CN113956223A - Preparation method of monochlorophthalic anhydride - Google Patents

Preparation method of monochlorophthalic anhydride Download PDF

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CN113956223A
CN113956223A CN202111294991.5A CN202111294991A CN113956223A CN 113956223 A CN113956223 A CN 113956223A CN 202111294991 A CN202111294991 A CN 202111294991A CN 113956223 A CN113956223 A CN 113956223A
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naphthalene
reaction
preparation
mixing
anhydride
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CN113956223B (en
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于有海
陈海权
陈春海
钱广涛
姚佳楠
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Donghua University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
    • C07D307/89—Benzo [c] furans; Hydrogenated benzo [c] furans with two oxygen atoms directly attached in positions 1 and 3
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/002—Mixed oxides other than spinels, e.g. perovskite
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
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    • B01J23/22—Vanadium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/74—Iron group metals
    • B01J23/745—Iron
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    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
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    • B01J27/128—Halogens; Compounds thereof with iron group metals or platinum group metals
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    • 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

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Abstract

The invention belongs to the technical field of fine chemical engineering, and particularly relates to a preparation method of monochlorophthalic anhydride. The invention provides a preparation method of monochlorophthalic anhydride, which comprises the following steps: naphthalene, chlorine and an iron catalyst are subjected to first mixing and then subjected to substitution reaction to obtain monochloro naphthalene; and carrying out second mixing on the monochloro naphthalene, an oxidant and a composite oxide catalyst, and carrying out oxidation reaction to obtain the monochlorophthalic anhydride. The monochlorophthalic anhydride prepared by the preparation method provided by the invention has high purity, and the preparation method is simple and convenient and has no explosion hazard.

Description

Preparation method of monochlorophthalic anhydride
Technical Field
The invention belongs to the technical field of fine chemical engineering, and particularly relates to a preparation method of monochlorophthalic anhydride.
Background
Monochlorophthalic anhydride is an important chemical raw material or intermediate, and is widely applied to the fields of medicines, pesticides, dyes and macromolecules. Polyimide is a special plastic with excellent high temperature resistance, chemical corrosion resistance and mechanical property, and monochlorophthalic anhydride is considered as an ideal raw material for synthesizing polyimide.
The traditional preparation method of monochlorophthalic anhydride comprises the steps of directly chlorinating phthalic anhydride at high temperature, wherein the yield is about 60 percent; or the phthalic anhydride is directly chloridized under the action of a catalyst, and the yield is about 70 percent. However, the purification of the monochlorophthalic anhydride obtained by the above-mentioned preparation method is difficult, and it is difficult to obtain high-purity monochlorophthalic anhydride. Chinese patent publication No. CN104496951A proposes a method for preparing chlorophthalic anhydride, which comprises using nitrophthalic acid as raw material, catalytic reducing to aminophthalic acid, diazotizing to obtain diazonium salt, performing chlorination with chlorinating agent to obtain crude chlorophthalic acid, vacuum dehydrating, rectifying and purifying to obtain high-purity chlorophthalic anhydride. However, the method of the invention is complicated, and diazotization reaction exists in the process, so that explosion is easy to occur.
Disclosure of Invention
The invention aims to provide a preparation method of monochlorophthalic anhydride, which has the advantages of high purity, simple preparation method and no explosion danger.
In order to achieve the above purpose, the invention provides the following technical scheme:
the invention provides a preparation method of monochlorophthalic anhydride, which comprises the following steps:
naphthalene, chlorine and an iron catalyst are subjected to first mixing and then subjected to substitution reaction to obtain monochloro naphthalene;
and carrying out second mixing on the monochloro naphthalene, an oxidant and a composite oxide catalyst, and carrying out oxidation reaction to obtain the monochlorophthalic anhydride.
Preferably, the iron-based catalyst comprises Fe and/or FeCl3。
Preferably, the mass ratio of the iron-based catalyst to naphthalene is 0.005-0.01: 1.
preferably, the mol ratio of the chlorine gas to the naphthalene is 0.45-0.48: 1.
preferably, the temperature of the substitution reaction is 100-120 ℃, and the time is 2-4 min.
Preferably, the composite oxide catalyst is V2O5And SiO2A mixture of (a); the V is2O5The mass of (a) is 5-18% of the mass of the mixture.
Preferably, the mass ratio of the composite oxide catalyst to the monochloro naphthalene is 0.01-0.015: 1.
preferably, the monochloronaphthalene is subjected to a second mixing in the form of a gas;
the oxidant comprises a gas comprising oxygen.
Preferably, the flow ratio of the monochloronaphthalene to the oxidizing agent is 1: 22.5 to 25.
Preferably, the temperature of the oxidation reaction is 400-460 ℃, and the time is 1-3 min.
The invention provides a preparation method of monochlorophthalic anhydride, which comprises the following steps: naphthalene, chlorine and an iron catalyst are subjected to first mixing and then subjected to substitution reaction to obtain monochloro naphthalene; and carrying out second mixing on the monochloro naphthalene, an oxidant and a composite oxide catalyst, and carrying out oxidation reaction to obtain the monochlorophthalic anhydride. The monochlorophthalic anhydride prepared by the preparation method provided by the invention has high purity, and the preparation method is simple and convenient and has no explosion hazard.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of monochloro naphthalene obtained in example 1;
FIG. 2 is a nuclear magnetic hydrogen spectrum of monochlorophthalic anhydride obtained in example 1.
Detailed Description
The invention provides a preparation method of monochlorophthalic anhydride, which comprises the following steps:
naphthalene, chlorine and an iron catalyst are subjected to first mixing and then subjected to substitution reaction to obtain monochloro naphthalene;
and carrying out second mixing on the monochloro naphthalene, an oxidant and a composite oxide catalyst, and carrying out oxidation reaction to obtain the monochlorophthalic anhydride.
In the present invention, all the starting materials for the preparation are commercially available products known to those skilled in the art unless otherwise specified.
In the present invention, the synthesis route of the monochlorophthalic anhydride is preferably:
Figure BDA0003336235890000021
the monochloro naphthalene is obtained by carrying out substitution reaction after naphthalene, chlorine and an iron catalyst are subjected to first mixing.
In the present invention, the iron-based catalyst preferably includes Fe and/or FeCl3(ii) a When the iron-based catalyst is Fe and FeCl3In the present invention, the ratio of the two components is not particularly limited, and the components may be mixed in any ratio.
In the present invention, the mass ratio of the iron-based catalyst to naphthalene is preferably 0.005 to 0.01: 1, more preferably 0.006 to 0.009: 1, more preferably 0.007 to 0.008: 1. in the invention, the mol ratio of chlorine to naphthalene is preferably 0.45-0.48: 1, more preferably 0.46 to 0.47: 1.
in the present invention, the process of the first mixing preferably includes the steps of: premixing naphthalene and an iron catalyst, and heating and melting to obtain a premix; and introducing chlorine into the premix to perform substitution reaction.
In the present invention, the process of premixing is preferably stirring. In the invention, the rotation speed of the stirring is preferably 150-170 rpm, more preferably 155-165 rpm, and more preferably 158-160 rpm; the time is preferably 2 to 5min, and more preferably 3 to 4 min. In the invention, the heating and melting temperature is preferably 100-120 ℃, more preferably 105-115 ℃, and even more preferably 110-112 ℃. The invention has no special requirements on the process of introducing the chlorine gas, and the rated amount of the chlorine gas can be introduced into the premix.
In the invention, the temperature of the substitution reaction is preferably 100-120 ℃, more preferably 105-115 ℃, and more preferably 110-112 ℃; the time is preferably 2 to 4min, and more preferably 3 min. In the present invention, the substitution reaction is preferably carried out in a reaction vessel.
In the process of carrying out the substitution reaction, the invention also preferably comprises treating the tail gas generated by the reaction; the process for treating the tail gas preferably comprises the following steps: and introducing the tail gas into water to generate hydrochloric acid. The process of introducing the tail gas is not particularly limited in the present invention, and those skilled in the art can use the same.
After the substitution reaction is finished, the method also preferably comprises the step of carrying out post-treatment on the material obtained by the reaction, wherein the post-treatment preferably comprises the steps of nitrogen purging, distillation and purification, neutralization and filtration which are sequentially carried out.
In the present invention, the nitrogen purging is preferably performed by introducing nitrogen into the reaction product. In the present invention, the reaction product can be purged to neutrality by purging with nitrogen.
In the invention, the temperature of the distillation purification is preferably 259-260 ℃. The distillation purification process is not particularly limited in the present invention, and those well known to those skilled in the art can be used.
After the distillation purification is completed, the present invention preferably neutralizes and filters the obtained fraction. In the present invention, the agent used for the neutralization is preferably anhydrous sodium carbonate. In the present invention, the amount ratio of the distillate to anhydrous sodium carbonate is preferably 95 to 100mL/g, and more preferably 96 to 99 mL/g. The filtration process is not particularly limited in the present invention, and those skilled in the art will be familiar with the filtration process.
In the invention, the yield of the monochloronaphthalene is preferably 85-92%, more preferably 86-91%, and even more preferably 87-90%.
After the monochloronaphthalene is obtained, the monochloronaphthalene, the oxidant and the composite oxide catalyst are subjected to second mixing and oxidation reaction to obtain the monochlorophthalic anhydride.
In the present invention, the oxidizing agent preferably includes a gas containing oxygen, more preferably air, and still more preferably purified air. In the invention, the volume content of oxygen in the oxidant is preferably 20-30%, more preferably 22-28%, and even more preferably 24-26%.
In the present invention, the complex oxide catalyst is preferably V2O5And SiO2A mixture of (a). In the present invention, said V2O5The amount of (b) is preferably 5 to 18% by mass, more preferably 6 to 17% by mass, and still more preferably 7 to 16% by mass of the mixture.
In the present invention, the monochloronaphthalene is preferably subjected to the second mixing in the form of a gas. In the present invention, the gas flow rates of the monochloronaphthalene and the oxidizing agent are preferably 1: 22.5 to 25, preferably 23 to 24.5, and more preferably 23.5 to 24. In the invention, the mass ratio of the composite oxide catalyst to the monochloro naphthalene is preferably 0.01-0.015: 1, more preferably 0.011 to 0.014: 1, more preferably 0.012 to 0.013: 1.
the present invention also preferably includes preheating and vaporizing the monochloronaphthalene in sequence prior to the second mixing. In the invention, the preheating temperature is preferably 230-250 ℃, more preferably 235-245 ℃, and more preferably 240 ℃. In the invention, the vaporization temperature is preferably 240-280 ℃, more preferably 250-270 ℃, and even more preferably 255-265 ℃. In the invention, the monochlorophthalene is preheated, so that the production efficiency and the yield of monochlorophthalic anhydride can be further improved.
The present invention also preferably includes preheating the oxidizing agent prior to second mixing the oxidizing agent. In the invention, the preheating temperature is preferably 140-160 ℃, more preferably 142-158 ℃, and more preferably 145-150 ℃. In the present invention, the reaction rate and the catalytic efficiency can be further improved by preheating the oxidizing agent.
In the present invention, the second mixing process is preferably: premixing the monochloronaphthalene and an oxidant, and then mixing the monochloronaphthalene and the oxidant again.
The process of the premixing is not particularly limited in the present invention, and may be performed as is well known to those skilled in the art. In the present invention, the premixing is preferably carried out in a vaporizer.
In the present invention, the remixing process is preferably: and introducing mixed gas obtained by premixing the monochloronaphthalene and the oxidant into a reactor containing a composite oxide catalyst for remixing. The manner of introducing the gas is not particularly limited in the present invention, and those known to those skilled in the art can be used. In the present invention, the reactor is preferably a gas-phase tubular fixed bed reactor.
In the invention, the temperature of the oxidation reaction is preferably 400-460 ℃, more preferably 410-450 ℃, and more preferably 420-440 ℃; the time is preferably 1 to 3min, and more preferably 2 min.
In the process of the oxidation reaction, the invention also preferably comprises the step of burning the tail gas generated by the oxidation reaction. The invention has no special requirements on the incineration treatment process, and the method can be realized by adopting the method which is well known by the technical personnel in the field.
After the oxidation reaction is finished, the invention also preferably comprises rectifying the material obtained by the reaction. In the invention, the temperature of the rectification treatment is preferably 313-315 ℃. The rectification process is not particularly limited in the present invention, and those well known to those skilled in the art can be used.
In the invention, the purity of the monochlorophthalic anhydride is preferably 95-98%; more preferably 96 to 97%. In the invention, the yield of the monochlorophthalic anhydride is preferably 70-80%, more preferably 72-78%, and even more preferably 74-76%.
In order to further illustrate the present invention, the following detailed description of the preparation method of monochlorophthalic anhydride is provided in connection with the accompanying drawings and examples, which should not be construed as limiting the scope of the present invention.
Example 1
25kg of naphthalene and 225g of catalyst FeCl3The resulting mixture was placed in a reaction vessel equipped with a stirrer, heated to 110 ℃ at a stirring speed of 150rpm, and subjected to melting treatment, at which chlorine gas (the nominal molar amount of chlorine gas was 91.7mol) was introduced into the molten reaction material to cause substitution reaction for 2 min. And in the reaction process, introducing the generated tail gas into water to prepare hydrochloric acid. After the substitution reaction is finished, purging the reaction product to be neutral by using nitrogen, then carrying out distillation and purification, and collecting a fraction at 259-260 ℃; neutralizing the distillate with 0.1kg of anhydrous sodium carbonate, and filtering to obtain monochloro naphthalene; the yield of the monochloronaphthalene is 90%;
introducing purified air preheated to 150 ℃ into a monochloronaphthalene vaporizer, simultaneously feeding 28.5kg of monochloronaphthalene preheated to 250 ℃ into the vaporizer, setting the vaporization temperature to 270 ℃, fully and uniformly mixing the purified air and the vaporized monochloronaphthalene (the flow of the purified air is 23.0 times of that of the vaporized monochloronaphthalene), and uniformly introducing a catalyst V2O5-SiO2(34.2gV2O5And 307.8g SiO2) The gas-phase tubular fixed bed reactor carries out oxidation reaction, and the reaction temperature of the fixed bed is set to be 450 ℃. In the reaction process, the reaction tail gas is incinerated. After the oxidation reaction is finished, rectifying and purifying the obtained crude product, and collecting fractions at 313-315 ℃ to obtain monochlorophthalic anhydride with the purity of 97% and the yield of 75%.
Example 2
25kg of naphthalene and 225g of catalyst Fe were placed in a reaction vessel equipped with a stirrer, and the temperature was raised to 110 ℃ at a stirring speed of 150rpm to carry out a melting treatment, and at the above temperature, chlorine gas (the nominal molar amount of chlorine gas was 91.7mol) was introduced into the molten reaction material to carry out a substitution reaction for 2 min. And in the reaction process, introducing the generated tail gas into water to prepare hydrochloric acid. After the substitution reaction is finished, purging the reaction product to be neutral by using nitrogen, then carrying out distillation and purification, and collecting a fraction at 259-260 ℃; neutralizing the distillate with 0.1kg of anhydrous sodium carbonate, and filtering to obtain monochloro naphthalene; the yield of the monochloronaphthalene is 90%;
introducing purified air preheated to 150 DEG CIntroducing into a monochloro naphthalene vaporizer, simultaneously introducing 26.0kg of monochloro naphthalene preheated to 250 deg.C into the vaporizer, setting vaporization temperature at 270 deg.C, mixing purified air and vaporized monochloro naphthalene uniformly (flow of purified air is 23.0 times of flow of vaporized monochloro naphthalene), and introducing catalyst V2O5-SiO2(34.2gV2O5And 307.8g SiO2) The gas-phase tubular fixed bed reactor carries out oxidation reaction, and the reaction temperature of the fixed bed is set to be 450 ℃. In the reaction process, the reaction tail gas is incinerated. After the oxidation reaction is finished, rectifying and purifying the obtained crude product, and collecting fractions at 313-315 ℃ to obtain monochlorophthalic anhydride with the purity of 96% and the yield of 75%.
Example 3
25kg of naphthalene and 225g of catalyst FeCl3 were placed in a reaction vessel equipped with a stirrer, and the temperature was raised to 110 ℃ at a stirring speed of 150rpm to carry out melt processing, and at the above temperature, chlorine gas (the nominal molar amount of chlorine gas was 91.7mol) was introduced into the molten reaction material to carry out substitution reaction for 2 min. And in the reaction process, introducing the generated tail gas into water to prepare hydrochloric acid. After the substitution reaction is finished, purging the reaction product to be neutral by using nitrogen, then carrying out distillation and purification, and collecting a fraction at 259-260 ℃; neutralizing the distillate with 1kg of anhydrous sodium carbonate, and filtering to obtain monochloro naphthalene; the yield of the monochloronaphthalene is 90%;
introducing purified air preheated to 150 ℃ into a monochloronaphthalene vaporizer, simultaneously feeding 28.5kg of monochloronaphthalene preheated to 250 ℃ into the vaporizer, setting the vaporization temperature to 270 ℃, fully and uniformly mixing the purified air and the vaporized monochloronaphthalene (the flow of the purified air is 23.0 times of that of the vaporized monochloronaphthalene), and uniformly introducing a catalyst V2O5-SiO2(51.3gV2O5And 290.7g SiO2) The gas-phase tubular fixed bed reactor carries out oxidation reaction, and the reaction temperature of the fixed bed is set to be 450 ℃. In the reaction process, the reaction tail gas is incinerated. After the oxidation reaction is finished, rectifying and purifying the obtained crude product, and collecting fractions at 313-315 ℃ to obtain monochlorophthalic anhydride with the purity of 96 percent and the yieldThe content was 79%.
Performance testing
Nuclear magnetic hydrogen spectrum test is carried out on the monochloro naphthalene and monochloro phthalic anhydride obtained in example 1, the test result of the monochloro naphthalene is shown in figure 1, and the spectrum information is as follows:
1H NMR(400MHz,CDCl3,ppm)δ＝8.22(d,1H,J＝8.0Hz),7.73(m,1H),7.63(d,1H,J＝8.0Hz),7.48(m,2H),7.42(m,1H),7.25(m,1H).ESIMS m/z 163.62[M+H]+；
the test results of the monochlorophthalic anhydride are shown in FIG. 2, and the map information is:
1H NMR(400MHz,CDCl3,ppm)δ＝8.00(dd,1H,J＝0.8,0.4Hz),7.97(dd,1H,J＝0.4,0.8Hz),7.88(dd,1H,J＝1.6,1.6Hz).ESIMS m/z183.56[M+H]+。
although the above embodiments have been described in detail, they are only a part of the embodiments of the present invention, not all of the embodiments, and other embodiments can be obtained without inventive step according to the embodiments, and all of the embodiments belong to the protection scope of the present invention.

Claims (10)

1. The preparation method of monochlorophthalic anhydride is characterized by comprising the following steps:
naphthalene, chlorine and an iron catalyst are subjected to first mixing and then subjected to substitution reaction to obtain monochloro naphthalene;
and carrying out second mixing on the monochloro naphthalene, an oxidant and a composite oxide catalyst, and carrying out oxidation reaction to obtain the monochlorophthalic anhydride.
2. The method of claim 1, wherein the iron-based catalyst comprises Fe and/or FeCl3。
3. The method according to claim 2, wherein the mass ratio of the iron-based catalyst to naphthalene is 0.005 to 0.01: 1.
4. the preparation method according to claim 1, wherein the molar ratio of chlorine to naphthalene is 0.45-0.48: 1.
5. the method according to any one of claims 1 to 4, wherein the temperature of the substitution reaction is 100 to 120 ℃ and the time is 2 to 4 min.
6. The production method according to claim 1, wherein the complex oxide catalyst is V2O5And SiO2A mixture of (a); the V is2O5The mass of (a) is 5-18% of the mass of the mixture.
7. The production method according to claim 6, wherein the mass ratio of the composite oxide catalyst to the monochloronaphthalene is 0.01 to 0.015: 1.
8. the method of claim 1, wherein the monochloronaphthalene is subjected to a second mixing in the form of a gas;
the oxidant comprises a gas comprising oxygen.
9. The process according to claim 8, characterized in that the flow ratio between monochloronaphthalene and oxidizing agent is 1: 22.5 to 25.
10. The method according to claim 1, wherein the temperature of the oxidation reaction is 400 to 460 ℃ and the time is 1 to 3 min.
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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB941293A (en) * 1961-04-28 1963-11-06 Basf Ag Production of phthalic anhydride by catalytic oxidation and a catalyst therefor
GB1074316A (en) * 1964-11-06 1967-07-05 Halcon International Inc Production or phthalic anhydride
GB1083999A (en) * 1961-09-11 1967-09-20 Halcon International Inc Production of phthalic anhydride and catalysts suitable for use therein
CN1274527A (en) * 1999-05-19 2000-11-29 烟台福联生物化学有限公司 Technological process for producing wax-dissolving penetrant
CN1319333A (en) * 2001-01-17 2001-10-31 王家波 Wax dissolving agent, its preparation method and application in pesticide

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB941293A (en) * 1961-04-28 1963-11-06 Basf Ag Production of phthalic anhydride by catalytic oxidation and a catalyst therefor
GB1083999A (en) * 1961-09-11 1967-09-20 Halcon International Inc Production of phthalic anhydride and catalysts suitable for use therein
GB1074316A (en) * 1964-11-06 1967-07-05 Halcon International Inc Production or phthalic anhydride
CN1274527A (en) * 1999-05-19 2000-11-29 烟台福联生物化学有限公司 Technological process for producing wax-dissolving penetrant
CN1319333A (en) * 2001-01-17 2001-10-31 王家波 Wax dissolving agent, its preparation method and application in pesticide

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
曹龙海: "苯酐氯化制单氯代苯酐", 《化学工程师》 *
胡乘方 等: "《有机化学》", 28 February 1988, 农业出版社 *

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