NO744593L - - Google Patents
Info
- Publication number
- NO744593L NO744593L NO744593A NO744593A NO744593L NO 744593 L NO744593 L NO 744593L NO 744593 A NO744593 A NO 744593A NO 744593 A NO744593 A NO 744593A NO 744593 L NO744593 L NO 744593L
- Authority
- NO
- Norway
- Prior art keywords
- stated
- reaction
- bisulphite
- procedure
- water
- Prior art date
Links
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 150000001336 alkenes Chemical class 0.000 claims description 12
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000012190 activator Substances 0.000 claims description 3
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- 229910001428 transition metal ion Inorganic materials 0.000 claims 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims 1
- -1 alkali metal bisulfite Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- AMWRITDGCCNYAT-UHFFFAOYSA-L manganese oxide Inorganic materials [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 1
- PPNAOCWZXJOHFK-UHFFFAOYSA-N manganese(2+);oxygen(2-) Chemical class [O-2].[Mn+2] PPNAOCWZXJOHFK-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
Den foreliggende oppfinnelse vedrører en fremgangsmåte for fremstilling av alkylsul fonater av alkalimetaller, for anvendelse f.eks. i vaskemidler, fuktemidler o.l., og består i å addere alkalimetall-bisulfitter til terminale olefiniske dobbeltbindinger. The present invention relates to a method for producing alkyl sulphonates of alkali metals, for use e.g. in detergents, wetting agents etc., and consists in adding alkali metal bisulphites to terminal olefinic double bonds.
Det er fra tidligere kjent at det er mulig å addere bisulfitt It is previously known that it is possible to add bisulphite
til primære olefiner ved et hurtig reaksjonssystem, enten diskontinuerlig eller kontinuerlig, fremmet ved hjelp av luft og overgangsmetal1 sal ter. to primary olefins by a rapid reaction system, either discontinuous or continuous, promoted by air and transition metal1 salts.
Tidligere eir det således kjent at langkjedede alkyl sulf onater Previously, it was thus known that long-chain alkyl sulfonates
kan fremstilles ved hjelp av et kontinuerlig eller diskontinuerlig system med ganske kvantitative utbytter og gjennomsnittlige reaksjonstider mindre enn 1 time, ved "en tilsetning av bisulfitt til primære olefiner med fra 10 til 20 karbonatomer, idet reaksjonen fremmes av luft i nærvær av salter eller oksyder av overgangsmetal1 er i gruppene I, VII og VIII i det periodiske system, f.eks. Fe, Mn, Cu, Co o.l. can be prepared by means of a continuous or batch system with fairly quantitative yields and average reaction times less than 1 hour, by "an addition of bisulfite to primary olefins of from 10 to 20 carbon atoms, the reaction being promoted by air in the presence of salts or oxides of transition metal1 is in groups I, VII and VIII of the periodic table, eg Fe, Mn, Cu, Co etc.
Reaksjonen gjennomføres ved å avstemme reaksjonsbetingelsene i forhold til hverandre, dvs. forholdet mellom reaksjonskomponenter, type og mengde av løsningsmiddel, temperatur og pH, slik at sekundære bireaksjoner nedsettes så mye som mulig og spesielt dannelsen av uorganiske salter. The reaction is carried out by coordinating the reaction conditions in relation to each other, i.e. the ratio between reaction components, type and amount of solvent, temperature and pH, so that secondary side reactions are reduced as much as possible and especially the formation of inorganic salts.
Det er nå funnet at det er mulig på lignende måte å fremstille alkalimetallsul fonater fra olefiner, rette eller forgrenete, med et karbonatom-antal 1 lavere enn 10, ved å om,sette,;3olefin med bisulfitt i et løsningsmiddel som utgjøres av vann og alkohol. It has now been found that it is possible to prepare alkali metal sulphonates in a similar way from olefins, straight or branched, with a number of carbon atoms 1 lower than 10, by reacting the 3olefin with bisulphite in a solvent consisting of water and alcohol.
De forskjellige komponenter tilsettes i mengder slik at det opprettholdes et passende olefinoverskudd (NaHSO^/olefin-molforhold lavere enn 1 og foretrukket tilsvarende 0.8) for å. oppnå en total omdannelse av det innførte bisulfitt, et løsningsmiddel/olefin-vektforhold mellom 6/1 og 3/1 og et alkohol/vann-vektforhold mellom 1.2 og 2.5, foretrukket på 1.9. The various components are added in amounts so as to maintain a suitable olefin excess (NaHSO^/olefin molar ratio lower than 1 and preferably corresponding to 0.8) to achieve a total conversion of the introduced bisulphite, a solvent/olefin weight ratio between 6/1 and 3/1 and an alcohol/water weight ratio between 1.2 and 2.5, preferably 1.9.
Under reaksjonsforløpet holdes temperaturen under vannets kokepunkt og for dette formål kan trykk anvendes for å holde.^systemet i ' flytende fase. Når alkohol og vann danner en azeotrop blanding kan operasjonene gjennomføres nettopp ved verdiene for denne. I tilfellet av isopropylalkohol ble det arbeidet ved 80°C som er akkurat koketemperaturen for den azeotrope vann-alkohoi-blanding. Temperaturer i området 20 - 90°C kan også anvendes. During the course of the reaction, the temperature is kept below the boiling point of the water and for this purpose pressure can be used to keep the system in the liquid phase. When alcohol and water form an azeotropic mixture, the operations can be carried out precisely at the values for this. In the case of isopropyl alcohol, it was worked at 80°C, which is exactly the boiling temperature of the azeotropic water-alcohol mixture. Temperatures in the range 20 - 90°C can also be used.
Den metalliske aktivator tilføres i mengder på omtrent 10 — 3 mol/l The metallic activator is added in amounts of approximately 10 - 3 mol/l
og samtidig sendes en ±røm av luft el l-er -oksygen gjennom blandingen for å opprettholde en strøm på omtrent 0.8 l/time beregnet som oksygen. pH foretrekkes holdt ved omtrent 6, men reaksjonen forløper meget bra ved pH fra 8.5 til 2. and at the same time a flow of air or oxygen is sent through the mixture to maintain a flow of approximately 0.8 l/hour calculated as oxygen. The pH is preferably kept at approximately 6, but the reaction proceeds very well at a pH from 8.5 to 2.
Under reaksjonsforløpet må god omrøring opprettholdes for å muliggjøre emulgering av olefinet. Bisulfitt kan dannes in situ ved hjelp av S02og alkali.. During the course of the reaction, good stirring must be maintained to enable emulsification of the olefin. Bisulphite can be formed in situ with the help of SO2 and alkali.
De anvendte aktivatorer er salter eller oksyder av overgangsmetaller, foretrukket jern eller manganoksyder (Fe90~, MnO , Mn^O.)-. The activators used are salts or oxides of transition metals, preferably iron or manganese oxides (Fe90~, MnO, Mn^O.)-.
— 2 — 4 ■ 3-4 ^_ Konsentrasjonsområdene er fra 10 til 10 molar, spesielt 10 . Spesielt gode egenskaper, fremvises av MnC>2, da det er oppløselig — 2 — 4 ■ 3-4 ^_ The concentration ranges are from 10 to 10 molar, especially 10 . Particularly good properties are exhibited by MnC>2, as it is soluble
i bisulfittløsninger og kan gjenvinnes kvantitativt, ved hjelp av en filtrering, som Mn^O^når reaksjonsløsningen ved avsluttet reaksjon. nøytraliseres under en svak luftstrøm. in bisulphite solutions and can be recovered quantitatively, by means of a filtration, as Mn^O^ when the reaction solution is completed. is neutralized under a weak air flow.
I de følgende eksempler skal effektiviteten av den katalysator som anvendes under reaksjonene vises, ved å gå ut fra olefiner med et karbonatom-antall lavere enn 10, idet det vil være kjent- at disse har en høy reaksjonstreghet overfor denne type reaksjoner. In the following examples, the effectiveness of the catalyst used during the reactions will be shown, starting from olefins with a carbon atom number lower than 10, as it will be known that these have a high reaction inertia towards this type of reaction.
EKSEMPEL 1 EXAMPLE 1
120 g Na2S20^(1.2 mol) ble oppløst i 700 cc isopropylalkohol og 300 cc vann i en glassreaktor utstyrt med røreverk og en ledeplate av "teflon" for å hindre avsetninger, glasselektrode, • luft-gjennomboblingsinnretning, dråpetrakt og tilbakeløpskondensator. 120 g of Na2S20^ (1.2 mol) was dissolved in 700 cc of isopropyl alcohol and 300 cc of water in a glass reactor equipped with a stirrer and a "teflon" guide plate to prevent deposits, glass electrode, • air-bubbling device, dropping funnel and reflux condenser.
200 cc (1.6 mol) heksen-1 ble tilført og hele blandingen ble pufret ved hjelp av NaOH ved pH 5.5. Blandingen ble bragt til 60°C ved hjelp av et termostatbad og luft ble gjennomboblet (4 l/time). Bisulfitt-forbruket ble fulgt jodometrisk. Reaksjonen var avsluttet etter 50 minutter. Det ble isolert 160 g tørt produkt inneholdende 10.5 vektprosent Na2S0^. Produksjonskapasiteten tilsvarte 160 g/time.1 200 cc (1.6 mol) hexene-1 was added and the entire mixture was buffered with NaOH at pH 5.5. The mixture was brought to 60°C using a thermostatic bath and air was bubbled through (4 l/hour). Bisulphite consumption was monitored iodometrically. The reaction was complete after 50 minutes. 160 g of dry product containing 10.5% by weight Na2S0^ was isolated. The production capacity corresponded to 160 g/hour.1
EKSEMPEL 2 EXAMPLE 2
Det foregående forsøk ble gjentatt med tilsetning av 200 mg MNC^. Reaksjonen var avsluttet etter 20 minutter. Det ble oppnådd 197 g tørt produkt inneholdende 5.2 vektprosent Na2SG>4<.. Produksjonskapasiteten utgjorde 492 g/time 1. The previous experiment was repeated with the addition of 200 mg of MNC^. The reaction was complete after 20 minutes. 197 g of dry product containing 5.2% by weight of Na2SG>4< was obtained. The production capacity was 492 g/hour 1.
EKSEMPEL 3 EXAMPLE 3
Eksempel 1 ble gjentatt, men olefinet var okten-1. Example 1 was repeated, but the olefin was octene-1.
Reaksjonen var over etter 55 minutter og det ble isolert 175.5 g The reaction was over after 55 minutes and 175.5 g were isolated
tørt produkt inneholdende 11.7% Na2SC>4. Produktiviteten var 160 g/time 1 . dry product containing 11.7% Na2SC>4. The productivity was 160 g/hour 1 .
EKSEMPEL 4 EXAMPLE 4
Fremgangsmåten i eksempel 3 ble fulgt og det ble tilsatt 200 mg MnC^. Reaksjonen var avsluttet etter 20 minutter og det ble isolert 205 g tørt produkt inneholdende 4.7 vek.tprosent Na2SO^. Produktiviteten tilsvarte 615 g/time 1. The procedure in example 3 was followed and 200 mg of MnC 2 was added. The reaction was finished after 20 minutes and 205 g of dry product containing 4.7% by weight of Na2SO4 was isolated. The productivity corresponded to 615 g/hour 1.
Claims (7)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT54487/73A IT1045798B (en) | 1973-12-20 | 1973-12-20 | PROCESS FOR THE PREPARATION OF ALCHYL SULPHONATE COMPOUNDS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO744593L true NO744593L (en) | 1975-07-14 |
Family
ID=11287340
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO744593A NO744593L (en) | 1973-12-20 | 1974-12-19 |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS5095224A (en) |
| BE (1) | BE823394A (en) |
| CA (1) | CA1024161A (en) |
| CH (1) | CH613943A5 (en) |
| DE (1) | DE2460246A1 (en) |
| DK (1) | DK660674A (en) |
| ES (1) | ES433563A2 (en) |
| FR (1) | FR2324623A1 (en) |
| GB (1) | GB1481187A (en) |
| IE (1) | IE42004B1 (en) |
| IT (1) | IT1045798B (en) |
| LU (1) | LU71508A1 (en) |
| NL (1) | NL7416738A (en) |
| NO (1) | NO744593L (en) |
| SE (1) | SE7416079L (en) |
| ZA (1) | ZA747894B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1062556C (en) * | 1997-12-05 | 2001-02-28 | 中国科学院新疆化学研究所 | Process for producing alkyl sulfonate from gas of refinery plant |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3150169A (en) * | 1960-12-30 | 1964-09-22 | California Research Corp | Bisulfite addition using a perester-iron salt initiator |
| US3644499A (en) * | 1968-12-17 | 1972-02-22 | Gulf Research Development Co | Process for preparing detergent sulfonates |
| IT956743B (en) * | 1972-06-21 | 1973-10-10 | Snam Progetti | PROCEDURE FOR THE PREPARATION OF ALKYLSULPHONATED COMPOUNDS |
-
1973
- 1973-12-20 IT IT54487/73A patent/IT1045798B/en active
-
1974
- 1974-12-06 GB GB52940/74A patent/GB1481187A/en not_active Expired
- 1974-12-10 CH CH1640274A patent/CH613943A5/en not_active IP Right Cessation
- 1974-12-10 IE IE2545/74A patent/IE42004B1/en unknown
- 1974-12-11 ZA ZA00747894A patent/ZA747894B/en unknown
- 1974-12-12 FR FR7440981A patent/FR2324623A1/en active Granted
- 1974-12-16 BE BE151540A patent/BE823394A/en unknown
- 1974-12-17 LU LU71508A patent/LU71508A1/xx unknown
- 1974-12-18 DK DK660674A patent/DK660674A/da unknown
- 1974-12-19 ES ES433563A patent/ES433563A2/en not_active Expired
- 1974-12-19 SE SE7416079A patent/SE7416079L/xx unknown
- 1974-12-19 NO NO744593A patent/NO744593L/no unknown
- 1974-12-19 CA CA216,436A patent/CA1024161A/en not_active Expired
- 1974-12-19 DE DE19742460246 patent/DE2460246A1/en not_active Withdrawn
- 1974-12-20 NL NL7416738A patent/NL7416738A/en active Search and Examination
- 1974-12-20 JP JP49145852A patent/JPS5095224A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1481187A (en) | 1977-07-27 |
| ES433563A2 (en) | 1977-03-16 |
| BE823394A (en) | 1975-04-16 |
| LU71508A1 (en) | 1975-06-17 |
| IE42004L (en) | 1975-06-20 |
| FR2324623B1 (en) | 1978-05-19 |
| ZA747894B (en) | 1975-12-31 |
| DK660674A (en) | 1975-08-25 |
| DE2460246A1 (en) | 1975-06-26 |
| NL7416738A (en) | 1975-06-24 |
| IE42004B1 (en) | 1980-05-21 |
| JPS5095224A (en) | 1975-07-29 |
| AU7593674A (en) | 1976-06-03 |
| CH613943A5 (en) | 1979-10-31 |
| CA1024161A (en) | 1978-01-10 |
| FR2324623A1 (en) | 1977-04-15 |
| IT1045798B (en) | 1980-06-10 |
| SE7416079L (en) | 1975-06-23 |
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