JPS58167534A - 第３級ブチルアルキルエ−テルの製法 - Google Patents
第３級ブチルアルキルエ−テルの製法Info
- Publication number
- JPS58167534A JPS58167534A JP58039308A JP3930883A JPS58167534A JP S58167534 A JPS58167534 A JP S58167534A JP 58039308 A JP58039308 A JP 58039308A JP 3930883 A JP3930883 A JP 3930883A JP S58167534 A JPS58167534 A JP S58167534A
- Authority
- JP
- Japan
- Prior art keywords
- reactor
- butadiene
- reaction
- reactants
- tertiary
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000000376 reactant Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- -1 butyl alkyl ether Chemical group 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 150000005215 alkyl ethers Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 5
- 150000001336 alkenes Chemical group 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 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 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 238000004523 catalytic cracking Methods 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 238000004230 steam cracking Methods 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- 241000257465 Echinoidea Species 0.000 description 1
- 244000046038 Ehretia acuminata Species 0.000 description 1
- 235000009300 Ehretia acuminata Nutrition 0.000 description 1
- 241000238413 Octopus Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
Classifications
-
- 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
-
- 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
- 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
- C07C43/06—Diethyl ether
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 |
|---|---|---|---|
| IT20122/82A IT1150678B (it) | 1982-03-12 | 1982-03-12 | Procedimento per la produzione di eteri alchil terbutilici in presenza di butadiene |
| IT20122A/82 | 1982-03-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58167534A true JPS58167534A (ja) | 1983-10-03 |
| JPH0441133B2 JPH0441133B2 (enExample) | 1992-07-07 |
Family
ID=11163984
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58039308A Granted JPS58167534A (ja) | 1982-03-12 | 1983-03-11 | 第３級ブチルアルキルエ−テルの製法 |
Country Status (33)
| Country | Link |
|---|---|
| JP (1) | JPS58167534A (enExample) |
| KR (1) | KR860001359B1 (enExample) |
| AT (1) | AT387959B (enExample) |
| AU (1) | AU559931B2 (enExample) |
| BE (1) | BE896127A (enExample) |
| BR (1) | BR8301020A (enExample) |
| CA (1) | CA1205824A (enExample) |
| CS (1) | CS232749B2 (enExample) |
| DD (1) | DD207194A5 (enExample) |
| DE (1) | DE3308736A1 (enExample) |
| DK (1) | DK65683A (enExample) |
| EG (1) | EG16276A (enExample) |
| ES (1) | ES520857A0 (enExample) |
| FR (1) | FR2523121B1 (enExample) |
| GB (1) | GB2116546B (enExample) |
| GR (1) | GR78796B (enExample) |
| HU (1) | HU196351B (enExample) |
| IN (1) | IN159879B (enExample) |
| IT (1) | IT1150678B (enExample) |
| LU (1) | LU84665A1 (enExample) |
| MX (1) | MX155984A (enExample) |
| NL (1) | NL8300848A (enExample) |
| NO (1) | NO156606C (enExample) |
| NZ (1) | NZ203293A (enExample) |
| PH (1) | PH19851A (enExample) |
| PL (1) | PL140559B1 (enExample) |
| PT (1) | PT76375B (enExample) |
| RU (1) | RU1836318C (enExample) |
| SE (1) | SE461853B (enExample) |
| TR (1) | TR21654A (enExample) |
| YU (1) | YU49483A (enExample) |
| ZA (1) | ZA831152B (enExample) |
| ZM (1) | ZM1583A1 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1190015B (it) * | 1986-05-27 | 1988-02-10 | Snam Progetti | Procedimento per la preparazione di eteri alchilterbutilici |
| GB9027112D0 (en) * | 1990-12-13 | 1991-02-06 | British Petroleum Co Plc | Etherification |
| US7838708B2 (en) | 2001-06-20 | 2010-11-23 | Grt, Inc. | Hydrocarbon conversion process improvements |
| MXPA06000470A (es) | 2003-07-15 | 2006-08-23 | Grt Inc | Sintesis de hidrocarburos. |
| US20050171393A1 (en) | 2003-07-15 | 2005-08-04 | Lorkovic Ivan M. | Hydrocarbon synthesis |
| US20080275284A1 (en) | 2004-04-16 | 2008-11-06 | Marathon Oil Company | Process 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 |
| US7674941B2 (en) | 2004-04-16 | 2010-03-09 | Marathon Gtf Technology, Ltd. | Processes 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 |
| US8642822B2 (en) | 2004-04-16 | 2014-02-04 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons using microchannel reactor |
| US8173851B2 (en) | 2004-04-16 | 2012-05-08 | Marathon Gtf Technology, Ltd. | Processes for converting gaseous alkanes to liquid hydrocarbons |
| CN101817720A (zh) | 2006-02-03 | 2010-09-01 | Grt公司 | 天然气转化为液体烃的连续方法 |
| EP1993951B1 (en) | 2006-02-03 | 2014-07-30 | GRT, Inc. | Separation of light gases from bromine |
| AU2008256606A1 (en) | 2007-05-24 | 2008-12-04 | Grt, Inc. | Zone reactor incorporating reversible hydrogen halide capture and release |
| 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 |
| NZ591207A (en) | 2008-07-18 | 2013-03-28 | Grt Inc | Continuous process for converting natural gas to liquid hydrocarbons |
| US8367884B2 (en) | 2010-03-02 | 2013-02-05 | Marathon Gtf Technology, Ltd. | Processes and systems for the staged synthesis of alkyl bromides |
| US8198495B2 (en) | 2010-03-02 | 2012-06-12 | 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 |
| US8686211B2 (en) | 2011-09-07 | 2014-04-01 | Shell Oil Company | Process for preparing ethylene and/or propylene and a butadiene-enriched product |
| 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 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4961109A (enExample) * | 1972-10-12 | 1974-06-13 | ||
| JPS5220963A (en) * | 1975-06-30 | 1977-02-17 | Daido Steel Co Ltd | Method of manufacturing precious metal powder |
| JPS5232241A (en) * | 1975-09-05 | 1977-03-11 | Fujitsu Ltd | Wireless data transmission system |
| JPS5616424A (en) * | 1979-07-14 | 1981-02-17 | Basf Ag | Method of manufacturing methylltertiaryy butylether as well as obtaining isobutene simultaneously |
| JPS58146524A (ja) * | 1982-02-25 | 1983-09-01 | Mitsubishi Gas Chem Co Inc | 第３級エ−テルの製造法 |
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 |
| IT1012687B (it) * | 1974-05-21 | 1977-03-10 | Snam Progetti | Procedimento per la sintesi di ete ri alchil ter butilici a partire da un alcool primario ed isobutilene in presenza di butadiene |
| FR2440931A1 (fr) * | 1978-11-08 | 1980-06-06 | Inst Francais Du Petrole | Procede de production d'ethers par reaction d'olefines avec des alcools |
-
1982
- 1982-03-12 IT IT20122/82A patent/IT1150678B/it active
-
1983
- 1983-02-15 NZ NZ203293A patent/NZ203293A/en unknown
- 1983-02-15 DK DK65683A patent/DK65683A/da not_active Application Discontinuation
- 1983-02-16 CA CA000421707A patent/CA1205824A/en not_active Expired
- 1983-02-18 GB GB08304536A patent/GB2116546B/en not_active Expired
- 1983-02-21 ZA ZA831152A patent/ZA831152B/xx unknown
- 1983-02-21 KR KR1019830000697A patent/KR860001359B1/ko not_active Expired
- 1983-02-22 AU AU11744/83A patent/AU559931B2/en not_active Expired - Fee Related
- 1983-02-23 GR GR70589A patent/GR78796B/el unknown
- 1983-02-24 PL PL1983240765A patent/PL140559B1/pl unknown
- 1983-02-25 LU LU84665A patent/LU84665A1/fr unknown
- 1983-02-25 SE SE8301069A patent/SE461853B/sv not_active IP Right Cessation
- 1983-02-25 MX MX196394A patent/MX155984A/es unknown
- 1983-02-25 BR BR8301020A patent/BR8301020A/pt unknown
- 1983-03-02 YU YU00494/83A patent/YU49483A/xx unknown
- 1983-03-03 CS CS831493A patent/CS232749B2/cs unknown
- 1983-03-04 NO NO830743A patent/NO156606C/no unknown
- 1983-03-07 ZM ZM15/83A patent/ZM1583A1/xx unknown
- 1983-03-08 AT AT0080383A patent/AT387959B/de not_active IP Right Cessation
- 1983-03-08 PH PH28617A patent/PH19851A/en unknown
- 1983-03-09 TR TR21654A patent/TR21654A/xx unknown
- 1983-03-09 NL NL8300848A patent/NL8300848A/nl not_active Application Discontinuation
- 1983-03-10 BE BE0/210292A patent/BE896127A/fr not_active IP Right Cessation
- 1983-03-11 JP JP58039308A patent/JPS58167534A/ja active Granted
- 1983-03-11 DD DD83248748A patent/DD207194A5/de not_active IP Right Cessation
- 1983-03-11 HU HU83846A patent/HU196351B/hu unknown
- 1983-03-11 ES ES520857A patent/ES520857A0/es active Granted
- 1983-03-11 IN IN302/CAL/83A patent/IN159879B/en unknown
- 1983-03-11 DE DE19833308736 patent/DE3308736A1/de active Granted
- 1983-03-11 PT PT76375A patent/PT76375B/pt unknown
- 1983-03-11 FR FR8304015A patent/FR2523121B1/fr not_active Expired
- 1983-03-11 RU SU833560849A patent/RU1836318C/ru active
- 1983-03-12 EG EG167/83A patent/EG16276A/xx active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4961109A (enExample) * | 1972-10-12 | 1974-06-13 | ||
| JPS5220963A (en) * | 1975-06-30 | 1977-02-17 | Daido Steel Co Ltd | Method of manufacturing precious metal powder |
| JPS5232241A (en) * | 1975-09-05 | 1977-03-11 | Fujitsu Ltd | Wireless data transmission system |
| JPS5616424A (en) * | 1979-07-14 | 1981-02-17 | Basf Ag | Method of manufacturing methylltertiaryy butylether as well as obtaining isobutene simultaneously |
| JPS58146524A (ja) * | 1982-02-25 | 1983-09-01 | Mitsubishi Gas Chem Co Inc | 第３級エ−テルの製造法 |
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