CN114437562B - Modified oil dye, oil colorant, preparation method and application thereof and colored petroleum product - Google Patents

Modified oil dye, oil colorant, preparation method and application thereof and colored petroleum product Download PDF

Info

Publication number
CN114437562B
CN114437562B CN202011193828.5A CN202011193828A CN114437562B CN 114437562 B CN114437562 B CN 114437562B CN 202011193828 A CN202011193828 A CN 202011193828A CN 114437562 B CN114437562 B CN 114437562B
Authority
CN
China
Prior art keywords
oil
acid
dye
colorant
chain fatty
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN202011193828.5A
Other languages
Chinese (zh)
Other versions
CN114437562A (en
Inventor
黄燕民
刘倩
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sinopec Research Institute of Petroleum Processing
China Petroleum and Chemical Corp
Original Assignee
Sinopec Research Institute of Petroleum Processing
China Petroleum and Chemical Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sinopec Research Institute of Petroleum Processing, China Petroleum and Chemical Corp filed Critical Sinopec Research Institute of Petroleum Processing
Priority to CN202011193828.5A priority Critical patent/CN114437562B/en
Publication of CN114437562A publication Critical patent/CN114437562A/en
Application granted granted Critical
Publication of CN114437562B publication Critical patent/CN114437562B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/30—Preparation of azo dyes from other azo compounds by esterification of —COOH or —SO3H groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0014—Influencing the physical properties by treatment with a liquid, e.g. solvents
    • C09B67/0015—Influencing the physical properties by treatment with a liquid, e.g. solvents of azoic pigments
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/22—Organic compounds containing nitrogen
    • C10L1/226—Organic compounds containing nitrogen containing at least one nitrogen-to-nitrogen bond, e.g. azo compounds, azides, hydrazines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L10/00—Use of additives to fuels or fires for particular purposes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Color Printing (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

The present disclosure relates to a modified oil dye comprising an oil-soluble oil dye having at least one hydroxyl group replaced by a long chain fatty acid ester group. The modified oil dye provided by the disclosure contains the oil-soluble oil dye with at least one hydroxyl group replaced by a long-chain fatty acid ester group, so that the modified oil dye has higher solubility in an oily solvent and better coloring effect on petroleum products.

Description

Modified oil dye, oil colorant, preparation method and application thereof and colored petroleum product
Technical Field
The disclosure relates to the technical field of petrochemical industry, in particular to a modified oil dye, an oil colorant containing the modified oil dye, a preparation method and application thereof and a colored petroleum product.
Background
To facilitate identification and management of various types of petroleum products and to prevent misuse, most countries and regions color different types of petroleum products. For example, countries such as the united states, canada, belgium, and japan often color petroleum products for different uses or industries to facilitate tax collection at different tax rates.
Among them, azo dyes are most widely used.
However, the above-mentioned colorants have low solubility in petroleum products, resulting in poor coloring effects on petroleum products.
Disclosure of Invention
The purpose of the present disclosure is to provide a modified oil dye, an oil colorant containing the modified oil dye, a preparation method and application thereof, and a colored petroleum product.
To achieve the above object, in a first aspect, the present disclosure provides a modified oil dye comprising an oil-soluble oil dye in which at least one hydroxyl group is substituted with a long-chain fatty acid ester group.
Optionally, the long chain fatty acid has 12-20 carbon atoms;
preferably, the long chain fatty acid comprises at least one of lauric acid, myristic acid, myristoleic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, and arachidic acid;
more preferably, the long chain fatty acid comprises palmitoleic acid and/or oleic acid.
Optionally, the oil-soluble oil dye comprises at least one of azo type dye, anthraquinone type dye and indane type dye;
preferably, the azo dye comprises at least one of sudan red i, sudan red ii, sudan red iii, sudan red iv, oil red 113, solvent red 27, solvent yellow 18, and solvent yellow 12;
the anthraquinone dye comprises solvent red 146 and/or solvent violet 13;
the indane-type dye includes solvent yellow 176 and/or solvent yellow 114.
In a second aspect, the present disclosure provides an oil colorant comprising the modified oil dye of any one of the first aspects.
Optionally, the oil colorant also contains hanging tetrahydrodicyclopentadiene.
Alternatively, the content of the pendant tetrahydrodicyclopentadiene is 10 to 90 wt%, preferably 45 to 55 wt%, and the content of the modified oil dye is 10 to 90 wt%, preferably 45 to 55 wt%, based on the oil colorant.
In a third aspect, the present disclosure provides a method of preparing the oil colorant of any one of the second aspect, the method comprising:
mixing an oil-soluble oil dye, long-chain fatty acid, hanging tetrahydrodicyclopentadiene, a water-carrying agent and a catalyst to obtain a first mixture;
placing the first mixture in an inert gas atmosphere, and reacting for 1-20 h under stirring conditions to obtain a second mixture, wherein the stirring conditions comprise: the rotating speed is 100-600 rpm, and the temperature is 80-180 ℃;
and removing the water carrying agent and the catalyst in the second mixture to obtain the oil colorant.
Optionally, the water-carrying agent comprises at least one of toluene, ethylbenzene and xylene;
the catalyst comprises at least one of sulfuric acid, phosphoric acid, boric acid, copper sulfate, zinc sulfate, cerium sulfate, zinc oxide, tin oxide, tetrabutyl titanate, isopropyl zirconate, p-toluenesulfonic acid, zinc acetate, cation exchange resin, solid super acid, heteropolyacid and titanium silicalite, preferably the catalyst comprises at least one of solid super acid, titanium silicalite and zinc oxide.
In a fourth aspect, the present disclosure provides the use of a modified petroleum dye of any one of the first aspect or of any one of the second aspect in the colouring of an organic product, wherein the organic product comprises at least one of petroleum products including at least one of gasoline, diesel and aviation fuel, organic solvents, lubricating oils, antifreeze, printing inks and plastics.
In a fifth aspect, the present disclosure provides a colored petroleum product comprising the modified petroleum dye of any one of the first aspects or the petroleum colorant of any one of the second aspects.
Through the technical scheme, the modified oil dye provided by the disclosure contains the oil-soluble oil dye with at least one hydroxyl group replaced by the long-chain fatty acid ester group, so that the modified oil dye has higher solubility in an oily solvent and better coloring effect on petroleum products.
Additional features and advantages of the present disclosure will be set forth in the detailed description which follows.
Drawings
The accompanying drawings are included to provide a further understanding of the disclosure, and are incorporated in and constitute a part of this specification, illustrate the disclosure and together with the description serve to explain, but do not limit the disclosure. In the drawings:
fig. 1 is an infrared spectrum of an oil colorant a provided in an embodiment of the present disclosure.
Detailed Description
The following describes specific embodiments of the present disclosure in detail. It should be understood that the detailed description and specific examples, while indicating and illustrating the disclosure, are not intended to limit the disclosure.
A first aspect of the present disclosure provides a modified oil dye comprising an oil-soluble oil dye having at least one hydroxyl group replaced with a long chain fatty acid ester group.
In the embodiment of the disclosure, specifically, the modified oil dye may be a product obtained after an esterification reaction between at least one hydroxyl group in the oil-soluble oil dye and a long-chain fatty acid. Because the molecular structure of the modified oil dye has free long-chain fatty acid ester groups, the solubility of the modified oil dye in an oily solvent is obviously improved, and the coloring effect of the modified oil dye on petroleum products can be effectively improved.
According to the present disclosure, the long chain fatty acid may include saturated fatty acids and unsaturated fatty acids, wherein the number of carbon atoms of the long chain fatty acids may vary within a certain range, for example, the number of carbon atoms of the long chain fatty acids may be 12 to 20; preferably, the long chain fatty acid may include at least one of lauric acid, myristic acid, myristoleic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, and arachidic acid; more preferably, the long chain fatty acid may comprise palmitoleic acid and/or oleic acid.
According to the present disclosure, the oil-soluble oil dye may be selected within a wide range, for example, the oil-soluble oil dye may include at least one of azo-type dye, anthraquinone-type dye, and indane-type dye; preferably, the azo dye may include at least one of sudan red i, sudan red ii, sudan red iii, sudan red iv, oil red 113, solvent red 27, solvent yellow 18, and solvent yellow 12; the anthraquinone-type dye may include solvent red 146 and/or solvent violet 13; the indane-type dye may include solvent yellow 176 and/or solvent yellow 114.
Illustratively, when the long-chain fatty acid is oleic acid and the oil-soluble oil dye is sudan III, the modified oil dye can be sudan III oleate generated by esterification of oleic acid with sudan III. Wherein, the chemical structural formula of oleic acid is:
the chemical structural formula of sudan III is:
the chemical structural formula of sudan red III oleate is as follows:
a second aspect of the present disclosure provides an oil colorant comprising the modified oil dye of any one of the first aspects.
Optionally, the oil colorant also contains hanging tetrahydrodicyclopentadiene.
In the examples of the present disclosure, in particular, the pendant tetrahydrodicyclopentadiene is obtained from the hydroisomerization of dicyclopentadiene, which has a high density (0.94 g/cm 3 ) Low freezing point (-79 ℃), and the like, and still has very good transportation performance under severe cold conditions. In addition, the pendant tetrahydrodicyclopentadiene is less toxic and almost odorless. Thus, the pendant tetrahydrodicyclopentadiene isA low-toxicity and environment-friendly high-quality solvent.
The hanging tetrahydrodicyclopentadiene has obvious dissolving effect on the modified oil dye, has higher solubility in petroleum products, and can obviously improve the concentration of the modified oil dye in the oil colorant when used for preparing the oil colorant, and quicken the dissolving speed of the oil colorant in the petroleum products, thereby further improving the coloring effect of the oil colorant on the petroleum products.
According to the present disclosure, the contents of the pendant tetrahydrodicyclopentadiene and the modified oil dye in the oil colorant may vary within a certain range, for example, the pendant tetrahydrodicyclopentadiene may be 10 to 90 wt%, preferably 45 to 55 wt%, and the modified oil dye may be 10 to 90 wt%, preferably 45 to 55 wt%, based on the oil colorant.
A third aspect of the present disclosure provides a method of preparing the oil colorant of any one of the second aspect, the method comprising: mixing an oil-soluble oil dye, long-chain fatty acid, hanging tetrahydrodicyclopentadiene, a water-carrying agent and a catalyst to obtain a first mixture; placing the first mixture in an inert gas atmosphere, and reacting for 1-20 h under stirring conditions to obtain a second mixture, wherein the stirring conditions comprise: the rotating speed is 100-600 rpm, and the temperature is 80-180 ℃; and removing the water carrying agent and the catalyst in the second mixture to obtain the oil colorant.
The method provided by the disclosure has the advantages of simplicity and easiness.
In the embodiment of the disclosure, specifically, when the first mixture is placed in an inert gas atmosphere, inert gas may be continuously introduced into the first mixture, so that the rate of generating bubbles in the first mixture by the inert gas is 10-30 bubbles/min. The inert gas may include, for example, nitrogen, argon, and carbon dioxide.
When the first mixture is reacted to obtain a second mixture, the reaction time is preferably 2 to 10 hours, more preferably 2 to 4 hours; the rotation speed is preferably 200 to 400 rpm, and more preferably 220 to 300 rpm; the temperature is preferably 90 to 160℃and more preferably 110 to 130 ℃.
After the second mixture is obtained, the water-carrying agent can be removed by distillation or reduced pressure distillation, and the catalyst can be removed by filtration.
Optionally, the water-carrying agent comprises at least one of toluene, ethylbenzene and xylene; the catalyst comprises at least one of sulfuric acid, phosphoric acid, boric acid, copper sulfate, zinc sulfate, cerium sulfate, zinc oxide, tin oxide, tetrabutyl titanate, isopropyl zirconate, p-toluenesulfonic acid, zinc acetate, cation exchange resin, solid super acid, heteropolyacid and titanium silicalite, preferably the catalyst comprises at least one of solid super acid, titanium silicalite and zinc oxide.
A fourth aspect of the present disclosure provides the use of the modified oil dye of any one of the first aspect or the oil colorant of any one of the second aspect in the colouring of an organic product, wherein the organic product comprises at least one of a petroleum product comprising at least one of gasoline, diesel and aviation fuel, an organic solvent, a lubricating oil, an antifreeze fluid, a printing ink and a plastic.
A fifth aspect of the present disclosure provides a colored petroleum product comprising the modified petroleum dye of any one of the first aspects or the petroleum colorant of any one of the second aspects.
In particular, in embodiments of the present disclosure, colored petroleum products may be derived from conventional petroleum products that may include, for example, at least one of gasoline, diesel, and aviation fuel, after being colored with an oil colorant.
The present disclosure is further illustrated by the following examples, but the present disclosure is not limited thereby.
The materials, reagents, instruments and equipment involved in the embodiments of the disclosure, unless otherwise specified, are all commercially available. In addition, the test temperatures in the examples of the present disclosure, unless otherwise specified, may be room temperature (25 ℃).
Example 1
This example is used to prepare the oil colorants of the present disclosure.
(1) Uniformly mixing 25.0g of oil-soluble oil dye (sudan red III), 20.0g of long-chain fatty acid (oleic acid), 43.8g of hanging tetrahydrodicyclopentadiene and 30g of water-carrying agent (toluene), and then adding 0.45g of catalyst (zinc oxide) to obtain a first mixture;
(2) Continuously introducing nitrogen into the first mixture to ensure that the generation rate of nitrogen bubbles is 10-30 per minute, and then carrying out esterification reaction for 3 hours under stirring conditions to obtain a second mixture, wherein the stirring conditions comprise: the rotating speed is 240 r/min, the temperature is 110 ℃, and a water diversion device (such as a water diversion device) is utilized to reflux a water carrying agent (toluene) and carry out water generated by the esterification reaction in the esterification reaction process;
(3) And (3) reducing the temperature of the second mixture to 50-60 ℃, then filtering to remove the catalyst (zinc oxide), collecting filtrate, and performing reduced pressure distillation to remove the water carrying agent (toluene) to obtain the oil colorant A.
Appearance detection is carried out on the oil colorant A, and the detection result shows that the oil colorant A is transparent clear solution and the sudan red III dye is completely dissolved.
The oil colorant A prepared in this embodiment comprises hanging tetrahydrodicyclopentadiene and a modified oil dye (sudan III oleate) dissolved therein, wherein the modified oil dye (sudan III oleate) is obtained by esterification reaction of an oil-soluble oil dye (sudan III) and long-chain fatty acid (oleic acid). Wherein, based on the oil colorant A, the content of the hanging tetrahydrodicyclopentadiene is 50 percent by weight, and the content of the modified oil dye (sudan red III oleate) is 50 percent by weight.
Example 2
This example is used to prepare the oil colorants of the present disclosure.
(1) Uniformly mixing 17.6g of oil-soluble oil dye (sudan red I), 18.2g of long-chain fatty acid (palmitoleic acid), 3.8g of hanging tetrahydrodicyclopentadiene and 30g of water-carrying agent (toluene), and then adding 2g of catalyst (solid super acid) to obtain a first mixture;
(2) Continuously introducing nitrogen into the first mixture to ensure that the generation rate of nitrogen bubbles is 10-30 per minute, and then carrying out esterification reaction for 2 hours under stirring conditions to obtain a second mixture, wherein the stirring conditions comprise: the rotating speed is 280 r/min, the temperature is 110 ℃, and a water-carrying agent (toluene) is refluxed by a water-dividing device (for example, a water-dividing device) and carries out the water generated by the esterification reaction in the esterification reaction process;
(3) And (3) reducing the temperature of the second mixture to 50-60 ℃, then filtering to remove the catalyst (solid super acid), collecting filtrate, and performing reduced pressure distillation to remove the water-carrying agent (toluene) to obtain the oil colorant B.
Appearance detection is carried out on the oil colorant B, and the detection result shows that the oil colorant B is transparent clear solution and the sudan red I dye is completely dissolved.
The oil colorant B prepared in this embodiment comprises hanging tetrahydrodicyclopentadiene and a modified oil dye (Sudan red I palmitoleic acid ester) dissolved therein, wherein the modified oil dye (Sudan red I palmitoleic acid ester) is obtained by esterification reaction of an oil-soluble oil dye (Sudan red I) and long-chain fatty acid (palmitoleic acid). Wherein, based on the oil colorant B, the content of the hanging tetrahydrodicyclopentadiene is 10 percent by weight, and the content of the modified oil dye (Sudan red I palm oleate) is 90 percent by weight.
Example 3
This example is used to prepare the oil colorants of the present disclosure.
(1) Uniformly mixing 10.0g of oil-soluble oil dye (Sudan red II), 7.2g of long-chain fatty acid (lauric acid), 150.0g of hanging tetrahydrodicyclopentadiene and 30g of water-carrying agent (toluene), and then adding 0.4g of catalyst (titanium silicalite molecular sieve) to obtain a first mixture;
(2) Continuously introducing nitrogen into the first mixture to ensure that the generation rate of nitrogen bubbles is 10-30 per minute, and then carrying out esterification reaction for 10 hours under stirring conditions to obtain a second mixture, wherein the stirring conditions comprise: the rotating speed is 250 r/min, the temperature is 110 ℃, and a water-carrying agent (toluene) is refluxed by a water-dividing device (for example, a water-dividing device) and carries out the water generated by the esterification reaction in the esterification reaction process;
(3) And (3) reducing the temperature of the second mixture to 50-60 ℃, then filtering to remove the catalyst (titanium-silicon molecular sieve), collecting filtrate, and performing reduced pressure distillation to remove the water carrying agent (toluene) to obtain the oil colorant C.
Appearance detection is carried out on the oil colorant C, and the detection result shows that the oil colorant C is transparent clear solution and the sudan red II dye is completely dissolved.
The oil colorant C prepared in this embodiment comprises hanging tetrahydrodicyclopentadiene and a modified oil dye (sudan red II laurate) dissolved therein, wherein the modified oil dye (sudan red II laurate) is obtained by esterification reaction of an oil-soluble oil dye (sudan red II) and long-chain fatty acid (lauric acid). Wherein, based on the oil colorant C, the content of the hanging tetrahydrodicyclopentadiene is 90 percent by weight, and the content of the modified oil dye (sudan II laurate) is 10 percent by weight.
Example 4
This example is used to prepare the oil colorants of the present disclosure.
(1) Uniformly mixing 15g of oil-soluble oil dye (sudan IV), 8.9g of long-chain fatty acid (myristoleic acid), 19.1g of hanging tetrahydrodicyclopentadiene and 30g of water-carrying agent (toluene), and then adding 2g of catalyst (cation exchange resin) to obtain a first mixture;
(2) Continuously introducing nitrogen into the first mixture to ensure that the generation rate of nitrogen bubbles is 10-30 per minute, and then carrying out esterification reaction for 4 hours under stirring conditions to obtain a second mixture, wherein the stirring conditions comprise: the rotating speed is 300 r/min, the temperature is 110 ℃, and a water-carrying agent (toluene) is refluxed by a water-dividing device (for example, a water-dividing device) and carries out the water generated by the esterification reaction in the esterification reaction process;
(3) And (3) reducing the temperature of the second mixture to 50-60 ℃, then filtering to remove the catalyst (cation exchange resin), collecting filtrate, and performing reduced pressure distillation to remove the water carrying agent (toluene) to obtain the oil colorant D.
Appearance detection is carried out on the oil colorant D, and the detection result shows that the oil colorant D is transparent clear solution and the sudan red IV dye is completely dissolved.
The oil colorant D prepared in this embodiment comprises hanging tetrahydrodicyclopentadiene and a modified oil dye (sudan IV myristoleate) dissolved therein, wherein the modified oil dye (sudan IV myristoleate) is obtained by esterification reaction of an oil-soluble oil dye (sudan IV) and long-chain fatty acid (myristoleate). Wherein, the content of the hanging tetrahydrodicyclopentadiene is 45 weight percent and the content of the modified oil dye (sudan IV myristoleate) is 55 weight percent based on the oil colorant D.
Example 5
This example is used to prepare the oil colorants of the present disclosure.
(1) Uniformly mixing 15.0g of oil-soluble oil dye (solvent red 146), 12.9g of long-chain fatty acid (stearic acid), 33.1g of hanging tetrahydrodicyclopentadiene and 30g of water-carrying agent (toluene), and then adding 0.3g of catalyst (zinc oxide) to obtain a first mixture;
(2) Continuously introducing nitrogen into the first mixture to ensure that the generation rate of nitrogen bubbles is 10-30 per minute, and then carrying out esterification reaction for 8 hours under stirring conditions to obtain a second mixture, wherein the stirring conditions comprise: the rotating speed is 300 r/min, the temperature is 110 ℃, and a water-carrying agent (toluene) is refluxed by a water-dividing device (for example, a water-dividing device) and carries out the water generated by the esterification reaction in the esterification reaction process;
(3) And (3) reducing the temperature of the second mixture to 50-60 ℃, then filtering to remove the catalyst (zinc oxide), collecting filtrate, and performing reduced pressure distillation to remove the water carrying agent (toluene) to obtain the oil colorant E.
Appearance detection is carried out on the oil colorant E, and the detection result shows that the oil colorant E is transparent and clear solution, and the solvent red 146 dye is completely dissolved.
The oil colorant E prepared in this embodiment comprises a pendant tetrahydrodicyclopentadiene and a modified oil dye (solvent red 146 stearate) dissolved therein, wherein the modified oil dye (solvent red 146 stearate) is obtained by esterification reaction of an oil-soluble oil dye (solvent red 146) and long-chain fatty acid (stearic acid). Wherein, based on the oil colorant E, the content of the hanging tetrahydrodicyclopentadiene is 55 weight percent, and the content of the modified oil dye (solvent red 146 stearate) is 45 weight percent.
Example 6
The oil colorant F of this example was prepared as in example 1, except that: solvent yellow 176 was used instead of sudan red iii in example 1.
Example 7
The oil colorant G of this example was prepared as in example 1, except that: oil red 113 was used instead of sudan red iii in example 1.
Example 8
The oil colorant H of this example was prepared as in example 1, except that: solvent red 27 was used to replace sudan red iii in example 1.
Example 9
The oil colorant I of this example was prepared as in example 1, except that: solvent yellow 18 was used instead of sudan red iii in example 1.
Example 10
The oil colorant J of this example was prepared as in example 1, except that: solvent yellow 12 was used instead of sudan red iii in example 1.
Example 11
The oil colorant K of this example was prepared as in example 1, except that: solvent violet 13 was used to replace sudan red iii in example 1.
Example 12
The oil colorant L of this example was prepared as in example 1, except that: solvent yellow 114 was used instead of sudan red iii in example 1.
Test example 1
And detecting the solubility of each oil coloring agent in the gasoline and the time required for complete dissolution according to the national standard, and calculating the actual content of the oil-soluble dye in each oil coloring agent in the gasoline. The types of the oil colorants and the detection results thereof are shown in table 1.
TABLE 1
Note that: in table 1, "Σ" indicates the solubility of the oil colorant in gasoline, and the greater the "Σ" amount, the greater the solubility of the oil colorant in gasoline.
As can be seen from table 1, the modified oil dye in the oil colorant provided by the present disclosure has a high concentration, good coloring effect on petroleum products, and can be rapidly and sufficiently dissolved in petroleum products.
Test example 2
The oil colorant A prepared in example 1 was subjected to infrared detection, and the detection result is shown in FIG. 1.
As can be seen from FIG. 1, 3400cm of infrared spectrum does not appear -1 The nearby stretching vibration peak indicates that the hydroxyl group in the molecular structure of Sudan red III has been completely esterified.
In the infrared spectrum, the wave number is 3008cm -1 、2921cm -1 And 2848cm -1 The infrared peak appearing nearby is the stretching vibration peak of alkyl CH; wave number 1738cm -1 The infrared peak appearing nearby is the vibration absorption peak of c=o; wave number 1459cm -1 The infrared peak appearing nearby is a stretching vibration peak of n=n; wave number 1432cm -1 The infrared peak appearing nearby is the stretching vibration peak of aromatic ring c=c; wave number 1194cm -1 The nearby infrared peak is a C-N stretching vibration peak; wave number 1016cm -1 、833cm -1 The infrared peak appearing nearby is the bending vibration peak of the aromatic ring CH; wave number 1358cm -1 、1239cm -1 NearbyThe infrared peak is the bending vibration peak of benzene ring CH; wave number 1166cm -1 The infrared peak appearing nearby is the stretching vibration peak of ester group C-O; wave number 714cm -1 The near infrared peak is alkyl (-CH) 2 (-) characteristic peak (n is greater than 4).
It can be seen that in the oil colorant A, the carboxyl group of the long-chain fatty acid (oleic acid) and the hydroxyl group of the oil-soluble oil dye (Sudan red III) have completely undergone esterification reaction.
Similarly, the esterification reaction of the carboxyl of the long-chain fatty acid in the oil coloring agents B-L and the hydroxyl of the oil-soluble oil dye can be detected and proved.
The preferred embodiments of the present disclosure have been described in detail above, but the present disclosure is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solutions of the present disclosure within the scope of the technical concept of the present disclosure, and all the simple modifications belong to the protection scope of the present disclosure.
In addition, the specific features described in the foregoing embodiments may be combined in any suitable manner, and in order to avoid unnecessary repetition, the present disclosure does not further describe various possible combinations.
Moreover, any combination between the various embodiments of the present disclosure is possible as long as it does not depart from the spirit of the present disclosure, which should also be construed as the disclosure of the present disclosure.

Claims (13)

1. The oil colorant is characterized by comprising a modified oil dye and a pendant tetrahydrodicyclopentadiene, wherein the modified oil dye comprises an oil-soluble oil dye with at least one hydroxyl group replaced by a long-chain fatty acid ester group.
2. The oil colorant of claim 1 wherein said long chain fatty acid has 12 to 20 carbon atoms.
3. The oil colorant of claim 2 wherein said long chain fatty acids comprise at least one of lauric acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, and arachidic acid.
4. An oil colorant according to claim 3, wherein the long chain fatty acids comprise palmitoleic acid and/or oleic acid.
5. The oil colorant of claim 1 wherein the oil-soluble oil dye comprises at least one of azo-type dyes, anthraquinone-type dyes, and indane-type dyes.
6. The oil colorant of claim 5 wherein said azo dye comprises at least one of sudan red i, sudan red ii, sudan red iii, sudan red iv, oil red 113, solvent red 27, solvent yellow 18, and solvent yellow 12;
the anthraquinone dye comprises solvent red 146 and/or solvent violet 13;
the indane-type dye includes solvent yellow 176 and/or solvent yellow 114.
7. The oil colorant according to claim 1, wherein the pendant tetrahydrodicyclopentadiene is 10-90 wt% and the modified oil dye is 10-90 wt% based on the oil colorant.
8. The oil colorant according to claim 7, wherein the pendant tetrahydrodicyclopentadiene is 45-55 wt% and the modified oil dye is 45-55 wt% based on the oil colorant.
9. A process for preparing the oil stain of claim 1, comprising:
mixing an oil-soluble oil dye, long-chain fatty acid, hanging tetrahydrodicyclopentadiene, a water-carrying agent and a catalyst to obtain a first mixture;
placing the first mixture in an inert gas atmosphere, and reacting for 1-20 h under stirring conditions to obtain a second mixture, wherein the stirring conditions comprise: the rotating speed is 100-600 rpm, and the temperature is 80-180 ℃;
and removing the water carrying agent and the catalyst in the second mixture to obtain the oil colorant.
10. The method of claim 9, wherein the water-carrying agent comprises at least one of toluene, ethylbenzene, and xylenes;
the catalyst comprises at least one of sulfuric acid, phosphoric acid, boric acid, copper sulfate, zinc sulfate, cerium sulfate, zinc oxide, tin oxide, tetrabutyl titanate, isopropyl zirconate, p-toluenesulfonic acid, zinc acetate, cation exchange resin, solid super acid, heteropolyacid and titanium silicalite molecular sieve.
11. The method of claim 10, wherein the catalyst comprises at least one of a solid super acid, a titanium silicalite, and zinc oxide.
12. Use of the oil colorant of any of claims 1-8 for coloring organic products, wherein the organic products comprise petroleum products including at least one of gasoline, diesel oil, and aviation fuel, organic solvents, lubricating oils, antifreeze, printing inks, and plastics.
13. A coloured petroleum product, characterised in that it contains an oil colourant according to any of claims 1 to 8.
CN202011193828.5A 2020-10-30 2020-10-30 Modified oil dye, oil colorant, preparation method and application thereof and colored petroleum product Active CN114437562B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202011193828.5A CN114437562B (en) 2020-10-30 2020-10-30 Modified oil dye, oil colorant, preparation method and application thereof and colored petroleum product

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202011193828.5A CN114437562B (en) 2020-10-30 2020-10-30 Modified oil dye, oil colorant, preparation method and application thereof and colored petroleum product

Publications (2)

Publication Number Publication Date
CN114437562A CN114437562A (en) 2022-05-06
CN114437562B true CN114437562B (en) 2024-02-09

Family

ID=81357132

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202011193828.5A Active CN114437562B (en) 2020-10-30 2020-10-30 Modified oil dye, oil colorant, preparation method and application thereof and colored petroleum product

Country Status (1)

Country Link
CN (1) CN114437562B (en)

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1334596A (en) * 1970-05-15 1973-10-24 Ciba Geigy Ag Disazo pigments containing hydrazide groups and process for their manufacture
US4305729A (en) * 1981-02-23 1981-12-15 Suntech, Inc. Carbon slurry fuels
US4739042A (en) * 1985-08-08 1988-04-19 Bayer Aktiengesellschaft Halftone gravure printing inks containing pyridone azo dyestuffs
CN1150447A (en) * 1994-03-02 1997-05-21 威廉·C·奥尔 Unleaded MMT fuel compositions
US8298298B1 (en) * 2010-12-22 2012-10-30 Empire Development Technology LLC Dyes with changeable solubilities, and methods for their use
CN108727264A (en) * 2017-04-21 2018-11-02 斯佩特罗尼克斯公司 The preparation method and combinations thereof of naphthalimide diester fluorescent dye
CN111621345A (en) * 2020-05-27 2020-09-04 北京化工大学 Cyclopropanation polycyclic terpenoid compound and preparation method and application thereof

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1334596A (en) * 1970-05-15 1973-10-24 Ciba Geigy Ag Disazo pigments containing hydrazide groups and process for their manufacture
US4305729A (en) * 1981-02-23 1981-12-15 Suntech, Inc. Carbon slurry fuels
US4739042A (en) * 1985-08-08 1988-04-19 Bayer Aktiengesellschaft Halftone gravure printing inks containing pyridone azo dyestuffs
CN1150447A (en) * 1994-03-02 1997-05-21 威廉·C·奥尔 Unleaded MMT fuel compositions
US8298298B1 (en) * 2010-12-22 2012-10-30 Empire Development Technology LLC Dyes with changeable solubilities, and methods for their use
CN108727264A (en) * 2017-04-21 2018-11-02 斯佩特罗尼克斯公司 The preparation method and combinations thereof of naphthalimide diester fluorescent dye
CN111621345A (en) * 2020-05-27 2020-09-04 北京化工大学 Cyclopropanation polycyclic terpenoid compound and preparation method and application thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
酞菁型溶剂染料;沈美琴;;染料与染色(第03期);13-17 *

Also Published As

Publication number Publication date
CN114437562A (en) 2022-05-06

Similar Documents

Publication Publication Date Title
CN113508153B (en) Method for producing decolorized polyester, and decolorizer
CA2548019C (en) Polymeric dispersant
CN101987932A (en) High-temperature steam endurance ink for spraying code and printing
US2821530A (en) Tetrahalogen substituted quinacridones
CN114437562B (en) Modified oil dye, oil colorant, preparation method and application thereof and colored petroleum product
CN1054878C (en) Use of azo dyes for marking hydrocarbons and novel azo dyes
JP2020176258A (en) Colored polyester and production method of recycled polyethylene terephthalate
CN110643022A (en) Modified light-cured polyester acrylic resin and synthetic method thereof
US5626634A (en) Aqueous compositions of solvent-soluble dyestuffs
CN117757301A (en) Environment-friendly high-gloss water-based ink and preparation method thereof
DE905736C (en) Process for the preparation of ethylene glycol esters of terephthalic acid
GB2472676A (en) Citryl methacrylate monomers, polymers, dispersions, and inks
DE1916175C3 (en) Process for the preparation of colored polymers and copolymers
CN104744678A (en) Alkyd resin and preparation method thereof
US3707347A (en) Staining plastic surfaces
CN114437840B (en) Oil coloring agent, preparation method and application thereof and colored petroleum product
DE1544386A1 (en) Process for the preparation of liquid or low-melting p-aminoazo dyes
EP1058716B1 (en) Pigment preparations containing an acrylic resin
CN101294005A (en) Red naphtocyclinon solvent dye and preparation method thereof
CA2448441C (en) Composition
DE743848C (en) Process for the preparation of salts of water-insoluble azo dyes containing metal in complex bonds
DE2016719A1 (en)
US6734242B2 (en) Composition
CN1041320C (en) Natural gulf red priming paint with rust
DE1916012A1 (en) Copolymerizable dyes of the tetrahydrotetraazaporphine group and polymers obtained from these dyes

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant