CN1065154C - 回收废酸催化剂的方法 - Google Patents
回收废酸催化剂的方法 Download PDFInfo
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- CN1065154C CN1065154C CN95107134A CN95107134A CN1065154C CN 1065154 C CN1065154 C CN 1065154C CN 95107134 A CN95107134 A CN 95107134A CN 95107134 A CN95107134 A CN 95107134A CN 1065154 C CN1065154 C CN 1065154C
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- 238000000034 method Methods 0.000 title claims abstract description 25
- 239000003377 acid catalyst Substances 0.000 title claims abstract description 22
- 230000008569 process Effects 0.000 title claims abstract description 13
- 238000011084 recovery Methods 0.000 title abstract 2
- 238000005804 alkylation reaction Methods 0.000 claims abstract description 36
- 230000029936 alkylation Effects 0.000 claims abstract description 26
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 11
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 11
- -1 sulphonic acid ester Chemical class 0.000 claims abstract description 11
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 10
- 150000001336 alkenes Chemical class 0.000 claims abstract description 9
- 230000003197 catalytic effect Effects 0.000 claims abstract description 7
- 239000000284 extract Substances 0.000 claims abstract description 5
- 239000006286 aqueous extract Substances 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 230000026030 halogenation Effects 0.000 claims description 2
- 238000005658 halogenation reaction Methods 0.000 claims description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 23
- 150000002148 esters Chemical class 0.000 abstract description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 238000001704 evaporation Methods 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000000605 extraction Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 4
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- 238000003442 catalytic alkylation reaction Methods 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 235000013847 iso-butane Nutrition 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
Classifications
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- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0215—Sulfur-containing compounds
- B01J31/0225—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts
- B01J31/0227—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts being perfluorinated, i.e. comprising at least one perfluorinated moiety as substructure in case of polyfunctional compounds
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0215—Sulfur-containing compounds
- B01J31/0225—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/40—Regeneration or reactivation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/56—Addition to acyclic hydrocarbons
- C07C2/58—Catalytic processes
- C07C2/62—Catalytic processes with acids
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/025—Sulfonic acids
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Abstract
一种从烷基化流出物流的含水萃取物中回收磺酸催化剂的方法，包括如下步骤：
蒸发萃取物，得到磺酸催化剂的水合物；
水合物与含烯烃的烃物流反应，产生其相应的磺酸酯；和
在烷基化条件下，将酸酯引入到烃原料与烯属烷基化剂的烷基化过程中，在烷基化过程中，磺酸酯分解成具有催化活性的酸形式。
Description
本发明涉及在酸催化剂存在下，脂族烃催化烷基化的某些改进。更准确地说，本发明涉及从在催化烷基化过程期间形成的油副产物中回收这样的催化剂。
脂族烃与烯烃的酸催化烷基化是人们熟知的制备高辛烷值汽油产品的方法。通常，是在液相中，在有强酸催化剂存在下，通过烷烃与烯烃反应来完成脂族烃的烷基化。
工业烷基化过程常用的酸是氟化氢和硫酸。
美国专利5，220，095公开了在脂族烃与烯烃烷基化中，利用氟化的磺酸作为有效的烷基化催化剂，该专利在此作为参考文献。在公开的方法中，在装有极性接触物料的固定床烷基化反应器中，包含烃基质和烯属烷基化剂的过程物流与氟化的磺酸催化剂接触进行反应。接触物料与吸附在接触物料限定区域内的氟化磺酸催化剂形成反应区。在该反应区中，通过吸附在接触物料上的氟化磺酸的催化作用，使过程物流在烷基化条件下转化为烷基化烃的产物流。
在烷基化反应期间，因为与流过反应区并在其中反应的过程物料的相互作用，酸催化剂和反应区如同一个适当限定的区域在反应器两端之间移动。
当氟化磺酸沿接触物料流动时，其基本上保持催化活性，并且当反应区到达反应器出口时，氟化磺酸仍具有催化活性。
虽然，当过程物流到达烷基化反应器出口端时，通过引入到烷基化反应器中的过程物流的反向流动可以再利用该酸催化剂而不回收该酸，但少量该酸催化剂将连续被烷基化过程期间由付反应形成的酸可溶的油副产物吸收。该油和酸催化剂一样，如同一个可移动区域被吸附在靠近反应区的载体物质上。因此，每当油区带到达反应器任一端时，可以从反应器回收该油。
虽然，该油仅含有少量废酸催化剂，但为了改善烷基化过程的经济性，就要求回收该催化剂。但是不可以使用象蒸馏油或从油中直接萃取酸这些常用的方法，因为油中的酸催化剂和碱性组分相互激烈反应。
上述美国专利公开了用水洗涤，通过萃取烷基化反应器的流出物来回收废氟化磺酸。采用公开的方法，通过浓缩和蒸馏步骤，来处理得到的酸水溶液。
业已发现，通过用将酸转化为其水合物，并用合适的酯化剂处理该水合物来获得该酸的酯的简单方法，可改进从烷基化流出物流中萃取废酸催化剂。然后，该酯可被萃取到烃物料中，并循环到烷基化过程。
因此，本发明的主要实施方案是指从烷基化流出物的含水萃取物中回收磺酸催化剂的方法，该方法包括如下步骤：
蒸发萃取物，得到磺酸催化剂的水合物；
该水合物与含烯烃的烃物流反应，生成其相应的磺酸酯；和
在烷基化条件下，将该酸酯加入到过程中，以使烃原料与烯属烷基化剂进行烷基化，由此，在烷基化过程中，磺酸酯分解成其具有催化活性的酸形式。
本发明的方法用于回收卤化的烷基磺酸烷基化催化剂，具体说，是回收三氟甲烷磺酸。
在用工业烷基化设备来回收废酸催化剂的期间，酸可溶油的萃取可以在搅拌的反混反应器中进行。
此外，也可在连续操作的萃取柱中，用与烯属烃物流逆流的含水萃取液进行萃取。
在另一个优选的实施方案中，用含丁烯作为烯属烷基化剂的烷基化过程物流来处理酸水合物，其在回收酸水合物期间进一步用作酯化化合物。
在下文更详细的描述中，通过描述本发明的具体实施方案的实施例对本发明作进一步说明。
实施例
在本实施例中，按照本发明下述具体实施方案，对相当于1．2∶1水酸摩尔比的含水量为13％(w／w)的三氟甲烷磺酸水合物进行处理。通过蒸发该酸的水溶液制得酸水合物。
在下面的实验中，将100ml酸水合物(总量170g，酸147g+水22g)加到150ml萃取容器中。
将含5％2-丁烯(在异丁烷中)的烃原料5ml／min的速度通过该容器。萃取容器的流出物在加到烷基化反应器前，先通过一个装有干硅石(Merck 100，0．2-0．5mm)的300ml干燥柱。在烷基化反应器中，2-丁烯转化为烷基化物，并将回收的磺酸酯转化为其催化活性的酸形式，其聚集在反应器中。在每个实验结束时，将超过初始装入酸的过量酸除去，并测定除去的酸的含水量。
在第一个实验中，在烷基化反应器中，最初装入6ml(10g)无水三氟甲烷磺酸(0．28％水)。使1240g进料物流(62g 2-丁烯)在25℃下反应后，从反应器中除去过量酸，反应器中留下相当于实验开始时的酸量。将含水量为0．88％的9．4g过量酸除去。
在第二个实验中，使用第一个实验的烷基化反应器而不加入新鲜的无水酸。将100ml酸水合物再装入该萃取容器，并更换无水容器中的硅石。
使1928g的5％ 2-丁烯(96．4g烯烃)在40℃下通过萃取容器、通过干燥柱和烷基化反应器之后，将过量的8．7g酸(94．5％酸，1．6％水)回收。
Claims (6)
1．一种从烷基化流出物流的含水萃取物中回收磺酸催化剂的方法，包括如下步骤：
蒸发萃取物，得到磺酸催化剂的水合物；
水合物与含烯烃的烃物流反应，产生其相应的磺酸酯；和
在烷基化条件下，将所述磺酸酯加入到烃原料与烯属烷基化剂的烷基化过程中，在烷基化过程中，磺酸酯分解成其具有催化活性的酸形式。
2．权利要求1的方法，其中磺酸催化剂包括卤化的烷基磺酸。
3．权利要求1的方法，其中磺酸催化剂包括全氟化烷基磺酸。
4．权利要求1的方法，其中磺酸催化剂包括三氟甲烷磺酸。
5．权利权利1的方法，其中含烯烃的烃物流是烷基化过程物流。
6．权利要求1方法，其中烯烃包括正丁烯。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK0622/94 | 1994-06-02 | ||
| DK199400622A DK173114B1 (da) | 1994-06-02 | 1994-06-02 | Fremgangsmåde til genvinding af brugt sulfonsyrekatalysator samt anvendelse af fremgangsmåden |
| DK0622/1994 | 1994-06-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1119555A CN1119555A (zh) | 1996-04-03 |
| CN1065154C true CN1065154C (zh) | 2001-05-02 |
Family
ID=8095665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN95107134A Expired - Fee Related CN1065154C (zh) | 1994-06-02 | 1995-06-01 | 回收废酸催化剂的方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5625114A (zh) |
| EP (1) | EP0685443B1 (zh) |
| JP (1) | JPH0852363A (zh) |
| CN (1) | CN1065154C (zh) |
| DE (1) | DE69504133T2 (zh) |
| DK (1) | DK173114B1 (zh) |
| ES (1) | ES2120662T3 (zh) |
| RU (1) | RU2139759C1 (zh) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK172906B1 (da) * | 1996-06-17 | 1999-09-27 | Topsoe Haldor As | Fremgangsmåde til fjernelse af korrosive bestanddele fra en fluidastrøm |
| DK26298A (da) * | 1998-02-27 | 1999-08-28 | Haldor Topsoe As | Fremgangsmåde til genvinding af sulfonsyreester ud fra carbonhydridstrøm |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1040332A (zh) * | 1988-07-04 | 1990-03-14 | 三井石油化学工业株式会社 | 含氟芳族磺酸催化剂及其制法和用途 |
| EP0433954A1 (en) * | 1989-12-18 | 1991-06-26 | Haldor Topsoe A/S | Alkylation process |
| EP0595755A1 (en) * | 1992-10-27 | 1994-05-04 | Haldor Topsoe A/S | Method of recovering acid catalyst from acid catalyzed processes |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5284993A (en) * | 1992-09-21 | 1994-02-08 | Phillips Petroleum Company | Alkylation catalyst regeneration |
| DK170019B1 (da) * | 1993-03-12 | 1995-05-01 | Topsoe Haldor As | Fremgangsmåde til genvinding af brugt fluoreret sulfonsyrekatalysator fra en alkyleringsproces |
| DK171701B1 (da) * | 1993-07-06 | 1997-04-01 | Topsoe Haldor As | Fremgangsmåde til genvinding af brugt syrekatalysator fra alkylering af carbonhydrider |
-
1994
- 1994-06-02 DK DK199400622A patent/DK173114B1/da not_active IP Right Cessation
-
1995
- 1995-05-23 ES ES95107835T patent/ES2120662T3/es not_active Expired - Lifetime
- 1995-05-23 DE DE69504133T patent/DE69504133T2/de not_active Expired - Fee Related
- 1995-05-23 EP EP95107835A patent/EP0685443B1/en not_active Expired - Lifetime
- 1995-05-25 US US08/450,389 patent/US5625114A/en not_active Expired - Fee Related
- 1995-06-01 CN CN95107134A patent/CN1065154C/zh not_active Expired - Fee Related
- 1995-06-01 JP JP7135377A patent/JPH0852363A/ja not_active Withdrawn
- 1995-06-02 RU RU95108875/04A patent/RU2139759C1/ru not_active IP Right Cessation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1040332A (zh) * | 1988-07-04 | 1990-03-14 | 三井石油化学工业株式会社 | 含氟芳族磺酸催化剂及其制法和用途 |
| EP0433954A1 (en) * | 1989-12-18 | 1991-06-26 | Haldor Topsoe A/S | Alkylation process |
| EP0595755A1 (en) * | 1992-10-27 | 1994-05-04 | Haldor Topsoe A/S | Method of recovering acid catalyst from acid catalyzed processes |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0852363A (ja) | 1996-02-27 |
| ES2120662T3 (es) | 1998-11-01 |
| EP0685443A1 (en) | 1995-12-06 |
| RU2139759C1 (ru) | 1999-10-20 |
| US5625114A (en) | 1997-04-29 |
| DK173114B1 (da) | 2000-01-31 |
| EP0685443B1 (en) | 1998-08-19 |
| DE69504133T2 (de) | 1998-12-24 |
| DE69504133D1 (de) | 1998-09-24 |
| DK62294A (da) | 1995-12-03 |
| RU95108875A (ru) | 1997-05-10 |
| CN1119555A (zh) | 1996-04-03 |
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