CN102513148B - 一种苄叉二氯酸解反应联产苯甲醛和酰氯的催化剂和工艺 - Google Patents
一种苄叉二氯酸解反应联产苯甲醛和酰氯的催化剂和工艺 Download PDFInfo
- Publication number
- CN102513148B CN102513148B CN201110412138.9A CN201110412138A CN102513148B CN 102513148 B CN102513148 B CN 102513148B CN 201110412138 A CN201110412138 A CN 201110412138A CN 102513148 B CN102513148 B CN 102513148B
- Authority
- CN
- China
- Prior art keywords
- molecular sieve
- catalyst
- benzal chloride
- reaction
- chloride
- 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.)
- Active
Links
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 title claims abstract description 76
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 72
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 title claims abstract description 61
- 239000003054 catalyst Substances 0.000 title claims abstract description 61
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 150000001263 acyl chlorides Chemical class 0.000 title claims abstract description 35
- 238000000034 method Methods 0.000 title claims abstract description 31
- 230000008569 process Effects 0.000 title abstract description 8
- 239000002808 molecular sieve Substances 0.000 claims abstract description 69
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 69
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 39
- 150000007524 organic acids Chemical class 0.000 claims abstract description 38
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 10
- 239000010703 silicon Substances 0.000 claims abstract description 10
- 230000007704 transition Effects 0.000 claims abstract description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229910019142 PO4 Inorganic materials 0.000 claims description 6
- 229910002796 Si–Al Inorganic materials 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 239000004411 aluminium Substances 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 6
- 239000010452 phosphate Substances 0.000 claims description 6
- 102000040350 B family Human genes 0.000 claims description 5
- 108091072128 B family Proteins 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 4
- 229910017119 AlPO Inorganic materials 0.000 claims description 3
- 241000269350 Anura Species 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 239000000047 product Substances 0.000 abstract description 11
- 239000000126 substance Substances 0.000 abstract description 10
- 239000006227 byproduct Substances 0.000 abstract description 7
- 238000000926 separation method Methods 0.000 abstract description 4
- 230000009471 action Effects 0.000 abstract description 3
- 230000008901 benefit Effects 0.000 abstract description 2
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- URRHWTYOQNLUKY-UHFFFAOYSA-N [AlH3].[P] Chemical compound [AlH3].[P] URRHWTYOQNLUKY-UHFFFAOYSA-N 0.000 abstract 1
- CSDREXVUYHZDNP-UHFFFAOYSA-N alumanylidynesilicon Chemical compound [Al].[Si] CSDREXVUYHZDNP-UHFFFAOYSA-N 0.000 abstract 1
- 238000004939 coking Methods 0.000 abstract 1
- 238000004064 recycling Methods 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- 238000002360 preparation method Methods 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000007789 gas Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 238000005660 chlorination reaction Methods 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000005303 weighing Methods 0.000 description 5
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000010189 synthetic method Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000003750 conditioning effect Effects 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 2
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 240000005049 Prunus salicina Species 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000011968 lewis acid catalyst Substances 0.000 description 2
- 235000009018 li Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 241001502050 Acis Species 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- LBGPXIPGGRQBJW-UHFFFAOYSA-N Difenzoquat Chemical compound C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 LBGPXIPGGRQBJW-UHFFFAOYSA-N 0.000 description 1
- 241000692870 Inachis io Species 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019213 POCl3 Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- YSZKDKZFYUOELW-UHFFFAOYSA-N [diphenyl-(4-propan-2-ylcyclohexyl)methyl]benzene Chemical compound C1(=CC=CC=C1)C(C1CCC(CC1)C(C)C)(C1=CC=CC=C1)C1=CC=CC=C1 YSZKDKZFYUOELW-UHFFFAOYSA-N 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
- 229960000723 ampicillin Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- BULOCEWDRJUMEL-UHFFFAOYSA-N benzene formaldehyde Chemical compound C=O.C1=CC=CC=C1.C=O BULOCEWDRJUMEL-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000007172 homogeneous catalysis Methods 0.000 description 1
- 238000005647 hydrohalogenation reaction Methods 0.000 description 1
- 238000001027 hydrothermal synthesis Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- -1 m2g organic acid Chemical class 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 229960001783 nicardipine Drugs 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
循环次数 | 1 | 2 | 3 | 4 | 5 |
乙酸转化率(%) | 97.7 | 96.8 | 98.2 | 97.4 | 98.7 |
乙酰氯摩尔收率(%) | 97.7 | 96.8 | 98.2 | 97.4 | 98.7 |
苯甲醛摩尔收率(%) | 48.9 | 48.4 | 49.1 | 48.7 | 49.4 |
Claims (7)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201110412138.9A CN102513148B (zh) | 2011-12-12 | 2011-12-12 | 一种苄叉二氯酸解反应联产苯甲醛和酰氯的催化剂和工艺 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201110412138.9A CN102513148B (zh) | 2011-12-12 | 2011-12-12 | 一种苄叉二氯酸解反应联产苯甲醛和酰氯的催化剂和工艺 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102513148A CN102513148A (zh) | 2012-06-27 |
CN102513148B true CN102513148B (zh) | 2013-10-09 |
Family
ID=46284364
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201110412138.9A Active CN102513148B (zh) | 2011-12-12 | 2011-12-12 | 一种苄叉二氯酸解反应联产苯甲醛和酰氯的催化剂和工艺 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN102513148B (zh) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106397148A (zh) * | 2016-09-12 | 2017-02-15 | 江苏必康制药股份有限公司 | 二氯化苄水解方法 |
CN110963910B (zh) * | 2019-12-17 | 2022-05-20 | 南通市天时化工有限公司 | 一种苄叉二氯酸解法制备酰氯过程中真空系统的改进方法 |
CN116410070A (zh) * | 2021-12-31 | 2023-07-11 | 江苏优嘉植物保护有限公司 | 一种对氟间苯氧基苯甲醛的生产工艺 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1060650A (zh) * | 1990-10-11 | 1992-04-29 | 陈敏哲 | 联体法生产对(邻)氯苯甲醛、对(邻)氯苯甲酰氯 |
CN101070295A (zh) * | 2007-06-07 | 2007-11-14 | 江苏强盛化工有限公司 | 联产取代苯磺酰氯和取代苯甲酰氯的方法 |
CN101224431A (zh) * | 2008-01-30 | 2008-07-23 | 中国科学院山西煤炭化学研究所 | 甲醇一步法氧化合成甲缩醛的催化剂及其制法和应用 |
CN101898144A (zh) * | 2009-05-27 | 2010-12-01 | 中国石油天然气股份有限公司 | 一种含骨架杂原子的y型分子筛的催化裂化催化剂及其制备方法 |
CN102001682A (zh) * | 2010-12-10 | 2011-04-06 | 黑龙江大学 | 一种微波加热合成杂原子取代MeAPO-31分子筛的方法 |
-
2011
- 2011-12-12 CN CN201110412138.9A patent/CN102513148B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1060650A (zh) * | 1990-10-11 | 1992-04-29 | 陈敏哲 | 联体法生产对(邻)氯苯甲醛、对(邻)氯苯甲酰氯 |
CN101070295A (zh) * | 2007-06-07 | 2007-11-14 | 江苏强盛化工有限公司 | 联产取代苯磺酰氯和取代苯甲酰氯的方法 |
CN101224431A (zh) * | 2008-01-30 | 2008-07-23 | 中国科学院山西煤炭化学研究所 | 甲醇一步法氧化合成甲缩醛的催化剂及其制法和应用 |
CN101898144A (zh) * | 2009-05-27 | 2010-12-01 | 中国石油天然气股份有限公司 | 一种含骨架杂原子的y型分子筛的催化裂化催化剂及其制备方法 |
CN102001682A (zh) * | 2010-12-10 | 2011-04-06 | 黑龙江大学 | 一种微波加热合成杂原子取代MeAPO-31分子筛的方法 |
Non-Patent Citations (4)
Title |
---|
李树安.苯甲醛和酰氯联产最佳反应条件的研究.《淮海工学院学报》.1999,第8卷(第4期),36-38. |
王毅等.由氯化苄制备苯甲醛工艺的研究.《精细与专用化学品》.2004,第12卷(第23期),22-24. |
由氯化苄制备苯甲醛工艺的研究;王毅等;《精细与专用化学品》;20041206;第12卷(第23期);22-24 * |
苯甲醛和酰氯联产最佳反应条件的研究;李树安;《淮海工学院学报》;19991231;第8卷(第4期);36-38 * |
Also Published As
Publication number | Publication date |
---|---|
CN102513148A (zh) | 2012-06-27 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102502687A (zh) | 一种绿色合成钛硅分子筛的方法 | |
CN102513148B (zh) | 一种苄叉二氯酸解反应联产苯甲醛和酰氯的催化剂和工艺 | |
CN102633689A (zh) | 采用亚硫酸铵磺化制备牛磺酸的方法 | |
CN105130805A (zh) | 一种醇醚羧酸盐的制备方法 | |
CN107754854A (zh) | 羟基/磺酸基双官能钒掺杂杂多酸离子杂化体的制备及其应用 | |
CN106883265B (zh) | 一种高效、可循环合成2,4,6-三甲基苯甲酰基-二苯基氧化膦的方法 | |
CN100402485C (zh) | 反应-精馏耦合连续制备乙酸系列酯的方法 | |
CN103864618A (zh) | 1,1-环丙烷二甲酸二甲酯的合成工艺 | |
CN104556116B (zh) | 一种气溶胶辅助合成ts-1分子筛的方法 | |
CN109867695A (zh) | 一种匹伐他汀钙中间体的新制备方法 | |
CN104418763B (zh) | 一种芳基羧酸胺化制备芳基酰胺的方法 | |
CN106831428A (zh) | 一种低温合成苯甲酸苄酯的方法 | |
CN103553076A (zh) | 一种连续式生产sapo-5分子筛的方法 | |
CN104903304B (zh) | 氧化有机羰基化合物的方法 | |
CN104418729A (zh) | 一种可溶柠檬酸盐的制备方法 | |
CN110180524A (zh) | 一种基于硅酸钙基复合催化剂制备碳酸甘油酯的方法 | |
CN107983381A (zh) | 磷酸氧钒催化剂的制备方法及其在催化氧化反应中的应用 | |
CN102584612A (zh) | 肌氨酸的合成方法 | |
CN106187855B (zh) | 一种使用深共晶溶剂制备2-芳基吲哚类化合物的方法 | |
CN108690077A (zh) | 一种中间体左膦右胺盐的合成方法 | |
CN102633594A (zh) | 利用三苯甲基烷基醚合成三苯基氯甲烷的方法 | |
CN108114741A (zh) | 一种制碳酸二甲酯的催化剂及其制备方法和应用 | |
CN102875383A (zh) | 一种尼泊金甲酯的合成方法 | |
CN101230054A (zh) | 一种α-乙酰基-γ-丁内酯的制备方法 | |
CN105330520A (zh) | 一种水相中合成四溴双酚a双(2,3-二溴丙基)醚的方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Owner name: NANTONG TIANSHI CHEMICAL CO., LTD. Free format text: FORMER OWNER: NANJING UNIVERSITY OF TECHNOLOGY Effective date: 20131230 |
|
C41 | Transfer of patent application or patent right or utility model | ||
COR | Change of bibliographic data |
Free format text: CORRECT: ADDRESS; FROM: 210009 NANJING, JIANGSU PROVINCE TO: 226401 NANTONG, JIANGSU PROVINCE |
|
TR01 | Transfer of patent right |
Effective date of registration: 20131230 Address after: 226401 Jiangsu city of Nantong province Rudong County town of Jianshe Road Matang No. 40 Patentee after: NANTONG TIANSHI CHEMICAL Co.,Ltd. Address before: 210009 Nanjing City, Jiangsu Province, the new model road No. 5 Patentee before: Nanjing Tech University |