacide Substances 0.000 description 1
- 230000002013 molluscicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- QIIPQYDSKRYMFG-UHFFFAOYSA-N phenyl hydrogen carbonate Chemical class OC(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000003128 rodenticide Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000004563 wettable powder Substances 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
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
-
- 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
- C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
- C07C2/68—Catalytic processes with halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/125—Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium
- C07C2527/126—Aluminium chloride
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the technical field of pesticide production, and discloses a synthetic method of 2-bromo-4-chloro-1-isopropylbenzene, which comprises the following steps: the synthesis method of the 2-bromopropane comprises the following steps: adding sodium bromide, water, isopropanol and catalyst into a 250ml four-necked bottle equipped with a stirrer, an electric heating jacket, a dropping funnel, a water separator, a thermometer and a condenser, slowly dropping a certain amount of concentrated sulfuric acid under stirring, controlling the dropping speed to ensure that the temperature does not exceed 3O ℃, and heating to 50-60 ℃ after dropping. The synthetic method of the 2-bromo-4-chloro-1-isopropylbenzene has the advantages of strong practicability, good pesticide effect and the like, and solves the problem that the pesticide emulsion has storage stability of pesticide active ingredients, but in actual application, the pesticide effect of the pesticide emulsion is obvious and general, so that the effects of weeding, killing insects and the like are greatly discounted, and the practicability of the pesticide emulsion is influenced, so that the synthetic method of the 2-bromo-4-chloro-1-isopropylbenzene is provided for solving the problems.
Description
Technical Field
The invention relates to the technical field of pesticide production, in particular to a synthetic method of 2-bromo-4-chloro-1-isopropylbenzene.
Background
The pesticide is a chemical agent which is used for preventing and controlling plant diseases and insect pests and regulating plant growth in agriculture, is widely used for agriculture, forestry and animal husbandry production, environmental and household sanitation, pest and disease control, industrial product mildew and moth prevention and the like, has a plurality of pesticide varieties, and can be mainly divided into insecticide, acaricide, rodenticide, nematicide, molluscicide, bactericide, herbicide, plant growth regulator and the like according to the application; according to the raw material source, the pesticide can be divided into mineral source pesticides (inorganic pesticides), biological source pesticides (natural organic matters, microorganisms, antibiotics and the like) and chemical synthetic pesticides; according to chemical structure, mainly comprises organic chlorine, organic phosphorus, organic nitrogen, organic sulfur, carbamate, pyrethroid, amide compounds, urea compounds, ether compounds, phenolic compounds, phenoxy carboxylic acids, amidines, triazoles, heterocycles, benzoic acids, organic metal compounds and the like, which are all organic synthetic pesticides; it can be divided into powder, wettable powder, emulsion, emulsifiable concentrate, emulsifiable paste, cataplasm, colloidal agent, fumigant, smoking agent, aerosol, granule, fine granule, oil agent, etc. according to the preparation formulation.
According to the pesticide emulsion composition provided by the Chinese patent publication No. CN 1968603A, the pesticide emulsion has the storage stability of the pesticide active ingredient, but in the practical application, the pesticide effect of the pesticide emulsion is obvious and general, so that the efficacy of weeding, killing insects and the like is greatly reduced, and the practicability of the pesticide emulsion is influenced, so that the synthetic method of the 2-bromo-4-chloro-1-isopropylbenzene is provided for solving the problems.
Disclosure of Invention
Technical problem to be solved
Aiming at the defects of the prior art, the invention provides a synthetic method of 2-bromo-4-chloro-1-isopropylbenzene, which has the advantages of strong practicability, good pesticide effect and the like, and solves the problem that the pesticide emulsion has storage stability of pesticide active ingredients, but in practical application, the pesticide effect of the pesticide emulsion is obvious and general, so that the effects of weeding, killing insects and the like are greatly discounted, and the practicability of the pesticide emulsion is influenced, and therefore, the synthetic method of the 2-bromo-4-chloro-1-isopropylbenzene is provided for solving the problems.
(II) technical scheme
In order to achieve the purposes of strong practicability and good drug effect, the invention provides the following technical scheme: the synthesis method of the 2-bromo-4-chloro-1-isopropylbenzene comprises the following steps:
1) the synthesis method of the 2-bromopropane comprises the following steps: adding sodium bromide, water, isopropanol and a catalyst into a 250ml four-necked bottle provided with a stirrer, an electric heating jacket, a dropping funnel, a water separator, a thermometer and a condenser in a ratio, slowly dropwise adding a certain amount of concentrated sulfuric acid under stirring, controlling the dropwise adding speed to ensure that the temperature does not exceed 3O ℃, heating to 50-60 ℃ after dropwise adding, reacting for 1h, heating until a fraction is distilled, keeping reflux until no fraction is distilled, washing the distillate with distilled water, 10% sodium carbonate and water in sequence, distilling in a distillation flask, and collecting the 67-69 ℃ fraction;
2) the synthesis method of the 4-chlorotoluene comprises the following steps: toluene dried and dehydrated by salt enters a toluene chlorination reactor after being metered by a metering tank, metered chlorine is introduced from the bottom of the reactor, toluene and chlorine are subjected to benzene ring chlorination by taking ferric chloride as a catalyst at a certain temperature to generate monochlorotoluene chlorination liquid, the chlorination liquid uses nitrogen to drive off residual gas and hydrogen chloride, and then coarse evaporation is carried out to obtain a mixture of p-chlorotoluene and o-chlorotoluene, the ratio of the p-chlorotoluene to the o-chlorotoluene is different along with different catalysts and reaction conditions, generally the ratio of the p-chlorotoluene to the o-chlorotoluene is 55: 45, the p-chlorotoluene and the o-chlorotoluene can be separated by a rectification method, a molecular sieve adsorption method, a rectification crystallization method and the like, the rectification crystallization method has low energy consumption, the obtained p-chlorotoluene and o-chlorotoluene have high content, and the content of the p-chlorotoluene can reach more than 99 percent if a falling film freezing crystallization method is;
3) the method for synthesizing the isopropyl benzene comprises the following steps: the alkylation reaction is carried out on benzene and propylene, aluminum trichloride is generally adopted as a catalyst and hydrogen chloride is adopted as an accelerant, the reaction is carried out at normal pressure and about 95 ℃, polyalkyl byproducts such as diisopropylbenzene and triisopropylbenzene are generated in addition to cumene, excessive benzene can be adopted for reducing side reaction, the molar ratio of benzene to propylene is about 3, the content of aluminum trichloride in a reaction liquid is 3% -8%, the reaction is carried out at low propylene concentration, the reaction pressure can be increased to 0.5-0.6MPa for improving the production capacity of a reactor and reducing the loss of benzene in tail gas, the solid (the complex of aluminum trichloride and polyisopropylbenzene) separated from an alkylation liquid obtained by the reaction after cooling and precipitation is recycled, and the cumene is obtained by hydrolyzing, neutralizing and rectifying the alkylation liquid;
4) synthesizing: adding 2-bromopropane, 4-chlorotoluene and isopropyl benzene into a reaction kettle, pressurizing and stirring, increasing the reaction pressure to 0.7-0.8MPa, and stirring for twenty-thirty minutes.
Preferably, the 2-bromopropane needs to be subjected to emergency treatment in the synthesis process: if leakage emergency treatment, protective measures and emergency measures are taken, 2-bromopropane is inflammable, a ventilated low-temperature and dry environment needs to be kept in the storage and transportation process, and the synthetic reaction mechanism of the 2-bromopropane is as follows:
preferably, the 4-chlorotoluene is inflammable, has the risk of causing combustion explosion in case of naked fire, and can react violently when being contacted with an oxidant to combust (decompose) products: the carbon monoxide, the carbon dioxide and the hydrogen chloride should be made to have anti-leakage emergency work, and the leakage of the 4-chlorotoluene is strictly avoided.
Preferably, the cumene is a class 3.3 high flash point flammable liquid, critical specification number: 33538, UN numbering: 1918, the product has no corrosiveness to metal, can be stored in iron, mild steel, copper or aluminum container, but need avoid using rubber product in valve and gasket, belongs to low toxicity, can irritate skin and mucous membrane, has strong anesthetic action, causes conjunctivitis and dermatitis, and is harmful to spleen and liver, can produce accumulation action due to slow excretion, and has highest allowable concentration of 245.5-491 mg/m at workplace.
(III) advantageous effects
Compared with the prior art, the invention provides a synthetic method of 2-bromo-4-chloro-1-isopropylbenzene, which has the following beneficial effects:
1. the synthesis method of the 2-bromo-4-chloro-1-isopropylbenzene is simplified by a synthesis method of 2-bromopropane, a synthesis method of 4-chlorotoluene and a synthesis method of the isopropylbenzene, the concentration and the extraction rate of the isopropylbenzene are improved, a certain amount of concentrated sulfuric acid is slowly dripped under the stirring of the synthesis method of the 2-bromopropane, the dripping speed is controlled, the temperature is not more than 3O ℃, the temperature is raised to 50 ℃ after the dripping is finished, the reaction is carried out for 1 hour, then the temperature is raised until a fraction is distilled, the reflux is kept until no more fraction is distilled, the distillate is sequentially washed by distilled water, 10 percent sodium carbonate and water, then distilled in a distillation flask, the 67 ℃ fraction is collected, the synthesis method of the 4-chlorotoluene, the separation of the chlorotoluene and the O-chlorotoluene can be carried out by a rectification method, a molecular sieve adsorption method, the rectification crystallization combination method has low energy consumption, the obtained p-chlorotoluene and o-chlorotoluene have high content, if a falling film freezing crystallization method is adopted, the content of the p-chlorotoluene can reach more than 99 percent, the alkylated liquid in the cumene synthesis method is hydrolyzed, neutralized and rectified to obtain cumene and other procedures to obtain synthetic raw materials, and finally the synthetic raw materials are pressurized and stirred to obtain the final 2-bromo-4-chloro-1-isopropylbenzene mixture, wherein the cited raw materials and the final mixture have high-efficiency and strong weeding and insecticidal effects, and the pesticide effect is enhanced, so that the aims of strong practicability and good pesticide effect are fulfilled.
2. According to the method for synthesizing the 2-bromo-4-chloro-1-isopropylbenzene, corresponding emergency treatment needs to be carried out in the synthesis process of the 2-bromopropane: if leakage emergency treatment, protective measures and emergency measures are taken, 2-bromopropane is inflammable, a ventilated low-temperature and dry environment needs to be kept in the storage and transportation process, the synthetic reaction mechanism of 2-bromopropane is that 4-chlorotoluene is inflammable and has the danger of combustion and explosion when meeting open fire, the 4-chlorotoluene can react violently when contacting with an oxidant, and products are combusted (decomposed): carbon monoxide, carbon dioxide and hydrogen chloride, should do emergency work such as preventing leaking, stop 4-chlorotoluene's leakage strictly, cumene is 3.3 class high flash point flammable liquid, danger regulation number: 33538, UN numbering: 1918, the synthetic method has no corrosion to metals, can be stored in iron, mild steel, copper or aluminum containers, avoids the use of rubber products in valves and gaskets, belongs to low toxicity, can stimulate skin and mucous membranes, has strong anesthetic action, causes conjunctivitis and dermatitis, is harmful to spleen and liver, can generate accumulation action due to slow excretion, has a maximum allowable concentration of 245.5-491 mg/m in a working place, can effectively ensure the safety of the synthetic method of the 2-bromo-4-chloro-1-isopropylbenzene in the processing process, and ensures the production safety of the 2-bromo-4-chloro-1-isopropylbenzene.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The first embodiment is as follows:
the synthesis method of the 2-bromo-4-chloro-1-isopropylbenzene comprises the following steps:
1) the synthesis method of the 2-bromopropane comprises the following steps: adding sodium bromide, water, isopropanol and a catalyst into a 250ml four-necked bottle provided with a stirrer, an electric heating jacket, a dropping funnel, a water separator, a thermometer and a condenser in a ratio, slowly dropwise adding a certain amount of concentrated sulfuric acid under stirring, controlling the dropwise adding speed to ensure that the temperature does not exceed 3O ℃, after the dropwise adding is finished, heating to 50 ℃, reacting for 1h, heating until a distillate fraction is distilled, keeping reflux until no distillate fraction is distilled, washing the distillate with distilled water, 10% sodium carbonate and water in sequence, distilling in a distillation flask, collecting 67 ℃ distillate, and carrying out emergency treatment on the 2-bromopropane in the synthetic process: if leakage emergency treatment, protective measures and emergency measures are taken, 2-bromopropane is inflammable, a ventilated low-temperature and dry environment needs to be kept in the storage and transportation process, and the synthetic reaction mechanism of the 2-bromopropane is as follows:
2) the synthesis method of the 4-chlorotoluene comprises the following steps: toluene dried and dehydrated by salt enters a toluene chlorination reactor after being metered by a metering tank, metered chlorine is introduced from the bottom of the reactor, toluene and chlorine are subjected to benzene ring chlorination by taking ferric chloride as a catalyst at a certain temperature to generate monochlorotoluene chlorination liquid, the chlorination liquid uses nitrogen to drive off residual gas and hydrogen chloride, and then is subjected to rough evaporation to obtain a mixture of p-chlorotoluene and o-chlorotoluene, the ratio of the p-chlorotoluene to the o-chlorotoluene is different along with the difference of the catalyst and reaction conditions, generally the ratio of the p-chlorotoluene to the o-chlorotoluene is 55: 45, the separation of the p-chlorotoluene and the o-chlorotoluene can be realized by a rectification method, a molecular sieve adsorption method, a rectification crystallization method and the like, the rectification crystallization method has low energy consumption, the obtained p-chlorotoluene and o-chlorotoluene have high content, if a falling film freezing crystallization method is adopted, the content of the p-chlorotoluene can reach more than 99 percent, and, the danger of combustion explosion in the case of open fire, violent reaction in contact with the oxidizing agent, combustion (decomposition) of the products: the carbon monoxide, the carbon dioxide and the hydrogen chloride should be made to have anti-leakage emergency work, and the leakage of the 4-chlorotoluene is strictly avoided;
3) the method for synthesizing the isopropyl benzene comprises the following steps: is prepared by the alkylation reaction of benzene and propylene, usually adopts aluminum trichloride as a catalyst and hydrogen chloride as an accelerant, the reaction is carried out at normal pressure and about 95 ℃, besides cumene, polyalkyl byproducts such as diisopropylbenzene, triisopropylbenzene and the like are generated, excessive benzene can be adopted to reduce side reaction, the molar ratio of the benzene to the propylene is about 3, the content of the aluminum trichloride in the reaction liquid is 3-8 percent, the reaction is carried out under low propylene concentration, in order to improve the production capacity of the reactor and reduce the loss of benzene in tail gas, the reaction pressure can be increased to 0.5MPa, the solid (aluminum trichloride and polyisopropylbenzene complex) separated from the alkylated liquid obtained by the reaction after cooling and precipitation is recycled, the alkylated liquid is hydrolyzed, neutralized and rectified to obtain isopropylbenzene, the isopropylbenzene is 3.3-class high-flash-point flammable liquid, and the critical specification is as follows: 33538, UN numbering: 1918 it has no corrosiveness to metal, and can be stored in iron, mild steel, copper or aluminum container, but it is avoided to use rubber product in valve and gasket, and it is low toxic, can irritate skin and mucous membrane, has strong anesthetic effect, causes conjunctivitis and dermatitis, and is harmful to spleen and liver, and can accumulate due to slow excretion, and has a working site tolerance of 245.5mg/m at maximum;
4) synthesizing: adding 2-bromopropane, 4-chlorotoluene and isopropyl benzene into a reaction kettle, pressurizing and stirring, increasing the reaction pressure to 0.7-0.8MPa, and stirring for twenty-thirty minutes.
The invention has the beneficial effects that: the method for synthesizing 2-bromopropane, the method for synthesizing 4-chlorotoluene and the method for synthesizing isopropyl benzene are simplified, the concentration and the extraction rate are improved, a certain amount of concentrated sulfuric acid is slowly dripped under the stirring of the method for synthesizing 2-bromopropane, the dripping speed is controlled, the temperature does not exceed 3O ℃, the dripping is finished, the temperature is raised to 60 ℃ after the dripping is finished, the reaction is carried out for 1h, then the temperature is raised until a fraction is distilled, the reflux is kept until no more fraction is distilled, the distillate is sequentially washed by distilled water, 10 percent sodium carbonate and water, then the distillation is carried out in a distillation flask, the fraction at 69 ℃ is collected, the method for synthesizing 4-chlorotoluene is adopted, the separation of p-chlorotoluene and O-chlorotoluene can be carried out by a rectification method, a molecular sieve adsorption method, a rectification crystallization combination method and the like, the rectification crystallization method has low energy consumption, the, if a falling film freezing crystallization method is adopted, the content of p-chlorotoluene can reach more than 99 percent, the alkylated liquid in the cumene synthesis method is hydrolyzed, neutralized and rectified to obtain cumene and other synthetic raw materials, and finally the synthetic raw materials are stirred under pressure to obtain a final 2-bromo-4-chloro-1-cumene mixture, wherein the cited raw materials and the final mixture have high-efficiency and strong weeding and insecticidal effects, and the pesticide effect is enhanced, so that the aims of strong practicability and good pesticide effect are fulfilled.
Example two:
the synthesis method of the 2-bromo-4-chloro-1-isopropylbenzene comprises the following steps:
1) the synthesis method of the 2-bromopropane comprises the following steps: adding sodium bromide, water, isopropanol and a catalyst into a 250ml four-necked bottle provided with a stirrer, an electric heating jacket, a dropping funnel, a water separator, a thermometer and a condenser according to a certain proportion, slowly dropping a certain amount of concentrated sulfuric acid under stirring, controlling the dropping speed to ensure that the temperature does not exceed 3O ℃, heating to 60 ℃ after dropping, reacting for 1h, heating until a distillate fraction is distilled, keeping reflux until no more distillate is distilled, washing the distillate with distilled water, 10% sodium carbonate and water in sequence, distilling in a distillation flask, collecting a 69 ℃ distillate, and carrying out emergency treatment on the 2-bromopropane in the synthetic process: if leakage emergency treatment, protective measures and emergency measures are taken, 2-bromopropane is inflammable, a ventilated low-temperature and dry environment needs to be kept in the storage and transportation process, and the synthetic reaction mechanism of the 2-bromopropane is as follows:
2) the synthesis method of the 4-chlorotoluene comprises the following steps: toluene dried and dehydrated by salt enters a toluene chlorination reactor after being metered by a metering tank, metered chlorine is introduced from the bottom of the reactor, toluene and chlorine are subjected to benzene ring chlorination by taking ferric chloride as a catalyst at a certain temperature to generate monochlorotoluene chlorination liquid, the chlorination liquid uses nitrogen to drive off residual gas and hydrogen chloride, and then is subjected to rough evaporation to obtain a mixture of p-chlorotoluene and o-chlorotoluene, the ratio of the p-chlorotoluene to the o-chlorotoluene is different along with the difference of the catalyst and reaction conditions, generally the ratio of the p-chlorotoluene to the o-chlorotoluene is 55: 45, the separation of the p-chlorotoluene and the o-chlorotoluene can be realized by a rectification method, a molecular sieve adsorption method, a rectification crystallization method and the like, the rectification crystallization method has low energy consumption, the obtained p-chlorotoluene and o-chlorotoluene have high content, if a falling film freezing crystallization method is adopted, the content of the p-chlorotoluene can reach more than 99 percent, and, the danger of combustion explosion in the case of open fire, violent reaction in contact with the oxidizing agent, combustion (decomposition) of the products: the carbon monoxide, the carbon dioxide and the hydrogen chloride should be made to have anti-leakage emergency work, and the leakage of the 4-chlorotoluene is strictly avoided;
3) the method for synthesizing the isopropyl benzene comprises the following steps: is prepared by the alkylation reaction of benzene and propylene, usually adopts aluminum trichloride as a catalyst and hydrogen chloride as an accelerant, the reaction is carried out at normal pressure and about 95 ℃, besides cumene, polyalkyl byproducts such as diisopropylbenzene, triisopropylbenzene and the like are generated, excessive benzene can be adopted to reduce side reaction, the molar ratio of the benzene to the propylene is about 3, the content of the aluminum trichloride in the reaction liquid is 3-8 percent, the reaction is carried out under low propylene concentration, in order to improve the production capacity of the reactor and reduce the loss of benzene in tail gas, the reaction pressure can be increased to 0.6MPa, the solid (aluminum trichloride and polyisopropylbenzene complex) separated from the alkylated liquid obtained by the reaction after cooling and precipitation is recycled, the alkylated liquid is hydrolyzed, neutralized and rectified to obtain isopropylbenzene, the isopropylbenzene is 3.3-class high-flash-point flammable liquid, and the critical specification is as follows: 33538, UN numbering: 1918, it has no corrosiveness to metal, and can be stored in iron, mild steel, copper or aluminum container, but it is avoided to use rubber product in valve and gasket, and it is low toxicity, can irritate skin and mucous membrane, has strong anesthetic action, causes conjunctivitis and dermatitis, and is harmful to spleen and liver, and can produce accumulation due to slow excretion, and the highest allowable concentration at work site is 491 mg/m;
4) synthesizing: adding 2-bromopropane, 4-chlorotoluene and isopropyl benzene into a reaction kettle, pressurizing and stirring, increasing the reaction pressure to 0.8MPa, and stirring for twenty to thirty minutes.
The invention has the beneficial effects that: the method for synthesizing 2-bromopropane, the method for synthesizing 4-chlorotoluene and the method for synthesizing isopropyl benzene are simplified, the concentration and the extraction rate are improved, a certain amount of concentrated sulfuric acid is slowly dripped under the stirring of the method for synthesizing 2-bromopropane, the dripping speed is controlled, the temperature does not exceed 3O ℃, the dripping is finished, the temperature is raised to 60 ℃ after the dripping is finished, the reaction is carried out for 1h, then the temperature is raised until a fraction is distilled, the reflux is kept until no more fraction is distilled, the distillate is sequentially washed by distilled water, 10 percent sodium carbonate and water, then the distillation is carried out in a distillation flask, the fraction at 69 ℃ is collected, the method for synthesizing 4-chlorotoluene is adopted, the separation of p-chlorotoluene and O-chlorotoluene can be carried out by a rectification method, a molecular sieve adsorption method, a rectification crystallization combination method and the like, the rectification crystallization method has low energy consumption, the, if a falling film freezing crystallization method is adopted, the content of p-chlorotoluene can reach more than 99 percent, the alkylated liquid in the cumene synthesis method is hydrolyzed, neutralized and rectified to obtain cumene and other synthetic raw materials, and finally the synthetic raw materials are stirred under pressure to obtain a final 2-bromo-4-chloro-1-cumene mixture, wherein the cited raw materials and the final mixture have high-efficiency and strong weeding and insecticidal effects, and the pesticide effect is enhanced, so that the aims of strong practicability and good pesticide effect are fulfilled.
The invention has the beneficial effects that: the corresponding emergency treatment needs to be carried out in the synthesis process of the 2-bromopropane: if leakage emergency treatment, protective measures and emergency measures are taken, 2-bromopropane is inflammable, a ventilated low-temperature and dry environment needs to be kept in the storage and transportation process, the synthetic reaction mechanism of 2-bromopropane is that 4-chlorotoluene is inflammable and has the danger of combustion and explosion when meeting open fire, the 4-chlorotoluene can react violently when contacting with an oxidant, and products are combusted (decomposed): carbon monoxide, carbon dioxide and hydrogen chloride, should do emergency work such as preventing leaking, stop 4-chlorotoluene's leakage strictly, cumene is 3.3 class high flash point flammable liquid, danger regulation number: 33538, UN numbering: 1918 it has no corrosiveness to metal, can be stored in iron, mild steel, copper or aluminum container, but it is avoided to use rubber product in valve and gasket, and it is low toxicity, can irritate skin and mucous membrane, has strong anesthetic action, causes conjunctivitis and dermatitis, and is harmful to spleen and liver, and can produce accumulation action due to slow excretion, and the maximum allowable concentration at workplace is 491mg/m, and can effectively ensure the safety of 2-bromo-4-chloro-1-isopropylbenzene in the processing process, and ensure the production safety of 2-bromo-4-chloro-1-isopropylbenzene.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (4)
- The method for synthesizing the 2-bromo-4-chloro-1-isopropylbenzene is characterized by comprising the following steps of:1) the synthesis method of the 2-bromopropane comprises the following steps: adding sodium bromide, water, isopropanol and a catalyst into a 250ml four-necked bottle provided with a stirrer, an electric heating jacket, a dropping funnel, a water separator, a thermometer and a condenser in a ratio, slowly dropwise adding a certain amount of concentrated sulfuric acid under stirring, controlling the dropwise adding speed to ensure that the temperature does not exceed 3O ℃, after the dropwise adding is finished, heating to 50-60 ℃, reacting for 1h, heating until a fraction is distilled, keeping reflux until no fraction is distilled, washing the distillate with distilled water, 10% sodium carbonate and water in sequence, distilling in a distillation flask, and collecting 67-69 ℃ fraction;2) the synthesis method of the 4-chlorotoluene comprises the following steps: toluene dried and dehydrated by salt enters a toluene chlorination reactor after being metered by a metering tank, metered chlorine is introduced from the bottom of the reactor, toluene and chlorine are subjected to benzene ring chlorination by taking ferric chloride as a catalyst at a certain temperature to generate monochlorotoluene chlorination liquid, the chlorination liquid uses nitrogen to drive off residual gas and hydrogen chloride, and then coarse evaporation is carried out to obtain a mixture of p-chlorotoluene and o-chlorotoluene, the ratio of the p-chlorotoluene to the o-chlorotoluene is different along with different catalysts and reaction conditions, generally the ratio of the p-chlorotoluene to the o-chlorotoluene is 55: 45, the p-chlorotoluene and the o-chlorotoluene can be separated by a rectification method, a molecular sieve adsorption method, a rectification crystallization method and the like, the rectification crystallization method has low energy consumption, the obtained p-chlorotoluene and o-chlorotoluene have high content, and the content of the p-chlorotoluene can reach more than 99 percent if a falling film freezing crystallization method is;3) the method for synthesizing the isopropyl benzene comprises the following steps: the alkylation reaction is carried out on benzene and propylene, aluminum trichloride is generally adopted as a catalyst and hydrogen chloride is adopted as an accelerant, the reaction is carried out at normal pressure and about 95 ℃, polyalkyl byproducts such as diisopropylbenzene and triisopropylbenzene are generated in addition to cumene, excessive benzene can be adopted for reducing side reaction, the molar ratio of benzene to propylene is about 3, the content of aluminum trichloride in a reaction liquid is 3% -8%, the reaction is carried out at low propylene concentration, the reaction pressure can be increased to 0.5-0.6MPa for improving the production capacity of a reactor and reducing the loss of benzene in tail gas, the solid (the complex of aluminum trichloride and polyisopropylbenzene) separated from an alkylation liquid obtained by the reaction after cooling and precipitation is recycled, and the cumene is obtained by hydrolyzing, neutralizing and rectifying the alkylation liquid;4) synthesizing: adding 2-bromopropane, 4-chlorotoluene and isopropyl benzene into a reaction kettle, pressurizing and stirring, increasing the reaction pressure to 0.7-0.8MPa, and stirring for twenty-thirty minutes.
- 2. The method for synthesizing 2-bromo-4-chloro-1-isopropylbenzene according to claim 1, wherein the 2-bromopropane is subjected to emergency treatment during the synthesis process: if leakage emergency treatment, protective measures and emergency measures are taken, 2-bromopropane is inflammable, a ventilated low-temperature and dry environment needs to be kept in the storage and transportation process, and the synthetic reaction mechanism of the 2-bromopropane is as follows:
- 3. the process for synthesizing 2-bromo-4-chloro-1-isopropylbenzene according to claim 1, wherein 4-chlorotoluene is flammable and dangerous to be exposed to open fire to cause explosion and explosion, and reacts violently upon contact with an oxidizing agent to burn (decompose) products: the carbon monoxide, the carbon dioxide and the hydrogen chloride should be made to have anti-leakage emergency work, and the leakage of the 4-chlorotoluene is strictly avoided.
- 4. The method for synthesizing 2-bromo-4-chloro-1-isopropylbenzene according to claim 1, wherein the isopropylbenzene is a class 3.3 high flash point flammable liquid, critical specification No.: 33538, UN numbering: 1918, the product has no corrosiveness to metal, can be stored in iron, mild steel, copper or aluminum container, but need avoid using rubber product in valve and gasket, belongs to low toxicity, can irritate skin and mucous membrane, has strong anesthetic action, causes conjunctivitis and dermatitis, and is harmful to spleen and liver, can produce accumulation action due to slow excretion, and has highest allowable concentration of 245.5-491 mg/m at workplace.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4650915A (en) * | 1981-08-11 | 1987-03-17 | Hoechst Aktiengesellschaft | Process for preparing p-chlorotoluene and/or m-chlorotoluene |
| CN104245660A (en) * | 2012-04-26 | 2014-12-24 | 拜尔农科股份公司 | Process for preparing n-(5-chloro-2-isopropylbenzyl)cyclopropanamine |
| RU2016120713A (en) * | 2016-05-26 | 2017-11-30 | федеральное государственное бюджетное образовательное учреждение высшего образования "Самарский государственный технический университет" | METHOD FOR PRODUCING ISOPROPYLBENZENE |
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- 2019-12-16 CN CN201911295976.5A patent/CN111138242A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4650915A (en) * | 1981-08-11 | 1987-03-17 | Hoechst Aktiengesellschaft | Process for preparing p-chlorotoluene and/or m-chlorotoluene |
| CN104245660A (en) * | 2012-04-26 | 2014-12-24 | 拜尔农科股份公司 | Process for preparing n-(5-chloro-2-isopropylbenzyl)cyclopropanamine |
| US20150094492A1 (en) * | 2012-04-26 | 2015-04-02 | Bayer Cropscience Ag | Process for preparing n-(5-chloro-2-isopropylbenzyl)cyclopropanamine |
| RU2016120713A (en) * | 2016-05-26 | 2017-11-30 | федеральное государственное бюджетное образовательное учреждение высшего образования "Самарский государственный технический университет" | METHOD FOR PRODUCING ISOPROPYLBENZENE |
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