CA1168262A - Traitement d'esters dibasiques au moyen de borohydrures, de permanganates ou de methylates de metaux alcalins - Google Patents

Traitement d'esters dibasiques au moyen de borohydrures, de permanganates ou de methylates de metaux alcalins

Info

Publication number: CA1168262A
Authority: CA; Canada
Prior art keywords: esters; borohydride; alkali metal; color; permanganate
Prior art date: 1980-07-17
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.): Expired

Application number

CA000381884A

Other languages

English (en)

Inventor

Robert A. Smiley

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.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

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.)

1980-07-17

Filing date

1981-07-16

Publication date

1984-05-29

1980-07-17 Priority claimed from US06/169,734 external-priority patent/US4321407A/en

1980-10-30 Priority claimed from US06/202,250 external-priority patent/US4331812A/en

1981-07-16 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1984-05-29 Application granted granted Critical

1984-05-29 Publication of CA1168262A publication Critical patent/CA1168262A/fr

Status Expired legal-status Critical Current

Links

150000002148 esters Chemical class 0.000 title claims abstract description 67
229910052783 alkali metal Inorganic materials 0.000 title claims abstract description 16
150000001340 alkali metals Chemical class 0.000 title claims abstract description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 30
238000000034 method Methods 0.000 claims abstract description 29
239000002253 acid Substances 0.000 claims abstract description 27
150000007513 acids Chemical class 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 15
239000012279 sodium borohydride Substances 0.000 claims description 12
229910000033 sodium borohydride Inorganic materials 0.000 claims description 11
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 10
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 10
229910017604 nitric acid Inorganic materials 0.000 claims description 10
230000003647 oxidation Effects 0.000 claims description 9
238000007254 oxidation reaction Methods 0.000 claims description 9
239000012286 potassium permanganate Substances 0.000 claims description 8
150000002576 ketones Chemical class 0.000 claims description 6
150000001298 alcohols Chemical class 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 3
229930195733 hydrocarbon Natural products 0.000 claims 1
150000002430 hydrocarbons Chemical class 0.000 claims 1
238000006722 reduction reaction Methods 0.000 description 14
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 9
229920000728 polyester Polymers 0.000 description 8
239000000243 solution Substances 0.000 description 7
238000005809 transesterification reaction Methods 0.000 description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000001361 adipic acid Substances 0.000 description 6
235000011037 adipic acid Nutrition 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
HWJPHQNEWARZLH-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5-decafluoro-6,6-bis(trifluoromethyl)cyclohexane Chemical compound FC(F)(F)C1(C(F)(F)F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F HWJPHQNEWARZLH-UHFFFAOYSA-N 0.000 description 5
238000009835 boiling Methods 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 5
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
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 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000000654 additive Substances 0.000 description 4
-1 aliphatic nitro compounds Chemical class 0.000 description 4
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 4
230000032050 esterification Effects 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 3
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
230000000996 additive effect Effects 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
150000004702 methyl esters Chemical class 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
238000001577 simple distillation Methods 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 description 2
UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 2
239000012448 Lithium borohydride Substances 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
238000013019 agitation Methods 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
239000000920 calcium hydroxide Substances 0.000 description 2
229910001861 calcium hydroxide Inorganic materials 0.000 description 2
238000010531 catalytic reduction reaction Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
ALOUNLDAKADEEB-UHFFFAOYSA-N dimethyl sebacate Chemical compound COC(=O)CCCCCCCCC(=O)OC ALOUNLDAKADEEB-UHFFFAOYSA-N 0.000 description 2
239000012535 impurity Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
150000002828 nitro derivatives Chemical class 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229920001290 polyvinyl ester Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
238000000746 purification Methods 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
230000006641 stabilisation Effects 0.000 description 2
238000011105 stabilization Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
LWBHHRRTOZQPDM-UHFFFAOYSA-N undecanedioic acid Chemical compound OC(=O)CCCCCCCCCC(O)=O LWBHHRRTOZQPDM-UHFFFAOYSA-N 0.000 description 2
RGCVYEOTYJCNOS-UHFFFAOYSA-N (4-cyano-2-methylphenyl)boronic acid Chemical compound CC1=CC(C#N)=CC=C1B(O)O RGCVYEOTYJCNOS-UHFFFAOYSA-N 0.000 description 1
WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
HTXWKZDRDRFVHN-UHFFFAOYSA-N 2-methyloxiran-2-ol Chemical compound CC1(O)CO1 HTXWKZDRDRFVHN-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
PYGXAGIECVVIOZ-UHFFFAOYSA-N Dibutyl decanedioate Chemical compound CCCCOC(=O)CCCCCCCCC(=O)OCCCC PYGXAGIECVVIOZ-UHFFFAOYSA-N 0.000 description 1
MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
DRUKNYVQGHETPO-UHFFFAOYSA-N Nonanedioic acid dimethyl ester Natural products COC(=O)CCCCCCCC(=O)OC DRUKNYVQGHETPO-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000004061 bleaching Methods 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
150000003997 cyclic ketones Chemical class 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
SFVWPXMPRCIVOK-UHFFFAOYSA-N cyclododecanol Chemical compound OC1CCCCCCCCCCC1 SFVWPXMPRCIVOK-UHFFFAOYSA-N 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
IZMOTZDBVPMOFE-UHFFFAOYSA-N dimethyl dodecanedioate Chemical compound COC(=O)CCCCCCCCCCC(=O)OC IZMOTZDBVPMOFE-UHFFFAOYSA-N 0.000 description 1
SHWINQXIGSEZAP-UHFFFAOYSA-N dimethyl heptanedioate Chemical compound COC(=O)CCCCCC(=O)OC SHWINQXIGSEZAP-UHFFFAOYSA-N 0.000 description 1
XTDYIOOONNVFMA-UHFFFAOYSA-N dimethyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC XTDYIOOONNVFMA-UHFFFAOYSA-N 0.000 description 1
229940014772 dimethyl sebacate Drugs 0.000 description 1
LADJFIHHYMBJHB-UHFFFAOYSA-N dimethyl undecanedioate Chemical compound COC(=O)CCCCCCCCCC(=O)OC LADJFIHHYMBJHB-UHFFFAOYSA-N 0.000 description 1
YPLYFEUBZLLLIY-UHFFFAOYSA-N dipropan-2-yl butanedioate Chemical compound CC(C)OC(=O)CCC(=O)OC(C)C YPLYFEUBZLLLIY-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
238000007429 general method Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical class Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
229910002096 lithium permanganate Inorganic materials 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
125000001477 organic nitrogen group Chemical group 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
MTZWHHIREPJPTG-UHFFFAOYSA-N phorone Chemical compound CC(C)=CC(=O)C=C(C)C MTZWHHIREPJPTG-UHFFFAOYSA-N 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
125000004437 phosphorous atom Chemical group 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
239000002966 varnish Substances 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/60—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000381884A 1980-07-17 1981-07-16 Traitement d'esters dibasiques au moyen de borohydrures, de permanganates ou de methylates de metaux alcalins Expired CA1168262A (fr)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US06/169,734 US4321407A (en)	1980-07-17	1980-07-17	Treatment of dibasic esters with alkali metal borohydrides
US169,734		1980-07-17
US20225180A	1980-10-30	1980-10-30
US202,251		1980-10-30
US202,250		1980-10-30
US06/202,250 US4331812A (en)	1980-10-30	1980-10-30	Treatment of dibasic esters with alkali metal methylates

Publications (1)

Publication Number	Publication Date
CA1168262A true CA1168262A (fr)	1984-05-29

Family

ID=27389703

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000381884A Expired CA1168262A (fr)	1980-07-17	1981-07-16	Traitement d'esters dibasiques au moyen de borohydrures, de permanganates ou de methylates de metaux alcalins

Country Status (6)

Country	Link
CA (1)	CA1168262A (fr)
DE (1)	DE3128204A1 (fr)
FR (1)	FR2486935A1 (fr)
GB (1)	GB2079752B (fr)
IT (1)	IT1138090B (fr)
NL (1)	NL8103401A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4766236A (en) *	1987-06-30	1988-08-23	Hoechst Celanese Corporation	Purification of diphenyl phthalates
CN115650399B (zh) *	2022-11-05	2025-04-29	云南大地丰源环保有限公司	一种高锰酸钾废水的处置方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2831883A (en) *	1954-08-18	1958-04-22	Cp Hall Co	Chemical reduction of nitro compounds to purify alpha, omage alkanedioic acid esters
US2957023A (en) *	1957-03-11	1960-10-18	Exxon Research Engineering Co	Treatment of plasticizer esters with alkali metal borohydrides
US3642781A (en) *	1968-10-15	1972-02-15	Warner Lambert Co	Substituted acrylic acids and process for their production
US3991100A (en) *	1974-01-02	1976-11-09	E. I. Du Pont De Nemours And Company	Process for making esters of dibasic acids from acid by-products
DE2420765C3 (de) *	1974-04-29	1981-02-12	Chemische Werke Huels Ag, 4370 Marl	Verfahren zur Reinigung von Decandicarbonsäure- (l,lo)

1981
- 1981-07-16 CA CA000381884A patent/CA1168262A/fr not_active Expired
- 1981-07-16 GB GB8122032A patent/GB2079752B/en not_active Expired
- 1981-07-16 DE DE19813128204 patent/DE3128204A1/de not_active Ceased
- 1981-07-16 IT IT22978/81A patent/IT1138090B/it active
- 1981-07-16 FR FR8113850A patent/FR2486935A1/fr active Granted
- 1981-07-17 NL NL8103401A patent/NL8103401A/nl not_active Application Discontinuation

Also Published As

Publication number	Publication date
FR2486935A1 (fr)	1982-01-22
NL8103401A (nl)	1982-02-16
DE3128204A1 (de)	1982-04-22
GB2079752A (en)	1982-01-27
FR2486935B1 (fr)	1983-12-09
IT8122978A0 (it)	1981-07-16
GB2079752B (en)	1984-07-25
IT1138090B (it)	1986-09-10

Legal Events

Date	Code	Title	Description
2001-05-29	MKEX	Expiry

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US3524892A (en)	1970-08-18	Hexanediol from cyclohexane
US4523027A (en)	1985-06-11	Purification of carboxylates containing aldehydes, acetals and/or unsaturated compounds
CA1168262A (fr)	1984-05-29	Traitement d'esters dibasiques au moyen de borohydrures, de permanganates ou de methylates de metaux alcalins
JP2004528393A (ja)	2004-09-16	水溶液からのギ酸の除去方法
RU2186054C2 (ru)	2002-07-27	Способ получения алифатических дикислот, в частности адипиновой кислоты
US20030050499A1 (en)	2003-03-13	Process for production of high-purity bis-beta-hydroxyethyl terephthalate
US4321407A (en)	1982-03-23	Treatment of dibasic esters with alkali metal borohydrides
US3441604A (en)	1969-04-29	Process for producing dicarboxylic acids
DE69610406T2 (de)	2001-05-03	Verfahren zur bildung zweier terminaler carboxylgruppen ausgehend von ozoniden
US3399035A (en)	1968-08-27	Process for the recovery of boric acid from the oxidation mixtures of liquidphase oxidation of hydrocarbons
JP2500977B2 (ja)	1996-05-29	シクロヘキサノンの製造方法
US4331812A (en)	1982-05-25	Treatment of dibasic esters with alkali metal methylates
JPH0892149A (ja)	1996-04-09	１，３−ジケトンの製造方法，該ケトンを含有する液体安定剤、プラスチック材料およびプラスチック
US2587904A (en)	1952-03-04	Esterification of monohydric ether alcohols
US3439050A (en)	1969-04-15	Color-inhibited alcohol composition for producing plasticizer esters with improved color
GB1596651A (en)	1981-08-26	Process for the recovery of laevulinic acid in the form of its internal ester alphaangelica lactone from mixtures of compounds of similar boiling-point
US3215734A (en)	1965-11-02	Process for purification of terephthalic acid