US2814613A - Production and/or separation of nonionic surface active agents - Google Patents
Production and/or separation of nonionic surface active agents Download PDFInfo
- Publication number
- US2814613A US2814613A US398206A US39820653A US2814613A US 2814613 A US2814613 A US 2814613A US 398206 A US398206 A US 398206A US 39820653 A US39820653 A US 39820653A US 2814613 A US2814613 A US 2814613A
- Authority
- US
- United States
- Prior art keywords
- surface active
- agent
- active agent
- fraction
- ethylene oxide
- 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 - Lifetime
Links
- 239000004094 surface-active agent Substances 0.000 title claims description 31
- 238000004519 manufacturing process Methods 0.000 title description 4
- 238000000926 separation method Methods 0.000 title description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- 230000001376 precipitating effect Effects 0.000 claims description 14
- 150000001298 alcohols Chemical class 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 239000007788 liquid Substances 0.000 claims description 8
- 239000000194 fatty acid Substances 0.000 claims description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 5
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 5
- 229930195729 fatty acid Natural products 0.000 claims description 5
- 150000004665 fatty acids Chemical class 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 5
- -1 POLY ETHYL OXY Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- 238000005194 fractionation Methods 0.000 claims description 3
- 239000007859 condensation product Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 239000004202 carbamide Substances 0.000 description 6
- 239000013543 active substance Substances 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 3
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 3
- 239000013557 residual solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
Classifications
-
- 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
Definitions
- This invention relates to "animproved' process for-the production and/or separation of 'non-ionicsurface*active agents.
- the surface activeager'it' being only partiallysoluble in 'saidprcipitap in gent an'd said-precipitating agent being-a l'quid ⁇ vhi'ch i :mi'scible"vv' h saidaanvenewhere 'p'art'of said-surface ative agent istlirovvn oufif-soltitibnfandthfieafter recovering the precipitated; fraction.
- the non-ionic surface active agent comprises a mixture of surface active compounds having, in the molecule, ethylene oxide chains diife'ring length
- the fraction precipitated will contain "an increased portion of compounds having-relatively long ethylene oxide -ehains and the remainingsolution will-contaiifi 'a'n increased proportion of compounds havinga relatively short ethylene oxide chain. 7 I N
- the process maybe'operatedjtofgiveaipluralitybfprecipitated fractions, for eampleby progressive additions of the "precipitatingliquid arty iiib'dific'a- 2,814,613 Patented ov. -26 1957 tion of the reaction conditions, as'by progressvely'decreasing'the temperature.
- a process which comprises reacting ethylene oxide with a "suitable-organic compound whereby a non-ionic active agent is formed comprising a mixtureof surface active compounds having, in'th'e'jmolecule, ethylene oxide chains of'difiering lengths and thereafter,
- Suitable solvents for the non-ionic surface active agents are low hidleciilar' vveight aliphatic alcohols and retai er,
- suitableprecipitating agents are saturated aliphatic hydrocarbbiis, 'for example, normal-'pent'ane', iso hexane, normal-hexane, 'isopentane, normal-heptar'ie, iso 'octaiie.
- a preferred material is isohexarie.
- p p Lissapol NXA is a surface active agent having the formula R A O (CH H O -),;CH CH5 OH ivhfe R is an alien grouphaviiig, "an the average, car Ben atoms; fA'is a benzene ring; and iii'vvhi ch the value of it varis,jb'ii1gapproximately '12. Lis s'a p'ol i's'a'rgister'd trademark.
- Example 1 proximately IOgiaiiisBf surface a'eave agent had'beii thrown out of solution.
- the lower layer consisting of the precipitated liquid surface active agent was removed, being referred to hereinafter as fraction 1.
- fraction 2 The addition of iso-octane to the remaining solution was continued until a further grams of surface active agent had been thrown out of solution.
- the lower layer consisting of the precipitated liquid surface active agent was removed, being referred to hereinafter as fraction 2.
- Example 2 This example illustrates the difference in properties of the feedstock, that is, untreated Lissapol NXA and fractions 1, 2 and 3.
- the liquid surface active agent was convertedto solid form by the process described in the specification filed in respect of British patent application Serial No. 697,315.
- fractions 1, 2 and 3 differ in properties from' the feedstock and from each other. Furthermore the precipitated fractions, fractions 1 and 2 are superior to the feedstock and to fraction 3 in the ease of formation of solid adducts with urea and, in respect of colour of product.
- a process for the fractionation of a non-ionic surface active agent containing a mixture of surface active poly ethyl oxy condensation products of compoundsselected from the group consisting of fatty acids, resin acids, alcohols, alkylated phenols and mercaptans to obtain fractions differing in surface-active characteristics which comprises adding a saturated aliphatic hydrocarbon as a precipitating agent to a solution of saidsurface active agent in an organic solvent selected from the group consisting of low molecular weight alcohols, low molecular weight ketones, aromatic hydrocarbons, naphthenes and chlorinated hydrocarbons, said surface active agent being only partially soluble in saidprecipitating agent and said precipitating agent being a liquid which is miscible with said solvent, whereby part of said surface active agent is thrown out of solution to form a precipitated fraction and thereafter recovering said fraction.
- a process for the production of a non-ionic surface active agent which comprises reacting ethylene oxide with an organic compound selected from the group consisting of fatty acids, resinacids alcohols, alkylated phenols. and
- mercaptans to form a non-ionic surface active agent therewith containing a mixture of surface active compounds having, in the molecule, ethylene oxide chains of differing lengths and thereafter, in the presence of an organic solvent selected from the group consisting of low molecular weight alcohols, low molecular weight ketones, aromatic hydrocarbons, naphthenes and chlorinated hydrocarbons, fractionally precipitating part of the product containing compounds having an ethylene oxide chain of at least the desired length by the addition of an unsaturated aliphatic hydrocarbon as a liquid precipitating agent which is miscible with said solvent and in which said agent is only partly soluble, and thereafter recycling at least part of the remainder of the product containing compounds having a relatively short ethylene oxide chain to the reaction mixture comprising ethylene oxide and said organic compound.
- an organic solvent selected from the group consisting of low molecular weight alcohols, low molecular weight ketones, aromatic hydrocarbons, naphthenes and chlorinated hydrocarbons
- a process for the production of a non-ionic surface active agent which comprises reacting ethylene oxide with an organic compound selected from the group consisting of fatty acids, resin acids, alcohols, alkylated phenols and mercaptans to form a non-ionic surface active agent therewith, containing a mixture of surface active compounds having, in the molecule, ethylene oxide chains of differing lengths and thereafter, in the presence of an organic solvent selected from the group consisting of low molecular weight alcohols, low molecular weight ketones, aromatic hydrocarbons, naphthenes and chlorinated hydrocarbons, fractionally precipitating part of the product containing compounds having an ethylene oxide chain of at least the desired length by the addition of an unsaturated aliphatic hydrocarbon as a liquid precipitating agent which is miscible with said solvent and in which said agent is only partly soluble, thereafter subjecting the solution remaining after removal of the precipitated fraction to distillation for the removal of the organic solvent and precipitating agent, and recycling the surface active agent to the reaction mixture comprising ethylene oxide and said organic
- each of the compounds forming the mixture of non-ionic surfaceactive compounds is a compound having the formula R-A-0-(CH CH O-) CH CH 0I-I wherein R is an alkyl group and A is a phenylene, group, R in the mixture having an average of 8 carbon atoms and A in the mixture having an average value of 12.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Luminescent Compositions (AREA)
- Fire-Extinguishing Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB33051/52A GB756334A (en) | 1952-12-31 | 1952-12-31 | Improvements in or relating to the production and/or separation of non-ionic surface active agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2814613A true US2814613A (en) | 1957-11-26 |
Family
ID=10347874
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US398206A Expired - Lifetime US2814613A (en) | 1952-12-31 | 1953-12-14 | Production and/or separation of nonionic surface active agents |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2814613A (is") |
| BE (1) | BE525459A (is") |
| FR (1) | FR1096250A (is") |
| GB (1) | GB756334A (is") |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3124602A (en) * | 1964-03-10 | Aliphatic esters of unsaturated | ||
| US4079086A (en) * | 1975-04-28 | 1978-03-14 | Monsanto Company | Process for reacting alkyl epoxides with glycols |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4603568A2 (en) | 2018-01-26 | 2025-08-20 | Ecolab USA Inc. | Solidifying liquid amine oxide surfactant with urea binder and optional carrier |
| MX2020007846A (es) | 2018-01-26 | 2020-09-25 | Ecolab Usa Inc | Solidificacion de tensioactivos de oxido de amina, betaina y/o sultaina liquidos con un portador. |
| MX2020007861A (es) | 2018-01-26 | 2020-09-18 | Ecolab Usa Inc | Solidificacion de tensioactivos anionicos liquidos. |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2118454A (en) * | 1935-03-30 | 1938-05-24 | Shell Dev | Process for separating high molecular mixtures of the ester type |
| US2226119A (en) * | 1940-03-06 | 1940-12-24 | Petrolite Corp | Flooding process for recovering oil from subterranean oil-bearing strata |
| US2233382A (en) * | 1940-03-06 | 1941-02-25 | Petrolite Corp | Flooding process for recovering oil from subterranean oil-bearing strata |
| US2674619A (en) * | 1953-10-19 | 1954-04-06 | Wyandotte Chemicals Corp | Polyoxyalkylene compounds |
-
0
- BE BE525459D patent/BE525459A/xx unknown
-
1952
- 1952-12-31 GB GB33051/52A patent/GB756334A/en not_active Expired
-
1953
- 1953-12-14 US US398206A patent/US2814613A/en not_active Expired - Lifetime
- 1953-12-24 FR FR1096250D patent/FR1096250A/fr not_active Expired
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2118454A (en) * | 1935-03-30 | 1938-05-24 | Shell Dev | Process for separating high molecular mixtures of the ester type |
| US2226119A (en) * | 1940-03-06 | 1940-12-24 | Petrolite Corp | Flooding process for recovering oil from subterranean oil-bearing strata |
| US2233382A (en) * | 1940-03-06 | 1941-02-25 | Petrolite Corp | Flooding process for recovering oil from subterranean oil-bearing strata |
| US2674619A (en) * | 1953-10-19 | 1954-04-06 | Wyandotte Chemicals Corp | Polyoxyalkylene compounds |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3124602A (en) * | 1964-03-10 | Aliphatic esters of unsaturated | ||
| US4079086A (en) * | 1975-04-28 | 1978-03-14 | Monsanto Company | Process for reacting alkyl epoxides with glycols |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1096250A (fr) | 1955-06-16 |
| BE525459A (is") | |
| GB756334A (en) | 1956-09-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2814612A (en) | Urea adducts | |
| EP3649111B1 (fr) | Molécule polyaromatique portant une fonction oxyde de nitrile | |
| US2814613A (en) | Production and/or separation of nonionic surface active agents | |
| CH392496A (fr) | Procédé de préparation de diméthyl-1,1 indanes alcoylés | |
| US3470251A (en) | Separation and purification of secondary alkyl primary amines | |
| DE1593653B2 (de) | Verfahren zur herstellung von polyalkyltetralinen durch umsetzung von 2,3dimethylbuten mit einem in para-stellung methyl- oder aethylsubstituierten alphamethylstyrol | |
| US2540886A (en) | Cyclohexanone-formaldehyde resin production | |
| US2359980A (en) | Process for refining pine oleoresin | |
| US4321214A (en) | Extreme purification of sulfonic-type acids for processing to highly overbased metal sulfonates | |
| US2248831A (en) | Alkylated phenol | |
| US3888917A (en) | Organic sulfonate extraction process | |
| KR930006604B1 (ko) | 시클로알칸올의 제조방법 | |
| EP0000464B1 (fr) | Procédé de purification du mercaptobenzothiazole | |
| US2036469A (en) | Petroleum sulphonic acids and sul | |
| CA3145233A1 (fr) | Molecule portant une fonction oxyde de nitrile | |
| US2559083A (en) | Decolorization of polyolefinic | |
| EP1226135B1 (fr) | Procede de preparation d'un derive du thiophene | |
| US3026315A (en) | Separation of isothiocineole | |
| US4032581A (en) | Method for separation of m- or p-cresol | |
| US2235840A (en) | Process for producing hydroxy citronellal | |
| EP0618285B1 (en) | Treated labdanum oil, process for producing the same and perfume composition containing the game | |
| US2697122A (en) | Process for isolating phenolic compounds from mixtures thereof | |
| US3450749A (en) | Organic sulfonate production and purification | |
| US2538262A (en) | Method of purifying sulfuric acid alkylates | |
| US2734923A (en) | Preparation of naphthenic alcohols |