GB1224785A - Removal of acid catalysts from reaction products - Google Patents
Removal of acid catalysts from reaction productsInfo
- Publication number
- GB1224785A GB1224785A GB5440468A GB5440468A GB1224785A GB 1224785 A GB1224785 A GB 1224785A GB 5440468 A GB5440468 A GB 5440468A GB 5440468 A GB5440468 A GB 5440468A GB 1224785 A GB1224785 A GB 1224785A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- reactions
- colophony
- phenol
- cyclization
- Prior art date
- 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
Links
- 239000003377 acid catalyst Substances 0.000 title 1
- 239000007795 chemical reaction product Substances 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 abstract 10
- 239000002253 acid Substances 0.000 abstract 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 150000002989 phenols Chemical class 0.000 abstract 3
- 238000007363 ring formation reaction Methods 0.000 abstract 3
- 235000011149 sulphuric acid Nutrition 0.000 abstract 3
- 239000001117 sulphuric acid Substances 0.000 abstract 3
- 235000007586 terpenes Nutrition 0.000 abstract 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 abstract 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 abstract 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 150000001336 alkenes Chemical class 0.000 abstract 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 abstract 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract 2
- 238000006471 dimerization reaction Methods 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 230000002829 reductive effect Effects 0.000 abstract 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 abstract 2
- -1 terpene compound Chemical class 0.000 abstract 2
- PCNMALATRPXTKX-UHFFFAOYSA-N 1,4-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CCC(C)(O)C=C1 PCNMALATRPXTKX-UHFFFAOYSA-N 0.000 abstract 1
- KPAPHODVWOVUJL-UHFFFAOYSA-N 1-benzofuran;1h-indene Chemical compound C1=CC=C2CC=CC2=C1.C1=CC=C2OC=CC2=C1 KPAPHODVWOVUJL-UHFFFAOYSA-N 0.000 abstract 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 abstract 1
- IULJSGIJJZZUMF-UHFFFAOYSA-N 2-hydroxybenzenesulfonic acid Chemical compound OC1=CC=CC=C1S(O)(=O)=O IULJSGIJJZZUMF-UHFFFAOYSA-N 0.000 abstract 1
- NGFPWHGISWUQOI-UHFFFAOYSA-N 2-sec-butylphenol Chemical compound CCC(C)C1=CC=CC=C1O NGFPWHGISWUQOI-UHFFFAOYSA-N 0.000 abstract 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 abstract 1
- 235000007173 Abies balsamea Nutrition 0.000 abstract 1
- 239000004857 Balsam Substances 0.000 abstract 1
- 239000001293 FEMA 3089 Substances 0.000 abstract 1
- 244000018716 Impatiens biflora Species 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001896 cresols Chemical class 0.000 abstract 1
- 229920001971 elastomer Polymers 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 235000010985 glycerol esters of wood rosin Nutrition 0.000 abstract 1
- NFIDBGJMFKNGGQ-UHFFFAOYSA-N isopropylmethylphenol Natural products CC(C)CC1=CC=CC=C1O NFIDBGJMFKNGGQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 abstract 1
- 229920003052 natural elastomer Polymers 0.000 abstract 1
- 229920001194 natural rubber Polymers 0.000 abstract 1
- 229920003986 novolac Polymers 0.000 abstract 1
- 229920001195 polyisoprene Polymers 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 239000005060 rubber Substances 0.000 abstract 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract 1
- 229920003051 synthetic elastomer Polymers 0.000 abstract 1
- 239000005061 synthetic rubber Substances 0.000 abstract 1
- 150000003505 terpenes Chemical class 0.000 abstract 1
- 239000003039 volatile agent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
- C09F1/02—Purification
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0006—Controlling or regulating processes
- B01J19/002—Avoiding undesirable reactions or side-effects, e.g. avoiding explosions, or improving the yield by suppressing side-reactions
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
- C08G8/10—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenol
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/28—Chemically modified polycondensates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/28—Chemically modified polycondensates
- C08G8/30—Chemically modified polycondensates by unsaturated compounds, e.g. terpenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
- C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1,224,785. Reductive removal of sulphuric acid catalysts; cyclization of rubbers. CHEMISCHE WERKE ALBERT. 15 Nov., 1968 [17 Nov., 1967; 28 March, 1968; 3 Aug., 1968], No. 54404/68. Headings C3E, C3P and C3R. [Also in Division C2] Sulphuric acid and/or acid-reacting derivatives thereof are removed from a mixture by heating the mixture with an "unsaturated terpene compound" to a temperature at which the acid is reduced to volatile products which are expelled from the mixture. The process particularly relates to the removal of sulphuric or sulphonic acids from the products of reactions which they have catalysed, more particularly reactions involving "unsaturated terpene compounds". Such reactions include dimerization of resinic acids or esters, or their reaction with phenols, and the cyclization of natural or synthetic rubber; non-terpene reactions include the acid catalysed alkylation of phenols with olefins, reaction of phenols with aldehydes and ketones, and polymerization of olefins (e.g. in preparing coumarone-indene resins). In the examples (numbers given in parentheses) concentrated sulphuric acid (or o-chlorophenolsulphonic acid (15), phenolsulphonic acid (16, 20), or chlorosulphonic acid (18)) is used to catalyse the reactions of phenol with turpentine oil (1,15), ester gum (3), or colophony and maleic anhydride (4), the cyclization of polyisoprene in phenol (2, 16), the dimerization of colophony (5), the reactions of colophony with cresols (6), o-chlorophenol (7), o-sec-butylphenol (8), 1: 2: 4- xylenol (9), resorcinol (10), alpha-naphthol (11), bisphenol A (12), novolaks (13, 18), anisole (14), or phenol (after heating the colophony alone with H 2 SO 4 ) (17) and the reactions of phenol with isobutyraldehyde (balsam colophony added) (19) and of p-tert.-butylphenol with acrolein (tall colophony added). The reactions are mostly initially exothermic; SO 2 is evolved chiefly at 150-200‹ C., and volatiles are finally removed at 260‹ C. or under vacuum.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1643829 | 1967-11-17 | ||
| DE19681768068 DE1768068C3 (en) | 1967-11-17 | 1968-03-28 | Process for the reductive removal of acidic organic derivatives of sulfuric acid from reaction mixtures with unsaturated terpene compounds |
| DE19681793116 DE1793116C3 (en) | 1968-08-03 | Process for the reductive removal of sulfuric acid or its acidic reacting organic derivatives from reaction mixtures by means of unsaturated terpene compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1224785A true GB1224785A (en) | 1971-03-10 |
Family
ID=27180975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5440468A Expired GB1224785A (en) | 1967-11-17 | 1968-11-15 | Removal of acid catalysts from reaction products |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT298638B (en) |
| BE (1) | BE723747A (en) |
| CH (1) | CH530351A (en) |
| ES (1) | ES360347A1 (en) |
| FR (1) | FR1593635A (en) |
| GB (1) | GB1224785A (en) |
| NL (1) | NL155802B (en) |
| SE (1) | SE344583B (en) |
-
1968
- 1968-11-13 CH CH1695968A patent/CH530351A/en not_active IP Right Cessation
- 1968-11-13 BE BE723747D patent/BE723747A/xx not_active IP Right Cessation
- 1968-11-14 FR FR1593635D patent/FR1593635A/fr not_active Expired
- 1968-11-14 AT AT1108468A patent/AT298638B/en not_active IP Right Cessation
- 1968-11-15 NL NL6816377A patent/NL155802B/en not_active IP Right Cessation
- 1968-11-15 GB GB5440468A patent/GB1224785A/en not_active Expired
- 1968-11-15 SE SE1555868A patent/SE344583B/xx unknown
- 1968-11-16 ES ES360347A patent/ES360347A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT298638B (en) | 1972-05-10 |
| NL155802B (en) | 1978-02-15 |
| FR1593635A (en) | 1970-06-01 |
| BE723747A (en) | 1969-05-13 |
| CH530351A (en) | 1972-11-15 |
| ES360347A1 (en) | 1970-11-01 |
| SE344583B (en) | 1972-04-24 |
| NL6816377A (en) | 1969-05-20 |
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