CN105130845A - 丁二烯法合成己二腈中抑制零价镍降解的方法 - Google Patents
丁二烯法合成己二腈中抑制零价镍降解的方法 Download PDFInfo
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- CN105130845A CN105130845A CN201510425699.0A CN201510425699A CN105130845A CN 105130845 A CN105130845 A CN 105130845A CN 201510425699 A CN201510425699 A CN 201510425699A CN 105130845 A CN105130845 A CN 105130845A
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- Prior art keywords
- zero
- valent nickel
- reaction
- hydrocyanation
- degraded
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 title claims abstract description 152
- 229910052759 nickel Inorganic materials 0.000 title claims abstract description 76
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims abstract description 66
- 238000000034 method Methods 0.000 title claims abstract description 47
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 230000015556 catabolic process Effects 0.000 title abstract description 5
- 238000006731 degradation reaction Methods 0.000 title abstract description 5
- 238000003786 synthesis reaction Methods 0.000 title abstract description 4
- 230000015572 biosynthetic process Effects 0.000 title abstract 3
- 230000002401 inhibitory effect Effects 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 49
- 238000005669 hydrocyanation reaction Methods 0.000 claims abstract description 43
- 238000006317 isomerization reaction Methods 0.000 claims abstract description 22
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 13
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 47
- UVKXJAUUKPDDNW-NSCUHMNNSA-N (e)-pent-3-enenitrile Chemical compound C\C=C\CC#N UVKXJAUUKPDDNW-NSCUHMNNSA-N 0.000 claims description 21
- CFEYBLWMNFZOPB-UHFFFAOYSA-N Allylacetonitrile Natural products C=CCCC#N CFEYBLWMNFZOPB-UHFFFAOYSA-N 0.000 claims description 21
- 239000003446 ligand Substances 0.000 claims description 18
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 16
- 239000002841 Lewis acid Substances 0.000 claims description 12
- 150000007517 lewis acids Chemical class 0.000 claims description 12
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 12
- 239000000376 reactant Substances 0.000 claims description 12
- 230000002829 reductive effect Effects 0.000 claims description 12
- 238000004821 distillation Methods 0.000 claims description 10
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
- 239000012752 auxiliary agent Substances 0.000 claims description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 8
- 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 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000012279 sodium borohydride Substances 0.000 claims description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
- 239000012312 sodium hydride Substances 0.000 claims description 4
- 229910000104 sodium hydride Inorganic materials 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
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims description 4
- 235000005074 zinc chloride Nutrition 0.000 claims description 4
- 239000011592 zinc chloride Substances 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 2
- 239000004411 aluminium Substances 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 229960003280 cupric chloride Drugs 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
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 235000011150 stannous chloride Nutrition 0.000 claims description 2
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 229940102001 zinc bromide Drugs 0.000 claims description 2
- 208000012839 conversion disease Diseases 0.000 abstract description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 238000001514 detection method Methods 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 238000010907 mechanical stirring Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000010792 warming Methods 0.000 description 6
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- 238000010025 steaming Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 230000003245 working effect Effects 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- ISBHMJZRKAFTGE-UHFFFAOYSA-N pent-2-enenitrile Chemical compound CCC=CC#N ISBHMJZRKAFTGE-UHFFFAOYSA-N 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (10)
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CN201510425699.0A CN105130845B (zh) | 2015-07-20 | 2015-07-20 | 丁二烯法合成己二腈中抑制零价镍降解的方法 |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106397476A (zh) * | 2016-08-31 | 2017-02-15 | 重庆中平紫光科技发展有限公司 | 利用混酚制备有机磷配体并进一步制备己二腈的方法 |
CN108997166A (zh) * | 2018-09-05 | 2018-12-14 | 中国天辰工程有限公司 | 一种用于己二腈生产中催化剂回收的设备及方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1875027A (zh) * | 2003-10-30 | 2006-12-06 | 巴斯福股份公司 | 共沸干燥的卤化镍(ii)的用途 |
CN103664691A (zh) * | 2013-12-27 | 2014-03-26 | 安徽省安庆市曙光化工股份有限公司 | 制备己二腈的方法 |
-
2015
- 2015-07-20 CN CN201510425699.0A patent/CN105130845B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1875027A (zh) * | 2003-10-30 | 2006-12-06 | 巴斯福股份公司 | 共沸干燥的卤化镍(ii)的用途 |
CN103664691A (zh) * | 2013-12-27 | 2014-03-26 | 安徽省安庆市曙光化工股份有限公司 | 制备己二腈的方法 |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106397476A (zh) * | 2016-08-31 | 2017-02-15 | 重庆中平紫光科技发展有限公司 | 利用混酚制备有机磷配体并进一步制备己二腈的方法 |
CN108997166A (zh) * | 2018-09-05 | 2018-12-14 | 中国天辰工程有限公司 | 一种用于己二腈生产中催化剂回收的设备及方法 |
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Address after: 401220 Chongqing City, Changshou economic and Technological Development Zone, No. 1 North Road Patentee after: CHONGQING ZHONGPING ZIGUANG SCIENCE & TECHNOLOGY CO., LTD. Address before: 408200 Zhenjiang fine chemical industry park, Fengdu County, Chongqing Patentee before: CHONGQING ZHONGPING ZIGUANG SCIENCE & TECHNOLOGY CO., LTD. |
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Denomination of invention: Inhibition of zero valent nickel degradation in adiponitrile synthesis by butadiene method Effective date of registration: 20200904 Granted publication date: 20170510 Pledgee: Chongqing chemical medicine holding (Group) Co., Ltd Pledgor: CHONGQING ZHONGPING ZIGUANG SCIENCE & TECHNOLOGY Co.,Ltd. Registration number: Y2020500000013 |
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Address after: 467099 room 216, second floor, East distribution building, No. 63, middle section of Jianshe Road, Pingdingshan City, Henan Province (Shenma Industrial Co., Ltd.) Patentee after: Henan Zhongping Ziguang Technology Co.,Ltd. Address before: 401220 No. 1, Huabei 1st Road, Changshou economic and Technological Development Zone, Chongqing Patentee before: CHONGQING ZHONGPING ZIGUANG SCIENCE & TECHNOLOGY Co.,Ltd. |
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Date of cancellation: 20210809 Granted publication date: 20170510 Pledgee: Chongqing chemical medicine holding (Group) Co., Ltd Pledgor: CHONGQING ZHONGPING ZIGUANG SCIENCE & TECHNOLOGY Co.,Ltd. Registration number: Y2020500000013 |
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Effective date of registration: 20220322 Address after: 467000 room 416, management committee of nylon new material industry cluster, Gongdian Town, Ye County, Pingdingshan City, Henan Province Patentee after: Henan Shenma Aidian Chemical Co.,Ltd. Address before: 467099 room 216, second floor, East distribution building, No. 63, middle section of Jianshe Road, Pingdingshan City, Henan Province (Shenma Industrial Co., Ltd.) Patentee before: Henan Zhongping Ziguang Technology Co.,Ltd. |