DE2457777A1 - Verfahren zur herstellung von isopren - Google Patents
Verfahren zur herstellung von isoprenInfo
- Publication number
- DE2457777A1 DE2457777A1 DE19742457777 DE2457777A DE2457777A1 DE 2457777 A1 DE2457777 A1 DE 2457777A1 DE 19742457777 DE19742457777 DE 19742457777 DE 2457777 A DE2457777 A DE 2457777A DE 2457777 A1 DE2457777 A1 DE 2457777A1
- Authority
- DE
- Germany
- Prior art keywords
- methylbutene
- diluent
- chlorine
- range
- product
- 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.)
- Pending
Links
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 title claims description 38
- 238000000034 method Methods 0.000 title claims description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 claims description 51
- 239000003085 diluting agent Substances 0.000 claims description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 24
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 24
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 23
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 22
- 239000000460 chlorine Substances 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 20
- 238000007033 dehydrochlorination reaction Methods 0.000 claims description 17
- 239000007789 gas Substances 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 239000001282 iso-butane Substances 0.000 claims description 10
- 238000005660 chlorination reaction Methods 0.000 claims description 9
- 239000003701 inert diluent Substances 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 5
- 238000010924 continuous production Methods 0.000 claims description 2
- 239000000047 product Substances 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 18
- PGEVTVXEERFABN-UHFFFAOYSA-N 1,1-dichloropentane Chemical compound CCCCC(Cl)Cl PGEVTVXEERFABN-UHFFFAOYSA-N 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000000203 mixture Substances 0.000 description 8
- 235000012239 silicon dioxide Nutrition 0.000 description 8
- UPJCRKZUCADENN-UHFFFAOYSA-N 1-chloropent-2-ene Chemical compound CCC=CCCl UPJCRKZUCADENN-UHFFFAOYSA-N 0.000 description 7
- 235000013844 butane Nutrition 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- CRNIHJHMEQZAAS-UHFFFAOYSA-N tert-amyl chloride Chemical compound CCC(C)(C)Cl CRNIHJHMEQZAAS-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000010453 quartz Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- SQCZQTSHSZLZIQ-UHFFFAOYSA-N 1-chloropentane Chemical compound CCCCCCl SQCZQTSHSZLZIQ-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 229910052681 coesite Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 229910052906 cristobalite Inorganic materials 0.000 description 2
- 238000001030 gas--liquid chromatography Methods 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910052682 stishovite Inorganic materials 0.000 description 2
- 229910052905 tridymite Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- MPSRDSQITWIFME-UHFFFAOYSA-N 1,1,1-trichloropentane Chemical compound CCCCC(Cl)(Cl)Cl MPSRDSQITWIFME-UHFFFAOYSA-N 0.000 description 1
- XEHOOSVDEMUKEF-UHFFFAOYSA-N 1,1-dichloropent-2-ene Chemical class CCC=CC(Cl)Cl XEHOOSVDEMUKEF-UHFFFAOYSA-N 0.000 description 1
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- MOUDFOLIRVUWKC-UHFFFAOYSA-N 3,3-dichloropentane Chemical class CCC(Cl)(Cl)CC MOUDFOLIRVUWKC-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000575946 Ione Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- LTXREWYXXSTFRX-QGZVFWFLSA-N Linagliptin Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=CC4=C(C)N=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 LTXREWYXXSTFRX-QGZVFWFLSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
- 229910001626 barium chloride Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
- C07C17/02—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/26—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms
- C07C1/30—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms by splitting-off the elements of hydrogen halide from a single molecule
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/12—Alkadienes
- C07C11/173—Alkadienes with five carbon atoms
- C07C11/18—Isoprene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S585/00—Chemistry of hydrocarbon compounds
- Y10S585/929—Special chemical considerations
- Y10S585/93—Process including synthesis of nonhydrocarbon intermediate
- Y10S585/935—Halogen-containing
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3509372A GB1395926A (en) | 1972-07-27 | 1972-07-27 | Process for the production of isoprene by the chlorination/ dehydrochlorination of 2-methylbutene-2 |
| CA215,115A CA1026772A (en) | 1972-07-27 | 1974-12-03 | Isoprene production |
| US529559A US3907917A (en) | 1972-07-27 | 1974-12-04 | Isoprene production |
| DE19742457777 DE2457777A1 (de) | 1972-07-27 | 1974-12-06 | Verfahren zur herstellung von isopren |
| FR7440215A FR2294152A1 (fr) | 1972-07-27 | 1974-12-09 | Procede de production d'isoprene |
| NL7416183A NL7416183A (nl) | 1972-07-27 | 1974-12-12 | Werkwijze voor de bereiding van isopreen. |
| IT30477/74A IT1027628B (it) | 1972-07-27 | 1974-12-12 | Processo per la produzione di isoprene |
| JP49145529A JPS5175005A (en) | 1972-07-27 | 1974-12-18 | Isopurenno seizohoho |
| BE151668A BE823540A (fr) | 1972-07-27 | 1974-12-18 | Production de l'isoprene |
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3509372A GB1395926A (en) | 1972-07-27 | 1972-07-27 | Process for the production of isoprene by the chlorination/ dehydrochlorination of 2-methylbutene-2 |
| CA215,115A CA1026772A (en) | 1972-07-27 | 1974-12-03 | Isoprene production |
| US529559A US3907917A (en) | 1972-07-27 | 1974-12-04 | Isoprene production |
| DE19742457777 DE2457777A1 (de) | 1972-07-27 | 1974-12-06 | Verfahren zur herstellung von isopren |
| FR7440215A FR2294152A1 (fr) | 1972-07-27 | 1974-12-09 | Procede de production d'isoprene |
| NL7416183A NL7416183A (nl) | 1972-07-27 | 1974-12-12 | Werkwijze voor de bereiding van isopreen. |
| IT30477/74A IT1027628B (it) | 1972-07-27 | 1974-12-12 | Processo per la produzione di isoprene |
| JP49145529A JPS5175005A (en) | 1972-07-27 | 1974-12-18 | Isopurenno seizohoho |
| BE151668A BE823540A (fr) | 1972-07-27 | 1974-12-18 | Production de l'isoprene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2457777A1 true DE2457777A1 (de) | 1976-06-16 |
Family
ID=27575669
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742457777 Pending DE2457777A1 (de) | 1972-07-27 | 1974-12-06 | Verfahren zur herstellung von isopren |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3907917A (enExample) |
| JP (1) | JPS5175005A (enExample) |
| BE (1) | BE823540A (enExample) |
| CA (1) | CA1026772A (enExample) |
| DE (1) | DE2457777A1 (enExample) |
| FR (1) | FR2294152A1 (enExample) |
| GB (1) | GB1395926A (enExample) |
| IT (1) | IT1027628B (enExample) |
| NL (1) | NL7416183A (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7838708B2 (en) | 2001-06-20 | 2010-11-23 | Grt, Inc. | Hydrocarbon conversion process improvements |
| AU2004268935B2 (en) | 2003-07-15 | 2010-12-02 | Grt, Inc. | Hydrocarbon synthesis |
| US20050171393A1 (en) | 2003-07-15 | 2005-08-04 | Lorkovic Ivan M. | Hydrocarbon synthesis |
| US8642822B2 (en) | 2004-04-16 | 2014-02-04 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor |
| US7674941B2 (en) | 2004-04-16 | 2010-03-09 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
| US7244867B2 (en) | 2004-04-16 | 2007-07-17 | Marathon Oil Company | Process for converting gaseous alkanes to liquid hydrocarbons |
| US20080275284A1 (en) | 2004-04-16 | 2008-11-06 | Marathon Oil Company | Process for converting gaseous alkanes to liquid hydrocarbons |
| US20060100469A1 (en) * | 2004-04-16 | 2006-05-11 | Waycuilis John J | Process for converting gaseous alkanes to olefins and liquid hydrocarbons |
| US8173851B2 (en) | 2004-04-16 | 2012-05-08 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
| UA95943C2 (ru) | 2006-02-03 | 2011-09-26 | ДжиАрТи, ИНК. | Отделение легких газов от галогенов |
| AP2012006510A0 (en) | 2006-02-03 | 2012-10-31 | Grt Inc | Continuous process for converting natural gas to liquid hydrocarbons |
| CA2687589A1 (en) | 2007-05-24 | 2008-12-04 | Grt, Inc. | Zone reactor incorporating reversible hydrogen halide capture and release |
| US20090312586A1 (en) * | 2008-06-13 | 2009-12-17 | Marathon Gtf Technology, Ltd. | Hydrogenation of multi-brominated alkanes |
| US8282810B2 (en) | 2008-06-13 | 2012-10-09 | Marathon Gtf Technology, Ltd. | Bromine-based method and system for converting gaseous alkanes to liquid hydrocarbons using electrolysis for bromine recovery |
| SG192538A1 (en) | 2008-07-18 | 2013-08-30 | Grt Inc | Continuous process for converting natural gas to liquid hydrocarbons |
| US20110015458A1 (en) * | 2009-07-15 | 2011-01-20 | Marathon Gtf Technology, Ltd. | Conversion of hydrogen bromide to elemental bromine |
| US8198495B2 (en) * | 2010-03-02 | 2012-06-12 | Marathon Gtf Technology, Ltd. | Processes and systems for the staged synthesis of alkyl bromides |
| US8367884B2 (en) | 2010-03-02 | 2013-02-05 | Marathon Gtf Technology, Ltd. | Processes and systems for the staged synthesis of alkyl bromides |
| US8815050B2 (en) | 2011-03-22 | 2014-08-26 | Marathon Gtf Technology, Ltd. | Processes and systems for drying liquid bromine |
| US8436220B2 (en) | 2011-06-10 | 2013-05-07 | Marathon Gtf Technology, Ltd. | Processes and systems for demethanization of brominated hydrocarbons |
| US8829256B2 (en) | 2011-06-30 | 2014-09-09 | Gtc Technology Us, Llc | Processes and systems for fractionation of brominated hydrocarbons in the conversion of natural gas to liquid hydrocarbons |
| US8802908B2 (en) | 2011-10-21 | 2014-08-12 | Marathon Gtf Technology, Ltd. | Processes and systems for separate, parallel methane and higher alkanes' bromination |
| US9193641B2 (en) | 2011-12-16 | 2015-11-24 | Gtc Technology Us, Llc | Processes and systems for conversion of alkyl bromides to higher molecular weight hydrocarbons in circulating catalyst reactor-regenerator systems |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1298929A (en) * | 1912-02-05 | 1919-04-01 | Alien Property Custodian | Producing isoprene. |
| US1198943A (en) * | 1913-06-28 | 1916-09-19 | Francis Edward Matthews | Manufacture of unsaturated hydrocarbons. |
| US2288580A (en) * | 1938-09-15 | 1942-06-30 | Baehr Hans | Production of unsaturated compounds |
| US2243191A (en) * | 1938-10-04 | 1941-05-27 | Jasco Inc | Production of olefins and diolefins |
| US2310523A (en) * | 1938-12-19 | 1943-02-09 | Shell Dev | Process for the production of diolefins |
| US3796767A (en) * | 1973-04-19 | 1974-03-12 | Gulf Research Development Co | Process for preparing diolefins |
-
1972
- 1972-07-27 GB GB3509372A patent/GB1395926A/en not_active Expired
-
1974
- 1974-12-03 CA CA215,115A patent/CA1026772A/en not_active Expired
- 1974-12-04 US US529559A patent/US3907917A/en not_active Expired - Lifetime
- 1974-12-06 DE DE19742457777 patent/DE2457777A1/de active Pending
- 1974-12-09 FR FR7440215A patent/FR2294152A1/fr active Granted
- 1974-12-12 IT IT30477/74A patent/IT1027628B/it active
- 1974-12-12 NL NL7416183A patent/NL7416183A/xx not_active Application Discontinuation
- 1974-12-18 BE BE151668A patent/BE823540A/xx unknown
- 1974-12-18 JP JP49145529A patent/JPS5175005A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2294152A1 (fr) | 1976-07-09 |
| NL7416183A (nl) | 1976-06-15 |
| IT1027628B (it) | 1978-12-20 |
| FR2294152B1 (enExample) | 1978-04-28 |
| BE823540A (fr) | 1975-06-18 |
| GB1395926A (en) | 1975-05-29 |
| CA1026772A (en) | 1978-02-21 |
| US3907917A (en) | 1975-09-23 |
| JPS5175005A (en) | 1976-06-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |