Hydrogenated nitrile rubber and method for producing the same

Abstract

The application relates to the field of rubber polymerization, and discloses a hydrogenated nitrile rubber and a preparation method thereof. The preparation method comprises the following steps: (1) dissolving nitrile rubber in an organic solvent to obtain a nitrile rubber glue solution, and carrying out charging and discharging degassing; (2) adding the nitrile rubber glue solution into a jet reactor, and adding a hydrogenation catalyst and a ligand; (3) filling hydrogen, circulating mixing, and carrying out hydrogenation reaction; and (4) removing the organic solvent in the reaction product obtained in the step (3) to obtain the hydrogenated nitrile rubber; the hydrogenation catalyst has the following general formula: (R m A) z RhX n The preparation method of the hydrogenated nitrile rubber can not only reduce the cost of the hydrogenation process, but also effectively improve hydrogenation reaction activity, reaction speed, reaction time and product hydrogenation degree.

Description

TECHNICAL FIELD

[0001] The present application relates to the field of rubber polymerization, in particular, to a hydrogenated nitrile rubber and a preparation method thereof. BACKGROUND

[0002] As a high-saturation nitrile rubber, the hydrogenated nitrile rubber is currently mainly prepared by hydrogenation modification of nitrile rubber. The hydrogenated nitrile rubber has good oil resistance, low-temperature resistance (-40℃), oxidation resistance, ozone resistance and other properties, and also has very excellent mechanical properties, and is widely used in the fields of automobile manufacturing, mechanical processing, metallurgical sealing, petroleum industry and the like.

[0003] In the production of the hydrogenated nitrile rubber, the catalytic hydrogenation of the nitrile rubber is a key technology, and the production technical conditions are extremely harsh. In the traditional kettle type hydrogenation process, gas-liquid two-phase mixing is carried out by stirring, and with the increase of the hydrogenation degree, the contact probability of the carbon-carbon double bond with hydrogen and the catalyst gradually decreases, which affects the hydrogenation efficiency. At the same time, due to the reasons such as high price of the catalyst required for the production of the hydrogenated nitrile rubber, high equipment requirement, large reaction energy consumption and the like, the price of the hydrogenated nitrile rubber has been high, and the product selling price is about 200-300 yuan / ton, which seriously hinders the large-scale application in China. SUMMARY

[0004] The present application relates to the field of rubber polymerization, in particular, to a hydrogenated nitrile rubber and a preparation method thereof.

[0005] The present application relates to the field of rubber polymerization, in particular, to a hydrogenated nitrile rubber and a preparation method thereof.

[0006] In order to achieve the above-mentioned effects, the present application provides a preparation method of a hydrogenated nitrile rubber, characterized in that the preparation method comprises the following steps:

[0007] (1) dissolving the nitrile rubber in an organic solvent to obtain a nitrile rubber glue solution, and carrying out charging and discharging degassing;

[0008] (2) adding the nitrile rubber glue solution into a jet reactor, adding a hydrogenation catalyst and a ligand;

[0009] (3) filling hydrogen, circulating mixing, and carrying out hydrogenation reaction;

[0010] (4) removing the organic solvent in the reaction product obtained in step (3) to obtain the hydrogenated nitrile rubber;

[0011] The catalyst for hydrogenation has the general formula: (R m A) z RhX n ;

[0012] wherein R is independently selected from C1-C8 alkyl, C4-C8 cycloalkyl, C6-C15 aryl or C7-C15 aralkyl; A is selected from phosphorus, arsenic, sulfur or sulfoxide group; X is selected from hydrogen or anion; z is 2, 3 or 4; m is 2 or 3; n is 1, 2 or 3.

[0013] The second aspect of the present application provides a hydrogenated nitrile rubber prepared by the above preparation method.

[0014] Through the above technical solution, the hydrogenated nitrile rubber and the preparation method thereof provided by the present application have the following beneficial effects:

[0015] In the present application, compared with the traditional stirring reactor, the hydrogenation reaction of the nitrile rubber is carried out in the jet reactor, which can more efficiently mix the nitrile rubber, hydrogen and the catalyst, thereby using a catalyst with lower cost to realize the catalytic hydrogenation of the nitrile rubber, reducing the cost of the hydrogenation process, effectively improving the hydrogenation reaction activity, increasing the reaction speed, shortening the reaction time, and improving the hydrogenation degree of the hydrogenation product, and the comprehensive application cost is lower. BRIEF DESCRIPTION OF DRAWINGS

[0016] Figure 1 It is a schematic view of one specific embodiment of the present application.

[0017] REFERENCE NUMERALS

[0018] 1-jet reactor cylinder; 2-material injector; 3-nozzle; 4-gas suction chamber; 5-mixing chamber; 6-diffusion chamber; 7-gas phase space hydrogen circulation pipeline; 8-nitrile rubber glue solution / catalyst solution inlet; 9-fresh hydrogen inlet; 10-glue solution outlet; 11-circulating glue solution inlet; 12-glue solution circulating pump; 13-circulating glue solution heater. DETAILED DESCRIPTION

[0019] The endpoints of the ranges and any values disclosed herein are not limited to the precise values stated. The endpoints of the ranges and any values are provided as approximations. Any numerical value, however, can inherently contain certain errors necessarily resulting from the standard deviation found in their respective testing measurements. Also, the endpoints of the ranges and any values are only approximate, as some variations can occur. The endpoints of the ranges and any values can therefore not be exact boundaries but are at best only approximations. These and other variations, which will depend on the specific application, can or can not be included in the application as recited in the following claims.

[0020] The first aspect of the present application provides a preparation method of hydrogenated nitrile rubber, characterized in that the preparation method comprises the following steps:

[0021] (1) dissolving nitrile rubber in an organic solvent to obtain a nitrile rubber glue solution, and degassing by charging and discharging;

[0022] (2) adding the nitrile rubber glue solution into a jet reactor, adding a hydrogenation catalyst and a ligand;

[0023] (3) charging hydrogen, circulating mixing, and performing hydrogenation reaction;

[0024] (4) removing the organic solvent in the reaction product obtained in step (3) to obtain the hydrogenated nitrile rubber;

[0025] The hydrogenation catalyst has the following general formula: (R m A) z RhX n ;

[0026] wherein R is independently selected from C1-C8 alkyl, C4-C8 cycloalkyl, C6-C15 aryl or C7-C15 aralkyl; A is selected from phosphorus, arsenic, sulfur or sulfoxide group S=O; X is selected from hydrogen or anion; z is 2, 3 or 4; m is 2 or 3; n is 1, 2 or 3.

[0027] In the present application, compared with the traditional stirring reactor, the hydrogenation reaction of nitrile rubber is carried out in the jet reactor, which can more efficiently mix nitrile rubber, hydrogen and catalyst, thereby using a lower-cost catalyst to realize catalytic hydrogenation of nitrile rubber, reduce the cost of hydrogenation process, effectively improve the hydrogenation reaction activity, increase the reaction speed, shorten the reaction time, and improve the hydrogenation degree of hydrogenation products, and the comprehensive application cost is lower.

[0028] According to the present application, the jet reactor comprises a reactor cylinder 1 and a material jet 2 placed in the reactor cylinder 1.

[0029] According to the present application, the top end of the material jet 2 is connected with the upper head of the reactor cylinder 1; the bottom end of the material jet 2 extends into the material in the reactor cylinder 1.

[0030] According to the present application, the jet reactor is a batch circulation reactor.

[0031] According to the present application, along the direction from the top end to the bottom end of the material jet 2, the material jet 2 comprises a nozzle 3, an air suction chamber 4, a mixing chamber 5 and a diffusion chamber 6 in sequence.

[0032] According to the present application, the suction chamber 4 of the material injector is located above the operating liquid level; the top of the suction chamber 4 is provided with a gas phase inlet, and the side of the suction chamber 4 is provided with a gas phase outlet.

[0033] In the present application, the gas phase inlet and the gas phase outlet together realize the circulation of hydrogen.

[0034] In the present application, the suction chamber 4 is entirely located above the operating liquid level.

[0035] According to the present application, the height of the mixing chamber 5 is 40%-80% of the height of the cylinder, preferably 50%-70%.

[0036] According to the present application, 70%-100% of the height of the mixing chamber 5 is located below the operating liquid level.

[0037] Further, 85%-95% of the height of the mixing chamber 5 is located below the operating liquid level.

[0038] According to the present application, in step (1), the mass percentage concentration of the nitrile rubber in the nitrile rubber glue (i.e. the mass of the nitrile rubber divided by the sum of the mass of the nitrile rubber and the organic solvent) is not particularly limited. In order to enable the nitrile rubber in the nitrile rubber glue to fully contact and react with hydrogen, preferably, the mass percentage of the nitrile rubber in the nitrile rubber glue is 2-15%, preferably 4-12%.

[0039] In the present application, the nitrile rubber is not particularly limited, and can be various nitrile rubbers containing carbon-carbon double bonds (C=C) and cyano groups (CN).

[0040] According to the present application, in step (1), the nitrile rubber is selected from binary nitrile rubbers and / or ternary nitrile rubbers.

[0041] According to the present application, the binary nitrile rubber is selected from at least one of butadiene-acrylonitrile, butadiene-(meth)acrylonitrile, 2-methyl-1,3-butadiene-acrylonitrile, and 2-methyl-1,3-butadiene-(meth)acrylonitrile.

[0042] According to the present application, the terbucryl rubber is at least one selected from the group consisting of butadiene-acrylonitrile-acrylic acid, butadiene-acrylonitrile-methyl acrylate, butadiene-acrylonitrile-ethyl acrylate, butadiene-acrylonitrile-tert-butyl acrylate, butadiene-acrylonitrile-butyl acrylate, butadiene-acrylonitrile-(meth)acrylic acid, butadiene-acrylonitrile-(meth)acrylic acid methyl ester, butadiene-acrylonitrile-(meth)acrylic acid ethyl ester, butadiene-acrylonitrile-(meth)acrylic acid tert-butyl ester, butadiene-acrylonitrile-(meth)acrylic acid butyl ester, butadiene-(meth)acrylonitrile-acrylic acid, butadiene-(meth)acrylonitrile-acrylic acid methyl ester, butadiene-(meth)acrylonitrile-acrylic acid ethyl ester, butadiene-(meth)acrylonitrile-acrylic acid tert-butyl ester, butadiene-(meth)acrylonitrile-acrylic acid butyl ester, butadiene-(meth)acrylonitrile-(meth)acrylic acid, butadiene-(meth)acrylonitrile-(meth)acrylic acid methyl ester, butadiene-(meth)acrylonitrile-(meth)acrylic acid ethyl ester, butadiene-(meth)acrylonitrile-(meth)acrylic acid tert-butyl ester, and butadiene-(meth)acrylonitrile-(meth)acrylic acid butyl ester.

[0043] According to the present application, the butyl nitrile rubber is selected from the group consisting of butadiene-acrylonitrile and / or butadiene-(meth)acrylonitrile. In the present application, when the butyl nitrile rubber is a mixture of butadiene-acrylonitrile and butadiene-(meth)acrylonitrile, the ratio of the use amount of the two is not particularly required and can be any ratio.

[0044] In the present application, the type of the organic solvent in step (1) is not particularly limited and can be various organic solvents capable of dissolving butyl nitrile rubber in the art, and preferably, the organic solvent is at least one selected from the group consisting of aromatic hydrocarbons, alkyl- or halogen-substituted aromatic hydrocarbons, halogenated alkanes, ketones, and amides.

[0045] Further, the organic solvent is at least one selected from the group consisting of benzene, toluene, xylene, chlorobenzene, dichlorobenzene, trichlorobenzene, acetone, butanone, and N,N-dimethylformamide.

[0046] According to the present application, in order to further improve the hydrogenation degree of the hydrogenation product, preferably, R is selected from the group consisting of C6-C15 aryl and / or C7-C15 aralkyl; A is at least one selected from the group consisting of phosphorus, arsenic, and sulfur; X is selected from the group consisting of Cl and / or H; z is 3 or 4; m is 2 or 3; n is an integer of 1-3; and more preferably, the hydrogenation catalyst is (PPh3)3RhCl.

[0047] In the present application, in order to improve the hydrogenation reaction activity of the hydrogenation catalyst and increase the hydrogenation degree of the hydrogenated butyl nitrile rubber, the addition amount of the hydrogenation catalyst is 0.01-5 wt% of the dry rubber mass of the butyl nitrile rubber, and preferably, 0.01-1 wt%.

[0048] In the present application, in order to further improve the hydrogenation degree of the hydrogenation product, preferably, the mass ratio of the ligand to the hydrogenation catalyst is 1-40:1, preferably 4-15:1.

[0049] According to the present application, the ligand is selected from at least one of organic phosphine, organic diphosphine, organic cerium, nitrogen-containing organic compound, sulfur-containing organic compound and oxygen-containing organic compound, preferably organic phosphine, more preferably triphenylphosphine.

[0050] There is no particular limitation on the organic phosphine, organic diphosphine, organic cerium, nitrogen-containing organic compound, sulfur-containing organic compound and oxygen-containing organic compound in the hydrogenation catalyst and the ligand, and they can be various organic phosphines, organic diphosphines, organic ceriums, nitrogen-containing organic compounds, sulfur-containing organic compounds and oxygen-containing organic compounds commonly used in the art.

[0051] According to the present application, in step (3), the conditions of the hydrogenation reaction include that the reaction temperature is 50-180℃, the hydrogen pressure is 0.1-15 MPa, and the reaction time is 1-20 hours.

[0052] In order to further increase the hydrogenation degree of the hydrogenation product, preferably, the conditions of the hydrogenation reaction include that the reaction temperature is 80-150℃, the hydrogen pressure is 2-12 MPa, and the reaction time is 2-16 hours.

[0053] In the present application, there is no particular limitation on the method for removing the organic solvent in the reaction product obtained in step (3), and it can be various methods commonly used by those skilled in the art, for example, the organic solvent in the reaction product obtained in step (3) can be removed by ethanol condensation, water vapor distillation method, etc., so as to obtain the hydrogenation product, and then the solvent on the obtained hydrogenation product is removed. There is no particular limitation on the method for removing the solvent on the hydrogenation product, and it can be various methods commonly used by those skilled in the art, and preferably, the method for removing the solvent is vacuum drying, and the conditions of the vacuum drying include that the temperature is 50-100℃, and the time is 1-10 hours.

[0054] As shown in Figure 1 In one specific embodiment of the present application, the jet reactor includes a reactor cylinder 1 and a material jet 2, the top end of the material jet 2 is connected with the upper head of the reactor, and the bottom end of the material jet 2 extends into the material in the reactor. Along the direction from the top end to the bottom end of the material jet 2, the material jet 2 includes a nozzle 3, an air suction chamber 4, a mixing chamber 5 and a diffusion chamber 6 in sequence.

[0055] The air suction chamber is located above the operating liquid level, the top of the air suction chamber is provided with a gas phase inlet, and the side of the air suction chamber is provided with a gas phase outlet.

[0056] The height of the mixing chamber 5 is 40%-80% of the height of the reactor cylinder 1. 70%-100% of the mixing chamber is below the operating liquid level based on the height of the mixing chamber 5.

[0057] The nitrile rubber is dissolved in the organic solvent to obtain a nitrile rubber glue solution; the nitrile rubber glue solution, the hydrogenation catalyst solution, and the ligand solution enter the jet reactor through the nitrile rubber glue / catalyst solution inlet 8, are mixed with hydrogen gas entering the jet reactor through the fresh hydrogen gas inlet 9, and are subjected to hydrogenation reaction, and the reaction product is discharged from the glue solution outlet 10 of the jet reactor.

[0058] The reaction product is partially discharged from the reaction system through the glue solution circulating pump 12, and the remaining part is transported to the circulating glue solution heater 13 for heating treatment, and the heated circulating glue solution enters the jet reactor through the circulating glue solution inlet 11.

[0059] The second aspect of the present application provides hydrogenated nitrile rubber prepared by the above preparation method.

[0060] The present application will be described in detail below through examples.

[0061] In the following examples and comparative examples, the hydrogenation degree of the hydrogenated nitrile rubber is measured by nuclear magnetic resonance spectroscopy.

[0062] The butadiene-acrylonitrile rubber is purchased from Lan Chemical Co., Ltd., and the brand is N21L, and the cyano content is 41% by mass.

[0063] Example 1

[0064] Example 1 of the present application is used to illustrate the preparation method of the hydrogenated nitrile rubber of the present application:

[0065] (1) The nitrile is dissolved in an organic solvent to obtain a nitrile rubber glue solution, which is added to a reaction kettle and degassed;

[0066] (2) The nitrile glue solution is added to a jet reactor, and a hydrogenation catalyst and a ligand are added;

[0067] (3) Hydrogen is filled, and the mixture is circulated to perform hydrogenation reaction, and the hydrogenation reaction conditions include: the reaction temperature is b℃, the hydrogen pressure is a MPa, and the reaction time is c hours;

[0068] (4) The hydrogenation product is precipitated by ethanol condensation and is vacuum dried at 60℃ for 8 hours;

[0069] wherein the hydrogenation catalyst is (PPh3)3RhCl, i.e., X is Cl, n=1, z=3, R is phenyl, m=3, and A is P;

[0070] In the jet reactor, the suction chamber 4 is located below the operating liquid level; the height of the mixing chamber 5 is 60% of the height of the reactor cylinder 1; and 90% of the height of the mixing chamber 5 is located below the operating liquid level.

[0071] The concentration of the nitrile rubber glue solution (i.e., the mass percentage concentration of nitrile rubber in the glue solution), the amount of hydrogenation catalyst (i.e., the mass percentage of the hydrogenation catalyst relative to the nitrile rubber), the ligand / catalyst (i.e., the mass ratio of the ligand to the hydrogenation catalyst), and the hydrogenation reaction conditions are shown in Table 1.

[0072] Examples 2-10

[0073] The preparation method is basically the same as that of Example 1, except that the concentration of the nitrile rubber glue solution (i.e., the mass percentage concentration of nitrile rubber in the glue solution), the amount of hydrogenation catalyst (i.e., the mass percentage of the hydrogenation catalyst relative to the nitrile rubber), the ligand / catalyst (i.e., the mass ratio of the ligand to the hydrogenation catalyst), and the hydrogenation reaction conditions are different from those of Example 1, as shown in Table 1.

[0074] Example 11

[0075] The preparation method is basically the same as that of Example 1, except that in the jet reactor, the suction chamber 4 is located below the operating liquid level; the height of the mixing chamber 5 is 80% of the height of the reactor cylinder 1; and 100% of the height of the mixing chamber 5 is located below the operating liquid level.

[0076] Example 12

[0077] The preparation method is basically the same as that of Example 1, except that in the jet reactor, the suction chamber 4 is located above the operating liquid level; the height of the mixing chamber 5 is 30% of the height of the reactor cylinder 1; and 40% of the height of the mixing chamber 5 is located below the operating liquid level.

[0078] Comparative Examples 1-3

[0079] The preparation method is basically the same as that of Examples 1-7, except that the jet reactor is replaced by a commonly used stirring reactor, which is composed of a stirring shaft and a stirring paddle.

[0080] Table 1

[0081]

[0082]

[0083] As can be seen from Examples 1-12 and Comparative Examples 1-3, carrying out the hydrogenation reaction of the butyl nitrile rubber in the jet reactor can effectively improve the hydrogenation reaction activity, increase the reaction speed, shorten the reaction time, and increase the hydrogenation degree of the hydrogenation product.

[0084] Further, when the suction chamber and the mixing chamber of the material jet in the jet reactor meet the scope of the present application, the hydrogenation reaction activity can be further improved, the reaction speed can be increased, the reaction time can be shortened, and the hydrogenation degree of the hydrogenation product can be increased.

[0085] Further, when the amount of the hydrogenation catalyst and the conditions of the hydrogenation reaction meet the scope of the present application, the hydrogenation reaction activity can be further improved, the reaction speed can be increased, the reaction time can be shortened, and the hydrogenation degree of the hydrogenation product can be increased.

[0086] The preferred embodiments of the present application are described in detail above, but the present application is not limited thereto. Within the technical concept scope of the present application, various simple modifications can be made to the technical solutions of the present application, including the combination of various technical features in any other suitable manner, and these simple modifications and combinations should also be considered as disclosed by the present application and fall within the protection scope of the present application.

Claims

1. A process for the preparation of hydrogenated nitrile rubber, characterized in that, The preparation method comprises the following steps: (1) dissolving nitrile rubber in an organic solvent to obtain a nitrile rubber glue solution, and degassing by charging and discharging; (2) adding the nitrile rubber glue solution into a jet reactor, adding a hydrogenation catalyst and a ligand; (3) filling hydrogen, circulating mixing, and performing hydrogenation reaction; (4) removing the organic solvent in the reaction product obtained in step (3) to obtain the hydrogenated nitrile rubber; The hydrogenation catalyst has the general formula: (R m A) z RhX n ; wherein R is independently selected from C1-C8 alkyl, C4-C8 cycloalkyl, C6-C15 aryl or C7-C15 aralkyl; A is selected from phosphorus, arsenic, sulfur or sulfoxide group; X is selected from hydrogen or anion; z is an integer of 2-4; m is 2 or 3; n is an integer of 1-3; wherein in step (2), the jet reactor comprises a reactor cylinder (1) and a material jet (2) arranged in the reactor cylinder (1); wherein along the direction from the top end to the bottom end of the material jet (2), the material jet (2) comprises a nozzle (3), an air suction chamber (4), a mixing chamber (5) and a diffusion chamber (6) in sequence; wherein the top of the air suction chamber (4) is provided with a gas phase inlet, and the side of the air suction chamber (4) is provided with a gas phase outlet; wherein the height of the mixing chamber (5) is 40%-80% of the height of the reactor cylinder (1); wherein 70%-100% of the mixing chamber (5) is below the operating liquid level based on the height of the mixing chamber (5); wherein in step (3), the conditions of the hydrogenation reaction include: the reaction temperature is 50-180℃, the hydrogen pressure is 0.1-15MPa, and the reaction time is 1-20 hours.

2. The production method according to claim 1, wherein The top end of the material jet (2) is connected with the upper head of the reactor cylinder (1), and the bottom end of the material jet (2) extends into the material in the reactor cylinder (1).

3. The production method according to claim 1, wherein The jet reactor is a batch circulation reactor.

4. The production method according to claim 1, wherein The air suction chamber (4) of the material jet (2) is above the operating liquid level.

5. The production method according to claim 1, wherein The height of the mixing chamber (5) is 50%-70% of the height of the reactor cylinder (1).

6. The production method according to claim 1, wherein 85%-95% of the mixing chamber (5) is below the operating liquid level based on the height of the mixing chamber (5).

7. The production process according to any one of claims 1 to 6, wherein In step (1), the mass percentage concentration of nitrile rubber in the nitrile rubber glue solution is 2-15%.

8. The production process according to any one of claims 1 to 6, wherein In step (1), the nitrile rubber is selected from binary nitrile rubber and / or ternary nitrile rubber.

9. The method of claim 8, wherein, The binary nitrile rubber is selected from butadiene-(meth)acrylonitrile and / or 2-methyl-1,3-butadiene-(meth)acrylonitrile.

10. The method of claim 8, wherein, The ternary nitrile rubber is selected from at least one of butadiene-(meth)acrylonitrile-(meth)acrylic acid, butadiene-(meth)acrylonitrile-(meth)acrylic acid methyl ester, butadiene-(meth)acrylonitrile-(meth)acrylic acid ethyl ester, butadiene-(meth)acrylonitrile-(meth)acrylic acid tert-butyl ester and butadiene-(meth)acrylonitrile-(meth)acrylic acid butyl ester.

11. The method of claim 9, wherein, The binary nitrile rubber is selected from butadiene-(meth)acrylonitrile.

12. The method of making according to any one of claims 1-6, wherein, In step (1), the organic solvent is selected from at least one of aromatic hydrocarbon, halogenated alkane, ketone and amide.

13. The method of claim 12, wherein, The organic solvent is selected from at least one of benzene, toluene, xylene, chlorobenzene, dichlorobenzene, trichlorobenzene, acetone, butanone and N,N-dimethylformamide.

14. The method of making according to any one of claims 1-6, wherein, R is selected from C6-C15 aryl and / or C7-C15 aralkyl; A is selected from at least one of phosphorus, arsenic and sulfur; X is selected from Cl and / or H; z is 3 or 4; m is 2 or 3; n is an integer of 1-3.

15. The method of making according to any one of claims 1-6, wherein, The hydrogenation catalyst is (PPh3)3RhCl.

16. The method of making according to any one of claims 1-6, wherein, In step (2), the hydrogenation catalyst is added in an amount of 0.01-5 wt% of the mass of the dry nitrile rubber.

17. The method of making according to claim 16, wherein, In step (2), the hydrogenation catalyst is added in an amount of 0.01-1 wt% of the mass of the dry nitrile rubber.

18. The method of making according to any one of claims 1-6, wherein, The ligand is selected from at least one of an organic phosphine, an organic cerium, a nitrogen-containing organic compound, a sulfur-containing organic compound and an oxygen-containing organic compound.

19. The method of making according to claim 18, wherein, The ligand is an organic phosphine.

20. The method of making according to claim 19, wherein, The ligand is triphenylphosphine.

21. The method of making according to any one of claims 1-6, wherein, The mass ratio of the ligand to the hydrogenation catalyst is 1-40:

1.

22. The method of making according to claim 21, wherein, The mass ratio of the ligand to the hydrogenation catalyst is 4-15:

1.

23. The method of making according to any one of claims 1-6, wherein, The conditions of the hydrogenation reaction include a reaction temperature of 80-150°C, a hydrogen pressure of 2-12 MPa and a reaction time of 2-16 hours.

24. Hydrogenated nitrile rubber prepared by the preparation method of any one of claims 1-23.

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