diff --git a/datafusion/optimizer/src/simplify_expressions/expr_simplifier.rs b/datafusion/optimizer/src/simplify_expressions/expr_simplifier.rs
index 39c8541b51b2f..32b51a2fc7756 100644
--- a/datafusion/optimizer/src/simplify_expressions/expr_simplifier.rs
+++ b/datafusion/optimizer/src/simplify_expressions/expr_simplifier.rs
@@ -39,12 +39,12 @@ use datafusion_common::{
     metadata::FieldMetadata,
     tree_node::{Transformed, TransformedResult, TreeNode, TreeNodeRewriter},
 };
-use datafusion_expr::expr::HigherOrderFunction;
 use datafusion_expr::{
     BinaryExpr, Case, ColumnarValue, Expr, ExprSchemable, Like, Operator, Volatility,
     and, binary::BinaryTypeCoercer, lit, or, preimage::PreimageResult,
 };
 use datafusion_expr::{Cast, TryCast, simplify::ExprSimplifyResult};
+use datafusion_expr::{binary_expr, expr::HigherOrderFunction};
 use datafusion_expr::{expr::ScalarFunction, interval_arithmetic::NullableInterval};
 use datafusion_expr::{
     expr::{InList, InSubquery},
@@ -1095,6 +1095,11 @@ impl TreeNodeRewriter for Simplifier<'_> {
                 Transformed::yes(*right)
             }
 
+            // (A + 1) + 2 -> A + (1 + 2)
+            expr if is_associative_with_adjacent_literals(&expr, self.info) => {
+                Transformed::yes(reassociate_literals(expr, self.info))
+            }
+
             //
             // Rules for Multiply
             //
@@ -2355,6 +2360,60 @@ fn simplify_right_is_one_case(
     }
 }
 
+fn reassociate_literals(expr: Expr, info: &SimplifyContext) -> Expr {
+    fn flatten(
+        op: Operator,
+        datatype: &DataType,
+        info: &SimplifyContext,
+        expr: Expr,
+        out: &mut Vec<Expr>,
+    ) {
+        match &expr {
+            Expr::BinaryExpr(binary)
+                if binary.op == op
+                    && matches!(info.get_data_type(&expr), Ok(dt) if &dt == datatype) =>
+            {
+                let Expr::BinaryExpr(binary) = expr else {
+                    unreachable!()
+                };
+                flatten(op, datatype, info, *binary.left, out);
+                flatten(op, datatype, info, *binary.right, out);
+            }
+            _ => out.push(expr),
+        }
+    }
+
+    let (op, datatype) = match (&expr, info.get_data_type(&expr)) {
+        (Expr::BinaryExpr(expr), Ok(datatype)) => (expr.op, datatype),
+        _ => return expr,
+    };
+    let mut exprs = Vec::new();
+    flatten(op, &datatype, info, expr, &mut exprs);
+    let mut exprs = exprs.into_iter();
+
+    let mut out = exprs.next().unwrap();
+    let mut lit = None;
+    for expr in exprs {
+        if is_lit(&expr) {
+            if let Some(left) = lit {
+                lit = Some(binary_expr(left, op, expr));
+            } else {
+                lit = Some(expr);
+            }
+        } else {
+            if let Some(lit) = lit.take() {
+                out = binary_expr(out, op, lit);
+            }
+            out = binary_expr(out, op, expr);
+        }
+    }
+    if let Some(lit) = lit.take() {
+        binary_expr(out, op, lit)
+    } else {
+        out
+    }
+}
+
 #[cfg(test)]
 mod tests {
     use super::*;
@@ -3368,6 +3427,60 @@ mod tests {
         assert_eq!(simplify(expr_eq), lit(true));
     }
 
+    #[test]
+    fn test_simplify_nested_literals_associative() {
+        assert_change(
+            col("c3") + lit(1i64) + lit(2i64) + lit(3i64) + col("c3_non_null"),
+            col("c3") + lit(6i64) + col("c3_non_null"),
+        );
+        assert_change(
+            (col("c3") + lit(1i64)) + (lit(2i64) + col("c3_non_null")),
+            col("c3") + lit(3i64) + col("c3_non_null"),
+        );
+        assert_change(lit(1i64) + lit(2i64) + col("c3"), lit(3i64) + col("c3"));
+        assert_change(col("c4") + lit(1u32) + lit(2u32), col("c4") + lit(3u32));
+        assert_change(
+            col("c3") + lit(1i64) + col("c3_non_null") + lit(2i64) + lit(3i64),
+            col("c3") + lit(1i64) + col("c3_non_null") + lit(5i64),
+        );
+        assert_change(
+            col("c3") * col("c3") + lit(2i64) + (lit(3i64) + lit(4i64) * col("c3")),
+            col("c3") * col("c3") + lit(5i64) + lit(4i64) * col("c3"),
+        );
+        assert_change(col("c3") * lit(2i64) * lit(3i64), col("c3") * lit(6i64));
+        assert_change(
+            (col("c3") * lit(2i64)) * (lit(3i64) * col("c3_non_null")),
+            col("c3") * lit(6i64) * col("c3_non_null"),
+        );
+
+        let cat = |left, right| binary_expr(left, Operator::StringConcat, right);
+        assert_change(
+            cat(cat(cat(col("c1"), lit("a")), lit("b")), col("c1")),
+            cat(cat(col("c1"), lit("ab")), col("c1")),
+        );
+
+        assert_change(col("c3") & lit(12i64) & lit(10i64), col("c3") & lit(8i64));
+        assert_change(
+            (col("c4") & lit(12u32)) & (lit(10u32) & col("c4_non_null")),
+            col("c4") & lit(8u32) & col("c4_non_null"),
+        );
+
+        assert_change(col("c3") | lit(1i64) | lit(2i64), col("c3") | lit(3i64));
+        assert_change(col("c4") ^ lit(1u32) ^ lit(3u32), col("c4") ^ lit(2u32));
+
+        assert_no_change(col("c3") + lit(1i64));
+        assert_no_change(lit(1i64) + col("c3"));
+        assert_no_change(col("c6") + lit(1.0) + lit(2.0));
+        assert_no_change(col("c6") * lit(3.0) * lit(4.0));
+        assert_no_change(col("c4") + lit(5u32) + lit(6u8));
+        assert_no_change(lit(7i64) + col("c3") + lit(8i64));
+
+        assert_change(
+            col("c4") + lit(1u32) + lit(2i64) + lit(3i64),
+            col("c4") + lit(1u32) + lit(5i64),
+        );
+    }
+
     #[test]
     fn test_simplify_regex() {
         // malformed regex
@@ -3685,6 +3798,7 @@ mod tests {
                         Field::new("c3_non_null", DataType::Int64, false),
                         Field::new("c4_non_null", DataType::UInt32, false),
                         Field::new("c5", DataType::FixedSizeBinary(3), true),
+                        Field::new("c6", DataType::Float64, true),
                     ]
                     .into(),
                     HashMap::new(),
diff --git a/datafusion/optimizer/src/simplify_expressions/utils.rs b/datafusion/optimizer/src/simplify_expressions/utils.rs
index b0908b47602f7..65a9d06c40ee2 100644
--- a/datafusion/optimizer/src/simplify_expressions/utils.rs
+++ b/datafusion/optimizer/src/simplify_expressions/utils.rs
@@ -17,12 +17,16 @@
 
 //! Utility functions for expression simplification
 
-use arrow::datatypes::i256;
-use datafusion_common::{Result, ScalarValue, internal_err};
+use arrow::datatypes::{DataType, i256};
+use datafusion_common::{
+    Result, ScalarValue, internal_err,
+    tree_node::{TreeNode, TreeNodeRecursion, TreeNodeVisitor},
+};
 use datafusion_expr::{
     Case, Expr, Like, Operator,
     expr::{Between, BinaryExpr, InList},
     expr_fn::{and, bitwise_and, bitwise_or, or},
+    simplify::SimplifyContext,
 };
 
 pub static POWS_OF_TEN: [i128; 38] = [
@@ -290,6 +294,77 @@ pub fn is_lit(expr: &Expr) -> bool {
     matches!(expr, Expr::Literal(_, _))
 }
 
+pub fn is_associative(op: Operator, datatype: &DataType) -> bool {
+    match op {
+        Operator::Plus | Operator::Multiply => datatype.is_integer(),
+        Operator::StringConcat
+        | Operator::BitwiseAnd
+        | Operator::BitwiseOr
+        | Operator::BitwiseXor => true,
+        _ => false,
+    }
+}
+
+pub fn is_associative_with_adjacent_literals(
+    expr: &Expr,
+    info: &SimplifyContext,
+) -> bool {
+    struct AdjacentLiteralVisitor<'a> {
+        last_expr_was_literal: bool,
+        op: Operator,
+        datatype: DataType,
+        info: &'a SimplifyContext,
+    }
+
+    impl<'a, 'n> TreeNodeVisitor<'n> for AdjacentLiteralVisitor<'a> {
+        type Node = Expr;
+
+        fn f_down(&mut self, node: &'n Self::Node) -> Result<TreeNodeRecursion> {
+            match self.info.get_data_type(node) {
+                Ok(datatype) if datatype == self.datatype => {}
+                _ => {
+                    self.last_expr_was_literal = false;
+                    return Ok(TreeNodeRecursion::Jump);
+                }
+            }
+
+            match node {
+                Expr::BinaryExpr(expr) if expr.op == self.op => {
+                    Ok(TreeNodeRecursion::Continue)
+                }
+                Expr::Literal(_, _) => {
+                    if self.last_expr_was_literal {
+                        Ok(TreeNodeRecursion::Stop)
+                    } else {
+                        self.last_expr_was_literal = true;
+                        Ok(TreeNodeRecursion::Continue)
+                    }
+                }
+                _ => {
+                    self.last_expr_was_literal = false;
+                    Ok(TreeNodeRecursion::Jump)
+                }
+            }
+        }
+    }
+
+    let (op, datatype) = match (expr, info.get_data_type(expr)) {
+        (Expr::BinaryExpr(expr), Ok(datatype)) => (expr.op, datatype),
+        _ => return false,
+    };
+    if !is_associative(op, &datatype) {
+        return false;
+    }
+
+    let mut visitor = AdjacentLiteralVisitor {
+        last_expr_was_literal: false,
+        op,
+        datatype,
+        info,
+    };
+    expr.visit(&mut visitor).unwrap() == TreeNodeRecursion::Stop
+}
+
 /// Checks if `eq_expr` is `A = L1` and `ne_expr` is `A != L2` where L1 != L2.
 /// This pattern can be simplified to just `A = L1` since if A equals L1
 /// and L1 is different from L2, then A is automatically not equal to L2.