DE2612723A1 - Zweistufenverfahren zur extremreinigung von rohsulfonsaeuren - Google Patents
Zweistufenverfahren zur extremreinigung von rohsulfonsaeurenInfo
- Publication number
- DE2612723A1 DE2612723A1 DE19762612723 DE2612723A DE2612723A1 DE 2612723 A1 DE2612723 A1 DE 2612723A1 DE 19762612723 DE19762612723 DE 19762612723 DE 2612723 A DE2612723 A DE 2612723A DE 2612723 A1 DE2612723 A1 DE 2612723A1
- Authority
- DE
- Germany
- Prior art keywords
- hexane
- acids
- solution
- acid
- process step
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 98
- 239000002253 acid Substances 0.000 title claims description 57
- 150000007513 acids Chemical class 0.000 title claims description 33
- 238000000746 purification Methods 0.000 title description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 219
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 120
- 150000003460 sulfonic acids Chemical class 0.000 claims description 57
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 54
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 claims description 54
- 239000003921 oil Substances 0.000 claims description 47
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 45
- 239000004215 Carbon black (E152) Substances 0.000 claims description 39
- 229930195733 hydrocarbon Natural products 0.000 claims description 39
- 150000002430 hydrocarbons Chemical class 0.000 claims description 39
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 27
- 235000011132 calcium sulphate Nutrition 0.000 claims description 27
- 239000000047 product Substances 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- -1 alkyl aromatic sulfonic acids Chemical class 0.000 claims description 21
- 239000010687 lubricating oil Substances 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 11
- 238000007664 blowing Methods 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 239000002002 slurry Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000001175 calcium sulphate Substances 0.000 claims description 5
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 3
- 238000004140 cleaning Methods 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000008107 benzenesulfonic acids Chemical class 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims 5
- 238000001704 evaporation Methods 0.000 claims 5
- 239000003085 diluting agent Substances 0.000 claims 4
- JCXCVQBEOOXYNZ-UHFFFAOYSA-J dicalcium;carbonate;sulfate Chemical compound [Ca+2].[Ca+2].[O-]C([O-])=O.[O-]S([O-])(=O)=O JCXCVQBEOOXYNZ-UHFFFAOYSA-J 0.000 claims 1
- 239000000314 lubricant Substances 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 19
- 238000001914 filtration Methods 0.000 description 13
- 229920001577 copolymer Polymers 0.000 description 12
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 11
- 238000010586 diagram Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 8
- 239000000292 calcium oxide Substances 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 5
- 238000005119 centrifugation Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 3
- 239000000395 magnesium oxide Substances 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011269 tar Substances 0.000 description 2
- SKBCAPJNQFFBCQ-UHFFFAOYSA-N 2-methylprop-1-ene prop-1-ene Chemical group CC=C.CC(C)=C SKBCAPJNQFFBCQ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- ILFFFKFZHRGICY-UHFFFAOYSA-N anthracene-1-sulfonic acid Chemical class C1=CC=C2C=C3C(S(=O)(=O)O)=CC=CC3=CC2=C1 ILFFFKFZHRGICY-UHFFFAOYSA-N 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- FLIBMGVZWTZQOM-UHFFFAOYSA-N benzene;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC=CC=C1 FLIBMGVZWTZQOM-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229940043430 calcium compound Drugs 0.000 description 1
- 150000001674 calcium compounds Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229940082150 encore Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56288775A | 1975-03-28 | 1975-03-28 | |
| US66297576A | 1976-03-01 | 1976-03-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2612723A1 true DE2612723A1 (de) | 1976-10-07 |
Family
ID=27073107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762612723 Withdrawn DE2612723A1 (de) | 1975-03-28 | 1976-03-25 | Zweistufenverfahren zur extremreinigung von rohsulfonsaeuren |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS51118723A (enExample) |
| DE (1) | DE2612723A1 (enExample) |
| FR (1) | FR2305429A1 (enExample) |
| GB (1) | GB1530664A (enExample) |
| IT (1) | IT1057356B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2796941B1 (fr) * | 1999-07-27 | 2001-09-14 | Atofina | Purification d'acides alcanesulfoniques |
-
1976
- 1976-03-25 DE DE19762612723 patent/DE2612723A1/de not_active Withdrawn
- 1976-03-26 IT IT4874876A patent/IT1057356B/it active
- 1976-03-26 JP JP3343776A patent/JPS51118723A/ja active Pending
- 1976-03-26 FR FR7608973A patent/FR2305429A1/fr active Granted
- 1976-03-26 GB GB1226776A patent/GB1530664A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1530664A (en) | 1978-11-01 |
| FR2305429A1 (fr) | 1976-10-22 |
| IT1057356B (it) | 1982-03-10 |
| JPS51118723A (en) | 1976-10-18 |
| FR2305429B1 (enExample) | 1979-05-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |