CA1220230A - Process for producing tert.butyl alkyl ethers - Google Patents
Process for producing tert.butyl alkyl ethersInfo
- Publication number
- CA1220230A CA1220230A CA000428516A CA428516A CA1220230A CA 1220230 A CA1220230 A CA 1220230A CA 000428516 A CA000428516 A CA 000428516A CA 428516 A CA428516 A CA 428516A CA 1220230 A CA1220230 A CA 1220230A
- Authority
- CA
- Canada
- Prior art keywords
- butene
- tert
- hydrocarbon
- isobutene
- butyl alkyl
- 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
- 238000000034 method Methods 0.000 title claims abstract description 24
- -1 butyl alkyl ethers Chemical class 0.000 title claims abstract description 18
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims abstract description 40
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims abstract description 32
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims abstract description 30
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 11
- 229930195734 saturated hydrocarbon Natural products 0.000 claims abstract description 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 52
- 229930195733 hydrocarbon Natural products 0.000 claims description 34
- 150000002430 hydrocarbons Chemical class 0.000 claims description 34
- 239000004215 Carbon black (E152) Substances 0.000 claims description 25
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 18
- 238000006317 isomerization reaction Methods 0.000 claims description 12
- 238000003786 synthesis reaction Methods 0.000 claims description 10
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 239000003456 ion exchange resin Substances 0.000 claims description 6
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 6
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical class C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 238000005194 fractionation Methods 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 238000010702 ether synthesis reaction Methods 0.000 claims description 2
- 239000000727 fraction Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 238000000926 separation method Methods 0.000 abstract 1
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000001282 iso-butane Substances 0.000 description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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 |
|---|---|---|---|
| IT21384A/82 | 1982-05-20 | ||
| IT21384/82A IT1151183B (it) | 1982-05-20 | 1982-05-20 | Procedimento per la produzione di eteri alchil ter-butilici |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1220230A true CA1220230A (en) | 1987-04-07 |
Family
ID=11180967
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000428516A Expired CA1220230A (en) | 1982-05-20 | 1983-05-19 | Process for producing tert.butyl alkyl ethers |
Country Status (30)
| Country | Link |
|---|---|
| JP (1) | JPS58210039A (forum.php) |
| KR (1) | KR860001854B1 (forum.php) |
| AU (1) | AU1401783A (forum.php) |
| BE (1) | BE896787A (forum.php) |
| BG (1) | BG37678A3 (forum.php) |
| BR (1) | BR8302433A (forum.php) |
| CA (1) | CA1220230A (forum.php) |
| CH (1) | CH653664A5 (forum.php) |
| DD (1) | DD209803A5 (forum.php) |
| DE (1) | DE3318301A1 (forum.php) |
| DK (1) | DK221683A (forum.php) |
| ES (1) | ES8500206A1 (forum.php) |
| FR (1) | FR2527202B1 (forum.php) |
| GB (1) | GB2121407B (forum.php) |
| GR (1) | GR78857B (forum.php) |
| IN (1) | IN159788B (forum.php) |
| IT (1) | IT1151183B (forum.php) |
| LU (1) | LU84805A1 (forum.php) |
| MW (1) | MW1883A1 (forum.php) |
| NL (1) | NL8301819A (forum.php) |
| NO (1) | NO831759L (forum.php) |
| NZ (1) | NZ204032A (forum.php) |
| PH (1) | PH19481A (forum.php) |
| PL (1) | PL242093A1 (forum.php) |
| PT (1) | PT76730B (forum.php) |
| SE (1) | SE8302577L (forum.php) |
| TR (1) | TR21617A (forum.php) |
| YU (1) | YU110083A (forum.php) |
| ZA (1) | ZA833068B (forum.php) |
| ZW (1) | ZW9783A1 (forum.php) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4731490A (en) * | 1986-07-23 | 1988-03-15 | Arco Chemical Company | Process for methyl, tertiary butyl ether production |
| FR2614297B1 (fr) * | 1987-04-24 | 1989-07-21 | Inst Francais Du Petrole | Procede de production de methyl-tertiobutyl-ether a partir de n-butenes. |
| CA2111018A1 (en) * | 1993-01-06 | 1994-07-07 | Jacob N. Rubin | Integrated mtbe process |
| FR2710907B1 (fr) * | 1993-10-08 | 1996-01-05 | Inst Francais Du Petrole | Procédé de production d'éthers tertiaires à partir d'une charge de craquage catalytique comprenant deux étapes de distillation extractive. |
| IT1270675B (it) | 1994-10-19 | 1997-05-07 | Enichem Spa | Procedimento per la separazione di paraffine in miscela con olefine |
| CN103755512B (zh) * | 2013-12-24 | 2016-01-06 | 山东滨州裕华化工厂有限公司 | 醚后液化气分离c4馏分的工艺 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1224294B (de) * | 1961-01-09 | 1966-09-08 | Bayer Ag | Verfahren zur Herstellung von tertiaeren Butylalkylaethern |
| FR2455019A1 (fr) * | 1979-04-24 | 1980-11-21 | Inst Francais Du Petrole | Procede de production de methyltertiobutyl ether a partir de methanol et d'isobutene |
| DE2921576A1 (de) * | 1979-05-28 | 1980-12-04 | Davy International Ag | Verfahren zur herstellung von methyl-tert.-butylaether |
-
1982
- 1982-05-20 IT IT21384/82A patent/IT1151183B/it active
-
1983
- 1983-04-28 AU AU14017/83A patent/AU1401783A/en not_active Abandoned
- 1983-04-28 NZ NZ204032A patent/NZ204032A/en unknown
- 1983-04-28 GR GR71241A patent/GR78857B/el unknown
- 1983-04-29 ZW ZW97/83A patent/ZW9783A1/xx unknown
- 1983-04-29 ZA ZA833068A patent/ZA833068B/xx unknown
- 1983-05-05 CH CH2465/83A patent/CH653664A5/it not_active IP Right Cessation
- 1983-05-05 SE SE8302577A patent/SE8302577L/ not_active Application Discontinuation
- 1983-05-06 BR BR8302433A patent/BR8302433A/pt unknown
- 1983-05-12 GB GB08313098A patent/GB2121407B/en not_active Expired
- 1983-05-13 LU LU84805A patent/LU84805A1/fr unknown
- 1983-05-13 KR KR1019830002066A patent/KR860001854B1/ko not_active Expired
- 1983-05-13 MW MW18/83A patent/MW1883A1/xx unknown
- 1983-05-17 YU YU01100/83A patent/YU110083A/xx unknown
- 1983-05-17 FR FR8308163A patent/FR2527202B1/fr not_active Expired
- 1983-05-18 PH PH28926A patent/PH19481A/en unknown
- 1983-05-18 NO NO831759A patent/NO831759L/no unknown
- 1983-05-18 BG BG061013A patent/BG37678A3/xx unknown
- 1983-05-18 TR TR21617A patent/TR21617A/xx unknown
- 1983-05-18 DK DK221683A patent/DK221683A/da not_active Application Discontinuation
- 1983-05-19 DD DD83251077A patent/DD209803A5/de unknown
- 1983-05-19 CA CA000428516A patent/CA1220230A/en not_active Expired
- 1983-05-19 DE DE19833318301 patent/DE3318301A1/de not_active Withdrawn
- 1983-05-19 PT PT76730A patent/PT76730B/pt unknown
- 1983-05-19 BE BE0/210806A patent/BE896787A/fr not_active IP Right Cessation
- 1983-05-20 PL PL24209383A patent/PL242093A1/xx unknown
- 1983-05-20 IN IN632/CAL/83A patent/IN159788B/en unknown
- 1983-05-20 JP JP58087816A patent/JPS58210039A/ja active Pending
- 1983-05-20 ES ES523006A patent/ES8500206A1/es not_active Expired
- 1983-05-20 NL NL8301819A patent/NL8301819A/nl not_active Application Discontinuation
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |