US2671115A - Ethers of z-butyloc - Google Patents
Ethers of z-butyloc Download PDFInfo
- Publication number
- US2671115A US2671115A US2671115DA US2671115A US 2671115 A US2671115 A US 2671115A US 2671115D A US2671115D A US 2671115DA US 2671115 A US2671115 A US 2671115A
- Authority
- US
- United States
- Prior art keywords
- moles
- ethylene oxide
- products
- ethers
- detergency
- 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
- 150000002170 ethers Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000000047 product Substances 0.000 description 18
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 13
- 238000000034 method Methods 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 3
- 241000004297 Draba Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- DTPCFIHYWYONMD-UHFFFAOYSA-N decaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO DTPCFIHYWYONMD-UHFFFAOYSA-N 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical class CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- BBMCTIGTTCKYKF-UHFFFAOYSA-N n-Heptanol Natural products CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- -1 secondary alcohol ethers Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/10—Saturated ethers of polyhydroxy compounds
- C07C43/11—Polyethers containing —O—(C—C—O—)n units with ≤ 2 n≤ 10
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
Definitions
- the present invention relates to compounds having high surface-activity in aqueous solutions and to'xprocesses for preparing the said compounds.
- v I I In my prior Patents Nos. 2,508,035 and 2,508,036 issued-May 16, 1950, I have disclosed polyglycol ethers of certain branched chain alcohols, namely, 5-ethyl nonanol-2 and Z-n-propyl heptanol. These products are produced by condensing ethylene oxide with the respective alcohols. While these compounds showespecially low and therefore advantageous wetting-out speeds when aqueous solutions thereof are tested by the Draves test, these products have been found to be somewhat deficient ln detergency.
- Relative detergency may be measured by any quantitative method; however for the purpose oi evaluating the present and related products I ,have used the method described by Jay C. Harris "in Soap and Sanitary Chemicals for August and September, 1943. By the application of this method it is possible to evaluate the dctergency of a product in terms of any standard detergent. For convenience I have compared the detergency of the present and related products with the detergency of Gardinol, which is a commercial detergent product produced by sulfating the alcohols derived by hydrogenation of coconut oil fatty acids.
- the detergency 01 the present and related products as determined by the Harris method is illustrated in the following table:
- products are prepared by condensing et ylene oxide with 2-butyloctanol-1 until at least 5 mol been cond densation oxide eith heating t
- a catalyst for this purpose any alkaline materials, such as an alkali metal hydroxide or alcoholate may be used.
- the catalyst may be employed in relatively from 0.5% to 1% being small amoun usually employed.
- the catalyst 2'-butyloctanol -1.
- the products so produced are secondary alcohol ethers and are believed to have the structure:
- n has a value of at least 4 but not in excess of 20.
- EXAMPLE 3 A. portion of. the: product obtained in Example 2; weighing 191- g., was further treated with 41 g: ofethylene oxideusing the same apparatus" as; describedabove. The product obtained cor responded to the decaethylene glycol ether" of EXAMPLE 4' Draves test of the products when dissolved:v in:
- the process which comprises passing ethylene oxidez into: Ze-blltYlOCtfiIlOl-l at a temperature; of from 110 c. to 170 0. until at least 5 moles, but less than 21 moles, of said ethylene oxide have combined with each mole of said 2-butyloctanol-1.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Patented Mar. 2, 1954 SAME Milton Kcsmin, Dayton,
santo Chemical Compa poi-ation of Delaware No Drawing. Application August 14, 1950,
Serial No. 179,3 Claims. (01. 260-615) The present invention relates to compounds having high surface-activity in aqueous solutions and to'xprocesses for preparing the said compounds. v I I In my prior Patents Nos. 2,508,035 and 2,508,036 issued-May 16, 1950, I have disclosed polyglycol ethers of certain branched chain alcohols, namely, 5-ethyl nonanol-2 and Z-n-propyl heptanol. These products are produced by condensing ethylene oxide with the respective alcohols. While these compounds showespecially low and therefore advantageous wetting-out speeds when aqueous solutions thereof are tested by the Draves test, these products have been found to be somewhat deficient ln detergency.
I have now found that if at least 5, but less than 21, moles of ethylene oxide be condensed with 2-butyloctanol-1 that a series of products is obtained which exhibit not only excellent wetting out properties but also excellent detergency. As a matter of fact, the detergency of the present products is superior to that of the corresponding products made from n-dodecanol.
Relative detergency may be measured by any quantitative method; however for the purpose oi evaluating the present and related products I ,have used the method described by Jay C. Harris "in Soap and Sanitary Chemicals for August and September, 1943. By the application of this method it is possible to evaluate the dctergency of a product in terms of any standard detergent. For convenience I have compared the detergency of the present and related products with the detergency of Gardinol, which is a commercial detergent product produced by sulfating the alcohols derived by hydrogenation of coconut oil fatty acids.
The detergency 01 the present and related products as determined by the Harris method is illustrated in the following table:
-BUTYLOC- OF MAKING Ohio, assignor to Monny, St. Louis, Mo., a cor- TENT OF BOLYGLYCOL ETHERS OF 2 TANOL-l AND PROCESS Detergency, Percent of Gardinol Product Tested I 100% Active Built 1 M 300 50 300 p.p.m. p. p. m. p. p. m. p. 11ml \M Lorol +10 moles ethylene oxide 112 112 1 Lornl +15 moles ethylene oxide. 106 109 1:3? 2-n- Pr0pylh eptanol+5 moles etnylcne oxide 50 45 111 106 2-n-Propylhcptanol+l0 moles ethylene oxide 78 09 109 2-n-Propylhcptanol+l6 moles ethylene oxide 102 87 93 109 5-Ethylngnanol-2+5 moles ethylene ou 6 s. 3 5-Ethylnonanol-2-l-l0 moles J 37 106 ethylene oxide 114 110 111 5-l%1th1ylnonaanol-2+l5 moles e 1y ene 0x1 e .110 101 2-Brllztylogtanol-l+fi moles ethyl- 101 116 s e on e .1 "9 42 2-But1yloctaol-l+7.5 moles o 100 65 e y sue on e 102 93 12 2-Butylqcitanol-l+l0 moles othyl- 7 136 ene on e 107 110 3" 1 Z-Butylqctanol-l-l-lfimolesethyl- I a 43 ene oxide 102 93 129 126 1 The builder consisted of 40 40 parts of starch for each 20 parts 1 Cocoanut oil alcohols.
The present parts of tetrasodium pyrophosphate,
of the active constituent.
products are prepared by condensing et ylene oxide with 2-butyloctanol-1 until at least 5 mol been cond densation oxide eith heating t The cond es, but not in ensation reacti excess of 20 moles, have The conon is aided by the presence of a catalyst. For this purpose any alkaline materials, such as an alkali metal hydroxide or alcoholate may be used. The catalyst may be employed in relatively from 0.5% to 1% being small amoun usually employed. The catalyst 2'-butyloctanol -1.
is, added to the liquid alcohol at the beginning'ot the reaction.
The products so produced are secondary alcohol ethers and are believed to have the structure:
CH2CH2CH2CH:
CHICHiCHEOHlOHlCHQCHCHI (zHAOMCaIEhOH where n is an integer having a value of from 4 to 19.
4 What I claim is: 1. Compounds having the formula:
OHzCHaCHzCH;
CHaCHaCHzCHzCHnCHzCHCH:
t ((ID:H4O)"C2H4OH where n has a value of at least 4 but not in excess of 20.
2. Compounds having the formula:
The following examples will further illustrate oHzcHflcHiom this invention: omomomomomomonom EXAMPLE 1 I!) 1) 141.0 g. (0.756 mole) of Z-butyloctanol-i was 2Hl )4 2H4OH placed in a glass flask, 2.6 g. of powdered KOI-I 3. Compounds having the formula: added and the contents then heated to 120 C. 0320320112053 A stream of gaseous ethylene oxide was passed into the alcohol. by; means of? a. gas dispersing; tube and tliestream continued until 16710 g: of
CHaCHzQHaCHzCH: CH2. QHa
ethylene oxide had combined. The mass became hot due to the exothermic reactionheati and the temperature was controlled by. cooling, m" Compounds having the formula" the flask by the application otfcold Water. toythe' OHzOHzCHzCHQ exterior. In this way the temperaturewas maincmomemomomomoncnz tained at about 150 during the progress of the reaction.
The product obtained correspond'sto the=penta=- no (C2H40)14C2H40H ethylene glycol ether of 2-butyloctanol-1.
EXAMPLE 2' A portion of the product obtained. above, weighing 208v g., was further treated with 5'6= g: of ethylene oxide using thesame apparatus as described above- There was thus obtained a 7-.5: 1 molan; ratio. ethylene. oxide-Z-butyloctanol- 1 condensation product.
EXAMPLE 3 A. portion of. the: product obtained in Example 2; weighing 191- g., was further treated with 41 g: ofethylene oxideusing the same apparatus" as; describedabove. The product obtained cor responded to the decaethylene glycol ether" of EXAMPLE 4' Draves test of the products when dissolved:v in:
water tdforma 0.5 solution gave. the following. values:
The process" which comprises passing ethylene oxidez into: Ze-blltYlOCtfiIlOl-l at a temperature; of from 110 c. to 170 0. until at least 5 moles, but less than 21 moles, of said ethylene oxide have combined with each mole of said 2-butyloctanol-1.
men:
References-.- Gitedi; the file ofi patent:
UNITED STATES PATENTS Number; Name Eaten 1.69.6,314; Young. Dec. 25,. 1921i- 1,270,578 Schoelleneta1. Aug... 2.1 1934 2,226,119. De Gmoteet a1. .Dec..24,-, 19. 40
5; 2 316,842 Coleman Apr. 20,. 1943. 2,355,823. Schlegel. Aug..15,, I944! 2,491,533. Sworn; Dec. 20,. 1949. 2,508,035 Kosmim May, 16,]. I950 2,5118936. Kosmin. May. 16,. 1950.
Table- Spec-dot." PifOdilOtlTQStGd. Wetting, Seconds Eiiamplecllnuflnu 2.6. Example 2 2.. 9. Example 3'... Instantaneous. ExammeaQ 214. LoroLH-ldmoies ethylene oxide 10. 9. ljoroTH-l-fi'moles ethylene oxide 30'. 8.
Sokol' out. 31. 1950
Claims (1)
1. COMPOUNDS HAVING TE FORMULA:
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2671115A true US2671115A (en) | 1954-03-02 |
Family
ID=3440127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2671115D Expired - Lifetime US2671115A (en) | Ethers of z-butyloc |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2671115A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2870220A (en) * | 1953-08-11 | 1959-01-20 | Union Carbide Corp | Production of nonionic surface active agents |
| US2932670A (en) * | 1957-09-16 | 1960-04-12 | Monsanto Chemicals | Derivatives of glycerol 1, 3-dialkyl ethers and their preparation |
| US3539519A (en) * | 1968-02-23 | 1970-11-10 | Continental Oil Co | Low foaming nonionic detergents |
| US3887624A (en) * | 1972-06-07 | 1975-06-03 | Jefferson Chem Co Inc | Vinylidene alcohol compositions |
| US4082506A (en) * | 1975-10-15 | 1978-04-04 | Union Carbide Corporation | Printing formulations |
| US5562866A (en) * | 1995-06-20 | 1996-10-08 | Albemarle Corporation | Formulated branched chain alcohol ether sulfate compounds |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1696874A (en) * | 1928-12-25 | Process of making ethylene glycol monoalkyl ethers | ||
| US1970578A (en) * | 1930-11-29 | 1934-08-21 | Ig Farbenindustrie Ag | Assistants for the textile and related industries |
| US2226119A (en) * | 1940-03-06 | 1940-12-24 | Petrolite Corp | Flooding process for recovering oil from subterranean oil-bearing strata |
| US2316842A (en) * | 1939-11-18 | 1943-04-20 | Gen Motors Corp | Leak testing bath and method of the testing |
| US2355823A (en) * | 1944-08-15 | Polyglycol ethers of higher second | ||
| US2491533A (en) * | 1948-01-16 | 1949-12-20 | Swern Daniel | Ethers of 9,10-dihydroxyoctadecanol |
| US2508035A (en) * | 1950-05-16 | Compounds having surface activity | ||
| US2508036A (en) * | 1950-05-16 | Compounds having high wetting | ||
| US2527970A (en) * | 1950-10-31 | Hydroxy ethers and process for |
-
0
- US US2671115D patent/US2671115A/en not_active Expired - Lifetime
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1696874A (en) * | 1928-12-25 | Process of making ethylene glycol monoalkyl ethers | ||
| US2355823A (en) * | 1944-08-15 | Polyglycol ethers of higher second | ||
| US2508035A (en) * | 1950-05-16 | Compounds having surface activity | ||
| US2508036A (en) * | 1950-05-16 | Compounds having high wetting | ||
| US2527970A (en) * | 1950-10-31 | Hydroxy ethers and process for | ||
| US1970578A (en) * | 1930-11-29 | 1934-08-21 | Ig Farbenindustrie Ag | Assistants for the textile and related industries |
| US2316842A (en) * | 1939-11-18 | 1943-04-20 | Gen Motors Corp | Leak testing bath and method of the testing |
| US2226119A (en) * | 1940-03-06 | 1940-12-24 | Petrolite Corp | Flooding process for recovering oil from subterranean oil-bearing strata |
| US2491533A (en) * | 1948-01-16 | 1949-12-20 | Swern Daniel | Ethers of 9,10-dihydroxyoctadecanol |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2870220A (en) * | 1953-08-11 | 1959-01-20 | Union Carbide Corp | Production of nonionic surface active agents |
| US2932670A (en) * | 1957-09-16 | 1960-04-12 | Monsanto Chemicals | Derivatives of glycerol 1, 3-dialkyl ethers and their preparation |
| US3539519A (en) * | 1968-02-23 | 1970-11-10 | Continental Oil Co | Low foaming nonionic detergents |
| US3887624A (en) * | 1972-06-07 | 1975-06-03 | Jefferson Chem Co Inc | Vinylidene alcohol compositions |
| US4082506A (en) * | 1975-10-15 | 1978-04-04 | Union Carbide Corporation | Printing formulations |
| US5562866A (en) * | 1995-06-20 | 1996-10-08 | Albemarle Corporation | Formulated branched chain alcohol ether sulfate compounds |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3101374A (en) | Polyoxyalkylene surface active agents having heteric polyoxyethylene solubilizing chains | |
| US2508036A (en) | Compounds having high wetting | |
| US3022335A (en) | Surface active polyoxyalkylene compounds having a plurality of heteric polyoxypropylene-polyoxyethylene chains | |
| US4280919A (en) | Detergents and cleansers containing oxyalkylated alcohols as biodegradable, low-foam surfactants | |
| US3406208A (en) | Polyglycol ethers suitable for detergent preparations, and process for preparing the same | |
| US2828345A (en) | Hydroxypolyoxyethylene diethers of polyoxybutylene glycols | |
| US2355823A (en) | Polyglycol ethers of higher second | |
| US2508035A (en) | Compounds having surface activity | |
| US4668423A (en) | Liquid biodegradable surfactant and use thereof | |
| US3953351A (en) | Liquid laundry detergent | |
| US4792419A (en) | Ether sulfonates | |
| US2671115A (en) | Ethers of z-butyloc | |
| US2932670A (en) | Derivatives of glycerol 1, 3-dialkyl ethers and their preparation | |
| US3021372A (en) | Low foam, high wetting polypropyleneterminated alkylphenoxypolyethoxyalkanols | |
| US3507798A (en) | Built detergents containing nonionic polyoxyalkylene surface active materials | |
| FR2230718B1 (en) | ||
| US3931271A (en) | Process for the production of secondary alcohol ether sulfates | |
| US2133480A (en) | Production of ethers suitable as dispersing agents and of preparations therefrom | |
| US3539519A (en) | Low foaming nonionic detergents | |
| US2164431A (en) | Production of etherg suitable as dis | |
| US2932616A (en) | Detergent compositions | |
| JP5242147B2 (en) | Surfactant composition | |
| US3078315A (en) | Polyoxyalkylene products | |
| US2671116A (en) | Polyglycol ethers of z | |
| Matheson et al. | Peaked distribution ethoxylates‐Their preparation, characterization and performance evaluation |