JP2019037175A - メチルケトン類の製造方法 - Google Patents
メチルケトン類の製造方法 Download PDFInfo
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- JP2019037175A JP2019037175A JP2017162005A JP2017162005A JP2019037175A JP 2019037175 A JP2019037175 A JP 2019037175A JP 2017162005 A JP2017162005 A JP 2017162005A JP 2017162005 A JP2017162005 A JP 2017162005A JP 2019037175 A JP2019037175 A JP 2019037175A
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 35
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- 235000014113 dietary fatty acids Nutrition 0.000 claims description 20
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- 150000004665 fatty acids Chemical class 0.000 claims description 20
- 235000013351 cheese Nutrition 0.000 claims description 15
- 239000007858 starting material Substances 0.000 claims description 11
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- 238000012258 culturing Methods 0.000 claims description 6
- 241000228143 Penicillium Species 0.000 claims description 5
- 235000013826 starch sodium octenyl succinate Nutrition 0.000 claims description 5
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- 108010010803 Gelatin Proteins 0.000 claims description 3
- 229920002907 Guar gum Polymers 0.000 claims description 3
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- 238000000034 method Methods 0.000 abstract description 25
- 238000000855 fermentation Methods 0.000 abstract description 17
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- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 10
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- 238000004821 distillation Methods 0.000 description 8
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- 239000007857 degradation product Substances 0.000 description 7
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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- 239000004367 Lipase Substances 0.000 description 2
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- 125000004432 carbon atom Chemical group C* 0.000 description 2
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- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
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- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
- 235000008939 whole milk Nutrition 0.000 description 2
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- GUOCOOQWZHQBJI-UHFFFAOYSA-N 4-oct-7-enoxy-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)OCCCCCCC=C GUOCOOQWZHQBJI-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000374462 Aspergillus pseudoglaucus Species 0.000 description 1
- 241000914343 Aspergillus ruber Species 0.000 description 1
- 244000057399 Dalea candida Species 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 244000271379 Penicillium camembertii Species 0.000 description 1
- 235000002245 Penicillium camembertii Nutrition 0.000 description 1
- 241000228129 Penicillium janthinellum Species 0.000 description 1
- 241001437281 Piophila casei Species 0.000 description 1
- 241000235527 Rhizopus Species 0.000 description 1
- 240000005384 Rhizopus oryzae Species 0.000 description 1
- 235000013752 Rhizopus oryzae Nutrition 0.000 description 1
- 241001148470 aerobic bacillus Species 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- 229940031892 aspergillus ruber Drugs 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 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
- 238000005119 centrifugation Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
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- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
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- 239000005428 food component Substances 0.000 description 1
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- 229940014259 gelatin Drugs 0.000 description 1
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- 230000003301 hydrolyzing effect Effects 0.000 description 1
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- -1 mold Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
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- 238000007254 oxidation reaction Methods 0.000 description 1
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- XDLYMKFUPYZCMA-UHFFFAOYSA-M sodium;4-oct-1-enoxy-4-oxobutanoate Chemical compound [Na+].CCCCCCC=COC(=O)CCC([O-])=O XDLYMKFUPYZCMA-UHFFFAOYSA-M 0.000 description 1
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Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
純水551.4gに粘度が1〜3mPa・sとなる量の増粘剤(表1に示した事前に調整試験をした結果を参照し、それぞれ、ペクチン0.6g、オクテニルコハク酸デンプンナトリウム6.0g、ヒドロキシプロピルデンプン3.6g、リン酸架橋デンプン6.0g、ゼラチン6.0g、グアーガム1.2g、アラビアガム0.6gを添加)、乳糖30.0g、ホエイソルト9.0g、ホエイたんぱく質濃縮物5.1g、シリコーン樹脂1.2g、90%乳酸3.0gを2L容のジャーファーメンターに投入し80℃、30分間加熱殺菌後27℃まで冷却したものを液体培地とした。この液体培地にチーズ用カビスターターを分生子数が5×105個/mlとなるように添加した。培養温度27℃、撹拌速度180rpm、5.0L/minにて通気を行いながら96時間培養したものを培養液とした。その後純水372.8g、乳糖19.5g、ホエイソルト5.6g、ホエイたんぱく質濃縮物3.4g、乳脂肪酵素分解物3.0g(酸価220)を別容器に投入し、TKホモミキサー正転6000回転で乳化しながらウォーターバスで80℃、30分間加熱殺菌後27℃まで冷却したものを基質液とし、前述の培養液に投入した。この培養液をさらに撹拌速度180rpm、2.0L/minにて通気を行いながら18時間培養したものを発酵液とした。この発酵液に95vol.%エタノール100.5gを投入し、常圧蒸留にて99gまでの留分を得た。
(分析条件)
Instrument : HP 6890N
Column : TC-WAX、 30m×0.25mm×0.25μm
Flow : 1.5mL/min、 34cm/sec
17.0psi(定圧モード)
Column Temp : 65℃−120℃(3℃/min)
120℃−250℃(5℃/min)
Detector : FID、280℃
Injection : 250℃
キャリアガス : He
純水551.4g、乳糖30g、ホエイソルト9.0g、ホエイタンパク質濃縮物5.1g、シリコーン樹脂1.2g、90%乳酸3.0gを含む培地にペクチンを0.01%、0.05%、0.1%、0.2%、0.3%それぞれ加えて2L容ジャーファーメンターに投入し80℃、30分間加熱殺菌後27℃まで冷却したものを液体培地とした。その後の工程は実施例1に示した方法に準じた。表3にペクチン添加量と粘度、メチルケトン生成量を示す。
純水551.4g、乳糖30g、ホエイソルト9.0g、ホエイタンパク質濃縮物5.1g、シリコーン樹脂1.2g、90%乳酸3.0gを含む培地にオクテニルコハク酸デンプンナトリウムを1%、5%、10%それぞれ加えて2L容ジャーファーメンターに投入し80℃、30分間加熱殺菌後27℃まで冷却したものを液体培地とした。その後の工程は実施例1に示した方法に準じた。表4にオクテニルコハク酸デンプンナトリウムの添加濃度、粘度、メチルケトン生成量を示す。なお、オクテニルコハク酸デンプンナトリウムを5%添加した場合でもメチルケトン発酵は進行したが生成量は減少したことから5%添加では効率が低下すると判断した。また、10%添加時の粘度140mPa・sでもメチルケトン発酵は進行したが、消泡できないほど発泡が著しいため、製造条件として現実的ではないと判断した。
Claims (6)
- 増粘剤を添加した液体培地にメチルケトン類を生産可能な真菌類の分生子を接種して培養した後、液体培地および脂肪酸を加えてさらに培養するメチルケトン類の製造方法。
- 増粘剤が、ペクチン、オクテニルコハク酸デンプンナトリウム、リン酸架橋デンプン、ゼラチン、グアーガムからなる群より選択される少なくとも1種である、請求項1に記載のメチルケトン類の製造方法。
- 増粘剤を添加して培養液の粘度を1〜3mPa・sに調整する請求項1に記載のメチルケトン類の製造方法。
- 真菌類がペニシリウム属菌である請求項1のメチルケトン類の製造方法。
- 真菌類としてチーズスターターを使用する請求項1に記載のメチルケトン類の製造方法。
- チーズスターターが懸濁液状のものである請求項5に記載のメチルケトン類の製造方法。
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JPS56106588A (en) * | 1980-01-23 | 1981-08-24 | Konbiron Inc | Production of pectin containing culture medium |
JPH02265495A (ja) * | 1988-09-09 | 1990-10-30 | Showa Sangyo Co Ltd | 発酵法によるメチルケトン及び/またはその対応アルコールの製造法、及び培養液の使用 |
JPH0376588A (ja) * | 1989-07-27 | 1991-04-02 | Quest Internatl Bv | アルキルメチルケトンを生産する方法、前記アルキルメチルケトンを含有する風味成分、前記風味成分を含有する風味組成物及び前記アルキルメチルケトンを含有する食品 |
JPH04189790A (ja) * | 1990-11-13 | 1992-07-08 | Snow Brand Milk Prod Co Ltd | チーズの包装体とチーズの熟成方法 |
JPH05268875A (ja) * | 1992-03-30 | 1993-10-19 | Morinaga Milk Ind Co Ltd | カマンベール・チーズの製造法 |
JP2002253221A (ja) * | 2001-03-05 | 2002-09-10 | Univ Nagoya | 植物培養細胞からの長期間安定な物質生産方法 |
JP2004344087A (ja) * | 2003-05-23 | 2004-12-09 | Matsushita Electric Ind Co Ltd | 微生物計量における計量方法および液体培地および微多孔膜支持体 |
JP2008054580A (ja) * | 2006-08-31 | 2008-03-13 | Gekkeikan Sake Co Ltd | デフェリフェリクリシン高生産変異株、シデロフォア生産用の液体培地、シデロフォアの製造方法 |
JP4764309B2 (ja) * | 2006-10-24 | 2011-08-31 | 長谷川香料株式会社 | メチルケトン類の製造方法 |
-
2017
- 2017-08-25 JP JP2017162005A patent/JP7013635B2/ja active Active
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS56106588A (en) * | 1980-01-23 | 1981-08-24 | Konbiron Inc | Production of pectin containing culture medium |
JPH02265495A (ja) * | 1988-09-09 | 1990-10-30 | Showa Sangyo Co Ltd | 発酵法によるメチルケトン及び/またはその対応アルコールの製造法、及び培養液の使用 |
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