ES2196841T3 - Procedimiento de separacion y de purificacion de acido adipico. - Google Patents
Procedimiento de separacion y de purificacion de acido adipico.Info
- Publication number
- ES2196841T3 ES2196841T3 ES99937924T ES99937924T ES2196841T3 ES 2196841 T3 ES2196841 T3 ES 2196841T3 ES 99937924 T ES99937924 T ES 99937924T ES 99937924 T ES99937924 T ES 99937924T ES 2196841 T3 ES2196841 T3 ES 2196841T3
- Authority
- ES
- Spain
- Prior art keywords
- catalyst
- water
- cyclohexane
- adipic acid
- distillation residue
- 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 - Lifetime
Links
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 title abstract 8
- 235000011037 adipic acid Nutrition 0.000 title abstract 4
- 239000001361 adipic acid Substances 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 3
- 238000000746 purification Methods 0.000 title abstract 3
- 238000000926 separation method Methods 0.000 title abstract 2
- 239000003054 catalyst Substances 0.000 abstract 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 4
- 238000004821 distillation Methods 0.000 abstract 4
- 239000012071 phase Substances 0.000 abstract 3
- 238000002425 crystallisation Methods 0.000 abstract 2
- 230000008025 crystallization Effects 0.000 abstract 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 238000010908 decantation Methods 0.000 abstract 1
- 229910001882 dioxygen Inorganic materials 0.000 abstract 1
- 238000000909 electrodialysis Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000003456 ion exchange resin Substances 0.000 abstract 1
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 1
- 150000002596 lactones Chemical class 0.000 abstract 1
- 239000007791 liquid phase Substances 0.000 abstract 1
- 238000000622 liquid--liquid extraction Methods 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 238000000638 solvent extraction Methods 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Procedimiento de tratamiento de la mezcla de reacción resultante de la oxidación directa de ciclohexano a ácido adípico por oxígeno molecular, en un disolvente orgánico y en presencia de un catalizador, caracterizado porque el citado procedimiento comprende: - una decantación en dos fases líquidas: una fase superior esencialmente ciclohexánica y una fase inferior que contiene esencialmente el disolvente, los diácidos formados, el catalizador y una parte de otros productos de la reacción y el ciclohexano no transformado; - una destilación de la citada fase inferior, que permite separar, por una parte, un destilado que contiene al menos una parte de los compuestos más volátiles tales como el disolvente orgánico, agua así como ciclohexano no transformado, ciclohexanona, ciclohexanol, ésteres de ciclohexilo y lactonas eventualmente presentes, y por otra parte, el residuo de destilación que contiene los diácidos formados y el catalizador; - una separación del catalizador del residuo de destilación obtenido anteriormente, bien mediante cristalización en agua, mediante electrodiálisis o mediante filtración a través de una resina de intercambio iónico, después de haber disuelto dicho residuo de destilación en agua, bien por lavado con agua o bien por extracción líquido-líquido; - un tratamiento de purificación reductor y/o oxidante del ácido adípico en disolución acuosa; - una cristalización anterior o posterior al tratamiento de purificación, cuando no se haya realizado para separar el catalizador; y - una recristalización en agua del ácido adípico.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9802928A FR2775685B1 (fr) | 1998-03-05 | 1998-03-05 | Procede de separation et de purification de l'acide adipique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2196841T3 true ES2196841T3 (es) | 2003-12-16 |
Family
ID=9523876
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99937924T Expired - Lifetime ES2196841T3 (es) | 1998-03-05 | 1999-02-24 | Procedimiento de separacion y de purificacion de acido adipico. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6787669B1 (es) |
| EP (1) | EP1060157B1 (es) |
| JP (1) | JP3938843B2 (es) |
| KR (1) | KR100489490B1 (es) |
| CN (1) | CN1173920C (es) |
| AR (1) | AR016182A1 (es) |
| BR (1) | BR9908395B1 (es) |
| CA (1) | CA2322701A1 (es) |
| DE (1) | DE69909063T2 (es) |
| ES (1) | ES2196841T3 (es) |
| FR (1) | FR2775685B1 (es) |
| ID (1) | ID28021A (es) |
| PL (1) | PL342734A1 (es) |
| RU (1) | RU2214392C2 (es) |
| SK (1) | SK13112000A3 (es) |
| TW (1) | TW506966B (es) |
| UA (1) | UA70314C2 (es) |
| WO (1) | WO1999044980A1 (es) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2784099B1 (fr) * | 1998-09-14 | 2000-11-24 | Rhone Poulenc Fibres | Procede de separation et de purification de l'acide carboxylique issu de l'oxydation directe d'un hydrocarbure |
| FR2810904B1 (fr) * | 2000-06-28 | 2002-12-20 | Rhodia Polyamide Intermediates | Procede d'oxydation d'hydrocarbures, d'alcools et/ou de cetones |
| FR2846651B1 (fr) * | 2002-10-30 | 2006-06-16 | Rhodia Polyamide Intermediates | Procede de fabrication d'acides carboxyliques |
| FR2887248B1 (fr) * | 2005-06-17 | 2007-08-03 | Rhodia Chimie Sa | Procede de fabrication d'acides carboxyliques |
| FR2946646B1 (fr) * | 2009-06-16 | 2012-09-21 | Rhodia Operations | Procede de production de cristaux d'acide adipique |
| US20120156761A1 (en) | 2009-07-02 | 2012-06-21 | Verdezyne, Inc. | Biological methods for preparing adipic acid |
| FR2953830B1 (fr) * | 2009-12-14 | 2012-01-20 | Arkema France | Procede de fabrication d'acroleine et/ou d'acide acrylique a partir de glycerol |
| CN102757332B (zh) * | 2011-04-27 | 2015-07-01 | 中国石油化工集团公司 | 一种环己烷氧化产物的处理方法 |
| US8343752B2 (en) | 2011-05-03 | 2013-01-01 | Verdezyne, Inc. | Biological methods for preparing adipic acid |
| US8728798B2 (en) | 2011-05-03 | 2014-05-20 | Verdezyne, Inc. | Biological methods for preparing adipic acid |
| CN106478404B (zh) * | 2016-09-23 | 2019-04-05 | 重庆华峰化工有限公司 | 精己二酸的大规模工业化连续生产方法 |
| CN108084012B (zh) * | 2016-11-22 | 2019-12-31 | 中国科学院大连化学物理研究所 | 一种氧化环己酮制备己二酸的方法 |
| CN113248366A (zh) * | 2020-01-27 | 2021-08-13 | 英威达纺织（英国）有限公司 | 己二腈的纯化 |
| IT202000017368A1 (it) * | 2020-07-16 | 2022-01-16 | Radici Chimica S P A | Purificazione di acidi dicarbossilici alifatici prodotti mediante processi biotecnologici |
| CN116986984A (zh) * | 2023-08-03 | 2023-11-03 | 浙江贝诺机械有限公司 | 一种己二酸晶体复融提纯再结晶方法 |
| CN118750888B (zh) * | 2024-06-12 | 2025-04-18 | 重庆华峰化工有限公司 | 一种环己烷催化氧化法氧化液的分离系统及方法 |
| TWI904720B (zh) * | 2024-06-14 | 2025-11-11 | 國立成功大學 | 製備2-羥基己二酸及己二酸的方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE764488C (de) * | 1940-07-17 | 1953-06-15 | Ig Farbenindustrie Ag | Verfahren zum Reinigen von Adipinsaeure und ihren Homologen |
| FR1266886A (fr) * | 1959-09-08 | 1961-07-17 | Chemstrand Corp | Perfectionnements apportés à la fabrication d'acide adipique |
| JPS49812B1 (es) * | 1970-04-03 | 1974-01-10 | ||
| US3933930A (en) * | 1975-03-06 | 1976-01-20 | Celanese Corporation | Hexanediol from cyclohexane |
| DE2624472C3 (de) * | 1976-06-01 | 1980-01-17 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Reinigung von Adipinsäure |
| DE2721858C3 (de) * | 1977-05-14 | 1979-11-08 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Gewinnung von Adipinsäure |
| TW238299B (es) * | 1992-09-25 | 1995-01-11 | Bayer Ag | |
| FR2722783B1 (fr) * | 1994-07-21 | 1996-08-30 | Rhone Poulenc Chimie | Procede de preparation d'acide adipique par oxydattion directe du cyclohexane et recyclage du catalyseur |
| DE4428977A1 (de) * | 1994-08-16 | 1996-02-22 | Bayer Ag | Verfahren zur Aufarbeitung eines Nebenproduktstroms |
| FR2746671B1 (fr) * | 1996-04-02 | 1998-09-25 | Rhone Poulenc Fibres | Procede de separation d'un catalyseur par electrodialyse membranaire |
| FR2757155B1 (fr) * | 1996-12-12 | 1999-11-12 | Rhone Poulenc Fibres | Procede de traitement de melanges reactionnels issus de l'oxydation du cyclohexane |
-
1998
- 1998-03-05 FR FR9802928A patent/FR2775685B1/fr not_active Expired - Fee Related
-
1999
- 1999-02-24 CN CNB998035718A patent/CN1173920C/zh not_active Expired - Fee Related
- 1999-02-24 WO PCT/FR1999/000420 patent/WO1999044980A1/fr not_active Ceased
- 1999-02-24 JP JP2000534526A patent/JP3938843B2/ja not_active Expired - Fee Related
- 1999-02-24 SK SK1311-2000A patent/SK13112000A3/sk unknown
- 1999-02-24 KR KR10-2000-7009649A patent/KR100489490B1/ko not_active Expired - Fee Related
- 1999-02-24 PL PL99342734A patent/PL342734A1/xx unknown
- 1999-02-24 RU RU2000125108/04A patent/RU2214392C2/ru not_active IP Right Cessation
- 1999-02-24 CA CA002322701A patent/CA2322701A1/fr not_active Abandoned
- 1999-02-24 UA UA2000085113A patent/UA70314C2/uk unknown
- 1999-02-24 US US09/623,414 patent/US6787669B1/en not_active Expired - Fee Related
- 1999-02-24 ES ES99937924T patent/ES2196841T3/es not_active Expired - Lifetime
- 1999-02-24 EP EP99937924A patent/EP1060157B1/fr not_active Expired - Lifetime
- 1999-02-24 ID IDW20001686A patent/ID28021A/id unknown
- 1999-02-24 DE DE69909063T patent/DE69909063T2/de not_active Expired - Lifetime
- 1999-02-24 BR BRPI9908395-7A patent/BR9908395B1/pt not_active IP Right Cessation
- 1999-03-02 TW TW088103171A patent/TW506966B/zh not_active IP Right Cessation
- 1999-03-04 AR ARP990100906A patent/AR016182A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| PL342734A1 (en) | 2001-07-02 |
| CN1291971A (zh) | 2001-04-18 |
| EP1060157A1 (fr) | 2000-12-20 |
| BR9908395A (pt) | 2000-10-31 |
| KR20010034546A (ko) | 2001-04-25 |
| BR9908395B1 (pt) | 2009-08-11 |
| CA2322701A1 (fr) | 1999-09-10 |
| EP1060157B1 (fr) | 2003-06-25 |
| RU2214392C2 (ru) | 2003-10-20 |
| FR2775685B1 (fr) | 2000-12-29 |
| DE69909063D1 (de) | 2003-07-31 |
| WO1999044980A1 (fr) | 1999-09-10 |
| AR016182A1 (es) | 2001-06-20 |
| TW506966B (en) | 2002-10-21 |
| UA70314C2 (uk) | 2004-10-15 |
| JP3938843B2 (ja) | 2007-06-27 |
| ID28021A (id) | 2001-05-03 |
| DE69909063T2 (de) | 2004-04-29 |
| US6787669B1 (en) | 2004-09-07 |
| KR100489490B1 (ko) | 2005-05-16 |
| JP2002505314A (ja) | 2002-02-19 |
| SK13112000A3 (sk) | 2001-02-12 |
| CN1173920C (zh) | 2004-11-03 |
| FR2775685A1 (fr) | 1999-09-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2196841T3 (es) | Procedimiento de separacion y de purificacion de acido adipico. | |
| KR970015555A (ko) | 고순도 테레프탈산의 제조방법 | |
| ES2136298T3 (es) | Procedimiento de reciclaje del catalizador en la oxidacion directa de ciclohexano a acido adipico. | |
| KR101546464B1 (ko) | (메트)아크릴산의 연속 회수 방법 및 회수 장치 | |
| AR009663A1 (es) | Un procedimiento de tratamiento de mezclas reactivas provenientes de la reaccion de oxidacion del ciclohexano en acido adipico | |
| EP0818434A3 (en) | Process for the production of high-purity isophthalic acid | |
| ES2056469T3 (es) | Procedimiento de extraccion para la separacion de impurezas de filtrado de acido tereftalico. | |
| AR035992A1 (es) | Proceso para producir acido tereftalico puro con recuperacion mejorada de precursores, solvente y metil acetato | |
| JP3232678B2 (ja) | 酢酸の回収方法 | |
| BR9508815A (pt) | Processos para produzir um ácido dicarboxilico aromático e para realizar a separação de água de um veículo de fase líquida contendo pelo menos um corpo componente por destilação azeotrópica | |
| US5171868A (en) | Epoxidate treatment | |
| RU2000125108A (ru) | Способ выделения и очистки адипиновой кислоты | |
| RU97120887A (ru) | Способ обработки реакционных смесей, образующихся при окислении циклогексана | |
| MX9600930A (es) | Proceso para purificar acido acetico. | |
| US11034642B2 (en) | Method and apparatus for continuously recovering (meth)acrylic acid | |
| ES2374274T3 (es) | Procedimiento de purificar óxido de propileno. | |
| US3726917A (en) | Process for preparing adipic acid | |
| DE3720562C2 (es) | ||
| JPH0725814A (ja) | 高純度酢酸の製造方法 | |
| AR020437A1 (es) | Procedimiento para separar y purificar el acido carboxilico de la oxidacion directa de un hidrocarburo | |
| US2229532A (en) | Process for the purification of nitro aliphatic compounds | |
| JPS62149638A (ja) | アリルアルコ−ルの精製法 | |
| US9962625B2 (en) | Process for continuously recovering (meth)acrylic acid and apparatus for the process | |
| JPH06228126A (ja) | トリオキサンの合成方法 | |
| US1930054A (en) | Purification of organic acids |