CN104230704A - Method for synthesizing isophthalyl/terehthaloyl chloride through photochlorination - Google Patents
Method for synthesizing isophthalyl/terehthaloyl chloride through photochlorination Download PDFInfo
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- CN104230704A CN104230704A CN201410517280.3A CN201410517280A CN104230704A CN 104230704 A CN104230704 A CN 104230704A CN 201410517280 A CN201410517280 A CN 201410517280A CN 104230704 A CN104230704 A CN 104230704A
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- phthaloyl chloride
- dimethylbenzene
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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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/64—Separation; Purification; Stabilisation; Use of additives
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Abstract
The invention relates to a synthesis method of isophthalyl/terehthaloyl chloride and belongs to the techncial field of organic synthesis methods. The synthesis method comprises the following steps: 1) introducing chlorine into chlorination equipment in which xylene is filled and carrying out photochlorination reaction under the radiation of a light source; 2), filling isophthalic/terephthalic acid into a reactor, continuously filling lewis acid, then transferring an xylene hexachloride crude product in step 1) from a degassing reactor into the reactor, continuously stirring and raising the temperature, when the quantity of air bubbles in the reactor is reduced, raising the temperature until no air bubbles are produced, and stopping heating after reaction is over to obtain an isophthalyl/terehthaloyl chloride crude product; 3), conveying the isophthalyl/terehthaloyl chloride crude product obtained in step 2) to a distilling tower to carry out pressure reduction and distilling, collecting tower top fractions in the distilling process to be detected, and collecting the finished product when the content of the isophthalyl/terehthaloyl chloride is detected to be larger than 99.90%. The synthesis method has the advantages of low equipment investment, low cost and high yield.
Description
Technical field
The present invention relates to the synthetic method of a kind of/p-phthaloyl chloride, belong to methodology of organic synthesis technical field.
Background technology
M-phthaloyl chloride and p-phthaloyl chloride have extensive use in Industrial materials, electrical apparatus insulation material, protective clothing and house decorative material etc.Main as raw materials such as the paint polymeric amide that disappears, aromatic polyimide laminating material, permeable membrane material, polymer class properties-correcting agent, dyestuffs at present, it is also the intermediate of synthetic pesticide and medicine industry.
Between current industrial production/method of p-phthaloyl chloride in, most widely used be with/terephthalic acid is for raw material, react with chlorizating agent under catalysts conditions, chlorizating agent selects sulfur oxychloride, phosgene or trichloromethylchloroformate etc. usually, wherein general with sulfur oxychloride method.To be CN102516060A and publication number be the patent No. discloses respectively in the patent of invention of CN1562946 with sulfur oxychloride photoreactive gas as the technique of m-phthaloyl chloride prepared by chlorizating agent.With/production technique that terephthalic acid is raw material, be widely used, but production cost is high.
Summary of the invention
The object of the invention is to solve the weak point that above-mentioned prior art exists, provide a kind of facility investment few, with low cost, yield is high, between the Light chlorimation synthesis that quality product can reach more than 99.90%/and the method for p-phthaloyl chloride.
Between Light chlorimation synthesis/and the method for p-phthaloyl chloride, its special character is to comprise the following steps:
1, the synthesis of chlordene dimethylbenzene
Dimethylbenzene is put in chlorination plant, be heated to more than 80 DEG C, under the irradiation of light source, chlorine is continued to be passed in chlorination plant, under 80 DEG C of-130 DEG C of temperature of reaction, carries out optical chlorinating reaction, by complete for the methyl of dimethylbenzene side chain chlorination, obtain chlordene dimethylbenzene, for m-xylene, concrete equation is:
Wherein light source can take fluorescent lamp, mercury lamp, ultraviolet lamp etc., preferred ultraviolet lamp, and optical source wavelength scope is at 300nm-600nm, and the mass ratio that feeds intake of dimethylbenzene and chlorine is 1:(4-4.8).Produce hydrogen chloride tail gas in reaction process, need control between vacuum tightness 730mmHg-750mmHg, to get rid of tail gas.
The principle of this step optical chlorinating reaction is, first under ultraviolet effect, chlorine homolysis is made to form chlorine radicals, this radical captures the hydrogen atom on the monomethyl in m-xylene, generate hydrogenchloride molecule and m-xylene radical, the new radical formed continue with chlorine reaction after, change methyl chloride benzyl and a chlorine radicals into, this propagation process continues to go on, through six circulation radical substitution reactions repeatedly, until hydrogen atoms all on methyl replace by chlorine atom, hydrogen atom finally on all methyl is all substituted, generate unstable chlordene m-xylene crude product.
2, the synthesis of acyl chlorides
By the chlordene dimethylbenzene crude product of upper step and/terephthalic acid is put in reactor, add catalyzer Lewis acid, continuous stirring heats up, make temperature remain on 50 DEG C-60 DEG C, and control certain vacuum tightness, when the bubbles volume in reactor reduces, raised temperature to 100 DEG C, until when bubble-free produces, reaction terminates to stop heating, to obtain between obtaining/p-phthaloyl chloride crude product.For the concrete equation of m-phthaloyl chloride be:
This step reacting middle catalyst chooses the Lewis acid such as iron trichloride, zinc chloride, and control the vacuum tightness of reaction between 730mmHg-750mmHg, the tail gas that reaction produces enters exhaust treatment system with the tail gas produced in the first step.
3, acyl chlorides is refining
Finally carry out the refining of acyl chlorides, by between crude product/p-phthaloyl chloride carries out rectification under vacuum and obtains fine work acyl chlorides, the vacuum degree control of rectification under vacuum operation is in 0.01-10mmHg(absolute pressure), for m-phthaloyl chloride, concrete operations are for be delivered in rectifying tower by crude product m-phthaloyl chloride, when liquid level in tower arrives 65-75%, stop charging, control vacuum tightness and carry out tower top total reflux operation between 0.01-10mmHg, when tower top temperature rises to 105 DEG C, column bottom temperature is kept to be 130 DEG C-140 DEG C, collect overhead fraction, each hr collections overhead fraction detects, as isophthaloyl cl content >99.90%, carry out the collection of finished product, when collecting m-phthaloyl chloride finished product, improve tower top temperature to 110-115 DEG C, maintenance column bottom temperature is 130-140 DEG C, when overhead fraction isophthaloyl cl content is less than 99.90%, stop the collection of m-phthaloyl chloride and stop heating.
Between Light chlorimation of the present invention synthesis/method of p-phthaloyl chloride, technique is simple and direct, facility investment is few, in acyl chlorides building-up process of the present invention, by chlordene dimethylbenzene crude product and/terephthalic acid is put in reactor, add catalyzer Lewis acid to react, to make between an amount/terephthalic acid generates the acyl chlorides of two amount of substances, and prior art adopt between/terephthalic acid can only produce the acyl chlorides of an amount of substance with chlorizating agent, such cost will reduce greatly, and the present invention adopts chlordene dimethylbenzene crude material directly to carry out the synthesis of phenylformic acid chlorine, method is simple, raw material is cheap and easy to get, equipment investment amount is few, energy-saving and cost-reducing, and after the recycling of the refining and product of postmenstruation, constant product quality, between obtained/p-phthaloyl chloride purity can up to more than 99. 90%, yield is high, cost is low.
Embodiment
Below provide the specific embodiment of the present invention, be used for that the present invention is described further.
Embodiment 1
The method of the Light chlorimation synthesis m-phthaloyl chloride of the present embodiment, concrete steps are:
1, the m-xylene of 1000Kg is put in chlorination tower, open chlorination tower heating unit, material in chlorination tower is made to rise to 80 DEG C, open ultraviolet source in chlorination tower, and open chlorine pipeline valve, chlorine to be contacted with material by chlorine gas distributor through under meter and side-chain chlorination occurs, by controlling chlorination tower interchanger bottom chlorination tower, making temperature of reaction maintain 80 DEG C-130 DEG C, stopping logical chlorine when being passed into when quality of chlorine gas reaches 4000Kg.
Control vacuum tightness in reaction process at 740mmHg, the tail gas of generation comprises hydrogenchloride, and the chlorine that a small amount of unreacted is complete enters into exhaust treatment system by condenser, obtains hydrochloric acid.
Be transferred to by material in degassed still after having reacted, control vacuum tightness at 50mmHg, to remove hydrogenchloride in material and chlorine, finally obtain 2894Kg chlordene m-xylene, principal constituent content is 99%, and yield is 98%.
2,800Kg m-phthalic acid is put in acidolysis reaction still, drop into iron trichloride 8Kg again, then the chlordene m-xylene in step 1 being got 1455Kg is transferred in acidolysis reaction still by degassed still, heats up under whipped state, makes temperature maintain 50 DEG C-60 DEG C for some time, controlling vacuum tightness is 740 mmHg, when the bubbles volume in reactor reduces, raised temperature to 100 DEG C, when bubble-free produces, reaction terminates to stop heating, obtains crude acid chloride.
3, the m-phthaloyl chloride crude product in step 2 is forwarded in rectifying still, control vacuum tightness at 0.01-10mmHg, open the heating of thermal oil valve, carry out tower top total reflux operation, when tower top temperature rises to 105 DEG C, keep column bottom temperature to be 130 DEG C-140 DEG C, collect overhead fraction, each hr collections overhead fraction detects, and as isophthaloyl cl content >99.90%, carries out the collection of finishing room phthalyl chloride finished product.When collecting finished product m-phthaloyl chloride, improve tower top temperature to 110-115 DEG C, maintenance column bottom temperature is 130-140 DEG C, when overhead fraction isophthaloyl cl content is less than 99.90%, stops the collection of m-phthaloyl chloride and stops heating.Receive to obtain acyl chlorides finished product 1860Kg altogether, acyl chlorides yield is 95%, content 99.94%.
Embodiment 2
The method of the Light chlorimation synthesis p-phthaloyl chloride of the present embodiment, concrete steps are:
1, the p-Xylol of 800Kg is put in chlorination tower, open chlorination tower heating unit, material in chlorination tower is made to rise to 90 DEG C, open ultraviolet source in chlorination tower, and open chlorine pipeline valve, chlorine to be contacted with material by chlorine gas distributor through under meter and side-chain chlorination occurs, by controlling chlorination tower interchanger bottom chlorination tower, making temperature of reaction maintain 90 DEG C-130 DEG C, stopping logical chlorine when being passed into when quality of chlorine gas reaches 3840Kg.
Control vacuum tightness in reaction process at 730mmHg, the tail gas of generation comprises hydrogenchloride, and the chlorine that a small amount of unreacted is complete enters into exhaust treatment system by condenser, obtains hydrochloric acid.
Be transferred to by material in degassed still after having reacted, control vacuum tightness at 50mmHg, to remove hydrogenchloride in material and chlorine, finally obtain 2244Kg hexachloroparaxylene (HPX), principal constituent content is 98%, and yield is 95%.
2,1000Kg terephthalic acid is put in acidolysis reaction still, drop into iron trichloride 20Kg again, then the hexachloroparaxylene (HPX) in step 1 being got 2000Kg is transferred in acidolysis reaction still by degassed still, heats up, make temperature maintain 60 DEG C of for some time under whipped state, controlling vacuum tightness is 740 mmHg, when the bubbles volume in reactor reduces, raised temperature to 110 DEG C, when bubble-free produces, reaction terminates to stop heating, obtains p-phthaloyl chloride crude product.
3, p-phthaloyl chloride crude product is forwarded in rectifying still, control vacuum tightness at below 10mmHg, open the heating of thermal oil valve, carry out tower top total reflux operation, when tower top temperature rises to 105 DEG C, keep column bottom temperature to be 130 DEG C-140 DEG C, collect overhead fraction, each hr collections overhead fraction detects, and as content >99.90%, carries out the collection of finished product p-phthaloyl chloride finished product.When collecting finished product m-phthaloyl chloride, improve tower top temperature to 110-115 DEG C, maintenance column bottom temperature is 130-140 DEG C, when overhead fraction isophthaloyl cl content is less than 99%, stops the collection of p-phthaloyl chloride and stops heating.Receive to obtain p-phthaloyl chloride finished product 2298Kg altogether, the yield 94% of acyl chlorides, paraphenylene terephthalamide's cl content 99.95%.
Embodiment 3
The method of the Light chlorimation synthesis m-phthaloyl chloride of the present embodiment, concrete steps are:
1, the m-xylene of 700Kg is put in chlorination tower, open chlorination tower heating unit, material in chlorination tower is made to rise to 80 DEG C, open ultraviolet source in chlorination tower, and open chlorine pipeline valve, chlorine to be contacted with material by chlorine gas distributor through under meter and side-chain chlorination occurs, by controlling chlorination tower interchanger bottom chlorination tower, making temperature of reaction maintain 85 DEG C-130 DEG C, stopping logical chlorine when being passed into when quality of chlorine gas reaches 3150Kg.
Control vacuum tightness in reaction process at 750mmHg, the tail gas of generation comprises hydrogenchloride, and the chlorine that a small amount of unreacted is complete enters into exhaust treatment system by condenser, obtains hydrochloric acid.
Be transferred to by material in degassed still after having reacted, control vacuum tightness at 50mmHg, to remove hydrogenchloride in material and chlorine, finally obtain 1978Kg chlordene m-xylene, principal constituent content is 99%, and yield is 96%.
2,600Kg m-phthalic acid is put in acidolysis reaction still, drop into iron trichloride 6Kg again, then the chlordene m-xylene in step 1 being got 1200Kg is transferred in acidolysis reaction still by degassed still, heats up under whipped state, makes temperature maintain 50 DEG C-60 DEG C for some time, controlling vacuum tightness is 740 mmHg, when the bubbles volume in reactor reduces, raised temperature to 100 DEG C, when bubble-free produces, reaction terminates to stop heating, obtains crude acid chloride.
3, the m-phthaloyl chloride crude product in step 2 is forwarded in rectifying still, control vacuum tightness at 0.01-10mmHg, open the heating of thermal oil valve, carry out tower top total reflux operation, when tower top temperature rises to 105 DEG C, keep column bottom temperature to be 130 DEG C-140 DEG C, collect overhead fraction, each hr collections overhead fraction detects, and as isophthaloyl cl content >99.90%, carries out the collection of finishing room phthalyl chloride finished product.When collecting finished product m-phthaloyl chloride, improve tower top temperature to 110-115 DEG C, maintenance column bottom temperature is 130-140 DEG C, when overhead fraction isophthaloyl cl content is less than 99%, stops the collection of m-phthaloyl chloride and stops heating.Receive to obtain acyl chlorides finished product 1408Kg altogether, acyl chlorides yield is 96%, content 99.96%.
Above-described embodiment is only be described the preferred embodiment of the present invention, not right
Scope of the present invention sets, and under the prerequisite not departing from spirit of the present invention, the distortion that those of ordinary skill in the art do technical scheme of the present invention and improvement, all should fall in protection domain that claims of the present invention determine.
Claims (10)
1. the method for p-phthaloyl chloride between Light chlorimation synthesis, is characterized in that comprising the following steps:
1), the synthesis of chlordene dimethylbenzene
Being passed into by chlorine is equipped with in the chlorination plant of dimethylbenzene, under the irradiation of light source, carry out optical chlorinating reaction, by complete for the methyl of dimethylbenzene side chain chlorination, obtains chlordene dimethylbenzene crude product, will carry out vacuum degree control in reaction process to chlorination tower;
2), the synthesis of acyl chlorides
Between inciting somebody to action/terephthalic acid is put in reactor, drop into Lewis acid again, then the chlordene dimethylbenzene crude product in step 1) is transferred in reactor by degassed still, constantly stirs intensification, make temperature remain on 50 DEG C-60 DEG C, when the bubbles volume in reactor reduces, raised temperature to 100 DEG C, until when bubble-free produces, reaction terminates to stop heating, between obtaining/and p-phthaloyl chloride crude product, vacuum degree control to be carried out to reactor in reaction process;
3), acyl chlorides is refining
Between step 2 is obtained/p-phthaloyl chloride crude product is delivered in rectifying tower and carries out underpressure distillation, in still-process, collect overhead fraction to detect, when between detecting/paraphenylene terephthalamide's cl content be greater than 99.90% time, carry out the collection of finished product, along with the carrying out of distillation reaction, when detecting in the middle of overhead fraction/paraphenylene terephthalamide's cl content is when being less than 99.90%, between stopping/collection of p-phthaloyl chloride stop heating.
2., according to the method for p-phthaloyl chloride between a kind of Light chlorimation synthesis according to claim 1, it is characterized in that the wavelength region of light source described in step 1) is at 300nm-600nm.
3., according to the method for p-phthaloyl chloride between a kind of Light chlorimation synthesis according to claim 2, it is characterized in that described light source is any one in fluorescent lamp, mercury lamp, ultraviolet lamp.
4., according to the method for p-phthaloyl chloride between a kind of Light chlorimation synthesis described in claim 1 or 2, it is characterized in that the mass ratio that feeds intake of dimethylbenzene described in step 1) and chlorine is: 1:(4-4.8).
5., according to the method for p-phthaloyl chloride between a kind of Light chlorimation synthesis according to claim 1, it is characterized in that step 2) described in Lewis acid be any one in iron trichloride, zinc chloride.
6., according to the method for p-phthaloyl chloride between a kind of Light chlorimation synthesis described in claim 1 or 5, it is characterized in that step 2) described in chlordene dimethylbenzene crude product ,/terephthalic acid, Lewis acid three the mass ratio that feeds intake be: 1:(0.5-0.55): (0.005-0.01).
7., according to the method for p-phthaloyl chloride between a kind of Light chlorimation synthesis according to claim 1, it is characterized in that vacuum degree control in step 1) in chlorination tower is at 730mmHg-750mmHg; Step 2) in vacuum degree control in reactor at 730mmHg-750mmHg.
8. according to the method for p-phthaloyl chloride between a kind of Light chlorimation synthesis according to claim 1, it is characterized in that the concrete steps of the synthesis of chlordene dimethylbenzene in step 1) are: put into by dimethylbenzene in chlorination tower, open chlorination tower heating unit, material in chlorination tower is made to rise to 80-90 DEG C, open chlorination tower inner light source, and open chlorine pipeline valve, chlorine to be contacted with material by chlorine gas distributor through under meter and side-chain chlorination occurs bottom chlorination tower, by controlling chlorination tower interchanger, temperature of reaction is made to maintain 85 DEG C-130 DEG C, by complete for the methyl of dimethylbenzene side chain chlorination, obtain chlordene dimethylbenzene crude product.
9. according to the method for p-phthaloyl chloride between a kind of Light chlorimation synthesis according to claim 1, it is characterized in that will obtain chlordene dimethylbenzene crude product in step 1) is transferred in degassed still, control vacuum tightness at 40-60mmHg, to remove hydrogenchloride in chlordene dimethylbenzene crude product and chlorine.
10. according to the method for p-phthaloyl chloride between a kind of Light chlorimation synthesis according to claim 1, it is characterized in that the specific operation process of rectification under vacuum in step 3) is: between inciting somebody to action/p-phthaloyl chloride crude product is delivered in rectifying tower, when liquid level in rectifying tower arrives 65-75%, stop charging, control vacuum tightness and carry out tower top total reflux operation between 0.01-10mmHg, when tower top temperature rises to 105 DEG C, column bottom temperature is kept to be 130 DEG C-140 DEG C, collect overhead fraction, each hr collections overhead fraction detects, when between detecting/paraphenylene terephthalamide's cl content be greater than 99.90% time, carry out the collection of finished product, between collection/p-phthaloyl chloride finished product time, improve tower top temperature to 110-115 DEG C, maintenance column bottom temperature is 130-140 DEG C, in the middle of overhead fraction/paraphenylene terephthalamide's cl content is when being less than 99.90%, stop the collection of m-phthaloyl chloride and stop heating.
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| CN201410517280.3A CN104230704A (en) | 2014-09-30 | 2014-09-30 | Method for synthesizing isophthalyl/terehthaloyl chloride through photochlorination |
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| CN201410517280.3A CN104230704A (en) | 2014-09-30 | 2014-09-30 | Method for synthesizing isophthalyl/terehthaloyl chloride through photochlorination |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105424860A (en) * | 2015-12-14 | 2016-03-23 | 山东凯盛新材料有限公司 | Liquid chromatographic analysis method of alpha, alpha, alpha, alpha', alpha', alpha'-hexachloro-m-xylene |
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| JPS508073B1 (en) * | 1970-12-22 | 1975-04-01 | ||
| JPS51127032A (en) * | 1975-04-25 | 1976-11-05 | Mitsubishi Gas Chem Co Inc | Process for preparation of aromatic dicarboxylic acid dichlorides |
| US4029560A (en) * | 1975-04-01 | 1977-06-14 | Mitsubishi Gas Chemical Company, Inc. | Process for producing α,α,α,α',α',α'-hexachloroxylene |
| US4165337A (en) * | 1976-10-25 | 1979-08-21 | Mitsubishi Gas Chemical Company, Inc. | Process for producing phthaloyl dichlorides of high purity |
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2014
- 2014-09-30 CN CN201410517280.3A patent/CN104230704A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS508073B1 (en) * | 1970-12-22 | 1975-04-01 | ||
| US4029560A (en) * | 1975-04-01 | 1977-06-14 | Mitsubishi Gas Chemical Company, Inc. | Process for producing α,α,α,α',α',α'-hexachloroxylene |
| JPS51127032A (en) * | 1975-04-25 | 1976-11-05 | Mitsubishi Gas Chem Co Inc | Process for preparation of aromatic dicarboxylic acid dichlorides |
| US4165337A (en) * | 1976-10-25 | 1979-08-21 | Mitsubishi Gas Chemical Company, Inc. | Process for producing phthaloyl dichlorides of high purity |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105424860A (en) * | 2015-12-14 | 2016-03-23 | 山东凯盛新材料有限公司 | Liquid chromatographic analysis method of alpha, alpha, alpha, alpha', alpha', alpha'-hexachloro-m-xylene |
| CN105424860B (en) * | 2015-12-14 | 2017-06-20 | 山东凯盛新材料股份有限公司 | The liquid phase chromatography analytical method of α, α, α, α ', α ', α ' chlordene meta-xylene |
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Application publication date: 20141224 |