JPH0465054B2 - - Google Patents
Info
- Publication number
- JPH0465054B2 JPH0465054B2 JP17124385A JP17124385A JPH0465054B2 JP H0465054 B2 JPH0465054 B2 JP H0465054B2 JP 17124385 A JP17124385 A JP 17124385A JP 17124385 A JP17124385 A JP 17124385A JP H0465054 B2 JPH0465054 B2 JP H0465054B2
- Authority
- JP
- Japan
- Prior art keywords
- carboxylic acid
- acid
- phase
- aqueous solution
- methanol
- 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 156
- 238000000034 method Methods 0.000 claims description 21
- 150000001336 alkenes Chemical class 0.000 claims description 15
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 63
- 150000001735 carboxylic acids Chemical class 0.000 description 56
- 239000012071 phase Substances 0.000 description 41
- 239000007864 aqueous solution Substances 0.000 description 34
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical group CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 24
- 239000002253 acid Substances 0.000 description 23
- 238000000605 extraction Methods 0.000 description 23
- 229920000098 polyolefin Polymers 0.000 description 19
- 238000011084 recovery Methods 0.000 description 18
- 238000004817 gas chromatography Methods 0.000 description 16
- 239000007788 liquid Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 13
- -1 organic acid salt Chemical class 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 239000012535 impurity Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000001334 alicyclic compounds Chemical group 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 2
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- AOMKQOQXDFDRAW-UHFFFAOYSA-N 1-prop-1-en-2-ylcyclohexene Chemical compound CC(=C)C1=CCCCC1 AOMKQOQXDFDRAW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000011800 void material Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17124385A JPS6233132A (ja) | 1985-08-05 | 1985-08-05 | カルボン酸の精製方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17124385A JPS6233132A (ja) | 1985-08-05 | 1985-08-05 | カルボン酸の精製方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6233132A JPS6233132A (ja) | 1987-02-13 |
| JPH0465054B2 true JPH0465054B2 (enrdf_load_stackoverflow) | 1992-10-16 |
Family
ID=15919694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17124385A Granted JPS6233132A (ja) | 1985-08-05 | 1985-08-05 | カルボン酸の精製方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6233132A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5936041A (en) * | 1994-06-17 | 1999-08-10 | Exxon Chemical Patents Inc | Dispersant additives and process |
-
1985
- 1985-08-05 JP JP17124385A patent/JPS6233132A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6233132A (ja) | 1987-02-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4761505A (en) | Process for recovery of alcohols from sulfuric acid streams | |
| EP0031205B1 (en) | Carbonylation of ethylene or propylene | |
| USRE31010E (en) | Preparation of carboxylic acid esters with BF3 complex catalyst | |
| US4469903A (en) | Process for the production of isopropyl alcohol | |
| CN1027587C (zh) | 制备甲基丙烯酸烷基酯的方法 | |
| AU2004220263B2 (en) | Extraction of oxygenates from a hydrocarbon stream | |
| EP0175443A2 (en) | Improved alcohol recovery process | |
| JP3075834B2 (ja) | 液体抽出によるプロピレンオキシドの精製方法 | |
| US4262138A (en) | Preparation of carboxylic acid esters with BF3 complex catalyst | |
| IL28384A (en) | Process for recovery of glycidol | |
| CN1063421C (zh) | 生产异丙醇的方法 | |
| JPS5924982B2 (ja) | プチレンオキサイドの精製方法 | |
| US2918486A (en) | Extraction of alcohols with propylene carbonate | |
| JPH0465054B2 (enrdf_load_stackoverflow) | ||
| JP3693404B2 (ja) | イソプロピルアルコールの製造方法 | |
| US2626276A (en) | Recovery of organic oxygen-containing compounds from mixtures of hydrocarbon oils | |
| EP0017441B1 (en) | Preparation of esters | |
| JPH04330037A (ja) | 第三級カルボン酸の製造方法 | |
| JPH04270249A (ja) | 炭酸ジメチルの精製法 | |
| JPH08507071A (ja) | ジ−イソプロピルエーテルの製造 | |
| JPH04260611A (ja) | ホウ酸メチルの加水分解による酸化ホウ素の製造方法、および飽和炭化水素のアルコールへの酸化におけるその使用方法 | |
| JPH04221333A (ja) | エチルターシャリーアルキルエーテルの製造方法 | |
| US6166270A (en) | Extractive distillation separation | |
| JPS6240335B2 (enrdf_load_stackoverflow) | ||
| RU2616004C1 (ru) | Способ переработки высококипящих побочных продуктов процесса получения этриола |