IL25071A - Preparation of epsilon-hydroxycaproic acid - Google Patents

Preparation of epsilon-hydroxycaproic acid

Info

Publication number: IL25071A
Authority: IL; Israel
Prior art keywords: acid; caprolactone; reaction product; hydroxycaproic acid; reaction
Prior art date: 1965-02-03

Application number

IL2507166A

Other languages

English (en)

Original Assignee

Stamicarbon

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.)

1965-02-03

Filing date

1966-01-30

Publication date

1970-01-29

1966-01-30 Application filed by Stamicarbon filed Critical Stamicarbon

1970-01-29 Publication of IL25071A publication Critical patent/IL25071A/en

Links

238000002360 preparation method Methods 0.000 title description 4
IWHLYPDWHHPVAA-UHFFFAOYSA-N 6-hydroxyhexanoic acid Chemical compound OCCCCCC(O)=O IWHLYPDWHHPVAA-UHFFFAOYSA-N 0.000 title 1
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 18
239000007795 chemical reaction product Substances 0.000 claims description 13
238000006243 chemical reaction Methods 0.000 claims description 6
238000000034 method Methods 0.000 claims description 5
NYHNVHGFPZAZGA-UHFFFAOYSA-N 2-hydroxyhexanoic acid Chemical compound CCCCC(O)C(O)=O NYHNVHGFPZAZGA-UHFFFAOYSA-N 0.000 claims description 2
239000007791 liquid phase Substances 0.000 claims description 2
239000002253 acid Substances 0.000 claims 4
230000001590 oxidative effect Effects 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 18
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 12
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 12
238000007254 oxidation reaction Methods 0.000 description 12
239000000203 mixture Substances 0.000 description 11
239000005711 Benzoic acid Substances 0.000 description 9
235000010233 benzoic acid Nutrition 0.000 description 9
230000003647 oxidation Effects 0.000 description 9
239000000047 product Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
235000011037 adipic acid Nutrition 0.000 description 6
239000001361 adipic acid Substances 0.000 description 6
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 5
239000003054 catalyst Substances 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000004821 distillation Methods 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
238000010992 reflux Methods 0.000 description 3
238000001256 steam distillation Methods 0.000 description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
229910001882 dioxygen Inorganic materials 0.000 description 2
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
150000002596 lactones Chemical class 0.000 description 2
-1 saturated aliphatic aldehyde Chemical class 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
229910052790 beryllium Inorganic materials 0.000 description 1
ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
229940093499 ethyl acetate Drugs 0.000 description 1
235000019439 ethyl acetate Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002505 iron Chemical class 0.000 description 1
239000007788 liquid Substances 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
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
239000000243 solution Substances 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
238000005303 weighing Methods 0.000 description 1
229910052726 zirconium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
- C07C51/445—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation by steam distillation

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Crystallography & Structural Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL2507166A 1965-02-03 1966-01-30 Preparation of epsilon-hydroxycaproic acid IL25071A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
NL6501335A NL6501335A (fi)	1965-02-03	1965-02-03

Publications (1)

Publication Number	Publication Date
IL25071A true IL25071A (en)	1970-01-29

Family

ID=19792264

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL2507166A IL25071A (en)	1965-02-03	1966-01-30	Preparation of epsilon-hydroxycaproic acid

Country Status (9)

Country	Link
AT (1)	AT269096B (fi)
BE (1)	BE675888A (fi)
CH (1)	CH454109A (fi)
DE (1)	DE1593531A1 (fi)
ES (1)	ES322529A1 (fi)
FR (1)	FR1466775A (fi)
GB (1)	GB1124579A (fi)
IL (1)	IL25071A (fi)
NL (1)	NL6501335A (fi)

1965
- 1965-02-03 NL NL6501335A patent/NL6501335A/xx unknown
1966
- 1966-01-30 IL IL2507166A patent/IL25071A/en unknown
- 1966-02-01 GB GB445666A patent/GB1124579A/en not_active Expired
- 1966-02-01 CH CH135366A patent/CH454109A/de unknown
- 1966-02-01 BE BE675888D patent/BE675888A/xx unknown
- 1966-02-01 FR FR47950A patent/FR1466775A/fr not_active Expired
- 1966-02-01 AT AT89566A patent/AT269096B/de active
- 1966-02-02 DE DE19661593531 patent/DE1593531A1/de active Pending
- 1966-02-02 ES ES0322529A patent/ES322529A1/es not_active Expired

Also Published As

Publication number	Publication date
DE1593531A1 (de)	1970-07-16
BE675888A (fi)	1966-08-01
NL6501335A (fi)	1966-08-04
CH454109A (de)	1968-04-15
ES322529A1 (es)	1966-11-16
GB1124579A (en)	1968-08-21
FR1466775A (fr)	1967-01-20
AT269096B (de)	1969-03-10

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US4014755A (en)	1977-03-29	Method of refining pyromellitic acid dianhydride
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US2945058A (en)	1960-07-12	Manufacture of crotonic acid
US3597330A (en)	1971-08-03	Recovery of epsilon-caprolactone and alkane dicarboxylic acid by acid treatment and vacuum distillation
US2413235A (en)	1946-12-24	Crotonic acid manufacture
US5278321A (en)	1994-01-11	Process for simultaneously producing lactone and aromatic carboxylic acid
KR970065502A (ko)	1997-10-13	p-크실렌의 산소-기본 산화 반응에서 물 함량을 최적화시키는 방법
US3088974A (en)	1963-05-07	Exothermic reaction process