CN106431863A - Method for synthesizing isophthalaldehyde - Google Patents
Method for synthesizing isophthalaldehyde Download PDFInfo
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- CN106431863A CN106431863A CN201610815588.5A CN201610815588A CN106431863A CN 106431863 A CN106431863 A CN 106431863A CN 201610815588 A CN201610815588 A CN 201610815588A CN 106431863 A CN106431863 A CN 106431863A
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- synthetic method
- terephthal aldehyde
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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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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for synthesizing isophthalaldehyde. The method includes the following steps that firstly, m-xylene is used for chlorination to synthesize benzyl chloride; secondly, the obtained benzyl chloride is oxidized and hydrolyzed to obtain isophthalaldehyde, wherein an oxidant used in the method is urotropine. The method for synthesizing isophthalaldehyde is easy to operate and low in protection requirement, and raw materials in use are low in price so that the method can be conveniently used and popularized.
Description
Technical field
The invention belongs to field of medicine and chemical technology, it is specifically related to a kind of synthetic method of m-terephthal aldehyde.
Background technology
M-terephthal aldehyde is that a kind of important medicine and chemical intermediate, such as antasthmatic Menglusitena and fluorescence increase
White agent.It is widely used, and the making synthetic method hence for m-terephthal aldehyde is put forward higher requirement.
In current industrial, the main production of m-terephthal aldehyde is：Meta-xylene obtains many benzyl chlorides mixture through chlorination,
Then carry out the oxydrolysises such as nitric acid and obtain m-terephthal aldehyde, as shown in Figure 1.Nitric acid has been used in this kind of method, but for
Nitric acid, its corrosivity is strong, and requirement of shelter is high, inconvenient operation.
Patent US4845305 also discloses that one kind, with m-xylene diamine as raw material, prepares m-terephthal aldehyde with methenamine
Method, as shown in Figure 2.This kind of method flow is simple, and so its raw material adopts m-xylene diamine costly, and inconvenience is promoted.
Therefore for m-terephthal aldehyde, continue to easy operation, and the synthetic method of low requirement of shelter and cheap raw material,
Become people to pursue a goal.
Content of the invention
The technical problem to be solved is to provide a kind of synthetic method of m-terephthal aldehyde, this synthetic method solution
In prior art of having determined, operation requirement of shelter is high, make the above-mentioned problems such as cost of material height.
The technical problem to be solved employs the following technical solutions to realize：
A kind of synthetic method of m-terephthal aldehyde, this synthetic method comprises the following steps：
(1) adopt meta-xylene, carry out chloro, synthesize many benzyl chlorides；
(2) take above-mentioned much benzyl chloride, oxydrolysis, obtain m-terephthal aldehyde；Oxidant wherein used is methenamine.
The present invention further improvement is that：Step (1) is specially：Take meta-xylene in chlorination tank, heat up, be passed through chlorine,
Continuously stirred, it is cooled to room temperature, synthesize many benzyl chlorides.
The present invention further improvement is that：Step (2) is specially：
Stage a, by institute in step (1), much benzyl chloride adds reaction bulb, then adds aqueous solvent, oxidant methenamine,
Stage b, intensification, reaction, cooling, are centrifuged then for the first time；
Stage c, products obtained therefrom after first for stage b centrifugation is added ethanol, temperature rising reflux, cooling, be centrifuged again；
Stage d, it is dried being centrifuged products obtained therefrom again in above-mentioned stage c, obtain product m-terephthal aldehyde.
The present invention further improvement is that：Stage b in step (2), before first centrifugation, warming temperature scope is 50～100
DEG C, reaction duration scope is 8～24h.
The present invention further improvement is that：Stage b in step (2), before first centrifugation, warming temperature scope is 90～100
DEG C, reaction duration scope is 8～10h.
The present invention further improvement is that：Stage b in step (2), is cooled to 5～10 DEG C before first centrifugation.
The present invention further improvement is that：Stage c in step (2), is cooled to 0～5 DEG C before being centrifuged again.
The present invention further improvement is that：Stage d in step (2), baking temperature scope is 50～60 DEG C.
The invention has the beneficial effects as follows：The synthetic method of this kind of m-terephthal aldehyde, easy and simple to handle, requirement of shelter is low, adopts
Raw material cheap, easy to utilize.
Brief description
Fig. 1 is synthetic technology (one) schematic flow sheet of existing m-terephthal aldehyde；
Fig. 2 is synthetic technology (two) schematic flow sheet of existing m-terephthal aldehyde；
Fig. 3 is the synthetic technology schematic flow sheet of m-terephthal aldehyde of the present invention.
Specific embodiment
In order that technological means, creation characteristic, reached purpose and effect that the present invention realizes are easy to understand, tie below
Conjunction is specifically illustrating, and the present invention is expanded on further.
As shown in figure 3, a kind of synthetic method of m-terephthal aldehyde, this synthetic method comprises the following steps：
(1) adopt meta-xylene, carry out chloro, synthesize many benzyl chlorides；
(2) take above-mentioned much benzyl chloride, oxydrolysis, obtain m-terephthal aldehyde；Oxidant wherein used is methenamine.
Specific embodiment one：
(1) chlorination tank taking meta-xylene (1200g, 11.3mol) to add 2L, is warming up to 60 DEG C (less than 80 DEG C), slowly
Slowly it is passed through chlorine, is passed through chlorine (4000g, 56.3mol), continue stirring 1 hour, be cooled to room temperature, obtain the many benzyl chlorides of 2100g.
(2) stage a, take above-mentioned much benzyl chlorides (2100g) to add 3L reaction bulb, add oxidant methenamine
(2100g, 15mol), adds aqueous solvent 2L；
Stage b, be slowly ramped to 50 DEG C, react 24 hours, be cooled to 5 DEG C, first be centrifuged, obtain 900g wet product；
Stage c, first be centrifuged after products obtained therefrom add ethanol (1L), temperature rising reflux 1 hour, be cooled to 0 DEG C, again from
The heart；
Stage d, it is dried being centrifuged products obtained therefrom in above-mentioned c again, baking temperature is 50 DEG C, obtains product isophthalic two
Formaldehyde (530g, yield 35%).
Specific embodiment two：
(1) chlorination tank taking meta-xylene (1200g, 11.3mol) to add 2L, is warming up to 63 DEG C (less than 80 degree), slowly
Slowly it is passed through chlorine, is passed through chlorine (4000g, 56.3mol), continue stirring 1 hour, be cooled to room temperature, obtain the many benzyl chlorides of 2100g.
(2) stage a, take above-mentioned much benzyl chlorides (2100g) to add 3L reaction bulb, add oxidant methenamine
(2100g, 15mol), adds aqueous solvent 2L；
Stage b, be slowly ramped to 75 DEG C, react 17 hours, be cooled to 7 DEG C, first be centrifuged, obtain 1000g wet product；
Stage c, first be centrifuged after products obtained therefrom add ethanol (1L), temperature rising reflux 1 hour, be cooled to 2 DEG C, again from
The heart；
Stage d, it is dried being centrifuged products obtained therefrom in above-mentioned c again, baking temperature is 53 DEG C, obtains product isophthalic two
Formaldehyde (580g, yield 38%).
Specific embodiment three：
(1) chlorination tank taking meta-xylene (1200g, 11.3mol) to add 2L, is warming up to 67 DEG C (less than 80 degree), slowly
Slowly it is passed through chlorine, is passed through chlorine (4000g, 56.3mol), continue stirring 1 hour, be cooled to room temperature, obtain the many benzyl chlorides of 2100g.
(2) stage a, take above-mentioned much benzyl chlorides (2100g) to add 3L reaction bulb, add oxidant methenamine
(2100g, 15mol), adds aqueous solvent 2L；
Stage b, be slowly ramped to 90 DEG C, react 10 hours, be cooled to 8 DEG C, first be centrifuged, obtain 1100g wet product；
Stage c, first be centrifuged after products obtained therefrom add ethanol (1L), temperature rising reflux 1 hour, be cooled to 3 DEG C, again from
The heart；
Stage d, it is dried being centrifuged products obtained therefrom in above-mentioned c again, baking temperature is 56 DEG C, obtains product isophthalic two
Formaldehyde (650g, yield 43%).
Specific embodiment four：
(1) chlorination tank taking meta-xylene (1200g, 11.3mol) to add 2L, is warming up to 70 DEG C (less than 80 degree), slowly
Slowly it is passed through chlorine, is passed through chlorine (4000g, 56.3mol), continue stirring 1 hour, be cooled to room temperature, obtain benzyl chloride more than 2100.
(2) stage a, take above-mentioned much benzyl chlorides (2100g) to add 3L reaction bulb, add oxidant methenamine
(2100g, 15mol), adds aqueous solvent 2L；
Stage b, be slowly ramped to 100 DEG C, react 8 hours, be cooled to 10 DEG C, first be centrifuged, obtain 1200g wet product；
Stage c, first be centrifuged after products obtained therefrom add ethanol (1L), temperature rising reflux 1 hour, be cooled to 5 DEG C, again from
The heart；
Stage d, it is dried being centrifuged products obtained therefrom in above-mentioned c again, baking temperature is 60 DEG C, obtains product isophthalic two
Formaldehyde (720g, yield 47%).
A kind of present invention synthetic method of m-terephthal aldehyde of offer, the synthetic method of this kind of m-terephthal aldehyde, easy and simple to handle,
Requirement of shelter is low, and the raw material of employing is cheap, easy to utilize.
The basic principles, principal features and advantages of the present invention have been shown and described above.The technical staff of the industry should
Understand, the present invention is not restricted to the described embodiments, the simply explanation present invention's described in above-described embodiment and specification is former
Reason, without departing from the spirit and scope of the present invention, the present invention also has various changes and modifications, these changes and improvements
Both fall within scope of the claimed invention.Claimed scope is by appending claims and its equivalent circle.
Fixed.
Claims (8)
1. a kind of synthetic method of m-terephthal aldehyde it is characterised in that：This synthetic method comprises the following steps：
(1) adopt meta-xylene, carry out chloro, synthesize many benzyl chlorides；
(2) take above-mentioned much benzyl chloride, oxydrolysis, obtain m-terephthal aldehyde；Oxidant wherein used is methenamine.
2. a kind of m-terephthal aldehyde according to claim 1 synthetic method it is characterised in that：Step (1) is specially：Take
Meta-xylene, in chlorination tank, heats up, is passed through chlorine, continuously stirred, is cooled to room temperature, synthesizes many benzyl chlorides.
3. a kind of m-terephthal aldehyde according to claim 1 synthetic method it is characterised in that：Step (2) is specially：
Stage a, by institute in step (1), much benzyl chloride adds reaction bulb, then adds aqueous solvent, oxidant methenamine,
Stage b, intensification, reaction, cooling, are centrifuged then for the first time；
Stage c, products obtained therefrom after first for stage b centrifugation is added ethanol, temperature rising reflux, cooling, be centrifuged again；
Stage d, it is dried being centrifuged products obtained therefrom again in above-mentioned stage c, obtain product m-terephthal aldehyde.
4. a kind of m-terephthal aldehyde according to claim 3 synthetic method it is characterised in that：Stage b in step (2),
Before first centrifugation, warming temperature scope is 50～100 DEG C, and reaction duration scope is 8～24h.
5. a kind of m-terephthal aldehyde according to claim 4 synthetic method it is characterised in that：Stage b in step (2),
Before first centrifugation, warming temperature scope is 90～100 DEG C, and reaction duration scope is 8～10h.
6. a kind of m-terephthal aldehyde according to claim 3 synthetic method it is characterised in that：Stage b in step (2),
It is cooled to 5～10 DEG C before first centrifugation.
7. a kind of m-terephthal aldehyde according to claim 3 synthetic method it is characterised in that：Stage c in step (2),
It is cooled to 0～5 DEG C before being centrifuged again.
8. a kind of m-terephthal aldehyde according to claim 3 synthetic method it is characterised in that：Stage d in step (2),
Baking temperature scope is 50～60 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610815588.5A CN106431863A (en) | 2016-09-12 | 2016-09-12 | Method for synthesizing isophthalaldehyde |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610815588.5A CN106431863A (en) | 2016-09-12 | 2016-09-12 | Method for synthesizing isophthalaldehyde |
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| CN106431863A true CN106431863A (en) | 2017-02-22 |
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| CN201610815588.5A Pending CN106431863A (en) | 2016-09-12 | 2016-09-12 | Method for synthesizing isophthalaldehyde |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4328374A (en) * | 1979-07-05 | 1982-05-04 | Mitsubishi Gas Chemical Co., Inc. | Process for the production of aromatic dialdehydes |
| CN102320943A (en) * | 2011-08-03 | 2012-01-18 | 上虞帝瑞云涛化工有限公司 | Preparation method of benzaldehyde |
-
2016
- 2016-09-12 CN CN201610815588.5A patent/CN106431863A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4328374A (en) * | 1979-07-05 | 1982-05-04 | Mitsubishi Gas Chemical Co., Inc. | Process for the production of aromatic dialdehydes |
| CN102320943A (en) * | 2011-08-03 | 2012-01-18 | 上虞帝瑞云涛化工有限公司 | Preparation method of benzaldehyde |
Non-Patent Citations (1)
| Title |
|---|
| 杨明庆: "间二甲苯光氯化合成1，3-苯二甲醛", 《精细石油化工》 * |
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Application publication date: 20170222 |