JP5579192B2 - ニトリル基を有する化合物の製造プロセス - Google Patents
ニトリル基を有する化合物の製造プロセス Download PDFInfo
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- JP5579192B2 JP5579192B2 JP2011538959A JP2011538959A JP5579192B2 JP 5579192 B2 JP5579192 B2 JP 5579192B2 JP 2011538959 A JP2011538959 A JP 2011538959A JP 2011538959 A JP2011538959 A JP 2011538959A JP 5579192 B2 JP5579192 B2 JP 5579192B2
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- ammonium
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- 238000000034 method Methods 0.000 title claims description 35
- 150000001875 compounds Chemical class 0.000 title claims description 27
- 125000002560 nitrile group Chemical group 0.000 title description 7
- 239000003054 catalyst Substances 0.000 claims description 32
- 238000000855 fermentation Methods 0.000 claims description 23
- 230000004151 fermentation Effects 0.000 claims description 23
- 239000007864 aqueous solution Substances 0.000 claims description 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 16
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 claims description 11
- IAHFWCOBPZCAEA-UHFFFAOYSA-N succinonitrile Chemical compound N#CCCC#N IAHFWCOBPZCAEA-UHFFFAOYSA-N 0.000 claims description 10
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- NHJPVZLSLOHJDM-UHFFFAOYSA-N azane;butanedioic acid Chemical compound [NH4+].[NH4+].[O-]C(=O)CCC([O-])=O NHJPVZLSLOHJDM-UHFFFAOYSA-N 0.000 claims description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 150000002430 hydrocarbons Chemical group 0.000 claims description 6
- FLDCSPABIQBYKP-UHFFFAOYSA-N 5-chloro-1,2-dimethylbenzimidazole Chemical compound ClC1=CC=C2N(C)C(C)=NC2=C1 FLDCSPABIQBYKP-UHFFFAOYSA-N 0.000 claims description 5
- 239000001741 Ammonium adipate Substances 0.000 claims description 5
- 235000019293 ammonium adipate Nutrition 0.000 claims description 5
- 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 5
- 235000000346 sugar Nutrition 0.000 claims description 5
- 238000001354 calcination Methods 0.000 claims description 4
- 150000008163 sugars Chemical class 0.000 claims description 4
- 239000002028 Biomass Substances 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000377 silicon dioxide Substances 0.000 claims description 3
- 230000009466 transformation Effects 0.000 claims description 3
- PHKGGXPMPXXISP-DFWYDOINSA-N azanium;(4s)-4-amino-5-hydroxy-5-oxopentanoate Chemical compound [NH4+].[O-]C(=O)[C@@H]([NH3+])CCC([O-])=O PHKGGXPMPXXISP-DFWYDOINSA-N 0.000 claims description 2
- 239000012620 biological material Substances 0.000 claims description 2
- OKUGAOMPLZNWRT-UHFFFAOYSA-N diazanium;pentanedioate Chemical compound [NH4+].[NH4+].[O-]C(=O)CCCC([O-])=O OKUGAOMPLZNWRT-UHFFFAOYSA-N 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 235000013917 monoammonium glutamate Nutrition 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 125000001931 aliphatic group Chemical class 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000012808 vapor phase Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 description 14
- 239000000243 solution Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 8
- 239000007858 starting material Substances 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000001384 succinic acid Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- -1 amine compounds Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001720 carbohydrates Chemical class 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000005504 petroleum refining Methods 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 229910021419 crystalline silicon Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- XISDQKHUFKOCRD-UHFFFAOYSA-N diazanium;hexadecanedioate Chemical compound [NH4+].[NH4+].[O-]C(=O)CCCCCCCCCCCCCCC([O-])=O XISDQKHUFKOCRD-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000005669 hydrocyanation reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/02—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
- C07C255/04—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton containing two cyano groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/20—Preparation of carboxylic acid nitriles by dehydration of carboxylic acid amides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/182—Phosphorus; Compounds thereof with silicon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/22—Preparation of carboxylic acid nitriles by reaction of ammonia with carboxylic acids with replacement of carboxyl groups by cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
Description
本発明のプロセスは、結晶質シリコンオルソホスフェート(orthophosphate)を含む触媒の存在下で、アンモニアを、一般式II:(H4NOOC)x−(R1)−(COONH4)yの有機二酸(diacid)の塩と反応させるステップを含む。但しx、y及びR1は、上記式と同じ意味を有する。
この条件下では、NH3/コハク酸アンモニウムのモル比は10である。
コハク酸の20重量%濃度水溶液を使用する以外は、実施例1と同様に行った。
触媒床は、前記実施例と同様である。活性化処理に続き、触媒床にアンモニア流を2l/hで通過させ、同時にコハク酸水溶液を速度4ml/hで注入した。
これら条件下で、NH3/コハク酸のモル比は10である。凝縮液を回収し、GCにより分析した。
5時間注入後のスクシノニトリルの収率は、70%であった。
触媒床性能が経済的最適範囲より下になった場合、触媒床は下記手順に従い再生できる。但し、下記は単に例示のためにのみ記載されている。
Claims (9)
- 一般式I:(NC)x−R1(CN)yの化合物(但し、R1は、飽和又は不飽和であって、直鎖状又は分岐状の炭化水素基であり、1〜20炭素原子を含み、ヘテロ原子を含んでもよい炭化水素基を表し、x及びyは0又は1を表し、(x+y)は1又は2である。)を製造するプロセスであり、
気体蒸気(vapour)相中、式Si3(PO4)4のシリコンオルソホスフェートを含む触媒の存在下、300℃〜450℃の温度で、アンモニアを、一般式II:(H4NOOC)x−(R1)−(COONH4)yの化合物と反応させるステップ(ただし、一般式IIの化合物は水溶液の形態であり、該水溶液は、糖類を含む媒質の生物学的変換から得られる発酵リカーであり、直接的に使用されるか、媒質からの生物学的材料又はバイオマスを分離した後に使用される)を含むプロセス。 - 上記水溶液中の一般式IIの化合物の濃度は1重量%を超える、請求項1記載のプロセス。
- 上記水溶液中の一般式IIの化合物の濃度は1〜30重量%である、請求項2記載のプロセス。
- 生物学的変換から得られる発酵媒質が、バイオマスから分離後に使用される、請求項1記載のプロセス。
- 一般式IIの化合物は、コハク酸アンモニウム、アジピン酸アンモニウム、グルタミン酸アンモニウム、グルタール酸アンモニウム、脂肪族二酸のアンモニウム塩、ヘキサデカン二酸アンモニウムからなる群から選ばれる、請求項1〜4いずれか1項記載のプロセス。
- 反応は、固定触媒床を備えた反応器中で行われる、請求項1〜5いずれか1項記載のプロセス。
- 触媒は、シリカにリン酸を含浸し、空気中で焼成することにより得られる、請求項1〜6いずれか1項記載のプロセス。
- 焼成は、400℃〜800℃の温度で行われる、請求項7記載のプロセス。
- 一般式Iの化合物は、アジポニトリル及びスクシノニトリルの群から選ばれる、請求項1〜8いずれか1項記載のプロセス。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0858264 | 2008-12-04 | ||
FR0858264A FR2939432B1 (fr) | 2008-12-04 | 2008-12-04 | Procede de fabrication de composes comprenant des fonctions nitriles |
PCT/EP2009/065872 WO2010063632A1 (fr) | 2008-12-04 | 2009-11-26 | Procede de fabrication de composes comprenant des fonctions nitriles |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2012510971A JP2012510971A (ja) | 2012-05-17 |
JP5579192B2 true JP5579192B2 (ja) | 2014-08-27 |
Family
ID=40785536
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011538959A Active JP5579192B2 (ja) | 2008-12-04 | 2009-11-26 | ニトリル基を有する化合物の製造プロセス |
Country Status (11)
Country | Link |
---|---|
US (1) | US8501979B2 (ja) |
EP (1) | EP2365964B1 (ja) |
JP (1) | JP5579192B2 (ja) |
KR (1) | KR101345023B1 (ja) |
CN (1) | CN102239139B (ja) |
ES (1) | ES2621799T3 (ja) |
FR (1) | FR2939432B1 (ja) |
PL (1) | PL2365964T3 (ja) |
RU (1) | RU2478613C2 (ja) |
SG (1) | SG171925A1 (ja) |
WO (1) | WO2010063632A1 (ja) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR112012031597A2 (pt) | 2010-06-16 | 2017-05-23 | Bioamber Sas | processos para produzir hexametilenodiamina (hmd), adiponitrilo (adn), adipamida (adm) e derivados dos mesmos. |
CN103140467A (zh) * | 2010-06-16 | 2013-06-05 | 生物琥珀酸有限公司 | 己二胺(hmd)、己二腈(adn)、己二酰胺(adm)及其衍生物的制备方法 |
US9073867B2 (en) | 2011-04-09 | 2015-07-07 | Amyris, Inc. | Process for preparing caprolactam and polyamides therefrom |
FR2984322B1 (fr) * | 2011-12-16 | 2013-12-20 | Rhodia Operations | Procede de fabrication de composes comprenant des fonctions nitriles |
MY169922A (en) | 2012-10-01 | 2019-06-17 | Asahi Kasei Chemicals Corp | Method for stopping ammoxidation |
HRP20230021T1 (hr) * | 2013-10-03 | 2023-02-17 | Syngenta Participations Ag | Fungicidni pripravci |
CN106146345B (zh) * | 2015-04-17 | 2018-05-04 | 中国石油天然气股份有限公司 | 己二酸液相法生产己二腈的方法 |
CN106140234B (zh) * | 2015-04-17 | 2019-04-05 | 中国石油天然气股份有限公司 | 用于生产己二腈的固体磷酸催化剂及其制备方法 |
CN108821997B (zh) * | 2018-06-01 | 2021-03-16 | 重庆华峰聚酰胺有限公司 | 一种己二腈的制备方法及其产品 |
CN110511162B (zh) * | 2019-06-11 | 2021-01-05 | 中国科学院过程工程研究所 | 一种己二腈的制备方法 |
CN112920077B (zh) * | 2021-02-05 | 2023-07-07 | 大连和源化学科技开发有限公司 | 一种多相连续催化一步合成己二腈的方法 |
CN115819278A (zh) * | 2021-09-17 | 2023-03-21 | 中国石油化工股份有限公司 | 一种制备丁二腈的工艺及系统 |
Family Cites Families (14)
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---|---|---|---|---|
SU100776A1 (ru) * | 1954-11-02 | 1954-11-30 | Е.С. Жданович | Способ получени ацетонитрила |
GB797945A (en) * | 1954-11-05 | 1958-07-09 | Toyo Koatsu Ind Inc | A process for the preparation of catalysts for use in the manufacture of aliphatic or alicyclic dinitriles |
DE1196179B (de) * | 1962-05-18 | 1965-07-08 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Adipinsaeuredinitril |
US3393222A (en) * | 1964-07-23 | 1968-07-16 | Bayer Ag | Process for the production of nitriles |
DE1268610B (de) * | 1964-07-23 | 1968-05-22 | Bayer Ag | Verfahren zur Herstellung von Carbonsaeurenitrilen |
GB1397729A (en) * | 1971-10-11 | 1975-06-18 | Ici Ltd | Phosphate catalysts used in adiponitrile manufacture |
JPS57206394A (en) * | 1981-06-16 | 1982-12-17 | Mitsui Petrochem Ind Ltd | Preparation of dicarboxylic acid |
DE3510876A1 (de) * | 1985-03-26 | 1986-10-02 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von aliphatischen dinitrilen |
US5487987A (en) * | 1993-09-16 | 1996-01-30 | Purdue Research Foundation | Synthesis of adipic acid from biomass-derived carbon sources |
JPH10218903A (ja) * | 1997-02-07 | 1998-08-18 | Canon Inc | 糖鎖高分子化合物、その合成方法および分解方法 |
US6005134A (en) * | 1998-06-25 | 1999-12-21 | Kao Corporation | Process for the preparation of aliphatic nitriles |
JP2003235592A (ja) * | 2002-02-13 | 2003-08-26 | Mitsubishi Chemicals Corp | 有機酸の製造方法 |
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 |
JP2006288361A (ja) * | 2005-04-09 | 2006-10-26 | Toru Ueda | 稲藁・廃木材等の農林業系廃棄物からの生分解性プラスチック製造用コハク酸生産方法及び装置 |
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- 2009-11-26 ES ES09764489.2T patent/ES2621799T3/es active Active
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Publication number | Publication date |
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FR2939432B1 (fr) | 2012-06-22 |
CN102239139B (zh) | 2015-07-15 |
KR20110082078A (ko) | 2011-07-15 |
FR2939432A1 (fr) | 2010-06-11 |
EP2365964B1 (fr) | 2017-01-18 |
US20110288324A1 (en) | 2011-11-24 |
ES2621799T3 (es) | 2017-07-05 |
SG171925A1 (en) | 2011-07-28 |
PL2365964T3 (pl) | 2017-07-31 |
RU2478613C2 (ru) | 2013-04-10 |
WO2010063632A1 (fr) | 2010-06-10 |
EP2365964A1 (fr) | 2011-09-21 |
CN102239139A (zh) | 2011-11-09 |
KR101345023B1 (ko) | 2013-12-26 |
JP2012510971A (ja) | 2012-05-17 |
RU2011127213A (ru) | 2013-01-10 |
US8501979B2 (en) | 2013-08-06 |
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