CA1131247A - Sulfonation of alkylated aromatic hydrocarbons - Google Patents
Sulfonation of alkylated aromatic hydrocarbonsInfo
- Publication number
- CA1131247A CA1131247A CA327,572A CA327572A CA1131247A CA 1131247 A CA1131247 A CA 1131247A CA 327572 A CA327572 A CA 327572A CA 1131247 A CA1131247 A CA 1131247A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- recited
- sulfonic acid
- liquid
- alkylated aromatic
- 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
- 150000004945 aromatic hydrocarbons Chemical class 0.000 title claims abstract description 25
- 238000006277 sulfonation reaction Methods 0.000 title abstract description 21
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 26
- 239000011541 reaction mixture Substances 0.000 claims abstract description 14
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 11
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 11
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 9
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 62
- 239000007788 liquid Substances 0.000 claims description 51
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 37
- 230000008569 process Effects 0.000 claims description 25
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 22
- 150000004996 alkyl benzenes Chemical class 0.000 claims description 18
- 238000010791 quenching Methods 0.000 claims description 18
- 230000000171 quenching effect Effects 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 235000011054 acetic acid Nutrition 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 10
- 230000002829 reductive effect Effects 0.000 claims description 10
- 230000029087 digestion Effects 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 8
- 150000001735 carboxylic acids Chemical class 0.000 claims description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 7
- -1 alkali metal sulfonate Chemical class 0.000 claims description 7
- 239000002245 particle Substances 0.000 claims description 7
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 6
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 5
- 235000019260 propionic acid Nutrition 0.000 claims description 5
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 229910052936 alkali metal sulfate Inorganic materials 0.000 claims description 4
- 235000010233 benzoic acid Nutrition 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 229960002446 octanoic acid Drugs 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- 229940005605 valeric acid Drugs 0.000 claims description 3
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 239000012259 ether extract Substances 0.000 claims description 2
- 238000004448 titration Methods 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- 230000000977 initiatory effect Effects 0.000 claims 1
- 238000004064 recycling Methods 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 20
- 239000007795 chemical reaction product Substances 0.000 abstract description 16
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 15
- 235000011149 sulphuric acid Nutrition 0.000 abstract description 2
- 239000000376 reactant Substances 0.000 description 17
- 238000011144 upstream manufacturing Methods 0.000 description 10
- 150000003457 sulfones Chemical class 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- 238000006731 degradation reaction Methods 0.000 description 5
- 239000010419 fine particle Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 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
- 239000000110 cooling liquid Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000000889 atomisation Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N benzyl-alpha-carboxylic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000000779 depleting effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002691 malonic acids Chemical class 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical class OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 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
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/06—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with sulfuric acid or sulfur trioxide
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91453578A | 1978-06-12 | 1978-06-12 | |
| US914,535 | 1978-06-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1131247A true CA1131247A (en) | 1982-09-07 |
Family
ID=25434489
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA327,572A Expired CA1131247A (en) | 1978-06-12 | 1979-05-14 | Sulfonation of alkylated aromatic hydrocarbons |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS59502B2 (it) |
| CA (1) | CA1131247A (it) |
| DE (1) | DE2923510A1 (it) |
| GB (1) | GB2023138B (it) |
| IT (1) | IT1118773B (it) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7968742B2 (en) | 2005-12-20 | 2011-06-28 | The Chemithon Corporation | Method and device for the sulfonation or sulfation of sulfonatable or sulfatable organic substances and for performing faster, strongly exothermic gas/liquid reactions |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5480900A (en) * | 1977-12-03 | 1979-06-27 | Asahi Chemical Ind | Method and apparatus for preserving live fish and shellfish for long period at high density |
| GB2155474A (en) * | 1984-03-13 | 1985-09-25 | Procter & Gamble | Process for the continuous reaction of organic compounds with sulfur trioxide |
| JP2625562B2 (ja) * | 1990-01-22 | 1997-07-02 | 三菱電機株式会社 | 飼育装置 |
| WO2010062605A1 (en) * | 2008-10-27 | 2010-06-03 | Stepan Company | Alkylaryl sulfonates with reduced sulfone levels and methods for their preparation |
| CN101423482B (zh) * | 2008-11-27 | 2012-07-25 | 中国日用化学工业研究院 | 一种磺化中和反应一体化的方法 |
| JP5606358B2 (ja) | 2011-02-24 | 2014-10-15 | 三菱重工業株式会社 | インペラ及びこれを備えたロータ並びにインペラの製造方法 |
| JP2013047479A (ja) | 2011-08-29 | 2013-03-07 | Mitsubishi Heavy Ind Ltd | インペラ及びこれを備えた回転機械並びにインペラの製造方法 |
| JP5907723B2 (ja) | 2011-12-26 | 2016-04-26 | 三菱重工業株式会社 | 回転機械の製造方法 |
| CN103566839B (zh) * | 2012-07-26 | 2015-10-28 | 中国石油天然气股份有限公司 | 可调式下喷雾膜磺化反应器及其应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2704295A (en) * | 1952-07-11 | 1955-03-15 | Allied Chem & Dye Corp | Aromatic hydrocarbon sulfonation |
| US2831020A (en) * | 1954-09-03 | 1958-04-15 | Tennessee Corp | Processes for producing anhydrous aromatic sulfonic acids with low sulfone content and the products thereof |
| US3427342A (en) * | 1962-12-12 | 1969-02-11 | Chemithon Corp | Continuous sulfonation process |
| US3297748A (en) * | 1963-06-13 | 1967-01-10 | Chevron Res | Alkylbenzene sulfonate color and odor inhibition |
| JPS5531059A (en) * | 1978-10-18 | 1980-03-05 | Toyo Soda Mfg Co Ltd | Preparation of alkali metal p-styrenesulfonate |
-
1979
- 1979-05-14 CA CA327,572A patent/CA1131247A/en not_active Expired
- 1979-05-24 GB GB7918150A patent/GB2023138B/en not_active Expired
- 1979-06-09 DE DE19792923510 patent/DE2923510A1/de active Granted
- 1979-06-11 IT IT68257/79A patent/IT1118773B/it active
- 1979-06-11 JP JP54073443A patent/JPS59502B2/ja not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7968742B2 (en) | 2005-12-20 | 2011-06-28 | The Chemithon Corporation | Method and device for the sulfonation or sulfation of sulfonatable or sulfatable organic substances and for performing faster, strongly exothermic gas/liquid reactions |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2923510C2 (it) | 1989-04-27 |
| DE2923510A1 (de) | 1979-12-20 |
| JPS59502B2 (ja) | 1984-01-07 |
| GB2023138A (en) | 1979-12-28 |
| IT7968257A0 (it) | 1979-06-11 |
| JPS554376A (en) | 1980-01-12 |
| GB2023138B (en) | 1983-02-23 |
| IT1118773B (it) | 1986-03-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |