JPH06116219A - Production of fatty acid diethanolamide with low diethanolamine content - Google Patents
Production of fatty acid diethanolamide with low diethanolamine contentInfo
- Publication number
- JPH06116219A JPH06116219A JP22645691A JP22645691A JPH06116219A JP H06116219 A JPH06116219 A JP H06116219A JP 22645691 A JP22645691 A JP 22645691A JP 22645691 A JP22645691 A JP 22645691A JP H06116219 A JPH06116219 A JP H06116219A
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- diethanolamine
- carbonate
- acid diethanolamide
- low
- 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
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 46
- 239000000194 fatty acid Substances 0.000 title claims abstract description 46
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 46
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 44
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 15
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000012535 impurity Substances 0.000 claims abstract description 7
- 125000005910 alkyl carbonate group Chemical group 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 6
- 125000002252 acyl group Chemical group 0.000 claims abstract description 4
- 150000004671 saturated fatty acids Chemical group 0.000 claims abstract description 3
- 150000004670 unsaturated fatty acids Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract 3
- -1 acyl carbonate Chemical compound 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 abstract description 10
- 239000000203 mixture Substances 0.000 abstract description 8
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 238000009472 formulation Methods 0.000 abstract description 3
- 230000008719 thickening Effects 0.000 abstract description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 abstract description 2
- 238000002845 discoloration Methods 0.000 abstract 1
- 231100000331 toxic Toxicity 0.000 abstract 1
- 230000002588 toxic effect Effects 0.000 abstract 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 239000003240 coconut oil Substances 0.000 description 10
- 235000019864 coconut oil Nutrition 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000004040 coloring Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- UDSAIICHUKSCKT-UHFFFAOYSA-N bromophenol blue Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2S(=O)(=O)O1 UDSAIICHUKSCKT-UHFFFAOYSA-N 0.000 description 4
- 239000004359 castor oil Substances 0.000 description 4
- 235000019438 castor oil Nutrition 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000003760 tallow Substances 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- BGAWVNPRXDHVLX-UHFFFAOYSA-N CCCCCCCCCCCC(=O)CCOC(=O)O Chemical compound CCCCCCCCCCCC(=O)CCOC(=O)O BGAWVNPRXDHVLX-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000003346 palm kernel oil Substances 0.000 description 2
- 235000019865 palm kernel oil Nutrition 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 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
- POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- BLJQPKYBLXZZIX-UHFFFAOYSA-N C(OC(CCCCCCCCCCC)=O)(OC)=O Chemical compound C(OC(CCCCCCCCCCC)=O)(OC)=O BLJQPKYBLXZZIX-UHFFFAOYSA-N 0.000 description 1
- 229940123150 Chelating agent Drugs 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- 208000001840 Dandruff Diseases 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 239000004909 Moisturizer Substances 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 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
- 235000019482 Palm oil Nutrition 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 229960000458 allantoin Drugs 0.000 description 1
- 229940069521 aloe extract Drugs 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000004332 deodorization Methods 0.000 description 1
- SMVRDGHCVNAOIN-UHFFFAOYSA-L disodium;1-dodecoxydodecane;sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC SMVRDGHCVNAOIN-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940009662 edetate Drugs 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- MYZBNECHXQEZNC-UHFFFAOYSA-N ethoxycarbonyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC(=O)OCC MYZBNECHXQEZNC-UHFFFAOYSA-N 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229960004949 glycyrrhizic acid Drugs 0.000 description 1
- 235000019410 glycyrrhizin Nutrition 0.000 description 1
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 description 1
- 229920002674 hyaluronan Polymers 0.000 description 1
- 229960003160 hyaluronic acid Drugs 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- HLERILKGMXJNBU-UHFFFAOYSA-N norvaline betaine Chemical compound CCCC(C([O-])=O)[N+](C)(C)C HLERILKGMXJNBU-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
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- BTSZTGGZJQFALU-UHFFFAOYSA-N piroctone olamine Chemical compound NCCO.CC(C)(C)CC(C)CC1=CC(C)=CC(=O)N1O BTSZTGGZJQFALU-UHFFFAOYSA-N 0.000 description 1
- 229940081510 piroctone olamine Drugs 0.000 description 1
- 210000002826 placenta Anatomy 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- SUBJHSREKVAVAR-UHFFFAOYSA-N sodium;methanol;methanolate Chemical compound [Na+].OC.[O-]C SUBJHSREKVAVAR-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229940104261 taurate Drugs 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229940043810 zinc pyrithione Drugs 0.000 description 1
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、ジエタノールアミン含
量が低く、経時着色の少ない脂肪酸ジエタノールアミド
の製造方法に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing a fatty acid diethanolamide having a low content of diethanolamine and little coloring with time.
【０００２】[0002]
【従来の技術】脂肪酸ジエタノールアミド型界面活性剤
は、以前から公知である界面活性剤であり、他の界面活
性剤に配合する事により、その界面活性剤に優れた起泡
力、浸透力、洗浄力、増粘力を与え、また、毒性がきわ
めて低く、生分解性が良いことからシャンプー、台所洗
剤等の化粧品、トイレタリー用品には、不可欠な成分と
して当業者においては古くから使用されている。BACKGROUND OF THE INVENTION Fatty acid diethanolamide type surfactants have been known for a long time, and by blending with other surfactants, excellent foaming power, penetrating power, It has been used by cosmeticians for a long time as an indispensable ingredient in cosmetics such as shampoos and kitchen detergents, and toiletry products, since it provides detergency, thickening power, and has extremely low toxicity and good biodegradability. .
【０００３】[0003]
【発明が解決しようとする課題】しかしながら、脂肪酸
ジエタノールアミド型界面活性剤は、その製造に際し使
用するジエタノールアミンを不純物として２〜８％程度
含有する。このため、製品の外観が経時的に変化し、着
色が起きる場合が多い。However, the fatty acid diethanolamide type surfactant contains about 2 to 8% of diethanolamine used as an impurity in the production thereof as an impurity. As a result, the appearance of the product changes over time, and coloring often occurs.
【０００４】エタノールアミン類を除去する方法として
は、蒸留あるいはカラムによる分離精製などがある。し
かし、これらの除去法は脂肪酸ジエタノールアミド型界
面活性剤の物性上から充分な分離、除去が困難であった
り、多大なコスト増となる。また、特開平２−３００１
５３においては、無水酢酸による処理方法が提案されて
いるが、この方法では反応の構成上、使用する無水酢酸
と等モルの酢酸が副成する。この副成した酢酸は、減圧
下に加熱して取り除く事になるが現在の技術で十分に取
り除く事は困難である。その為残存する酢酸が悪臭の原
因となり、満足のいくジエタノールアミンの除去方法が
ないのが現状である。As a method for removing ethanolamines, there are distillation and separation and purification by a column. However, these removal methods make it difficult to sufficiently separate and remove the fatty acid diethanolamide type surfactant, and increase the cost significantly. In addition, JP-A-2-3001
In 53, a treatment method with acetic anhydride is proposed, but in this method, acetic anhydride used is by-produced in an equimolar amount due to the constitution of the reaction. This by-produced acetic acid is to be removed by heating under reduced pressure, but it is difficult to remove it sufficiently with the current technology. Therefore, the residual acetic acid causes a bad odor, and there is no satisfactory method for removing diethanolamine.
【０００５】[0005]
【課題を解決するための手段】本発明者らは、従来の脂
肪酸ジエタノールアミドの不純物であるジエタノールア
ミンの除去を行なうため鋭意研究を行なった結果、ジエ
タノールアミンを含む脂肪酸ジエタノールアミドにカー
ボネートを反応させる事により遊離酸を副成させること
なくジエタノールアミンが低減することを見い出し、本
発明を完成するに至った。即ち本発明は、一般式（Ｉ
Ｖ）[Means for Solving the Problems] As a result of intensive studies to remove diethanolamine, which is an impurity of conventional fatty acid diethanolamide, the present inventors have found that a fatty acid diethanolamide containing diethanolamine is reacted with a carbonate. The inventors have found that diethanolamine is reduced without forming a free acid as a by-product, and have completed the present invention. That is, the present invention has the general formula (I
V)
【化４】 （ＩＶ）で表されるジエタノールアミンと一般式（Ｉ
Ｉ）[Chemical 4] The diethanolamine represented by (IV) and the general formula (I
I)
【化５】 （ＩＩ）（式中Ｒ2 およびＲ3 は、炭素数１〜６のアル
キル基を表す。）で表されるアルキルカーボネートとを
反応させ、ジエタノールアミンのアシル化を行ない、一
般式（Ｖ）及び（ＶＩ）を生成させる事を利用してジエ
タノールアミンを低減するものである。[Chemical 5] (II) (in the formula, R 2 and R 3 represent an alkyl group having 1 to 6 carbon atoms) is reacted with an alkyl carbonate to diacylate diethanolamine, and then the general formulas (V) and (V VI) is utilized to reduce diethanolamine.
【化６】 （Ｖ） Ｒ3 ＯＨ （ＶＩ） また、アシル基を導入したカーボネート（ＩＩＩ）によ
る反応では[Chemical 6] (V) R 3 OH (VI) In addition, in the reaction with the carbonate (III) having an acyl group introduced,
【化７】 （ＩＩＩ）（式中Ｒ4 ＣＯは、炭素数６〜２２の飽和ま
たは不飽和のアシル基を表し、Ｒ5は、炭素数１〜６の
アルキル基を表す。）で表されるアシルカーボネートを
反応させ、ジエタノールアミンのアシル化を行ない、一
般式（ＶＩＩ）、（ＶＩＩＩ）及び二酸化炭素を生成さ
せる事を利用してジエタノールアミンを低減するもので
ある。[Chemical 7] An acyl carbonate represented by (III) (wherein R 4 CO represents a saturated or unsaturated acyl group having 6 to 22 carbon atoms, and R 5 represents an alkyl group having 1 to 6 carbon atoms). By reacting and acylating diethanolamine to generate general formulas (VII) and (VIII) and carbon dioxide, diethanolamine is reduced.
【化８】 （ＶＩＩ） Ｒ5 ＯＨ （ＶＩＩＩ）[Chemical 8] (VII) R 5 OH (VIII)
【０００６】本発明に用いられる脂肪酸ジエタノールア
ミドは、未反応ジエタノールアミンを含み、その構成脂
肪酸は炭素数６ないし２２の飽和または不飽和の脂肪酸
である。代表的な脂肪酸を例示すれば、ヤシ油脂肪酸、
パーム核油脂肪酸、ラウリン酸、ミリスチン酸、牛脂脂
肪酸、硬化牛脂脂肪酸、オレイン酸、ヒマシ油脂肪酸お
よび硬化ヒマシ油脂肪酸などである。The fatty acid diethanolamide used in the present invention contains unreacted diethanolamine, and its constituent fatty acid is a saturated or unsaturated fatty acid having 6 to 22 carbon atoms. Typical fatty acids are, for example, coconut oil fatty acid,
Palm kernel oil fatty acid, lauric acid, myristic acid, tallow fatty acid, hydrogenated tallow fatty acid, oleic acid, castor oil fatty acid, hydrogenated castor oil fatty acid and the like.
【０００７】本発明に使用されるアシルカーボネート
は、カルボン酸及びクロロ蟻酸エステルより簡単に調製
する事が可能であり、代表的なカーボネートを例示すれ
ば、ラウロイルエチルカーボネート、ラウロイルメチル
カーボネート，ミリストイルエチルカーボネート、ミリ
ストイルメチルカーボネート等単一組成の脂肪酸を原料
に使用する事も可能であるし、ヤシ油脂肪酸、パーム核
油脂肪酸、牛脂脂肪酸、硬化牛脂脂肪酸、ヒマシ油脂肪
酸、硬化ヒマシ油脂肪酸等を利用してカーボネートを調
製する事も可能である。ただし、使用するアシルカーボ
ネートの種類はこれらに限定されるものではない。The acyl carbonate used in the present invention can be easily prepared from a carboxylic acid and a chloroformate. Typical examples of the carbonate include lauroyl ethyl carbonate, lauroyl methyl carbonate and myristoyl ethyl carbonate. It is also possible to use a single composition fatty acid such as myristoyl methyl carbonate as a raw material, or use coconut oil fatty acid, palm kernel oil fatty acid, tallow fatty acid, hydrogenated tallow fatty acid, castor oil fatty acid, hydrogenated castor oil fatty acid, etc. It is also possible to prepare carbonates. However, the type of acyl carbonate used is not limited to these.
【０００８】本発明に使用される代表的なアルキルカー
ボネートを例示すればジメチルカーボネート、ジエチル
カーボネート、メチルエチルカーボネート等が挙げられ
る。ただし、使用するアルキルカーボネートの種類はこ
れらに限定されるものではない。Typical examples of the alkyl carbonate used in the present invention include dimethyl carbonate, diethyl carbonate and methyl ethyl carbonate. However, the type of alkyl carbonate used is not limited to these.
【０００９】また、カーボネートの添加量は、アシルカ
ーボネートの場合は、塩酸滴定で測定されるジエタノー
ルアミンの０．５倍モル〜１．５倍モルであることが好
ましい。０．５倍モル以下ではジエタノールアミンの残
存量が多く、１．５倍モル以上では経時的にアシルカー
ボネートより遊離酸が発生し好ましくない。アルキルカ
ーボネートの場合は塩酸滴定で測定されるジエタノール
アミンの０．２５倍モル以上であることが好ましい。
０．２５倍モル以下ではエタノールアミンの残存率が多
い。In the case of acyl carbonate, the amount of carbonate added is preferably 0.5 times to 1.5 times the mol of diethanolamine measured by hydrochloric acid titration. When it is 0.5 times or less, the residual amount of diethanolamine is large, and when it is 1.5 times or more, the free acid is generated from the acyl carbonate over time, which is not preferable. In the case of alkyl carbonate, it is preferably 0.25 times or more mol of diethanolamine as measured by hydrochloric acid titration.
When the amount is 0.25 times or less, the residual rate of ethanolamine is high.
【００１０】本発明界面活性剤は、界面活性剤工業で一
般的に使用されている他の界面活性剤と配合することが
できる。それらの界面活性剤としては、例えば脂肪酸石
けん高級アルコール硫酸エステル塩、ポリオキシエチレ
ン高級アルコール硫酸エステル塩、高級アルコールリン
酸エステル塩、ポリオキシエチレン高級アルコールリン
酸エステル塩，ポリオキシエチレン高級脂肪酸リン酸エ
ステル塩、スルホン化高級脂肪酸塩、高級アルコールス
ルホコハク酸エステル塩、アシルメチルタウレイト、Ｎ
−長鎖アシル−グルタミン酸塩、Ｎ−長鎖アシル−サル
コシン塩、Ｎ−長鎖アシル−Ｎ−アルキル−βアラニン
塩、アシルイセチオン酸塩、α−オレフィンスルホン酸
塩、などのアニオン界面活性剤、脂肪酸モノエタノール
アミド、ポリオキシエチレン脂肪酸モノエタノールアミ
ド等のノニオン界面活性剤、アルキルイミダゾリニウム
ベタイン、脂肪酸アミドプロピルベタイン型等の両性界
面活性剤、第４級アンモニウム塩型カチオン界面活性剤
等のカチオン界面活性剤等がある。The surfactants of this invention can be combined with other surfactants commonly used in the surfactant industry. Examples of these surfactants include fatty acid soap higher alcohol sulfate ester salt, polyoxyethylene higher alcohol sulfate ester salt, higher alcohol phosphate ester salt, polyoxyethylene higher alcohol phosphate ester salt, polyoxyethylene higher fatty acid phosphate salt. Ester salt, sulfonated higher fatty acid salt, higher alcohol sulfosuccinate salt, acylmethyl taurate, N
Anionic surfactant such as long-chain acyl-glutamate, N-long-chain acyl-sarcosine salt, N-long-chain acyl-N-alkyl-β-alanine salt, acyl isethionate, α-olefin sulfonate, fatty acid Nonionic surfactants such as monoethanolamide and polyoxyethylene fatty acid monoethanolamide, amphoteric surfactants such as alkylimidazolinium betaine and fatty acid amide propylbetaine type, cation interfaces such as quaternary ammonium salt type cationic surfactant There are activators etc.
【００１１】また、必要に応じて、グリコール類等の可
溶化剤、エステル油等のエモリエント剤、ヒアルロン
酸、キチン、キトサン等の保湿剤、アロエエキス、胎盤
抽出液等の細胞賦活剤、アラントイン、グリチルリチン
酸等の消炎剤、ジンクピリチオン、ピロクトンオラミン
等の抗フケ剤、エデト酸塩のようなキレート剤、ジブチ
ルヒドロキシトルエン、ビタミンＥのような酸化防止剤
及び殺菌剤、香料、色素なども加えることができる。If necessary, solubilizers such as glycols, emollients such as ester oils, moisturizers such as hyaluronic acid, chitin and chitosan, cell activating agents such as aloe extract and placenta extract, allantoin, Add anti-inflammatory agents such as glycyrrhizinic acid, anti-dandruff agents such as zinc pyrithione and piroctone olamine, chelating agents such as edetate, antioxidants and bactericides such as dibutylhydroxytoluene and vitamin E, fragrances and pigments. be able to.
【００１２】[0012]
【実施例】以下実施例により本発明をさらに詳細に説明
する。The present invention will be described in more detail with reference to the following examples.
【００１３】実施例１ ヤシ油脂肪酸メチルエステル（Ｃ8 8.2 ％、Ｃ10 6.8
％、Ｃ12 49.5 ％、Ｃ1417.7 ％、Ｃ16 8.4％、Ｃ18 2.
6％、Ｃ18 F1 5.8 ％、Ｃ18 F2 1.0 ％）２．２Ｋｇ、
ジエタノールアミン１．１Ｋｇ、ナトリウムメチラート
２８％メタノール溶液１８ｇを取り、８０℃まで昇温し
た後、徐々に減圧し、約３時間かけ１０ｍｍＨｇまで減
圧を行い、脱メタノールを行った。約３００ｇのメタノ
ールを除いた後、約１時間同一条件で熟成を行ない、粗
ヤシ油脂肪酸ジエタノールアミド３Ｋｇを得た。この反
応生成物をＢＰＢ（ブロムフェノールブルー）を指示薬
とし、０．１Ｎ塩酸で滴定した結果、ジエタノールアミ
ンの含有量は５．８％であった。ついで、この粗ヤシ油
脂肪酸ジエタノールアミド１Ｋｇにジメチルカーボネー
ト５５ｇ（対ジエタノールアミンモル比１．１倍モル）
を加え、６５℃に加熱して徐々に減圧し、約３時間かけ
１０ｍｍＨｇまで減圧にして、ジエタノールアミンのア
シル化を行った。このヤシ油脂肪酸ジエタノールアミド
のジエタノールアミン含量を前述の方法で測定したとこ
ろ、１．８％であった。また、フェノールフタレインを
指示薬とし、０．１Ｎ水酸化カリウム・エタノール液で
滴定した結果、遊離酸は検出されなかった。Example 1 Coconut oil fatty acid methyl ester (C 8 8.2%, C 10 6.8)
%, C 12 49.5%, C 14 17.7%, C 16 8.4%, C 18 2.
6%, C 18 F1 5.8%, C 18 F2 1.0%) 2.2 Kg,
1.1 kg of diethanolamine and 18 g of a 28% sodium methylate methanol solution were taken, heated to 80 ° C., gradually depressurized, and depressurized to 10 mmHg for about 3 hours to remove methanol. After removing about 300 g of methanol, the mixture was aged for about 1 hour under the same conditions to obtain 3 kg of crude coconut oil fatty acid diethanolamide. The reaction product was titrated with 0.1N hydrochloric acid using BPB (bromphenol blue) as an indicator, and as a result, the content of diethanolamine was 5.8%. Then, to 1 kg of this crude coconut oil fatty acid diethanolamide, 55 g of dimethyl carbonate (molar ratio of diethanolamine to 1.1 times mol) was added.
Was added, and the pressure was gradually reduced by heating to 65 ° C., and the pressure was reduced to 10 mmHg over about 3 hours to acylate diethanolamine. When the diethanolamine content of this coconut oil fatty acid diethanolamide was measured by the above-mentioned method, it was 1.8%. As a result of titration with 0.1N potassium hydroxide / ethanol solution using phenolphthalein as an indicator, no free acid was detected.
【００１４】実施例２ 実施例１で合成した粗ヤシ油脂肪酸ジエタノールアミド
１Ｋｇにラウロイルエチルカーボネート１７５ｇ（対ジ
エタノールアミンモル比１．１倍モル）を加え、６５℃
にて徐々に減圧し、約３時間かけ１０ｍｍＨｇまで減圧
を行い、ジエタノールアミンのアシル化を行った。この
もののジエタノールアミンの含量を測定したところ１．
３％であった。遊離酸は検出されなかった。Example 2 To 1 kg of the crude coconut oil fatty acid diethanolamide synthesized in Example 1, 175 g of lauroylethyl carbonate (molar ratio of diethanolamine to 1.1 times) was added, and the mixture was heated to 65 ° C.
The pressure was gradually reduced to 10 mmHg over about 3 hours to acylate diethanolamine. When the content of diethanolamine in this product was measured, 1.
It was 3%. No free acid was detected.
【００１５】実施例３ ジエタノールアミン３２８ｇ、水酸化ナトリウム２．５
ｇを取り、ヤシ油６６８ｇを仕込み、８０℃に加熱し、
３０ｍｍＨｇの減圧下で１時間反応させ、粗ヤシ油脂肪
酸ジエタノールアミド１０００ｇを得た。この反応生成
物をＢＰＢ（ブロムフェノールブルー）を指示薬とし、
０．１Ｎ塩酸で滴定した結果、ジエタノールアミンの含
有量は５．３％であった。この生成物１００ｇにジメチ
ルカーボネート５．５ｇ（対ジエタノールアミンモル比
１．２倍モル）を加え、６５℃に加熱して徐々に減圧
し、約３時間かけ１０ｍｍＨｇまで減圧にして、ジエタ
ノールアミンのアシル化を行った。このもののジエタノ
ールアミンの含量を測定したところ１．３％であった。
遊離酸は検出されなかった。Example 3 328 g of diethanolamine, 2.5 of sodium hydroxide
g, charge 668 g of palm oil, heat to 80 ° C,
The reaction was performed under a reduced pressure of 30 mmHg for 1 hour to obtain 1000 g of crude coconut oil fatty acid diethanolamide. This reaction product uses BPB (bromphenol blue) as an indicator,
As a result of titration with 0.1N hydrochloric acid, the content of diethanolamine was 5.3%. To 100 g of this product, 5.5 g of dimethyl carbonate (molar ratio of diethanolamine to 1.2 times) was added, heated to 65 ° C. and gradually depressurized, and reduced to 10 mmHg over about 3 hours to acylate diethanolamine. went. The content of diethanolamine in this product was measured and found to be 1.3%.
No free acid was detected.
【００１６】実施例４ 実施例３で合成した粗ヤシ油脂肪酸ジエタノールアミド
１００ｇにラウロイルエチルカーボネート１６ｇ（対ジ
エタノールアミンモル比１．１倍モル）を加え、６５℃
に加熱して徐々に減圧し、約３時間かけ１０ｍｍＨｇま
で減圧にして、ジエタノールアミンのアシル化を行なっ
た。このもののジエタノールアミンの含量を測定したと
ころ１．４％であった。遊離酸は検出されなかった。Example 4 To 100 g of crude coconut oil fatty acid diethanolamide synthesized in Example 3 was added 16 g of lauroylethyl carbonate (molar ratio of diethanolamine to 1.1 times), and the mixture was heated to 65 ° C.
Then, the pressure was gradually reduced by heating to 10 mmHg over about 3 hours to acylate the diethanolamine. The content of diethanolamine in this product was measured and found to be 1.4%. No free acid was detected.
【００１７】比較例１ （カーボネートでのアシル化処理を行なわない例）実施
例１のカーボネート添加前の反応生成物。Comparative Example 1 (Example in which Acylation Treatment with Carbonate is not Performed) Reaction product of Example 1 before addition of carbonate.
【００１８】比較例２ （カーボネートでのアシル化処理を行なわない例）実施
例３のカーボネート添加前の反応生成物。Comparative Example 2 (Example in which Acylation Treatment with Carbonate is not Performed) Reaction product of Example 3 before addition of carbonate.
【００１９】比較例３ （アシル化剤として無水酢酸を使用した例）実施例１の
カーボネート添加前の反応生成物１００ｇに無水酢酸
４．５ｇ（対ジエタノールアミンモル比０．８倍モル）
を加え、１時間攪拌した後、２０ｍｍＨｇの減圧下で８
０℃に１時間加熱して脱臭を行った。この操作中に褐色
に着色した。この物のジエタノールアミン含量を定量し
たところ１．４％であった。遊離酸含量は、酢酸として
０．５％であった。Comparative Example 3 (Example in which acetic anhydride was used as an acylating agent) 4.5 g of acetic anhydride was added to 100 g of the reaction product of Example 1 before addition of carbonate (molar ratio of diethanolamine to 0.8 times).
Was added and stirred for 1 hour, then, under reduced pressure of 20 mmHg, 8
Deodorization was performed by heating at 0 ° C. for 1 hour. Colored brown during this operation. The diethanolamine content of this product was quantified and found to be 1.4%. The free acid content was 0.5% as acetic acid.
【００２０】このようにして得た各ヤシ油脂肪酸ジエタ
ノールアミドについて、その特性を下記の方法によって
測定した。The characteristics of each coconut oil fatty acid diethanolamide thus obtained were measured by the following methods.
【００２１】１．経時着色 経時着色は、５０℃に１ケ月保存し、次のように測定し
た。 ○・・・着色なし △・・・僅かに着色 ×・・・着色 ２．増粘性 下記の処方の液体洗浄剤組成物を調製し、２５℃におけ
る粘度をＢ型回転粘度計を用いて測定した。 （処方） ソジウムラウリルエーテルサルフェート １２％ 脂肪酸ジエタノールアミド（実施例１〜４、比較例１〜３） ８％ クエン酸 ｐＨ＝７とする量 水 残1. Coloring with time Coloring with time was stored at 50 ° C for 1 month and measured as follows. ○: No coloring △: Slightly colored ×: Colored 2. Thickening A liquid detergent composition having the following formulation was prepared, and its viscosity at 25 ° C was measured using a B-type rotational viscometer. (Formulation) Sodium lauryl ether sulfate 12% Fatty acid diethanolamide (Examples 1 to 4, Comparative Examples 1 to 3) 8% Citric acid pH = 7 Amount of water remaining
【００２３】[0023]
【表１】 [Table 1]
【発明の効果】本発明によって得られた脂肪酸ジエタノ
ールアミドはジエタノールアミン含量が極めて低いの
で、経時着色が起こりにくい。INDUSTRIAL APPLICABILITY The fatty acid diethanolamide obtained according to the present invention has an extremely low diethanolamine content, so that coloration over time does not easily occur.
Claims (3)
する一般式（Ｉ） 【化１】 （Ｉ）（式中Ｒ1 ＣＯは、炭素数６〜２２の飽和または
不飽和脂肪酸残基を表す。）で表される脂肪酸ジエタノ
ールアミドに、カーボネートを加えて、ジエタノールア
ミンをアシル化することを特徴とする、ジエタノールア
ミン含量の低い脂肪酸ジエタノールアミドの製造方法。1. A compound represented by the general formula (I) containing diethanolamine as an impurity: (I) (wherein R 1 CO represents a saturated or unsaturated fatty acid residue having 6 to 22 carbon atoms), a carbonate is added to the fatty acid diethanolamide to acylate the diethanolamine. A method for producing a fatty acid diethanolamide having a low content of diethanolamine.
キル基を表す。）で表されるアルキルカーボネートであ
る請求項１記載のジエタノールアミン含量の低い脂肪酸
ジエタノールアミドの製造方法。2. The carbonate used has the general formula (II): The method for producing a fatty acid diethanolamide having a low diethanolamine content according to claim 1, which is an alkyl carbonate represented by (II) (wherein R 2 and R 3 represent an alkyl group having 1 to 6 carbon atoms).
たは不飽和のアシル基を表し、Ｒ5は、炭素数１〜６の
アルキル基を表す。）で表されるアシルカーボネートで
ある請求項１記載のジエタノールアミン含量の低い脂肪
酸ジエタノールアミドの製造方法。3. The carbonate used has the general formula (III): An acyl carbonate represented by (III) (wherein R 4 CO represents a saturated or unsaturated acyl group having 6 to 22 carbon atoms, and R 5 represents an alkyl group having 1 to 6 carbon atoms). The method for producing a fatty acid diethanolamide having a low diethanolamine content according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3226456A JP2975733B2 (en) | 1991-08-12 | 1991-08-12 | Method for producing fatty acid jetanolamide with low content of jetanolamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3226456A JP2975733B2 (en) | 1991-08-12 | 1991-08-12 | Method for producing fatty acid jetanolamide with low content of jetanolamine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH06116219A true JPH06116219A (en) | 1994-04-26 |
| JP2975733B2 JP2975733B2 (en) | 1999-11-10 |
Family
ID=16845386
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3226456A Expired - Lifetime JP2975733B2 (en) | 1991-08-12 | 1991-08-12 | Method for producing fatty acid jetanolamide with low content of jetanolamine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2975733B2 (en) |
-
1991
- 1991-08-12 JP JP3226456A patent/JP2975733B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2975733B2 (en) | 1999-11-10 |
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