JPS5931486B2 - オレフィン又は芳香族物質を含有する液状パラフィンからオレフィン又は芳香族物質を定量的に分離する方法 - Google Patents
オレフィン又は芳香族物質を含有する液状パラフィンからオレフィン又は芳香族物質を定量的に分離する方法Info
- Publication number
- JPS5931486B2 JPS5931486B2 JP49147926A JP14792674A JPS5931486B2 JP S5931486 B2 JPS5931486 B2 JP S5931486B2 JP 49147926 A JP49147926 A JP 49147926A JP 14792674 A JP14792674 A JP 14792674A JP S5931486 B2 JPS5931486 B2 JP S5931486B2
- Authority
- JP
- Japan
- Prior art keywords
- olefins
- aromatics
- exchange resin
- aromatic substances
- resin
- 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
- 150000001336 alkenes Chemical class 0.000 title claims description 38
- 238000000034 method Methods 0.000 title claims description 29
- 229940057995 liquid paraffin Drugs 0.000 title claims 2
- 239000000126 substance Substances 0.000 title description 7
- 125000003118 aryl group Chemical group 0.000 title 2
- 238000000926 separation method Methods 0.000 claims description 17
- 239000003729 cation exchange resin Substances 0.000 claims description 15
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 14
- 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 9
- 239000011148 porous material Substances 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 6
- 229910052709 silver Inorganic materials 0.000 claims description 6
- 239000004332 silver Substances 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 5
- 229910021645 metal ion Inorganic materials 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 3
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims 1
- 229910001431 copper ion Inorganic materials 0.000 claims 1
- 239000011347 resin Substances 0.000 description 35
- 229920005989 resin Polymers 0.000 description 35
- 239000000203 mixture Substances 0.000 description 28
- 229930195733 hydrocarbon Natural products 0.000 description 17
- 150000002430 hydrocarbons Chemical class 0.000 description 17
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 13
- 239000004215 Carbon black (E152) Substances 0.000 description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 239000012459 cleaning agent Substances 0.000 description 8
- -1 silver ions Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000003463 adsorbent Substances 0.000 description 7
- 238000001179 sorption measurement Methods 0.000 description 7
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
- 229940023913 cation exchange resins Drugs 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012188 paraffin wax Substances 0.000 description 6
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 6
- 238000003795 desorption Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 229930195734 saturated hydrocarbon Natural products 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 238000006356 dehydrogenation reaction Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000000895 extractive distillation Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 150000005673 monoalkenes Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 2
- 229910052573 porcelain Inorganic materials 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 1
- 238000004438 BET method Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- DIORMHZUUKOISG-UHFFFAOYSA-N sulfoformic acid Chemical compound OC(=O)S(O)(=O)=O DIORMHZUUKOISG-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/12—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers
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)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2364306 | 1973-12-22 | ||
| DE19732364306 DE2364306C3 (de) | 1973-12-22 | Verfahren zur quantitativen Abtrennung von ungesättigten Verbindungen aus Kohlenwasserstoff ge mischen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5095204A JPS5095204A (show.php) | 1975-07-29 |
| JPS5931486B2 true JPS5931486B2 (ja) | 1984-08-02 |
Family
ID=5901792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP49147926A Expired JPS5931486B2 (ja) | 1973-12-22 | 1974-12-23 | オレフィン又は芳香族物質を含有する液状パラフィンからオレフィン又は芳香族物質を定量的に分離する方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3979280A (show.php) |
| JP (1) | JPS5931486B2 (show.php) |
| BE (1) | BE823591A (show.php) |
| CA (1) | CA1048435A (show.php) |
| FR (1) | FR2255276B1 (show.php) |
| GB (1) | GB1442879A (show.php) |
| NL (1) | NL177743C (show.php) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56140932A (en) * | 1980-04-07 | 1981-11-04 | Toray Ind Inc | Isolation of cyclohexene by adsorption |
| JPS59162953A (ja) * | 1983-03-05 | 1984-09-13 | Showa Denko Kk | 陽イオン交換樹脂を用いて糖類及び糖アルコール類を分離する方法 |
| NL8401805A (nl) * | 1984-06-06 | 1986-01-02 | Packard Instr Bv | Adsorptiemateriaal voor olefinen; gaschromatografiekolom; werkwijze voor het selectief verwijderen van olefinen uit een mengsel van koolwaterstoffen. |
| US4992601A (en) * | 1989-02-15 | 1991-02-12 | Energia Andina Ltd. | Process for the selective separation of alkenes and alkynes |
| US5175363A (en) * | 1991-01-28 | 1992-12-29 | Eastman Kodak Company | Method for purification of carboxylic acids and anhydrides |
| US7019188B2 (en) * | 2002-06-14 | 2006-03-28 | Nova Chemicals (International) S.A. | Use of ionic liquids to separate olefins, diolefins and aromatics |
| CA2400714A1 (en) * | 2002-08-28 | 2004-02-28 | Nova Chemicals Corporation | Use of ionic liquids to separate olefins, diolefins and aromatics |
| US20040106838A1 (en) * | 2002-12-02 | 2004-06-03 | Nova Chemicals (International) S.A. | Use of ionic liquids to separate diolefins |
| CN101519602B (zh) * | 2008-02-28 | 2013-04-24 | 中国石油化工股份有限公司 | 一种烃类原料中不饱和烃的捕集材料 |
| CN102802782B (zh) * | 2009-05-19 | 2015-05-13 | 百特基公司 | 多孔聚合物分离材料 |
| KR20160052533A (ko) * | 2013-08-29 | 2016-05-12 | 블루 큐브 아이피 엘엘씨 | 모노비닐 탄화수소 및/또는 비-비닐 화합물로부터 디비닐 탄화수소를 분리하기 위한 공정 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2449402A (en) * | 1944-01-24 | 1948-09-14 | Sun Oil Co | Process for separating aromatic hydrocarbons from a hydrocarbon mixture |
| US2865970A (en) * | 1957-08-06 | 1958-12-23 | Sun Oil Co | Separation of hydrocarbons |
| US3409691A (en) * | 1966-02-01 | 1968-11-05 | Dow Chemical Co | Porous cation exchange resins as selective sorbents in organic systems |
| FR2229440B1 (show.php) * | 1973-05-17 | 1977-07-29 | Inst Francais Du Petrole |
-
1974
- 1974-12-12 US US05/531,950 patent/US3979280A/en not_active Expired - Lifetime
- 1974-12-12 CA CA74215834A patent/CA1048435A/en not_active Expired
- 1974-12-18 GB GB5474774A patent/GB1442879A/en not_active Expired
- 1974-12-19 NL NLAANVRAGE7416607,A patent/NL177743C/xx not_active IP Right Cessation
- 1974-12-19 BE BE151713A patent/BE823591A/xx not_active IP Right Cessation
- 1974-12-20 FR FR7442293A patent/FR2255276B1/fr not_active Expired
- 1974-12-23 JP JP49147926A patent/JPS5931486B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA1048435A (en) | 1979-02-13 |
| GB1442879A (en) | 1976-07-14 |
| NL7416607A (nl) | 1975-06-24 |
| DE2364306B2 (de) | 1976-03-04 |
| FR2255276B1 (show.php) | 1984-10-19 |
| US3979280A (en) | 1976-09-07 |
| FR2255276A1 (show.php) | 1975-07-18 |
| NL177743C (nl) | 1985-11-18 |
| JPS5095204A (show.php) | 1975-07-29 |
| BE823591A (fr) | 1975-06-19 |
| NL177743B (nl) | 1985-06-17 |
| DE2364306A1 (de) | 1975-07-03 |
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