JPS6023720B2 - Oil and fat refining method - Google Patents
Oil and fat refining methodInfo
- Publication number
- JPS6023720B2 JPS6023720B2 JP6784377A JP6784377A JPS6023720B2 JP S6023720 B2 JPS6023720 B2 JP S6023720B2 JP 6784377 A JP6784377 A JP 6784377A JP 6784377 A JP6784377 A JP 6784377A JP S6023720 B2 JPS6023720 B2 JP S6023720B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- salt
- compound
- oil
- oils
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 24
- 238000007670 refining Methods 0.000 title claims description 8
- 239000003921 oil Substances 0.000 claims description 17
- 239000003925 fat Substances 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 13
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 10
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 8
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 6
- 239000004471 Glycine Substances 0.000 claims description 5
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 3
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 3
- 235000003704 aspartic acid Nutrition 0.000 claims description 3
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 3
- 229930182817 methionine Natural products 0.000 claims description 3
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 2
- GRGSHONWRKRWGP-UHFFFAOYSA-N 2-amino-4-sulfobenzoic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1C(O)=O GRGSHONWRKRWGP-UHFFFAOYSA-N 0.000 claims description 2
- WGLQHUKCXBXUDV-UHFFFAOYSA-N 3-aminophthalic acid Chemical compound NC1=CC=CC(C(O)=O)=C1C(O)=O WGLQHUKCXBXUDV-UHFFFAOYSA-N 0.000 claims description 2
- ADVCEUPBLBYYEF-UHFFFAOYSA-N 4-amino-3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=C(O)C(S(O)(=O)=O)=CC2=C1 ADVCEUPBLBYYEF-UHFFFAOYSA-N 0.000 claims description 2
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 claims description 2
- 239000004475 Arginine Substances 0.000 claims description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims description 2
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 2
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004473 Threonine Substances 0.000 claims description 2
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 2
- 235000004279 alanine Nutrition 0.000 claims description 2
- 229960004909 aminosalicylic acid Drugs 0.000 claims description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 2
- 229960003067 cystine Drugs 0.000 claims description 2
- 235000013922 glutamic acid Nutrition 0.000 claims description 2
- 239000004220 glutamic acid Substances 0.000 claims description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
- 159000000001 potassium salts Chemical class 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 239000004474 valine Substances 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims 3
- LEVWYRKDKASIDU-QWWZWVQMSA-N D-cystine Chemical compound OC(=O)[C@H](N)CSSC[C@@H](N)C(O)=O LEVWYRKDKASIDU-QWWZWVQMSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 235000019198 oils Nutrition 0.000 description 16
- 235000019197 fats Nutrition 0.000 description 14
- 235000019482 Palm oil Nutrition 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 239000002540 palm oil Substances 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 235000014593 oils and fats Nutrition 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000004927 clay Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 150000002978 peroxides Chemical class 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 238000004042 decolorization Methods 0.000 description 4
- 239000000344 soap Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- -1 amino compound Chemical class 0.000 description 3
- 235000015278 beef Nutrition 0.000 description 3
- 238000004332 deodorization Methods 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LTASFWDWBYFZQQ-UHFFFAOYSA-N 2-amino-5-nitrobenzenesulfonic acid Chemical compound NC1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O LTASFWDWBYFZQQ-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
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 235000019774 Rice Bran oil Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- PXEDJBXQKAGXNJ-QTNFYWBSSA-L disodium L-glutamate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CCC([O-])=O PXEDJBXQKAGXNJ-QTNFYWBSSA-L 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000021323 fish oil Nutrition 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 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 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000013923 monosodium glutamate Nutrition 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000008165 rice bran oil Substances 0.000 description 1
- 229940073490 sodium glutamate Drugs 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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Landscapes
- Fats And Perfumes (AREA)
Description
【発明の詳細な説明】
本発明は油脂の精製法に関し、詳しくは色相および安定
性にすぐれた精製油脂を得るための精製法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for refining fats and oils, and more particularly to a method for obtaining refined fats and oils with excellent color and stability.
通常行われている油脂の精製は、鍵酸または有機酸によ
る脱カム工程を行ったの、アルカリ水溶液による遊離脂
肪酸の中和とそれによって生成したセッケンの温水によ
る洗浄除去とからなる脱酸工程が行われ、つぎに活性白
士や活性炭などの吸着剤による脱色工程、さらに高真空
下で水蒸気を用いた脱臭工程などいくつもの工程を経て
いる。The usual refining of fats and oils involves a decamming process using key acid or an organic acid, or a deacidification process consisting of neutralizing free fatty acids with an alkaline aqueous solution and washing and removing the resulting soap with warm water. The process then goes through a number of steps, including a decolorization process using adsorbents such as activated white paper and activated carbon, and then a deodorization process using steam under high vacuum.
しかしながらこのような通常の精製法で精製された油脂
は、色相、貯蔵安定性、熱安定性などの品質が一定しな
いため、脱色工程において吸着剤の添加量を増したり、
その種類を変えたりする必要が生じる場合が多く、また
、このようにしても品質の良い精製油脂が得られない場
合もある。この原因は主としてその原料油脂の品質にも
とづくものである。つまり原料油脂の採取方法、貯蔵方
法やその期間、輸送方法などの違いにより原料油脂の色
相、酸価、過酸化物価、カルボニル価、不純物の含有量
などの差を生ずる。。このために精製された油脂の品質
にも差が生じていた。本発明は、このような欠点を解決
したものであり、原料油脂の品質が異なっていても、常
に品質のすぐれた精製油脂を得ることのできる精製法で
ある。すなわち、本発明は既知の油脂の精製法に加えて
、油脂に下記aまたはbから選ばれた化合物(以下、ア
ミノ化合物という)を接触させる工程を、脱酸工程より
前に行うことを特徴とする油脂の精製法である。However, the quality of oils and fats refined by such ordinary refining methods, such as hue, storage stability, and thermal stability, is not constant, so it is necessary to increase the amount of adsorbent added in the decolorization process,
There are many cases where it is necessary to change the type of oil, and even with this method, it may not be possible to obtain refined oils and fats of good quality. This is mainly due to the quality of the raw material oil. In other words, differences in the extraction method, storage method, period, transportation method, etc. of the raw material oils and fats cause differences in the hue, acid value, peroxide value, carbonyl value, impurity content, etc. of the raw material oils and fats. . This has led to differences in the quality of refined oils and fats. The present invention solves these drawbacks and is a refining method that can always obtain refined oils and fats of excellent quality even if the quality of the raw material oils and fats is different. That is, the present invention is characterized in that, in addition to known methods for refining fats and oils, a step of contacting fats and oils with a compound selected from the following a or b (hereinafter referred to as an amino compound) is carried out before the deacidification step. This is a method for refining fats and oils.
‘a} アミノ基とカルボン酸基とをもつ化合物または
その塩。'a} A compound having an amino group and a carboxylic acid group or a salt thereof.
‘b’アミノ基とスルホン酸基とをもつ化合物またはそ
の塩。'b' A compound having an amino group and a sulfonic acid group or a salt thereof.
本発明の接触処理工程は脱酸工程の前に行うが、とくに
脱ガム工程の前または脱ガム工程と同時に行うのが好ま
しい。Although the contact treatment step of the present invention is carried out before the deoxidation step, it is particularly preferably carried out before or simultaneously with the degumming step.
そしてつぎの脱酸工程を慎重に行うと、脱色工程を省略
することができるほどの淡色の精製油脂が得られる。前
記アミノ化合物を原料油脂に接触させると、過酸化物や
カルボニル化合物などの酸化生成物やガム質やその他の
不純物は、還元された安定な化合物や除去されやすい化
合物に変化するものと考えられる。If the next deoxidizing step is carried out carefully, refined fats and oils with such a light color that the decolorizing step can be omitted can be obtained. When the amino compound is brought into contact with the raw oil or fat, oxidation products such as peroxides and carbonyl compounds, gums, and other impurities are thought to be converted into stable reduced compounds or compounds that are easily removed.
本発明における接触処理条件は、アミノ化合を原料油脂
に対して0.01〜5重量%添加して20〜150午0
で2〜90分間接触させるものである。The contact treatment conditions in the present invention are as follows: 0.01 to 5% by weight of an amino compound is added to the raw material oil and fat;
The contact is carried out for 2 to 90 minutes.
本発明の方法が適用される油脂としては、脂、豚脂、魚
油、鯨油などの動物油脂、パーム油、大豆油、綿実油、
アマニ油、オリブ油、ャシ油、ヒマシ油、ナタネ油、コ
メヌカ油などの植物油脂、および脂肪酸とグリセリンと
のェステル化反応で得られる合成トリグリセリドがある
。The fats and oils to which the method of the present invention is applied include animal fats and oils such as fat, lard, fish oil, and whale oil, palm oil, soybean oil, cottonseed oil,
These include vegetable oils and fats such as linseed oil, olive oil, coconut oil, castor oil, rapeseed oil, and rice bran oil, and synthetic triglycerides obtained by the esterification reaction of fatty acids and glycerin.
本発明に用いるアミノカ合物のうち、【aーアミノ基と
カルボン酸基とをもつ酸基とをもつ化合物またはその塩
としては、アスパラギン酸、リジン、バリン、メチオニ
ン、シスチン、アラニン、フエニルアラニン、アルギニ
ン、グルタミン酸、ロイシン、グリシン、セリン、トレ
オニン、ヒスチジン、トリプトフアン、アントラニル酸
、アミノサリチル酸、アミノフタル酸などのほか、これ
らの塩酸塩、ナトリウム塩もしくはカリウム塩などがあ
る。‘bーァミ/基とスルホン酸基とをもつ化合物また
はその塩としては、スルフアミン酸、4−スルホアント
ラニル酸、4ーニトロアニリンー2−スルホン酸、1ー
アミノ−2ーナフトール−3,6−ジスルホン酸などの
ほか、これらのナトリウム塩もしくはカリウム塩がある
。つぎに本発明ご実施例および比較例により説明する。Among the aminocarbon compounds used in the present invention, examples of compounds having an acid group having an a-amino group and a carboxylic acid group or salts thereof include aspartic acid, lysine, valine, methionine, cystine, alanine, phenylalanine, In addition to arginine, glutamic acid, leucine, glycine, serine, threonine, histidine, tryptophan, anthranilic acid, aminosalicylic acid, and aminophthalic acid, these include hydrochloride, sodium salt, or potassium salt. Examples of compounds having a 'b-family/ group and a sulfonic acid group or their salts include sulfamic acid, 4-sulfoanthranilic acid, 4-nitroaniline-2-sulfonic acid, and 1-amino-2naphthol-3,6-disulfonic acid. In addition to these, there are also sodium and potassium salts. Next, the present invention will be explained using examples and comparative examples.
なお、%は重量%を示す。また、各実施例および比較例
の精製油脂および精製ェステルの分析値とAOM試験(
AOCS試験法Cd−12−57)における過酸化物価
を表1に示すが、本発明の方法による精製油脂は、従来
の方法による精製油脂に比較して色相が良好で過酸化物
価が低く、AOM試験においてもすぐれた安定性を示す
ことが明らかである。Note that % indicates weight %. In addition, the analytical values and AOM test (
The peroxide value in AOCS test method Cd-12-57) is shown in Table 1, and the refined fats and oils obtained by the method of the present invention have better hue and lower peroxide value than the refined fats and oils obtained by the conventional method. It is clear that it exhibits excellent stability in tests.
実施例 1
80午0に加熱したパーム油(酸価0.7、過酸化物価
6.0、ヨウ素価53.u色相は濃赤燈色で測定不能)
に75%リン酸1%と水1%とを添加して30分間縄拝
したのち、フェニルアラニンを0.5%添加して30分
間縄拝した。Example 1 Palm oil heated at 80:00 (acid value 0.7, peroxide value 6.0, iodine value 53.U hue is dark red light color and cannot be measured)
After 1% of 75% phosphoric acid and 1% of water were added to the mixture and roped for 30 minutes, 0.5% of phenylalanine was added and roped for 30 minutes.
不溶分を遠心分離により除去したのち、4度ポーメのカ
セィンソーダ水溶液を3.0%(パーム油の酸価に対し
て1.3音当量)加えて5分間鍵拝した。ここで生じた
セツケン分を遠心分離したのち、水洗した。つぎに減圧
下に脱水後、活性白土を1%添加して1400qoで3
0分間擬拝した。10000で炉過を行って活性白土を
除去したのち、5肋Hg,260℃で90分間水蒸気脱
臭を行つた。After removing insoluble matter by centrifugation, 3.0% (1.3 sonic equivalents based on the acid value of palm oil) of a 4-degree casein soda aqueous solution was added and stirred for 5 minutes. The resulting liquid was centrifuged and then washed with water. Next, after dehydration under reduced pressure, 1% activated clay was added and the mixture was heated at 1400qo.
I worshiped for 0 minutes. After the activated clay was removed by filtration at 10,000 ℃, steam deodorization was performed at 5 Hg and 260° C. for 90 minutes.
実施例 2
実施例1において、フェニルァラニンの代りにグルタミ
ン酸ソーダを用いた以外はまった〈同じ条件でパーム油
を精製した。Example 2 Palm oil was refined under the same conditions as in Example 1 except that sodium glutamate was used instead of phenylalanine.
実施例 3
実施例1において、フェニルアラニンの代りにアスパラ
ギン酸を用いた以外はまったく同じ条件でパーム油を精
製した。Example 3 Palm oil was purified under exactly the same conditions as in Example 1 except that aspartic acid was used instead of phenylalanine.
実施例 4
実施例1において、フェニルアラニンの代りにスルフア
ミン酸を用いて以外はまったく同じ条件でパーム油を精
製した。Example 4 Palm oil was purified under exactly the same conditions as in Example 1 except that sulfamic acid was used instead of phenylalanine.
実施例 5
実施例1において、リン酸による脱ガム工程を行わない
以外はまったく同じ条件でパーム油を精製した。Example 5 Palm oil was purified under exactly the same conditions as in Example 1 except that the degumming step using phosphoric acid was not performed.
比較例 1
実施例1において、フェニルアラニンによる接触処理工
程をしない以外はまったく同じ条件でパーム油を精製し
た。Comparative Example 1 Palm oil was refined under exactly the same conditions as in Example 1 except that the contact treatment step with phenylalanine was not performed.
比較例 2
実施例1において、リン酸による脱ガム工程とフェニル
アラニンによる接触処理工程を行わない以外は、まった
く同じ条件でパーム油を精製した。Comparative Example 2 Palm oil was purified under exactly the same conditions as in Example 1, except that the degumming step with phosphoric acid and the contact treatment step with phenylalanine were not performed.
実施例 6
80℃に加熱した牛脂(酸価57、過酸化物価15.0
ヨウ素価46.ふ色相:ロビボンドR5.0Y4o〔5
章インチセル〕)に75%リン酸を0‐5%加えて3の
分間燭拝したのち、グリシンを1%添加して30分間鷹
拝した。Example 6 Beef tallow heated to 80°C (acid value 57, peroxide value 15.0
Iodine value 46. Hue: Lovibond R5.0Y4o [5
After adding 0-5% of 75% phosphoric acid to the cellulose cell and incubating for 3 minutes, 1% of glycine was added and incubating for 30 minutes.
つぎに実施例1とまったく同様に脱酸、脱色および脱臭
の各工程を行った。実施例 7実施例9においてグリシ
ンの代りにメチオニンを用いた以外は、まったく同じ条
件で牛脂を精製した。Next, the steps of deoxidation, decolorization, and deodorization were carried out in exactly the same manner as in Example 1. Example 7 Beef tallow was purified under exactly the same conditions as in Example 9 except that methionine was used instead of glycine.
比較例 3
実施例6においてグリシンによる接触処理工程を行わな
い以外は、まったしく同じ条件で牛脂を精製した。Comparative Example 3 Beef tallow was purified under exactly the same conditions as in Example 6 except that the contact treatment step with glycine was not performed.
実施例 8
グリセリン184夕(2モル)、オレィン酸1708夕
(6.1モル)および触媒として酸化亜鉛19夕を用い
て滋0〜240℃で1瓜時間ェステル化反応を行った。Example 8 An esterification reaction was carried out at 0 to 240° C. for 1 hour using 184 mol of glycerin (2 mol), 170 mol of oleic acid (6.1 mol) and 19 mol of zinc oxide as a catalyst.
得られたェステル化物の酸価は9.7であった。80℃
に冷却したのち、スルフアミン酸を1%添加して30分
間蝿拝し、ついで不港分を遠心分離した。The acid value of the obtained esterified product was 9.7. 80℃
After cooling, 1% sulfamic acid was added and the mixture was stirred for 30 minutes, followed by centrifugation of the unused portion.
つぎに、20度ボーメのカセィソーダ水溶液を7.2%
(ェステル化生成物の酸価に対して1.針音当量)加え
て5分間縄拝し、生成したセッケン分を遠D分離してか
ら水洗した。脱水後、活性白土を2%添加して120ぴ
0で30分間燈押した。100℃で活性白土を炉別した
のち、5脚日g、250つ○で60分間水蒸気脱臭を行
って精製オレィン酸トリグリセリドを得た。Next, add 7.2% caustic soda solution at 20 degrees Baume.
(1. needle sound equivalent relative to the acid value of the esterified product) was added to the soap for 5 minutes, and the resulting soap was separated by far-D and washed with water. After dehydration, 2% activated clay was added and the mixture was heated at 120 mm for 30 minutes. After the activated clay was furnace-separated at 100°C, it was deodorized with steam for 60 minutes at 5 g/day and 250 x ○ to obtain purified oleic acid triglyceride.
比較例 4
実施例8において、スルフアミン酸による接触処料工程
を行わない以外はまったく同じ条件でオレイン酸トリグ
リセリドの精製を行った。Comparative Example 4 Oleic acid triglyceride was purified under exactly the same conditions as in Example 8, except that the contact treatment step with sulfamic acid was not performed.
表 1 精製油の分析値とAON試験結果実施例 9
グリセリン92夕(1モル)、パルミチン酸7班夕(3
.1モル)および触媒として酸化亜鉛9夕を用いて、2
00〜24ぴ○で10時間ェステル化反応を行った。Table 1 Analytical values of refined oil and AON test results Example 9 Glycerin 92 moles (1 mol), palmitic acid 7 moles (3 moles)
.. 1 mol) and zinc oxide as a catalyst.
The esterification reaction was carried out at 00 to 24 pi for 10 hours.
得られたェステル化物の酸化は13.5であつた。90
30に冷却したのち、スルフアミン酸を1%添加して3
0分間縄拝し、ついで不溶分を遠心分離した。The oxidation value of the obtained esterified product was 13.5. 90
After cooling to 30℃, 1% sulfamic acid was added to
The mixture was stirred for 0 minutes, and then the insoluble matter was centrifuged.
つぎに、20度ポーメのカセイソーダ水溶液を10%(
ェステル化生成物の酸化に対して1.5倍当量)加えて
10分間鷹拝し、生成したセッケン分を遠心分離してか
ら水洗し、ついで減圧下に脱水し‐た。Next, add 10% (
1.5 times equivalent to the oxidation of the esterified product) was added and incubated for 10 minutes, and the resulting soap was centrifuged, washed with water, and then dehydrated under reduced pressure.
得られたパルミチン酸トリグリセリドの色相はロビボン
ド(5言インチセル)でR。‐3Y28であった。つぎ
に活性白土を2%添加して120℃で30分間鷹拝した
のち、100℃に冷却して活性白土を炉別した。The hue of the obtained palmitic acid triglyceride was R on Lovibond (5-word inch cell). -3Y28. Next, 2% of activated clay was added and heated at 120°C for 30 minutes, then cooled to 100°C and the activated clay was separated.
脱色工程を行ったパルミチン酸トリグリセリドの色相は
RO.3Y2.2であった。比較例 5
実施例9において、スルフアミン酸による接触処理工程
を行わない以外はまったく同じ条件でパルミチル酸トリ
グリセリドを糟造した。The hue of palmitic acid triglyceride that underwent the decolorization process was RO. It was 3Y2.2. Comparative Example 5 Palmitylic acid triglyceride was made under exactly the same conditions as in Example 9 except that the contact treatment step with sulfamic acid was not performed.
反応後に脱酸工程を行ったパルミチン酸トリグリセリド
の色相はRI.1,YIO.0であり、脱色工程後にお
ける色相はRO.&Y9.0であった。The hue of palmitic acid triglyceride that was subjected to a deoxidizing step after the reaction was RI. 1, YIO. 0, and the hue after the bleaching process is RO. &Y was 9.0.
Claims (1)
せる工程を行つたのち、脱酸工程を行うことを特徴とす
る油脂の精製法。 (a)アミノ基とカルボン酸とをもつ化合物またはその
塩。 (b)アミノ基とスルホン酸基とをもつ化合物またはそ
の塩。 2 アミノ基とカルボン酸基とをもつ化合物またはその
塩が、アスパラギン酸、リジン、バリン、メチオニン、
シスチン、アラニン、フエニルアラニン、アルギニン、
グルタミン酸、ロイシン、グリシン、セリン、トレオニ
ン、ヒスチジン、トリプトフアン、アントラニル酸、ア
ミノサリチル酸、アミノフタル酸、またはこれらの塩酸
塩、ナトリウム塩もしくはカリウム塩であら特許請求の
範囲第1項記載の精製法。 3 アミノ基とスルホン酸基とをもつ化合物またはその
塩が、スルフアミン酸、4−スルホアントラニル酸、4
−ニトロアニリン−2−スルホン酸、1−アミノ−2ナ
フトール−3,6−ジスルホン酸、またはこれらのナト
リウム塩もしくはカリウム塩である特許請求の範囲第1
項記載の精製法。[Scope of Claims] 1. A method for refining fats and oils, which comprises carrying out a step of bringing a compound selected from a or b below into contact with hydraulic pressure, followed by a deoxidizing step. (a) A compound having an amino group and a carboxylic acid or a salt thereof. (b) A compound having an amino group and a sulfonic acid group or a salt thereof. 2 A compound having an amino group and a carboxylic acid group or a salt thereof is aspartic acid, lysine, valine, methionine,
cystine, alanine, phenylalanine, arginine,
The purification method according to claim 1, wherein the purification method is glutamic acid, leucine, glycine, serine, threonine, histidine, tryptophan, anthranilic acid, aminosalicylic acid, aminophthalic acid, or their hydrochloride, sodium salt, or potassium salt. 3 A compound having an amino group and a sulfonic acid group or a salt thereof is sulfamic acid, 4-sulfoanthranilic acid, 4-sulfamic acid,
-Nitroaniline-2-sulfonic acid, 1-amino-2naphthol-3,6-disulfonic acid, or their sodium or potassium salts Claim 1
Purification method described in section.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP6784377A JPS6023720B2 (en) | 1977-06-10 | 1977-06-10 | Oil and fat refining method |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP6784377A JPS6023720B2 (en) | 1977-06-10 | 1977-06-10 | Oil and fat refining method |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS543106A JPS543106A (en) | 1979-01-11 |
JPS6023720B2 true JPS6023720B2 (en) | 1985-06-08 |
Family
ID=13356628
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP6784377A Expired JPS6023720B2 (en) | 1977-06-10 | 1977-06-10 | Oil and fat refining method |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6023720B2 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5949017A (en) | 1996-06-18 | 1999-09-07 | Abb Power T&D Company Inc. | Electrical transformers containing electrical insulation fluids comprising high oleic acid oil compositions |
-
1977
- 1977-06-10 JP JP6784377A patent/JPS6023720B2/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
JPS543106A (en) | 1979-01-11 |
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