CA1217207A - Separation of alkenes from alkadienes - Google Patents
Separation of alkenes from alkadienesInfo
- Publication number
- CA1217207A CA1217207A CA000450265A CA450265A CA1217207A CA 1217207 A CA1217207 A CA 1217207A CA 000450265 A CA000450265 A CA 000450265A CA 450265 A CA450265 A CA 450265A CA 1217207 A CA1217207 A CA 1217207A
- Authority
- CA
- Canada
- Prior art keywords
- alkenes
- alkadienes
- range
- carbon atoms
- catalyst
- 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.)
- Expired
Links
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 25
- 150000001993 dienes Chemical class 0.000 title claims abstract description 24
- 238000000926 separation method Methods 0.000 title abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 15
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 17
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 12
- 238000005669 hydrocyanation reaction Methods 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 239000003446 ligand Substances 0.000 claims description 6
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 abstract description 10
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 abstract description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 abstract description 3
- -1 butene Chemical class 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 5
- CFEYBLWMNFZOPB-UHFFFAOYSA-N Allylacetonitrile Natural products C=CCCC#N CFEYBLWMNFZOPB-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 150000005673 monoalkenes Chemical class 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- UVKXJAUUKPDDNW-NSCUHMNNSA-N (e)-pent-3-enenitrile Chemical compound C\C=C\CC#N UVKXJAUUKPDDNW-NSCUHMNNSA-N 0.000 description 2
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000007701 flash-distillation Methods 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- QTYUSOHYEPOHLV-FNORWQNLSA-N 1,3-Octadiene Chemical compound CCCC\C=C\C=C QTYUSOHYEPOHLV-FNORWQNLSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001345 alkine derivatives Chemical group 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- ISBHMJZRKAFTGE-UHFFFAOYSA-N pent-2-enenitrile Chemical compound CCC=CC#N ISBHMJZRKAFTGE-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/17—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with acids or sulfur oxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
- C07C253/34—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/478,997 US4434316A (en) | 1983-03-25 | 1983-03-25 | Separation of alkenes from alkadienes |
| US478,997 | 1983-03-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1217207A true CA1217207A (en) | 1987-01-27 |
Family
ID=23902235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000450265A Expired CA1217207A (en) | 1983-03-25 | 1984-03-22 | Separation of alkenes from alkadienes |
Country Status (6)
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4558168A (en) * | 1985-06-19 | 1985-12-10 | Air Products And Chemicals, Inc. | Production of high purity butene-1 from an n-butane feedstock |
| DE19652273A1 (de) | 1996-12-16 | 1998-06-18 | Basf Ag | Monoolefinische C¶5¶-Mononitrile, Verfahren zu ihrer Herstellung und ihre Verwendung |
| FR2849027B1 (fr) * | 2002-12-23 | 2005-01-21 | Rhodia Polyamide Intermediates | Procede de synthese de composes comprenant des fonctions nitriles a partir de composes a insaturations ethyleniques |
| FR2850966B1 (fr) * | 2003-02-10 | 2005-03-18 | Rhodia Polyamide Intermediates | Procede de fabrication de composes dinitriles |
| FR2854892B1 (fr) * | 2003-05-12 | 2005-06-24 | Rhodia Polyamide Intermediates | Procede de fabrication de dinitriles |
| FR2854891B1 (fr) | 2003-05-12 | 2006-07-07 | Rhodia Polyamide Intermediates | Procede de preparation de dinitriles |
| DE102004004672A1 (de) * | 2004-01-29 | 2005-08-18 | Basf Ag | Verfahren zur Hydrocyanierung |
| JP4509125B2 (ja) | 2004-01-29 | 2010-07-21 | ビーエーエスエフ ソシエタス・ヨーロピア | 直鎖のペンテンニトリルの製造方法 |
| DE102004004724A1 (de) † | 2004-01-29 | 2005-08-18 | Basf Ag | Herstellung von 3-Pentennitril aus 1,3-Butadien |
| FR2878848B1 (fr) * | 2004-12-07 | 2007-01-05 | Rhodia Chimie Sa | Procede de fabrication de composes dinitriles |
| WO2007046799A1 (en) * | 2005-10-18 | 2007-04-26 | Invista Technologies S.A R.L. | Process of making 3-aminopentanenitrile |
| EP1996598B1 (en) * | 2006-03-17 | 2013-10-16 | Invista Technologies S.à.r.l. | Method for the purification of triorganophosphites by treatment with a basic additive |
| US7880028B2 (en) * | 2006-07-14 | 2011-02-01 | Invista North America S.A R.L. | Process for making 3-pentenenitrile by hydrocyanation of butadiene |
| US7919646B2 (en) * | 2006-07-14 | 2011-04-05 | Invista North America S.A R.L. | Hydrocyanation of 2-pentenenitrile |
| US7709674B2 (en) * | 2006-07-14 | 2010-05-04 | Invista North America S.A R.L | Hydrocyanation process with reduced yield losses |
| EP2146930A2 (en) | 2007-05-14 | 2010-01-27 | INVISTA Technologies S.à.r.l. | High efficiency reactor and process |
| EP2164587B1 (en) * | 2007-06-13 | 2018-04-04 | INVISTA Textiles (U.K.) Limited | Process for improving adiponitrile quality |
| WO2009091790A1 (en) * | 2008-01-15 | 2009-07-23 | Invista Technologies S.A.R.L. | Hydrocyanation of pentenenitriles |
| WO2009091771A2 (en) * | 2008-01-15 | 2009-07-23 | Invista Technologies S.A R.L | Process for making and refining 3-pentenenitrile, and for refining 2-methyl-3-butenenitrile |
| JP2011515411A (ja) * | 2008-03-19 | 2011-05-19 | インビスタ テクノロジーズ エス エイ アール エル | シクロドデカトリエンの製造方法およびラウロラクトンの製造方法 |
| US8247621B2 (en) * | 2008-10-14 | 2012-08-21 | Invista North America S.A.R.L. | Process for making 2-secondary-alkyl-4,5-di-(normal-alkyl)phenols |
| WO2011017543A1 (en) * | 2009-08-07 | 2011-02-10 | Invista Technologies S.A. R.L. | Hydrogenation and esterification to form diesters |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3496215A (en) | 1965-11-23 | 1970-02-17 | Du Pont | Hydrocyanation of olefins using selected nickel phosphite catalysts |
| US3496210A (en) | 1966-07-28 | 1970-02-17 | Du Pont | Hydrocyanation of terminal alkynes |
| US3775461A (en) | 1967-11-06 | 1973-11-27 | Du Pont | Hydrocyanation of olefins |
| US3778462A (en) | 1971-06-07 | 1973-12-11 | Gulf Research Development Co | Olefin hydrocyanation reaction |
| US3798256A (en) | 1971-08-02 | 1974-03-19 | Du Pont | Hydrocyanation of olefins |
| US3766237A (en) | 1972-01-25 | 1973-10-16 | Du Pont | Hydrocyanation of olefins |
| US3903120A (en) | 1973-06-19 | 1975-09-02 | Du Pont | Preparation of zerovalent nickel complexes from elemental nickel |
| US3850973A (en) | 1973-09-26 | 1974-11-26 | Du Pont | Hydrocyanation of conjugated diolefins |
| US3920721A (en) | 1974-09-18 | 1975-11-18 | Du Pont | Hydrocyanation of olefins |
| IT1102409B (it) * | 1978-12-20 | 1985-10-07 | Montedison Spa | Processo per la purificazione di olefine |
-
1983
- 1983-03-25 US US06/478,997 patent/US4434316A/en not_active Expired - Lifetime
-
1984
- 1984-03-22 CA CA000450265A patent/CA1217207A/en not_active Expired
- 1984-03-23 DE DE8484301984T patent/DE3465073D1/de not_active Expired
- 1984-03-23 EP EP84301984A patent/EP0123438B1/en not_active Expired
- 1984-03-23 KR KR1019840001502A patent/KR910004132B1/ko not_active Expired
- 1984-03-23 JP JP59054577A patent/JPS59176220A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4434316A (en) | 1984-02-28 |
| KR840007862A (ko) | 1984-12-11 |
| JPH0412248B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-03-04 |
| JPS59176220A (ja) | 1984-10-05 |
| EP0123438B1 (en) | 1987-07-29 |
| DE3465073D1 (en) | 1987-09-03 |
| KR910004132B1 (ko) | 1991-06-22 |
| EP0123438A1 (en) | 1984-10-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1217207A (en) | Separation of alkenes from alkadienes | |
| CA1175068A (en) | Treatment of olefin hydrocyanation products | |
| US9493405B2 (en) | Method for producing linear pentenenitrile | |
| KR101143755B1 (ko) | 디니트릴의 제조 방법 | |
| KR100533900B1 (ko) | 모노올레핀 ｃ5 모노니트릴, 그의 제조 방법 및 용도 | |
| CN103097342B (zh) | 用于制备腈的方法 | |
| KR101064039B1 (ko) | 3-펜텐니트릴의 제조방법 | |
| KR101143754B1 (ko) | 1,3-부타디엔으로부터 3-펜텐니트릴의 제조 | |
| US7566800B2 (en) | Homogeneous isomerization of cis-2-pentene nitrile to form 3-pentene nitrile | |
| RU2315751C2 (ru) | Способ получения и выделения динитрилов | |
| KR101064021B1 (ko) | 펜텐니트릴 이성질체의 분리 방법 | |
| KR102798667B1 (ko) | 아디포니트릴의 제조방법 및 장치 | |
| KR20060136427A (ko) | 펜텐니트릴 이성질체의 분리 방법 | |
| US7687655B2 (en) | Method for the production of dinitrile compounds | |
| KR20060136418A (ko) | 3-펜텐니트릴을 형성하기 위한 시스-2-펜텐니트릴의 균질이성질화 | |
| HK1189874A (en) | Process for making nitriles |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |