CN103739516B - A kind of method utilizing the isomerization liquid Adiponitrile of 2-methyl-3-crotononitrile - Google Patents
A kind of method utilizing the isomerization liquid Adiponitrile of 2-methyl-3-crotononitrile Download PDFInfo
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- CN103739516B CN103739516B CN201410004491.7A CN201410004491A CN103739516B CN 103739516 B CN103739516 B CN 103739516B CN 201410004491 A CN201410004491 A CN 201410004491A CN 103739516 B CN103739516 B CN 103739516B
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- isomerization
- crotononitrile
- methyl
- adiponitrile
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- 238000006317 isomerization reaction Methods 0.000 title claims abstract description 47
- 239000007788 liquid Substances 0.000 title claims abstract description 37
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 40
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims abstract description 29
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 24
- UVKXJAUUKPDDNW-NSCUHMNNSA-N (e)-pent-3-enenitrile Chemical compound C\C=C\CC#N UVKXJAUUKPDDNW-NSCUHMNNSA-N 0.000 claims abstract description 16
- CFEYBLWMNFZOPB-UHFFFAOYSA-N Allylacetonitrile Natural products C=CCCC#N CFEYBLWMNFZOPB-UHFFFAOYSA-N 0.000 claims abstract description 16
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003446 ligand Substances 0.000 claims abstract description 12
- 239000011574 phosphorus Substances 0.000 claims abstract description 11
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 11
- 230000002378 acidificating effect Effects 0.000 claims abstract description 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 16
- 238000009413 insulation Methods 0.000 claims description 10
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- FDLFMPKQBNPIER-UHFFFAOYSA-N 1-methyl-3-(3-methylphenoxy)benzene Chemical compound CC1=CC=CC(OC=2C=C(C)C=CC=2)=C1 FDLFMPKQBNPIER-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 claims description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 2
- FEVFLQDDNUQKRY-UHFFFAOYSA-N tris(4-methylphenyl) phosphite Chemical compound C1=CC(C)=CC=C1OP(OC=1C=CC(C)=CC=1)OC1=CC=C(C)C=C1 FEVFLQDDNUQKRY-UHFFFAOYSA-N 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims description 2
- 229960001763 zinc sulfate Drugs 0.000 claims description 2
- 229910000368 zinc sulfate Inorganic materials 0.000 claims description 2
- 238000005669 hydrocyanation reaction Methods 0.000 abstract description 9
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 231100000572 poisoning Toxicity 0.000 abstract description 4
- 230000000607 poisoning effect Effects 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 3
- ISBHMJZRKAFTGE-UHFFFAOYSA-N pent-2-enenitrile Chemical compound CCC=CC#N ISBHMJZRKAFTGE-UHFFFAOYSA-N 0.000 description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 208000012839 conversion disease Diseases 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 238000005204 segregation Methods 0.000 description 2
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000019605 sweet taste sensations Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of method utilizing the isomerization liquid Adiponitrile of 2-methyl-3-crotononitrile, comprise the following steps: 1) isomerization reaction 2-methyl-3-crotononitrile is occurred under zero-valent nickel catalyst, phosphorus-containing ligand and lewis acidic effect and generates 3 pentene nitrile; 2) isomerization liquid step 1) obtained and prussic acid hybrid reaction, generate the product comprising adiponitrile.Isomerization reaction is there is and generates 3 pentene nitrile by the present invention in 2-methyl-3-crotononitrile under zero-valent nickel catalyst, phosphorus-containing ligand and lewis acidic effect, analyze the composition of isomerization liquid, itself and secondary hydrocyanation reaction material proportion are substantially suitable, therefore the present invention directly adopts isomerization liquid and prussic acid Reactive Synthesis adiponitrile.Therefore, present invention omits the operation of isomerization liquid separating-purifying 3 pentene nitrile, greatly reduce equipment cost and production cost, and decrease the poisoning of zero-valent nickel catalyst and phosphorus-containing ligand.
Description
Technical field
The present invention relates to the production technical field of adiponitrile, relate to a kind of method utilizing the isomerization liquid Adiponitrile of 2-methyl-3-crotononitrile.
Background technology
Adiponitrile molecular formula is CN(CH
2)
4cN, English is abbreviated as ADN, and be one of main raw material producing type material nylon66 fiber, its proterties is colourless oil liquid, is slightly with sweet taste, toxic and corrodibility, and density is 962g/cm
2, fusing point 1 DEG C, boiling point 295 DEG C (1atm).In addition, it also has wide application in electronics, light industry and other organic synthesis field.
Butadiene process Adiponitrile mainly divides hydrocyanation, isomerization, secondary hydrocyanation three steps, and the reaction equation of these three steps is as follows:
First under the effect of zero-valent nickel catalyst, phosphorus part, divinyl and prussic acid hydrocyanation reaction are synthesized 3 pentene nitrile (3PN), this reaction produces by product 2-methyl-3-crotononitrile (2M3BN); Wherein the selectivity of 3PN is the selectivity of 75%, 2M3BN is 25%.Therefore, for improving the reaction yield of 3PN, need by 2M3BN isomerization synthesis 3PN.Existing technique is after isomerization terminates, and rectification under vacuum separating isomerism liquid obtains high purity 3PN and carries out secondary hydrocyanation reaction Adiponitrile.
Such as: publication number be CN103180290A patent document discloses a kind of method for the preparation of nitrile, the isomerization liquid 222 wherein isomerization reaction obtained sends into segregation section 225, segregation section 225 comprises multiple water distilling apparatus, pass through multistage distillation, isolate catalyst-rich afflux 240,2M3BN rich stream 967 and 3PN rich stream 300, then pipeline 300 is introduced into the 3rd reaction zone (Z
3) in, at this 3PN and HCN Reactive Synthesis adiponitrile (see 0107th ~ 0113 section, its specification sheets).
But isomerization liquid separating-purifying 3PN adds technical process and process complexity, adds equipment cost and production cost, in rectification under vacuum process, in isomerization liquid, nickel catalyzator and organophosphor ligand are poisoning because of continuous high temperature, and 3PN and 2M3BN boiling point is close, separation difficulty.
Summary of the invention
In view of this, the object of the present invention is to provide a kind of method utilizing the isomerization liquid Adiponitrile of 2-methyl-3-crotononitrile, simplification of flowsheet, reduce nickel catalyzator poisoning, reduce equipment cost and production cost.
For achieving the above object, the invention provides following technical scheme:
The method utilizing the isomerization liquid Adiponitrile of 2-methyl-3-crotononitrile of the present invention, comprises the following steps:
1) 2-methyl-3-crotononitrile be there is under zero-valent nickel catalyst, phosphorus-containing ligand and lewis acidic effect isomerization reaction and generate 3 pentene nitrile;
2) isomerization liquid step 1) obtained and prussic acid hybrid reaction, generate the product comprising adiponitrile.
Further, in described step 1), the mol ratio of 2-methyl-3-crotononitrile and zero-valent nickel catalyst is 30 ~ 100:1, and the mol ratio of phosphorus-containing ligand and zero-valent nickel catalyst is 5 ~ 15:1, and the mol ratio of Lewis acid and zero-valent nickel catalyst is 1 ~ 50:1.
Further, in described step 1), reaction pressure is 0.1 ~ 0.2Mpa, and temperature of reaction is 80 ~ 120 DEG C, insulation reaction 6 ~ 12 hours.
Further, described Lewis acid is zinc chloride, aluminum chloride, zinc sulfate, iron protochloride, iron(ic) chloride or tin tetrachloride.
Further, described phosphorus-containing ligand is triphenyl phosphite, tricresyl phosphite o-toluene ester, tricresyl phosphite m-tolyl ester or tri-p-cresyl phosphite.
Further, described step 2) in, in prussic acid and isomerization liquid, the mol ratio of 3 pentene nitrile is 1:1 ~ 5.
Further, described step 2) in, reaction pressure is 0.2 ~ 0.5Mpa, and temperature of reaction is 50 ~ 100 DEG C, insulation reaction 3 ~ 5 hours.
Beneficial effect of the present invention is:
Isomerization reaction is there is and generates 3 pentene nitrile by the present invention in 2-methyl-3-crotononitrile under zero-valent nickel catalyst, phosphorus-containing ligand and lewis acidic effect, analyze the composition of isomerization liquid, itself and secondary hydrocyanation reaction material proportion are substantially suitable, therefore the present invention directly adopts isomerization liquid and prussic acid Reactive Synthesis adiponitrile.Therefore, present invention omits the operation of isomerization liquid separating-purifying 3 pentene nitrile, greatly reduce equipment cost and production cost, and decrease the poisoning of zero-valent nickel catalyst and phosphorus-containing ligand.
Embodiment
In order to make object of the present invention, technical scheme and beneficial effect clearly, will be described in detail the preferred embodiments of the present invention below.
embodiment 1
1) 2-methyl-3-crotononitrile, tricresyl phosphite o-toluene ester, zero-valent nickel catalyst and aluminum chloride are added in isomerization reactor with the mol ratio of 50:10:1:1, control reaction pressure is 0.1Mpa, temperature of reaction is 100 DEG C, and insulation reaction 8 hours, obtains isomerization liquid; The mol ratio analyzing 3 pentene nitrile, 2-methyl-3-crotononitrile, tricresyl phosphite o-toluene ester, zero-valent nickel catalyst and aluminum chloride in isomerization liquid is 48:2:10:1:1;
2) isomerization liquid step 1) obtained, prussic acid add in secondary hydrocyanation reaction still, in prussic acid and isomerization liquid, the mol ratio of 3 pentene nitrile is 1:1, control reaction pressure is 0.3Mpa, temperature of reaction is 80 DEG C, insulation reaction 4 hours, reaction terminates rear rectification under vacuum and obtains the adiponitrile product that content is greater than 99%, reaction conversion ratio 70%, selectivity 82%.
embodiment 2
1) 2-methyl-3-crotononitrile, tricresyl phosphite o-toluene ester, zero-valent nickel catalyst and aluminum chloride are added in isomerization reactor with the mol ratio of 100:15:1:5, control reaction pressure is 0.1Mpa, temperature of reaction is 100 DEG C, and insulation reaction 8 hours, obtains isomerization liquid; The mol ratio analyzing 3 pentene nitrile, 2-methyl-3-crotononitrile, tricresyl phosphite o-toluene ester, zero-valent nickel catalyst and aluminum chloride in isomerization liquid is 95:5:15:1:5;
2) isomerization liquid step 1) obtained, prussic acid add in secondary hydrocyanation reaction still, in prussic acid and isomerization liquid, the mol ratio of 3 pentene nitrile is 1:3, control reaction pressure is 0.3Mpa, temperature of reaction is 80 DEG C, insulation reaction 4 hours, reaction terminates rear rectification under vacuum and obtains the adiponitrile product that content is greater than 99%, reaction conversion ratio 75%, selectivity 80%.
embodiment 3
1) 2-methyl-3-crotononitrile, tricresyl phosphite o-toluene ester, zero-valent nickel catalyst and aluminum chloride are added in isomerization reactor with the mol ratio of 80:10:1:2, control reaction pressure is 0.1Mpa, temperature of reaction is 100 DEG C, and insulation reaction 8 hours, obtains isomerization liquid; The mol ratio analyzing 3 pentene nitrile, 2-methyl-3-crotononitrile, tricresyl phosphite o-toluene ester, zero-valent nickel catalyst and aluminum chloride in isomerization liquid is 76:4:10:1:2;
2) isomerization liquid step 1) obtained, prussic acid add in secondary hydrocyanation reaction still, in prussic acid and isomerization liquid, the mol ratio of 3 pentene nitrile is 1:5, control reaction pressure is 0.3Mpa, temperature of reaction is 80 DEG C, insulation reaction 4 hours, reaction terminates rear rectification under vacuum and obtains the adiponitrile product that content is greater than 99%, reaction conversion ratio 77%, selectivity 78%.
What finally illustrate is, above preferred embodiment is only in order to illustrate technical scheme of the present invention and unrestricted, although by above preferred embodiment to invention has been detailed description, but those skilled in the art are to be understood that, various change can be made to it in the form and details, and not depart from claims of the present invention limited range.
Claims (3)
1. utilize a method for the isomerization liquid Adiponitrile of 2-methyl-3-crotononitrile, it is characterized in that: comprise the following steps:
1) 2-methyl-3-crotononitrile be there is under zero-valent nickel catalyst, phosphorus-containing ligand and lewis acidic effect isomerization reaction and generate 3 pentene nitrile;
2) isomerization liquid step 1) obtained and prussic acid hybrid reaction, generate the product comprising adiponitrile;
In described step 1), the mol ratio of 2-methyl-3-crotononitrile and zero-valent nickel catalyst is 50 ~ 100:1, and the mol ratio of phosphorus-containing ligand and zero-valent nickel catalyst is 10 ~ 15:1, and the mol ratio of Lewis acid and zero-valent nickel catalyst is 1 ~ 5:1; Described step 2) in, in prussic acid and isomerization liquid, the mol ratio of 3 pentene nitrile is 1:1 ~ 5;
Described Lewis acid is zinc chloride, aluminum chloride, zinc sulfate, iron protochloride, iron(ic) chloride or tin tetrachloride; Described phosphorus-containing ligand is triphenyl phosphite, tricresyl phosphite o-toluene ester, tricresyl phosphite m-tolyl ester or tri-p-cresyl phosphite.
2. the method utilizing the isomerization liquid Adiponitrile of 2-methyl-3-crotononitrile according to claim 1, it is characterized in that: in described step 1), reaction pressure is 0.1 ~ 0.2Mpa, and temperature of reaction is 80 ~ 120 DEG C, insulation reaction 6 ~ 12 hours.
3. the method utilizing the isomerization liquid Adiponitrile of 2-methyl-3-crotononitrile according to claim 1, is characterized in that: described step 2) in, reaction pressure is 0.2 ~ 0.5Mpa, and temperature of reaction is 50 ~ 100 DEG C, insulation reaction 3 ~ 5 hours.
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| CN109265367B (en) * | 2018-10-30 | 2021-09-24 | 河南中平紫光科技有限公司 | Method for stabilizing catalytic system and synthesizing adiponitrile |
| CN109304192A (en) * | 2018-10-30 | 2019-02-05 | 重庆中平紫光科技发展有限公司 | A method of utilizing the immobilized lewis acid Adiponitrile of montmorillonite |
| CN109721508B (en) * | 2018-12-24 | 2022-10-04 | 安徽省安庆市曙光化工股份有限公司 | Method for preparing 3-pentenenitrile |
| CN113444018B (en) * | 2021-06-25 | 2023-09-08 | 上海东庚化工技术有限公司 | Adiponitrile production method |
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| WO1995014659A1 (en) * | 1993-11-23 | 1995-06-01 | E.I. Du Pont De Nemours And Company | Processes and catalyst compositions for hydrocyanation of monoolefins |
| CN1108643A (en) * | 1993-11-03 | 1995-09-20 | 罗纳·布朗克化学公司 | Method for hydrocyanation of unsatured nitrile into dinitrile |
| CN1535179A (en) * | 2001-07-27 | 2004-10-06 | �����ɷ� | Latalyst system containing Ni(O) for hydrocyanation |
| CN101985431A (en) * | 2010-09-30 | 2011-03-16 | 南开大学 | Method for preparing adiponitrile |
| CN103080074A (en) * | 2010-07-07 | 2013-05-01 | 因温斯特技术公司 | Process for making nitriles |
| CN103396340A (en) * | 2013-08-16 | 2013-11-20 | 山东海力化工股份有限公司 | 2-methyl-3-butenenitrile isomerization method |
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2014
- 2014-01-06 CN CN201410004491.7A patent/CN103739516B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1108643A (en) * | 1993-11-03 | 1995-09-20 | 罗纳·布朗克化学公司 | Method for hydrocyanation of unsatured nitrile into dinitrile |
| WO1995014659A1 (en) * | 1993-11-23 | 1995-06-01 | E.I. Du Pont De Nemours And Company | Processes and catalyst compositions for hydrocyanation of monoolefins |
| CN1535179A (en) * | 2001-07-27 | 2004-10-06 | �����ɷ� | Latalyst system containing Ni(O) for hydrocyanation |
| CN103080074A (en) * | 2010-07-07 | 2013-05-01 | 因温斯特技术公司 | Process for making nitriles |
| CN101985431A (en) * | 2010-09-30 | 2011-03-16 | 南开大学 | Method for preparing adiponitrile |
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