CN111943838A - 2,4,6-三甲基苯甲酰氯制备方法及酰氯联产技术 - Google Patents
2,4,6-三甲基苯甲酰氯制备方法及酰氯联产技术 Download PDFInfo
- Publication number
- CN111943838A CN111943838A CN201910426810.6A CN201910426810A CN111943838A CN 111943838 A CN111943838 A CN 111943838A CN 201910426810 A CN201910426810 A CN 201910426810A CN 111943838 A CN111943838 A CN 111943838A
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- China
- Prior art keywords
- reaction
- groups
- chloride
- metal
- trimethylbenzene
- Prior art date
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- UKRQMDIFLKHCRO-UHFFFAOYSA-N 2,4,6-trimethylbenzoyl chloride Chemical compound CC1=CC(C)=C(C(Cl)=O)C(C)=C1 UKRQMDIFLKHCRO-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 150000001263 acyl chlorides Chemical class 0.000 title claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- KJYSFXXGQXIPIG-UHFFFAOYSA-N 1,3,5-trimethyl-2-(trichloromethyl)benzene Chemical compound CC1=CC(C)=C(C(Cl)(Cl)Cl)C(C)=C1 KJYSFXXGQXIPIG-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000000654 additive Substances 0.000 claims description 8
- -1 oxides Chemical class 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- FFFIRKXTFQCCKJ-UHFFFAOYSA-N 2,4,6-trimethylbenzoic acid Chemical compound CC1=CC(C)=C(C(O)=O)C(C)=C1 FFFIRKXTFQCCKJ-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 6
- 239000002608 ionic liquid Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002841 Lewis acid Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 5
- 150000007517 lewis acids Chemical class 0.000 claims description 5
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 claims description 4
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002879 Lewis base Substances 0.000 claims description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 150000004703 alkoxides Chemical class 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000007527 lewis bases Chemical class 0.000 claims description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052723 transition metal Inorganic materials 0.000 claims description 4
- 150000003624 transition metals Chemical class 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 150000001649 bromium compounds Chemical class 0.000 claims description 3
- 239000001569 carbon dioxide Substances 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 150000001805 chlorine compounds Chemical class 0.000 claims description 3
- 150000002222 fluorine compounds Chemical class 0.000 claims description 3
- 150000004679 hydroxides Chemical class 0.000 claims description 3
- 150000004694 iodide salts Chemical class 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 150000003568 thioethers Chemical class 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 2
- 239000005995 Aluminium silicate Substances 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- 239000005909 Kieselgur Substances 0.000 claims description 2
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000003172 aldehyde group Chemical group 0.000 claims description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 235000012211 aluminium silicate Nutrition 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 125000005587 carbonate group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 239000007805 chemical reaction reactant Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 2
- 229940117389 dichlorobenzene Drugs 0.000 claims description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 2
- 239000002808 molecular sieve Substances 0.000 claims description 2
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 2
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 2
- VMOWKUTXPNPTEN-UHFFFAOYSA-N n,n-dimethylpropan-2-amine Chemical compound CC(C)N(C)C VMOWKUTXPNPTEN-UHFFFAOYSA-N 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 2
- 150000003460 sulfonic acids Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 229910000299 transition metal carbonate Inorganic materials 0.000 claims description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 2
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 239000010457 zeolite Substances 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 5
- UWCPYKQBIPYOLX-UHFFFAOYSA-N benzene-1,3,5-tricarbonyl chloride Chemical compound ClC(=O)C1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 UWCPYKQBIPYOLX-UHFFFAOYSA-N 0.000 abstract description 3
- 239000012847 fine chemical Substances 0.000 abstract description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000000843 powder Substances 0.000 description 6
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 5
- 238000004321 preservation Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- JPBGQGOQYGYTTA-UHFFFAOYSA-N 1,3,5-trimethylbenzene;hydrochloride Chemical compound Cl.CC1=CC(C)=CC(C)=C1 JPBGQGOQYGYTTA-UHFFFAOYSA-N 0.000 description 2
- MBIZFBDREVRUHY-UHFFFAOYSA-N 2,6-Dimethoxybenzoic acid Chemical compound COC1=CC=CC(OC)=C1C(O)=O MBIZFBDREVRUHY-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 1
- NDXRPDJVAUCBOH-UHFFFAOYSA-N 2,6-dimethoxybenzoyl chloride Chemical compound COC1=CC=CC(OC)=C1C(Cl)=O NDXRPDJVAUCBOH-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
- CXKCZFDUOYMOOP-UHFFFAOYSA-N 3,5-dichlorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC(Cl)=C1 CXKCZFDUOYMOOP-UHFFFAOYSA-N 0.000 description 1
- GGHLXLVPNZMBQR-UHFFFAOYSA-N 3,5-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC(Cl)=CC(Cl)=C1 GGHLXLVPNZMBQR-UHFFFAOYSA-N 0.000 description 1
- BBYDXOIZLAWGSL-UHFFFAOYSA-N 4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C=C1 BBYDXOIZLAWGSL-UHFFFAOYSA-N 0.000 description 1
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 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
- C07C51/58—Preparation of carboxylic acid halides
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Abstract
本发明涉及精细化学品新材料领域,特别涉及2,4,6‑三甲基苯甲酰氯(又称均三苯甲酰氯)及其联产系列酰氯产品的环境友好且经济性制备新工艺技术。
Description
【技术领域】
本发明涉及精细化学品新材料领域,特别涉及2,4,6-三甲基苯甲酰氯(又称均三苯甲酰氯)及其联产系列酰氯产品的环境友好且经济性制备新工艺技术。
【背景技术】
2,4,6-三甲基苯甲酰氯(又称均三苯甲酰氯)是一种重要的新材料精细化学品,作为主要的光引发剂和薄膜材料制造原材料,在业界有广泛的应用。
均三苯甲酰氯的已知产业化制备工艺是例如CN103641706所描述的,C-9 芳烃原料均三甲苯和二氧化碳在路易斯酸和压力作用下先生成均三苯甲酸,均三苯甲酸再和酰氯化试剂例如二氯亚砜或剧毒光气或三光气作用制备均三苯甲酰氯。该工艺是目前行业沿用的传统技术,二氧化硫和/或其他危害性酸气排放当量大,难以环保治理,是当前国家化工行业重点整顿的污染性工艺之一。因此,均三苯甲酰氯的环境友好且经济性制备新工艺技术是业界亟需攻关解决的问题。本发明首次披露均三苯甲酰氯及其系列连带酰氯产品的联产新技术。
【发明内容】
本项申请现已意外地发现,经由下面方程式(I-II)描述的反应技术,使用两种特殊的原材料,即2,4,6-三甲基苯甲酸或1-三氯甲基-2,4,6-三甲基苯 (该物质可以经由本权利人前期披露文献CN102875598报道的方法制备),分别和形式为R-CCl3或R-CO2H的材料在合适的条件conditions下反应,可以非常方便地制备2,4,6-三甲基苯甲酰氯及联产一系列RC(O)Cl酰氯产品,二者可以通过蒸馏或精馏方式分别分离纯化。反应释放的氯化氢气体可以方便地加以吸收和再利用。
这里R是含有6-24个碳原子的芳香基或杂芳香基,该芳香基或杂芳香基可以被1-6个彼此独立的烷基,烷氧基,烷胺基,卤素原子,羧基,酯基,酰胺基,醛基,巯基,磺酸基,碳酸酯基取代;或者,R是含有1-24个碳原子的直链或支链的饱和或不饱和(即含有烯键或炔键)的烷基,该烷基中的任一C- H键或C-C键可以被1-6个彼此独立的非连续性氧原子,氮原子,硫原子,或磷原子插入;或者,该烷基中的任一C-H键氢原子可以被1-6个彼此独立的卤素原子取代。
Conditions是溶剂,温度,压力,和/或添加剂中任意之一或任意二者或二者以上的联合应用。
所述反应“溶剂”选自含有1-24个碳的取代或非取代的芳香烃,直链或支链的脂肪烃,酰胺,醚,酯,酮,腈,羧酸,水,胺,离子液,超临界二氧化碳,或上述任意二者或二者以上类型溶剂组成的混合溶剂;优先的溶剂是二氯甲烷,二氯乙烷,氯仿,四氯化碳,苯,甲苯,二甲苯,三甲苯,四甲苯,乙苯,二乙苯,氯苯,二氯苯,苯甲醚,硝基苯,庚烷,己烷,石油醚,二氧六环,四氢呋喃,甲基叔丁基醚,乙二醇二甲醚,双缩乙二醇二甲醚,三缩乙二醇二甲醚,丙二醇甲醚醋酸酯,三乙胺,三丁胺,二甲基异丙胺,吡啶,N,N- 四甲基乙二胺,N-烷基吗啉,N-烷基吡咯,N,N-二甲基甲酰胺,甲酰吗啉,N, N-二乙基甲酰胺,N-甲基吡咯烷酮,或上述任意二者或二者以上溶剂组成的混合溶剂。所述反应也可以不使用任何溶剂。
所述反应“温度”选自-70摄氏度至250摄氏度之间,优先的是选自-30摄氏度至250摄氏度之间,更优先的是选自-20摄氏度至150摄氏度之间。
所述反应“压力”选自0.001至200个标准大气压之间,优先的是选自0.1 至100个标准大气压之间,更优先的是选自0.1至20个标准大气压之间。
所述反应“添加剂”涵盖反应促进剂,增效剂,催化剂,和/或功能助剂,其是路易斯酸或路易斯碱型(Lewis acids/bases)单质或化合物,优选的是碱金属,碱土金属,主族金属,过渡金属,或上述金属的氟化物,氯化物,溴化物,碘化物,氧化物,氢氧化物,硫化物,烷氧化物,烷基或芳基金属化合物;或碱金属,碱土金属,主族金属,或过渡金属的碳酸盐,碳酸氢盐,亚硫酸盐,硫酸氢盐,磺酸盐,或羧酸盐;或碱金属,碱土金属,或过渡金属的一元或多元有机磷,有机胺,羟基,酮羰基,酯羰基,或羧酸配体的配合物;或四烷基卤化铵,四烷基氢氧化铵,或离子液体(Ionic Liquids);或无机质子酸,有机羧酸,有机磺酸,杂多酸,分子筛,沸石,硅藻土,蒙拓土,高岭土;或硼,硅,磷元素的氟化物,氯化物,溴化物,碘化物,氧化物,氢氧化物,硫化物,烷氧化物;或满足上述定义“添加剂”中任意二者或二者以上的混合物或其联合使用。以反应原材料摩尔当量为基准,所述“添加剂”的使用量可以是催化量,等当量,或过当量。
优选的示例性但非限定性R基团是下述结构:
优选的一种实施方式是,如下式(Ia)所示,由2,4,6-三甲基苯甲酸和1- 三氯甲基-2,4,6-三甲基苯反应,生成单一的2,4,6-三甲基苯甲酰氯产品。
相比于现有技术,本发明所述工艺路线具有突出的环保友好性和优异的成本竞争力优势。在实施例中我们将进一步说明。
【具体实施方式】
下面结合具体实施例进一步说明本发明要旨。
实施例一:
在氮气保护下,将180.6公斤2,4,6-三甲基苯甲酸和274.3公斤1-三氯甲基-2,4,6-三甲基苯以及0.9公斤的无水三氯化铁粉末直接混合,在100-120摄氏度加热反应6-8小时(反应放出盐酸气体)后,体系降温至50摄氏度左右,进行减压蒸馏,得到357.5公斤近无色透明2,4,6-三甲基苯甲酰氯液体产品。
实施例二:
在氮气保护下,将144.5公斤2,4,6-三甲基苯甲酸和172.7公斤的三氯甲基苯以及0.7公斤的三氧化二铁粉末直接混合,逐步升温至100-120摄氏度加热反应过夜(反应放出盐酸气体)后,体系降温至50摄氏度左右,减压除去前馏分后进行精馏,分别得到138.2公斤2,4,6-三甲基苯甲酰氯和97.2公斤苯甲酰氯。
实施例三:
在氮气保护下,将30.9公斤1-三氯甲基-2,4,6-三甲基苯和15.9公斤的苯甲酸以及40克的铁粉直接混合,逐步升温至100-120摄氏度加热反应过夜(反应放出盐酸气体)后,体系降温至50摄氏度左右,减压除去前馏分后进行精馏,分别得到21.8公斤2,4,6-三甲基苯甲酰氯和15.6公斤苯甲酰氯。
实施例四:
在氮气保护下,将196.3公斤1-三氯甲基-2,4,6-三甲基苯和115.7公斤的 4-氟-苯甲酸以及0.25公斤的铁粉直接混合,逐步升温至100-120摄氏度加热反应过夜(反应放出盐酸气体)后,体系降温至50摄氏度左右,减压除去前馏分后进行精馏(管道进行保温),分别得到125.2公斤2,4,6-三甲基苯甲酰氯和 105.2公斤4-氟-苯甲酰氯。
实施例五:
在氮气保护下,将1.9公斤1-三氯甲基-2,4,6-三甲基苯和1.5公斤的2,6- 二甲氧基-苯甲酸以及2.5克的铁粉直接混合,逐步升温至100-120摄氏度加热反应4小时(反应放出盐酸气体)后,体系降温至50摄氏度左右,减压除去前馏分后进行精馏(蒸馏器进行保温),分别得到1.4公斤2,4,6-三甲基苯甲酰氯和1.1公斤2,6-二甲氧基-苯甲酰氯。
实施例六:
在氮气保护下,将2.12公斤1-三氯甲基-2,4,6-三甲基苯和1.64公斤的3, 5-二氯-苯甲酸以及3克的铁粉和3升庚烷直接混合,逐步升温至体系微弱回流反应4小时(反应放出盐酸气体)后,体系降温至50摄氏度左右,减压除去溶剂前馏分后进行精馏(蒸馏器进行保温),分别得到1.31公斤2,4,6-三甲基苯甲酰氯和1.36公斤3,5-二氯-苯甲酰氯。
实施例七:
在氮气保护下,将16.2公斤1-三氯甲基-2,4,6-三甲基苯和6.0公斤的异丁酸以及62克的无水三氯化铁粉末直接混合,逐步升温至100摄氏度左右反应3小时(反应放出盐酸气体)后,体系降温至50摄氏度左右,减压除去前馏分后进行精馏(蒸馏器进行保温),分别得到11.5公斤2,4,6-三甲基苯甲酰氯和6.7公斤异丁酰氯。
实施例八:
在氮气保护下,将19.7公斤1-三氯甲基-2,4,6-三甲基苯和10.6公斤的环己甲酸以及85克的无水三氯化铁粉末直接混合,逐步升温至100摄氏度左右反应4小时(反应放出盐酸气体)后,体系降温至50摄氏度左右,减压除去前馏分后进行精馏(蒸馏器进行保温),分别得到12.6公斤2,4,6-三甲基苯甲酰氯和9.6公斤环己酰氯。
实施例九:
在氮气保护下,将5.2公斤1-三氯甲基-2,4,6-三甲基苯和1.9公斤的甲基丙烯酸以及20克的无水三氯化铁粉末在5升庚烷中直接混合,逐步升温至 100摄氏度左右反应4小时(反应放出盐酸气体)后,体系降温至40摄氏度左右,向液相中加入1200ppm浓度的碘化亚铜阻聚剂,减压除去溶剂前馏分后进行快速分级精馏(蒸馏器进行保温),分别得到2.8公斤2,4,6-三甲基苯甲酰氯和1.2公斤甲基丙烯酰氯。
实施例十:
在氮气保护下,将5.8公斤1-三氯甲基-2,4,6-三甲基苯和1.9公斤的丙烯酸以及23克的无水三氯化铁粉末在10升庚烷中直接混合,逐步升温至 100摄氏度左右反应4小时(反应放出盐酸气体)后,体系降温至40摄氏度左右,向液相中加入1400ppm浓度的碘化亚铜和600ppm的NPAL复合阻聚剂,减压除去溶剂前馏分后进行快速分级精馏(蒸馏器进行保温),分别得到3.2公斤2,4,6-三甲基苯甲酰氯和1.3公斤丙烯酰氯。
需要强调的是,上述实施例仅仅为示例性而非限定性说明,基于本项申请披露,任何从业技术人员所通常可能采用的反应条件或参数等调整或变动均不会偏离本发明的要旨,本专利的保护范围应以相关的权利书记载条目为准。
Claims (7)
1.一种反应方程式(I-II)描述的2,4,6-三甲基苯甲酰氯及系列形式为RC(O)Cl酰氯产品联产工艺技术,其涉及2,4,6-三甲基苯甲酸或1-三氯甲基-2,4,6-三甲基苯分别和形式为R-CCl3或R-CO2H的原料在条件conditions下制备反应:
其中R是含有6-24个碳原子的芳香基或杂芳香基,该芳香基或杂芳香基可以被1-6个彼此独立的烷基,烷氧基,烷胺基,卤素原子,羧基,酯基,酰胺基,醛基,巯基,磺酸基,或碳酸酯基取代;或者,R是含有1-24个碳原子的直链或支链的饱和或不饱和(即含有烯键或炔键)烷基,该烷基的任一C-H键或C-C键可以被1-6个彼此独立的非连续性氧原子,氮原子,硫原子,或磷原子插入;或者,该烷基中的任一C-H键氢原子可以被1-6个彼此独立的卤素原子取代。Conditions是溶剂,温度,压力,和/或添加剂中任意之一或任意二者或二者以上的联合应用。
2.根据权利要求1描述的工艺方法,所述反应“溶剂”选自含有1-24个碳的取代或非取代的芳香烃,直链或支链的脂肪烃,酰胺,醚,酯,酮,腈,羧酸,水,胺,离子液,超临界二氧化碳,或上述任意二者或二者以上类型溶剂组成的混合溶剂;优先的溶剂是二氯甲烷,二氯乙烷,氯仿,四氯化碳,苯,甲苯,二甲苯,三甲苯,四甲苯,乙苯,二乙苯,氯苯,二氯苯,苯甲醚,硝基苯,庚烷,己烷,石油醚,二氧六环,四氢呋喃,甲基叔丁基醚,乙二醇二甲醚,双缩乙二醇二甲醚,三缩乙二醇二甲醚,丙二醇甲醚醋酸酯,三乙胺,三丁胺,二甲基异丙胺,吡啶,N,N-四甲基乙二胺,N-烷基吗啉,N-烷基吡咯,N,N-二甲基甲酰胺,甲酰吗啉,N,N-二乙基甲酰胺,N-甲基吡咯烷酮,或上述任意二者或二者以上溶剂组成的混合溶剂。所述反应也可以优选的不使用任何溶剂。
3.根据权利要求1描述的工艺方法,所述反应“温度”选自-70摄氏度至250摄氏度之间,优先的是选自-30摄氏度至250摄氏度之间,更优先的是选自-20摄氏度至150摄氏度之间。
4.根据权利要求1描述的工艺方法,所述反应“压力”选自0.001至200个标准大气压之间,优先的是选自0.1至100个标准大气压之间,更优先的是选自0.1至20个标准大气压之间。
5.根据权利要求1描述的工艺方法,所述反应“添加剂”涵盖反应促进剂,增效剂,催化剂,和/或功能助剂,其是路易斯酸或路易斯碱型(Lewis acids/bases)单质或化合物,优选的是碱金属,碱土金属,主族金属,过渡金属,或上述金属的氟化物,氯化物,溴化物,碘化物,氧化物,氢氧化物,硫化物,烷氧化物,烷基或芳基金属化合物;或碱金属,碱土金属,主族金属,或过渡金属的碳酸盐,碳酸氢盐,亚硫酸盐,硫酸氢盐,磺酸盐,或羧酸盐;或碱金属,碱土金属,或过渡金属的一元或多元有机磷,有机胺,羟基,酮羰基,酯羰基,或羧酸配体的配合物;或四烷基卤化铵,四烷基氢氧化铵,或离子液体(Ionic Liquids);或无机质子酸,有机羧酸,有机磺酸,杂多酸,分子筛,沸石,硅藻土,蒙拓土,高岭土;或硼,硅,磷元素的氟化物,氯化物,溴化物,碘化物,氧化物,氢氧化物,硫化物,烷氧化物;或满足上述定义“添加剂”中任意二者或二者以上的混合物或其联合使用。以反应原材料摩尔当量为基准,所述“添加剂”的使用量可以是催化量,等当量,或过当量。
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CN106674000A (zh) * | 2015-11-05 | 2017-05-17 | 郑成 | 酰氯联产方法 |
CN109553525A (zh) * | 2017-12-29 | 2019-04-02 | 浙江本立科技股份有限公司 | 一种取代芳烃甲酰氯的合成方法 |
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CN114702380A (zh) * | 2022-04-07 | 2022-07-05 | 河南特格纳特科技有限公司 | 一种联产对氯苯甲酰氯和己酰氯的方法及其酰氯产品 |
CN114702380B (zh) * | 2022-04-07 | 2024-03-19 | 河南特格纳特科技有限公司 | 一种联产对氯苯甲酰氯和己酰氯的方法及其酰氯产品 |
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