GB1236703A - Surface active agents and compositions containing the same - Google Patents
Surface active agents and compositions containing the sameInfo
- Publication number
- GB1236703A GB1236703A GB1182169A GB1182169A GB1236703A GB 1236703 A GB1236703 A GB 1236703A GB 1182169 A GB1182169 A GB 1182169A GB 1182169 A GB1182169 A GB 1182169A GB 1236703 A GB1236703 A GB 1236703A
- Authority
- GB
- United Kingdom
- Prior art keywords
- internal
- vicinal
- epoxide
- mixtures
- isomerized
- 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
- 239000000203 mixture Substances 0.000 title abstract 10
- 239000004094 surface-active agent Substances 0.000 title 1
- 150000002924 oxiranes Chemical class 0.000 abstract 10
- 150000002009 diols Chemical group 0.000 abstract 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 4
- 150000001336 alkenes Chemical class 0.000 abstract 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract 3
- 238000002360 preparation method Methods 0.000 abstract 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 abstract 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000007859 condensation product Substances 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical group O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- 239000004711 α-olefin Substances 0.000 abstract 2
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 abstract 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 abstract 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical group CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- -1 amino alcohol salt Chemical group 0.000 abstract 1
- 150000001414 amino alcohols Chemical class 0.000 abstract 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical group N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 abstract 1
- YOTZYFSGUCFUKA-UHFFFAOYSA-N dimethylphosphine Chemical compound CPC YOTZYFSGUCFUKA-UHFFFAOYSA-N 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 230000003472 neutralizing effect Effects 0.000 abstract 1
- 230000020477 pH reduction Effects 0.000 abstract 1
- PXBGQFYGVFUKNE-UHFFFAOYSA-N phosphanium;acetate Chemical compound [PH4+].CC([O-])=O PXBGQFYGVFUKNE-UHFFFAOYSA-N 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/23—Rearrangement of carbon-to-carbon unsaturated bonds
- C07C5/25—Migration of carbon-to-carbon double bonds
- C07C5/2506—Catalytic processes
- C07C5/2562—Catalytic processes with hydrides or organic compounds
- C07C5/2568—Catalytic processes with hydrides or organic compounds with ion-exchange resins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D331/00—Heterocyclic compounds containing rings of less than five members, having one sulfur atom as the only ring hetero atom
- C07D331/02—Three-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L1/00—Liquid carbonaceous fuels
- C10L1/10—Liquid carbonaceous fuels containing additives
- C10L1/14—Organic compounds
- C10L1/22—Organic compounds containing nitrogen
- C10L1/222—Organic compounds containing nitrogen containing at least one carbon-to-nitrogen single bond
- C10L1/224—Amides; Imides carboxylic acid amides, imides
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/34—Derivatives of acids of phosphorus
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/79—Phosphine oxides
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/825—Mixtures of compounds all of which are non-ionic
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/32—Amides; Substituted amides
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Detergent Compositions (AREA)
Abstract
1,236,703. Vicinal diols and derivatives. MONSANTO CO. 5 March, 1969 [5 March, 1968], No. 11821/69. Heading C2C. [Also in Division C5] Individual C 14-20 α-olefins are isomerized to mixtures of internal C 14-20 olefins, thereafter reacted with formic acid and hydrogen peroxide to form the internal isomeric vicinal diols, and then ethoxylated by reacting with 5-6 moles of ethylene oxide. Mixtures of individual C 14-20 α-olefins may be converted to mixtures of ethoxylated vicinal diols in the same way and in addition mixtures of individual C 14-20 internal isomeric vicinal diols may also be ethoxylated. The C 14 internal vicinal diolethylene oxide condensation product (5E.O), and mixtures of C 15-20 internal vicinal diolethylene oxide condensation products obtained by blending mixtures of individual vicinal diols may thereafter be sulphated by heating at 120-125‹ C. with sulphamic acid after neutralizing the excess acid with ethanolamine. Isomerized C 14 internal olefin and a mixture of isomerized C 15-20 internal olefins are converted to their epoxides by reacting with peracetic acid at 20‹ C. for 2 days, extracting the organic product, and thereafter fractionating. The epoxides are then reacted with dimethylamine to obtain the amino alcohol which is converted to the salt by neutralization with sulphuric acid. The preparation of the vicinal amino alcohol salt using 3,4-C 14 internal olefin and 5,6-C 15 internal olefin is also described. Alternatively the C 14 isomeric internal epoxide or mixture of isomerized C 15-20 internal epoxide are converted to the episulphide by reacting with thiourea, reacted with methyl sulphide in the presence of boron trifluoride etherate which produces after acidification the isomeric internal vicinal methyl sulphoxide and sulphonate. This method of preparation using 3,4-C 14 internal epoxide and 6,7-C 15 internal epoxide is also described. Alternatively the C 14 isomeric internal epoxide or mixture of isomerized C 15-20 internal epoxide are added to a solution of dimethyl phosphine and sodium in THF. After stirring glacial acetic acid is added thereby obtaining the phosphine acetate which is then reacted with hydrogen peroxide. The residue after removal of water was dissolved in methanolic KOH and refluxed thus producing the internal vicinal hydroxy phosphine oxide. The preparation of the vicinal hydroxy phosphine oxide using 5,6-C 14 internal epoxide and 5,6-C 16 internal epoxide is also described.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71064468A | 1968-03-05 | 1968-03-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1236703A true GB1236703A (en) | 1971-06-23 |
Family
ID=24854924
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1182169A Expired GB1236703A (en) | 1968-03-05 | 1969-03-05 | Surface active agents and compositions containing the same |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE729285A (en) |
| DE (1) | DE1910765A1 (en) |
| FR (1) | FR2003231A1 (en) |
| GB (1) | GB1236703A (en) |
| NL (1) | NL6903338A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4170655A (en) | 1976-09-01 | 1979-10-09 | Henkel Kommanditgesellschaft Auf Aktien | Stable aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils or drugs containing hydroxyalkyl ester- or N-(hydroxyalkyl) amide-ethoxylates |
| US4186207A (en) | 1976-09-01 | 1980-01-29 | Henkel Kommanditgesellschaft Auf Aktien | Stable aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils or drugs containing N-(hydroxyalkyl)amide-ethoxylates |
| WO2022114209A1 (en) | 2020-11-30 | 2022-06-02 | 花王株式会社 | Compound, precursor compound thereof, surfactant composition and detergent composition |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3758410A (en) * | 1968-03-05 | 1973-09-11 | Monsanto Co | Vicinal substituted alkanes |
| DE2226988A1 (en) * | 1972-06-02 | 1973-12-20 | Henkel & Cie Gmbh | DISHWASHER AND CLEANING AGENTS |
| DE2644542A1 (en) * | 1976-10-01 | 1978-04-06 | Henkel Kgaa | RINSE AGENT FOR MACHINE DISH WASHING |
| DE2731218A1 (en) * | 1977-07-11 | 1979-02-01 | Henkel Kgaa | STABLE AQUATIC OR Aqueous-ALCOHOLIC SOLUTIONS OF FAT-SOLUBLE PERFUME OILS |
| GB8704240D0 (en) * | 1987-02-24 | 1987-04-01 | Albright & Wilson | Phosphine oxides |
| DE3723354A1 (en) * | 1987-07-15 | 1989-01-26 | Henkel Kgaa | SULFATED HYDROXY MIXERS, METHOD FOR THEIR PRODUCTION AND THEIR USE |
| DE3743366A1 (en) * | 1987-12-21 | 1989-07-06 | Schmidt Manfred | Thermal roller blind with lateral magnetic-strip guidance |
-
1969
- 1969-02-28 FR FR6905438A patent/FR2003231A1/fr not_active Withdrawn
- 1969-03-03 DE DE19691910765 patent/DE1910765A1/en active Pending
- 1969-03-03 BE BE729285D patent/BE729285A/xx not_active Expired
- 1969-03-04 NL NL6903338A patent/NL6903338A/xx unknown
- 1969-03-05 GB GB1182169A patent/GB1236703A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4170655A (en) | 1976-09-01 | 1979-10-09 | Henkel Kommanditgesellschaft Auf Aktien | Stable aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils or drugs containing hydroxyalkyl ester- or N-(hydroxyalkyl) amide-ethoxylates |
| US4186207A (en) | 1976-09-01 | 1980-01-29 | Henkel Kommanditgesellschaft Auf Aktien | Stable aqueous or aqueous-alcoholic solutions of fat-soluble perfume oils or drugs containing N-(hydroxyalkyl)amide-ethoxylates |
| WO2022114209A1 (en) | 2020-11-30 | 2022-06-02 | 花王株式会社 | Compound, precursor compound thereof, surfactant composition and detergent composition |
| EP4253357A4 (en) * | 2020-11-30 | 2024-06-05 | Kao Corporation | Compound, precursor compound thereof, surfactant composition and detergent composition |
Also Published As
| Publication number | Publication date |
|---|---|
| BE729285A (en) | 1969-09-03 |
| DE1910765A1 (en) | 1969-10-09 |
| FR2003231A1 (en) | 1969-11-07 |
| NL6903338A (en) | 1969-09-09 |
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