CN112500279A - Preparation of C by micro-channel technology21Method for preparing dibasic acid - Google Patents

Preparation of C by micro-channel technology21Method for preparing dibasic acid Download PDF

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Publication number
CN112500279A
CN112500279A CN202011503193.4A CN202011503193A CN112500279A CN 112500279 A CN112500279 A CN 112500279A CN 202011503193 A CN202011503193 A CN 202011503193A CN 112500279 A CN112500279 A CN 112500279A
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preparing
dibasic acid
acid
reaction
pressure
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林良良
夏远
路雯桐
温虹钰
郭继香
李子洋
许虎君
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Jiangnan University
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Jiangnan University
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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
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
    • 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
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/0093—Microreactors, e.g. miniaturised or microfabricated reactors
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates to a method for preparing C by utilizing a microchannel technology21A method of dibasic acid, belonging to the technical field of surfactant preparation. Firstly, placing oleic acid and catalyst iodine into a high-pressure reaction kettle, introducing nitrogen to replace air in the reaction kettle, magnetically stirring, heating to a specified temperature, and reacting for a period of time; then putting the pipeline reactor into a heating device to be heated to a specified temperature; then mixing the obtained high-pressure reaction kettle liquid with acrylic acid according to a certain molar ratio, adding polymerization inhibitor hydroquinone, introducing the mixed liquid into a pipeline reactor by using a constant-flow pump for reaction, and setting the flow rate on the constant-flow pump; finally, the crude product is subjected to reduced pressure distillation to obtain relatively pure C21A dibasic acid. Compared with the prior art, the method has the advantages of low reaction temperature and pressure, short time, low energy consumption and safetyThe hidden danger is small, the production efficiency and the economic benefit are high, and an important reference is provided for the continuous preparation of the surfactant.

Description

Preparation of C by micro-channel technology21Method for preparing dibasic acid
Technical Field
The invention relates to a method for preparing C by utilizing a microchannel technology21A method of dibasic acid belongs to the technical field of surfactant preparation.
Background
C21C obtained by neutralizing dibasic acid with KOH21The dibasic acid potassium salt anionic surfactant has carboxyl as hydrophilic group and long chain hydrocarbon as hydrophobic group, and is adsorbed onto the interface between two phases directionally in solution to lower the surface tension of the solution. Due to C21The two carboxyl groups in the dibasic acid can generate a monobasic or dibasic fatty acid derivative, and the double bond can generate addition, oxidation and halogenation, so the dibasic acid can also be applied to preparing ink, a lubricant, an adhesive, an epoxy resin curing agent, paint and the like. At present, C is not realized at home21The independent production of the dibasic acid completely depends on foreign import, severe production conditions and high production cost is C in China21The main problem facing the diacid synthesis industry.
A number of syntheses C have now been developed21The method of dibasic acid is mainly divided into a high-pressure reaction kettle chemical synthesis method and a microbial fermentation production method according to the preparation process. The high-pressure reaction kettle method requires high-pressure and high-power reaction conditions, and has the disadvantages of high energy consumption, high preparation process cost, and complicated and unsafe operation steps. The microbiological method utilizes the specific substrate conversion ability of organisms and controls C by adding different substrates21The carbon chain length of the dibasic acid, the problems of large electric energy consumption, high equipment investment, high production cost and the like exist in the general fermentation production process. Meanwhile, the methods cannot continuously prepare C21A dibasic acid. Therefore, the method has low energy consumption and simple operation and can continuously prepare the C21Dibasic acidThe method has important fundamental research significance and application value.
The invention provides a method for realizing C by taking oleic acid and acrylic acid as raw materials and combining a pipeline reactor21The binary acid is continuously prepared. Compared with the traditional synthetic method, the method has the advantages of low energy consumption, simple and safe operation, short time consumption, high production efficiency and conversion rate, and capability of realizing continuous production, namely C21The high-efficiency and continuous industrial production of the dibasic acid opens up a new path.
Patent CN103113228A provides a method for preparing C by using high-pressure reaction kettle21-38Saturated alicyclic dibasic acids or esters. The method has the advantages that the reaction temperature is 160-180 ℃, the reaction time is 6-8 hours, the reaction pressure is 1.5-2 MPa, and the problems of high reaction energy consumption, long time, low efficiency and the like at high temperature and high pressure exist. The invention utilizes a pipeline reactor to prepare C21The dibasic acid reacts for 3 hours at 170 ℃ and 100psi to obtain the compound C21The dibasic acid with a conversion rate of more than 89 percent not only greatly shortens the reaction time, reduces the reaction pressure and temperature, improves the reaction safety, but also improves the conversion rate and economic benefits.
Patent CN1928100A provides a method for synthesizing long chain alpha, omega-dicarboxylic acids by using microorganisms. In the method, the thalli can generate respiratory metabolism, so that the temperature is increased, and a large amount of cooling water is needed for cooling the fermentation system, so that the energy consumption is high, the personnel input is increased, and the production cost is increased. The invention utilizes a pipeline reactor to prepare C21The dibasic acid has the advantages of simple operation, less personnel input, continuous industrial production, high reaction efficiency and the like.
Disclosure of Invention
The invention aims to provide a method for preparing C by utilizing a microchannel technology21Method of using dibasic acid against existing C21The defects in the binary acid preparation process are combined with the advantages of a pipeline reactor in process strengthening, the oleic acid and the acrylic acid are used as raw materials, and the pipeline reactor is utilized to realize efficient, energy-saving and continuous controllable preparation of C21A method of using dibasic acid. The method has the advantages of simple preparation process, low energy consumption, short time consumption, continuous production, high reaction efficiency, and more production processSafety and the like.
The technical scheme of the invention is as follows:
preparation of C by micro-channel technology21The method of the dibasic acid comprises the following steps:
(1) placing oleic acid and catalyst iodine into a high-pressure reaction kettle, introducing inert gas to replace air in the reaction kettle, stirring, heating to a specified temperature, and reacting for a period of time;
(2) putting the pipeline reactor into a heating device to be heated to a specified temperature;
(3) mixing the high-pressure reaction kettle liquid obtained in the step (1) with acrylic acid according to a certain molar ratio, adding polymerization inhibitor hydroquinone, and pumping the mixed liquid into a pipeline reactor by using a pump for reaction to obtain a crude product.
(4) The crude product is distilled under reduced pressure to obtain pure C21A dibasic acid.
Performing Gas Chromatography (GC) quantitative analysis on a raw material oleic acid, and calculating the content of linoleic acid in the oleic acid by adopting an area normalization method, wherein the dosage of iodine in the catalyst in the step (1) is 0.1-0.4% of the mass of linoleic acid, the molar ratio of acrylic acid to linoleic acid in the step (2) is 1-1.5: 1, and the mass of hydroquinone is 0.8-1.2% of the mass of acrylic acid.
In the step (1), the reaction temperature in the high-pressure reaction kettle is 140-160 ℃, and the reaction time is 1-2 hours.
In the step (1), the reaction pressure in the high-pressure reaction kettle is normal pressure to 10 MPa.
In the step (2), the heating device is an oil bath kettle, and the reaction temperature is 160-205 ℃.
In the step (3), the residence time of the reactants in the pipeline reactor is 1-4 h, and the flow rate is calculated by dividing the time by the volume of the pipeline reactor.
The pressure of the reactants in the pipeline reactor is 0-100 psi.
The pipeline reactor is a stainless steel pipe, a copper pipe or a nickel pipe or other metal pipes, the inner diameter is 1-10 mm, and the length is 3-10 m.
C generated within the scope of the invention21The conversion rate of the dibasic acid reaches 94 percent. Conversion can be increased by varying the reaction temperature, reaction pressure and residence time.
The principle of the invention is as follows: the micro-fluidic technology utilizes micro-channels (with the size of tens of microns to hundreds of microns) to process or manipulate micro-fluid (with the volume of nanoliters to attoliters) to realize chemical synthesis, and has the characteristics of miniaturization, integration and the like. The diffusion distance in the pipeline is very short, and the specific surface area of the microchannel reactor is higher by several orders of magnitude compared with that of a conventional reactor, so that the microchannel reactor has very high heat and mass transfer rates. Continuous flow is used for replacing intermittent operation and the large specific surface area, so that the technology has the characteristics of good controllability, narrow residence time distribution, high heat and mass transfer rate, small potential safety hazard, good product uniformity and the like.
And C21The synthesis mechanism of the dibasic acid is mainly Diels-Alder reaction, firstly oleic acid raw material used in experiment is mixed with iodine to make linoleic acid conjugated, then the obtained conjugated diene and acrylic acid undergo the process of cycloaddition reaction to obtain six-membered ring C21The synthesis principle of the dibasic acid is shown in figure 1.
The invention has the following beneficial results:
(1) high production efficiency, simple operation process and short reaction time. Because the heat and mass transfer rate of the pipeline reactor is high, the method can obtain C with high conversion rate at lower temperature and pressure21A dibasic acid;
(2) safe and continuous production, low cost and high economic benefit;
(3) the reaction process is flexible and controllable, the product is uniform, and the surfactant obtained after neutralization with potassium salt has excellent performance.
Drawings
FIG. 1 shows the present invention C21A synthetic schematic diagram of dibasic acid.
FIG. 2 is a schematic view of the apparatus of the present invention.
FIG. 3 is a gas chromatogram of oleic acid, a starting material used in examples 1 to 7 of the present invention.
FIG. 4 shows the product C obtained in example 1 of the present invention21Gas chromatogram of dibasic acid.
FIG. 5 shows the product C obtained in example 2 of the present invention21Gas chromatogram of dibasic acid.
FIG. 6 shows that the product C obtained in example 3 of the present invention21Gas chromatogram of dibasic acid.
FIG. 7 shows that the product C obtained in example 4 of the present invention21Gas chromatogram of dibasic acid.
FIG. 8 shows the product C obtained in example 5 of the present invention21Gas chromatogram of dibasic acid.
FIG. 9 shows the product C obtained in example 6 of the present invention21Gas chromatogram of dibasic acid.
FIG. 10 shows the product C obtained in example 7 of the present invention21Dibasic acid infrared spectrogram.
In the figure: 1, a suction filter head; 2, reacting a reactant; 3, a constant-flow pump; 4, a pipeline reactor; 5, oil bath pan; 6 conical flask.
Detailed Description
The present invention will be described in further detail with reference to the following examples, but the present invention is not limited to the following examples. The present invention includes various alterations and modifications made by those skilled in the art based on the above technical ideas and conventional means, and is intended to be included in the scope of the present invention.
The reaction apparatus used in the examples comprises three sections: a feed zone, a reaction zone and a collection zone. The feeding area consists of reactants 2 and a constant flow pump 3, the reaction area comprises a pipeline reactor 4 and an oil bath pot 5, and the collecting area is a conical flask 6. The reaction container is provided with a suction filter head 1. Wherein, the pipeline reactor is a stainless steel pipe, the inner diameter is 2mm, and the length is 4 m.
Example 1
(1) Taking a raw material oleic acid to perform methyl esterification reaction, carrying out quantitative analysis by GC, and calculating by adopting an area normalization method to obtain a mixture containing palmitic acid: oleic acid: linoleic acid 10.1943%: 56.9693%: 32.8364 percent.
(2) Putting 150g of oleic acid and 0.098g of catalyst iodine into a high-pressure reaction kettle, introducing nitrogen to replace air in the reaction kettle, magnetically stirring, heating to 150 ℃ and reacting for 2 hours to obtain an intermediate product.
(3) The reaction device is connected as required, and the pipeline reactor is placed in an oil bath pot and heated to 180 ℃.
(4) To the intermediate product obtained, acrylic acid (n (acrylic acid): n (linoleic acid): 1.2:1) was added, hydroquinone as a reactant, which was a polymerization inhibitor in an amount of 1% by mass of acrylic acid, was left under heating for 3 hours, and the reaction product was collected in a conical flask under a pressure of 100 psi.
(5) And carrying out methyl esterification reaction on the reaction product, carrying out quantitative analysis by using GC respectively, calculating the content of each component by using an area normalization method, and obtaining the reaction conversion rate of 93% by calculation.
The gas phase of the starting oleic acid is shown in FIG. 3, the gas phase of the reaction product is shown in FIG. 4, and the retention time of 16.931min represents the peak of linoleic acid.
Example 2
The treatment process, treatment time and pressure were the same as in example 1 except that: the oil bath pan reaction temperature was 170 degrees. And (3) carrying out methyl esterification on the reaction product, carrying out quantitative analysis by using GC, and calculating the content of each component by using an area normalization method, wherein the conversion rate is 89%. The chromatogram is shown in fig. 5, the retention time of 17.112min represents the peak of linoleic acid, and the peak area of linoleic acid is obviously increased compared with the gas phase diagram in fig. 3, which shows that the reaction temperature in the pipeline reactor is increased, the conversion rate is increased, because the effective collision frequency of reactant molecules is increased and the reaction rate is accelerated due to the increased temperature.
Example 3
The treatment process, treatment time and treatment temperature were the same as in example 1, except that: the reaction pressure in the pipeline reactor was 40 psi. Carrying out methyl esterification reaction on the reaction product, carrying out quantitative analysis by GC, calculating the content of each component by adopting an area normalization method, and obtaining the conversion rate of 68 percent by calculation. The chromatogram is shown in FIG. 6, the retention time of 17.145min represents the peak of linoleic acid, and the peak area of linoleic acid is obviously increased compared with the gas phase diagram of FIG. 4, which shows that the reaction pressure is increased and the conversion rate is improved.
Example 4
The treatment process, treatment temperature and treatment pressure were the same as in example 3, except that: the reaction time in the pipeline reactor was 4 h. Carrying out methyl esterification reaction on the reaction product, carrying out quantitative analysis by GC, calculating the content of each component by adopting an area normalization method, and obtaining the conversion rate of 81.2 percent by calculation. The chromatogram is shown in fig. 7, the retention time of 17.407min represents the peak of linoleic acid, and the peak area of linoleic acid is obviously reduced compared with the gas phase diagram of fig. 5, which shows that the retention time in the pipeline reactor is increased, the reaction is more complete, and the conversion rate is increased.
Example 5
The treatment process was the same as in example 1 except that the reaction temperature of the pipe reactor was 160 ℃ and the reaction time was 1 hour, and no external pressure was applied. Carrying out methyl esterification reaction on the reaction product, carrying out quantitative analysis by GC, calculating the content of each component by adopting an area normalization method, and obtaining the conversion rate of 48 percent by calculation. The pattern is shown in FIG. 8, and the retention time is 17.087min represents the peak of linoleic acid. Compared with the above examples, the area of linoleic acid peak is obviously increased, which shows that the conversion rate is low when the reaction temperature in the pipeline reactor is low, no external pressure is applied, and the reaction time is short.
Example 6
The treatment process was the same as in example 1, except that the reaction temperature in the pipe reactor was 205 deg.C, the reaction time was 4 hours, and no external pressure was applied. Carrying out methyl esterification reaction on the reaction product, carrying out quantitative analysis by GC, calculating the content of each component by adopting an area normalization method, and obtaining the conversion rate of 94% by calculation. The pattern is shown in FIG. 9, and the retention time is 17.549min represents the peak of linoleic acid. The area of linoleic acid peak was smaller compared to the above examples, indicating that even without applied pressure, the conversion increased if the reaction temperature of the pipeline reactor was high enough and the reaction time was long enough.
Example 7
C obtained in example 1 was purified by distillation under reduced pressure21The results of the infrared spectrum characterization of the dibasic acid are shown in FIG. 10.
According to the figure, 3500-2500 cm-1Is C21The stretching vibration peak of O-H in the dibasic acid is 1750-1700 cm-1Is a strong stretching vibration peak of C ═ O, 1500-1300 cm-1Is the bending vibration peak of methylene, which further proves that the target product C is synthesized21A dibasic acid.
The present invention is explained in detail in the above examples. It is to be understood that the invention is not limited to the specific forms described above, but that various changes may be made by those skilled in the art within the scope of the claims without departing from the spirit of the invention.

Claims (10)

1. Preparation of C by micro-channel technology21The method for preparing the dibasic acid is characterized by comprising the following steps of:
(1) placing oleic acid and catalyst iodine into a high-pressure reaction kettle, introducing inert gas to replace air in the reaction kettle, stirring, heating to a specified temperature, and reacting for a period of time;
(2) putting the pipeline reactor into a heating device to be heated to a specified temperature;
(3) mixing the high-pressure reaction kettle liquid obtained in the step (1) with acrylic acid according to a certain molar ratio, adding polymerization inhibitor hydroquinone, and pumping the mixed liquid into a pipeline reactor by using a pump to react to obtain a crude product;
(4) the crude product is distilled under reduced pressure to obtain pure C21A dibasic acid.
2. The method of claim 1, wherein the step of preparing C comprises using microchannel technology21The method for preparing the dibasic acid is characterized in that gas chromatography quantitative analysis is carried out on a raw material oleic acid, the content of linoleic acid in the oleic acid is calculated by adopting an area normalization method, and in the step (1), the using amount of the catalyst iodine is 0.1-0.4% of the mass of the linoleic acid.
3. The method of claim 1, wherein the step of preparing C comprises using microchannel technology21The method for preparing the dibasic acid is characterized in that in the step (1), the reaction temperature in the high-pressure reaction kettle is 140-160 ℃, and the reaction time is 1-2 hours.
4. The method of claim 1, wherein the step of preparing C comprises using microchannel technology21The method for preparing the dibasic acid is characterized in that in the step (1), the reaction pressure in the high-pressure reaction kettle is normal pressure to 10 MPa.
5. The method of claim 1, wherein the step of preparing C comprises using microchannel technology21The method for preparing the dibasic acid is characterized in that in the step (2), the heating device is an oil bath kettle, and the reaction temperature is 160-205 ℃.
6. The method of claim 1, wherein the step of preparing C comprises using microchannel technology21The method for preparing the dibasic acid is characterized in that in the step (2), the pressure of reactants in a pipeline reactor is 0-100 psi.
7. The method of claim 1, wherein the step of preparing C comprises using microchannel technology21The method for preparing the dibasic acid is characterized in that in the step (3), the molar ratio of the acrylic acid to the linoleic acid is 1-1.5: 1.
8. The method of claim 1, wherein the step of preparing C comprises using microchannel technology21The method for preparing the dibasic acid is characterized in that in the step (3), the mass of the hydroquinone is 0.8-1.2% of that of the acrylic acid.
9. The method of claim 1, wherein the step of preparing C comprises using microchannel technology21The method for preparing the dibasic acid is characterized in that in the step (3), the residence time of reactants in the pipeline reactor is 1-4 h, and the flow rate is calculated by dividing the time by the volume of the pipeline reactor.
10. The method of claim 1, wherein the step of preparing C comprises using microchannel technology21The method for preparing the dibasic acid is characterized in that the pipeline reactor is a stainless steel pipe, a copper pipe or a nickel pipe or other metal pipes, the inner diameter is 1-10 mm, and the length is 3-10 m.
CN202011503193.4A 2020-12-18 2020-12-18 Preparation of C by micro-channel technology21Method for preparing dibasic acid Pending CN112500279A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114349626A (en) * 2022-03-21 2022-04-15 佛山市滔盛弘新材料科技有限公司 Novel preparation method of C21 dibasic acid

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Publication number Priority date Publication date Assignee Title
CN105859544A (en) * 2016-04-21 2016-08-17 江南大学 High-purity oleic acid and preparation method thereof
CN111943833A (en) * 2020-09-08 2020-11-17 安庆市虹泰新材料有限责任公司 C21Preparation method of dibasic acid

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Publication number Priority date Publication date Assignee Title
CN105859544A (en) * 2016-04-21 2016-08-17 江南大学 High-purity oleic acid and preparation method thereof
CN111943833A (en) * 2020-09-08 2020-11-17 安庆市虹泰新材料有限责任公司 C21Preparation method of dibasic acid

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114349626A (en) * 2022-03-21 2022-04-15 佛山市滔盛弘新材料科技有限公司 Novel preparation method of C21 dibasic acid

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Application publication date: 20210316