CA1049045A - Separation d'un catalyseur a acide inorganique des produits de l'ouverture de l'hydroperoxyde de cumene - Google Patents

Separation d'un catalyseur a acide inorganique des produits de l'ouverture de l'hydroperoxyde de cumene

Info

Publication number: CA1049045A
Authority: CA; Canada
Prior art keywords: alkali metal; zone; inorganic salt; acid; phenate
Prior art date: 1975-03-18
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

CA75222338A

Other languages

English (en)

Other versions

CA222338S (en

Inventor

Maurice D. Cooke

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.)

BP Chemicals Ltd

Original Assignee

BP Chemicals Ltd

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.)

1975-03-18

Filing date

1975-03-18

Publication date

1979-02-20

1975-03-18 Application filed by BP Chemicals Ltd filed Critical BP Chemicals Ltd

1975-03-18 Priority to CA75222338A priority Critical patent/CA1049045A/fr

1979-02-20 Application granted granted Critical

1979-02-20 Publication of CA1049045A publication Critical patent/CA1049045A/fr

Status Expired legal-status Critical Current

Links

229910052500 inorganic mineral Inorganic materials 0.000 title claims abstract description 15
239000011707 mineral Substances 0.000 title claims abstract description 15
238000003776 cleavage reaction Methods 0.000 title claims abstract description 10
230000007017 scission Effects 0.000 title claims abstract description 9
239000003377 acid catalyst Substances 0.000 title claims abstract description 6
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 title claims abstract description 4
239000002253 acid Substances 0.000 claims abstract description 31
229910017053 inorganic salt Inorganic materials 0.000 claims abstract description 13
239000007864 aqueous solution Substances 0.000 claims abstract description 11
150000007513 acids Chemical class 0.000 claims abstract description 7
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical class C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims abstract description 7
MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid group Chemical group C(C(=O)O)(=O)O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims abstract description 7
150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 6
235000006408 oxalic acid Nutrition 0.000 claims abstract description 3
NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 claims abstract description 3
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract 6
239000001569 carbon dioxide Substances 0.000 claims abstract 2
229910002092 carbon dioxide Inorganic materials 0.000 claims abstract 2
238000011065 in-situ storage Methods 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 12
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 10
239000008346 aqueous phase Substances 0.000 claims description 10
229910052783 alkali metal Inorganic materials 0.000 claims description 9
150000001340 alkali metals Chemical class 0.000 claims description 9
150000007524 organic acids Chemical class 0.000 claims description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 8
239000006227 byproduct Substances 0.000 claims description 8
239000012074 organic phase Substances 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 claims description 5
239000004254 Ammonium phosphate Substances 0.000 claims description 5
235000019270 ammonium chloride Nutrition 0.000 claims description 5
235000019289 ammonium phosphates Nutrition 0.000 claims description 5
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 5
229910052921 ammonium sulfate Inorganic materials 0.000 claims description 5
239000001166 ammonium sulphate Substances 0.000 claims description 5
235000011130 ammonium sulphate Nutrition 0.000 claims description 5
238000006386 neutralization reaction Methods 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
229910001514 alkali metal chloride Inorganic materials 0.000 claims description 4
229910000318 alkali metal phosphate Inorganic materials 0.000 claims description 4
229910052936 alkali metal sulfate Inorganic materials 0.000 claims description 4
150000001768 cations Chemical class 0.000 claims description 4
229910052938 sodium sulfate Inorganic materials 0.000 claims description 4
235000011152 sodium sulphate Nutrition 0.000 claims description 4
229910001963 alkali metal nitrate Inorganic materials 0.000 claims description 3
229910000148 ammonium phosphate Inorganic materials 0.000 claims description 3
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 claims description 3
ZRIUUUJAJJNDSS-UHFFFAOYSA-N ammonium phosphates Chemical class [NH4+].[NH4+].[NH4+].[O-]P([O-])([O-])=O ZRIUUUJAJJNDSS-UHFFFAOYSA-N 0.000 claims description 2
235000010755 mineral Nutrition 0.000 claims 4
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 2
150000001450 anions Chemical class 0.000 claims 2
235000002639 sodium chloride Nutrition 0.000 claims 2
239000001103 potassium chloride Substances 0.000 claims 1
235000011164 potassium chloride Nutrition 0.000 claims 1
OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 claims 1
229910052939 potassium sulfate Inorganic materials 0.000 claims 1
239000001120 potassium sulphate Substances 0.000 claims 1
235000011151 potassium sulphates Nutrition 0.000 claims 1
239000011780 sodium chloride Substances 0.000 claims 1
239000000047 product Substances 0.000 abstract description 9
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 abstract description 2
235000015165 citric acid Nutrition 0.000 abstract description 2
229910021653 sulphate ion Inorganic materials 0.000 abstract description 2
229960004424 carbon dioxide Drugs 0.000 abstract 1
239000010410 layer Substances 0.000 abstract 1
239000012044 organic layer Substances 0.000 abstract 1
239000012266 salt solution Substances 0.000 abstract 1
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
241000725101 Clea Species 0.000 description 4
OVSQVDMCBVZWGM-QSOFNFLRSA-N quercetin 3-O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OVSQVDMCBVZWGM-QSOFNFLRSA-N 0.000 description 4
239000000243 solution Substances 0.000 description 4
235000005985 organic acids Nutrition 0.000 description 3
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 2
239000001117 sulphuric acid Substances 0.000 description 2
235000011149 sulphuric acid Nutrition 0.000 description 2
239000011269 tar Substances 0.000 description 2
MBEVSMZJMIQVBG-UHFFFAOYSA-N 2-(hydroxymethyl)guanidine Chemical compound NC(N)=NCO MBEVSMZJMIQVBG-UHFFFAOYSA-N 0.000 description 1
JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
101150052147 ALLC gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
244000205754 Colocasia esculenta Species 0.000 description 1
235000006481 Colocasia esculenta Nutrition 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
239000003513 alkali Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003518 caustics Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
239000000295 fuel oil Substances 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000011273 tar residue Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA75222338A 1975-03-18 1975-03-18 Separation d'un catalyseur a acide inorganique des produits de l'ouverture de l'hydroperoxyde de cumene Expired CA1049045A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA75222338A CA1049045A (fr)	1975-03-18	1975-03-18	Separation d'un catalyseur a acide inorganique des produits de l'ouverture de l'hydroperoxyde de cumene

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA75222338A CA1049045A (fr)	1975-03-18	1975-03-18	Separation d'un catalyseur a acide inorganique des produits de l'ouverture de l'hydroperoxyde de cumene

Publications (1)

Publication Number	Publication Date
CA1049045A true CA1049045A (fr)	1979-02-20

Family

ID=4102563

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA75222338A Expired CA1049045A (fr)	1975-03-18	1975-03-18	Separation d'un catalyseur a acide inorganique des produits de l'ouverture de l'hydroperoxyde de cumene

Country Status (1)

Country	Link
CA (1)	CA1049045A (fr)

1975
- 1975-03-18 CA CA75222338A patent/CA1049045A/fr not_active Expired

Publication	Publication Date	Title
US3931339A (en)	1976-01-06	Removal and neutralisation of acid catalyst from products of cumene hydroperoxide cleavage
KR950017887A (ko)	1995-07-20	알칸온 및/또는 알칸올의 제조방법
CA1142110A (fr)	1983-03-01	Separations des phenols en presence dans des ecoulements a teneur de phenols
CA1049045A (fr)	1979-02-20	Separation d'un catalyseur a acide inorganique des produits de l'ouverture de l'hydroperoxyde de cumene
EP0135295B1 (fr)	1991-07-24	Purification de tertiaire butyl hydroperoxide contenant l'hydroperoxide primaire et secondaire comme impuretés
US5959155A (en)	1999-09-28	Process for the extraction of hydroperoxides
CA1196019A (fr)	1985-10-29	Procede de recuperation de phenols dihydroxyles
JPS5795930A (en)	1982-06-15	Preparation of hydroquinone
US4087469A (en)	1978-05-02	Method of producing 2,2 '-methylenebis(4,6-dialkylphenols)
US4163027A (en)	1979-07-31	Working-up of reaction mixtures containing cyclohexanol and cyclohexanone
US5397482A (en)	1995-03-14	Treatment of cyanides in effluents with Caro's acid
US3810946A (en)	1974-05-14	Purification of phenol
JP3061394B2 (ja)	2000-07-10	クメンハイドロパーオキサイドの製造方法
CA1085879A (fr)	1980-09-16	Separation continue des hydro-carbures qui ne contiennent pas de paraffine de ceux qui en contiennent
US3927124A (en)	1975-12-16	Process for the neutralization of alkyl aromatic hydroperoxide rearrangement reaction products
JPS6038356A (ja)	1985-02-27	パラフインのスルホキシド化の際に得られる反応混合物からパラフイン‐スルホン酸またはパラフイン‐スルホナートを穏やかな条件下で単離する方法
US4080386A (en)	1978-03-21	Production of aralkyl tertiary hydroperoxides
US5439657A (en)	1995-08-08	Molybdenum catalyst separation
AU654597B2 (en)	1994-11-10	Process for working up waste waters comprising rhodium compounds, derivatives or organic phosphines and other impurities in dissolved form
JPH0330584B2 (fr)	1991-04-30
CA1089490A (fr)	1980-11-11	Decomposition du monohydroperoxyde de diethylbenzene pour produire de l'ethylphenol
US1191880A (en)	1916-07-18	Organic chemical process.
JPS6413050A (en)	1989-01-17	Purification of carboxylic acid
JPH0380785B2 (fr)	1991-12-26
JPS6216443A (ja)	1987-01-24	フエノ−ル類の精製法