CS209404B2 - Method of aespeiring 1,3-butadien from the hydrocarbon mixtures - Google Patents
Method of aespeiring 1,3-butadien from the hydrocarbon mixtures Download PDFInfo
- Publication number
- CS209404B2 CS209404B2 CS668412A CS841266A CS209404B2 CS 209404 B2 CS209404 B2 CS 209404B2 CS 668412 A CS668412 A CS 668412A CS 841266 A CS841266 A CS 841266A CS 209404 B2 CS209404 B2 CS 209404B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- butadiene
- extraction
- solvent
- hydrocarbons
- conjugated
- Prior art date
Links
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 title claims abstract description 73
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 43
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 39
- 239000000203 mixture Substances 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 19
- 239000004215 Carbon black (E152) Substances 0.000 title abstract description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 51
- 239000002904 solvent Substances 0.000 claims abstract description 47
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical group [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims abstract description 12
- -1 aliphatic acid amide Chemical class 0.000 claims abstract description 9
- 239000003112 inhibitor Substances 0.000 claims abstract description 7
- 235000010288 sodium nitrite Nutrition 0.000 claims abstract description 6
- 150000005673 monoalkenes Chemical class 0.000 claims abstract description 5
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000004821 distillation Methods 0.000 claims description 52
- 238000000605 extraction Methods 0.000 claims description 52
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical group CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 claims description 24
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 18
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 claims description 17
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 14
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 14
- IBXNCJKFFQIKKY-UHFFFAOYSA-N 1-pentyne Chemical group CCCC#C IBXNCJKFFQIKKY-UHFFFAOYSA-N 0.000 claims description 10
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 8
- 239000002798 polar solvent Substances 0.000 claims description 8
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 7
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 4
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- VLLYOYVKQDKAHN-UHFFFAOYSA-N buta-1,3-diene;2-methylbuta-1,3-diene Chemical compound C=CC=C.CC(=C)C=C VLLYOYVKQDKAHN-UHFFFAOYSA-N 0.000 claims description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 2
- 150000001993 dienes Chemical class 0.000 abstract description 62
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 abstract description 41
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 abstract description 36
- 238000000895 extractive distillation Methods 0.000 abstract description 19
- 229930195735 unsaturated hydrocarbon Natural products 0.000 abstract description 13
- 238000011084 recovery Methods 0.000 abstract description 8
- 239000007788 liquid Substances 0.000 abstract description 4
- 238000000926 separation method Methods 0.000 abstract description 3
- 150000001408 amides Chemical class 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- BJEMXPVDXFSROA-UHFFFAOYSA-N 3-butylbenzene-1,2-diol Chemical group CCCCC1=CC=CC(O)=C1O BJEMXPVDXFSROA-UHFFFAOYSA-N 0.000 abstract 1
- 229920006385 Geon Polymers 0.000 abstract 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- HCTYEJBRDPGMGY-UHFFFAOYSA-N benzaldehyde;furan-2-carbaldehyde Chemical group O=CC1=CC=CO1.O=CC1=CC=CC=C1 HCTYEJBRDPGMGY-UHFFFAOYSA-N 0.000 abstract 1
- 229940113088 dimethylacetamide Drugs 0.000 abstract 1
- 238000009835 boiling Methods 0.000 description 18
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 15
- 239000007789 gas Substances 0.000 description 14
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 10
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical class CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 7
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 6
- 210000000540 fraction c Anatomy 0.000 description 6
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 230000000707 stereoselective effect Effects 0.000 description 6
- 239000005062 Polybutadiene Substances 0.000 description 5
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 5
- 239000007791 liquid phase Substances 0.000 description 5
- 229920002857 polybutadiene Polymers 0.000 description 5
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical group CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 4
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical compound C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 238000006356 dehydrogenation reaction Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000001282 iso-butane Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- LLCSWKVOHICRDD-UHFFFAOYSA-N buta-1,3-diyne Chemical group C#CC#C LLCSWKVOHICRDD-UHFFFAOYSA-N 0.000 description 2
- 235000013844 butane Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000003915 liquefied petroleum gas Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000004227 thermal cracking Methods 0.000 description 2
- PMJHHCWVYXUKFD-PLNGDYQASA-N (3z)-penta-1,3-diene Chemical compound C\C=C/C=C PMJHHCWVYXUKFD-PLNGDYQASA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001361 allenes Chemical class 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- LVMTVPFRTKXRPH-UHFFFAOYSA-N penta-1,2-diene Chemical compound CCC=C=C LVMTVPFRTKXRPH-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
- 239000003208 petroleum Substances 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/04—Purification; Separation; Use of additives by distillation
- C07C7/05—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds
- C07C7/08—Purification; Separation; Use of additives by distillation with the aid of auxiliary compounds by extractive distillation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8140265 | 1965-12-30 | ||
| JP8140165 | 1965-12-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS209404B2 true CS209404B2 (en) | 1981-12-31 |
Family
ID=26422426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS668412A CS209404B2 (en) | 1965-12-30 | 1966-12-30 | Method of aespeiring 1,3-butadien from the hydrocarbon mixtures |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3436438A (en, 2012) |
| BE (1) | BE692004A (en, 2012) |
| BG (1) | BG22068A3 (en, 2012) |
| CS (1) | CS209404B2 (en, 2012) |
| DE (1) | DE1568902C3 (en, 2012) |
| DK (1) | DK137987B (en, 2012) |
| ES (1) | ES335072A1 (en, 2012) |
| FI (1) | FI48608C (en, 2012) |
| FR (1) | FR1513458A (en, 2012) |
| GB (1) | GB1148100A (en, 2012) |
| IL (1) | IL27134A (en, 2012) |
| NL (1) | NL6618401A (en, 2012) |
| NO (1) | NO116543B (en, 2012) |
| SE (1) | SE353078B (en, 2012) |
| YU (1) | YU34018B (en, 2012) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3496070A (en) * | 1967-11-09 | 1970-02-17 | Petro Tex Chem Corp | Purification of unsaturated hydrocarbons by extractive distillation with addition of liquid solvent to stripper overhead |
| US3496069A (en) * | 1967-11-09 | 1970-02-17 | Petro Tex Chem Corp | Purification of unsaturated hydrocarbons by extractive distillation with recycle of stripper overhead |
| AU468106B2 (en) * | 1970-12-29 | 1976-01-08 | Snamprogetti S.P.A. | Process forthe recovery of isophrene from mixtures containing thesame |
| US3898135A (en) * | 1971-07-23 | 1975-08-05 | Petro Tex Chem Corp | Extractive distillation of C{HD 4 {B hydrocarbons using a three component solvent system |
| DE2516362C3 (de) * | 1975-04-15 | 1987-10-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Gewinnung von 1,3-Butadien aus einem C↓4↓-Kohlenwasserstoffgemisch |
| US4054613A (en) * | 1975-10-20 | 1977-10-18 | Phillips Petroleum Company | Butadiene production and purification |
| US4081332A (en) * | 1976-08-27 | 1978-03-28 | The B. F. Goodrich Company | Extractive distillation of C5 hydrocarbons using acetonitrile and additives |
| US4038156A (en) * | 1976-09-21 | 1977-07-26 | Shell Oil Company | Butadiene recovery process |
| US4128457A (en) * | 1977-03-09 | 1978-12-05 | Societa' Italiana Resine S.I.R. S.P.A. | Process for the separation of butadiene by plural stage extractive distillation |
| US4166771A (en) * | 1977-03-23 | 1979-09-04 | Phillip Petroleum Company | Butadiene recovery |
| US4090923A (en) * | 1977-04-06 | 1978-05-23 | Phillips Petroleum Company | Butadiene purification with simultaneous prefractionation and vinylacetylene rejection |
| US4134795A (en) * | 1978-04-05 | 1979-01-16 | The Goodyear Tire & Rubber Company | Acetylenes removal from diolefin streams by extractive distillation |
| DE2911393C2 (de) * | 1979-03-23 | 1984-07-19 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Gewinnung eines konjugierten Diolefins aus einem C↓4↓-oder C↓5↓-Kohlenwasserstoffgemisch |
| DE2911395C2 (de) * | 1979-03-23 | 1985-03-14 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Gewinnung eines konjugierten Diolefins aus einem C↓4↓- oder C↓5↓-Kohlenwasserstoffgemisch |
| DE2911394B1 (de) * | 1979-03-23 | 1980-04-30 | Basf Ag | Verfahren zur Gewinnung eines konjugierten Diolefins aus einem C4- oder C5- Kohlenwasserstoffgemisch |
| JPS5681526A (en) * | 1979-12-06 | 1981-07-03 | Nippon Zeon Co Ltd | Polymerization prevention of conjugated dienes |
| DE3339157A1 (de) * | 1983-10-28 | 1985-05-09 | Basf Ag, 6700 Ludwigshafen | Verfahren zur gewinnung eines konjugierten diolefins und/oder olefins aus einem c(pfeil abwaerts)4(pfeil abwaerts)- oder c(pfeil abwaerts)5(pfeil abwaerts)-kohlenwasserstoffgemisch |
| JP4134391B2 (ja) * | 1998-04-07 | 2008-08-20 | 日本ゼオン株式会社 | 不飽和炭化水素の分離精製装置および分離精製方法 |
| TW583178B (en) * | 2001-09-29 | 2004-04-11 | China Petrochemical Corp | Process for separating C5 cuts obtained from a petroleum cracking process |
| DE10233621A1 (de) * | 2002-07-24 | 2004-02-19 | Basf Ag | Verfahren zur Aufarbeitung von Roh-1,3-Butadien |
| US8197898B2 (en) * | 2005-03-29 | 2012-06-12 | Tokyo Electron Limited | Method and system for depositing a layer from light-induced vaporization of a solid precursor |
| US7348466B2 (en) * | 2005-04-13 | 2008-03-25 | Equistar Chemicals, Lp | Solvent extraction |
| US20070043247A1 (en) * | 2005-08-19 | 2007-02-22 | Webber Kenneth M | Diisobutylene production |
| US8080140B2 (en) * | 2007-04-18 | 2011-12-20 | Exxonmobil Chemical Patents Inc. | Process for debottlenecking a system for the separation of a conjugated diolefin |
| US7718841B2 (en) * | 2008-06-09 | 2010-05-18 | Equistar Chemicals, Lp | Extractive distillation |
| US8361280B2 (en) * | 2008-11-24 | 2013-01-29 | Basf Se | Process for distillatively obtaining pure 1,3-butadiene from crude 1,3-butadiene |
| US8222474B2 (en) * | 2009-05-22 | 2012-07-17 | Equistar Chemicals, L.P. | Fractional extraction of butadiene |
| WO2014203207A1 (en) | 2013-06-19 | 2014-12-24 | Saudi Basic Industries Corporation | Co-extraction systems for separation and purification of butadiene and isoprene |
| WO2016097999A1 (en) | 2014-12-18 | 2016-06-23 | Sabic Global Technologies B.V. | Isoprene extraction with preserved c5 feedstock |
| WO2021048655A1 (en) | 2019-09-13 | 2021-03-18 | Sabic Global Technologies B.V. | Integrated systems and methods for producing 1,3-butadiene via extractive distillation, distillation, and/or selective hydrogenation |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2338041A (en) * | 1940-11-01 | 1943-12-28 | Carl B King | Cigarette package |
| US2386927A (en) * | 1941-03-22 | 1945-10-16 | Phillips Petroleum Co | Process for separating diolefins |
| US3000794A (en) * | 1958-05-19 | 1961-09-19 | Petro Tex Chem Corp | Extractive distillation of vinyl acetylene in the purification of butadiene |
| US2993841A (en) * | 1959-09-25 | 1961-07-25 | Shell Oil Co | Extractive distillation with dimethylformamide |
| DE1163795B (de) * | 1961-11-24 | 1964-02-27 | Basf Ag | Verfahren zur Entfernung geringer Mengen von hoehermolekularen Acetylenen und Allenen aus konjugierten Diolefinen |
| BE672305A (en, 2012) * | 1962-05-18 | |||
| GB983783A (en) * | 1963-10-25 | 1965-02-17 | Shell Int Research | Process for the removal of alkynes from hydrocarbon mixtures containing alkadienes |
| US3309412A (en) * | 1964-04-17 | 1967-03-14 | Japanese Geon Co Ltd | Method of preventing the polymerization of butadiene |
-
1966
- 1966-12-22 SE SE17625/66A patent/SE353078B/xx unknown
- 1966-12-23 DE DE1568902A patent/DE1568902C3/de not_active Expired
- 1966-12-23 IL IL27134A patent/IL27134A/xx unknown
- 1966-12-27 US US604923A patent/US3436438A/en not_active Expired - Lifetime
- 1966-12-29 ES ES335072A patent/ES335072A1/es not_active Expired
- 1966-12-29 DK DK673266AA patent/DK137987B/da unknown
- 1966-12-29 FR FR89408A patent/FR1513458A/fr not_active Expired
- 1966-12-29 GB GB58178/66A patent/GB1148100A/en not_active Expired
- 1966-12-29 NO NO166199A patent/NO116543B/no unknown
- 1966-12-30 NL NL6618401A patent/NL6618401A/xx unknown
- 1966-12-30 CS CS668412A patent/CS209404B2/cs unknown
- 1966-12-30 YU YU2484/66A patent/YU34018B/xx unknown
- 1966-12-30 FI FI3496/66A patent/FI48608C/fi active
- 1966-12-30 BE BE692004D patent/BE692004A/xx not_active IP Right Cessation
- 1966-12-30 BG BG7343A patent/BG22068A3/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK137987C (en, 2012) | 1979-01-02 |
| NO116543B (en, 2012) | 1969-04-14 |
| DE1568902A1 (de) | 1972-03-09 |
| FI48608C (fi) | 1983-08-01 |
| FR1513458A (fr) | 1968-02-16 |
| YU34018B (en) | 1978-10-31 |
| BG22068A3 (en, 2012) | 1976-11-25 |
| DK137987B (da) | 1978-06-19 |
| BE692004A (en, 2012) | 1967-05-29 |
| SE353078B (en, 2012) | 1973-01-22 |
| IL27134A (en) | 1970-08-19 |
| NL6618401A (en, 2012) | 1967-07-03 |
| DE1568902B2 (de) | 1973-01-18 |
| DE1568902C3 (de) | 1980-09-25 |
| YU248466A (en) | 1978-05-15 |
| US3436438A (en) | 1969-04-01 |
| FI48608B (en, 2012) | 1974-07-31 |
| ES335072A1 (es) | 1968-03-01 |
| GB1148100A (en) | 1969-04-10 |
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