JPS6339852A - Stabilized primary alcohol ethoxysulfate - Google Patents
Stabilized primary alcohol ethoxysulfateInfo
- Publication number
- JPS6339852A JPS6339852A JP61183351A JP18335186A JPS6339852A JP S6339852 A JPS6339852 A JP S6339852A JP 61183351 A JP61183351 A JP 61183351A JP 18335186 A JP18335186 A JP 18335186A JP S6339852 A JPS6339852 A JP S6339852A
- Authority
- JP
- Japan
- Prior art keywords
- primary alcohol
- ethylene oxide
- lactate
- temperature
- mol
- 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.)
- Granted
Links
- -1 primary alcohol ethoxysulfate Chemical class 0.000 title claims abstract description 57
- 150000003138 primary alcohols Chemical class 0.000 claims abstract description 93
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 49
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N Lactic Acid Natural products CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims abstract description 46
- 239000004310 lactic acid Substances 0.000 claims abstract description 23
- 235000014655 lactic acid Nutrition 0.000 claims abstract description 23
- 230000001180 sulfating effect Effects 0.000 claims abstract description 11
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 12
- 229940001447 lactate Drugs 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 10
- CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical group C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000001540 sodium lactate Substances 0.000 claims description 5
- 235000011088 sodium lactate Nutrition 0.000 claims description 5
- 229940005581 sodium lactate Drugs 0.000 claims description 5
- PHZLMBHDXVLRIX-UHFFFAOYSA-M potassium lactate Chemical group [K+].CC(O)C([O-])=O PHZLMBHDXVLRIX-UHFFFAOYSA-M 0.000 claims description 3
- 239000001521 potassium lactate Substances 0.000 claims description 3
- 235000011085 potassium lactate Nutrition 0.000 claims description 3
- 229960001304 potassium lactate Drugs 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 29
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 abstract description 25
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 11
- 235000019441 ethanol Nutrition 0.000 abstract description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 6
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000047 product Substances 0.000 abstract description 5
- 239000004094 surface-active agent Substances 0.000 abstract description 3
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 abstract description 2
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 69
- 238000003756 stirring Methods 0.000 description 44
- 239000007864 aqueous solution Substances 0.000 description 31
- 239000000243 solution Substances 0.000 description 29
- 239000003054 catalyst Substances 0.000 description 24
- 239000003795 chemical substances by application Substances 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 229910001873 dinitrogen Inorganic materials 0.000 description 12
- 239000007789 gas Substances 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- 239000006227 byproduct Substances 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 11
- 229910001220 stainless steel Inorganic materials 0.000 description 11
- 239000010935 stainless steel Substances 0.000 description 11
- SMYREFDDLSTNKQ-UHFFFAOYSA-N oxocan-2-ol Chemical compound OC1CCCCCCO1 SMYREFDDLSTNKQ-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 229910015900 BF3 Inorganic materials 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- PWZFXELTLAQOKC-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide;tetrahydrate Chemical compound O.O.O.O.[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O PWZFXELTLAQOKC-UHFFFAOYSA-A 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000002421 finishing Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 230000019635 sulfation Effects 0.000 description 3
- 238000005670 sulfation reaction Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
- YNVZDODIHZTHOZ-UHFFFAOYSA-K 2-hydroxypropanoate;iron(3+) Chemical compound [Fe+3].CC(O)C([O-])=O.CC(O)C([O-])=O.CC(O)C([O-])=O YNVZDODIHZTHOZ-UHFFFAOYSA-K 0.000 description 1
- KSNGEYQWLMRSIR-UHFFFAOYSA-L 2-hydroxypropanoate;manganese(2+) Chemical compound [Mn+2].CC(O)C([O-])=O.CC(O)C([O-])=O KSNGEYQWLMRSIR-UHFFFAOYSA-L 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- FDQGNLOWMMVRQL-UHFFFAOYSA-N Allobarbital Chemical compound C=CCC1(CC=C)C(=O)NC(=O)NC1=O FDQGNLOWMMVRQL-UHFFFAOYSA-N 0.000 description 1
- 239000004251 Ammonium lactate Substances 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 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
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000004435 Oxo alcohol Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- CANRESZKMUPMAE-UHFFFAOYSA-L Zinc lactate Chemical compound [Zn+2].CC(O)C([O-])=O.CC(O)C([O-])=O CANRESZKMUPMAE-UHFFFAOYSA-L 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229940059265 ammonium lactate Drugs 0.000 description 1
- 235000019286 ammonium lactate Nutrition 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- RZOBLYBZQXQGFY-HSHFZTNMSA-N azanium;(2r)-2-hydroxypropanoate Chemical compound [NH4+].C[C@@H](O)C([O-])=O RZOBLYBZQXQGFY-HSHFZTNMSA-N 0.000 description 1
- HLKMEIITONDPGG-UHFFFAOYSA-L barium(2+);2-hydroxypropanoate Chemical compound [Ba+2].CC(O)C([O-])=O.CC(O)C([O-])=O HLKMEIITONDPGG-UHFFFAOYSA-L 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- MKJXYGKVIBWPFZ-UHFFFAOYSA-L calcium lactate Chemical compound [Ca+2].CC(O)C([O-])=O.CC(O)C([O-])=O MKJXYGKVIBWPFZ-UHFFFAOYSA-L 0.000 description 1
- 239000001527 calcium lactate Substances 0.000 description 1
- 235000011086 calcium lactate Nutrition 0.000 description 1
- 229960002401 calcium lactate Drugs 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000002761 deinking Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- GSPKZYJPUDYKPI-UHFFFAOYSA-N diethoxy sulfate Chemical compound CCOOS(=O)(=O)OOCC GSPKZYJPUDYKPI-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- GKQWYZBANWAFMQ-UHFFFAOYSA-M lithium;2-hydroxypropanoate Chemical compound [Li+].CC(O)C([O-])=O GKQWYZBANWAFMQ-UHFFFAOYSA-M 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- OVGXLJDWSLQDRT-UHFFFAOYSA-L magnesium lactate Chemical compound [Mg+2].CC(O)C([O-])=O.CC(O)C([O-])=O OVGXLJDWSLQDRT-UHFFFAOYSA-L 0.000 description 1
- 239000000626 magnesium lactate Substances 0.000 description 1
- 235000015229 magnesium lactate Nutrition 0.000 description 1
- 229960004658 magnesium lactate Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- LMEWRZSPCQHBOB-UHFFFAOYSA-M silver;2-hydroxypropanoate Chemical compound [Ag+].CC(O)C([O-])=O LMEWRZSPCQHBOB-UHFFFAOYSA-M 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000005496 tempering Methods 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- VXYADVIJALMOEQ-UHFFFAOYSA-K tris(lactato)aluminium Chemical compound CC(O)C(=O)O[Al](OC(=O)C(C)O)OC(=O)C(C)O VXYADVIJALMOEQ-UHFFFAOYSA-K 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
- 239000011576 zinc lactate Substances 0.000 description 1
- 229940050168 zinc lactate Drugs 0.000 description 1
- 235000000193 zinc lactate Nutrition 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は低臭気性でしかも経時変化による着臭が極めて
少ない安定化した第１級アルコールエトキシサルフェー
トに関する。DETAILED DESCRIPTION OF THE INVENTION (Field of Industrial Application) The present invention relates to a stabilized primary alcohol ethoxy sulfate which has low odor and exhibits extremely little odor due to changes over time.
さらに詳しくは第１級アルコールとエチレンオキシドと
を反応させて得られる第１級アルコールエトキシレート
に特定の中和剤を添加した後、硫酸化して得られる経時
変化による臭気の発生が極めて少ない安定化した第１級
アルコールエトキシサルフェートに関するものである。More specifically, after adding a specific neutralizing agent to primary alcohol ethoxylate obtained by reacting primary alcohol and ethylene oxide, it is sulfated and stabilized with extremely little odor generation due to changes over time. It relates to primary alcohol ethoxy sulfate.
第１級アルコールとエチレンオキシドとを反応させて得
られる第１級アルコールエトキシレートを硫酸化して得
られる第１級アルコールエトキシナルフェートは界面活
性剤として広い分野で使用される。たとえば、
（１）繊維関係
ポリエステル、綿、原毛洗浄、湿潤剤、染色助剤、繊ｍ
漂白、仕上剤、帯電防止剤、繊維油剤、乳化剤。Primary alcohol ethoxynalphate, which is obtained by sulfating a primary alcohol ethoxylate obtained by reacting a primary alcohol with ethylene oxide, is used as a surfactant in a wide range of fields. For example, (1) Fiber-related polyester, cotton, raw wool washing, wetting agents, dyeing aids, fiber
Bleaching, finishing agents, antistatic agents, textile oils, emulsifiers.
■ 紙バルブ関係
湿潤剤、仕上用、脱墨剤、漂白用、脱樹脂剤、サイジン
グ剤
Ｇ）金属関係
脱脂洗浄剤、除錆・防錆剤、機械工作、潤滑剤メツキ用
、焼入れ焼きもどし剤、浸透探傷検査液用。■ Paper valve-related wetting agents, finishing, deinking agents, bleaching, resin removal agents, sizing agents G) Metal-related degreasing and cleaning agents, rust removal and rust prevention agents, machining, lubricants, plating, quenching and tempering agents , for penetrant testing liquids.
■ 農林関係 農薬乳化剤、展着剤、各種洗浄剤。■ Agriculture and forestry related Pesticide emulsifiers, spreading agents, and various cleaning agents.
（５）皮革関係 クロム酸なめし、染色、仕上げ用。(5) Leather related For chromic acid tanning, dyeing and finishing.
（６） 洗剤関係
工業用、液体家庭用、粉末家庭用、住居用、クリーニン
グ用、自動車用。(6) Detergent-related industrial use, liquid household use, powder household use, residential use, cleaning use, and automotive use.
（乃 化粧品関係 軟膏用、乳化剤、シャンプー用。(No Cosmetics related For ointments, emulsifiers, and shampoos.
■ その他 防塵剤、流失油処理剤、油分離剤 等に使用される。■ Others Dust control agent, spilled oil treatment agent, oil separation agent Used for etc.
（従来の技術）
一般に第１級アルコールとエチレンオキシドとを反応さ
せて得られる第１級アルコールエトキシレートは、水酸
化ナトリウム、水酸化カリウム、ナトリウムアルコキシ
ド等のアルカリ触媒または三フッ化ホウ素、三フフ化ホ
ウ素−錯体、五塩化アンチモン、四塩化スズ等の酸性触
媒の存在下、第１級アルコールにエチレンオキシドを付
加して製造・される。(Prior art) Primary alcohol ethoxylates obtained by reacting primary alcohols with ethylene oxide are generally prepared using alkali catalysts such as sodium hydroxide, potassium hydroxide, and sodium alkoxide, or with boron trifluoride and trifluoride. It is produced by adding ethylene oxide to a primary alcohol in the presence of an acidic catalyst such as a boron complex, antimony pentachloride, or tin tetrachloride.
このような方法で得られた第１級アルコールエトキシレ
ートは未反応の第１級アルコールを含む外に、触媒、ア
ルデヒド類、遊離酸類、過酸化物類およびその他の悪臭
あるいは着色の原因となるような不純物を微量含有して
いる。これらの不純物を含む第１級アルコールとエチレ
ンオキシドとを反応させて得られる第１級アルコールエ
トキシレートは酸またはアルカリによる中和、あるいは
アルカリ水溶液による洗浄、蒸留、還元、吸着、口過等
の方法によって精製される。アルカリ触媒は通常、５Ａ
Ｍ、リン酸等の鉱酸あるいは酢酸等を添加して中和処理
して精製される。このようにして得られた第１級アルコ
ールエトキシレートをざらに硫酸化して得られる第１級
アルコールエトキシサルフェートはこの他にも臭気の原
因となる不純物があって、経時変化と共に悪臭を発生す
る問題がある。The primary alcohol ethoxylate obtained by this method not only contains unreacted primary alcohol, but also contains catalysts, aldehydes, free acids, peroxides, and other substances that may cause odor or color. Contains trace amounts of impurities. The primary alcohol ethoxylate obtained by reacting the primary alcohol containing these impurities with ethylene oxide can be neutralized with an acid or alkali, or washed with an alkaline aqueous solution, distilled, reduced, adsorbed, passed through the mouth, etc. Refined. Alkaline catalysts are usually 5A
It is purified by neutralization by adding mineral acids such as M, phosphoric acid, or acetic acid. The primary alcohol ethoxy sulfate obtained by roughly sulfating the primary alcohol ethoxylate obtained in this way contains other impurities that cause odor, and the problem is that it develops a bad odor as it changes over time. There is.
特に近年、家庭用洗剤の高級化志向から洗剤原料に対す
る無臭化の要求が益々増大している。さらに経時変化し
た第１級アルコールエトキシレートに三酸化硫黄、クロ
ルスルホン酸等の硫酸化剤で硫酸化した場合には生成し
た第１級アルコールエトキシサルフェート−の臭気およ
び色相が著しく悪化するという問題がある。以上のよう
に従来技術で得られた第１級アルコールエトキシレート
を用いて目的とする第１級アルコールエトキシサルフェ
ート製品にした場合、第１級アルコールエトキシサルフ
ェート製品の品質および劣化の原因となる問題があり好
ましくない。Particularly in recent years, there has been an increasing demand for odorless detergent raw materials due to the trend towards higher quality household detergents. Furthermore, when primary alcohol ethoxylate that has changed over time is sulfated with a sulfating agent such as sulfur trioxide or chlorosulfonic acid, there is a problem that the odor and color of the generated primary alcohol ethoxy sulfate deteriorate significantly. be. As described above, when primary alcohol ethoxylate obtained by the conventional technology is used to produce the desired primary alcohol ethoxy sulfate product, there are problems that cause quality and deterioration of the primary alcohol ethoxy sulfate product. Yes, it's not good.
特に第１級アルコールとエチレンオキシドとを反応させ
て第１級アルコールエトキシレートを製造する際に使用
される水酸化ナトリウム、水酸化カリウム、ナトリウム
アルコキシド等のアルカリ触媒は通常、硫酸、リン酸等
の鉱酸あるいは酢酸のごとき中和剤を添加して中和処理
して精製されるが、第１級アルコールとエチレンオキシ
ドとを反応させて第１級アルコールエトキシレートを製
造する際に従来の中和剤を使用し硫酸化して第１級アル
コールエトキシサルフェートにした場合には第１級アル
コールエトキシサルフェートの臭気および品質の経時変
化に問題があった。In particular, alkaline catalysts such as sodium hydroxide, potassium hydroxide, and sodium alkoxide used when producing primary alcohol ethoxylates by reacting primary alcohols with ethylene oxide are usually used with minerals such as sulfuric acid and phosphoric acid. It is purified by adding a neutralizing agent such as acid or acetic acid to neutralize it, but when producing primary alcohol ethoxylate by reacting primary alcohol with ethylene oxide, conventional neutralizing agents are not used. When used and sulfated to produce primary alcohol ethoxy sulfate, there were problems with the odor and quality change over time of the primary alcohol ethoxy sulfate.
（発明が解決しようとする問題点）
本発明の目的は、第１級アルコールとエチレンオキシド
とを反応させて得られた第１級アルコールエトキシレー
トについて、さらに硫酸化して得られる第１級アルコー
ルエトキシサルフェートの経時変化による臭気の発生が
極めて少ない第１級アルコールエトキシサルフェートを
提供することにある。(Problems to be Solved by the Invention) The object of the present invention is to produce a primary alcohol ethoxysulfate obtained by further sulfating a primary alcohol ethoxylate obtained by reacting a primary alcohol with ethylene oxide. An object of the present invention is to provide a primary alcohol ethoxy sulfate which generates extremely little odor due to changes over time.
（問題点を解決するための手段）
本発明は第１級アルコールにエチレンオキシドを付加し
た第１級アルコールエトキシレートに乳酸および／また
は乳酸塩を含有させた第１級アルコールエトキシレート
を硫酸化することを特徴とする安定化した第１級アルコ
ールエトキシサルフェートに関するものである。(Means for Solving the Problems) The present invention involves sulfating a primary alcohol ethoxylate obtained by adding lactic acid and/or a lactate to a primary alcohol ethoxylate obtained by adding ethylene oxide to a primary alcohol. This invention relates to a stabilized primary alcohol ethoxy sulfate characterized by:
本発明で使用する乳酸は醗酵法および合成法のいずれの
方法で製造されたものでもよく、また乳酸の純度は特に
限定するものでないが通常市販されている工業用、醸造
用、食品添加物用のいずれも使用できる。The lactic acid used in the present invention may be produced by either a fermentation method or a synthetic method, and the purity of the lactic acid is not particularly limited. Either can be used.
本発明で使用する乳酸塩は乳酸ナトリウム、乳酸カリウ
ム、乳酸リチウム等の乳酸のアルカリ金属塩、乳酸カル
シウム、乳酸マグネシウム、乳酸バリウム等の乳酸のア
ルカリ土類金属塩、乳酸アルミニウム、乳酸亜鉛、乳酸
銀、乳酸鋼、乳酸鉄、乳酸マンガン、乳酸アンモニウム
等があり、特に乳酸ナトリウム、乳酸カリウムが好まし
い。The lactate salts used in the present invention include alkali metal salts of lactic acid such as sodium lactate, potassium lactate, and lithium lactate, alkaline earth metal salts of lactic acid such as calcium lactate, magnesium lactate, and barium lactate, aluminum lactate, zinc lactate, and silver lactate. , lactic acid steel, iron lactate, manganese lactate, ammonium lactate, etc., and sodium lactate and potassium lactate are particularly preferred.
本発明で使用する乳酸および／または乳酸塩の添加量は
第１級アルコールエトキシレート１００１を部に対して
５〜０．００１重Ｍ部、好ましくは１〜０．０５重量部
である。添加に際し、水溶液のｐＨは４〜９、好ましく
は５〜７の範囲にすることが好ましい。The amount of lactic acid and/or lactate used in the present invention is 5 to 0.001 parts by weight, preferably 1 to 0.05 parts by weight per part of primary alcohol ethoxylate 1001. Upon addition, the pH of the aqueous solution is preferably in the range of 4 to 9, preferably 5 to 7.
本発明の乳酸および／または乳酸塩の添加方法は第１級
アルコールとエチレンオキシドをアルカリ触媒の存在下
で反応させて得られる未中和の第１級アルコールエトキ
シレートに乳酸を添加する方法、あるい触媒を中和した
状態または口過等の公知の方法によって触媒を除去した
第１級アルコールエトキシレートに乳酸および／または
乳酸塩を添加する方法がある。乳酸および／または乳酸
塩の添加は第１級アルコールエトキシレートに乳酸およ
び／または乳酸塩をそのまま、または溶液にして添加し
特に限定するものではないが３０分程度撹拌し、完全に
溶解させるのが好ましい。The method of adding lactic acid and/or lactate of the present invention is a method of adding lactic acid to unneutralized primary alcohol ethoxylate obtained by reacting a primary alcohol and ethylene oxide in the presence of an alkali catalyst, or There is a method of adding lactic acid and/or lactate to a primary alcohol ethoxylate in which the catalyst has been neutralized or from which the catalyst has been removed by a known method such as filtration. To add lactic acid and/or lactate, add lactic acid and/or lactate to primary alcohol ethoxylate as it is or as a solution, and stir for about 30 minutes to completely dissolve, although there is no particular limitation. preferable.
本発明で用いられる第１級アルコールとしては、飽和脂
肪族第１級アルコール、不飽和脂肪族第１級アルコール
、分岐した脂肪族第１級アルコール、等がある。The primary alcohols used in the present invention include saturated aliphatic primary alcohols, unsaturated aliphatic primary alcohols, branched aliphatic primary alcohols, and the like.
飽和脂肪族第１級アルコールとしては、メチルアルコー
ル、エチルアルコール、ブチルアルコール、オクチルア
ルコール、ステアリルアルコール、セシルアルコール等
がある。Examples of the saturated aliphatic primary alcohol include methyl alcohol, ethyl alcohol, butyl alcohol, octyl alcohol, stearyl alcohol, and cecyl alcohol.
飽和および／または不飽和脂肪族第１級アルコールとし
ては、たとえばヤシ油、ココナツツ油等の植物油の水素
化で得られる第１級アルコール、牛脂、鯨油、羊毛油等
の動物油の水素化で得られる第１級アルコール、ステア
リン酸、オレイン酸等の有機酸の水素化で得られる第１
級アルコール等が挙げられる。また、エチレンよりチー
グラー触媒による重合ならびに酸化工程を経て合成され
る偶数個の炭素原子をもつチグラーアルコール、市販さ
れているものにコンチネンタルオイル社製の商品名ｒＡ
ｌ ｆｏ ｌ◇」がある。また、α−オレフィンまた
は内部オレフィンと一酸化炭素と水素とよりコバルトカ
ルボニル系触媒の存在下、オキソ反応によるオキソアル
デヒドを経て水素による還元で得られるオキソアルコー
ルがある。市販されているものには、３ｈｅｌ１社製「
ドパノールの」および「ネオドールｅ」、８産化学社製
「オキソコール０」、三菱化成社！！！「ダイヤドール
・」等がある。Saturated and/or unsaturated aliphatic primary alcohols include, for example, primary alcohols obtained by hydrogenating vegetable oils such as coconut oil and coconut oil, and primary alcohols obtained by hydrogenating animal oils such as beef tallow, whale oil, and wool oil. Primary alcohols obtained by hydrogenation of organic acids such as stearic acid and oleic acid
alcohol, etc. In addition, Ziegler alcohol, which has an even number of carbon atoms and is synthesized from ethylene through a Ziegler catalyst polymerization and oxidation process, is commercially available under the trade name rA manufactured by Continental Oil Co.
There is "l fo l◇". There is also an oxo alcohol obtained by reducing an α-olefin or an internal olefin, carbon monoxide, and hydrogen in the presence of a cobalt carbonyl catalyst with hydrogen through an oxo reaction to form an oxo aldehyde. Commercially available products include ``3hel1''
"Dopanol" and "Neodol e", "Oxocol 0" manufactured by Yasan Kagaku Co., Ltd., Mitsubishi Kasei Corporation! ! ! There are "Diamond" etc.
分岐した脂肪族第１級第１級アルコールとしてはイソス
テリアルアルコール等がある。Examples of branched aliphatic primary alcohols include isosterial alcohols and the like.
本発明で用いられる第１級アルコールエトキシレートは
前記第１級アルコールに水酸化ナトリウム、水酸化カリ
ウムおよびナトリウムアルコキシド等のアルカリ触媒、
または三フッ化ホウ素、三フツ化ホウ素−錯体、五塩化
アンチモン、四塩化スズ等の酸性触媒の存在下エチレン
オキシドを付加反応して得られたものが挙げられる。The primary alcohol ethoxylate used in the present invention includes an alkaline catalyst such as sodium hydroxide, potassium hydroxide, and sodium alkoxide in addition to the primary alcohol.
Alternatively, those obtained by addition reaction of ethylene oxide in the presence of an acidic catalyst such as boron trifluoride, boron trifluoride complex, antimony pentachloride, tin tetrachloride, etc. can be mentioned.
本発明の第１級アルコールとエチレンオキシドとを反応
させて得られる第１級アルコールエトキシレートの反応
温度は、５０〜２００℃、特に１２０〜１８０℃の温度
範囲が好ましい。The reaction temperature of the primary alcohol ethoxylate obtained by reacting the primary alcohol and ethylene oxide of the present invention is preferably in the range of 50 to 200°C, particularly 120 to 180°C.
反応圧力は、Ｏ〜３０ Ｂ ／ ｃｒｒｒ Ｇ Ｍ特に
０．５〜２０１ｃｇ／ｃｉＧの圧力範囲が好ましい。The reaction pressure is preferably in the pressure range of 0 to 30 B/crrr GM, particularly 0.5 to 201 cg/ciG.
本発明の第１級アルコールエトキシレートの硫酸化は、
三酸化硫黄、クロルスルホン酸、スルファミン酸または
発煙硫酸等の硫酸化剤を使用することができる。The sulfation of the primary alcohol ethoxylate of the present invention is
Sulfating agents such as sulfur trioxide, chlorosulfonic acid, sulfamic acid or fuming sulfuric acid can be used.
本発明の第１級アルコールエトキシレートの硫酸化は、
第１級アルコールエトキシレートに対し硫酸化剤の量を
特に限定するものではないが０゜５〜２．０モル、好ま
しくは０．８〜１．５モルの範囲である。The sulfation of the primary alcohol ethoxylate of the present invention is
The amount of the sulfating agent relative to the primary alcohol ethoxylate is not particularly limited, but is in the range of 0.5 to 2.0 mol, preferably 0.8 to 1.5 mol.
本発明の第１級アルコールエトキシレートの硫酸化の反
応温度は、５０℃以下、特に４０℃以下の温度範囲が好
ましい。The reaction temperature for sulfation of the primary alcohol ethoxylate of the present invention is preferably in the temperature range of 50°C or lower, particularly 40°C or lower.
（作 用）
第１＠アルコールとエチレンオキシドとを反応させて得
られた第１級アルコールエトキシレートに乳酸および／
または乳酸塩を含有させて後、硫酸化して得られた第１
級アルコール１１〜キシサルフエートは、経時変化によ
る臭気の発生が極めて少なくなる作用を発揮することが
わかった。(Function) Lactic acid and/or
Or the first obtained by adding lactate and then sulfating it.
It has been found that alcohol 11-xysulfate exhibits the effect of extremely reducing the generation of odor due to changes over time.
（実 施 例）
以下、実施例を挙げて、本発明の実施の態様を具体的に
例示して説明する。本発明はこれからの実施例に限定さ
れるものではない。(Example) Hereinafter, embodiments of the present invention will be specifically illustrated and described with reference to Examples. The invention is not limited to the following embodiments.
実施例で行なった各試験方法は以下の通りである。The test methods used in the examples are as follows.
（経時変化試験）
試料２５０ｑを入れた５００ｍｊ！透明がラスピンを温
度５０℃に調製された空気温風循環°式恒渇槽に設置し
経時変化試験に供した。(Temporal change test) 500 mj containing 250 q of sample! Transparent Laspin was placed in an air temperature and air circulation ° type constant drying tank adjusted to a temperature of 50°C, and subjected to a time-dependent change test.
（１） カルボニル価 μｍｏＩ／。(1) Carbonyl value μmol/.
■ ｐＨ５重量％水溶液
（３） 臭気
試料０．５戒に水５０戒を加え温度５０℃にて判定した
。臭気の判定は次の通りとした。(2) pH 5% by weight aqueous solution (3) 50% of water was added to 0.5% of the odor sample, and judgment was made at a temperature of 50°C. The odor was judged as follows.
Ａ ： 微 臭
Ｂ ： 少し臭気あり
Ｃ： 刺激臭があり
実施例 １
容ｆｆ１１０００ｍｊ！ステンレス製反応器に炭素数１
２〜１３平均分子量１９４の第１級アルコール（８産化
学社製、商品名、オキソコール０）３５６ｇ、触媒とし
て水酸化ナトリウム０．６ｇ、エチレンオキシド２４４
ｑを仕込み、温度１５０℃圧力６．０＃／ｄＧで反応さ
せた。得られた第１級アルコールのエチレンオキシド平
均３．０モル付加物に５０重量％乳酸水溶液２．８ｇを
添加し、よく撹拌した。得られた第１級アルコールエト
キシレート１モルを１１の撹拌槽に取り温度３０〜３５
℃に維持し、激しく撹拌しながらクロルスルホン酸１モ
ルを約１時間で撹拌槽内へ滴下し反応せしめた。クロル
スルホン酸の供給終了後撹拌槽内へ窒素ガスを供給し、
副生塩化水素ガスを除去し、ついで４０℃以下の温度に
維持しながら反応液を水酸化ナトリウム水溶液中に入れ
中和せしめ、第１級アルコールエトキシサルフェート水
溶液を得た。得られた第１級アルコールのエチレンオキ
シド平均３．０モルサルフェート水溶液について経時変
化の試験を行なった。結果は第１表に示すとおりであっ
た。A: Slight odor B: Slight odor C: Stimulating odor Example 1 Volume ff11000mj! 1 carbon in stainless steel reactor
2-13 356 g of primary alcohol with an average molecular weight of 194 (manufactured by Yasan Kagaku Co., Ltd., trade name, Oxocol 0), 0.6 g of sodium hydroxide as a catalyst, 244 g of ethylene oxide
q was charged and reacted at a temperature of 150° C. and a pressure of 6.0 #/dG. 2.8 g of a 50% by weight aqueous lactic acid solution was added to the obtained adduct of primary alcohol with 3.0 moles of ethylene oxide on average, and the mixture was thoroughly stirred. 1 mol of the obtained primary alcohol ethoxylate was placed in a stirring tank No. 11 and the temperature was 30-35.
While maintaining the temperature at °C and stirring vigorously, 1 mol of chlorosulfonic acid was dropped into the stirring tank over about 1 hour to cause a reaction. After the supply of chlorosulfonic acid is completed, nitrogen gas is supplied into the stirring tank,
After removing the by-product hydrogen chloride gas, the reaction solution was neutralized by placing it in an aqueous sodium hydroxide solution while maintaining the temperature at 40° C. or below, to obtain an aqueous solution of primary alcohol ethoxysulfate. The resulting aqueous solution of primary alcohol containing ethylene oxide and an average of 3.0 mol of sulfate was tested for changes over time. The results were as shown in Table 1.
比較例 １
容量１０００ｍ！ステンレス製反応器に炭素数１２〜１
３平均分子恐１９４の第１級アルコール（口座化学社製
、商品名、オキソコールｅ）３５６Ｑ、触媒として水酸
化ナトリウム０．６ｇ、エチレンオキシド２４４ｇを仕
込み、温度１５０℃圧力６．０に９／ｃｉＧで反応させ
た。得られた第１級アルコールのエチレンオキシド平均
３．０モル付加物に酢酸０．９０を添加し、よく撹伴し
た。Comparative example 1 Capacity 1000m! Carbon number 12-1 in stainless steel reactor
A primary alcohol with a 3-average molecular weight of 194 (manufactured by Kaguchi Kagaku Co., Ltd., trade name, Oxocol e) 356Q, 0.6 g of sodium hydroxide and 244 g of ethylene oxide as catalysts were charged, and the temperature was 150°C and the pressure was 6.0 at 9/ciG. Made it react. 0.90% acetic acid was added to the obtained adduct of primary alcohol with 3.0 mol of ethylene oxide on average, and the mixture was thoroughly stirred.
得られた第１級アルコールエトキシレート１モルを１１
の撹拌槽に取り温度３０〜３５℃に維持し、激しく撹拌
しながらクロルスルホン酸１モルを約１時間で攪拌槽内
へ滴下し反応せしめた。クロルスルホン酸の供給終了後
撹拌槽内へ窒素ガスを供給し、副生塩化水素ガスを除去
し、ついで４０℃以下の温度に維持しながら反応液を水
酸化ナトリウム水溶液中に入れ中和せしめ、第１級アル
コールエトキシサルフェート水溶液を得た。得られた第
１級アルコールのエチレンオキシド平均３．０モルナル
フェート水溶液について経時変化の試験を行なった。結
果は第１表に示すとおりであった。1 mol of the obtained primary alcohol ethoxylate
The mixture was placed in a stirred tank, and the temperature was maintained at 30 to 35° C., and 1 mole of chlorosulfonic acid was dropped into the stirred tank over about 1 hour to cause a reaction while stirring vigorously. After the supply of chlorosulfonic acid was completed, nitrogen gas was supplied into the stirring tank to remove by-product hydrogen chloride gas, and then the reaction solution was neutralized by placing it in an aqueous sodium hydroxide solution while maintaining the temperature at 40°C or less, A primary alcohol ethoxysulfate aqueous solution was obtained. The resulting aqueous solution of primary alcohol ethylene oxide with an average of 3.0 molar nalphate was tested for changes over time. The results were as shown in Table 1.
第 １ 表
実施例 ２
容ｆｌｉｔ ＯＯＯｍＪステンレス製反応器に炭素数１
１〜１５平均分子１１２０２の第１級アルコール（三菱
化成社製、商品名、ダイヤドール・）３６２ｇ、触媒と
して水酸化ナトリウム０．６９、エチレンオキシド２３
８ｇを仕込み、温度１５０℃圧力６．Ｏｔ’ＪＪ／ｃｉ
Ｇで反応させた。得られた第１級アルコールのエチレン
オキシド平均３．０モル付加物に５０重量％乳酸水溶液
２．８ｇを添加し、よく撹伴した。得られた第１級アル
コールエトキシレート１モルを１１の撹拌槽に取り湿度
３０〜３５℃に維持し、激しく撹拌しながらクロルスル
ホン酸１モルを約１時間で撹拌槽内へ滴下し反応せしめ
た。クロルスルホン酸の供給終了後撹拌槽内へ窒素ガス
を供給し、副生塩化水素ガスを除去し、ついで４０℃以
下の温度に維持しながら反応液を水酸化ナトリウム水溶
液中に入れ中和せしめ、第１級アルコールエトキシサル
フェート水溶液を得た。得られた第１級アルコールのエ
チレンオキシド平均３．０モルサルフェート水溶液につ
いて経時変化の試験を行なった。結果は第１表に示すと
おりであった。Table 1 Example 2 Volume flit OOOmJ stainless steel reactor with 1 carbon number
362 g of primary alcohol with an average molecular weight of 1 to 15 (manufactured by Mitsubishi Kasei Co., Ltd., trade name, Diadol), 0.69 sodium hydroxide as a catalyst, 23 ethylene oxide
Prepare 8g, temperature: 150℃, pressure: 6. Ot'JJ/ci
Reacted with G. 2.8 g of a 50% by weight aqueous lactic acid solution was added to the obtained adduct of primary alcohol with 3.0 mol of ethylene oxide on average, and the mixture was thoroughly stirred. 1 mol of the obtained primary alcohol ethoxylate was placed in a stirring tank No. 11, the humidity was maintained at 30 to 35°C, and 1 mol of chlorosulfonic acid was dropped into the stirring tank over about 1 hour while vigorously stirring to cause a reaction. . After the supply of chlorosulfonic acid was completed, nitrogen gas was supplied into the stirring tank to remove by-product hydrogen chloride gas, and then the reaction solution was neutralized by placing it in an aqueous sodium hydroxide solution while maintaining the temperature at 40°C or less, A primary alcohol ethoxysulfate aqueous solution was obtained. The resulting aqueous solution of primary alcohol containing ethylene oxide and an average of 3.0 mol of sulfate was tested for changes over time. The results were as shown in Table 1.
比較例 ２
容量１０００ｒｒ＋ｊ！ステンレス製反応器に炭素数１
１〜１５平均分子慴２０２の第１級アルコール（三菱化
成社製、商品名、ダイヤドール＠）３６２ｇ、触媒とし
て水酸化ナトリウム０．６ｇ、エチレンオキシド２３８
ｇを仕込み、温度１５０℃圧力６．０ｋｇ／ｉＧで反応
させた。得られた第１級アルコールのエチレンオキシド
平均３．０モル付加物に８５重量％のリン酸水溶液０．
９Ｃ１を添加し、よく撹伴した。得られた第１扱アルコ
ールエトキシレート１モルを１夕の撹拌槽に取り温度３
ｏ〜３５℃に維持し、激しく撹拌しながらクロルスルホ
ン酸１モルを約１時間で撹拌々１ｖ内へ滴下し反応せし
めた。クロルスルホン酸の供給終了後撹拌槽内へ窒素ガ
スを供給し、副生塩化水素ガスを除去し、ついで４０℃
以下の温度に維持しながら反応液を水酸化ナトリウム水
溶液中に入れ中和せしめ、第１級アルコールエトキシサ
ルフェート水溶液を得た。得られた第１級アルコールの
エチレンオキシド平均３．０モルサルフェート水溶液に
ついて経時変化の試験を行なった。結果は第２表に示す
とおりであった。Comparative example 2 Capacity 1000rr+j! 1 carbon in stainless steel reactor
1 to 15 362 g of primary alcohol with an average molecular weight of 202 (manufactured by Mitsubishi Kasei Co., Ltd., trade name, Diadol@), 0.6 g of sodium hydroxide as a catalyst, 238 g of ethylene oxide
g was charged and reacted at a temperature of 150° C. and a pressure of 6.0 kg/iG. To the resulting adduct of primary alcohol with 3.0 mol of ethylene oxide on average, 0.0 mol of an 85% by weight aqueous phosphoric acid solution was added.
9C1 was added and stirred well. One mole of the obtained first alcohol ethoxylate was placed in a stirring tank overnight at a temperature of 3.
While maintaining the temperature at 0 to 35° C. and stirring vigorously, 1 mole of chlorosulfonic acid was added dropwise into the reactor over about 1 hour to cause a reaction. After the supply of chlorosulfonic acid was completed, nitrogen gas was supplied into the stirring tank to remove by-product hydrogen chloride gas, and then the temperature was heated to 40°C.
The reaction solution was neutralized in an aqueous sodium hydroxide solution while maintaining the temperature below to obtain an aqueous solution of primary alcohol ethoxysulfate. The resulting aqueous solution of primary alcohol containing ethylene oxide and an average of 3.0 mol of sulfate was tested for changes over time. The results were as shown in Table 2.
第 ２ 表
実施例 ３
容量１０００ｒｌｌＪ！ステンレス製反応器に炭素数１
２〜１３平均分子漬１９４の第１級アルコール（Ｓｈｅ
ｌＩ社製、商品名、ドパノール０）３５６ｇ、触媒とし
て水酸化ナトリウム０．６ｇ、エチレンオキシド２４４
ｑを仕込み、温度１５０℃圧力６．０に９／ｃＭＧで反
応させた。得られた第１級アルコールのエチレンオキシ
ド平均３．０モル付加物に５０重１％乳酸水溶液２．８
ｇを添加し、よく撹拌した。得られた第１級アルコール
エトキシレート１モルを１１の撹拌槽に取り温度３０〜
３５℃に維持し、激しく撹拌しながらクロルスルホン酸
１モルを約１時間で撹拌槽内へ滴下し反応せしめた。ク
ロルスルホン酸の供給終了後撹拌槽内へ窒素ガスを供給
し、副生塩化水素ガスを除去し、ついで４０℃以下の温
度に維持しながら反応液を水酸化ナトリウム水溶液中に
入れ中和せしめ、第１級アルコールエトキシサルフェー
ト水溶液を得た。得られた第１級アルコールのエチレン
オキシド平均３．０モルサルフェート水溶液について経
時変化の試験を行なった。結果は第３表に示すとおりで
あった。Table 2 Example 3 Capacity 1000rllJ! 1 carbon in stainless steel reactor
2-13 average molecular weight 194 primary alcohol (She
Manufactured by II, trade name, Dopanol 0) 356 g, sodium hydroxide 0.6 g as a catalyst, ethylene oxide 244
q was charged and reacted at a temperature of 150° C. and a pressure of 6.0 at a ratio of 9/cMG. To the obtained primary alcohol adduct with ethylene oxide of 3.0 mol on average, 50% by weight lactic acid aqueous solution 2.8% was added.
g and stirred well. 1 mol of the obtained primary alcohol ethoxylate was placed in a stirring tank No. 11 and the temperature was 30~30.
While maintaining the temperature at 35°C and stirring vigorously, 1 mole of chlorosulfonic acid was dropped into the stirring tank over about 1 hour to cause a reaction. After the supply of chlorosulfonic acid was completed, nitrogen gas was supplied into the stirring tank to remove by-product hydrogen chloride gas, and then the reaction solution was neutralized by placing it in an aqueous sodium hydroxide solution while maintaining the temperature at 40° C. or less, A primary alcohol ethoxysulfate aqueous solution was obtained. The obtained primary alcohol ethylene oxide sulfate aqueous solution with an average of 3.0 mol was tested for changes over time. The results were as shown in Table 3.
比較例 ３
容ｆｆ１１０００ｒｒｌステンレス製反応器に炭素数１
２〜１３平均分子量１９４の第１級アルコール（Ｓｈｅ
ＩＩ社製、商品名、ドパノール［Ｆ］）３５６ｇ、触媒
として水酸化ナトリウム０．６ｑ、エチレンオキシド２
４４ｇを仕込み、温度１５０℃圧力６．０に９／ｃｉＧ
で反応させた。得られた第１級アルコールのエチレンオ
キシド平均３．０モル付加物に５０重量％硫酸水溶液１
．５９を添加し、よく撹拌した。得られた第１級アルコ
ールエトキシレート１モルを１１の撹拌槽に取り温度３
０〜３５℃に維持し、激しく撹拌しながらクロルスルホ
ン酸１モルを約１時間で撹拌槽内へ滴下し反応せしめた
。クロルスルホン酸の供給終了後撹拌槽内へ窒素ガスを
供給し、ｎ１生塩化水素ガスを除去し、ついで４０℃以
下の温度に維持しながら反応液を水酸化ナトリウム水溶
液中に入れ中和せしめ、第１級アルコールエトキシサル
フェート水溶液を得た。得られた第１級アルコールのエ
チレンオキシド平均３．０モルサルフェート水溶液につ
いて経時変化の試験を行なった。結果は第３表に示すと
おりであった。Comparative example 3 1 carbon number in a stainless steel reactor with a capacity of ff11000rrl
2-13 Primary alcohol with an average molecular weight of 194 (She
II company, trade name, Dopanol [F]) 356g, sodium hydroxide 0.6q as a catalyst, ethylene oxide 2
Pour 44g into 9/ciG at a temperature of 150℃ and a pressure of 6.0.
I reacted with Add 1 part of a 50% by weight aqueous sulfuric acid solution to the obtained adduct of primary alcohol with 3.0 mol of ethylene oxide on average.
．． 59 was added and stirred well. 1 mole of the obtained primary alcohol ethoxylate was placed in a stirring tank of 11 and the temperature was 3.
While maintaining the temperature at 0 to 35°C and stirring vigorously, 1 mole of chlorosulfonic acid was dropped into the stirring tank over about 1 hour to cause a reaction. After the supply of chlorosulfonic acid was completed, nitrogen gas was supplied into the stirring tank to remove the n1 raw hydrogen chloride gas, and then the reaction solution was neutralized by placing it in an aqueous sodium hydroxide solution while maintaining the temperature at 40°C or less, A primary alcohol ethoxysulfate aqueous solution was obtained. The resulting aqueous solution of primary alcohol containing ethylene oxide and an average of 3.0 mol of sulfate was tested for changes over time. The results were as shown in Table 3.
第 ３ 表
実施例 ４
容ｆｆ１１０００ｒｒ＋ｊ！ステンレス製反応器に炭素
数１２〜１３平均分子量１９４の第１級アルコール（８
産化学社製、商品名、オキソコール［相］）３５６ｇ、
触媒として水酸化カリウム１．ｏ９、エチレンオキシド
２４４９を仕込み、温度１５０℃、圧力６．０Ｋｇ／ｃ
ｊＧで反応させた。得られた第１級アルコールのエチレ
ンオキシド平均３．０モル付加物に５０重量％乳酸水溶
液３．１９を添加し、よく撹拌した。得られた第１級ア
ルコールエトキシレート１モルを１１の撹拌槽に取り温
度３０〜３５℃に維持し、激しく撹拌しながらクロルス
ルホンＭ１モルを約１時間で撹拌槽内へ滴下し反応せし
めた。クロルスルホン酸の供給終了後撹拌槽内へ窒素ガ
スを供給し、副生塩化水素ガスを除去し、ついで４０℃
以下の温度に維持しながら反応液を水酸化ナトリウム水
溶液中に入れ中和せしめ、第１級アルコールエトキシサ
ルフェート水溶液を得た。得られた第１級アルコールの
エチレンオキシド平均３．０モルサルフェート水溶液に
ついて経時変化の試験を行なった。結果は第４表に示す
とおりであった。Table 3 Example 4 Volume ff11000rr+j! A primary alcohol with a carbon number of 12 to 13 and an average molecular weight of 194 (8
Manufactured by Sankagaku Co., Ltd., trade name, oxocol [phase]) 356 g,
Potassium hydroxide as a catalyst1. o9, charged with ethylene oxide 2449, temperature 150℃, pressure 6.0Kg/c
The reaction was carried out with jG. To the obtained adduct of primary alcohol with ethylene oxide of 3.0 mol on average, 3.19 g of a 50% by weight aqueous lactic acid solution was added and stirred well. One mole of the obtained primary alcohol ethoxylate was placed in a stirring tank No. 11, and the temperature was maintained at 30 to 35°C, and while vigorously stirring, 1 mole of chlorsulfone M was dropped into the stirring tank over about 1 hour to cause a reaction. After the supply of chlorosulfonic acid was completed, nitrogen gas was supplied into the stirring tank to remove by-product hydrogen chloride gas, and then the temperature was heated to 40°C.
The reaction solution was neutralized in an aqueous sodium hydroxide solution while maintaining the temperature below to obtain an aqueous solution of primary alcohol ethoxysulfate. The resulting aqueous solution of primary alcohol containing ethylene oxide and an average of 3.0 mol of sulfate was tested for changes over time. The results were as shown in Table 4.
比較例 ４
容量１０００ｍ！ステンレス製反応器に炭素数１２〜１
３平均分子量１９４の第１級アルコール（８産化学社製
、商品名、オキソコールの）３５６ｇ、触媒として水酸
化カリウム１．ＯＱ、エチレンオキシド２４４ｇを仕込
み、温度１５０℃、圧力６．０Ｋｇ／ｃｉＧで反゛応さ
せた。得られた第１級アルコールのエチレンオキシド平
均３．０モル付加物に酢酸１．１０を添加し、よく撹拌
した。Comparative example 4 Capacity 1000m! Carbon number 12-1 in stainless steel reactor
356 g of primary alcohol with an average molecular weight of 194 (manufactured by Yasan Kagaku Co., Ltd., trade name: Oxocol), 1.0 g of potassium hydroxide as a catalyst. OQ and 244 g of ethylene oxide were charged and reacted at a temperature of 150° C. and a pressure of 6.0 Kg/ciG. 1.10 mol of acetic acid was added to the obtained adduct of primary alcohol with ethylene oxide on average of 3.0 mol, and the mixture was thoroughly stirred.
得られた第１級アルコールエトキシレート１モルを１１
の撹拌槽に取り温度３０〜３５℃に維持し、激しく撹拌
しながらクロルスルホン１１１１モルを約１時間で撹拌
槽内へ滴下し反応せしめた。クロルスルホン酸の供給終
了後撹拌槽内へ窒素ガスを供給し、副生塩化水素ガスを
除去し、ついで４０℃以下の温度に維持しながら反応液
を水酸化ナトリウム水溶液中に入れ中和せしめ、第１級
アルコールエトキシサルフェート水溶液を得た。得られ
た第１級アルコールのエチレンオキシド平均３．０モル
サルフェート水溶液について経時変化の試験を行なった
。結果は第４表に示すとおりであった。1 mol of the obtained primary alcohol ethoxylate
The mixture was placed in a stirred tank, and the temperature was maintained at 30 to 35°C, and 1111 moles of chlorsulfone was dropped into the stirred tank over about 1 hour to cause a reaction while stirring vigorously. After the supply of chlorosulfonic acid was completed, nitrogen gas was supplied into the stirring tank to remove by-product hydrogen chloride gas, and then the reaction solution was neutralized by placing it in an aqueous sodium hydroxide solution while maintaining the temperature at 40°C or less, A primary alcohol ethoxysulfate aqueous solution was obtained. The resulting aqueous solution of primary alcohol containing ethylene oxide and an average of 3.0 mol of sulfate was tested for changes over time. The results were as shown in Table 4.
第 ４ 表
実施例 ５
容ｆｆ１１０００ｍｊ！ステンレス製反応器に炭素数１
２〜１３平均分子量１９４の第１級アルコール（８産化
学社製、商品名、オキソコール８）１９６ｇ、触媒とし
て水酸化ナトリウム０．６ｇ、エチレンオキシド４０４
ｇを仕込み、温度１５０℃圧力６．Ｏｆ（ｇ／ｃ！ｉＧ
で反応させた。得られた第１級アルコールのエチレンオ
キシド平均９．０モル付加物に５０重１％乳酸水溶液２
．８ｇを添加し、よく撹拌した。得られた第１級アルコ
ールエトキシレート１モルを１１のｉｔ−￥槽に取り温
度３５〜４５℃に維持し、激しく撹拌しながらクロルス
ルホン酸１モルを約１時間で撹拌槽内へ滴下し反応せし
めた。クロルスルホン酸の供給終了後撹拌槽内へ窒素ガ
スを供給し、副生塩化水素ガスを除去し、ついで４０℃
以下の温度に維持しながら反応液を水酸化ナトリウム水
溶液中に入れ中和せしめ、第１級アルコールエトキシサ
ルフェート水溶液を得た。得られた第１級アルコールの
エチレンオキシド平均９．０モルサルフェート水溶液に
ついて経時変化の試験を行なった。結果は第５表に示す
とおりであった。Table 4 Example 5 Volume ff11000mj! 1 carbon in stainless steel reactor
2-13 196 g of primary alcohol with an average molecular weight of 194 (manufactured by Yasan Kagaku Co., Ltd., trade name, Oxocol 8), 0.6 g of sodium hydroxide as a catalyst, 404 g of ethylene oxide
g, temperature 150℃ and pressure 6. Of(g/c!iG
I reacted with To the obtained primary alcohol adduct with ethylene oxide on average 9.0 mol, 50% by weight lactic acid aqueous solution 2 was added.
．． 8g was added and stirred well. 1 mol of the obtained primary alcohol ethoxylate was placed in a No. 11 IT tank, the temperature was maintained at 35-45°C, and 1 mol of chlorosulfonic acid was added dropwise into the stirring tank over about 1 hour while stirring vigorously to react. I forced it. After the supply of chlorosulfonic acid was completed, nitrogen gas was supplied into the stirring tank to remove by-product hydrogen chloride gas, and then the temperature was heated to 40°C.
The reaction solution was neutralized in an aqueous sodium hydroxide solution while maintaining the temperature below to obtain an aqueous solution of primary alcohol ethoxysulfate. The obtained primary alcohol ethylene oxide sulfate aqueous solution with an average of 9.0 mol was tested for changes over time. The results were as shown in Table 5.
比較例 ５
容ｆｆ１１０００ｍ１ステンレス製反応器に炭素数１２
〜１３平均分子量１９４の第１級アルコール（口座化学
社製、商品名、オキソコール０）１９６ｑ、触媒として
水酸化ナトリウム０．６ｑ、エチレンオキシド４０４ｑ
を仕込み、温度１５０℃圧力６．ＯＫ’Ｊ／ｃｔｉＧで
反応させた。得られた第１級アルコールのエチレンオキ
シド平均９．０モル付加物に酢酸０．９ｇを添加し、よ
く撹伴した。Comparative example 5 Stainless steel reactor with a capacity of 11,000 m1 and a carbon number of 12
~13 Primary alcohol with an average molecular weight of 194 (manufactured by Kakuto Kagaku Co., Ltd., trade name, Oxocol 0) 196q, sodium hydroxide 0.6q as a catalyst, ethylene oxide 404q
6. Reaction was performed with OK'J/ctiG. 0.9 g of acetic acid was added to the obtained primary alcohol adduct with ethylene oxide on average of 9.0 mol, and the mixture was thoroughly stirred.
（ｑられた第１級アルコールエトキシレート１モルを１
Ｊｌの撹拌槽に取り温度３５〜４５℃に維持し、激しく
撹拌しながらクロルスルホン酸１モルを約１時間で撹拌
槽内へ滴下し反応せしめた。クロルスルホン酸の供給終
了後撹拌槽内へ窒素ガスを供給し、副生塩化水素ガスを
除去し、ついで４０℃以下の温度に維持しながら反応液
を水酸化ナトリウム水溶液中に入れ中和せしめ、第１級
アルコールエトキシサルフェート水溶液を得た。得られ
た第１級アルコールのエチレンオキシド平均９．０モル
サルフェート水溶液について経時変化の試験を行なった
。結果は第５表に示すとおりであった。(1 mole of the q primary alcohol ethoxylate is
The mixture was placed in a Jl stirring tank, and the temperature was maintained at 35 to 45°C, and 1 mole of chlorosulfonic acid was dropped into the tank over about 1 hour to cause a reaction while stirring vigorously. After the supply of chlorosulfonic acid was completed, nitrogen gas was supplied into the stirring tank to remove by-product hydrogen chloride gas, and then the reaction solution was neutralized by placing it in an aqueous sodium hydroxide solution while maintaining the temperature at 40°C or less, A primary alcohol ethoxysulfate aqueous solution was obtained. The obtained primary alcohol ethylene oxide sulfate aqueous solution with an average of 9.0 mol was tested for changes over time. The results were as shown in Table 5.
第 ５ 表
実施例 ６
容ｆｆｉｌｏｏｏｍｊ！ステンレス製反応器に炭素数１
２〜１３平均分子量１９４の第１級アルコール（口座化
学社製、商品名、オキソコール０）３５６ｇ、触媒とし
て水酸化ナトリウム０．６Ｑ、エチレンオキシド２４４
ｇを仕込み、温度１５０℃圧力６．０に９／ｃｉＧで反
応させた。得られた第１級アルコールのエチレンオキシ
ド平均３．０モル付加物にキョワード６００ＢＵＰＳ１
２ｑ添加し８０℃で３０分間撹拌した後、ケイソウ土で
プレコートした口過器へ移し、触媒を吸着したキヨワー
ド６００ＰＵＰＳを除去した。つぎに口過したエチレン
オキシド平均３モル付加物へ５０１ｔ％乳酸ナトリウム
水溶液３．５ｇを添加し、よく撹伴した。得られた乳酸
ナトリウムを含有する第１級アルコールエトキシレート
１モルを１１の撹拌槽に取り温度３０〜３５℃に維持し
、激しく撹拌しながらクロルスルホン酸１モルを約１時
間で撹拌槽内へ滴下し反応せしめた。クロルスルホン酸
の供給終了後撹拌槽内へ窒素ガスを供給し、副生塩化水
素ガスを除去し、ついで４０℃以下の温度に維持しなが
ら反応液を水酸化ナトリウム水溶液中に入れ中和せしめ
、第１級アルコールエトキシサルフェート水溶液を得た
。１ｑられた第１級アルコールのエチレンオキシド平均
３．０モルサルフェート水溶液について経時変化の試験
を行なった。Table 5 Example 6 ffilooomj! 1 carbon in stainless steel reactor
2-13 356 g of primary alcohol with an average molecular weight of 194 (manufactured by Kaguchi Kagaku Co., Ltd., trade name, Oxocol 0), 0.6 Q of sodium hydroxide as a catalyst, 244 g of ethylene oxide
g was charged and reacted at a temperature of 150° C. and a pressure of 6.0 at a rate of 9/ciG. Kyoward 600 BUPS1 was added to the obtained primary alcohol adduct with 3.0 moles of ethylene oxide on average.
After adding 2q and stirring at 80°C for 30 minutes, the mixture was transferred to a filter pre-coated with diatomaceous earth to remove Kyoward 600 PUPS that had adsorbed the catalyst. Next, 3.5 g of a 501 t% sodium lactate aqueous solution was added to the average 3 mole adduct of ethylene oxide which had been passed through the mouth, and the mixture was thoroughly stirred. 1 mol of the obtained primary alcohol ethoxylate containing sodium lactate was placed in a stirring tank No. 11, and the temperature was maintained at 30 to 35°C, and 1 mol of chlorosulfonic acid was poured into the stirring tank in about 1 hour while stirring vigorously. It was added dropwise to react. After the supply of chlorosulfonic acid was completed, nitrogen gas was supplied into the stirring tank to remove by-product hydrogen chloride gas, and then the reaction solution was neutralized by placing it in an aqueous sodium hydroxide solution while maintaining the temperature at 40°C or less, A primary alcohol ethoxysulfate aqueous solution was obtained. An aqueous solution of 1q primary alcohol containing ethylene oxide and an average of 3.0 mol of sulfate was tested for changes over time.
結果は第６表に示すとおりであった。The results were as shown in Table 6.
比較例 ６
容ｆｆｉｌｏｏｏｍ１ステンレス製反応器に炭素数１２
〜１３平均分子量１９４の第１級アルコールＸ日産化学
社製、商品名、オキソコール０）３５６つ、触媒として
水酸化ナトリウム０．６Ｑ、エチレンオキシド２４４ｑ
を仕込み、温度１５０℃圧力６．０に９／ｃｒＡＧで反
応させた。得られた第１級アルコールのエチレンオキシ
ド平均３．０モル付加物にキヨワード６００８ｔＪＰＳ
１２Ｑ添加しｓｏ’ｃで３０分間撹拌した後、ケイソウ
土でプレコートした口過器へ移し、触媒を吸着したキョ
ワード６００ＰＵＰＳを除去した。つぎに口過したエチ
レンオキシド平均３モル付加物を１１の撹拌槽に取り温
度３０〜３５℃に維持し、激しく撹ＩＴ−しながらクロ
ルスルホン酸１モルを約１時間で撹拌槽内へ滴下し反応
せしめた。クロルスルホン酸の供給終了後撹拌槽内へ窒
素ガスを供給し、副生塩化水素ガスを除去し、ついで４
０°Ｃ以下の温度に維持しながら反応液を水酸化すｌ〜
リウム水溶液中に入れ中和せしめ、第１級アルコールエ
トキシサルフェート水溶液を得た。得られた第１級アル
コールのエチレンオキシド平均３．０モルサルフェート
水溶液について経時変化の試験を行なった。Comparative Example 6 Volume ffilooom 1 stainless steel reactor with 12 carbon atoms
-13 Primary alcohol with an average molecular weight of 194
was charged and reacted at a temperature of 150° C. and a pressure of 6.0 with 9/crAG. Kiyoward 6008tJPS was added to the obtained primary alcohol adduct with 3.0 mol of ethylene oxide on average.
After adding 12Q and stirring for 30 minutes at SO'C, the mixture was transferred to a filter pre-coated with diatomaceous earth to remove Kyoward 600 PUPS that had adsorbed the catalyst. Next, the passed ethylene oxide adduct with an average of 3 moles was taken into a stirring tank No. 11, and the temperature was maintained at 30 to 35°C, and 1 mole of chlorosulfonic acid was added dropwise into the stirring tank over about 1 hour to react while stirring vigorously. I forced it. After the supply of chlorosulfonic acid was completed, nitrogen gas was supplied into the stirring tank to remove by-product hydrogen chloride gas, and then
The reaction solution is hydroxylated while maintaining the temperature below 0°C.
The mixture was neutralized in an aqueous solution of aluminum to obtain an aqueous solution of primary alcohol ethoxysulfate. The resulting aqueous solution of primary alcohol containing ethylene oxide and an average of 3.0 mol of sulfate was tested for changes over time.
結果は第６表に示すとおりであった。The results were as shown in Table 6.
第 ６ 表
（発明の効果）
第１級アルコール類とエチレンオキシドとを反応させて
得られた第１級アルコール類エトキシレートに乳酸およ
び／または乳酸塩を含有させて後、硫酸化して得られた
第１級アルコール類エトキシサルフェートは、経時変化
にる臭気の発生が極めて少なくなる効果を発揮すること
がわかった。さらに得られたアルコール類エトキシサル
フェートは界面活性剤として広い分野で使用できるもの
である。Table 6 (Effects of the Invention) Primary alcohol ethoxylates obtained by reacting primary alcohols with ethylene oxide contain lactic acid and/or lactate, and then sulfate. It has been found that primary alcohol ethoxysulfate exhibits the effect of extremely reducing the generation of odor over time. Furthermore, the obtained alcohol ethoxysulfate can be used as a surfactant in a wide range of fields.
Claims (7)
せて得られる第１級アルコールエトキシレートに乳酸お
よび／または乳酸塩を含有させ、ついで硫酸化すること
を特徴とする安定化した第１級アルコールエトキシサル
フェート。(1) Stabilized primary alcohol ethoxylate obtained by reacting a primary alcohol with ethylene oxide, containing lactic acid and/or lactate, and then sulfating the primary alcohol ethoxylate. Sulfate.
である特許請求の範囲第１項記載の第１級アルコールエ
トキシサルフェート。(2) The primary alcohol ethoxy sulfate according to claim 1, wherein the primary alcohol is a saturated aliphatic primary alcohol.
ルである特許請求の範囲第１項記載の第１級アルコール
エトキシサルフェート。(3) The primary alcohol ethoxy sulfate according to claim 1, wherein the primary alcohol is an unsaturated aliphatic primary alcohol.
ルコールである特許請求の範囲第１項記載の第１級アル
コールエトキシサルフェート。(4) The primary alcohol ethoxy sulfate according to claim 1, wherein the primary alcohol is a branched saturated aliphatic primary alcohol.
範囲第１項記載の第１級アルコールエトキシサルフェー
ト。(5) The primary alcohol ethoxy sulfate according to claim 1, wherein the lactate is an alkali metal salt of lactic acid.
１項記載の第１級アルコールエトキシサルフェート。(6) The primary alcohol ethoxy sulfate according to claim 1, wherein the lactate is sodium lactate.
項記載の第１級アルコールエトキシサルフェート。(7) Claim 1 in which the lactate is potassium lactate
Primary alcohol ethoxy sulfate as described in .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61183351A JPS6339852A (en) | 1986-08-06 | 1986-08-06 | Stabilized primary alcohol ethoxysulfate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61183351A JPS6339852A (en) | 1986-08-06 | 1986-08-06 | Stabilized primary alcohol ethoxysulfate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6339852A true JPS6339852A (en) | 1988-02-20 |
| JPH0512341B2 JPH0512341B2 (en) | 1993-02-17 |
Family
ID=16134219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61183351A Granted JPS6339852A (en) | 1986-08-06 | 1986-08-06 | Stabilized primary alcohol ethoxysulfate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6339852A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006117571A (en) * | 2004-10-20 | 2006-05-11 | Kao Corp | Method for producing anionic surfactant composition |
| WO2014034681A1 (en) * | 2012-08-31 | 2014-03-06 | ライオン株式会社 | Method for producing polyoxyethylene alkyl ether sulfate |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5143483A (en) * | 1974-10-07 | 1976-04-14 | Santo Tekkosho Kk | Dofuryono eashiiruhoho |
| JPS56112931A (en) * | 1980-02-12 | 1981-09-05 | Sanyo Chem Ind Ltd | Polyol composition |
-
1986
- 1986-08-06 JP JP61183351A patent/JPS6339852A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5143483A (en) * | 1974-10-07 | 1976-04-14 | Santo Tekkosho Kk | Dofuryono eashiiruhoho |
| JPS56112931A (en) * | 1980-02-12 | 1981-09-05 | Sanyo Chem Ind Ltd | Polyol composition |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006117571A (en) * | 2004-10-20 | 2006-05-11 | Kao Corp | Method for producing anionic surfactant composition |
| JP4744120B2 (en) * | 2004-10-20 | 2011-08-10 | 花王株式会社 | Method for producing anionic surfactant composition |
| WO2014034681A1 (en) * | 2012-08-31 | 2014-03-06 | ライオン株式会社 | Method for producing polyoxyethylene alkyl ether sulfate |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0512341B2 (en) | 1993-02-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4464292A (en) | Mixed ethoxylated alcohol/ethoxy sulfate surfactants and synthetic detergents incorporating the same | |
| US3320292A (en) | Preparation of sulfonated fatty acid ester surface-active agents | |
| EP0287885A1 (en) | Process for the preparation of serine-N,N-diacetic acid and its derivatives | |
| US2130362A (en) | Detergent and method of preparation | |
| US5117032A (en) | Process for making glycerol ether sulfates | |
| US4737314A (en) | Stabilized alkylene oxide adduct containing lactic acid or a lactate | |
| GB2088863A (en) | Novel Alkyl-polyoxyalkylene Carboxylate Surfactants | |
| US3959186A (en) | Process for manufacturing detergent builders | |
| JPH0253417B2 (en) | ||
| JPS6339852A (en) | Stabilized primary alcohol ethoxysulfate | |
| JPS61186337A (en) | Stabilized secondary alcohol ethoxylate | |
| US3426077A (en) | Low foaming biodegradable surfactant compositions | |
| JPH0517223B2 (en) | ||
| US2091956A (en) | Sulphuric acid esters of higher glycols | |
| US2684969A (en) | Process for the preparation of hydroxy amides from hydroxy amines and carboxylic acid halides | |
| JPH05222396A (en) | Concentrated liquid detergent composition | |
| JPS62255468A (en) | Stabilized ethoxysulfate of phenolic compound | |
| JPS61246140A (en) | Stabilized alkylene oxide adduct to polyhydric alcohol | |
| JPS61197536A (en) | Stabilized alkylene oxide addition product | |
| JPS61218544A (en) | Stabilized phenol alkylene oxide adduct | |
| JPS6339993A (en) | Liquid detergent composition | |
| US2395971A (en) | Detergent cx | |
| JPH0726114B2 (en) | Liquid detergent composition | |
| US3676372A (en) | Hydrogenated olefin sulfonate-fatty acid amide detergent compositions | |
| JPH0631403B2 (en) | Liquid detergent composition |