JPS6032605B2 - 液状パラフイン系炭化水素混合物から不飽和化合物を実際に大量に分離する方法 - Google Patents
液状パラフイン系炭化水素混合物から不飽和化合物を実際に大量に分離する方法Info
- Publication number
- JPS6032605B2 JPS6032605B2 JP51136164A JP13616476A JPS6032605B2 JP S6032605 B2 JPS6032605 B2 JP S6032605B2 JP 51136164 A JP51136164 A JP 51136164A JP 13616476 A JP13616476 A JP 13616476A JP S6032605 B2 JPS6032605 B2 JP S6032605B2
- Authority
- JP
- Japan
- Prior art keywords
- unsaturated compounds
- hydrocarbon
- resin
- exchanger resin
- desorption
- 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 description 40
- 150000001875 compounds Chemical class 0.000 title claims description 30
- 229930195733 hydrocarbon Natural products 0.000 title claims description 27
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 27
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 24
- 239000000203 mixture Substances 0.000 title claims description 24
- 239000007788 liquid Substances 0.000 title claims description 12
- 239000011347 resin Substances 0.000 claims description 43
- 229920005989 resin Polymers 0.000 claims description 43
- 239000012188 paraffin wax Substances 0.000 claims description 15
- 238000003795 desorption Methods 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 11
- 238000001179 sorption measurement Methods 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 10
- 150000001768 cations Chemical class 0.000 claims description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
- 229910052709 silver Inorganic materials 0.000 claims description 6
- 239000004332 silver Substances 0.000 claims description 6
- 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 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- 239000003729 cation exchange resin Substances 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 150000001879 copper Chemical class 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 238000012545 processing Methods 0.000 claims description 2
- 238000007670 refining Methods 0.000 claims 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims 1
- 238000000926 separation method Methods 0.000 description 16
- 238000005406 washing Methods 0.000 description 14
- 150000002500 ions Chemical class 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 10
- 238000000746 purification Methods 0.000 description 9
- 239000003463 adsorbent Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000001993 wax Substances 0.000 description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- 238000004140 cleaning Methods 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 238000002336 sorption--desorption measurement Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- -1 polycyclic aromatic compounds Chemical class 0.000 description 2
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- ZGUGWUXLJSTTMA-UHFFFAOYSA-N Promazinum Chemical compound C1=CC=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZGUGWUXLJSTTMA-UHFFFAOYSA-N 0.000 description 1
- 241000208422 Rhododendron Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J47/00—Ion-exchange processes in general; Apparatus therefor
- B01J47/014—Ion-exchange processes in general; Apparatus therefor in which the adsorbent properties of the ion-exchanger are involved, e.g. recovery of proteins or other high-molecular compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G25/00—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents
- C10G25/02—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents with ion-exchange material
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Analytical Chemistry (AREA)
- Water Supply & Treatment (AREA)
- General Chemical & Material Sciences (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2550903.9 | 1975-11-13 | ||
| DE2550903A DE2550903C3 (de) | 1975-11-13 | 1975-11-13 | Verfahren zur quantitativen Abtrennung von ungesättigten Verbindungen aus flüssigen Kohlenwasserstoff gemischen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5262203A JPS5262203A (en) | 1977-05-23 |
| JPS6032605B2 true JPS6032605B2 (ja) | 1985-07-29 |
Family
ID=5961611
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51136164A Expired JPS6032605B2 (ja) | 1975-11-13 | 1976-11-12 | 液状パラフイン系炭化水素混合物から不飽和化合物を実際に大量に分離する方法 |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS6032605B2 (enExample) |
| BE (1) | BE848392R (enExample) |
| DE (1) | DE2550903C3 (enExample) |
| FR (1) | FR2331538A2 (enExample) |
| GB (1) | GB1506990A (enExample) |
| NL (1) | NL7612632A (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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. |
| US5220102A (en) * | 1991-12-23 | 1993-06-15 | Uop | Process for separating normal olefins from non-normal olefins |
| CN110252269A (zh) * | 2019-06-13 | 2019-09-20 | 江苏南大环保科技有限公司 | 一种用于处理含有高沸物废水的树脂再生方法 |
| CN110252268A (zh) * | 2019-06-13 | 2019-09-20 | 江苏南大环保科技有限公司 | 一种氯苯生产废水吸附树脂的再生方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3409691A (en) * | 1966-02-01 | 1968-11-05 | Dow Chemical Co | Porous cation exchange resins as selective sorbents in organic systems |
| DE2364333C3 (de) * | 1973-12-22 | 1979-10-11 | Deutsche Texaco Ag, 2000 Hamburg | Verfahren zur Abtrennung von aromatischen Kohlenwasserstoffen aus n-Paraffingemischen durch Behandlung mit einem wasserfreien makroporösen Kationenaustauscherharz |
-
1975
- 1975-11-13 DE DE2550903A patent/DE2550903C3/de not_active Expired
-
1976
- 1976-11-12 JP JP51136164A patent/JPS6032605B2/ja not_active Expired
- 1976-11-12 NL NL7612632A patent/NL7612632A/xx not_active Application Discontinuation
- 1976-11-12 GB GB47273/76A patent/GB1506990A/en not_active Expired
- 1976-11-15 FR FR7634360A patent/FR2331538A2/fr active Granted
- 1976-11-16 BE BE172406A patent/BE848392R/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| BE848392R (fr) | 1977-05-16 |
| DE2550903B2 (de) | 1977-09-15 |
| DE2550903C3 (de) | 1978-05-24 |
| NL7612632A (nl) | 1977-05-17 |
| DE2550903A1 (de) | 1977-05-26 |
| JPS5262203A (en) | 1977-05-23 |
| GB1506990A (en) | 1978-04-12 |
| FR2331538B2 (enExample) | 1982-10-08 |
| FR2331538A2 (fr) | 1977-06-10 |
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