CN107937027B - Aromatic-hydrocarbon-containing low-viscosity rubber plasticizer and preparation method thereof - Google Patents

Aromatic-hydrocarbon-containing low-viscosity rubber plasticizer and preparation method thereof Download PDF

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CN107937027B
CN107937027B CN201711227886.3A CN201711227886A CN107937027B CN 107937027 B CN107937027 B CN 107937027B CN 201711227886 A CN201711227886 A CN 201711227886A CN 107937027 B CN107937027 B CN 107937027B
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oil
reaction
viscosity
aromatic hydrocarbon
low
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CN107937027A (en
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于恩强
冯涛
李军
马志远
王瑞瑞
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China Offshore Bitumen Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G67/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only
    • C10G67/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only
    • C10G67/14—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only including at least two different refining steps in the absence of hydrogen
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1037—Hydrocarbon fractions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/201—Impurities
    • C10G2300/202—Heteroatoms content, i.e. S, N, O, P
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/30—Physical properties of feedstocks or products
    • C10G2300/302—Viscosity
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/30—Aromatics

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Lubricants (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

Abstract

The invention discloses a low-viscosity rubber plasticizer containing aromatic hydrocarbon and a preparation method thereof. The preparation method comprises the following steps: (1) carrying out hydrogenation reaction on the distillate oil to obtain hydrogenated oil; (2) carrying out liquid-phase denitrification reaction on the hydrogenated oil, and removing nitrogen slag to obtain denitrified oil; (3) and carrying out adsorption reaction on the denitrified oil to obtain the low-viscosity rubber plasticizer containing aromatic hydrocarbon. The rubber plasticizer disclosed by the invention has the advantages of low viscosity, light color, high aromatic hydrocarbon content and good compatibility with rubber, and can effectively improve the processability of the rubber.

Description

Aromatic-hydrocarbon-containing low-viscosity rubber plasticizer and preparation method thereof
Technical Field
The invention relates to a low-viscosity rubber plasticizer containing aromatic hydrocarbon and a preparation method thereof, belonging to the field of petrochemical product processing.
Background
In order to improve the properties of rubber, such as elasticity, flexibility, workability, and kneading easiness, a specific rubber plasticizer is usually added for the purpose. The rubber plasticizer is added into the rubber, so that the acting force between rubber molecular chains can be reduced, the powdery compounding agent and the raw rubber are well soaked, and the mixing process is improved; the compounding agent is dispersed uniformly, the mixing time is shortened, the energy consumption is reduced, and the heat generation phenomenon in the mixing process can be reduced; meanwhile, the plasticity, the fluidity and the adhesiveness of the rubber material can be increased, and the process operations such as calendering, extrusion, molding and the like are facilitated.
Because the aromatic oil has good compatibility with rubber and can endow rubber products with good performance, the aromatic oil is most widely applied to oil-extended rubber and other rubber product enterprises. However, with the increasing concern of human beings on their health and living environment, the safety problem of aromatic oil has also received high attention. Under the influence of laws and regulations of the European Union, the United states, Japan and other relevant countries on the environmental protection requirements of rubber products, rubber plasticizer enterprises at home and abroad are also actively responding to the laws and regulations and the regulations, and the relevant environmental protection type rubber plasticizers are introduced. However, most of the environment-friendly rubber plasticizers in the current market are dark products with high viscosity, and the viscosity is high, so that the environment-friendly rubber plasticizers are not suitable for the processing process of some rubber products requiring high softening performance.
Disclosure of Invention
The invention aims to provide a low-viscosity rubber plasticizer containing aromatic hydrocarbon and a preparation method thereof.
The invention provides a preparation method of a low-viscosity rubber plasticizer containing aromatic hydrocarbon, which comprises the following steps: (1) carrying out hydrogenation reaction on the distillate oil to obtain hydrogenated oil;
(2) carrying out liquid-phase denitrification reaction on the hydrogenated oil, and removing nitrogen slag to obtain denitrified oil;
(3) and carrying out adsorption reaction on the denitrified oil to obtain the low-viscosity rubber plasticizer containing aromatic hydrocarbon.
In the preparation method, the crude oil of the distillate oil comprises intermediate groups and naphthenic groups;
the kinematic viscosity of the distillate oil at 40 ℃ is 7-40 mm2The distillation range is 250-370 ℃.
In the above preparation method, the distillate is at least one selected from the group consisting of a normal second-line distillate, a normal third-line distillate and a reduced first-line distillate of the crude oil.
In the above preparation method, the hydrogenation reaction conditions are as follows: the hydrogen partial pressure is 2-15 MPa, specifically 3MPa, 6.5MPa, 7MPa or 3-7 MPa, the reaction temperature is 250-370 ℃, specifically 300 ℃, 320 ℃, 330 ℃ or 300-330 ℃, the reaction time is 10-60 min, specifically 10min, 15min, 30min, 10-30 min or 10-60 min, and the volume space velocity is 0.5-3.0 h-1Specifically, it can be 0.5h-1、0.6h-1、1.0h-1Or 0.5 to 1.0h-1The volume ratio of the hydrogen to the distillate oil is 400-1000: 1, specifically 400:1, 400-600: 1, 400-800: 1 or 400-900: 1;
the catalyst adopted in the hydrogenation reaction is at least one amorphous silica-alumina catalyst in nickel-molybdenum, nickel-tungsten, cobalt-molybdenum, molybdenum-cobalt-nickel and molybdenum-nickel-tungsten types.
The above catalysts, amorphous silica-alumina catalysts of the nickel-molybdenum, nickel-tungsten, cobalt-molybdenum, molybdenum-cobalt-nickel and molybdenum-nickel-tungsten type, are all catalysts commonly used in the art.
In the above preparation method, the mass percentage of the added denitrifier for the liquid phase denitrification reaction is 1 to 8 permillage of the hydrogenated oil, specifically 3 permillage, 5 permillage, 6 permillage or 1 to 6 permillage;
the denitrifier is Lewis acid compound type, and specifically can be at least one of WSQ-2, WSQ-5, titanium tetrachloride and titanium sulfate organic solution;
the temperature of the liquid phase denitrification reaction is 50-100 ℃, specifically 70 ℃, 90 ℃, 95 ℃ or 70-95 ℃, and the reaction time is 10-60 min, specifically 20min, 30min, 40min or 20-40 min.
In the present invention, the treatment of removing the nitrogen slag in step 2) is a technique well known to those skilled in the art, and is removed by a strong electric field and gravity.
In the preparation method, the adsorbent used in the adsorption reaction is argil;
the mass percentage of the clay added is 0.5-10% of the denitrified oil, and specifically can be 3%, 5%, 8% or 3-8%;
the temperature of the adsorption reaction can be 100-160 ℃, specifically 100 ℃, 120 ℃, 140 ℃ or 100-140 ℃, and the time can be 10-60 min, specifically 30min, 60min or 30-60 min.
The invention also provides the low-viscosity rubber plasticizer containing the aromatic hydrocarbon, which is obtained by the preparation method.
The performance parameters of the low-viscosity rubber plasticizer containing aromatic hydrocarbon are as follows: the kinematic viscosity at 40 ℃ is 6-30 mm2The aromatic carbon rate is 10 to 15 percent, the aniline point is less than 80 ℃, the benzopyrene is less than 1mg/kg, and the polycyclic aromatic hydrocarbon is less than 10 mg/kg; polycyclic Aromatic Hydrocarbons (PAHs) include at least one of benzo (a) pyrene, benzo (e) pyrene, benzo (a) anthracene, chrysene, benzo (b) fluoranthene, benzo (j) fluoranthene, benzo (k) fluoranthene, and dibenzo (a, h) anthracene.
In the present invention, benzo (a) pyrene, benzo (e) pyrene, benzo (a) anthracene, chrysene, benzo (b) fluoranthene, benzo (j) fluoranthene, benzo (k) fluoranthene, and dibenzo (a, h) anthracene are abbreviated as BaP, BeP, BaA, CHR, BbFA, BjFA, bkffa, and DBAhA, respectively.
Compared with the commonly adopted hydrogenation technology, the method has the advantages that the raw materials are subjected to appropriate deep hydrofining, the cracking of excessive aromatic hydrocarbon is avoided, more aromatic hydrocarbon is reserved, meanwhile, in order to avoid the influence of miscellaneous elements such as alkaline nitrogen on the stability of the product, the miscellaneous elements are removed by liquid-phase denitrification and clay adsorption refining, and therefore the low-viscosity rubber plasticizer containing the aromatic hydrocarbon is produced. The product of the invention has higher aromatic hydrocarbon content, better compatibility with rubber and better service performance. Compared with the common solvent refining process, the product provided by the invention has higher target product yield, lighter color and better economic benefit.
The low-viscosity rubber plasticizer containing aromatic hydrocarbon has the following advantages:
1. the viscosity is low. The kinematic viscosity of the product at 40 ℃ is 6-30 mm2And/s, the lower viscosity is beneficial to improving the softening performance in the rubber processing process.
2. The color was light. The product of the invention has light color and can be used for various light-colored rubber products.
3. The aromatic hydrocarbon content is high. Aromatic carbon rate C of the product of the inventionAThe value can reach 9% -15%, the compatibility with rubber is good, the rubber plasticizer can fully play a role in the manufacturing process of rubber products, and the processing and use performance of the rubber products are improved.
4. Meets the environmental protection requirement of European Union and is an environmental protection product. The product of the invention meets the limited conditions in the European Union REACH regulation: the content of benzopyrene is less than 1ppm, the total content of polycyclic aromatic hydrocarbon is less than 10ppm, and the product is environment-friendly.
5. Rich resources and stable production. The raw materials of the product of the invention adopt general distillate oil which is sold in the market, the source is rich, and the stable production of the low-viscosity green environment-friendly rubber plasticizer containing aromatic hydrocarbon can be ensured.
Detailed Description
The experimental procedures used in the following examples are all conventional procedures unless otherwise specified.
Materials, reagents and the like used in the following examples are commercially available unless otherwise specified.
The feed distillates used in the following examples were intermediate base and naphthenic distillate with properties as shown in table 1.
TABLE 1 Properties of the distillates
Figure BDA0001487602240000031
EXAMPLE 1 preparation of Low viscosity aromatic-containing rubber plasticizer
The naphthenic normal second-line distillate oil is used as a raw material, the mass ratio of hydrogen to the normal second-line distillate oil of the intermediate base is 400:1 at the pressure of 3MPa and the temperature of 330 ℃, and the volume space velocity is 0.6h-1Carrying out hydrofining (refining time is 10min) under the hydrogenation condition of (2) to obtain hydrogenated oil; the hydrogenated oil is refined by liquid phase denitrification, the dosage of the denitrification agent is 3 per mill of the mass percentage of the hydrogenated oil, and the liquid phase denitrification refining temperature is 70 ℃ (the liquid phase denitrification time is 20min), so as to obtain the denitrified oil; and (3) adsorbing and refining the denitrified oil by using clay, wherein the using amount of the clay is 3 percent of the weight percentage content of the denitrified oil, the adsorption and refining temperature is 100 ℃, and the adsorption and refining time is 30min, so that the low-viscosity rubber plasticizer containing the aromatic hydrocarbon (also called low-viscosity green environment-friendly rubber plasticizer containing the aromatic hydrocarbon) is obtained.
The properties of the low-viscosity green and environment-friendly rubber plasticizer containing aromatic hydrocarbons according to the present invention are shown in table 2.
Table 2 product properties of example 1 of the invention
Figure BDA0001487602240000041
In Table 2 above, CARefers to the aromatic carbon number, i.e., the percentage of carbon number on the aromatic ring to the total carbon number; cNRefers to the naphthenic carbon rate, i.e., the percentage of carbon numbers on the naphthenic hydrocarbon to the total carbon number; cPRefers to the alkane carbon number, i.e., the number of carbons on an alkane as a percentage of the total carbon numberAnd (4) dividing the ratio.
As can be seen from Table 2, the aromatic hydrocarbon-containing low-viscosity green environment-friendly rubber plasticizer has the viscosity of 9.02 at 40 ℃ and is low in viscosity; the product has the chroma of less than 0.1 and light color, and meets the requirement on color in the processing process of light-colored rubber products; the aromatic carbon rate of the product is 12.2 percent, and the requirement on a plasticizer in the rubber processing process is met; the content of benzopyrene and 8 kinds of polycyclic aromatic hydrocarbon in the product is far less than the environmental protection standard of European Union, and the product meets the environmental protection requirement of European Union.
EXAMPLE 2 preparation of Low viscosity aromatic-containing rubber plasticizer
Taking the normal second-line distillate oil of the intermediate base as a raw material, wherein the mass ratio of hydrogen to the normal second-line distillate oil of the intermediate base is 400:1 at the pressure of 7MPa and the temperature of 300 ℃, and the space velocity is 1.0h-1Carrying out hydrofining (refining time is 15min) under the hydrogenation condition of (2) to obtain hydrogenated oil; refining the hydrogenated oil by liquid phase denitrification (the liquid phase denitrification time is 30min), wherein the dosage of the denitrification agent is 5 per mill, and the refining temperature is 90 ℃, so as to obtain denitrified oil; and (3) refining the denitrified oil by clay adsorption, wherein the clay consumption is 5%, the refining temperature is 120 ℃, and the refining time is 30min, so that the low-viscosity rubber plasticizer containing aromatic hydrocarbon (also called low-viscosity green environment-friendly rubber plasticizer containing aromatic hydrocarbon) is obtained.
The properties of the low-viscosity green and environment-friendly rubber plasticizer containing aromatic hydrocarbons according to the present invention are shown in table 4.
Table 3 product properties of example 2 of the invention
Figure BDA0001487602240000042
Figure BDA0001487602240000051
As can be seen from Table 3, the aromatic hydrocarbon-containing low-viscosity green environment-friendly rubber plasticizer of the present invention has a viscosity of 10.23 at 40 ℃ and a relatively low viscosity; the product has the chroma of less than 0.1 and light color, and meets the requirement on color in the processing process of light-colored rubber products; the aromatic carbon rate of the product is 11.7 percent, and the requirement on a plasticizer in the rubber processing process is met; the content of benzopyrene and 8 kinds of polycyclic aromatic hydrocarbon in the product is far less than the environmental protection standard of European Union, and the product meets the environmental protection requirement of European Union and is an environmental protection product.
EXAMPLE 3 preparation of Low viscosity aromatic-containing rubber plasticizer
The naphthenic normal-third-line distillate oil is used as a raw material, the mass ratio of hydrogen to the naphthenic normal-third-line distillate oil is 400:1 at the pressure of 6.5MPa and the temperature of 320 ℃, and the volume space velocity is 0.5h-1Carrying out hydrofining (the reaction time is specifically 30min) under the hydrogenation condition of (1) to obtain hydrogenated oil; the hydrogenated oil is refined by liquid phase denitrification, the addition amount of a denitrifying agent is 6 per mill of the mass percentage content of the hydrogenated oil, and the refining temperature is 95 ℃ (the reaction time is 40min specifically), so that the denitrified oil is obtained; and (3) refining the denitrified oil by clay adsorption, wherein the clay consumption is 8 percent of the weight percentage content of the denitrified oil, the refining temperature is 140 ℃, and the refining time is 60min, so that the low-viscosity rubber plasticizer containing aromatic hydrocarbon (also called low-viscosity green environment-friendly rubber plasticizer containing aromatic hydrocarbon) is obtained.
The properties of the low-viscosity green and environment-friendly rubber plasticizer containing aromatic hydrocarbons according to the present invention are shown in table 4.
Table 4 product properties of example 3 of the invention
Figure BDA0001487602240000061
As can be seen from Table 4, the aromatic hydrocarbon-containing low-viscosity green environment-friendly rubber plasticizer of the present invention has a viscosity of 22.93 at 40 ℃ and a relatively low viscosity; the product has the chroma of less than 0.1 and light color, and meets the requirement on color in the processing process of light-colored rubber products; the aromatic carbon rate of the product is 11.1 percent, and the requirement on a plasticizer in the rubber processing process is met; the content of benzopyrene and 8 kinds of polycyclic aromatic hydrocarbon in the product is far less than the environmental protection standard of European Union, and the product meets the environmental protection requirement of European Union and is an environmental protection product.

Claims (6)

1. A preparation method of a low-viscosity rubber plasticizer containing aromatic hydrocarbon comprises the following steps: (1) carrying out hydrogenation reaction on the distillate oil to obtain hydrogenated oil;
the distillate oil is at least one of normal second-line distillate oil, normal third-line distillate oil and reduced first-line distillate oil of crude oil;
the crude oil of the distillate oil belongs to a middle group and/or a naphthenic group;
the conditions of the hydrogenation reaction are as follows: the hydrogen partial pressure is 2-15 MPa, the reaction temperature is 250-370 ℃, the reaction time is 10-60 min, and the volume space velocity is 0.5-3.0 h-1The volume ratio of the hydrogen to the distillate oil is 400-1000: 1;
the catalyst adopted in the hydrogenation reaction is at least one amorphous silica-alumina catalyst in nickel-molybdenum, nickel-tungsten, cobalt-molybdenum, molybdenum-cobalt-nickel and molybdenum-nickel-tungsten types;
(2) carrying out liquid-phase denitrification reaction on the hydrogenated oil, and removing nitrogen slag to obtain denitrified oil;
(3) and carrying out adsorption reaction on the denitrified oil to obtain the low-viscosity rubber plasticizer containing aromatic hydrocarbon.
2. The method of claim 1, wherein: the kinematic viscosity of the distillate oil at 40 ℃ is 7-40 mm2The distillation range is 250-370 ℃.
3. The production method according to claim 1 or 2, characterized in that: the mass percentage of the added denitrifier for the liquid-phase denitrification reaction is 1-8 per mill of the hydrogenated oil;
the denitrifier is a Lewis acid compound type denitrifier;
the temperature of the liquid-phase denitrification reaction is 50-100 ℃, and the reaction time is 10-60 min.
4. The production method according to claim 1 or 2, characterized in that: the adsorbent adopted in the adsorption reaction is argil;
the mass percentage of the clay added is 0.5-10% of the denitrification oil;
the temperature of the adsorption reaction is 100-160 ℃, and the time is 10-60 min.
5. The aromatic-containing low-viscosity rubber plasticizer obtained by the production method according to any one of claims 1 to 4.
6. A rubber plasticizer according to claim 5, characterized in that: the performance parameters of the low-viscosity rubber plasticizer containing aromatic hydrocarbon are as follows: the kinematic viscosity at 40 ℃ is 6-30 mm2The aromatic carbon rate is 10-15%, the aniline point is less than 80 ℃, the benzopyrene is less than 1mg/kg, and the polycyclic aromatic hydrocarbon is less than 10 mg/kg.
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CN104910959A (en) * 2015-05-18 2015-09-16 中国海洋石油总公司 Transformer oil antigassing additive and preparation method thereof
CN106047405A (en) * 2016-06-07 2016-10-26 中海沥青股份有限公司 Method for producing heat conduction oil by using naphthenic crude
CN106010638A (en) * 2016-06-21 2016-10-12 中国海洋石油总公司 Preparation method of low-viscosity green rubber plasticizer

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