JPH0193560A - Production of diaryl carbonate - Google Patents
Production of diaryl carbonateInfo
- Publication number
- JPH0193560A JPH0193560A JP62249967A JP24996787A JPH0193560A JP H0193560 A JPH0193560 A JP H0193560A JP 62249967 A JP62249967 A JP 62249967A JP 24996787 A JP24996787 A JP 24996787A JP H0193560 A JPH0193560 A JP H0193560A
- Authority
- JP
- Japan
- Prior art keywords
- lead
- carbonate
- group
- diaryl carbonate
- catalyst
- 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
- -1 diaryl carbonate Chemical compound 0.000 title claims abstract description 39
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 10
- 150000002611 lead compounds Chemical class 0.000 claims abstract description 9
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 230000007935 neutral effect Effects 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000012935 Averaging Methods 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 abstract description 10
- 150000007517 lewis acids Chemical class 0.000 abstract description 10
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract description 6
- 238000005260 corrosion Methods 0.000 abstract description 4
- 230000007797 corrosion Effects 0.000 abstract description 4
- 238000007323 disproportionation reaction Methods 0.000 abstract description 3
- 150000004679 hydroxides Chemical class 0.000 abstract description 3
- 229910000464 lead oxide Inorganic materials 0.000 abstract description 3
- 229910000528 Na alloy Inorganic materials 0.000 abstract description 2
- 229910000978 Pb alloy Inorganic materials 0.000 abstract description 2
- MFEVGQHCNVXMER-UHFFFAOYSA-L 1,3,2$l^{2}-dioxaplumbetan-4-one Chemical compound [Pb+2].[O-]C([O-])=O MFEVGQHCNVXMER-UHFFFAOYSA-L 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- 229910000003 Lead carbonate Inorganic materials 0.000 abstract 1
- WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical compound [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000000047 product Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XTBFPVLHGVYOQH-UHFFFAOYSA-N methyl phenyl carbonate Chemical compound COC(=O)OC1=CC=CC=C1 XTBFPVLHGVYOQH-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229910020282 Pb(OH) Inorganic materials 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 229910052745 lead Inorganic materials 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 102100040996 Cochlin Human genes 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 101000748988 Homo sapiens Cochlin Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910020220 Pb—Sn Inorganic materials 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 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 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 229910052949 galena Inorganic materials 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- XMFOQHDPRMAJNU-UHFFFAOYSA-N lead(II,IV) oxide Inorganic materials O1[Pb]O[Pb]11O[Pb]O1 XMFOQHDPRMAJNU-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N phenyl propionaldehyde Natural products CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】 (産業上の利用分野) 本発明は、ジアリールカーボネートの製造法に関する。[Detailed description of the invention] (Industrial application field) The present invention relates to a method for producing diaryl carbonate.
芒らに詳しくは、アルキルアリールカーボネートの不均
化反応によるジアリールカーボネートの製造法に関する
。Specifically, Ao et al. relates to a method for producing diaryl carbonate by disproportionation reaction of alkylaryl carbonate.
(従来の技術)
アルキルフェニルカーポネートヲ不均化させてジフェニ
ルカーボネートを得ることは既に知られている(%公昭
58−48557号公報)。しかしながら、この方法で
は、ルイス酸およびルイス酸を生成しうる遷移金属化合
物の中から選ばれた触媒を用−てお9.J4体的にはA
DC4,TiX3.UX4゜VOXB 、 VX、 、
ZnX、 、 FeX、 、SnX、 (Xはハロゲン
、アセトキシ基、アルコキシ基、アリーロキシ基)が挙
げられている。このようなルイス酸は、装置の腐食等が
大きく、工業的に実施するには問題があった。(Prior Art) It is already known to obtain diphenyl carbonate by disproportionating alkylphenyl carbonate (% Publication No. 58-48557). However, this method uses a catalyst selected from Lewis acids and transition metal compounds capable of producing Lewis acids. J4 Physically A
DC4, TiX3. UX4゜VOXB, VX, ,
ZnX, , FeX, , SnX, (X is a halogen, an acetoxy group, an alkoxy group, or an aryloxy group) are listed. Such Lewis acids cause serious corrosion of equipment and are problematic for industrial use.
さらに、ルイス酸とプロトン酸との混合物を触媒とする
方法(%開昭60−17!1016号公報)も提案され
ているが、この方法は、ルイス酸に加えてプロトン酸を
使用する友め1g食の問題は。Furthermore, a method using a mixture of a Lewis acid and a protonic acid as a catalyst has also been proposed (%KOKAI Publication No. 1016/1983), but this method uses a protonic acid in addition to a Lewis acid. What is the problem with 1g meals?
よりvl刻になるばかシでなく、触媒の分離1回収が困
難である。Not only does it become more time consuming, but it is also difficult to separate and recover the catalyst.
(発明が解決しようとする問題点)
本発明は、このような従来の方法が有している問題点が
なく、かつ、高収率、高選択率でジアリールカーボネー
トを得る優れ九方法を提供することを目的としてなされ
次ものである。(Problems to be Solved by the Invention) The present invention provides an excellent method for obtaining diaryl carbonate with high yield and high selectivity without the problems of the conventional methods. It was made for the purpose of:
(問題点を解決するための手段)
本発明者らは、このような問題点を解決する之めに鋭意
研究を重ねた結果、優れた触媒を見出し。(Means for Solving the Problems) The present inventors have conducted intensive research to solve these problems, and as a result, have discovered an excellent catalyst.
本発明を完成するに至った。The present invention has now been completed.
すなわち1本発明は、鉛触媒の存在下にアルキルアリー
ルカーボネートをジアリールカーボネートとジアルキル
カーボネートに不均化きせることを特徴とするジアリー
ルカーボネートの製造法を提供するものである。That is, one aspect of the present invention provides a method for producing diaryl carbonate, which comprises disproportionating alkylaryl carbonate into diaryl carbonate and dialkyl carbonate in the presence of a lead catalyst.
本発明の方法は1次のような一般式(I)で表わされる
。The method of the present invention is represented by the following general formula (I).
2R−0−C−0−Ar二Ar−0−C−0−Ar
+R−0−C−0−R・・・・・・CI)(ここで、R
は脂肪族基、指環族基、芳香脂肪族基などのアルキル基
金表わし、 Atは芳香族基であるアリール基を表わす
、)
本発明の原料として用いられるアルキルアリールカーボ
ネートとは、前記(I)式の左辺に示される化合物であ
る。Rとしては1例えば、メチル、エチル、フロビル、
ブチル、ペンチル、ヘキシル。2R-0-C-0-Ar2Ar-0-C-0-Ar
+R-0-C-0-R...CI) (here, R
represents an alkyl group such as an aliphatic group, a ring group, or an aromatic aliphatic group, and At represents an aryl group which is an aromatic group. This is the compound shown on the left side of . R is 1, for example, methyl, ethyl, furovir,
Butyl, pentyl, hexyl.
ヘプチル、オクチル、ノニルなどの各攬異性体を含む脂
肪族基;シクロプロピル、シクロブチル。Aliphatic groups including each isomer such as heptyl, octyl, nonyl; cyclopropyl, cyclobutyl.
シクロペンチル、シクロヘキシル、メチルシクロブチル
、シクロヘキシルメチルなどの脂環族基:ペンジル、7
エネチルなどの芳香脂肪族基などが好ましく、Arとし
ては、フェニル、ナフチル、ピリジルなどの未置換の芳
香族基;次式で表ゎ石れる置換芳香族基
(ここで R/は低級アルΦル基、アルコキシ基。Alicyclic groups such as cyclopentyl, cyclohexyl, methylcyclobutyl, cyclohexylmethyl: penzyl, 7
An aromatic aliphatic group such as enethyl is preferable, and Ar is an unsubstituted aromatic group such as phenyl, naphthyl, pyridyl; a substituted aromatic group represented by the following formula (where R/ is a lower alkyl group, alkoxy group.
アシル基、ハロゲン、アリーロキシ基、芳香族基。Acyl group, halogen, aryloxy group, aromatic group.
ニトロ基、シアノ基、芳香脂肪族基などの置換基を示し
、tは1〜5の整数、mi;i1〜7の整数。It represents a substituent such as a nitro group, a cyano group, an aromatic aliphatic group, t is an integer of 1 to 5, and mi is an integer of i1 to 7.
n#′i1〜4の整数を示し、t、m、nがそれぞれ1
以上の整数の場合は H/は同じものであっても異なっ
たものでめってもよい)などが好ましい。n#'i indicates an integer from 1 to 4, where t, m, and n are each 1
In the case of the above integers, it is preferable that H/ may be the same or different.
ま友、Rにおいて、1個以上の水素がハロゲン。Mayu, in R, one or more hydrogens are halogen.
低級アルコキシ基、シアノ基などの置換基によって置換
されているものも用いることができる。Those substituted with substituents such as lower alkoxy groups and cyano groups can also be used.
特に好ましいアルキルアリールカーボネートとしては、
アルキル基がメチル、エチル、プロピル。Particularly preferred alkylaryl carbonates include:
Alkyl groups are methyl, ethyl, and propyl.
ブチルの炭素数1〜4の低級I脂肪族基の場合であり、
また、アリール基としては、フェニル基ま之は炭素数1
〜9の置換基1例えば、メチル、ジメチル、エチル、t
−ブチル、2−フェニル−2−メチルエチルなどの置換
基を有する炭素数7〜15の置換フェニル基の場合であ
る。In the case of a lower I aliphatic group having 1 to 4 carbon atoms of butyl,
In addition, as an aryl group, a phenyl group has 1 carbon number.
-9 substituents 1 e.g. methyl, dimethyl, ethyl, t
This is the case of a substituted phenyl group having 7 to 15 carbon atoms and having a substituent such as -butyl and 2-phenyl-2-methylethyl.
不発明で用いられる鉛触媒とは、鉛および鉛を含む化合
物であれば、どのようなものでもよいが%に好まし込の
は、塩基性または中性の鉛化合物である。このような鉛
化合物としては1例えば。The lead catalyst used in the invention may be any lead or a compound containing lead, but basic or neutral lead compounds are preferred. One example of such a lead compound is:
pbo 、 pbo、 、 Pb3O4などの酸化鉛類
; PbS 、 Pb、S、 。Lead oxides such as pbo, pbo, , Pb3O4; PbS, Pb, S, .
pbs、などの硫化鉛類; Pb(OH)、 、 Pb
1O,(O)I)、 。Lead sulfides such as pbs; Pb(OH), , Pb
1O, (O)I), .
Pb、(PbO,(OH)! ) 、 Pb、0(OH
)、などの水酸化鉛類;Na1PbO,、に1F’bO
1、NaHPbO,、KHPbOlなどの亜ナマリ酸塩
類、’ Na、PbO,、NatHlPbOa 、に、
pbo、 、KJPb(OH)a)。Pb, (PbO, (OH)! ), Pb, 0(OH
), lead hydroxides; Na1PbO,, 1F'bO
1. Namarites such as NaHPbO, KHPbOl, Na, PbO, NatHlPbOa,
pbo, , KJPb(OH)a).
K4PbO,、Ca、PbO,、CaPbO,などの鉛
酸塩類; PbC0,。K4PbO, Ca, PbO, CaPbO, and other lead salts; PbC0,.
2PbCO,、Pb(OH)、などの鉛の炭酸塩および
その塩基性塩類; Pb(OCOCHI)!、Pb(O
COCHs% 、 Pb(OCOCR,)。2 Lead carbonates and their basic salts such as PbCO, Pb(OH); Pb(OCOCHI)! , Pb(O
COCHs%, Pb(OCOCR,).
・Pb0・3H20などの有機酸の鉛塩およびその炭酸
塩や塩基性塩類; Bu、Pb 、Ph、Pb 、 B
u、PbC4。・Lead salts of organic acids such as Pb0 and 3H20, and their carbonates and basic salts; Bu, Pb, Ph, Pb, B
u, PbC4.
Ph5PbBr 、PhxPb (またはph、Pb、
) 、 Bu、PbOH。Ph5PbBr, PhxPb (or ph, Pb,
), Bu, PbOH.
phtpboなとの有機鉛化合物#A(Buはブチル基
。Organic lead compound #A with phtpbo (Bu is a butyl group.
phはフェニル基を示す) 、” Pb −Na 、P
b −Ca 。ph indicates a phenyl group), "Pb-Na, P
b-Ca.
Pb −Ba 、 Pb −Sn 、 Pb −Sbな
どの鉛の合金類;ホウエン鉱、センアンエン鉱などの鉛
鉱!t2!1類。Lead alloys such as Pb-Ba, Pb-Sn, and Pb-Sb; lead ores such as boenite and sennenite! t2! Type 1.
およびこれらのfヒ合物の水和物などが好ましく用いら
nる。本ちろん、これらの鉛の化合物が反応系中に存在
する有機化合物1例えば、アルキルアリールカーボネー
ト、ジアリールカーボネート。and hydrates of these compounds are preferably used. Of course, these lead compounds are present in the reaction system as organic compounds 1, such as alkylaryl carbonates and diaryl carbonates.
ジアルキルカーボネート、あるいはこれらの化合物の加
水分解生成物(アルコール、芳香族とドロキシ化合物等
)と反応したものであってもよいし。It may be a product reacted with a dialkyl carbonate or a hydrolysis product of these compounds (alcohol, aromatic compound, droxy compound, etc.).
反応に先立って原料や生成物で加熱処理されたもので6
りてもよい。Materials that have been heat-treated with raw materials or products prior to reaction6
You may
これらの中で特に好ましい触媒は、粉末状鉛。Among these, a particularly preferred catalyst is powdered lead.
微粒状ま友は粉末状の鉛−す) IJウム合金、各種酸
化鉛@、水酸化鉛類、炭酸鉛および塩基性炭酸鉛類、亜
ナマリ酸塩類および鉛酸塩類、酢酸鉛および塩基性酢酸
鉛などである。Fine particles are powdered lead) IJium alloys, various lead oxides, lead hydroxides, lead carbonates and basic lead carbonates, namalites and leadates, lead acetate and basic acetic acid. such as lead.
このような鉛まtは鉛化合物から成る触媒は。Such catalysts are made of lead compounds.
1種類でもよいし、281類以上を混合して用いること
もできる。One type may be used, or a mixture of 281 or more types may be used.
ま友、鉛触媒の使用量については特に制限はないが1通
常、アルキルアリールカーボネートに対して0.000
01〜100倍モル、好ましくは0.001〜2倍モル
の範囲で用いられる。Mayu, there is no particular limit on the amount of lead catalyst used, but it is usually 0.000 per alkylaryl carbonate.
It is used in a range of 0.01 to 100 times the mole, preferably 0.001 to 2 times the mole.
本発明の触媒は、高収率、高選択率でジアリールカーボ
ネートを与える優れたものであシ、さらに、これらの鉛
および鉛化合物は、ルイス酸でもないし、ルイス酸を生
成することのできる遷移金属化合物でもないので、ルイ
ス酸の使用によって惹起される装置の腐食等の問題点が
ないことも特徴である。The catalyst of the present invention is excellent in providing diaryl carbonate in high yield and high selectivity.Furthermore, these lead and lead compounds are neither Lewis acids nor transition metals capable of producing Lewis acids. Since it is not a chemical compound, it is also characterized by the fact that there are no problems such as corrosion of equipment caused by the use of Lewis acids.
本発明の反応は、−数式(I) K示されるように平衡
反応であるから、生成物であるジアリールカーボネート
ま友はジアリールカーボネートノ少すくともいずれか一
部を反応系から除去していくことKよって1反応を′よ
シよく進行さぜることかできる。Since the reaction of the present invention is an equilibrium reaction as shown in formula (I), at least part of the diaryl carbonate product is removed from the reaction system. K allows one reaction to proceed much more smoothly.
本発明の反応は1通常、液相または気相で行なわれるの
で、生成物のうちの低沸点成分を留去しながら反応を進
行させることが好ましい。原料および生成物の沸点は1
通常、ジアリールヵーボネー)>1ルキルアリールヵー
ボネ−)>ジアルキルカーボネート、またはジアルキル
カーボネート)アルキルアリールカーボネート〉ジアリ
ールカーボネートであるので、生成物の一部を留去する
ことは容易に行える。アルキル基がメチル、エチル、プ
ロピル、ブチルなどの低級脂肪族基から成るジアルキル
カーボネートは、その沸点が低いので、簡単に反応系か
ら留去することができる。このような意味において、低
級脂肪族基を有するアルキルアリールカーボネートが好
ましく用いられる。Since the reaction of the present invention is usually carried out in a liquid phase or a gas phase, it is preferable to proceed with the reaction while distilling off low-boiling components of the product. The boiling points of raw materials and products are 1
Generally, since diaryl carbonate) > 1 alkylaryl carbonate) > dialkyl carbonate, or dialkyl carbonate) alkylaryl carbonate > diaryl carbonate, a part of the product can be easily distilled off. Dialkyl carbonates whose alkyl groups are lower aliphatic groups such as methyl, ethyl, propyl, and butyl have low boiling points and can be easily distilled off from the reaction system. In this sense, alkylaryl carbonates having lower aliphatic groups are preferably used.
低沸点成分を効果的に留去するために、窒素。Nitrogen to effectively distill off low-boiling components.
アルゴン、ヘリウム、二酸化炭素などの不活性ガスや低
級炭化水素ガスなどを反応系中に導入して。Inert gases such as argon, helium, carbon dioxide, and lower hydrocarbon gases are introduced into the reaction system.
これらのガスに同伴させる方法や、減圧下に行う方法、
およびこれらを併用し九方法などが好ましく用いられる
。また、種型反応器の場合は、気液の界面積を増大させ
fcシ1表面更新を促進させるために、効果的な攪拌を
行うことも好ましい方法であり、基型反応器の場合は気
液界面積の大きな装置にすることも好ましい方法である
。Methods of entraining these gases, methods of performing under reduced pressure,
and nine methods using these in combination are preferably used. In addition, in the case of a seed reactor, it is also a preferable method to carry out effective stirring in order to increase the gas-liquid interface area and promote fc1 surface renewal. It is also a preferable method to use a device with a large liquid interface area.
本発明の反応は1通常、50〜400C,好ましくは8
0〜300Cの範囲で行なわれる。また。The reaction of the present invention is usually carried out at 50 to 400C, preferably at 8C.
It is carried out in the range of 0 to 300C. Also.
反応時間は数分〜数十時間の範囲で行なわれる。The reaction time ranges from several minutes to several tens of hours.
反応圧力も、減圧、常圧、加圧のいずれにおいても実施
される。The reaction pressure may be reduced, normal pressure, or increased pressure.
本発明の方法は、無溶媒でも実施できるし、溶媒を用い
ることもできる。溶媒を用いる場合は。The method of the present invention can be carried out without a solvent or with a solvent. When using a solvent.
低沸点生成物を溶媒の一部と共−去することも好ましい
方法である。このような溶媒としては1例えば、ペンタ
ン、ヘキサン、ヘプタン、オクタン。Co-removal of the low-boiling products with a portion of the solvent is also a preferred method. Examples of such solvents include pentane, hexane, heptane, and octane.
ノナン、デカン、ウンデカン、トリデカン等の脂肪族炭
化水素類;ベンゼン、トルエン、キシレン。Aliphatic hydrocarbons such as nonane, decane, undecane, tridecane; benzene, toluene, xylene.
エチルベンゼン、スチレンなどの芳香原炭fヒ水素類;
シクロヘキサン、メチルシクロヘキサンなどの脂環族炭
化水素類;塩化メタン、塩化メチレン。Aromatic raw carbons such as ethylbenzene and styrene; arsenic;
Alicyclic hydrocarbons such as cyclohexane and methylcyclohexane; methane chloride and methylene chloride.
クロロホルム、四塩化炭素、ジクロルエタン、クロルベ
ンゼン、ジクロルベンゼンなどのハロゲン化炭化水素類
ニアセトニトリル、プロピオニトリル、ベンゾニトリル
などのニトリル類;アセトン。Halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, and dichlorobenzene; Nitriles such as niacetonitrile, propionitrile, and benzonitrile; acetone;
メチルエチルケトン、アセトフェノンなどのケトン類ニ
ジエチルエーテル、テトラヒドロ7ラン。Ketones such as methyl ethyl ketone and acetophenone, diethyl ether, and tetrahydro-7ran.
ジオキサン、ジフェニルエーテルナトのエーテル類など
が好ましく用いられる。Ethers such as dioxane and diphenyl ether are preferably used.
また1本発明の方法は1回分式、連続式、いずれの方法
でも実施できる。Furthermore, the method of the present invention can be carried out in either a single-batch method or a continuous method.
(実施例)
次に1本発明を実施例によって具体的に説明するが1本
発明は、これらの実施例に限定てれるものではない。(Examples) Next, the present invention will be specifically explained with reference to Examples, but the present invention is not limited to these Examples.
実施例1
PbO2r 、メチルフェニルカーボネ−)10rを少
量の窒素気流下で180Cに1時間加熱することによっ
て、触媒の前処理を行った。次いで。Example 1 A catalyst was pretreated by heating 10r of PbO2r, methylphenyl carbonate for 1 hour at 180C under a small stream of nitrogen. Next.
150Cで0.511HHの減圧下に、未反応のメチル
フェニルカーボネートおよび生成し之ジフェニルカーボ
ネートの大部分を留去することによって。By distilling off unreacted methylphenyl carbonate and most of the formed diphenyl carbonate under reduced pressure of 0.511 HH at 150C.
淡黄色固体2.5vを得几。″これにメチルフェニルカ
ーボネー) 76 F (0,5モル)′!!−加え、
全量を攪拌装置、還流冷却器、液面より下部に達するガ
ス導入口、温度計を設けた2 00m14つロフラスコ
に移した。乾燥窒素を80−7分で導入しながら、攪拌
下に195Cの油浴に浸漬することによって反応を行っ
た。還流冷日器のジャケットには90Cの水を流し、副
生ずるメタノールは留去しながう、メチルフェニルカー
ボネートおよび生成するジフェニルカーボネートは、還
流して反応器に戻すようにして反応を行った結果を表1
に示す。Obtained 2.5v of pale yellow solid. ``To this, add methylphenyl carbonate) 76 F (0.5 mol)''!!-
The entire amount was transferred to a 200 m 14 flask equipped with a stirrer, a reflux condenser, a gas inlet reaching below the liquid level, and a thermometer. The reaction was carried out by immersion in a 195 C oil bath with stirring while introducing dry nitrogen at 80-7 minutes. Water at 90C is passed through the jacket of the reflux cooler, and by-product methanol is distilled off. Methylphenyl carbonate and the generated diphenyl carbonate are the result of the reaction by being refluxed and returned to the reactor. Table 1
Shown below.
表 1
実施例2〜11
PbOO代シに株々の鉛化合物または鉛を用いる以外は
、実施例1と同様な方法によって、メチルフェニルカー
ボネート(76r)からジフェニルカーボネートへの反
応を行った。2時間後の反応結果を表2に示す。なお、
これらの実施例において、触媒は5 mmoLまたは鉛
として5〜−atomi用いた。実施例3で用い7tP
b−Na合金は、pb’1?Ofi量チ含むものである
。また、実施例2.3゜7.8および9では、触媒の前
処理を行なわずに直接反応を行った。Table 1 Examples 2 to 11 The reaction from methylphenyl carbonate (76r) to diphenyl carbonate was carried out in the same manner as in Example 1, except that a lead compound or lead was used as the PbOO substitute. The reaction results after 2 hours are shown in Table 2. In addition,
In these examples, the catalyst was used at 5 mmol or 5 to -atomi as lead. 7tP used in Example 3
The b-Na alloy is pb'1? This includes the amount of Ofi. In addition, in Examples 2.3°7.8 and 9, the reaction was carried out directly without pretreatment of the catalyst.
表 2
実施例12〜17
メチルフェニルカーボネートの代シに徨々のアルキルア
リールカーボネートを用いる以外は、実施例1と全く同
様な方法で反応を行い、2時間後の反応結果を表3に示
す。Table 2 Examples 12 to 17 The reaction was carried out in exactly the same manner as in Example 1, except that various alkylaryl carbonates were used in place of methylphenyl carbonate, and the reaction results after 2 hours are shown in Table 3.
表 3
几だし、実施例12および13においては1反応温度は
210Cであり、還流冷却器には130Cの油を循環さ
せた。Table 3 In Examples 12 and 13, the reaction temperature was 210C, and oil at 130C was circulated in the reflux condenser.
(発明の効果) 本発明によれば、鉛触媒を使用することによシ。(Effect of the invention) According to the invention, by using a lead catalyst.
ジアリールカーボネートを高収率、高選択率で製造する
ことができ、また、ルイス酸などの触媒の使用によって
惹起される装置の腐食等の問題が解消され友。Diaryl carbonate can be produced with high yield and high selectivity, and problems such as corrosion of equipment caused by the use of catalysts such as Lewis acids are eliminated.
Claims (4)
をジアリールカーボネートとジアルキルカーボネートに
平均化させることを特徴とするジアリールカーボネート
の製造法。(1) A method for producing diaryl carbonate, which comprises averaging alkylaryl carbonate into diaryl carbonate and dialkyl carbonate in the presence of a lead catalyst.
である特許請求の範囲第1項記載の方法。(2) The method according to claim 1, wherein the lead catalyst is lead and a neutral or basic lead compound.
特許請求の範囲第1項または第2項記載の方法。(3) The method according to claim 1 or 2, wherein the alkyl group is a lower aliphatic group having 1 to 4 carbon atoms.
置換フェニル基である特許請求の範囲第1項ないし第5
項のいずれかに記載の方法。(4) Claims 1 to 5, wherein the aryl group is a phenyl group or a substituted phenyl group having 7 to 15 carbon atoms.
The method described in any of the paragraphs.
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP62249967A JPH0193560A (en) | 1987-10-05 | 1987-10-05 | Production of diaryl carbonate |
CA002013689A CA2013689C (en) | 1987-10-05 | 1990-04-03 | Process for producing diaryl carbonate |
US07/771,538 US5166393A (en) | 1987-10-05 | 1991-10-07 | Process for producing diaryl carbonate |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP62249967A JPH0193560A (en) | 1987-10-05 | 1987-10-05 | Production of diaryl carbonate |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH0193560A true JPH0193560A (en) | 1989-04-12 |
JPH0544938B2 JPH0544938B2 (en) | 1993-07-07 |
Family
ID=17200854
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP62249967A Granted JPH0193560A (en) | 1987-10-05 | 1987-10-05 | Production of diaryl carbonate |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0193560A (en) |
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DE102009053370A1 (en) | 2009-11-14 | 2011-05-19 | Bayer Materialscience Ag | Process for the purification of dialkyl carbonates |
EP2322261A2 (en) | 2009-11-14 | 2011-05-18 | Bayer MaterialScience AG | Method for cleaning dialkyl carbonates |
EP2457891A1 (en) | 2010-10-08 | 2012-05-30 | Bayer MaterialScience AG | Method for manufacturing diaryl carbonates from dialkyl carbonates |
US8304509B2 (en) | 2010-10-08 | 2012-11-06 | Bayer Intellectual Property Gmbh | Process for preparing diaryl carbonates from dialkyl carbonates |
DE102010042937A1 (en) | 2010-10-08 | 2012-04-12 | Bayer Materialscience Aktiengesellschaft | Process for the preparation of diaryl carbonates from dialkyl carbonates |
EP2650278A1 (en) | 2012-04-11 | 2013-10-16 | Bayer MaterialScience AG | Method for manufacturing diaryl carbonates from dialkyl carbonates |
WO2014095776A1 (en) | 2012-12-18 | 2014-06-26 | Bayer Materialscience Ag | Method for producing diaryl carbonate |
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JPH0544938B2 (en) | 1993-07-07 |
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