IE42004B1 - Production of alkysulphonates - Google Patents
Production of alkysulphonatesInfo
- Publication number
- IE42004B1 IE42004B1 IE2545/74A IE254574A IE42004B1 IE 42004 B1 IE42004 B1 IE 42004B1 IE 2545/74 A IE2545/74 A IE 2545/74A IE 254574 A IE254574 A IE 254574A IE 42004 B1 IE42004 B1 IE 42004B1
- Authority
- IE
- Ireland
- Prior art keywords
- process according
- bisulphite
- alkali metal
- approximately
- transition metal
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 35
- 150000001336 alkenes Chemical class 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 239000001301 oxygen Substances 0.000 claims abstract description 12
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 229910052742 iron Inorganic materials 0.000 claims abstract description 5
- 229910052748 manganese Inorganic materials 0.000 claims abstract description 5
- 239000002904 solvent Substances 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 229910052802 copper Inorganic materials 0.000 claims abstract description 3
- 239000003599 detergent Substances 0.000 claims abstract description 3
- 229910052751 metal Inorganic materials 0.000 claims abstract description 3
- 239000002184 metal Substances 0.000 claims abstract description 3
- 150000002739 metals Chemical class 0.000 claims abstract description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
- 150000003623 transition metal compounds Chemical class 0.000 claims description 10
- ZETCGWYACBNPIH-UHFFFAOYSA-N azane;sulfurous acid Chemical compound N.OS(O)=O ZETCGWYACBNPIH-UHFFFAOYSA-N 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 239000011877 solvent mixture Substances 0.000 claims description 6
- 229910052723 transition metal Inorganic materials 0.000 claims description 5
- 150000003624 transition metals Chemical class 0.000 claims description 5
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims description 3
- 239000008246 gaseous mixture Substances 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 239000000908 ammonium hydroxide Substances 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 2
- 241000282320 Panthera leo Species 0.000 claims 1
- 150000002736 metal compounds Chemical class 0.000 claims 1
- 235000010269 sulphur dioxide Nutrition 0.000 claims 1
- 239000004291 sulphur dioxide Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 238000009472 formulation Methods 0.000 abstract 1
- 239000007789 gas Substances 0.000 abstract 1
- 239000003999 initiator Substances 0.000 abstract 1
- 229910001428 transition metal ion Inorganic materials 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 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)
Abstract
A novel process for the production of alkylsulphonate compounds is described. In this process, an olefin having a carbon atom number of less than 10 is reacted in a solvent with a bisulphite of an alkali metal. This solvent consists of a mixture of water and at least one alcohol. The reaction proceeds in the presence of oxygen or of an oxygen-containing gas. An initiator is necessary which consists of a transition metal ion, selected from the group comprising the metals of groups I, VII and VIII, preferably from Cu, Mn, Fe and Co. In the above process, yields are virtually quantitative. The compounds obtained can be used in detergent formulations.
Description
This invention, relates to a process for producing ammonium or alkali metal alkyl-sulphonates, which are useful in detergent compositions for instance as wetting agents.
The Complete Specification of our Patent to which the present application is one for a Patent of Addition, describes and claims a process for producing a sulphonate, which comprises reacting at least one olefin with ammonium bisulphite or an alkali metal bisulphite in a solvent medium including water and an alcohol, in the presence of oxygen or a gaseous mixture including oxygen and in the presence of a transition metal compound as promoter, and at a pH in the range from 2 to 8.5 with the proviso that when the reaction is effected at a temperature below 60°C. the pH is in the range from 5.5 to 8.5.
According to the present invention, there is provided a process for producing a sulphonate, which comprises reacting at least one primary olefin containing less than 10 carbon atoms with ammonium bisulphite or an alkali metal bisulphate, in a solvent medium including water and an alcohol, in the presence of oxygen or a gaseous mixture including oxygen and in the presence of a transition metal compound as promoter.
The process of the present invention can be carried or out in a continuous/batch operation.
-242004
The primary olefins employed in the process of the present invention can be linear or branched. Examples of suitable olefins are oct-l-ene and hex-l-ene.
Preferably the transition metal of the transition metal compound is selected from the metals belonging to Groups I, VII and VIII of the Periodic Table. More preferably the transition metal is Cu, Fe, Mn or Co. The transition metal compound can be a salt or oxide,; it is preferred to use an oxide of Fe or Mn, for example FegOg, MnOg or Mn^O^.
Preferably the transition metal compound is -4 -2 present in a concentration of from 10 to 10 mole per litre of reaction mixture. More preferably the transition metal compound is present in a concentration of approximately _g mole per litre of reaction mixture.
Advantages are shown by the use of MnOg, since it is soluble in bisulphite solutions and can be recovered quantitatively, by means of filtration, as MngO^ when, at the end of the reaction, the reaction is neutralized under a weak air stream.
Preferably the molar ratio of the ammonium bisulphite or alkali metal bisulphite: the olefin is less (less than 1):1. More preferably the molar ratio of the ammonium bisulphite or alkali metal bisulphite: the olefin is approximately 0.8: 1.
Preferably the ratio by weight of alcohol to water in the solvent mixture is in the range from 1.2:1 to 2.5:1.
More preferably the ratio by weight of alcohol to water in the solvent mixture is approximately 1.9:1.
-342004
Alternatively, it is preferred, when the alcohol is isopropyl alcohol, lor the ratio by volume of isopropyl alcohol to water to be approximately 3.5: 1.5.
Preferably the ratio by weight of solvent mixture to primary olefin is in the range from 6:1 to 3:1.
During the reaction, the temperature is preferably kept below the boiling point of water, i.e. less than 100°C, and, for this purpose, use can be made of superatmospheric pressure in order to keep the system in the liquid phase; when the alcohol and water give rise to an azeotropic mixture, the operation may be carried out at the boiling point of the same.
In the case of isopropyl alcohol, the process is preferably carried out at 80°C which is the boiling point of the wateralcohol azeotropic mixture. Use is preferably made of the temperature range from 20 to 90°C, more preferably approximately 80 °C.
An air or oxygen flow is preferably such as to maintain a flow equal to approximately 0.8 litre of oxygen per litre of reaction mixture per hour. The pH is preferably maintained at approximately about 6, but the reaction generally proceeds well at a pH in the range from 8.5 to 2.
Throughout the reaction, good stirring should be adopted in order to allow the emulsification of the olefin. Bisulphite may be formed in situ by reaction SOg and ammonium hydroxide or alkali metal hydroxide.
Other operating conditions are disclosed in the complete specification of the main application.
-442004
The following Examples are intended to show the effectiveness of the use of a transition metal catalyst in those reactions starting with an olefin having less than 10 carbon atoms, which, as it is known, have a high degree of inertia towards this type of reaction. Examples 1 and 3 are included for comparative purposes.
EXAMPLE 1
1.20 Grams of NagSgO,- (corresponding to 1.2 moles of NaIISO,p were dissolved in 700 cc of isopropyl alcohol and 300 cc of water in a glass reactor equipped with a stirrer, a Teflon anti-slosh baffle, glass electrode, air bubbler, a charging funnel and a reflux condenser; 200 cc (1.6 moles) of hexene-1 were added and the resulting mixture was buffered by NaOH at pH of 5.5; the mixture was brought to 60°C on a thermostatic bath and air was then bubbled through the mixture at a rate of 4 litres per hour, the bisulphite disappearance was followed iodometrically. The reaction was over after 50 minutes. 160 Grams of dry product were isolated containing 10.5% by weight of Na2SO4· Productivity was equal to 160 Grams per hour per litre.
EXAMPLE 2
The preceding test was repeated but this time it was carried out in the presence of 200 mg of MnOg The reaction was over in 20 minutes 197 Grams of dry product were isolated containing 5.2% by weight Na2SO4. Productivity was equal to 492 Grams per hour per litre.
-542004
EXAMPLE 3
The procedure of Example 1 was repeated, except that tho olefin used was octene-1.
The reaction was over in 55 minutes and 175.5 g of dry product were isolaLed containing 11.7% of NagSO^.
Productivity was equal to 160 Grams per hour per litre.
EXAMPLE 4
The procedure of Example 3 was repeated but this time it was carried out in the presence of 200 mg of
MnOg. The reaction was over in 20 minutes and 205 g of dry product were isolated containing 4.7% by weight of Na2S0^. Productivity was equal 615 Grams per hour per litre.
Claims (23)
1. What we claim is:1. A process for producing a sulphonate:, which comprises reacting at least one primary olefin containing less than 10 carbon atoms with ammonium bisulphite or an 5 alkali metal bisulphite, in a solvent medium including water and an alcohol, in the presence of oxygen or a gaseous mixture including oxygen and in the presence of a transition metal compound as promoter.
2. A process according to claim 1, wherein the 10 transition metal of the transition metal compound is selected from the metals belonging to Groups I, VII and VIII of the Periodic Table. 3. A process according to claim 2, wherein the transition metal is Cu, Mn, Fe or Co. 15 4. A process according to claim 3, wherein the transition metal compound is an oxide of Mn or Fe.
3. 5. A process according to any preceding claim, wherein the transition metal compound is present in a con-4 -2 centration of from 10 to 10 mole per litre of reaction mixture. -743004 G. Λ process according Lo claim 5, wherein Lhe l.ransi Lion metal compound is present in a concentration of -3 approximately 10 mole per litre of reaction mixture.
4. 7. A process according to any preceding claim, 5 wherein the molar ratio of the ammonium bisulphite or alkali metal bisulphite: the olefin is (less than 1):1.
5. 8. A process according to claim 7, wherein the molar ratio of the ammonium bisulphite or alkali metal bisulphite: the olefin is approximately 0.8: 1. 10
6. 9. A process according to any preceding claim, wherein the ratio by weight of alcohol to water in the solvent mixture is in the range from 1.2:1 to 2.5:1.
7. 10. A process according to claim 9, wherein the ratio by weight of alcohol to water in the solvent mixture is approxi15 mately 1.9:1.
8. 11. A process according to any one of Claims 1 to 8, wherein the alcohol is isopropyl alcohol.
9. 12. A process according to claim 11, wherein the ratio by voluine of isopropyl alcohol to water is approximately -8420 0 4
10. 13. A process according to any preceding claim, wherein the temperature during the reaction is less than 100 °C
11. 14. A process according to claim 13, wherein the temperature is in the range from 20 to 90 °C.
12. 15. A process according to claim 14, wherein Lhe temperature is approximately 80°C.
13. 16. A process according to any preceding claim, wherein the ratio by weight of solvent mixture to primary olefin is in the range from 6:1 to 3:1.
14. 17. A process according to any preceding claim, wherein oxygen is introduced into the reaction mixture at a rate of approximately 0.8 litre of oxygen per litre of reaction mixture per hour.
15. 18. A process according to any preceding claim, wherein the pH of the reaction mixture is in the range from 2 to 8.5.
16. 19. A process according to claim 18, wherein the pH is approximately 6.0.
17. 20. A process according to any preceding claim, wherein the ammonium bisulphite or alkali metal bisulphite is prepared in situ by reacting sulphur dioxide and ammonium hydroxide or an alkali metal hydroxide. -942004
18. 21. Λ process according Lo any preceding claim, wherein Lhe primary olefin is reacted with ammonium bisulphite
19. 22. A procoss substantially as described in either of the foregoing Examples 2 and 4.
20. 23. An alkali metal alkylsulphonate whenever produced by a process according to any one of claims 1 to 20 and 22.
21. 24. An ammonium alkylsulphonate whenever produced by a process according to claim 21.
22. 25. A di(alkali metal)alkylene-l,2-disulphonate whenever produced by a process according to any one of claims 1 to 20 and 22.
23. 26. A detergent composition which includes an alkylsulphonate as claimed in any one of claims 23 to 25.
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 (2)
| Publication Number | Publication Date |
|---|---|
| IE42004L IE42004L (en) | 1975-06-20 |
| IE42004B1 true IE42004B1 (en) | 1980-05-21 |
Family
ID=11287340
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2545/74A IE42004B1 (en) | 1973-12-20 | 1974-12-10 | Production of alkysulphonates |
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 NO NO744593A patent/NO744593L/no unknown
- 1974-12-19 ES ES433563A patent/ES433563A2/en not_active Expired
- 1974-12-19 CA CA216,436A patent/CA1024161A/en not_active Expired
- 1974-12-19 DE DE19742460246 patent/DE2460246A1/en not_active Withdrawn
- 1974-12-19 SE SE7416079A patent/SE7416079L/xx unknown
- 1974-12-20 JP JP49145852A patent/JPS5095224A/ja active Pending
- 1974-12-20 NL NL7416738A patent/NL7416738A/en active Search and Examination
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5095224A (en) | 1975-07-29 |
| DE2460246A1 (en) | 1975-06-26 |
| CA1024161A (en) | 1978-01-10 |
| FR2324623A1 (en) | 1977-04-15 |
| CH613943A5 (en) | 1979-10-31 |
| NL7416738A (en) | 1975-06-24 |
| NO744593L (en) | 1975-07-14 |
| FR2324623B1 (en) | 1978-05-19 |
| DK660674A (en) | 1975-08-25 |
| IE42004L (en) | 1975-06-20 |
| IT1045798B (en) | 1980-06-10 |
| ES433563A2 (en) | 1977-03-16 |
| BE823394A (en) | 1975-04-16 |
| AU7593674A (en) | 1976-06-03 |
| ZA747894B (en) | 1975-12-31 |
| GB1481187A (en) | 1977-07-27 |
| SE7416079L (en) | 1975-06-23 |
| LU71508A1 (en) | 1975-06-17 |
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