NO790098L - Fremgangsmaate for fremstilling av estere - Google Patents

Fremgangsmaate for fremstilling av estere

Info

Publication number: NO790098L
Authority: NO; Norway
Prior art keywords: acid; stated; catalyst; mixture; solvent
Prior art date: 1978-01-16

Application number

NO790098A

Other languages

English (en)

Norwegian (no)

Inventor

Max Gruffaz

Odile Michaelli

Original Assignee

Rhone Poulenc Ind

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.)

1978-01-16

Filing date

1979-01-12

Publication date

1979-07-17

1978-01-16 Priority claimed from FR7801570A external-priority patent/FR2414491A1/fr

1978-11-22 Priority claimed from FR7833770A external-priority patent/FR2442223A2/fr

1979-01-12 Application filed by Rhone Poulenc Ind filed Critical Rhone Poulenc Ind

1979-07-17 Publication of NO790098L publication Critical patent/NO790098L/no

Links

238000000034 method Methods 0.000 title claims description 42
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 60
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 36
239000002904 solvent Substances 0.000 claims description 24
239000003054 catalyst Substances 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 22
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 20
239000005977 Ethylene Substances 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 19
125000004494 ethyl ester group Chemical group 0.000 claims description 14
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 13
150000007513 acids Chemical class 0.000 claims description 12
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 12
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 7
125000005907 alkyl ester group Chemical group 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 6
239000007791 liquid phase Substances 0.000 claims description 6
239000003377 acid catalyst Substances 0.000 claims description 5
230000002378 acidificating effect Effects 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
238000004064 recycling Methods 0.000 claims description 4
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
GAWAYYRQGQZKCR-REOHCLBHSA-N (S)-2-chloropropanoic acid Chemical compound C[C@H](Cl)C(O)=O GAWAYYRQGQZKCR-REOHCLBHSA-N 0.000 claims description 2
HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical compound CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 claims description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 2
239000001361 adipic acid Substances 0.000 claims description 2
235000011037 adipic acid Nutrition 0.000 claims description 2
MIAUJDCQDVWHEV-UHFFFAOYSA-N benzene-1,2-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1S(O)(=O)=O MIAUJDCQDVWHEV-UHFFFAOYSA-N 0.000 claims description 2
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims description 2
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 2
229960005215 dichloroacetic acid Drugs 0.000 claims description 2
WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
235000019260 propionic acid Nutrition 0.000 claims description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 2
239000005711 Benzoic acid Substances 0.000 claims 1
229940092714 benzenesulfonic acid Drugs 0.000 claims 1
235000010233 benzoic acid Nutrition 0.000 claims 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluenecarboxylic acid Natural products CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims 1
LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 claims 1
238000011084 recovery Methods 0.000 claims 1
150000001735 carboxylic acids Chemical class 0.000 description 4
238000004821 distillation Methods 0.000 description 4
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
WKFQMDFSDQFAIC-UHFFFAOYSA-N 2,4-dimethylthiolane 1,1-dioxide Chemical compound CC1CC(C)S(=O)(=O)C1 WKFQMDFSDQFAIC-UHFFFAOYSA-N 0.000 description 2
CMJLMPKFQPJDKP-UHFFFAOYSA-N 3-methylthiolane 1,1-dioxide Chemical compound CC1CCS(=O)(=O)C1 CMJLMPKFQPJDKP-UHFFFAOYSA-N 0.000 description 2
WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
238000011160 research Methods 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
238000003756 stirring Methods 0.000 description 2
RRZIJNVZMJUGTK-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethenoxy)ethene Chemical compound FC(F)=C(F)OC(F)=C(F)F RRZIJNVZMJUGTK-UHFFFAOYSA-N 0.000 description 1
OJNUEXZCVLUSOI-UHFFFAOYSA-N 2,2-dichlorothiolane 1,1-dioxide Chemical compound ClC1(Cl)CCCS1(=O)=O OJNUEXZCVLUSOI-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
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
229920000557 Nafion® Polymers 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000007429 general method Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000003022 phthalic acids Chemical class 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000010517 secondary reaction Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
XPDWGBQVDMORPB-UHFFFAOYSA-N trifluoromethane acid Natural products FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NO790098A 1978-01-16 1979-01-12 Fremgangsmaate for fremstilling av estere NO790098L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7801570A FR2414491A1 (fr)	1978-01-16	1978-01-16	Procede pour la preparation d'esters
FR7833770A FR2442223A2 (fr)	1978-11-22	1978-11-22	Procede pour la preparation d'esters

Publications (1)

Publication Number	Publication Date
NO790098L true NO790098L (no)	1979-07-17

Family

ID=26220407

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO790098A NO790098L (no)	1978-01-16	1979-01-12	Fremgangsmaate for fremstilling av estere

Country Status (9)

Country	Link
US (1)	US4281176A (es)
EP (1)	EP0003205B1 (es)
BR (1)	BR7900230A (es)
CA (1)	CA1128955A (es)
DE (1)	DE2960203D1 (es)
DK (1)	DK18779A (es)
ES (1)	ES476885A1 (es)
NO (1)	NO790098L (es)
YU (1)	YU6779A (es)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4980501A (en) *	1984-07-27	1990-12-25	National Distillers And Chemical Corporation	Production of secondary-butyl fluoroester and secondary-butyl alcohol obtained therefrom
DE3913781A1 (de) *	1989-04-26	1990-10-31	Hoechst Ag	Verfahren zur herstellung von nitro-benzoesaeure-alkylestern
US5241106A (en) *	1991-10-22	1993-08-31	Mitsui Toatsu Chemicals, Inc.	Process for producing ethyl acetate
US20080021235A1 (en) *	2006-07-18	2008-01-24	Lebedev Mikhail Y	Process for making tricyclodecenyl esters
US9328054B1 (en)	2013-09-27	2016-05-03	Travis Danner	Method of alcoholisis of fatty acids and fatty acid gyicerides

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA447461A (en) *		1948-03-23	A. Bruson Herman	Ester of hydroxydihydronorpolycyclopentadiene
US2006734A (en) *	1933-09-02	1935-07-02	Shell Dev	Production of esterified olefines
US2224809A (en) *	1935-10-21	1940-12-10	Dow Chemical Co	Method of making isopropyl esters of aliphatic acids
US2551643A (en) *	1949-01-25	1951-05-08	Socony Vacuum Oil Co Inc	Synthetic lubricants from alphamonoolefins and unsaturated esters and method for producing the same
US3474131A (en) *	1966-10-31	1969-10-21	Universal Oil Prod Co	Preparation of primary alkyl esters
US3907873A (en) *	1970-05-14	1975-09-23	Int Flavors & Fragrances Inc	Novel fragrance materials and process
US4048220A (en) *	1975-05-30	1977-09-13	Scm Corporation	Process for preparation of 1,4-haloallylic esters from dienes

1979
- 1979-01-10 EP EP79420001A patent/EP0003205B1/fr not_active Expired
- 1979-01-10 DE DE7979420001T patent/DE2960203D1/de not_active Expired
- 1979-01-12 NO NO790098A patent/NO790098L/no unknown
- 1979-01-15 BR BR7900230A patent/BR7900230A/pt unknown
- 1979-01-15 YU YU00067/79A patent/YU6779A/xx unknown
- 1979-01-15 CA CA319,669A patent/CA1128955A/fr not_active Expired
- 1979-01-16 US US06/003,814 patent/US4281176A/en not_active Expired - Lifetime
- 1979-01-16 ES ES476885A patent/ES476885A1/es not_active Expired
- 1979-01-16 DK DK18779A patent/DK18779A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
EP0003205A1 (fr)	1979-07-25
YU6779A (en)	1982-10-31
EP0003205B1 (fr)	1981-03-25
ES476885A1 (es)	1979-05-16
BR7900230A (pt)	1979-08-14
US4281176A (en)	1981-07-28
DE2960203D1 (en)	1981-04-16
CA1128955A (fr)	1982-08-03
DK18779A (da)	1979-07-17

Publication	Publication Date	Title
CA1212122A (en)	1986-09-30	Alkanoyloxybenzenesulfonate salt production
US3590073A (en)	1971-06-29	Esterification of tertiary alcohols
NO790098L (no)	1979-07-17	Fremgangsmaate for fremstilling av estere
US2460233A (en)	1949-01-25	Esters of sulfolene halohydrins
CH627432A5 (en)	1982-01-15	Process for the preparation of vinylcyclopropanecarboxylates
JP2001508076A (ja)	2001-06-19	（メタ）アクリル酸とアルカノールとのエステル化方法
Mohacsi	1982	A convenient preparation of methyl esters from carboxylic acids
CA1328886C (en)	1994-04-26	Process for the preparation of carboxylic acid methyl esters
EP0553668B1 (en)	1997-04-16	Process for making arylacrylic acids and their esters
US5100588A (en)	1992-03-31	Process for the preparation of acyloxybenzenesulfonic acids and their salts
US5994578A (en)	1999-11-30	Ester preparation
US4210611A (en)	1980-07-01	Halogenated hydrocarbons, useful as insecticide intermediates, and methods for their preparation
NO790099L (no)	1979-07-17	Fremgangsmaate for fremstilling av estere
US5914426A (en)	1999-06-22	Process for the preparation of di-tert-butyl succinate
DE10015659A1 (de)	2001-10-04	Verfahren zur Herstellung von Carbonsäurebenzylestern
EP0978503B1 (de)	2003-05-07	Synthese von o-(p-Tolyl)benzoesäure-tert.-butylester durch Umsetzung von o-(p-Tolyl)benzoesäure mit Isobutylen unter Säurekatalyse
US3278589A (en)	1966-10-11	Preparation of esters of terpene alco- hols and their homologues
GB2033391A (en)	1980-05-21	Process for Synthesis of Keto Acids or Esters
US5750771A (en)	1998-05-12	Process for the manufacture of sec-butyl acrylate by reaction of acrylic acid and butene isomers
US4182901A (en)	1980-01-08	Diacyloxybutene isomerization with selenium dioxide
US4665221A (en)	1987-05-12	Preparation of terpenoid formates
JPS5822094B2 (ja)	1983-05-06	エチルエステル類の製造方法
US4845270A (en)	1989-07-04	Propanone 1,3-disulfonic acid as an esterification catalyst
US4238356A (en)	1980-12-09	Diacyloxybutene isomerization catalysts comprising selenium dioxide and carboxylic acid
SU809805A1 (ru)	1982-02-07	Способ получени алифатических альдегидов и карбоновых кислот