JP2015502961A - ニトリル官能基を含む化合物を製造する方法 - Google Patents
ニトリル官能基を含む化合物を製造する方法 Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 40
- 238000004519 manufacturing process Methods 0.000 title abstract description 9
- 125000002560 nitrile group Chemical group 0.000 title abstract 3
- 239000003054 catalyst Substances 0.000 claims description 41
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 32
- 229910021529 ammonia Inorganic materials 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 150000002825 nitriles Chemical class 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000001354 calcination Methods 0.000 claims description 4
- XLUBVTJUEUUZMR-UHFFFAOYSA-B silicon(4+);tetraphosphate Chemical compound [Si+4].[Si+4].[Si+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XLUBVTJUEUUZMR-UHFFFAOYSA-B 0.000 claims description 4
- SMMNUDQGZVFDTO-UHFFFAOYSA-N 5-ethoxycarbonylfuran-2-carboxylic acid Chemical compound CCOC(=O)C1=CC=C(C(O)=O)O1 SMMNUDQGZVFDTO-UHFFFAOYSA-N 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- AETGYSUEDWYSME-UHFFFAOYSA-N 5-methoxycarbonylfuran-2-carboxylic acid Chemical compound COC(=O)C1=CC=C(C(O)=O)O1 AETGYSUEDWYSME-UHFFFAOYSA-N 0.000 claims description 2
- NHXSTXWKZVAVOQ-UHFFFAOYSA-N Ethyl furoate Chemical compound CCOC(=O)C1=CC=CO1 NHXSTXWKZVAVOQ-UHFFFAOYSA-N 0.000 claims description 2
- HDJLSECJEQSPKW-UHFFFAOYSA-N Methyl 2-Furancarboxylate Chemical compound COC(=O)C1=CC=CO1 HDJLSECJEQSPKW-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 125000003435 aroyl group Chemical group 0.000 claims description 2
- 125000005333 aroyloxy group Chemical group 0.000 claims description 2
- SHZSZHILNFXXCG-UHFFFAOYSA-N azane;furan-2-carboxylic acid Chemical group [NH4+].[O-]C(=O)C1=CC=CO1 SHZSZHILNFXXCG-UHFFFAOYSA-N 0.000 claims description 2
- MJWAFDPZFACGLR-UHFFFAOYSA-N diazanium furan-2,5-dicarboxylate Chemical compound [NH4+].[NH4+].[O-]C(=O)c1ccc(o1)C([O-])=O MJWAFDPZFACGLR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 150000003568 thioethers Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 3
- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 11
- 241000196324 Embryophyta Species 0.000 description 7
- 239000007789 gas Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
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- 101000836906 Homo sapiens Signal-induced proliferation-associated protein 1 Proteins 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 102100027163 Signal-induced proliferation-associated protein 1 Human genes 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- -1 amine compounds Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
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- 229910001220 stainless steel Inorganic materials 0.000 description 3
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- 239000007858 starting material Substances 0.000 description 3
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 description 2
- 241001133760 Acoelorraphe Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 244000020551 Helianthus annuus Species 0.000 description 2
- 235000003222 Helianthus annuus Nutrition 0.000 description 2
- 240000003183 Manihot esculenta Species 0.000 description 2
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
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- 229920002472 Starch Polymers 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 0.000 description 1
- 241000264877 Hippospongia communis Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- UWQOPFRNDNVUOA-UHFFFAOYSA-N dimethyl furan-2,5-dicarboxylate Chemical compound COC(=O)C1=CC=C(C(=O)OC)O1 UWQOPFRNDNVUOA-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- KCSYJHQYWTYFCM-UHFFFAOYSA-N furan-2,5-dicarbonitrile Chemical compound N#CC1=CC=C(C#N)O1 KCSYJHQYWTYFCM-UHFFFAOYSA-N 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 231100000219 mutagenic Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005504 petroleum refining Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/66—Nitrogen atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
- Catalysts (AREA)
Abstract
Description
一般式(I)の化合物
一般式(III)の化合物
この方法はアンモニアを、一般式(II)の化合物
−好ましくは、1〜6個の炭素原子、より好ましくは、1〜4個の炭素原子を有する鎖状または分岐アルキル基、
−好ましくは、1〜6個の炭素原子および1〜13個のハロゲン原子、より好ましくは、1〜4個の炭素原子および1〜9個のハロゲン原子を有する鎖状または分岐モノ−、ポリ−または過ハロゲン化アルキル基、
−エーテルR4−O−またはチオエーテルR4−S−基(R4は、1〜6個の炭素原子、より好ましくは、1〜4個の炭素原子またはフェニル基を有する鎖状または分岐アルキル基を表す)、
−アシルオキシまたはアロイルオキシR4−CO−O−基(R4は、上記と同じである)、
−アシルまたはアロイルR4−CO基(R4は、上記と同じである)、
−ヒドロキシル基、
−ハロゲン原子、好ましくは、フッ素原子
から選択される。
1mmの温度プローブを備え、電気管状路により加熱される内径2.54cmの管状ステンレス鋼リアクターを用いる。2〜3mmに粉砕され篩分けされたUOP製のSPA1という触媒3mlから構成される触媒床を、3l/hの空気流により、450℃で15時間、活性化する。
1mmの温度プローブを備え、電気管状路により加熱される内径2.54cmの管状ステンレス鋼リアクターを用いる。2〜3mmに粉砕され篩分けされたUOP製のSPA1という触媒3mlから構成される触媒床を、3l/hの空気流により、450℃で15時間、活性化する。活性化後、触媒床を400℃に戻し、空気流を2.7l/hのアンモニア流に交換する。触媒床を、425℃まで再加熱し、20重量%のエタノールエチル2,5−フランジカルボキシレート溶液を、アンモニア流量を2.7l/hに維持しながら、触媒に、5ml/hの流量で注入する。溶液50ml注入後、凝縮物をGCにより分析する。ジエステルの変換率30%で、15%のジニトリル収率が得られる。
1mmの温度プローブを備え、電気管状路により加熱される内径2.54cmの管状ステンレス鋼リアクターを用いる。2〜3mmに粉砕され篩分けされたUOP製のSPA1という触媒3mlから構成される触媒床を、3l/hの空気流により、450℃で15時間、活性化する。活性化後、触媒床を400℃に戻し、空気流を2.4l/hのアンモニア流に交換する。触媒床を、425℃まで再加熱し、THF中エチル2,5−フランジカルボキシレート溶液を、45%のw/w濃度で、アンモニア流量を2.4l/hに維持しながら、触媒に、1.5ml/hの流量で注入する。50ml注入後、凝縮物をGCにより分析する。ジエステルの変換率45%で、14%のジニトリル収率および28%のエステルニトリル収率が得られる。
触媒は、その活性が減少したら、空気の存在下での熱処理により再生することができる。空気流を、冷間触媒床に10l/hの流量で通過させ、500℃までの加熱を4時間にわたって徐々に行う。これらの条件は、その後、15時間維持する。リアクターから出るガスからはCO2を排除しなければならない。続いて、10l/hの窒素下で温度を400℃まで戻し、この温度で、窒素の流量を、アンモニアの流量と徐々に置き換える。発熱しないようにする。その後、触媒を再生する。
Claims (12)
- 一般式(I)の化合物
一般式(III)の化合物
(式中、Rは、1つ以上の任意の置換基を表し、x、yは、0または1に等しく、(x+y)は1または2に等しい)
気相中で、アンモニアを一般式(II)の化合物
と、式Si3(PO4)4のオルトリン酸ケイ素を含む触媒の存在下で、反応させることを含む、方法。 - 式(II)および/または式(IV)の前記化合物は、植物由来の再生可能な材料から得られることを特徴とする請求項1に記載の方法。
- Rが、
−好ましくは、1〜6個の炭素原子、より好ましくは、1〜4個の炭素原子を有する鎖状または分岐アルキル基、
−好ましくは、1〜6個の炭素原子および1〜13個のハロゲン原子、より好ましくは、1〜4個の炭素原子および1〜9個のハロゲン原子を有する鎖状または分岐モノ−、ポリ−または過ハロゲン化アルキル基、
−エーテルR4−O−またはチオエーテルR4−S−基(R4は、1〜6個の炭素原子、より好ましくは、1〜4個の炭素原子またはフェニル基を有する鎖状または分岐アルキル基を表す)、
−アシルオキシまたはアロイルオキシR4−CO−O−基(R4基は、上記と同じである)、
−アシルまたはアロイルR4−CO基(R4基は、上記と同じである)、
−ヒドロキシル基、
−ハロゲン原子、好ましくは、フッ素原子
から選択されることを特徴とする請求項1または2に記載の方法。 - R1およびR2は、−OR3を表すことを特徴とする請求項1〜3のいずれか一項に記載の方法。
- x+yは2に等しく、R1およびR2は同一であることを特徴とする請求項1〜4のいずれか一項に記載の方法。
- 式(II)または式(IV)の前記化合物は、メチル2,5−フランジカルボキシレート、エチル2,5−フランジカルボキシレート、アンモニウム2,5−フランジカルボキシレート、メチル2−フロエート、エチル2−フロエートまたはアンモニウム2−フロエートから選択されることを特徴とする請求項1〜5のいずれか一項に記載の方法。
- 前記反応が、300〜450℃の温度で実施されることを特徴とする請求項1〜6のいずれか一項に記載の方法。
- 前記反応が、固定触媒床を含むリアクターで実施されることを特徴とする請求項1〜7のいずれか一項に記載の方法。
- 前記触媒は、シリカをリン酸で含浸し、空気中か焼することにより得られることを特徴とする請求項1〜8のいずれか一項に記載の方法。
- か焼は、400℃〜800℃の温度で実施されることを特徴とする請求項9に記載の方法。
- 形成された少なくとも前記ニトリル(I)および/または(III)は、対応のアミンを形成するためにハロゲン化されることを特徴とする請求項1〜10のいずれか一項に記載の方法。
- 形成された少なくとも前記ニトリル(I)は、一般式(V)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1161823 | 2011-12-16 | ||
FR1161823A FR2984322B1 (fr) | 2011-12-16 | 2011-12-16 | Procede de fabrication de composes comprenant des fonctions nitriles |
PCT/EP2012/075377 WO2013087765A1 (fr) | 2011-12-16 | 2012-12-13 | Procede de fabrication de composes comprenant des fonctions nitriles |
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EP (1) | EP2791124B1 (ja) |
JP (1) | JP6113746B2 (ja) |
CN (1) | CN103998438B (ja) |
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EA027929B1 (ru) | 2012-05-25 | 2017-09-29 | Янссен Сайенсиз Айрлэнд Юси | Нуклеозиды на основе урацила и спирооксетана |
EP3421482A1 (en) | 2012-12-21 | 2019-01-02 | Alios Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
CN106146442A (zh) * | 2015-04-07 | 2016-11-23 | 中国科学院大连化学物理研究所 | 一种5-羟甲基糠醛催化转化制备2,5-二氰基呋喃的方法 |
TWI794742B (zh) | 2020-02-18 | 2023-03-01 | 美商基利科學股份有限公司 | 抗病毒化合物 |
WO2022221514A1 (en) | 2021-04-16 | 2022-10-20 | Gilead Sciences, Inc. | Methods of preparing carbanucleosides using amides |
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DE912334C (de) * | 1952-06-08 | 1954-05-28 | Phrix Werke Ag | Verfahren zum Herstellen von Dehydroschleimsaeuredinitril |
DE2020866A1 (de) * | 1970-04-29 | 1971-11-18 | Basf Ag | Verfahren zur Herstellung von Hydroxy- und Aminobenzonitrilen |
JPH093030A (ja) * | 1995-06-21 | 1997-01-07 | Huels Ag | 2−ヒドロキシベンゾニトリルの製造法 |
JP2006523671A (ja) * | 2003-04-15 | 2006-10-19 | ファイザー・インク | PPAR調節剤としてのα置換カルボン酸 |
US20110288324A1 (en) * | 2008-12-04 | 2011-11-24 | Roland Jacquot | Method for manufacturing compounds including nitrile functions |
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JPS5419963A (en) * | 1977-07-13 | 1979-02-15 | Noguchi Kenkyusho | Production of 2*55 furandicarbonitrile |
DE3510876A1 (de) * | 1985-03-26 | 1986-10-02 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von aliphatischen dinitrilen |
FR2810317B1 (fr) | 2000-06-14 | 2002-07-26 | Rhodia Chimie Sa | Procede de separation d'un compose de type hydroxybenzonitrile |
US20050187266A1 (en) * | 2003-04-15 | 2005-08-25 | Pfizer Inc | Alpha substituted carboxylic acids |
JP4409238B2 (ja) * | 2003-09-17 | 2010-02-03 | 花王株式会社 | 脂肪族ニトリルの製造方法 |
WO2009127651A1 (de) * | 2008-04-15 | 2009-10-22 | Rpc Bramlage Gmbh | Spender |
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2011
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2012
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DE912334C (de) * | 1952-06-08 | 1954-05-28 | Phrix Werke Ag | Verfahren zum Herstellen von Dehydroschleimsaeuredinitril |
DE2020866A1 (de) * | 1970-04-29 | 1971-11-18 | Basf Ag | Verfahren zur Herstellung von Hydroxy- und Aminobenzonitrilen |
JPH093030A (ja) * | 1995-06-21 | 1997-01-07 | Huels Ag | 2−ヒドロキシベンゾニトリルの製造法 |
JP2006523671A (ja) * | 2003-04-15 | 2006-10-19 | ファイザー・インク | PPAR調節剤としてのα置換カルボン酸 |
US20110288324A1 (en) * | 2008-12-04 | 2011-11-24 | Roland Jacquot | Method for manufacturing compounds including nitrile functions |
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TETRAHEDRON LETTERS, vol. 38(27), JPN6016026147, 1997, pages 4811 - 4814, ISSN: 0003354588 * |
モリソンボイド有機化学(中)第6版, vol. 第6版, JPN7016001879, 16 May 1994 (1994-05-16), pages 1044 - 1047, ISSN: 0003354589 * |
Also Published As
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BR112014015512A8 (pt) | 2017-07-04 |
CN103998438B (zh) | 2017-05-10 |
WO2013087765A1 (fr) | 2013-06-20 |
CN103998438A (zh) | 2014-08-20 |
US20140343304A1 (en) | 2014-11-20 |
EP2791124A1 (fr) | 2014-10-22 |
JP6113746B2 (ja) | 2017-04-12 |
FR2984322B1 (fr) | 2013-12-20 |
EP2791124B1 (fr) | 2017-06-07 |
FR2984322A1 (fr) | 2013-06-21 |
BR112014015512B1 (pt) | 2019-08-13 |
BR112014015512A2 (pt) | 2017-06-13 |
US9133153B2 (en) | 2015-09-15 |
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