CN108047089A - 一种4-叔丁基邻苯二甲腈的制备方法 - Google Patents
一种4-叔丁基邻苯二甲腈的制备方法 Download PDFInfo
- Publication number
- CN108047089A CN108047089A CN201711332046.3A CN201711332046A CN108047089A CN 108047089 A CN108047089 A CN 108047089A CN 201711332046 A CN201711332046 A CN 201711332046A CN 108047089 A CN108047089 A CN 108047089A
- Authority
- CN
- China
- Prior art keywords
- butyl
- tert
- reaction
- phthalonitriles
- preparation
- 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.)
- Granted
Links
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 title claims abstract description 82
- 229920006391 phthalonitrile polymer Polymers 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 68
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 28
- YFRGOBSBDSYRNN-UHFFFAOYSA-N 1-butyl-2,3-dimethylbenzene Chemical class CCCCC1=CC=CC(C)=C1C YFRGOBSBDSYRNN-UHFFFAOYSA-N 0.000 claims abstract description 21
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 21
- -1 phthalyl chlorides Chemical class 0.000 claims abstract description 17
- NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical class NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000003022 phthalic acids Chemical class 0.000 claims abstract description 12
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 10
- 239000011630 iodine Substances 0.000 claims abstract description 10
- 239000012286 potassium permanganate Substances 0.000 claims abstract description 10
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims abstract description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 235000011114 ammonium hydroxide Nutrition 0.000 claims abstract description 7
- 239000012024 dehydrating agents Substances 0.000 claims abstract description 7
- 230000003647 oxidation Effects 0.000 claims abstract description 6
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 6
- 230000018044 dehydration Effects 0.000 claims abstract description 4
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 4
- LOTMIRVNJTVTSU-UHFFFAOYSA-N 4-tert-butylbenzene-1,2-dicarbonitrile Chemical compound CC(C)(C)C1=CC=C(C#N)C(C#N)=C1 LOTMIRVNJTVTSU-UHFFFAOYSA-N 0.000 claims abstract description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims abstract description 3
- 230000009471 action Effects 0.000 claims abstract description 3
- 239000002904 solvent Substances 0.000 claims description 18
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 10
- 239000012065 filter cake Substances 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 229960000583 acetic acid Drugs 0.000 claims description 7
- 239000012362 glacial acetic acid Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000012141 concentrate Substances 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000006210 lotion Substances 0.000 claims description 5
- 239000011259 mixed solution Substances 0.000 claims description 5
- 238000004064 recycling Methods 0.000 claims description 5
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 claims description 5
- 235000019345 sodium thiosulphate Nutrition 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- CYMRPDYINXWJFU-UHFFFAOYSA-N 2-carbamoylbenzoic acid Chemical compound NC(=O)C1=CC=CC=C1C(O)=O CYMRPDYINXWJFU-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000003963 dichloro group Chemical group Cl* 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 150000003457 sulfones Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 238000010189 synthetic method Methods 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 2
- 239000012071 phase Substances 0.000 description 7
- 239000007791 liquid phase Substances 0.000 description 6
- 238000012544 monitoring process Methods 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ANGGPYSFTXVERY-UHFFFAOYSA-N 2-iodo-2-methylpropane Chemical compound CC(C)(C)I ANGGPYSFTXVERY-UHFFFAOYSA-N 0.000 description 1
- ZJQUDOMPEQEOSB-UHFFFAOYSA-N 3-butylbenzene-1,2-dicarbonitrile Chemical compound CCCCC1=CC=CC(C#N)=C1C#N ZJQUDOMPEQEOSB-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004176 ammonification Methods 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- CYDRXTMLKJDRQH-UHFFFAOYSA-N benzododecinium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 CYDRXTMLKJDRQH-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/861—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains only halogen as hetero-atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
- C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
-
- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201711332046.3A CN108047089B (zh) | 2017-12-14 | 2017-12-14 | 一种4-叔丁基邻苯二甲腈的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201711332046.3A CN108047089B (zh) | 2017-12-14 | 2017-12-14 | 一种4-叔丁基邻苯二甲腈的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN108047089A true CN108047089A (zh) | 2018-05-18 |
CN108047089B CN108047089B (zh) | 2020-09-11 |
Family
ID=62132625
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201711332046.3A Active CN108047089B (zh) | 2017-12-14 | 2017-12-14 | 一种4-叔丁基邻苯二甲腈的制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN108047089B (zh) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109593051A (zh) * | 2018-12-29 | 2019-04-09 | 江阴苏利化学股份有限公司 | 一种百菌清原料间苯二甲腈的精制方法 |
CN113416150A (zh) * | 2021-08-02 | 2021-09-21 | 上海寻科生物医药科技有限公司 | 一种洛铂中间体的新合成方法 |
CN114230540A (zh) * | 2022-01-06 | 2022-03-25 | 西安爱德克美新材料有限公司 | 一种合成α-BPDA的方法 |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS496301B1 (zh) * | 1969-09-13 | 1974-02-13 | ||
US4551573A (en) * | 1984-10-01 | 1985-11-05 | Phillips Petroleum Company | Alkylation of aromatic compounds |
JPS61287964A (ja) * | 1985-06-14 | 1986-12-18 | Nippon Telegr & Teleph Corp <Ntt> | t−ブチル置換フタロシアニン類及びその中間体の製造方法 |
SU1778107A1 (ru) * | 1990-09-11 | 1992-11-30 | Inst Orch Khim Im N D Zelinsko | Cпocoб пoлучehия 1,2-диmetил-4-tpet-буtилбehзoлa |
US5527769A (en) * | 1993-05-26 | 1996-06-18 | Firmenich Sa | Aromatic compounds and their use in perfumery |
CN1393445A (zh) * | 2001-06-25 | 2003-01-29 | 新力美科技股份有限公司 | 酞花青的微波合成方法 |
CN102005220A (zh) * | 2009-08-31 | 2011-04-06 | 通用电气公司 | 组合物、光学数据存储介质及使用所述光学数据存储介质的方法 |
WO2011105603A1 (ja) * | 2010-02-26 | 2011-09-01 | 株式会社日本触媒 | フタロシアニン誘導体 |
CN103096874A (zh) * | 2010-04-15 | 2013-05-08 | 华盛顿大学 | 前药组合物、前药纳米粒子及其使用方法 |
CN106854165A (zh) * | 2016-12-14 | 2017-06-16 | 贵州大学 | 一种4,6‑双卤代间苯二腈的制备方法 |
-
2017
- 2017-12-14 CN CN201711332046.3A patent/CN108047089B/zh active Active
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS496301B1 (zh) * | 1969-09-13 | 1974-02-13 | ||
US4551573A (en) * | 1984-10-01 | 1985-11-05 | Phillips Petroleum Company | Alkylation of aromatic compounds |
JPS61287964A (ja) * | 1985-06-14 | 1986-12-18 | Nippon Telegr & Teleph Corp <Ntt> | t−ブチル置換フタロシアニン類及びその中間体の製造方法 |
SU1778107A1 (ru) * | 1990-09-11 | 1992-11-30 | Inst Orch Khim Im N D Zelinsko | Cпocoб пoлучehия 1,2-диmetил-4-tpet-буtилбehзoлa |
US5527769A (en) * | 1993-05-26 | 1996-06-18 | Firmenich Sa | Aromatic compounds and their use in perfumery |
CN1393445A (zh) * | 2001-06-25 | 2003-01-29 | 新力美科技股份有限公司 | 酞花青的微波合成方法 |
CN102005220A (zh) * | 2009-08-31 | 2011-04-06 | 通用电气公司 | 组合物、光学数据存储介质及使用所述光学数据存储介质的方法 |
WO2011105603A1 (ja) * | 2010-02-26 | 2011-09-01 | 株式会社日本触媒 | フタロシアニン誘導体 |
CN103096874A (zh) * | 2010-04-15 | 2013-05-08 | 华盛顿大学 | 前药组合物、前药纳米粒子及其使用方法 |
CN106854165A (zh) * | 2016-12-14 | 2017-06-16 | 贵州大学 | 一种4,6‑双卤代间苯二腈的制备方法 |
Non-Patent Citations (8)
Title |
---|
BURBRIDGE, S. J.ETAL: "Nonlinear optical properties of a soluble form of polyisothionaphthene", 《JOURNAL OF MODERN OPTICS》 * |
KHALEZOV, O. I.: "Application of diazotization reaction for synthesis of substituted", 《IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII, KHIMIYA I KHIMICHESKAYA》 * |
MIKI, YASUO ETAL: "Synthesis of alkylbenzenes and determination of their retention indices", 《BUSSHITSU KOGAKU KOGYO GIJUTSU KENKYUSHO HOKOKU 》 * |
POZDNYAKOVICH, YU. V.ETAL: "Chlorination of 4-tert-alkyl-o-xylenes", 《ZHURNAL ORGANICHESKOI KHIMII》 * |
TASHIRO, M.ETAL: "The tert-butylation of aromatic compounds with 2,6-di(tert-butyl)-p-cresol. The selective separation of p-xylene from C8 aromatics", 《ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL》 * |
张英菊等: "4-叔丁基邻苯二甲睛的合成", 《染料工业》 * |
段行信: "《实用精细有机合成手册》", 31 December 2000 * |
王峰等: "Yb(OTf)3催化固体光气对有机酸的酰氯化反应", 《应用化学》 * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109593051A (zh) * | 2018-12-29 | 2019-04-09 | 江阴苏利化学股份有限公司 | 一种百菌清原料间苯二甲腈的精制方法 |
CN109593051B (zh) * | 2018-12-29 | 2021-07-16 | 江阴苏利化学股份有限公司 | 一种百菌清原料间苯二甲腈的精制方法 |
CN113416150A (zh) * | 2021-08-02 | 2021-09-21 | 上海寻科生物医药科技有限公司 | 一种洛铂中间体的新合成方法 |
CN113416150B (zh) * | 2021-08-02 | 2022-05-31 | 上海寻科生物医药科技有限公司 | 一种洛铂中间体的合成方法 |
CN114230540A (zh) * | 2022-01-06 | 2022-03-25 | 西安爱德克美新材料有限公司 | 一种合成α-BPDA的方法 |
Also Published As
Publication number | Publication date |
---|---|
CN108047089B (zh) | 2020-09-11 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Dekamin et al. | Highly efficient and convenient Strecker reaction of carbonyl compounds and amines with TMSCN catalyzed by MCM-41 anchored sulfonic acid as a recoverable catalyst | |
CN108047089A (zh) | 一种4-叔丁基邻苯二甲腈的制备方法 | |
CN111732520B (zh) | 一种3-甲基-2-氨基苯甲酸的制备方法 | |
JPS6034929A (ja) | オレフイン又はビシナルジヒドロキシ化合物を出発物質とするカルボン酸の製造方法 | |
EP1928839B1 (de) | Verfahren zum herstellen von 5-fluor-1,3-dialkyl-1h-pyrazol-4-carbonsäurefluoriden | |
US20200024220A1 (en) | Method for preparing 2-aryl malonamide and applications thereof | |
CN109476588A (zh) | 制备苯基丙二酸二腈的方法 | |
CN104981462B (zh) | 通过介观结构的vpo催化剂氧化醇化合物 | |
CN110950778A (zh) | 制备芳族丙二腈的方法和催化剂体系 | |
CN108689874B (zh) | 一种制备2-芳基丙二酰胺的方法及其应用 | |
CN105753643A (zh) | 一种2,5-二溴碘苯的合成方法 | |
CN105712912A (zh) | 一种三酮类化合物及其中间体的制备方法 | |
CN102875275B (zh) | 一种由芳基卤化物制备芳基腈的方法 | |
CN103980307A (zh) | 2,4,6-三甲基苯甲酰基苯基次膦酸乙酯的制备方法 | |
CN110407676B (zh) | 一种二苯乙二酮类化合物的合成方法及应用 | |
JPS61103867A (ja) | 置換チウラムポリスルフイドの製法 | |
CN103554094B (zh) | 一种制备2,2’-联吡啶-4,4’-(5-己基-2-噻吩)的方法 | |
JPH01238564A (ja) | 芳香族ニトリルの製造方法 | |
JPH02295957A (ja) | ベンゾニトリル類の製造方法 | |
CN101565368A (zh) | 一种制备2,2’-联苯二甲酸的方法 | |
CN109476601A (zh) | 制备卤代吡啶衍生物的方法 | |
Saha | Development of Novel methodologies for the construction of c-hetero bond | |
CN117756603A (zh) | 一种光催化环己烯水合反应制备环己醇的方法 | |
IL24162A (en) | Process and catalyst for the production of aromatic nitriles | |
Degani et al. | Preparation of N, N-dimethyl-N′-arylureas using S, S-dimethyl dithiocarbonate as a carbonylating reagent |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20200703 Address after: 314000 R & D building, No. 321, Jiachuang Road, Xiuzhou District, Jiaxing City, Zhejiang Province Applicant after: Jiaxing Sheng Yuan industrial designs Co.,Ltd. Address before: 450000 Henan Province, Zhengzhou City Red Road No. 56 Applicant before: ZHENGZHOU GECKO SCIENTIFIC Inc. |
|
TA01 | Transfer of patent application right | ||
CB03 | Change of inventor or designer information |
Inventor after: Xiao Xuhui Inventor after: Peng Yong Inventor after: Li Yuan Inventor after: Guo Libing Inventor before: Guo Libing |
|
CB03 | Change of inventor or designer information | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20200818 Address after: Room 501, building A1, Changsha E center, No. 18, Xiangtai Road, Liuyang economic and Technological Development Zone, Liuyang City, Changsha City, Hunan Province Applicant after: Hunan Dao Shi Pharmaceutical Technology Co.,Ltd. Address before: 314000 R & D building, No. 321, Jiachuang Road, Xiuzhou District, Jiaxing City, Zhejiang Province Applicant before: Jiaxing Sheng Yuan industrial designs Co.,Ltd. |
|
TA01 | Transfer of patent application right | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A preparation method of 4-tert-butylphthalonitrile Effective date of registration: 20230410 Granted publication date: 20200911 Pledgee: Jiujiang Bank Co.,Ltd. Huichang Branch Pledgor: Hunan Dao Shi Pharmaceutical Technology Co.,Ltd. Registration number: Y2023980037705 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right |