JPH11140017A - エステルの製造法 - Google Patents

エステルの製造法

Info

Publication number: JPH11140017A
Authority: JP; Japan
Prior art keywords: reaction; catalyst; alcohol; aldehyde; added
Prior art date: 1997-11-12
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.): Pending

Application number

JP9310925A

Other languages

English (en)

Japanese (ja)

Other versions

JPH11140017A5 (de

Inventor

Takashi Sato

孝志佐藤

Toshio Hagiwara

敏男萩原

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

TOKUYAMA SEKIYU KAGAKU KK

Original Assignee

TOKUYAMA SEKIYU KAGAKU KK

Priority date (The priority date 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 date listed.)

1997-11-12

Filing date

1997-11-12

Publication date

1999-05-25

1997-11-12 Application filed by TOKUYAMA SEKIYU KAGAKU KK filed Critical TOKUYAMA SEKIYU KAGAKU KK

1997-11-12 Priority to JP9310925A priority Critical patent/JPH11140017A/ja

1999-05-25 Publication of JPH11140017A publication Critical patent/JPH11140017A/ja

2005-01-06 Publication of JPH11140017A5 publication Critical patent/JPH11140017A5/ja

Status Pending legal-status Critical Current

Links

150000002148 esters Chemical class 0.000 title claims abstract description 23
238000004519 manufacturing process Methods 0.000 title claims description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 70
238000006243 chemical reaction Methods 0.000 claims abstract description 61
239000003054 catalyst Substances 0.000 claims abstract description 46
-1 aluminum alkoxide Chemical class 0.000 claims abstract description 34
229910052782 aluminium Inorganic materials 0.000 claims abstract description 19
239000002841 Lewis acid Substances 0.000 claims abstract description 18
150000007517 lewis acids Chemical class 0.000 claims abstract description 18
238000000034 method Methods 0.000 claims abstract description 11
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims abstract 8
235000019441 ethanol Nutrition 0.000 claims description 40
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 30
239000003426 co-catalyst Substances 0.000 claims description 9
229910052747 lanthanoid Inorganic materials 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
150000002602 lanthanoids Chemical class 0.000 claims description 4
239000000203 mixture Substances 0.000 claims description 4
150000004703 alkoxides Chemical class 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
229910052725 zinc Inorganic materials 0.000 claims description 3
239000011701 zinc Substances 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
150000001721 carbon Chemical group 0.000 claims 1
239000006227 byproduct Substances 0.000 abstract description 10
230000000694 effects Effects 0.000 abstract description 9
230000015572 biosynthetic process Effects 0.000 abstract description 5
238000003786 synthesis reaction Methods 0.000 abstract description 3
230000002194 synthesizing effect Effects 0.000 abstract description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
150000001299 aldehydes Chemical class 0.000 description 23
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 12
230000000052 comparative effect Effects 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000011592 zinc chloride Substances 0.000 description 6
235000005074 zinc chloride Nutrition 0.000 description 6
229910021578 Iron(III) chloride Inorganic materials 0.000 description 5
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 5
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
230000003197 catalytic effect Effects 0.000 description 4
238000000926 separation method Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
238000002156 mixing Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 2
UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 description 2
RXGUIWHIADMCFC-UHFFFAOYSA-N 2-Methylpropyl 2-methylpropionate Chemical compound CC(C)COC(=O)C(C)C RXGUIWHIADMCFC-UHFFFAOYSA-N 0.000 description 2
YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 2
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
XINCECQTMHSORG-UHFFFAOYSA-N Isoamyl isovalerate Chemical compound CC(C)CCOC(=O)CC(C)C XINCECQTMHSORG-UHFFFAOYSA-N 0.000 description 2
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
238000006423 Tishchenko reaction Methods 0.000 description 2
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 2
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
229910052706 scandium Inorganic materials 0.000 description 2
SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
230000006641 stabilisation Effects 0.000 description 2
238000011105 stabilization Methods 0.000 description 2
HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
229910052727 yttrium Inorganic materials 0.000 description 2
VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 2
ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
KEVRVUAKQLMNFS-UHFFFAOYSA-N 2,2-dimethylpropyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)COC(=O)C(C)(C)C KEVRVUAKQLMNFS-UHFFFAOYSA-N 0.000 description 1
XARVANDLQOZMMJ-CHHVJCJISA-N 2-[(z)-[1-(2-amino-1,3-thiazol-4-yl)-2-oxo-2-(2-oxoethylamino)ethylidene]amino]oxy-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)O\N=C(/C(=O)NCC=O)C1=CSC(N)=N1 XARVANDLQOZMMJ-CHHVJCJISA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 1
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000001298 alcohols 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
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
JPUHCPXFQIXLMW-UHFFFAOYSA-N aluminium triethoxide Chemical compound CCO[Al](OCC)OCC JPUHCPXFQIXLMW-UHFFFAOYSA-N 0.000 description 1
229960002903 benzyl benzoate Drugs 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
XWINVLMFYISLRL-UHFFFAOYSA-N cyclohexylmethyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OCC1CCCCC1 XWINVLMFYISLRL-UHFFFAOYSA-N 0.000 description 1
230000009849 deactivation Effects 0.000 description 1
238000010908 decantation Methods 0.000 description 1
SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
229910052733 gallium Inorganic materials 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000000976 ink Substances 0.000 description 1
229940035429 isobutyl alcohol Drugs 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
229940011051 isopropyl acetate Drugs 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 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
JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 1
FGPPDYNPZTUNIU-UHFFFAOYSA-N pentyl pentanoate Chemical compound CCCCCOC(=O)CCCC FGPPDYNPZTUNIU-UHFFFAOYSA-N 0.000 description 1
QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
229940090181 propyl acetate Drugs 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
QPRQEDXDYOZYLA-UHFFFAOYSA-N sec-pentyl alcohol Natural products CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
UBLMWQYLVOVZMT-UHFFFAOYSA-N tert-butyl n-(3-acetylphenyl)carbamate Chemical compound CC(=O)C1=CC=CC(NC(=O)OC(C)(C)C)=C1 UBLMWQYLVOVZMT-UHFFFAOYSA-N 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 1
AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
239000002699 waste material 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)

JP9310925A 1997-11-12 1997-11-12 エステルの製造法 Pending JPH11140017A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP9310925A JPH11140017A (ja)	1997-11-12	1997-11-12	エステルの製造法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP9310925A JPH11140017A (ja)	1997-11-12	1997-11-12	エステルの製造法

Publications (2)

Publication Number	Publication Date
JPH11140017A true JPH11140017A (ja)	1999-05-25
JPH11140017A5 JPH11140017A5 (de)	2005-01-06

Family

ID=18011046

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP9310925A Pending JPH11140017A (ja)	1997-11-12	1997-11-12	エステルの製造法

Country Status (1)

Country	Link
JP (1)	JPH11140017A (de)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2003049855A1 (en) *	2001-12-10	2003-06-19	Showa Denko K.K.	Catalyst for producing carboxylic acid ester and process for producing the same
WO2004047990A1 (ja) *	2002-11-27	2004-06-10	Showa Denko K. K.	カルボン酸エステル製造用触媒および該触媒を使用したカルボン酸エステルの製造方法
CN115745793A (zh) *	2021-09-02	2023-03-07	江苏恒兴新材料科技股份有限公司	异丁醛歧化合成异丁酸异丁酯的方法与催化剂

1997
- 1997-11-12 JP JP9310925A patent/JPH11140017A/ja active Pending

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2003049855A1 (en) *	2001-12-10	2003-06-19	Showa Denko K.K.	Catalyst for producing carboxylic acid ester and process for producing the same
WO2004047990A1 (ja) *	2002-11-27	2004-06-10	Showa Denko K. K.	カルボン酸エステル製造用触媒および該触媒を使用したカルボン酸エステルの製造方法
CN115745793A (zh) *	2021-09-02	2023-03-07	江苏恒兴新材料科技股份有限公司	异丁醛歧化合成异丁酸异丁酯的方法与催化剂

Legal Events

Date	Code	Title	Description
2004-02-12	A521	Written amendment	Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20040210
2004-02-12	A621	Written request for application examination	Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20040210
2006-12-25	A977	Report on retrieval	Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20061225
2007-01-10	A131	Notification of reasons for refusal	Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20070109
2008-03-12	A02	Decision of refusal	Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20080311

Publication	Publication Date	Title
JP3374863B2 (ja)	2003-02-10	ジアルキルカーボネートの製造方法
TW200806622A (en)	2008-02-01	Transesterification process for production of (meth)acrylate ester monomers
US8067633B2 (en)	2011-11-29	Method for the synthesis of (meth)acrylic esters catalysed by a polyol titanate
GB2026478A (en)	1980-02-06	Process for producing alkali metal salts of aryl pyruvic acids
JP2992965B2 (ja)	1999-12-20	エステル交換方法
JPH08269016A (ja)	1996-10-15	アルキルイミダゾリドン（メタ）アクリレートの合成方法
JPH06321909A (ja)	1994-11-22	アルキルイミダゾリドン（メタ）アクリレートの製造方法
JPH11140017A (ja)	1999-05-25	エステルの製造法
EP0144118A1 (de)	1985-06-12	Alkoxycarbonylierung oder Carbonylierung mit Kohlenmonoxid und einer organischen Hydroxylverbindung
JP2002524435A (ja)	2002-08-06	キャロル反応によるγ、δ−不飽和ケトンの製造方法
JP2002241341A (ja)	2002-08-28	高純度（メタ）アクリル酸エステルの製造方法
JPH07330686A (ja)	1995-12-19	ジアルキルカーボネートの製造方法
JP3005684B1 (ja)	2000-01-31	炭酸エステルを製造する方法
JP3062965B2 (ja)	2000-07-12	アリール置換プロピオン酸エステルの調製方法
JPH11140016A (ja)	1999-05-25	エステルの製造方法
JPH07300440A (ja)	1995-11-14	ヘテロ置換アセタールの製造法
US20050080297A1 (en)	2005-04-14	Catalytic system for aldol reactions
GB1583084A (en)	1981-01-21	Hydrocarbonylation of methanol to ethanol in the presence of added compounds
JP5297036B2 (ja)	2013-09-25	２−（１−ヒドロキシアルキル）シクロアルカノンとその脱水体との混合物の製造方法
JP2852418B1 (ja)	1999-02-03	炭酸エステルの製法
JP2003171344A (ja)	2003-06-20	新規なグリオキシル酸組成物およびその製造方法並びにその利用方法
US5463111A (en)	1995-10-31	Process for preparing dialkyl 2-haloethyl malonates
JPH06192178A (ja)	1994-07-12	アリール置換プロピオン酸エステルの製造方法
JPH0761976B2 (ja)	1995-07-05	光学活性アリ−ル酢酸誘導体の製造法
JPH06298716A (ja)	1994-10-25	ウレタノエステルの製造法

JPH11140017A - エステルの製造法 - Google Patents

Info

Links

Classifications

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=18011046

Family Applications (1)

Country Status (1)

Cited By (3)

Cited By (3)

Similar Documents

Legal Events