CN106977381A - The synthesis technique of o-chlorobenzaldehyde - Google Patents
The synthesis technique of o-chlorobenzaldehyde Download PDFInfo
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- CN106977381A CN106977381A CN201710422165.1A CN201710422165A CN106977381A CN 106977381 A CN106977381 A CN 106977381A CN 201710422165 A CN201710422165 A CN 201710422165A CN 106977381 A CN106977381 A CN 106977381A
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- chlorine
- chlorobenzaldehyde
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- chloride
- chlorotolu
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/42—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis
- C07C45/43—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis of >CX2 groups, X being halogen
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- 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
- C07C17/14—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the side-chain of aromatic compounds
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Abstract
The invention discloses the synthesis technique of o-chlorobenzaldehyde, comprise the following steps：Catalytic chlorination under chlorine, illumination condition is passed through in ortho-chlorotolu'ene and obtains chlorated liquid, the amount of material and the ratio of the amount of ortho-chlorotolu'ene material for being passed through chlorine are 2~4:1, the reaction time is 1h~2h, and reaction temperature is 100 DEG C~120 DEG C；By above-mentioned chlorated liquid through vacuum distillation, adjacent chlorobenzyl chloride and ortho-chlorotolu'ene are isolated, the mixed liquor of adjacent chlorine benzyl dichloride and the adjacent benzyl chloride of chlorine three is obtained；Mixed liquor is hydrolyzed using iron chloride and zinc chloride as catalyst and reacts to obtain hydrolyzate, the temperature of hydrolysis is 100 DEG C~120 DEG C, solvent is water, the reaction time is 1.5h~3h；By above-mentioned hydrolyzate, rectification and purification obtains o-chlorobenzaldehyde under vacuum conditions.The technical scheme provided using the present invention further reduces cost, improves product quality；The present invention uses rational catalytic condition, is a process synthetic method preferably afforested, has efficiently controlled the generation of accessory substance, further increases the quality of product.
Description
Technical field
The present invention relates to the synthesis technique of benzaldehyde, and in particular to the synthesis technique of o-chlorobenzaldehyde.
Background technology
O-chlorobenzaldehyde is a kind of important organic synthesis intermediate, mainly for the manufacture of adjacent chlorobenzene first hip, adjacent chlorobenzene first
The primary raw material of the pharmaceuticals such as hip chlorine and cloxacillin sodium, is also widely used in the original that efficient miticide product is manufactured on agricultural chemicals
Material, its market demand is larger.
Synthetic method on o-chlorobenzaldehyde has chlorinolysis, direct oxidation method and indirect oxidation method, at present industry
It is upper most commonly seen for chlorinolysis.Classical chlorinated hydrolysis technique is again through urging by ortho-chlorotolu'ene chlorination into adjacent chlorine benzyl dichloride
Change is hydrolyzed into o-chlorobenzaldehyde, but in chlorination process in addition to the adjacent chlorine benzyl dichloride for having 80%, the byproduct that there is also about 20% is adjacent
The benzyl chloride of chlorine three, in process of production the adjacent benzyl chloride of chlorine three can hydrolyze generation 0-chloro-benzoic acid, 0-chloro-benzoic acid separation, purification difficulty
Greatly, the wastewater flow rate generated in purification process is also more, and the raw materials technology unit consumption is of a relatively high, and production cost is not very good, but
Relatively other its advantage of technique are more apparent.
The content of the invention
The problem to be solved in the present invention is using existing chloride oxidation method production o-chlorobenzaldehyde complex process, purification
Difficulty is big, causes production cost high.
To solve the above problems, the technical solution adopted by the present invention specifically includes following steps：
(1) catalytic chlorination under chlorine, illumination condition is passed through in ortho-chlorotolu'ene and obtains chlorated liquid, the amount of the material of chlorine is passed through
Ratio with the amount of ortho-chlorotolu'ene material is 2~4:1, the reaction time is 1h~2h, and reaction temperature is 100 DEG C~120 DEG C；
(2) by above-mentioned chlorated liquid through vacuum distillation, adjacent chlorobenzyl chloride and ortho-chlorotolu'ene are isolated, adjacent chlorine benzyl dichloride and adjacent chlorine is obtained
The mixed liquor of three benzyl chlorides；
(3) above-mentioned mixed liquor is hydrolyzed using iron chloride and zinc chloride as catalyst and reacts to obtain hydrolyzate, hydrolysis
Temperature be 100 DEG C~120 DEG C, the reaction time be 1.5h~3h；
(4) by above-mentioned hydrolyzate, rectification and purification obtains o-chlorobenzaldehyde under vacuum conditions.
In step (1), ortho-chlorotolu'ene and chlorine reaction first generate adjacent chlorobenzyl chloride, and adjacent chlorobenzyl chloride is given birth to chlorine reaction again
Into the adjacent chlorine benzyl dichloride of target compound, over time and chlorine input, adjacent chlorine benzyl dichloride continues to generate with chlorine reaction
The adjacent benzyl chloride of chlorine three.For the formation of the adjacent benzyl chloride of chlorine three of control, by controlling the generation of adjacent chlorine benzyl dichloride, the adjacent benzyl chloride of chlorine three of impurity is reduced
Generation, under the reaction conditions, the amount of the adjacent benzyl chloride of chlorine three is 55%-65%, and the amount of the adjacent benzyl chloride of chlorine three is less than 2%, remaining
For adjacent chlorobenzyl chloride and a small amount of unreacted ortho-chlorotolu'ene, it is easy to the vacuum distillation in step 2 to separate.When reaction temperature is more than 120
DEG C when, form the speed of the adjacent benzyl chloride of chlorine three, therefore, chlorination reaction temperature control is more satisfactory below 120 DEG C.Step
(3) in hydrolysis, when reaction temperature is higher than 130 DEG C, there is coking phenomenon in reaction, causes product yield to reduce.
The content of catalyst is the 0.1%~0.6% of mixed liquor quality, wherein iron chloride and chlorination in above-mentioned steps (3)
The ratio of the amount of zinc material is 0.5~1.5:1.Catalyst iron chloride, zinc chloride are both hydrolyst, while being polymerisation again
Catalyst, catalyst amount cross conference increase side reaction product, make polymerization tar increase, so as to influence the receipts of hydrolysis
Rate, catalyst amount is too small, it is difficult to initiation reaction, even if triggering, reaction speed is also very slow, and the reaction time is oversize, unfavorable
In being normally carried out for reaction.
Vacuum in step (4) is -0.1~-0.08MPa.Under conditions of the vacuum, rectification yield is higher, is
Comparatively ideal vacuum in rectifying.
Further, the adjacent chlorobenzyl chloride and ortho-chlorotolu'ene isolated in step (2) are passed through to the ortho-chlorotolu'ene in step (1)
It is middle to repeat to react.The adjacent chlorobenzyl chloride and ortho-chlorotolu'ene isolated return to chlorination, are so both effectively utilized ortho-chlorotolu'ene, again
Chlorine water has been saved, production cost has been saved, makes chlorinated hydrolysis technique more reasonable.
Further, in above-mentioned steps (1) in raw material ortho-chlorotolu'ene, water content is less than 0.5%.Due to industrial raw material
In have certain moisture content, in order to be more conducive to industrialized production, the present invention have studied in the presence of a small amount of moisture content to this reaction
Influence, when water content is more than 0.5%, the content increase of the adjacent benzyl chloride of chlorine three therefore need to control water content below 0.5%.
In above-mentioned steps (1), the content of metal ion is less than 0.02%.Influence of the micro metal ion to chlorination reaction
Very big, when metal impurities total amount is more than 0.06%, the chlorination reaction on phenyl ring is significantly increased, therefore strictly controls metal ion
Total amount, it is smaller on the influence of the result of chlorination reaction when metal ion control is below 0.02%.
Compared with prior art, the beneficial effects of the present invention are：The technical scheme provided using the present invention is further dropped
Low cost, improves product quality；The present invention uses rational catalytic condition, is a process synthetic method preferably afforested；
Rational chlorination temperature, hydrolysis temperature and the vacuum of rectifying are have studied, the generation of accessory substance has been efficiently controlled, has further carried
The high quality of product.
Embodiment
For a better understanding of the present invention, the present invention is further illustrated with reference to embodiment.
Embodiment 1
900g ortho-chlorotolu'enes are weighed in four-hole bottle, are stirred under illumination, temperature control is 100 DEG C, chlorine is passed through, 2h is reacted
It is 36.13% to obtain adjacent chlorobenzyl chloride content in chlorated liquid, the chlorated liquid, adjacent chlorine benzyl dichloride 62.30%, and the adjacent benzyl chloride of chlorine three is
1.11%, the chlorizate on phenyl ring is 0.36%.Above-mentioned chlorated liquid is heated to boiling at reduced pressure conditions, adjacent chlorine chlorine is isolated
Benzyl, when adjacent chlorobenzyl chloride content is less than 1%, stops heating, the mixed liquor of residual is given over into hydrolysis.Above-mentioned Liquid Residue is added
Enter to hydrolyze in flask, it is 110 DEG C to control temperature, stirring is lower to add catalyst iron chloride, the wherein aqueous solution of aluminium chloride, catalyst
Consumption is the 0.015% of mixed liquor quality, reacts 2.5h, hydrogen chloride gas is released when reaction starts, is passed through in water and obtains hydrochloric acid, should
The yield of step reaction is 92.5%.Reaction terminate after, add 20% aqueous sodium carbonate to reaction solution pH value 8~10 it
Between, 30min is stirred, standing separation goes out the o-chlorobenzaldehyde crude product of oily, then obtain the adjacent chlorobenzene first of target product through rectification under vacuum
Aldehyde, vacuum is -0.090MPa, and product purity is 99.5%.
Embodiment 2
900g ortho-chlorotolu'enes are weighed in four-hole bottle, are stirred under illumination, temperature control is 110 DEG C, is passed through chlorine, are reacted
1.5h obtains chlorated liquid, and adjacent chlorobenzyl chloride content is 38.3% in the chlorated liquid, adjacent chlorine benzyl dichloride 60.6%, and the adjacent benzyl chloride of chlorine three is
1.1%.Above-mentioned chlorated liquid is heated to boiling at reduced pressure conditions, adjacent chlorobenzyl chloride is isolated, when adjacent chlorobenzyl chloride content is less than 1%
When, stop heating, the mixed liquor of residual is given over into hydrolysis.It is by temperature in above-mentioned Liquid Residue addition hydrolysis flask, is controlled
120 DEG C, stirring is lower to add catalyst iron chloride, the aqueous solution of aluminium chloride, and wherein catalyst amount is mixed liquor quality
0.02%, 2h is reacted, hydrogen chloride gas is released when reaction starts, be passed through in water and obtain hydrochloric acid, the yield of step reaction is 96.1%.
After reaction terminates, the aqueous sodium carbonate of addition 20% between 8~10, stirs 30min to reaction solution pH value, and standing separation goes out
The o-chlorobenzaldehyde crude product of oily, then obtains target product o-chlorobenzaldehyde through rectification under vacuum, and vacuum is -0.085MPa, production
Product purity is 99.4%.
Embodiment 3
900g ortho-chlorotolu'enes are weighed in four-hole bottle, are stirred under illumination, temperature control is 120 DEG C, is passed through chlorine, are reacted
100min obtains chlorated liquid, and adjacent chlorobenzyl chloride content is 39.2% in the chlorated liquid, adjacent chlorine benzyl dichloride 58.7%, and the adjacent benzyl chloride of chlorine three is
2.1%.Above-mentioned chlorated liquid is heated to boiling at reduced pressure conditions, adjacent chlorobenzyl chloride is isolated, when adjacent chlorobenzyl chloride content is less than 1%
When, stop heating, the mixed liquor of residual is given over into hydrolysis, adjacent chlorobenzyl chloride is reused as raw material, re-starts one
The chlorination reaction of step is used to generate adjacent chlorine benzyl dichloride.Above-mentioned Liquid Residue is added in hydrolysis flask, it is 100 DEG C to control temperature, is stirred
Lower addition catalyst iron chloride, the aqueous solution of aluminium chloride are mixed, wherein catalyst amount is the 0.01% of mixed liquor quality, reaction
3h, hydrogen chloride gas is released when reaction starts, and is passed through in water and is obtained hydrochloric acid, and the income of step reaction is 90.3%.After reaction terminates,
The aqueous sodium carbonate of addition 20% between 8~10, stirs 30min to reaction solution pH value, and standing separation goes out the adjacent chlorine of oily
Benzaldehyde crude product, then obtains target product o-chlorobenzaldehyde through rectification under vacuum, and vacuum is -0.082MPa, and product purity is
99.1%.
Embodiment 4
900g ortho-chlorotolu'enes are weighed in four-hole bottle, are stirred under illumination, temperature control is 110 DEG C, is passed through chlorine, are reacted
120min obtains chlorated liquid, and adjacent chlorobenzyl chloride content is 36.7% in the chlorated liquid, adjacent chlorine benzyl dichloride 60.6%, and the adjacent benzyl chloride of chlorine three is
2.7%.Above-mentioned chlorated liquid is heated to boiling at reduced pressure conditions, adjacent chlorobenzyl chloride is isolated, when adjacent chlorobenzyl chloride content is less than 1%
When, stop heating, the mixed liquor of residual is given over into hydrolysis, adjacent chlorobenzyl chloride is reused as raw material, re-starts one
The chlorination reaction of step is used to generate adjacent chlorine benzyl dichloride.Above-mentioned Liquid Residue is added in hydrolysis flask, it is 130 DEG C to control temperature, is stirred
Lower addition catalyst iron chloride, the aqueous solution of aluminium chloride are mixed, wherein catalyst amount is the 0.02% of mixed liquor quality, reaction
1.5h, hydrogen chloride gas is released when reaction starts, and is passed through in water and is obtained hydrochloric acid, and the income of step reaction is 84%.After reaction terminates,
The aqueous sodium carbonate of addition 20% between 8~10, stirs 30min to reaction solution pH value, and standing separation goes out the adjacent chlorine of oily
Benzaldehyde crude product, then obtains target product o-chlorobenzaldehyde through rectification under vacuum, and vacuum is -0.085MPa, and product purity is
98.9%.
Above-described embodiment is only preferred embodiment, not to the restriction of embodiment.For the common of art
For technical staff, it can also make other changes in different forms on the basis of the above description.It is all according to the present invention
The equivalent changes and modifications that the content of claim is made, all should be used as the technology category of the present invention.
Claims (6)
1. a kind of synthesis technique of o-chlorobenzaldehyde, it is characterised in that comprise the following steps：
(1) catalytic chlorination under chlorine, illumination condition is passed through in ortho-chlorotolu'ene and obtains chlorated liquid, amount and the neighbour of the material of chlorine is passed through
The ratio of the amount of chlorotoluene material is 2~4:1, the reaction time is 1h~2h, and reaction temperature is 100 DEG C~120 DEG C；
(2) by above-mentioned chlorated liquid through vacuum distillation, adjacent chlorobenzyl chloride and ortho-chlorotolu'ene are isolated, adjacent chlorine benzyl dichloride and adjacent chlorine trichlorine is obtained
The mixed liquor of benzyl；
(3) above-mentioned mixed liquor is hydrolyzed using iron chloride and zinc chloride as catalyst and reacts to obtain hydrolyzate, the temperature of hydrolysis
Spend for 100 DEG C~120 DEG C, the reaction time is 1.5h~3h；
(4) by above-mentioned hydrolyzate, rectification and purification obtains o-chlorobenzaldehyde under vacuum conditions.
2. the synthesis technique of o-chlorobenzaldehyde as claimed in claim 1, it is characterised in that the content of catalyst is in step (3)
The ratio of the amount of the 0.1%~0.6% of mixed liquor quality, wherein iron chloride and chlorination zinc material is 0.5~1.5:1.
3. the synthesis technique of o-chlorobenzaldehyde as claimed in claim 1, it is characterised in that the vacuum in step (4) is -0.1
~-0.08MPa.
4. the synthesis technique of o-chlorobenzaldehyde as claimed in claim 1, it is characterised in that the adjacent chlorine that will be isolated in step (2)
Benzyl chloride and ortho-chlorotolu'ene, which are passed through in the ortho-chlorotolu'ene in step (1), to be repeated to react.
5. the synthesis technique of o-chlorobenzaldehyde as claimed in claim 1, it is characterised in that in step (1), metal ion contains
Amount is less than 0.02%.
6. the synthesis technique of o-chlorobenzaldehyde as claimed in claim 1, it is characterised in that raw material ortho-chlorotolu'ene in step (1)
In, moisture is less than 0.5%.
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| CN201710422165.1A CN106977381A (en) | 2017-06-07 | 2017-06-07 | The synthesis technique of o-chlorobenzaldehyde |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108794311A (en) * | 2018-07-17 | 2018-11-13 | 常州大学 | A kind of method that ortho-chlorotolu'ene continuous oxidation prepares o-chlorobenzaldehyde |
| CN113072418A (en) * | 2021-03-04 | 2021-07-06 | 老河口华辰化学有限公司 | Production method for double-kettle switching continuous chlorination |
| CN113105302A (en) * | 2021-03-04 | 2021-07-13 | 老河口华辰化学有限公司 | Method for co-production of o-chlorobenzyl chloride, o-dichlorobenzyl chloride and o-chlorotrifluorobenzyl chloride by chlorination of o-chlorotoluene |
| CN113292408A (en) * | 2021-05-28 | 2021-08-24 | 湖北源洹实业投资有限公司 | Process for producing o-chlorobenzaldehyde by chlorination distillation method |
| CN113429255A (en) * | 2021-06-25 | 2021-09-24 | 常州新东化工发展有限公司 | Continuous production process for co-production of monochlorobenzyl chloride, monochlorobenzaldehyde and monochlorobenzoic acid |
| CN114195635A (en) * | 2021-11-30 | 2022-03-18 | 江西永通科技股份有限公司 | Synthesis method of o-trifluoromethyl benzoyl chloride |
| CN115215738A (en) * | 2022-08-23 | 2022-10-21 | 柳州东风容泰化工股份有限公司 | Preparation method of p-chlorobenzaldehyde |
| CN116789535A (en) * | 2023-08-28 | 2023-09-22 | 山东道可化学有限公司 | Method for preparing o (p) chlorobenzaldehyde by continuous chloridizing and hydrolyzing o (p) chlorotoluene |
| CN117586118A (en) * | 2024-01-18 | 2024-02-23 | 山东道可化学有限公司 | Recovery method of o (p) chlorobenzoic acid as byproduct of o (p) chlorobenzaldehyde |
-
2017
- 2017-06-07 CN CN201710422165.1A patent/CN106977381A/en active Pending
Non-Patent Citations (1)
| Title |
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| 杨晓辉: "邻氯苯甲醛合成新工艺的研究", 《中国优秀博硕士学位论文全文数据库(硕士) 工程科技Ⅰ辑（季刊）》 * |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108794311A (en) * | 2018-07-17 | 2018-11-13 | 常州大学 | A kind of method that ortho-chlorotolu'ene continuous oxidation prepares o-chlorobenzaldehyde |
| CN113072418A (en) * | 2021-03-04 | 2021-07-06 | 老河口华辰化学有限公司 | Production method for double-kettle switching continuous chlorination |
| CN113105302A (en) * | 2021-03-04 | 2021-07-13 | 老河口华辰化学有限公司 | Method for co-production of o-chlorobenzyl chloride, o-dichlorobenzyl chloride and o-chlorotrifluorobenzyl chloride by chlorination of o-chlorotoluene |
| CN113105302B (en) * | 2021-03-04 | 2024-01-12 | 老河口华辰化学有限公司 | Method for co-production of o-chlorobenzyl chloride, o-chlorobenzyl dichloride and o-chlorobenzyl trichloride through o-chlorotoluene chlorination |
| CN113292408A (en) * | 2021-05-28 | 2021-08-24 | 湖北源洹实业投资有限公司 | Process for producing o-chlorobenzaldehyde by chlorination distillation method |
| CN113429255A (en) * | 2021-06-25 | 2021-09-24 | 常州新东化工发展有限公司 | Continuous production process for co-production of monochlorobenzyl chloride, monochlorobenzaldehyde and monochlorobenzoic acid |
| CN114195635A (en) * | 2021-11-30 | 2022-03-18 | 江西永通科技股份有限公司 | Synthesis method of o-trifluoromethyl benzoyl chloride |
| CN115215738A (en) * | 2022-08-23 | 2022-10-21 | 柳州东风容泰化工股份有限公司 | Preparation method of p-chlorobenzaldehyde |
| CN116789535A (en) * | 2023-08-28 | 2023-09-22 | 山东道可化学有限公司 | Method for preparing o (p) chlorobenzaldehyde by continuous chloridizing and hydrolyzing o (p) chlorotoluene |
| CN117586118A (en) * | 2024-01-18 | 2024-02-23 | 山东道可化学有限公司 | Recovery method of o (p) chlorobenzoic acid as byproduct of o (p) chlorobenzaldehyde |
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Application publication date: 20170725 |