CA1120949A - Phenol production - Google Patents

Phenol production

Info

Publication number: CA1120949A
Authority: CA; Canada
Prior art keywords: benzoate; benzoic acid; oxide; temperature; heating
Prior art date: 1977-07-22
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

CA000307902A

Other languages

English (en)

French (fr)

Inventor

Placido M. Spaziante

Luigi Giuffre

Giancarlo Sioli

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.)

De Nora SpA

Original Assignee

Oronzio de Nora Impianti Elettrochimici SpA

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.)

1977-07-22

Filing date

1978-07-21

Publication date

1982-03-30

1978-07-21 Application filed by Oronzio de Nora Impianti Elettrochimici SpA filed Critical Oronzio de Nora Impianti Elettrochimici SpA

1982-03-30 Application granted granted Critical

1982-03-30 Publication of CA1120949A publication Critical patent/CA1120949A/en

Status Expired legal-status Critical Current

Links

ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 35
238000004519 manufacturing process Methods 0.000 title claims abstract description 10
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 131
238000000034 method Methods 0.000 claims abstract description 50
239000005711 Benzoic acid Substances 0.000 claims abstract description 40
235000010233 benzoic acid Nutrition 0.000 claims abstract description 40
FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 claims abstract description 38
239000000203 mixture Substances 0.000 claims abstract description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 30
238000010438 heat treatment Methods 0.000 claims abstract description 23
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 22
229910052760 oxygen Inorganic materials 0.000 claims abstract description 22
239000001301 oxygen Substances 0.000 claims abstract description 22
239000010949 copper Substances 0.000 claims abstract description 18
229910052751 metal Inorganic materials 0.000 claims abstract description 15
239000002184 metal Substances 0.000 claims abstract description 15
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 13
229910052802 copper Inorganic materials 0.000 claims abstract description 13
230000015572 biosynthetic process Effects 0.000 claims abstract description 10
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052750 molybdenum Inorganic materials 0.000 claims abstract description 5
239000011733 molybdenum Substances 0.000 claims abstract description 5
230000001590 oxidative effect Effects 0.000 claims abstract description 5
YEOCHZFPBYUXMC-UHFFFAOYSA-L copper benzoate Chemical compound [Cu+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 YEOCHZFPBYUXMC-UHFFFAOYSA-L 0.000 claims description 70
238000006243 chemical reaction Methods 0.000 claims description 26
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 13
229910044991 metal oxide Inorganic materials 0.000 claims description 12
150000004706 metal oxides Chemical class 0.000 claims description 12
238000006114 decarboxylation reaction Methods 0.000 claims description 10
230000007062 hydrolysis Effects 0.000 claims description 8
238000006460 hydrolysis reaction Methods 0.000 claims description 8
239000004215 Carbon black (E152) Substances 0.000 claims description 7
CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical group C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 claims description 7
229960004643 cupric oxide Drugs 0.000 claims description 7
229930195733 hydrocarbon Natural products 0.000 claims description 7
150000002430 hydrocarbons Chemical class 0.000 claims description 7
BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 claims description 5
KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 claims description 5
229940112669 cuprous oxide Drugs 0.000 claims description 5
239000000395 magnesium oxide Substances 0.000 claims description 5
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 5
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical group [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 5
239000007791 liquid phase Substances 0.000 claims description 4
238000010533 azeotropic distillation Methods 0.000 claims description 3
230000003301 hydrolyzing effect Effects 0.000 claims description 3
KOXAXFXITORZGV-UHFFFAOYSA-J molybdenum(4+) tetrabenzoate Chemical compound C(C1=CC=CC=C1)(=O)[O-].[Mo+4].C(C1=CC=CC=C1)(=O)[O-].C(C1=CC=CC=C1)(=O)[O-].C(C1=CC=CC=C1)(=O)[O-] KOXAXFXITORZGV-UHFFFAOYSA-J 0.000 claims description 3
229910000476 molybdenum oxide Inorganic materials 0.000 claims description 2
NSJVJKUPNLTGDG-UHFFFAOYSA-L molybdenum(2+);dibenzoate Chemical compound [Mo+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 NSJVJKUPNLTGDG-UHFFFAOYSA-L 0.000 claims description 2
PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 claims description 2
229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims 4
239000012024 dehydrating agents‎ Substances 0.000 claims 4
229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
-1 alkaline earth metal benzoate Chemical class 0.000 claims 1
230000000911 decarboxylating effect Effects 0.000 claims 1
229940050390 benzoate Drugs 0.000 description 35
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
230000003647 oxidation Effects 0.000 description 9
238000007254 oxidation reaction Methods 0.000 description 9
239000000047 product Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
239000007789 gas Substances 0.000 description 6
150000002500 ions Chemical class 0.000 description 6
PJJZFXPJNUVBMR-UHFFFAOYSA-L magnesium benzoate Chemical compound [Mg+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 PJJZFXPJNUVBMR-UHFFFAOYSA-L 0.000 description 6
239000007787 solid Substances 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
239000000376 reactant Substances 0.000 description 5
239000008096 xylene Substances 0.000 description 5
150000001558 benzoic acid derivatives Chemical class 0.000 description 4
229910002092 carbon dioxide Inorganic materials 0.000 description 4
239000012071 phase Substances 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000011269 tar Substances 0.000 description 4
238000007792 addition Methods 0.000 description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
QSOVSKMNRYAVJR-UHFFFAOYSA-N 2-benzoyloxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1 QSOVSKMNRYAVJR-UHFFFAOYSA-N 0.000 description 2
KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 2
239000005751 Copper oxide Substances 0.000 description 2
VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
229910000431 copper oxide Inorganic materials 0.000 description 2
238000006297 dehydration reaction Methods 0.000 description 2
HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 2
HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 2
239000000725 suspension Substances 0.000 description 2
235000007319 Avena orientalis Nutrition 0.000 description 1
241000209763 Avena sativa Species 0.000 description 1
235000007558 Avena sp Nutrition 0.000 description 1
102100035683 Axin-2 Human genes 0.000 description 1
101700047552 Axin-2 Proteins 0.000 description 1
101100182247 Caenorhabditis elegans lat-1 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 1
239000005750 Copper hydroxide Substances 0.000 description 1
JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 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 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
SBSUGMAHHSEWJB-UHFFFAOYSA-N benzoyl 2-hydroxybenzoate Chemical compound OC1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1 SBSUGMAHHSEWJB-UHFFFAOYSA-N 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
229910001956 copper hydroxide Inorganic materials 0.000 description 1
JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000007792 gaseous phase Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
239000000347 magnesium hydroxide Substances 0.000 description 1
229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
230000036647 reaction Effects 0.000 description 1
238000004064 recycling Methods 0.000 description 1
238000005070 sampling Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/04—Phenol
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
- C07C37/0555—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group being esterified hydroxy groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
- 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

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

CA000307902A 1977-07-22 1978-07-21 Phenol production Expired CA1120949A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH9158/77		1977-07-22
CH915877A CH632478A5 (it)	1977-07-22	1977-07-22	Procedimento per la preparazione del fenolo da acido benzoico.

Publications (1)

Publication Number	Publication Date
CA1120949A true CA1120949A (en)	1982-03-30

Family

ID=4348971

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000307902A Expired CA1120949A (en)	1977-07-22	1978-07-21	Phenol production

Country Status (13)

Country	Link
JP (1)	JPS5439039A (it)
AU (1)	AU528850B2 (it)
BE (1)	BE868779A (it)
CA (1)	CA1120949A (it)
CH (1)	CH632478A5 (it)
DE (1)	DE2832192A1 (it)
ES (1)	ES471940A1 (it)
FR (1)	FR2398043A1 (it)
GB (1)	GB2001317B (it)
IT (1)	IT1097832B (it)
NL (1)	NL7807199A (it)
SE (1)	SE7807919L (it)
ZA (1)	ZA784156B (it)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6187646A (ja) *	1984-10-08	1986-05-06	Sagami Chem Res Center	フッ素置換安息香酸フェニルの製造方法
NL8903098A (nl) *	1989-12-19	1991-07-16	Stamicarbon	Werkwijze voor de bereiding van een fenol.

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2766294A (en) *	1952-05-19	1956-10-09	California Research Corp	Process for preparing monohydroxy aromatic compounds from aromatic carboxylic acids

1977
- 1977-07-22 CH CH915877A patent/CH632478A5/it not_active IP Right Cessation
1978
- 1978-06-27 AU AU37496/78A patent/AU528850B2/en not_active Expired
- 1978-07-03 NL NL7807199A patent/NL7807199A/xx not_active Application Discontinuation
- 1978-07-05 BE BE189106A patent/BE868779A/xx not_active IP Right Cessation
- 1978-07-11 JP JP8361778A patent/JPS5439039A/ja active Pending
- 1978-07-18 SE SE7807919A patent/SE7807919L/xx unknown
- 1978-07-19 IT IT25865/78A patent/IT1097832B/it active
- 1978-07-20 GB GB787830520A patent/GB2001317B/en not_active Expired
- 1978-07-21 ES ES471940A patent/ES471940A1/es not_active Expired
- 1978-07-21 CA CA000307902A patent/CA1120949A/en not_active Expired
- 1978-07-21 DE DE19782832192 patent/DE2832192A1/de not_active Withdrawn
- 1978-07-21 ZA ZA00784156A patent/ZA784156B/xx unknown
- 1978-07-21 FR FR7821790A patent/FR2398043A1/fr active Granted

Also Published As

Publication number	Publication date
AU3749678A (en)	1980-01-03
NL7807199A (nl)	1979-01-24
IT1097832B (it)	1985-08-31
ES471940A1 (es)	1979-10-01
IT7825865A0 (it)	1978-07-19
ZA784156B (en)	1979-07-25
FR2398043A1 (fr)	1979-02-16
CH632478A5 (it)	1982-10-15
FR2398043B1 (it)	1984-07-13
AU528850B2 (en)	1983-05-19
SE7807919L (sv)	1979-01-23
GB2001317B (en)	1982-05-26
DE2832192A1 (de)	1979-02-08
BE868779A (fr)	1978-11-03
GB2001317A (en)	1979-01-31
JPS5439039A (en)	1979-03-24

Legal Events

Date	Code	Title	Description
1999-03-30	MKEX	Expiry

Publication	Publication Date	Title
CA1083600A (en)	1980-08-12	Continuous production of 2-ethyl-hexyl acrylate free from dioctylether
US4205187A (en)	1980-05-27	Process for preparing p,p'-biphenol of high purity
CA1120949A (en)	1982-03-30	Phenol production
US4238627A (en)	1980-12-09	Oxidative process for preparing substituted biphenols
Adam et al.	1977	A Convenient and Efficient Preparation of Aromatic a-Hydroperoxy Acids via Oxygenation of a-Lithio Enolates, Prepared by Direct a-Lithiation of Arylacetic Acids
IE904341A1 (en)	1991-06-05	"Method for removing hydrogen fluoride from mixtures comprising aromatic ketones"
US3399035A (en)	1968-08-27	Process for the recovery of boric acid from the oxidation mixtures of liquidphase oxidation of hydrocarbons
US2800504A (en)	1957-07-23	Production of lower aliphatic acids
JP2537955B2 (ja)	1996-09-25	マレイン酸ジメチルの製造方法
JPH0228587B2 (ja)	1990-06-25	Shibosankuroraidonoseizohoho
JP7694577B2 (ja)	2025-06-18	フルオレノンの製造方法
JPS5819650B2 (ja)	1983-04-19	タ−シヤリ−−アルキル置換されたフエノ−ル類の脱アルキル化法
JPS5844670B2 (ja)	1983-10-04	無水フタル酸の製造方法
US2820821A (en)	1958-01-21	Process for oxidizing glutaraldehydes
US2966513A (en)	1960-12-27	Production of naphthalene dicarboxylic acids
US3760009A (en)	1973-09-18	Hydroquinone process
US5457236A (en)	1995-10-10	Process for the production of beta-diketone
GB1561464A (en)	1980-02-20	Oxidation of alkaryl compounds
US4189602A (en)	1980-02-19	Acid oxidation process
JPS60500091A (ja)	1985-01-24	ジハイドロカルビル　オキサレ−トの製造方法
US3760008A (en)	1973-09-18	Resorcinol process
US3903176A (en)	1975-09-02	Hydroquinone process
KR820002063B1 (ko)	1982-10-26	클로로 안식향산의 제조방법
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US3061651A (en)	1962-10-30	Manufacture of phenols by decarboxylation of salicylic acids